Here are 7 Lessons I learned from being a CEO of an $80M/year company.

Define Success

Too many founders build toward goals they never chose. That's the fastest path to frustration. Pick a definition of success that makes sense for you and your team.

Play Offense

Too many companies keep operating from fear long after they've earned the right to get aggressive. When the foundation is strong, that's when you make the hires, investments, and moves that create separation.

Know Numbers

You can't lead well if you're guessing. When you know the numbers cold, you make faster decisions, ask better questions, and avoid emotional swings.

Change Minds

Weak leaders confuse consistency with strength. Strong leaders update fast when the facts change. Be willing to change your mind.

Overpay A-Players

The wrong person looks cheaper only on paper. The right person creates leverage, raises the standard, and makes everyone around them better. Testing your hiring process can help you identify these people.

Do Less

The CEO should do less as the company grows. That doesn't mean caring less. It means doing fewer things personally and making better decisions where it counts. It means empowering the leaders underneath you to make better decisions than you.

Remove Risk

It's fragile, exhausting, and impossible to scale when everything runs through one person. If the business only works when one person is always in the middle, it's weaker than it looks. Build redundancy the second you can afford it. This is why you need to stop being your startup's superman.

Final Thoughts

Here's the thing: these seven lessons won't prevent every mistake. But they might help you skip a few painful ones of your own.

Leadership, growth, and building a company that scales all come down to making better decisions. Define your success, know your numbers, and build a team that doesn't depend on any single person.

I hope these lessons serve you well on your journey.

There's a line Peter Drucker wrote back in 1963 that still stops me in my tracks:

"There is nothing so useless as doing efficiently that which should not be done at all."

Sixty-three years later, it's the opening of my new talk — and the frame for how I see leadership evolving right now.

Three eras, one fast-moving shift

I see modern leadership moving through three distinct eras:

• Manager Mode. The pyramid. A customer signal travels through four management hops before it reaches the person who can actually act on it. Three people have already filtered the information by the time it lands.
• Founder Mode. Flatter. Faster. Decisions concentrate around a single leader instead of a chain of approvers.
• Architect Mode. The emerging era — and in my view, the one pulling away from the others the fastest.

So what is Architect Mode?

Manager Mode centralizes decisions through hierarchy. Founder Mode centralizes them through one person.

Architect Mode does the opposite. My job as the leader isn't to make the calls. It's to build the systems that let smart decisions happen without me.

In practice, that means designing frameworks that distribute authority, removing the bottlenecks that slow good ideas down, and building a structure that scales past any single person in the room — including me.

The bet that made the case

This isn't theoretical for me. Back in 2017, well before AI adoption was a real conversation, I placed a bet at AppSumo: hiring is a sign of failure.

Over the next five years, we grew AppSumo from 3Mto3Mto84M. A 28x jump — without the proportional headcount growth most companies assume is required.

At Agoge, the company I run now, we've since helped clients generate more than $1B in growth using the same thinking.

Take a look

The full deck is 29 slides. If you want to walk through it at your own pace.

VIEW FULL CONTENT HERE

I've seen some founders keep high performers around because "they get results." And I've seen others keep trusted people around because "they've been with us forever."

Both mistakes are expensive.

The Framework

Here's the framework I use:

• High performance + High trust = Star. These are the people you build around. Give them more responsibility. Give them leverage. Keep them close.
• High performance + Mid trust = Tune. The output is there, but something still needs work. Usually communication, consistency, or ownership. Worth developing.
• High performance + Low trust = Toxic. Toxic high performers are the most expensive people in your company. They may hit numbers, but they drain the team. They create politics, fear, and inconsistency.
• Low performance + Mid trust = Salvage. If the character is there, it may be a role issue, a management issue, or a training issue. Diagnose before you decide.
• Low performance + Low trust = Cut. No performance and no trust is the clearest signal on the board.

Everything else should be a coaching moment.

Trust Compounds

Trust makes performance sustainable.

If someone hits the number but breaks the culture, you didn't win. You just borrowed results and paid for them with team health.

Many founders get this wrong because they only ask: "Are they performing?"

The better question is: "What happens to the team if we keep them?"

The Bottom Line

Performance matters. But trust is what determines whether performance compounds or corrodes.

That's why the best teams aren't built with talent alone. They're built with talent you can trust. When you're scaling your business, getting this balance right becomes even more critical.

If you're making the most critical hire for your team, don't just ask if they can perform. Ask if they can be trusted.

When I look back at AppSumo's growth, I can count maybe 5 projects that truly changed the trajectory. Most quarters it was one.

The Three Rules

Which is why I created the One Hill Doctrine.

It follows 3 rules:

• Only one Must-Have per quarter
• It must be fully staffed and resourced
• Nothing else gets priority until it ships

One project CEO. One team. One hill.

Actually Execute

This is how you stop pretending to execute and actually move the business forward.

I turned it into a simple operating template our CEOs use for quarterly planning.

Get Started

Stop spreading your team thin across dozens of initiatives. Pick one hill. Staff it fully. Ship it before moving on.

When you focus on one Must-Have per quarter, you'll finally see real progress instead of busy work.

Try the One Hill Doctrine for your next quarter and watch what happens when your entire team rallies around a single goal.

At-Risk Roles

Here's the thing. Some roles are getting hit harder than others right now:

• Customer support reps
• Project managers (the status trackers)
• Low-level copywriters
• Junior designers
• SDRs doing manual outbound
• Recruiters doing resume screening
• Data entry and ops coordinators
• "Generalists" with no clear output

Shrinking Fast

And it's not stopping there. These roles are shrinking fast too:

• Engineers who don't use AI
• Marketers who can't ship
• Analysts who only report, not decide

What's Happening

One A-player with AI can replace 5 to 10 average employees. Speed is now a moat. "Headcount" is no longer a flex.

The new rule? If your job is repeatable, spec-driven, or can be turned into a prompt, it's on the chopping block.

What Survives

Look, not everyone is at risk. The people who survive are:

• People who own outcomes, not tasks
• People who use AI to multiply themselves
• People who can make decisions under uncertainty
• People who can sell, lead, or build

Tasks vs. Outcomes

What's the difference between "owning tasks" and "owning outcomes"?

A task-owner writes 10 blog posts a month. An outcome-owner figures out which content actually drives revenue, then uses AI to produce 10x more of it. This is what it means to amplify what works in your business.

The Bottom Line

Founders: Stop hiring for tasks. Start hiring for leverage. Your competitors already are. When you're thinking about your next hire, focus on people who multiply output, not just execute checklists.

Employees: The question isn't whether AI will take your job. It's whether you'll be the one using AI or the one being replaced by someone who does.

Which side are you on?

Your real mandate is simpler: Protect. Provide. Lead. Decide.

Protect

When you hire someone, you're asking them to trust you with their family's livelihood.

Don't hire too fast. Don't plan around fear. Don't use layoffs as a panic button.

Protecting your team doesn't mean avoiding hard decisions. It means not making reckless ones.

Provide

Give each team member room to grow. Care about them as much as you care about your customers. Maybe more.

If you only want output, hire a contractor. Once they're W2, you're responsible.

Lead

Leadership isn't slogans or culture decks. It's setting standards and holding them. It's having uncomfortable conversations early. It's showing people what "good" actually looks like.

You can care about people and still expect results. Those aren't opposites. They reinforce each other. This is one of the things I wish I had done sooner as a CEO.

Decide

Your team should never be guessing what matters. They need clear priorities. The right tools. And enough context to make good decisions without waiting on you.

Indecision doesn't feel like a decision. But your team pays for it anyway with meetings, busywork, and wasted momentum.

The Bottom Line

Being a CEO isn't about vision alone. The real work shows up in decisions most people never see: Protect. Provide. Lead. Decide.

These four responsibilities don't get the spotlight. But they're what separates leaders who build lasting companies from those who burn through teams.

Which one are you neglecting?

That wiring can build extraordinary companies. It can also make it nearly impossible to turn off.

Always On

I can't tell you how many founders I see who feel guilty when they're not working.

They're home but on Slack. At dinner but checking Stripe. On vacation but thinking about churn.

You can run like that for a few seasons. You can't run like that for decades.

One Practical Tool

If I could give one practical tool to protect your mental health, it's this: Time block your genius hours.

Identify when you do your highest-leverage thinking and use it to work on the real constraint in the business. Then shut it down. Completely.

"But the work isn't finished."

It never is. And that's fine.

Your Other Roles

You likely have another role that matters. Spouse. Parent. Leader. Human.

The business will take everything you're willing to give it. Your responsibility is to decide the boundary. If you're trying to stop being your startup's superman, this is where it starts.

You don't build a durable company by burning out the founder.

Take Action

The most important thing you can do is set boundaries and protect your mental health. Time block your genius hours, do your highest-leverage work, then shut it down completely.

Building a business that scales requires a founder who can sustain the journey. That means taking care of yourself first.

Take care of yourself.

Here are five questions to help you figure it out.

Starting vs. Improving

Do you enjoy starting new things, or organizing and improving existing things?

Some CEOs thrive on the chaos of creation. Others excel at taking something that exists and making it better. Knowing which one you are helps you understand where you'll add the most value.

Your Top Skill

What's your top skill?

This isn't about what you're decent at. It's about what you're genuinely great at. Your answer shapes the type of company you should build and the team you need around you.

Your End Goal

What's your personal end goal?

Some founders want to build something massive and exit. Others want to create generational wealth. And some just want freedom. There's no wrong answer, but you need to know yours.

Lifestyle or Scale

Do you want a lifestyle business or a big business?

A lifestyle business gives you flexibility and control. A big business means growth, investors, and a different kind of pressure. Both are valid. But they require completely different approaches as CEO.

Can You Sell

Can you sell people on a vision?

Every CEO needs to sell. You're selling to customers, investors, and your own team. If you can't get people excited about where you're going, you'll struggle to get there.

The Bottom Line

These five questions cut to the core of your leadership identity. Your answers reveal whether you're a builder or optimizer, what drives you, and whether you have what it takes to rally people around your mission.

There's no perfect CEO type. But there is a right fit between who you are and what you're building. The more honest you are with yourself, the better decisions you'll make. And that's something every CEO wishes they'd figured out sooner.

Take a few minutes to answer these questions honestly and see what they reveal about your leadership style.

Do this instead.

Early Warning

6-8 weeks before:

"Something needs to change or the role will change. Let's fix it together. I'll do everything I can to help you succeed, but if this doesn't improve, we'll need to have a more serious conversation about whether this role is the right fit."

Clear Checkpoints

Here's our plan for the next [X weeks]:

Week 1-2:

• [Specific action or process to implement]
• Weekly 30-min check-ins to review progress
• [Specific deliverable or milestone]

Week 3-4:

• [Measurable milestone]
• Continue check-ins, potentially shift to every-other-week

Success looks like: [Clear, measurable outcomes]

If we're not seeing this improvement by [specific date], we'll need to have a more serious conversation about whether the role is the right fit.

Make It Collaborative

I believe you can do this. [Acknowledge their strengths/value]. But I need you to [describe the shift needed].

What support do you need from me? What would help you [achieve expected outcome]? Is there a process or tool that would make this easier?

End With Clarity

To be really direct: This is critical. [Explain why it matters to the business/team]. I'm committed to helping you succeed in this, but I need to see you meeting this standard consistently.

Any questions or concerns?

After The Conversation

• Send a recap email or Slack message with what you discussed to have it documented
• Clearly outline the action items, timeline, and success criteria
• Schedule follow-up check-ins

Key Takeaways

The biggest mistake is waiting until firing day to have the tough conversation. Instead, give your team member 6-8 weeks of warning, clear checkpoints, and genuine support to improve. Make it collaborative, end with clarity, and document everything after the conversation.

This approach gives people a real chance to succeed while protecting both you and your team. If you're testing your hiring process, you'll make fewer of these mistakes in the first place. And as you learn what to do sooner as CEO, handling tough conversations early becomes second nature.

Start the conversation before it's too late.

The Role Shift

As an individual contributor, the job is clear. Reach out to prospects. Close deals. Hit the target.

Management is a completely different job.

A salesperson wins by being exceptional themselves. A sales leader wins by making other people better.

What Leadership Requires

That means:

• Reviewing calls and spotting patterns
• Designing comp plans that drive the right behavior
• Training the team so performance improves without them in the room

None of that is required to be a great closer.

The Double Problem

Promoting someone purely because of performance usually creates 2 problems at once:

• You lose your best individual contributor
• You get an untrained manager

The result looks like "leadership issues," but it's really a role mismatch.

Different Roles

Some people create output. Some people create environments where output compounds.

Both are valuable. They're just not the same role.

Conclusion

Your job as CEO is to place the right people in the right position. When you promote based on performance alone, you risk losing a top contributor and gaining an unprepared leader. Recognize that creating output and creating environments where output compounds are two distinct skill sets.

The best leaders understand that management requires a completely different approach than individual contribution. Before your next promotion decision, consider whether you're matching the person to the role or simply rewarding past performance.

If you're a CEO looking to scale, start by evaluating whether your team members are in positions that match their true strengths.

Don't Wait

If you want A+ players, you don’t post and wait. You pursue them. You pitch them. You sell them a better and bigger opportunity.

Give Reason

A players already have leverage. You need to give them a reason to give it up.

Start Conversations

The best hires I’ve made didn’t start with an application. They started with a conversation. And usually months before the person ever joined. If your hiring strategy is “post and wait,” you’ll never build an A+ team. It's important to understand that A+ players are often considered

• 

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. In summary, top talent is not actively searching for jobs; they are often happily employed. To attract A+ players, pursue them directly, offer them compelling opportunities, and initiate conversations well in advance of their potential start date. If your current hiring strategy revolves around simply posting and waiting, you'll likely miss out on building a high-performing team. Remember, the best hires often come from proactive engagement and relationship-building, not from passive job postings. Start pursuing those A+ players today. Ready to build your A+ team? Check out this

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  My 4-Question Test for Hiring

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  Here is my four-question litmus test that I use before hiring anyone. The Average Do…

!

Costly Mistake

Early on, we over-invested in engineering and design. Great intentions. Wrong timing.

Revenue stayed flat. Profits shrank. And suddenly we had less money to invest the following year.

The Problem

When I finally sat down with the P&L, the problem was obvious: We didn't hire to unlock growth. We hired to make existing work more comfortable.

That's a subtle but expensive mistake.

Adding headcount without removing a bottleneck doesn't create leverage. It just spreads the same output across more people.

New Rule

That's when RPE became non-negotiable. Every role had to do one of two things:

• Bring in new customers
• Retain the ones we already had

If a hire couldn't clearly do one of those, it was a "not yet." This approach became central to how we handled the most critical hire decisions.

Tracking Growth

From then on, we tracked RPE monthly. We tracked it by department.

And we stopped hiring to discover growth. We only hired to scale it. This mindset shift was essential for amplifying what works.

Key Takeaways

Revenue per employee is a powerful metric for building a lean, profitable company. Hire to unlock growth, not to make existing work more comfortable. Every role should either bring in new customers or retain the ones you already have.

When you stop hiring to discover growth and only hire to scale it, you create real leverage in your business.

Track your RPE monthly and by department to keep your team focused on what matters.

You're dead last.

You COULD grind harder, work longer hours, perfect your script. But instead you do something none of your competitors ever thought to do.

You look at the data about who's actually buying the newspapers.

I've written more about this in Why Most $1M CEOs Fail at $10M.

Finding Patterns

And you find a pattern: Every single buyer moved into their home in the last 90 days.

• New homeowners were setting up routines
• Establishing utilities
• Building a sense of belonging

And having a newsletter subscription was the cherry on the cake to feel integrated.

So while everyone else knocks on random doors, you walk into the county clerk's office. Pull public records of every home sold in the last 90 days. Free information.

And you only knock on THOSE doors.

This is exactly the kind of thinking that separates those who struggle to grow from those who amplify what works. Instead of doing more of what isn't working, they find leverage.

The Results

• 1 sale per 100 doors → 1 sale per 8
• Daily sales up 1,200%
• Fewer hours worked
• Dead last → #1 on the leaderboard

Your competitors can't figure out how you did it.

Well, it had little to do with talent. You got better at finding the right people instead of convincing the wrong ones.

This lesson applies whether you're a teenager selling subscriptions or a founder trying to stop being your startup's superman. The goal isn't to outwork everyone. It's to find the path they aren't taking.

The Same Principle

This was Michael Dell at 16. And he used the exact same principle to build Dell Computer.

When he entered the PC market, he didn't try to out-Apple Apple or out-IBM IBM. He ignored retail shelves entirely.

Instead, he focused on a very specific customer: Business buyers who wanted custom-built machines and direct relationships.

And built everything around them.

That strategy made him:

• The youngest Fortune 500 CEO
• A decades-long tech leader
• Over $50B in personal wealth

The Takeaway

The lesson from the paper route never changed: Success doesn't come from being marginally better at serving everyone. It comes from being way better at serving a specific someone.

Finding the right people beats convincing the wrong ones every single time. Whether you're selling newspaper subscriptions or building a tech empire, the principle remains the same. Focus on who actually needs what you're offering, and build everything around them.

See you at $1b.

No data transfers. No migrating old files. No carrying forward the digital clutter from the previous year.

Just a clean slate and a fresh start.

I explore this further in The Biggest Firing Mistake I've Made.

Idea Behind The Ritual

This approach might sound wasteful or unnecessary, but here’s the reality: if my setup makes me even 1% more efficient, it pays for itself in the first week.

When you consider how much time we spend on our computers, that 1% compounds rapidly into hours of saved time and increased productivity.

The Essential Apps

The first thing I do after unboxing is download my core productivity toolkit.

These aren’t random apps, these are tools I’ve tested and refined over years of experimentation:

• Paste App: In my opinion, this is the best copy and paste tool in the entire Apple ecosystem. It transforms the clipboard from a single-use tool into a powerful productivity multiplier.
• BetterSnapTool: This app enables split-screen or quad-box window management, making multitasking seamless and intuitive.
• Chrome: My browser of choice for its speed, extensions, and cross-platform syncing capabilities.
• Superhuman: Email is still the backbone of business communication, and Superhuman makes managing it actually enjoyable.
• CloudApp: Simply put, the best screenshotting app available. Screenshots and screen recordings are essential for modern communication.
• Google Drive: For cloud storage and collaboration, this remains unbeatable.
• Notion: I stand by this: Notion is the best productivity app of all time. It’s my second brain, project manager, and knowledge base all in one.

System Settings That Make a Difference

After the apps are installed, I focus on the system settings that most people overlook but make a massive difference in daily use:

First, I change my trackpad sensitivity settings to maximum. This might feel too fast for some, but once you adjust, the speed boost in navigation is incredible. Every cursor movement is more efficient.

Next, I log into Motion, my go-to calendar and scheduling app. Time management is everything, and Motion helps me visualize and optimize how I spend every hour.

Then comes the cleanup: I remove all the garbage Mac apps from my menu bar and turn on minimization. A cluttered menu bar is a cluttered mind.

These systems have served me well as CEO. I share the broader lessons in My CEO Story.

I want to see only what matters.

Finally, I change my wallpaper to make this MacBook truly mine. It might seem superficial, but personalizing your workspace creates a psychological connection that enhances focus and ownership.

Conclusion

While I’ve shared my specific app choices and settings, the real lesson here isn’t about copying my exact setup. It’s about being intentional with your tools and workspace.

Ask yourself: What apps do I actually use every day? What settings frustrate me that I could change? What would my ideal digital workspace look like?

Then build it deliberately, rather than letting it accumulate organically over time.

Your productivity system should serve you, not the other way around. A fresh start, whether annually or just when needed, is one of the best ways to ensure that remains true.

I learned this while leading an $80M business.

My weekly rhythm is simple: plan on Sunday, execute Monday through Thursday, clean up Friday, and rest Saturday.

Sunday is not the end of the week.

It is the start of the next one.

30 minutes on Sunday equals 30 hours of clarity during the week.

My Planning Session

Here is what my 30-minute Sunday planning session looks like:

Schedule Workouts First

I book them like board meetings.

Missing a workout equals missing a week of peak performance.

Your brain is a muscle.

Train it.

Write Down Wins

I keep a file of things that would have blown my mind 5 years ago.

Example: Last week, my team closed 3 deals while I was at my son's soccer game.

That is systems working.

Recommit to Goals

90-day goals keep you close to your 25-year vision.

Ask:

"What is my biggest bottleneck right now, and what 3 actions move me closer this week?"

Run the Correction

Planes are off course 97% of the time.

So are you.

What worked?

What did not?

What needs a 2-degree shift?

Small corrections compound.

Write Your Big 3

3 priorities you can hit with 90% confidence.

Momentum beats perfection.

Transfer Open Tasks

Clear the mental RAM.

Every open loop is a productivity leak.

Delegate it, delete it, or do it.

No exceptions.

Choose Your Reward

Hit your Big 3?

Book that massage.

Buy that watch.

Call your mom.

Celebration is not soft.

It is strategic.

Make Success Unavoidable

Running shoes by the bed.

Protein shake in the fridge.

Phone in another room.

Sticky note with goals on laptop.

Separate Deep Work login.

Environment beats willpower.

Write Each Report's Priority

If your CFO thinks their priority is a hiring roadmap, but you think it is cash flow, you have already lost the week.

Alignment equals acceleration.

Block Deep Work

Meetings are where productivity goes to die.

Block 2- to 4-hour chunks for real work.

Guard them, as your company depends on it.

Because it does.

Final Thought

Show me your calendar, and I will show you your priorities.

Most CEOs plan their week around meetings.

I plan mine around momentum.

That is the difference between being busy and building.

Conclusion

Win Sunday, win the week.

30 minutes of planning creates 30 hours of clarity.

The difference between an eight-figure company and everything else is not just hard work, it is intentional preparation.

Follow me on LinkedIn and Instagram for more.

Get cash upfront, lock in customers, and show impressive metrics to investors.

Everyone does it, right?

But after watching companies nearly collapse from this strategy, I learned the hard way: annual plans might be the greatest scam in SaaS.

The Math

If your net margin is 15% and you are giving a 10% discount for annual plans, you are not being strategic.

You are robbing your future.

The math is simple:

• 15% margin minus 10% discount equals 5% margin
• You just gave away 67% of your profit
• To get cash today that you will burn tomorrow

The Cycle

Here is where it gets even more dangerous:

January: Your bank account is fat. Annual payments everywhere.

February: You hire 3 new engineers, 2 salespeople, and 2 more customer success.

March: Monthly recurring revenue looks amazing on paper. But no new cash is coming in.

April: Payroll hits. Where did all the money go?

You have built a company on phantom revenue.

Those annual prepayments? They are not recurring.

They are a one-time sugar high that tricks you into thinking you are richer than you are.

The Reality

I watched a company almost die this way:

Q4: Pushed hard for annual deals. Celebrated the "record quarter." Gave out fat bonuses.

Q1: Hired aggressively based on that monthly recurring revenue.

Q2: Had to look 12 people in the eye and tell them the job they moved cities for was gone.

Because they got high on our own supply.

The Problem

The worst part?

Your "monthly recurring revenue" is a lie.

Your cash flow is a disaster.

And your best customers? They are locked in at a discount, while your worst customers pay full price monthly and churn early.

The Solution

Meanwhile, the companies actually hitting 100 million dollars in annual recurring revenue?

They know exactly what is real.

They use annual plans strategically.

They do not just discount but "give away" features that increase lock-in (more seats).

No phantom monthly recurring revenue. No false confidence. No Q2 surprises.

Final Thoughts

The uncomfortable truth: Annual discounts are startup suicide in slow motion.

You are trading sustainable growth for a high that ends in layoffs.

Your pricing strategy is not just about revenue.

It is about survival.

Choose wisely.

Conclusion

Annual plans can destroy your company if you use them wrong.

The discount eats your margins, the upfront cash creates phantom revenue, and you end up hiring based on metrics that are not real.

Use annual plans strategically, or do not use them at all.

Follow me on X and LinkedIn for more insights.

They shut down six months later.

Here is the uncomfortable truth about marketing stacks: Most founders buy enterprise tools at one million dollars and duct-tape Zapier at one hundred million dollars.

Completely backwards.

$1M Stack

Buy speed, not scale.

Email: Kit

Analytics: Fathom

Docs: Notion

Growth: Meta plus X

Ops: Airtable plus Zapier

Design: Canva

Total cost: Less than five hundred dollars per month.

Setup time: One weekend.

You do not need automation.

You need momentum.

$10M Stack

Build systems, not hacks.

CRM plus Email: HubSpot

Analytics: Mixpanel

Projects: Notion

Growth: Meta plus YouTube plus SEO

Attribution: Triple Whale

Brand: Figma

Total cost: Approximately three thousand dollars per month.

Setup: Two to four weeks.

Repeat what works.

Systematize it.

Kill what does not.

$100M Stack

Integrate or die.

CRM: HubSpot or Salesforce (finally makes sense)

Analytics: Looker plus Snowflake

Ops: Confluence plus Jira

Growth: Multi-channel team across five-plus paid and organic channels

Data: Segment plus Custom Data Team

Brand: Custom plus outsourced brand studio

At this stage, cost does not matter.

Return on investment does.

The Pattern

I have paid one hundred thousand dollars for software that made ten million dollars.

And one thousand dollars for software that costs us millions.

• 

  Why Most $1M CEOs Fail at $10M

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At ten million dollars, with systems.

At one hundred million dollars, with integrations.

Real Scale

Most companies think they are scaling.

They are just adding complexity.

Real scale is not more tools.

It is fewer handoffs.

Next time a vendor pitches you "enterprise-grade" anything under ten million dollars, send them this post instead.

See you at one hundred million dollars.

Conclusion

The right tools depend on your stage, not your ambition.

Speed beats scale at one million dollars, systems beat hacks at ten million dollars, and integration beats everything at one hundred million dollars.

Stop buying for where you want to be and start building for where you are.

Follow me on LinkedIn or Instagram for more.

Every minute was color-coded, time-blocked, and optimized.

I had every productivity app installed and a system that would make any efficiency expert proud.

Year 2 at AppSumo, we hit $7M in revenue.

I was also working 60-hour weeks and dead by Friday.

The Shift

Year 5 at AppSumo looked completely different.

I tracked my energy instead of my time.

I deleted half my meetings.

No calls before noon became a rule.

Result: $50M+ revenue, working 40-hour weeks, energized on weekends.

The difference was not time.

It was energy.

The Discovery

I tracked my energy hourly for 90 days.

What I discovered changed everything:

• 9 am-11 am: Strategic genius mode (worth $10k/hour)
• 11 am-1 pm: Barely functional human (worth $100/hour)
• Post-workout: Second wind that lasted 3 hours

Yet I was scheduling catch-up calls at 9 am and deep work at 3 pm.

Backwards.

Expensive.

Stupid.

Energy Management

I replaced time management with something better.

The Energy Audit (do this tomorrow):

1. Track your energy 1-10 every hour for one week (use a spreadsheet)
2. Find your genius windows (8+ energy)
3. Find your zombie zones (4 or below)
4. Redesign your calendar around your energy levels

My Rules

My non-negotiables now:

• No meetings before noon
• Deep work only in genius windows
• Workout at noon to create afternoon energy
• Kill any recurring meeting that drains more than it delivers

The most productive CEOs I know have more blank space on their calendars.

Because they understand something fundamental.

The Truth

You can always find more time.

You cannot manufacture more energy.

One bad 9 am status meeting costs more than missing a whole day of work.

That quick sync just stole your most valuable thinking time.

That afternoon deep work session?

You are operating at 20% capacity.

Your Move

While everyone else optimizes their calendar, optimize your energy.

Cancel your worst recurring meeting this week.

Put deep work in your genius window instead.

Watch what happens.

Conclusion

Energy management beats time management at every level.

Track your energy for a week, find your genius windows, and redesign your schedule around when you are actually at your best.

The results will follow.

See you at $100M.

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I see a lot of confusion around titles like Founder, CEO, President, and COO.

Here is how I think about the difference between these roles.

The Founder

Takes it from 0 to 1.

The visionary.

Obsessed with the product.

Innovation-focused.

The CEO

Takes it from 1 to 10, or even 100.

Keeper of the vision.

Company-building focused.

Optimizing, scaling, and executing the broader strategy.

The President

Manages day-to-day operations.

Ensures teams are aligned and executing.

Bridges the gap between vision and execution.

The COO

Runs the engine of the business.

Focuses on operational efficiency.

Makes sure everything runs smoothly at scale.

Conclusion

Each leadership role serves a distinct purpose in building a company.

Founders create, CEOs scale, presidents manage execution, and COOs optimize operations.

Understanding these differences helps you build the right team for each stage of growth.

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The results were crazier than expected.

The Experiment

He routed 10% of incoming calls to an AI system.

Here is what happened:

• Resolution times dropped from 24 minutes to 3
• Customer satisfaction scores went way up
• Costs fell by more than half

Even after customers learned they had been speaking with AI, they were happier.

The Real Shift

That conversation got me thinking about how much AI has changed the role of the CEO.

And the answer is: it has not.

The fundamental role of the CEO is and will always be the same: how do I best serve my customers?

What has changed is the range of possible answers.

The New Question

5 years ago, every great customer experience depended on people.

Today, one of the toughest questions a CEO can ask is, "Should this be handled by a person or by AI?"

That decision is harder than it sounds.

The Stakes

If you choose people when AI could do it better, you add complexity to your business in perpetuity.

You might spend 90 days onboarding someone while your competitor implements an AI software that gets smarter every week and runs circles around your solution.

And yet, if you choose AI too early, you risk losing the human connection that makes your company unique.

The Filter

When I talk to CEOs about AI adoption, I tell them to use a simple filter:

1. Is the task repetitive and high volume?
2. Does AI already outperform humans here, or will it soon?
3. Would removing the human hurt the relationship?

If the first 2 are yes and the third is no, automate it.

If not, augment.

The Bottom Line

The CEO's mission has not changed.

But the number of possible answers has exploded.

And the cost of choosing wrong has never been higher.

That is why CEOs today need to spend more time understanding the problems their teams solve and researching what technology is being built to solve them better.

Conclusion

AI has not changed what CEOs need to focus on, but it has made the decisions about how to serve customers infinitely more complex.

The CEOs who win will be the ones who can tell the difference between tasks that need a human touch and those that do not.

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After the dot-com crash forced them to lay off 30% of their workforce, Reed Hastings braced himself for the worst.

He expected devastation, polished résumés, and empty hallways.

Instead, he walked into the most vibrant office he had ever seen.

The Unexpected Result

The layoffs had removed the wrong people.

The ones who did not fit the culture, who slowed the team down, or who were just there for a paycheck.

What could have caused fear instead created clarity and momentum.

The Real Damage

Every leader faces a similar situation eventually.

Keeping the wrong people is more damaging than losing them.

They drain energy, dilute culture, and make your best people question why they are still there.

A Simple Test

Here is a simple exercise I use with the CEOs I coach:

1. List every direct report.
2. Ask yourself: if this person gave 2 weeks’ notice, would I fight to keep them?

If the answer is anything less than an immediate YES, start the clock.

Hire their backup.

Have the conversation.

Make space for the team that will take you where you are trying to go.

What I Have Learned

I have seen this same pattern in every great company I have worked with or advised.

The moment you remove the wrong people, the right ones finally start to shine.

Conclusion

Culture is not defined by who you hire.

It is defined by who you keep.

The Netflix story teaches us that protecting your culture sometimes means making difficult decisions.

When you remove people who do not fit, you create space for your best performers to thrive.

Culture is built by who stays, not just who joins.

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A few years ago, I went to Tony's Business Mastery program while I was running AppSumo.

I walked away with dozens of insights, but one has stayed with me ever since.

The Old Way

Before that trip, I thought the best way to grow was by building more stuff.

We kept adding products, features, and people, thinking that more equals better.

But each launch felt heavier than the last.

And momentum was slowing.

One Simple Shift

Then Tony said something that changed how I saw business: Love your customer more than you love your product.

If you do that, you will always see the market shifting before everyone else.

Think about it.

In our lifetime, we have gone from cassette tapes to Walkmans to iPods to the phone in your pocket.

The customer never changed.

The product did.

What Actually Worked

At AppSumo, every major leap we made, from selling deals to building tools to helping creators grow, came from obsessing over one thing: the entrepreneur on the other side of the screen.

If we had fallen in love with the product, AppSumo would not be where it is today.

Obsessing over our customers kept us alive and helped us grow from $3M to $84M.

Your Only Asset

Every product has an expiration date.

Every business model eventually gets copied.

The only durable asset you have is trust.

When your customer believes you understand them better than anyone else, they will follow you into whatever comes next.

Three Questions

Ask yourself:

• Who are you serving?
• What progress do they want right now?
• How can you help them get there faster and stronger?

Markets will keep changing.

But the people you serve will always want the same thing: to make progress in their lives.

That is your compass.

Stay loyal to it, and you will never lose your way.

Conclusion

The best companies are not built by falling in love with products.

They are built by obsessing over the people they serve.

When you focus on your customer's progress, you will always know where to go next.

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Some decisions should not wait until you feel ready.

Here are the things I should have done sooner as CEO.

Strategic Connections

I should have hosted dinners with inspiring founders much earlier.

The insights and relationships from those conversations were invaluable.

Personal Accountability

Hiring a coach to keep me on track was a game-changer.

Having someone to hold me accountable and challenge my thinking accelerated my growth as a leader.

Revenue Focus

I waited too long to hire a Head of Sales to drive revenue.

This role transformed how we approached growth and freed me to focus on strategy.

Compensation Structure

Aligning compensation with outcomes should have been a priority from day one.

When your team’s success is tied to results, everyone wins.

Energy Management

No meetings before noon became one of my most powerful rules.

Protecting my morning energy for deep work and strategic thinking changed everything.

Team Building

Holding our first offsite brought the team together in ways daily work never could.

The alignment and relationships we built during that time paid dividends for years.

Conclusion

These six moves helped me take my last company from 3 million dollars to 84 million dollars.

If you are a 7 figure founder ready to scale to 8 or 9 figures, these systems and the right guidance can make it possible.

Want to learn how to implement these strategies in your business?

Apply for 1:1 coaching here

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The Startup

In the $0-1M phase, you are not really a CEO at all. You are primarily a salesperson.

Product-market fit is your only mission at this stage. Until it feels like you are wearing a meat suit in a dog park, you have not found it yet.

The signal you are ready to scale? When you cannot keep up with customer demand.

The Scale-Up

The $1M-$100M phase transforms you into a resource allocator. This was my favorite part of the scaling journey.

Your entire job becomes deploying capital and attention to fix bottlenecks.

Think of it like perpetual Plinko; you are constantly dropping resources where they will multiply fastest.

Every resource ball typically gets stuck in one of two places:

• Revenue (not enough customers)
• Delivery (cannot handle more customers)

Your role as CEO? Follow the ball and clear its path.

The Grow-Up

At $100M+, everything becomes political. This is where I chose to step away as we approached this stage.

The focus shifts dramatically from creation to protection.

Your time gets consumed by:

• Tax law
• Privacy regulations
• Legal reviews for marketing emails

You spend your days playing defense because you are just one PR crisis away from writing a $10M check.

Conclusion

The most important lesson I have learned is that great CEOs know their sweet spot. Even more critically, they recognize when they have become the bottleneck and have the courage to step aside.

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After coaching dozens of founding CEOs, I’ve noticed a common pattern: the compulsive need to swoop in and save the day whenever something goes wrong.

I know this pattern intimately because I used to be that person.

The Late Night Wake-Up Call

I remember one particular night that changed everything.

It was 11 PM, and we had a big launch going live.

My inbox was exploding with notifications.

I sat there, exhausted and frustrated, completely convinced this was what great CEOs were supposed to do.

The Mentor’s Wisdom

I confided in a mentor, “I’m starting to think CEO actually stands for Chief Emergency Officer. I’m always solving a new problem.”

His response hit me like a ton of bricks:

“If you’re always putting out fires, you’re the arsonist.”

That one line transformed my entire perspective on leadership.

The Real Problem

The truth became crystal clear: if every problem needs you, you’re the bottleneck.

During my first year as CEO, I mistakenly believed that solving problems quickly meant I was excelling at my job.

I couldn’t have been more wrong.

The Solution

The real breakthrough came when I shifted my approach.

I stopped trying to be the hero.

Instead, I focused on building systems that could solve problems without my intervention.

Your true role as a leader isn’t to save the business; it’s to build a business that doesn’t need saving in the first place.

Conclusion

Being a great CEO isn’t about being Superman. It’s about creating robust systems and processes that enable your business to thrive without constant intervention. The best leaders don’t solve every problem; they prevent problems from occurring in the first place.

Want more leadership insights and startup advice? Follow me on X and LinkedIn where I regularly share lessons learned from coaching founding CEOs.

Founders often get caught up in the excitement of building new things. However, the most successful companies don’t grow by constantly adding complexity. They grow by amplifying what already works. They focus on doing less, but doing it better.

Focus is Key

When AppSumo was stuck at 7 figures, the initial thought was to launch new offers, tools, and markets. But that wasn’t the solution. Real growth happened when we stopped chasing “new” and started perfecting what already worked.

Our Strategy

We took a focused approach:

• Doubled down on our best customer segment.
• Improved the offers they already loved.
• Scaled the systems behind them.

This focus propelled us from $4 million to $84 million in annual revenue.

Apple’s Approach

Apple could build countless products if they wanted to. Instead, they channel their energy into a select few (though Steve Jobs might still think that’s too many!).

The Million-Dollar Question

Before you launch your next idea, ask yourself: Have you earned the right to add complexity? Or are you still only halfway milking the first one?

Don’t get distracted by chasing what you *think* will grow the business. Instead, concentrate on what already *does*.

Conclusion

True scalability comes not from endless expansion, but from refining and amplifying what’s already successful. Focus on your core strengths, improve existing offers, and scale your systems. Before pursuing new ventures, ensure you’ve fully maximized the potential of your current successes.

Ready to amplify your success? Start by identifying your most successful product or service and dedicating your efforts to making it even better.

• Hosted dinners with inspiring founders
• Hired a coach to keep me on track
• Hired a Head of Sales to drive revenue
• Aligned compensation with outcomes
• Implemented a “no meetings before noon” rule
• Held our first company offsite

If you are a seven-figure founder, this is for you.

Host Dinners With Founders

When you cross 10 employees, you can lose your friend circle overnight. The people you hired, many of them friends, become people you need to hold accountable. This period is brutally lonely.

I could not grab happy hours anymore and complain about the business without affecting morale. That’s when I started having dinners with other 7- to 9-figure CEOs. I finally had people who understood my problems. Each issue came with a lesson that someone else had already experienced.

Action Step: Find one CEO to meet with monthly. Invite two to three more to join you every other month.

Protect Your Morning Deep Work

My mornings are for deep work. Period. This is your time to move the needle in the business before everyone else fights for your attention.

Everyone wants the founder’s time. Your job is to protect it.

Hire A Head Of Sales

You have probably heard the phrase, “Nobody can sell like the founder.” This is true, but it’s also irrelevant.

When should you hire a salesperson? Once you hit $1 million in revenue.

• If you are bad at sales: You need help.
• If you are great at sales: You are the bottleneck.

Think about the math. If I can give 110% on sales but only have two days a week to do it, my output is 220%. A dedicated salesperson operating at 80% for five days a week has an output of 400%. They just doubled my results, even if their individual performance is a fraction of mine.

Additionally, when CEOs jump on every discovery call, prospects can smell desperation. But when your sales team handles discovery and brings you in only for strategic discussions? Now you are running a real company.

At $1 million, your job changes completely. You need to find the gold veins (your ideal customer profiles and winning messaging) and then hire miners to extract the gold.

Align Compensation With Outcomes

Almost nobody does this right. Most leaders just offer a salary plus some vague profit-sharing plan. This can create internal conflict.

For example, our Head of Revenue wanted to email our list daily because more emails meant more revenue. At the same time, our Head of Content wanted to improve list health, which meant fewer emails would lead to better engagement.

They fought for an entire year, and our output suffered.

The solution was a 70/30 bonus split.

• Head of Revenue: 70% of the bonus was based on revenue, and 30% was based on list health.
• Head of Content: 70% of the bonus was based on list health, and 30% was based on revenue.

We achieved unity overnight. There was no more back and forth. Align compensation on January 1st, then get out of the way. Come back on December 31st to celebrate.

Hire A Professional Coach

I know, I know. A coach is telling you to hire a coach. But I am fully booked, and there are dozens of great coaches I would recommend over myself. This is about you maximizing your potential.

You need someone non-judgmental who is emotionally detached from your problems. I hired Dan Putt and Mark Fenner, and I even joined Tony Robbins’ $150,000 mastermind when I was a CEO.

I once asked Tony for advice about a crisis I was going through.

Here’s what he told me:

“I have 1,000 employees across 100 countries. Someone is always screwing up somewhere. This is business.”

Your first emergency feels like death. Their 100th crisis is just another Tuesday.

If LeBron James spends $1 million on his development, why aren’t you willing to spend $10,000 on yours?

Hold Your First Offsite

I learned this from Noah Kagan. New hires do not truly feel like part of the team until they attend an offsite. Before that, they are just showing up and going through the motions.

Spending 2% of your payroll on an offsite provides a far greater return than a 2% raise that nobody notices. The result is an outsized boost in retention and productivity. Eight hours together in person beats one hundred Zoom calls. It is the same reason college bonds are so strong.

Conclusion

Looking back, these are the changes that would have accelerated my journey as a CEO.

It boils down to a few core ideas: fiercely protect your time, build a support system of fellow founders, and hire strategically to get out of your own way.

Aligning your team’s compensation with company goals, investing in your own development with a coach, and building real team bonds through offsites are not luxuries—they are essential levers for growth.

These lessons took me years to learn. I would have been a better CEO had I learned them earlier.

What would you add to this list?

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After testing AI on every CEO task for 90 days, I found that only five core responsibilities truly survived and can’t be handed off.

The experience taught me a valuable lesson: AI doesn’t replace CEOs. It sharpens them.

Complete List

The five things a CEO can’t hand off are:

• Vision (where you’re going)
• Culture (how you operate)
• Hiring the exec team (who builds it)
• Resource allocation (where the money goes)
• Cash (keeping the lights on)

Keep reading below to get a deep dive.

Vision

AI as a sparring partner

I used to spend weeks in strategy sessions and endless meetings.

Now, I feed our data into AI. This includes market trends, competitor moves, customer feedback, and P&L trends.

The AI spots patterns I would miss and challenges assumptions I didn’t know I had.

For example, at one portfolio company, AI flagged that 73% of our $10k+ customers who churned showed the same behavior in their first 48 hours.

We had been focused on acquiring new customers while we were losing our best ones. That single insight shifted our entire roadmap.

Culture

AI builds your culture

Culture isn’t about pizza parties or Slack emojis. It’s the speed, clarity, and behavior of your team when you’re not in the room.

AI helps me put our culture into words by writing internal docs, onboarding guides, and standard operating procedures that actually reflect our values.

It also summarizes key moments from team calls and highlights who lived the values, or who didn’t.

Try this prompt:

“Write a 1-page internal culture doc for a fast-moving remote team where speed and ownership are core values.” The result is better than what 90% of consultants charge $50k for.

Hiring Execs

AI as a proficiency test

While testing AI with over 50 executive hires, I learned that there are only two roles in business: Doers and Deciders.

AI just became the best Doer humanity has ever created. But Deciding? That requires judgment, pattern recognition, and having skin in the game. That’s what executives do.

My new test for executives is simple: How well do they use AI? An executive who can’t leverage AI is like a CFO who can’t read financial statements. They’re missing the most powerful tool of our time.

Executives are valuable because they choose the right problems to solve, the right bets to make, and the right people to trust, not because they type faster.

Resource Allocation

AI as your Strategic CFO

Every dollar is a bet on the future. AI helps me place better bets. It runs thousands of scenarios instantly. What if we double our marketing spend? What if we kill that underperforming product? What if we expand internationally?

In a real example, AI showed us that increasing our prices by just 3% would have the same profit impact as doubling our sales team.

Guess which path we picked?

Conclusion

This 90-day experiment proved that AI is not a threat to executive leadership, but a powerful tool to sharpen it. By serving as a strategic partner, culture architect, and financial modeler, AI takes on the role of the ultimate “Doer.” This allows a CEO to focus on “Deciding,” which is where their true value lies.

By embracing these tools, a leader can shift from being a bottleneck to being more focused and strategic. The goal isn’t just to be more efficient; it’s to elevate the quality of work on the core tasks that can never truly be delegated.

Start by asking yourself how AI could help sharpen your focus on your most critical responsibilities.

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These are the subtle signs that predict success before it even happens.

They Prioritize High-Value Work

The most effective CEOs are lazier than their team. This isn’t lazy like sitting on a beach; it’s lazy like refusing to do $50/hour work when they could be doing $5,000/hour thinking.

The best CEOs I know are allergic to busy work. They understand that their primary role is to focus on the few critical decisions that will move the needle, not to get lost in the operational weeds.

This connects to ideas I shared in Pursue A+ Players.

They Embrace Failure As a Teacher

Many leaders are quick to highlight their successes, but a $100M CEO will talk about their failures more than their wins.

Ask them about a success, and they’ll give you two minutes. Ask them about their failures, and you’d better pull up a chair. They have internalized every lesson because they know that pain is the best teacher, and those hard-won lessons are the foundation of future growth.

They Practice Voluntary Suffering

They have hobbies that look like torture to the average person: Brazilian Jiu-Jitsu, ultra-marathons, and daily cold plunges. They actively seek out voluntary suffering.

Why? Because they know involuntary suffering is an inevitable part of business and life. They want to be mentally and physically ready when it arrives.

They Hire People Smarter Than Them

Most CEOs hire down to protect their ego. In contrast, $100M CEOs hire up.

They are not afraid to build a team of experts who challenge them. If they’re not slightly intimidated by their executive team, they know they’re building a kingdom of mediocrity instead of a powerhouse of talent.

Their Calendar Is Mostly Empty

While everyone else is stuck in back-to-back meetings, the most effective leaders protect their time for deep thought. They are focused on thinking three quarters ahead, not just reacting to the current week.

A full calendar means you’re still operating like a founder. An empty one means you’re finally thinking like a CEO.

They Obsess Over Retention

They are obsessed with retention, not just growth. They understand the fundamental math of a sustainable business:

• A 5% improvement in customer retention can lead to a 25-95% increase in profits.
• Keeping an existing customer costs five times less than acquiring a new one.

Is it unsexy? Yes. Is it profitable? Always.

They Confidently Say “I Don’t Know”

Insecure CEOs feel they need to have all the answers. The $100M CEOs have all the questions.

They say “I don’t know” without flinching because they aren’t trying to be the smartest person in the room. They’re trying to build the smartest room. Their goal is to foster an environment of inquiry and discovery, not to be the sole source of wisdom.

Conclusion

The pattern is simple. $100M CEOs consistently do the opposite of what feels natural or easy.

Here is the 7 Green Flags recap:

• They prioritize high-value work
• They embrace failure as a teacher
• They practice voluntary suffering
• They hire people smarter than them
• Their calendar is mostly empty
• They obsess over retention
• They confidently say “I don’t know”

The ones who make it to the top are the ones willing to burn their old playbook. Every. Single. Time.

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These leaders built something from nothing, and their standards reflect that drive.

Here are three non-negotiable rules that will make you irreplaceable.

Bring Solutions

Founders are natural problem-solvers who’ve spent years firefighting. When you walk into their office with just a problem, you’re adding to their mental load instead of lightening it.

Do the work upfront. Identify the issue, research solutions, and come prepared with your recommended path forward.

Outwork Standards

Founders didn’t build companies by accepting “good enough.” They pushed through countless long weeks and maintained impossibly high standards when everyone else would have quit.

Be strategic about where you apply maximum effort. Anticipate what they need before they ask. Deliver work that exceeds their expectations.

Move Fast

Founders operate at breakneck pace because they understand that hesitation equals death in competitive markets. If you’re moving at corporate speed, you’re already falling behind.

When they give you a task, complete it faster than they thought possible while maintaining quality.

Conclusion

These three rules separate the employees founders forget from the ones they can’t imagine working without.

• Don’t bring problems. Bring solutions.
• Outwork their standards
• Move faster than they expect

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The Average

Do they raise the average of the company?

I’m not looking for people who simply keep pace with the rest of the team.

I want to hire the ones who will pull everyone else forward and elevate the entire company.

Passion

Were they born to do this job?

There’s a fundamental difference between a candidate who can do the job and one who feels called to do it.

When someone is truly passionate, it leaks through their words. You can feel it.

Culture

Would I be excited to get stuck in an airport with them?

This is the ultimate culture test. If they don’t fit our specific vibe, it’s an immediate dealbreaker.

Our vibe is:

• Hungry
• Humble
• Weird

If they don’t align with that, I’m not flying with them.

Threat

This is the one question that stops me from ever settling for a candidate who is just “good enough.”

Would I be scared if they joined a competitor?

If I wouldn’t sweat losing them to a rival, why would I hire them in the first place? It’s either a “YES” to all four of these questions, or it’s a “no” from me.

A Lesson Learned Hard

I built this test the hard way. I once let a leader hire without my oversight, and a year later, I had to fire half the team they built.

They had different values and a different vibe, which created a company within the company.

Ever since that experience, I’ve told every CEO I advise to be the final interviewer for at least the first 150 hires.

If you find yourself constantly saying “no” to the candidates your team brings you, don’t lower your standards—raise theirs.

This is critical because early hires don’t just build your product; they build your company.

Once your business hits cruising altitude, changing the crew becomes incredibly expensive and difficult.

Conclusion

To protect your company’s future, every new hire should be a definitive “yes” across the board.

Here are the key takeaways from my hiring framework:

• Elevate the Team: Only hire candidates who will raise the average talent level of your entire company.
• Find Innate Passion: Look for people who are genuinely called to the work, not just capable of doing it.
• Test for Culture: Ensure every new hire passes the “airport test” and aligns with your core values.
• Assess the Threat: Only hire people you would be genuinely afraid to see working for a competitor.
• Own Early Hiring: As a founder or CEO, you must be the final gatekeeper for your first 150 employees to set the right foundation.

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Looking back, there are several game-changing moves I wish I’d made sooner that could have accelerated our growth and improved my effectiveness as a leader.

Network Building

Hosting dinners with inspiring founders opened doors I never knew existed and provided invaluable insights from those who’d walked the path before me.

Personal Development

Hiring a coach to keep me on track was one of the best investments I made in myself and, by extension, my company’s success.

Revenue Growth

Hiring a Head of Sales to drive revenue freed me up to focus on vision and strategy while ensuring our sales engine was properly optimized.

Team Alignment

Aligning compensation with outcomes created the right incentives and motivated everyone to work toward shared goals that truly mattered.

Energy Management

Implementing no meetings before noon gave me protected time for deep work and strategic thinking when my energy was at its peak.

Team Connection

Holding our first offsite brought the team together in ways that regular meetings never could and strengthened our company culture significantly.

Conclusion

The best time to implement these changes was yesterday.

The second best time is now.

Here’s a quick recap of the game-changers:

• Host dinners with inspiring founders
• Hire a coach to keep you on track
• Hire a Head of Sales to drive revenue
• Align compensation with outcomes
• No meetings before noon
• Hold your first offsite

I took my last company from $3m to $84m as CEO.

Now I help 7 figure CEOs do the same.

Apply for 1:1 coaching with me by clicking here.

Full stop. And honestly, the company wouldn’t be where it is today without her.

She applied for an email copywriter role. Now she’s the COO.

Here’s the full story.

I dig deeper into this topic in Pursue A+ Players.

Game-Changing Hire

Call it luck. Call it fate. But here’s what mattered when Ilona came into our orbit:

🎯 We wrote a job post that attracted someone like her.

🫰 We were hiring for a mission-critical role. Copywriting drives revenue, so this wasn’t just another seat to fill.

🔍 And most importantly, we recognized the talent when it walked through the door.

Ilona’s Journey

So what does that kind of talent look like from the other side of the table? Ilona’s journey to AppSumo was driven by a desire for intentional change.

As Ilona shared in her “How I Met AppSumo” LinkedIn series:

“In 2017, I quit my job, packed a U-Haul and drove with my roommate from Seattle to Austin. I had never visited Austin before. Didn’t have a job lined up. Didn’t have a network… I really just wanted a change. And more than that, I wanted to approach my life with intention vs inertia.”

Our job description was the first thing that caught her eye and confirmed she was on the right path:

“I still remember the line in the job description that got me: ‘We offer an all-expenses paid company trip with the team to the local Sheraton — just kidding: last year, we went to Costa Rica.’… I had never seen a company make a job description funny… I just knew this was where I was supposed to be.”

Her commitment was clear from the get-go, even if it involved, as she puts it, “the world’s most embarrassing cover letter.” She didn’t just apply; she went all in.

“I pored over every piece of copy on the website. The joke cadence, the software jargon (I had zero clue what white labeling was, but I knew the people loved it); I used a color dropper and font identifier Chrome extensions to get the hex code and style just right. I made a pricing table in Canva and included the tacos, too. Did I mention I really really wanted this job?”

Ilona’s kickass cover letter intro

The Legally Blonde reference

She went all in

The final decision came down to a crucial perspective. Ilona found out later:

“It was between me and another candidate for the role. The other candidate was a quant guy, data driven, had stronger A/B testing background. I was a lot softer skilled you might say. But legend has it that Ayman Al-Abdullah said it’s easier to learn the numbers than voice, and that perspective altered the course of my life forever.”

The Ripple Effect

This one hire has resulted in tens of millions in extra revenue.

Not to mention peace of mind, better leadership, and someone we trust with the keys to the kingdom.

It underscores the profound impact that finding the right person, not just a person, can have.

Conclusion

So if you’re a CEO looking for your next #2, don’t just look up. Sometimes your future COO applied years ago. (Sometimes, she styled a taco table in Canva.)

The question is: Will you recognize her when she shows up?

Proud of you, Ilona. And everything you’ve built with us 🙏

Read Ilona’s full post by clicking below.

• How I Met AppSumo, A Love Story: Part I
• How I Met AppSumo, A Love Story: Part II

Worked with 9-figure entrepreneurs.

Built teams at one of the fastest-growing startups.

The #1 trait I look for? People who just do things.

Here’s the playbook I wish more people followed: The Permissionless Approach.

The Video

In 2015, I wanted to work for Noah Kagan.

Instead of asking “How can I help?” or “I’ll work for free” I sent him a 53 second video pitching myself.

No résumé. No fancy intro. Just execution.

It changed my life.

Here’s my video:

In 2015, I sent @noahkagan the following video
No résumé. No fancy intro. Just execution.
It changed my life.

In 2025, this is still the move:@juliafedorin did the same for @Shopify—no ask, no application. Just a killer campaign.

<24 hrs later, she had an offer

Proof: Talent… https://t.co/jyJegODHM2 pic.twitter.com/NgE7TArgCD— Ayman Al-Abdullah 🧱 (@aymanalabdul) April 22, 2025

In 2025, this is still the move.

Julia Fedorin did the same for Shopify.

No ask, no application. Just a killer campaign.

Here is Julia’s video:

Hi @Shopify, room for one more? pic.twitter.com/gUVID18s6G— Julia Fedorin ⁂ (@juliafedorin) April 16, 2025

Less than 24 hrs later, she had an offer.

What does this say? Talent that ships gets picked.

CEOs take note. This is the type of talent you want on your team.

Conclusion

The ‘Permissionless Approach isn’t just a hiring hack; it’s a mindset.

It’s about valuing execution over explanation, and initiative over instruction.

Whether you’re aiming to land your dream job like I did, or like Julia did with Shopify, the principle remains: show, don’t just tell.

Talent that ships doesn’t just get picked; it shapes the future.

For CEOs who recognize the power of this proactive talent and want to build teams that embody this spirit to scale from 7 to 8 or 9 figures—just as I guided my last company from $3m to $84m—I offer coaching to help you implement these strategies effectively.

You can explore working with me by clicking here.

In this article, I will show you the exact playbook to hire your first Executive Assistant.

Ayman's Note: This article is just a preview. I’ve built a full Notion system to help you delegate, onboard, and scale with an Executive Assistant. You can grab that at the end of this article.

Know What Kind of Help You Need

Below is the types of Assistants:

• A Virtual Assistant (VA) handles repetitive digital tasks.
• A Personal Assistant (PA) handles errands & home life.
• An Executive Assistant (EA) runs business ops, scheduling, and high-value execution.

If you’re spending 10+ hours a week on admin, you’re losing money by not having an Executive Assistant.

Your focus should be on growth, strategy, and execution—not booking flights or managing your inbox.

For more on this, see The Michael Dell Strategy.

Identify What to Delegate

I use a priority system every morning:

A – Must get done today
B – Nice to have
C – Errands/admin
D – Delegate (takes >15 min, doesn’t need to happen today)

If a task is worth less than $100/hr, I shouldn’t be doing it.

Your Executive Assistant should remove friction from your life and business.

• Business tasks: inbox triage, calendar management, travel, scheduling, podcast prep
• Ops tasks: CRM updates, tracking KPI dashboards, SOP documentation
• Special projects: client coordination, event planning, logistics

Find Your EA the Right Way

Forget job boards. Leverage your network.

The best Executive Assistants are already working for great entrepreneurs.

Ask 5 CEOs: “Who’s your Executive Assistant? Do they have any spare hours?”

I found mine through Dan Go.

1. Ask 5 founders you trust: “Who’s your Executive Assistant? Do they have extra hours?”
2. Get referrals from high-level communities. Most great Executive Assistants come through word-of-mouth.

Test With a Paid Project / Trial Period

Begin with 5–10 hours/week and ramp up as they prove themselves.

Give them real-world tasks like:

• Booking a flight with specific instructions (e.g. under $400)
• Researching competitors
• Creating a summary of a podcast episode
• Drafting an agenda for an upcoming meeting

If they can’t execute small tasks flawlessly, they won’t handle big ones.

If they nail it, increase their hours.

Delegation System

I have a Slack channel called “Ayman Requests.”

Whenever I need something done, I drop it in there.

They own execution so I can stay in my zone of genius.

Not sure what to offload? Use this filter:

• If it takes less than 15 minutes, do it yourself
• If it takes more than 15 minutes and isn’t urgent, delegate
• If it’s worth less than $100 per hour, delegate

Onboard for Speed

Most founders hire an Executive Assistant and expect them to magically figure things out.

Then they get frustrated when mistakes happen.

Your Executive Assistant will only be as good as your onboarding process. Set them up for success from day one.

The first two weeks determine success.

Here’s how to set them up:

• Record a 90-minute Loom explaining your workflow and preferences
• Have them shadow you for a week to learn how you operate
• Start with repeatable tasks, then expand

Correct Mistakes the Right Way

When mistakes inevitably happen:

1. Default to trust – Assume the best intentions.
2. Use extreme ownership – I reframe mistakes as a failure in my process.
3. Correct them

The goal isn’t perfection—it’s continuous improvement.

Here’s how to fix mistakes:

• Small mistake? Send a quick Slack message
• Bigger mistake? Record a Loom video walkthrough
• Recurring mistake? Hop on a call to diagnose patterns
• Still happening? It’s a misalignment—time to part ways

Teach Them to Anticipate Needs

A world-class Executive Assistant doesn’t wait for instructions.

Mine sends me recommendations based on my past actions.

Every month, I ask: What patterns do you notice?

When they start thinking ahead… that’s when you’ve won.

Scale Their Responsibilities Over Time

Once they handle admin, start delegating bigger tasks:

• Event planning
• Podcast research
• Team coordination

The best Executive Assistants grow with you.

Conclusion

Hiring a world-class Executive Assistant isn’t just a productivity hack—it’s a game-changer for your business and peace of mind.

When done right, it unlocks your time, sharpens your focus, and creates space for higher-leverage decisions only you can make.

If you’re making 6-figures without an assistant, YOU are the bottleneck.

Ready to stop being the bottleneck? Click here to find the Notion system for hiring, onboarding, and scaling an Executive Assistant.

Each role serves a specific purpose in the organization’s lifecycle and success.

Founder

Takes it from 0 → 1.

The visionary.

Obsessed with the product.

Innovation-focused.

CEO

Takes it from 1 → 10 (or 100).

Keeper of the vision.

Company-building focused.

Optimizing, scaling, and compounding value.

Thinking ahead.

President

Executes the CEO’s vision.

Keeps the engine running.

The integrator.

Executing the now.

COO

The Chief Product Officer of the company itself.

Owns the systems, processes, SOPs, and automations to ensure execution at scale.

Seamless.

Conclusion

One person can wear multiple hats, but the distinctions matter.

Understanding these differences helps organizations structure leadership effectively, whether distributing these roles among multiple executives or having individuals who embody multiple aspects as the company evolves.

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During our conversation, we explored my framework for scaling businesses from seven to nine figures, drawing from my experience of taking AppSumo from $3M to $84M in revenue.

The insights I’m about to share focus on the critical elements that most founders overlook:

• Customer retention
• Strategic hiring
• Proper incentive structures

We’ll also discuss the crucial mindset shift required to transition from founder to CEO.

Framework Overview

Most founders never break $10m. But not because they aren’t smart or hardworking.

They just don’t know how to scale.

I took AppSumo from $3m to $84m in six years. Bootstrapped.

Here’s the exact framework I used to do it.

The “9 Steps to 9 Figures” Framework

Scaling happens in three phases:

• Startup ($0-$1M): Find product-market fit.
• Scale-up ($1M-$100M): Build a machine.
• Grow-up ($100M+): Protect the legacy.

Each phase requires a different skill set, mindset, and strategy.

9 Steps to 9 Figures

Triple, Triple, Double, Double

Triple your business three years in a row.

Double your business twice in a row.

It looks simple, but it is not.

Here is the roadmap:

Triple, Triple, Double, Double Formula

Growth Fundamentals

Before diving into thinking you can scale as of tomorrow, you need to master a few fundamentals to set the foundation for sustainable growth.

Find Product-Market Fit first

You don’t have product-market fit until it feels like you’re wearing a meat suit in a dog park.

If you’re still convincing customers to buy, you aren’t there yet.

When you can’t keep up with demand, now you’re scaling.

Retention before growth

Building a business without fixing churn is like building a skyscraper on sand.

Every 3% increase in net revenue retention DOUBLES your company’s valuation.

Before you scale, fix retention. Otherwise, you’re filling a leaky bucket.

The 80/20 Growth Rule

• 80% of your resources on what’s already working.
• 20% on new experiments.

At AppSumo, one small test—switching from credits to cash payments for referrals—became an 8-figure revenue channel.

Pro tip: Test small. Scale what works.

Operational Excellence

It’s time to focus on the operational systems that will enable your business to scale efficiently.

If you’re stuck, your problem is either:

• Sales – Not enough leads?

You don’t have a marketing problem, you have a product problem.

• Delivery – Selling more than you can fulfill?

You’re scaling chaos, not a business.

Fix these first.

Hire to scale revenue, not to discover it

Most founders hire too soon.

Your job is to find the gold vein. Your team’s job is to mine it.

Hiring too early = You burn cash.

Hiring too late = You burn out.

Hire only when scaling becomes the bottleneck.

The Shield vs. Sword Framework for decision-making

Rate every decision 1-5 on:

• Impact (Sword) – How big is the upside?
• Effort (Shield) – How much work is it?

Only pursue 8+/10 ideas.

If it’s not a clear win, it’s a distraction.

Team Building & Leadership

​​Your ability to scale depends heavily on the team you build and how you lead them.

Build an executive team that replaces you

Your business only has two core functions:

• Sales (CRO) – Gets Customers
• Delivery (COO) – Keeps Customers

Pro tip: Hire first in your zone of genius. Why?

Because you’ll know what excellence looks like.

A Matter of Time and Focus

The founder is the hardest worker. The CEO is the laziest.

If your calendar is full, you’re still a founder.

A CEO’s job is to think 3–5 quarters ahead while the team executes.

If you’re in meetings all day, you aren’t running the company.

Strategic Growth

With your fundamentals covered and your team in place, it’s time to focus on strategic decisions that will accelerate your growth.

Hyper-niche and dominate

At AppSumo, 80% of our top customers were marketing agencies. So we doubled down on them.

• LTV tripled.
• CAC dropped.
• Revenue exploded.

Most founders try to sell to everyone.

The winners go deep, not wide.

Traditional equity doesn’t motivate employees

Instead, let them choose their comp split:

• Base salary + bonus
• Mix of cash + equity

Now they have skin in the game—and actually value the equity they receive.

Your business is a game of compounding loops

Most founders chase one-time wins. The best companies build systems that compound.

Every process, hire, and test should make the business better over time.

If it doesn’t, rethink it.

If you don’t know your numbers, you’re flying blind

Your team needs a scoreboard to win.

LeBron doesn’t play basketball with the scoreboard off.

If you don’t track:

• LTV (Lifetime Value)
• CAC (Customer Acquisition Cost)
• Churn
• Net Revenue Retention

—you’re guessing.

Personal CEO Dashboard

Conclusion

Scaling isn’t about working harder, it is about working on the right things.

Want the full breakdown?

Check out the full interview below where Greg Isenberg and I take a deep dive into growth, scaling, and avoiding costly mistakes below.

Watch the full interview on Greg Isenberg’s YouTube channel here.

The end. Thanks for reading.

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That man is my father.

I used to say I came from nothing.

No trust fund. No inheritance. No safety net.

But I was wrong.

Legacy of Sacrifice

I am the product of sacrifice.

Of courage.

Of a relentless belief that tomorrow could be better than today.

On the internet, it's easy to believe we are still climbing.

That there is always more to attain on this journey called life.

Perspective and Gratitude

But zoom out.

On a global scale, we are rich beyond measure—not just in wealth, but in opportunity, in freedom, in the sheer audacity to dream.

My family risked everything to provide me with an opportunity.

They sacrificed familiarity of life, culture, and language so that I could live a better life than they did.

Conclusion

I used to say that I came from nothing.

But now I realize that I come from the shadows of people who gave up everything so that I could have a chance at something.

And I won't waste it.

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What started as a casual conversation turned into a deep dive into the often-overlooked aspects of scaling a business – from nearly bankrupting the company during rapid growth to learning why hiring isn’t always the answer.

What You’ll Learn:

• The #1 mistake entrepreneurs make when scaling.
• Why relying on hiring instead of automation can destroy your business.
• The emotional rollercoaster of entrepreneurship and learning to celebrate your wins.

Video

Watch my appearance here:

Video: He Scaled AppSumo from $3M to $85M – And Almost Bankrupted It?

Transcript

Ayman Al-Abdullah: Welcome to episode 85 of New Money Talks.

John Melizanis: Yeah, perfect on the money. First take, we got Mr. Ayman Al-Abdullah.

Ayman Al-Abdullah: What up?

John Melizanis: What up? This is a very good friend of mine. We’ve come very close. We actually worked together. He’s been an amazing mentor of mine too. I’m actually very excited we got him here to New Jersey, which is kind of funny. You do not want to be here.

Ayman Al-Abdullah: The check size was very large to.

John Melizanis: Start off this podcast. Ha. In a sense, there’s this very cool company called Appsumo. If you haven’t heard of it, you should look it up. Amon was the one of the masterminds behind bringing it from 3 to 80. 70, 80, 85, 90 million somewhere over there. There’s a bunch of different numbers there. But he’s an amazing mentor of mine, amazing coach. Happy to have you here. If you want to give us like a little spiel of who you are, how you tell people who the hell you are, pretty much just say, hey, if you walk into a bar and you were going to meet somebody and explain who you were in 30 seconds, I want to hear what that looks like.

Ayman Al-Abdullah: Thanks, John. Appreciate it. Appreciate it. Fellas, thanks for having me out. Yeah, I mean, my name is Ayman. I mean, what I’m most known for is being the former CEO of AppSumo. Joined them when they were doing around $3 million in revenue. Stepped down when we did about 84 in annual revenue. And that was over the course of six years, fully bootstrapped, growing 80% year over year. Grew the team from just myself to over a hundred full time employees and contractors. And the company’s still going strong. Noah, Noah Kagan, who’s a close friend, one of my, consider one of my best friends is the CEO now. And we still work closely together. And it’s been awesome to see that journey of Appsumo from myself being a former customer to now being a almost a hundred million dollar behemoth.

John Melizanis: So my first question, it’s the question I always wanted to ask and I think I’ve asked you before, but I want to hear what your answer is to this. You were never a CEO of a company before. You were at Stream, I don’t believe. So when you stepped in there, the company’s doing 3 million a year. What in the world, the hell did you do to get the company from 3 to 80? I want to know, like what you think you did and what really made that happen in a sense, you know.

Ayman Al-Abdullah: I mean, the first, the first 18 months was literally just keep the lights on you know, because at the time, Noah and the team had transitioned to a new product called Sumome software product. And so I was literally just running the existing playbook, like, keep the lights on. Let’s funnel those profits back into Sumo Me.

John Melizanis: What was the Playbook?

Ayman Al-Abdullah: So the playbook was, close the deal on Monday, write the copy Tuesday, send an email Wednesday, do customer support on Thursday, prospect Friday. Right. So run that playbook over and over again. And so if we’re closing the deals, we got something to sell.

John Melizanis: Interesting.

Ayman Al-Abdullah: And so when we’re running that playbook, all of a sudden you start to learn some trends. So trend number one is, hey, there are certain products that sell better than others. Shocking. Right? That’s number one. Number two, there are. There are certain marketing channels that work better than others. Shocking. And so you start realizing there are certain trends that if you. If I’m spending just as much time closing these other crappy deals or pursuing these other products, and I’m making way more money in these other categories, why the hell would I spend any time on these other categories? And so all of a sudden, our prospecting list changed. And so when our prospecting list changed, all of a sudden, guess what? Revenue goes up. Isn’t that interesting? Right. When we focus on products that actually go do better, that. That does better. Number number two are we are marketing to everybody. And so we were like, well, if we look at our customer base, there’s a few customers that are spending more than everyone else. Once again, shocking.

John Melizanis: Yeah.

Ayman Al-Abdullah: And we realized, like, there’s this one cohort of customers that is outspending our other customers by 10x and yet we’re completely ignoring them. None of our marketing speaks to them. None of our targeting is after them. So why don’t we go and focus on these customers? And ended up realizing, like, holy shit, every single successful company that we’ve ever launched is doing this exact same thing over and over again. They figure out who. Who loves them.

John Melizanis: Yeah, I see.

Ayman Al-Abdullah: And then they just sell better stuff to that individual. And it’s like, in hindsight, it’s like, oh, this is rocket science. This isn’t rocket science. And so when people are like, Aymann, how did you grow it from 3 to 85 million? Like every other company, I found an ICP and I sold them the stuff that they wanted. And it’s not rocket science. It’s actually pretty simple. It’s very repeatable. And literally every company that can follow this process, which is really Persona, product and promotion, you nail these three things. There is no reason. You’re not sitting on an eight figure business.

John Melizanis: Interesting.

Kyle Russell: One of the three P’s that I’ve always heard was people. Like, so people, Product and promotion. What was that first one that you said?

Ayman Al-Abdullah: Persona. Yeah. So interesting. So people is about your internal Personas, your external. I actually hate people. I think the best, the best businesses are solo founderships if you can. Like, business would be a lot more fun if there was a lot less people. Like nobody wants to sit in one on one. No one wants to. I actually think hiring is a sign of failure. It’s your inability to automate a part of the business.

I share my framework for building the right team in My 4-Question Test for Hiring.

So to me, like, I would love nothing, by the way. If you’re, if you’re listening, you have a business, one person running a hundred million, contact me, I’m going to buy it. Because that’s a way, that’s a way more fun company to run versus like performance reviews and cost of living adjustments and sales. It’s like, bro, rolling my eyes. I don’t want to do another HR training. Like, let’s just get to the business. And so when we’re thinking about that, it’s way more important to think about the Persona, you know, and so to me, hiring is a sign of failure. You want to avoid that as much as possible.

John Melizanis: Yeah.

Ayman Al-Abdullah: Because that to me is a sign that you feel.

John Melizanis: But like your first 18 months there, right, you’re like a 30. You were like 30 years old or whatever.

Ayman Al-Abdullah: Like 26.

John Melizanis: That’s what I’m saying. You’re 26. Like you’re not just figuring this shit out. Like how the, how’d you even get to this point to figure that crap out?

Ayman Al-Abdullah: Well, I mean, I started companies in the past for sure. Sold two of them. So it’s not like I’m, I’m, you know, I’m not.

John Melizanis: No, definitely, definitely.

Ayman Al-Abdullah: I’m not brand new to the business game. I’ve been a customer of Appsumo for, you know, since 2011.

John Melizanis: Oh, God.

Ayman Al-Abdullah: So, I mean, I’ve been floating around this soup bowl for years now.

John Melizanis: Yeah, yeah.

Ayman Al-Abdullah: So it’s not like I’m brand new to the game. I knew how to do sales, I knew how to do copy. Definitely not at the appsumo level. Definitely, you know, so Anton Neville, they taught me how to get, you know, appsumo level copywriting. But, you know, at least the raw skills were there for sure.

John Melizanis: Yeah, Got it. So like, you figured out that Persona you wanted to sell to.

Ayman Al-Abdullah: Yeah.

John Melizanis: Then you figured out like what to sell them the product.

Kyle Russell: Can you Go over like what a singular product that you like double down on that was doing really well.

John Melizanis: Give us the first killer. I’m curious what that is too.

Ayman Al-Abdullah: Well, I mean there was a bunch of killers before me, right. But you know, we were at, when I joined we were doing everything. We were doing udemy courses and fonts and design pattern packages and ebooks. And so we’re like, we’re doing everything under the sun but when we’re analyzing we look back and go, okay, we, I’ll give you an example. Appsumo’s bread and butter used to be bundles. So bundles are, we’re going to take 10 products that hopefully are in the same category. Hopefully we’re going to coordinate 10 different founders, 10 different marketing schedules, 10 different redemption. We’re going to write copy for 10 of them, we’re going to put them together and then we’re going to split profits 10 ways. So it’s way more work, 1/10 the money.

John Melizanis: Yeah.

Ayman Al-Abdullah: So like when we realized like, hey, there’s actually this other category that requires 1/10 the work but makes 10x the money and that was for us, Software lifetime deals.

John Melizanis: Interesting.

Ayman Al-Abdullah: And so when we started doubling down on software lifetime deals like we, we basically invented that category. And when we invented like people were tired of paying subscriptions. They’re like, I can’t believe I’m paying subscriptions for a startup that I had two years ago. And they were like tired of it, you know, like, so they were like, if I pay once with appsumo, that’s it, I never have to worry about this again.

John Melizanis: Why would the startup be willing to just like have that lifetime one time payment? Like what’s the, what’s the incentive for them to do that?

Ayman Al-Abdullah: Multiple reasons. So number one, a lot of them are just getting started. So massive exposure. They’re getting their first thousand customers. Oftentimes there’s a lot of upsell opportunities. And so if a customer hits the natural limit, hey, I actually use this product, let me go and upgrade. Additionally, I mean if you think about it, every SaaS still has a customer lifetime value. And so if your lifetime deal is equal to or greater than the, it’s the equivalent of getting all of the MRR upfront anyway.

John (AD): That’s smart.

Ayman Al-Abdullah: And so I mean to me there’s a million reasons why you would want to do it. And some of the most successful companies of all time have launched on Sumo.

John Melizanis: Now another question I had like in the moment, while you’re there, in a sense, do you feel like, oh, this is Going to get to 80 ish million every day. You’re just like, this is a mess. Every single day.

Ayman Al-Abdullah: No, I mean I remember vividly I jumped on the phone with that, with Noah. I was at, I was working at Microsoft at the time, snuck out to the parking lot and I was like, yo, Noah, there’s a lot, this is the exact phrase, there is a lot of meat left on this bone. Because he had transitioned to Sumami. And you know, he’s classical founder. He’s working on a million things for sure. You know, he’s brilliant in that regard. I don’t think there’s anyone better at launching seven figure businesses. But one of the things that you, the transition from founder to CEO is focus and like actually sticking with the thing that’s working for sure. And for me I was like, man, if we just focus on appsumo, there is no reason why, I didn’t think, I didn’t know if I was going to take it to 85, but I was like, there is no reason why this thing can’t.

John Melizanis: I only ask that because like when we have our monthly talks, when I call you on the phone, you’re always so fucking calm. You’re like, dude, this is easy. Just like bang, bang, bang, bang.

Ayman Al-Abdullah: Yeah.

John Melizanis: But like day to day, obviously you’re just like, he’s felt as. I felt this. I’m sure you felt that. You’re just like, this sucks. Like, this is not working.

Ayman Al-Abdullah: Totally.

John Melizanis: You want to punch stuff. You feel like getting punched in the stomach every single day. Right?

Ayman Al-Abdullah: Totally.

John Melizanis: And as someone who has been successful like yourself, you still feel that. Right? Like everybody else. It’s not just, I mean, yeah, that.

Ayman Al-Abdullah: Let’s look at the stock market. Zoom out. If you’re, if you’re in the day to day and you’re like, oh, today sucks. It’s all red. It’s like, oh, of course red. And so if you’re in, if you just see red.

John Melizanis: That’s a great analogy.

Ayman Al-Abdullah: You’re just going to be like, let me sell. Yeah, let me, let me sell out and I’m going to walk away. But if you zoom, zoom out, regardless of who’s in, who’s president, regardless of what war we’re in, regardless of we’re in a recession or not, stocks go up. So zoom out. They’re going to go up, you know, and so if you do the right activities, if you are in the right industry, if you’re willing to ride the tides, ignore the day to day red and focus on the long term green Interesting.

John Melizanis: Yeah, I think that’s. That’s a good way to put it because, like, I feel like everyone, all founders, startup founders, even big business founders, they feel like shit all the time.

Ayman Al-Abdullah: Always.

John Melizanis: Yeah.

Ayman Al-Abdullah: You got to enjoy the feeling like shit. Right. To me, like, entrepreneurship is the crossfit of business. And so if you’re willing to go to the gym and bomb it every single day and go, hell yeah, that was a great workout. That is how you know that this is the game for you. If you don’t enjoy that, if you’re not willing to go and do 25 thrusters with 225 pounds, this is not the game for you. Go work at the dmv. Go work at the dmv. Right? Like, where you’re. Listen to our lunch break and you’re home by 4. If you don’t want to enjoy the game of entrepreneurship where you’re literally going to be vomiting every single day.

John Melizanis: Yeah.

Ayman Al-Abdullah: Then this is not the game for you.

John Melizanis: Definitely. Yeah, no, it’s. It’s a. It’s a valid point. It’s easier said than done, obviously, because.

Ayman Al-Abdullah: Like, you gotta enjoy it, man.

John Melizanis: Yeah, you gotta enjoy it.

Ayman Al-Abdullah: You gotta. You gotta be more excited about overcoming the challenges than being pissed off that the challenges are in front of you.

John Melizanis: For sure. Yeah. Cause, like, like you said, it’s very simple. It’s just more like you just have to execute on it in practice. Right. So.

Kyle Russell: And it’s also very different. Looking at the day to day versus week to week, month, month, quarter to quarter. Like.

Ayman Al-Abdullah: Yeah.

Kyle Russell: You zoom out further in the stock market where we all just live on a floating rock.

Ayman Al-Abdullah: Yeah.

Kyle Russell: And we have no idea why we’re here.

Ayman Al-Abdullah: Well, this is why. I, like, I have like a giant whiteboard and all I do is I write my wins.

John Melizanis: Interesting. Okay.

Ayman Al-Abdullah: That’s literally all, like, at the end of every week. That’s part of my weekly ritual. One of the first thing that I do is go, what wins that I have this week?

John Melizanis: I’m curious, what’s some of the wins you had lately? If you want to share.

Ayman Al-Abdullah: No, I don’t.

John Melizanis: You don’t want to share?

Ayman Al-Abdullah: Well, I mean, the biggest one is like, I was able to just secure my, like, dream home, you know?

John Melizanis: Congrats on that.

Ayman Al-Abdullah: Working on a 2,000 square foot office, sauna, cold plunge. Yeah. Gym bar that’s gonna have smoothies, supplements, the whole nine. So, like, I’m working through that. So, like, that was like a nice, fun. Yeah. So movie theater room. So literally gonna be doing like live podcasts and all that fun stuff. Like all in this little, you know, there’s, you know, office.

John Melizanis: Yeah.

Ayman Al-Abdullah: So that’s like a fun, fun recent win. You know, I’ve had several clients that have tripled their business in the last year. So that’s, that’s been a lot of fun. Despite a recession for sure. So they’re like hitting record breaking months and they’re in Japan while they’re doing it, like on vacation.

John Melizanis: That’s nuts.

Ayman Al-Abdullah: So to me, like, that’s, I’m way more excited and pumped about that than, than anything else. Yeah, I mean that’s, those are some big ones, but you have to write those down because your brain is an asshole and it’s always going to think about the negative. And so literally it’s right there in front of my desk. Every time I walk by it, all I see is the wins from my last year.

John Melizanis: Interesting.

Ayman Al-Abdullah: And I’m like, that’s a bad motherfucker. And honestly, anytime if you were to just write down all of your wins, I love that you would literally just go like, holy shit, I can do anything.

Kyle Russell: Yeah, that’s her. Moses says hormones says something similar. He’s like, when you come to crossroad where there’s a challenge in front of you, just, you just have to list out all of the, the evidence that you have that you’ve overcome challenge in the past. And so if you build this stack of undeniable proof that you know what it is that you’re doing or that you’ve overcome challenge, or you face adversity and you’ve come out better on the other side, then, you know, it’ll give you that conviction that you’ll be able to, you know, tackle whatever’s ahead of you.

Ayman Al-Abdullah: Yeah, I forgot who it’s. I think it’s Ed my lead, but he’s like, self esteem is the reputation you have with yourself. And what that means is like only, you know, like, hey, I said I was going to do this and I did it. And if you have low self esteem, it’s probably because you keep breaking promises to yourself.

John Melizanis: Wow.

Ayman Al-Abdullah: And if you have high self esteem, it’s because you say you do what you personally say you’re going to do. And so when you can create a list of all of the things that you said you were set out to accomplish and you show yourself that you can accomplish it, your self esteem is going to be through the roof, your confidence is going to be through the roof. And then all of a sudden, any problem that’s going to come Your way is going to feel small and infinitesimal in comparison to who you are as an individual. And the best way to think about that is think about the problems you were dealing with when you were 18 years old. 17. What college you’re going to go to, what business you’re going to create. When are you going to make your first thousand dollars all irrelevant? Now it’s all the tiniest problems in the world for sure, and it’s, it’s a direct result of the promises that you made to yourself that you were able to overcome. And so these problems that you’re facing with right now feel huge because of two things. Number one, they’re brand new to you. You’ve never gone through it before. If it was new, if it was something you’ve gone through before, you’d be like, it’s easy. And then number two, it’s because these problems are now at the level for you. And so for you, you have to recognize that this is a sign actually that I’ve leveled up. And so get excited about it because this is an opportunity for you to go and overcome this particular problem and be able to look back on it the same way you look at your 18.

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John Melizanis: Back to the podcast. Well, this is part of our initial when we first met, you’re like, well why would you want to work with me type. You asked. I think you asked me that.

Ayman Al-Abdullah: Yeah.

John Melizanis: And I was like, well, I can either like learn this shit by getting punched in the face or I can just have you tell me what to do in a sense. And like, obviously you’re not going to be right every single time because you’re not running the business. But like you’re like, hey, from my experience, try this, do this. If it doesn’t work, who cares the fuck? Do something else type of thing. And I think part of what you said is like when a new problem arises, if you don’t have like on it, like craziest thing because he went the route of like he does coaching and everything too, like for E commerce and stuff. And I was always against coaching. And I remember the day I signed up with you. I go to him, I’m like, dude, I signed up for a coach. He’s like, you fucking did. He was like, what? I was like, I don’t know this fucking guy. For some reason I want it because like I realized in my, I’m like, oh shit. Like even the base stuff that we’ve gone through, in a sense, I wouldn’t even think to even think of these things. You’re just like, hey, think of it like this. Like we’re talking about in the cards, like little tidbits of just literally like little actions, like 20 minute conversation with people. It can just change the whole entire business. Yeah, but I wouldn’t have known that if I didn’t have somebody with that experience to tell you. Right, Totally. So part of what you’re saying, when like a new problem arises. Right. I’ve learned a new way to kind of overcome that.

Ayman Al-Abdullah: Yeah.

John Melizanis: You just have people who are like 10, 15, 20 years in life ahead of you experience and in business experience and just ask them, hey, what the hell do you do when this happens? You know, and then it doesn’t happen. You know what I mean?

Ayman Al-Abdullah: So totally. Yeah.

Kyle Russell: A lot of you. So a lot of people look at like the price tag of like coaching courses, etc. As opposed to the likelihood of ROI. If you look at it from ROI, it’s like the information can be terrible, but if you’re a good executor and you can apply it well, then you have to be an idiot to not have an ROI in like halfway decent coaching courses. Like I’ll go through an E commerce course and it’ll be terrible, but there’ll be one application that I can add like a good bundle app or a post purchase Upsell or an email marketing app that has better deliverability. And if I just download that one app, it’ll make me a hundred times more than the cost of the actual course itself.

Ayman Al-Abdullah: Yeah, a hundred percent. I mean, to me, my philosophy is CEOs don't have expenses, they only have investments.

John Melizanis: Do you put this all on Twitter? Like that was on Twitter? Word for word. It’s kind of crazy.

Ayman Al-Abdullah: Yeah.

John Melizanis: Whatever you put online, you actually, like, live it to, which is so 100.

Ayman Al-Abdullah: Well, I mean, I look at my, I look at every line item on my P and L and I go, if I spend $1, I’m expecting 10 back. And so if I’m spending a hundred thousand with a coach, I’m going to expect a million dollars back. And I’ve spent a hundred thousand dollars with a single coach and I’ve gotten significantly more than seven figures back. So I’m always expecting a 10x return. Always. When I’m hiring an individual, I always, I tell them right up front, if I’m paying you 100k, you need to be generating me $1 million a year in revenue. So I’m always looking for that. In fact, we had a rule at Appsumo of every person at appsumo is responsible for a million dollars. So we, our

Having the right support is critical at this stage. I explore this in The Ultimate Guide to Hiring an Executive Assistant.

revenue per employee was 1.1per million dollars. And so we’re always looking for ROI in that.

Kyle Russell: How do you do that for, like a customer support type role, you know?

Ayman Al-Abdullah: Well, you’re only hiring for two reasons. We’re either keeping a customer or getting a customer.

Kyle Russell: So retention.

Ayman Al-Abdullah: And so for customer support, it’s retention 100%. Do you increase my customer retention rate, my customer lifetime value? If I could get rid of customer support and I have zero impact on customer lifetime value, I’d much rather not have a customer support, obviously. Yeah, just let the inbox pile up. All my customers are only buying from me once anyway.

Kyle Russell: Yeah.

Ayman Al-Abdullah: You know, and so like, your, your money is probably better spent somewhere else to increase customer loyalty to the point where, hey, customer support is actually worth your time and effort.

Kyle Russell: Yeah, I think that goes the same for anyone who’s watching as an employee is like, if you don’t know how what you’re doing impacts the revenue of the business, like you need to as soon as possible.

Ayman Al-Abdullah: Yeah.

Kyle Russell: If you want to be valued in that.

Ayman Al-Abdullah: Yeah.

John Melizanis: You made us do that from the beginning.

Ayman Al-Abdullah: Like, that’s the first thing I asked you to do.

John Melizanis: I’m like, you’re like, yo, find a fucking bookkeeper. That’s good.

Ayman Al-Abdullah: How do you, how are you running? Am I allowed to tell you about the revenue?

John Melizanis: Care less.

Ayman Al-Abdullah: How are you running $10 million business without a bookkeeper? I like, blew my mind. I was like, this is absolutely ridiculous. You’re literally flying a plane without any dials. And it’s like you have no idea if you’re about to run out of gas. And so I’m like, that’s the first thing you need is I need your optics. I need you to have a bookkeeper. And I mean, how much more visibility do you have now?

John Melizanis: Yeah, tons. I get one email a month and it tells you everything.

Ayman Al-Abdullah: This is like obvious in hindsight, but it allows you to make much more informed decisions. Like, you know, just the ability to be like, okay, well, worst churn coming from. Where is my cash conversion cycle? Hey, what are we doing year over year? Like, are we even growing? And so I think just having that and your taxes just become so much easier as a result of it.

John Melizanis: Yeah.

Ayman Al-Abdullah: And as one less. I don’t even know who’s doing your books before.

John Melizanis: I would. Me and Joe.

Ayman Al-Abdullah: I mean, you guys are worth $5,000 an hour. Would you ever pay a bookkeeper $5,000 an hour?

John Melizanis: No.

Ayman Al-Abdullah: Exactly. So. But you literally were. That’s exactly what was happening before. You were paying yourself as a bookkeeper, 100%. And so, you know, it’s funny, you were mentioning just earlier, like, just the ability to like, course correct within 20 minutes. Like, I’m going to tell you, like, one of the moments, one of the closest moments I came to dying. I, I’m really big into hiking, mountaineering. I climbed half dome over 10 years ago. This Half Dome, Half Dome’s like in Yosemite. It’s this big mountain. 14 hour. It was 14 hour hike. We were, we were supposed to make it back. So we started about 2 in the morning. We made it to the, to Half Dome. We’re there at like 3 or 4 o’clock and we’re about to head back and we’re hopefully going to be making it back before sundown. But there was a girl at the bottom of Half Dome and she was screaming. She’s like, my dad’s up there. Has anyone seen my dad? And so we ended up like sticking around. We ended up linking up with some EMTs. The EMTs went up, me and my friend, we stayed with her. And he was like 70 plus years old. He was stubborn, refused to come down, kept climbing up the cables. The cables are like almost near vertical. And I guess he got up there and he got stuck and so the EMTs had to go up there, grab him and bring him down while we stayed. Because like literally at this point it’s. This mountain’s empty.

John Melizanis: Geez.

Ayman Al-Abdullah: And so we’re staying with her while the EMTs are going and grabbing her, grabbing her dad brings him down, finally connects her. So at that point it’s like five, the sun’s starting to set and it’s just me and my buddy Carlos. And so we go back. This is like 10 plus years ago. We, I mean our, we basically had cell phone lights. We were very underprepared. This was like early on in my hiking journey. And as we’re heading back, I mean to the point where we’re on cliff faces and we’re walking back like literally with our cell phone lights, like low power mode.

John Melizanis: That’s crazy.

Ayman Al-Abdullah: And like if you just step off, you would literally fall.

John Melizanis: Yeah.

Ayman Al-Abdullah: To your death. And so as we’re climb, as we’re walking, we’re heading left and someone comes back this way. And I just happened to ask like, hey, this is the way back to base camp. And they’re like, no, you turn, you need to turn around. You need to go this way. This way is going to take you through another 140 miles to the next base camp.

John Melizanis: Holy shit.

Ayman Al-Abdullah: And is already pitch black to the point where I couldn’t even see my face. And I’m like, thank God this person came in front of us and we were able to ask them this question. So he’s like, follow me. So we turn around, we follow him and he tells us go left. And we walk through the.

John Melizanis: It’s pitch black, pitch black to the.

Ayman Al-Abdullah: Point where I literally can’t see. I mean, I can go through the full story. There were. There, we were getting, there was mountain lion sightings at the time. So we were constantly like looking up in the mountains to hear because we kept seeing the rocks starting to fall. And I remember looking up like, because I kept hearing the.

John Melizanis: You can’t see your hand?

Ayman Al-Abdullah: I can’t see my hand. And I got a cell phone light. It was very underprepared, super stupid. Now I’m like much more prepared. And as I’m looking up, I see the rock starting to fall. I’m like, dude, there’s a fucking mountain lion following us. And as I look back, look up, I took my cell phone, I look in front of me and I see a giant animal in front of me. And it’s a freaking giant like 12 point buck right on the trail. This is like this skinny little cliff and Carlos jump, like hit, hit, like he didn’t realize what was happening. He like jumped and he almost like pushed me like towards the. And I was like, holy shit, dude. And luckily the buck went back up the. The mountain.

John Melizanis: What the.

Ayman Al-Abdullah: And so, I mean the whole point of the story is the best way to know about the path forward is to ask those coming back. And so when you think about the role of entrepreneurship in business, the only way we know up the path of the mountain is to ask those that have already been there.

John Melizanis: Yeah.

Ayman Al-Abdullah: And to your point, like a 20 minute conversation, a one question, is this the right path to the base camp? Could have honestly saved us from death for sure.

John Melizanis: Yeah. That’s nuts. That’s a crazy story. That’s real.

Ayman Al-Abdullah: It’s dead ass.

John Melizanis: What the fuck?

Ayman Al-Abdullah: Yeah. Yeah. And that was like one of like several things that happened that went very wrong on that particular hike. And so from there I’ve, I’ve completely changed my back. Back loadout.

John Melizanis: Speaking of like stuff going wrong too, I know we talked about in the beginning.

Ayman Al-Abdullah: Yeah.

John Melizanis: You had a story on like what was like the worst thing you ever did at Epson? Like, what was like the biggest mistake you ever made? Because I’m curious on that too. Because, like, you’re not perfect, obviously.

Ayman Al-Abdullah: Oh, I do. I made mistakes. Literally. I mean, look, my content often focuses on what worked well and is a direct result of all the things that went wrong. And so the reason I can speak to, to founders and CEOs is because I’ve literally made every one of these mistakes. I like, I am no, no better than anyone that’s in the trenches that’s dealing with it because I’ve made all these mistakes. And so I’m in the entrepreneur, I’m in the digital space, running a digital business. We do not deal in inventory. You guys are an ecom. You guys understand inventory. I am not. And so this is at the end of the year. I’m not managing the P and L at this time. This is why I asked. You have a bookkeeper. And so at this point, I’m just managing revenue. Right. Gross margins. We’re not hiring a lot. We’re not doing a lot. Noah’s like, hey, we’ve got a shit ton of profit at the end of the year. Great problem to have. It’s like we need to spend it. What should we do? Well, we just launched a new, a new business called Briefcase. It’s kind of like what we thought was going to be the future. It’s like Netflix for entrepreneurs.

John Melizanis: Interesting.

Ayman Al-Abdullah: So you pay once you get access to all these tools.

John Melizanis: Didn’t work out.

Ayman Al-Abdullah: Oh, I mean, it could have is there’s a whole nother reason. But the problem with that is, you know, we, we were validating it by buying the licenses from these founders and then as we would acquire subscribers, we would hand out the licenses. So Noah’s like, hey, we got a ton of profit, let’s spend it. So I drop a million dollars at the end of the year on inventory.

John Melizanis: On what type of inventory?

Ayman Al-Abdullah: Codes. Codes for the.

John Melizanis: Oh, so you paid all these like startups.

Ayman Al-Abdullah: Startups. Markups right up front. It’s like, hey, we’re going to buy 2,000 codes from here, 3,000 codes from here. So that’s. So then spend $1 million. Then I get a text from Noah on Thanksgiving, hey, dude, what’s this chart? What are these charges for? I’m like, what do you mean? You told me to drop this million dollars. And he’s like, there was a ton of miscommunication and immediately ended up realizing, like, did I just put Appsumo into bankruptcy? I spent way too much. There was miscommunication in both directions and I spent way too much.

John Melizanis: Have the million.

Ayman Al-Abdullah: I don’t know. I didn’t have full PNL visibility, so I don’t know how close to crashing this plane I got.

John Melizanis: Geez.

Ayman Al-Abdullah: But like, that was part of the reason I’m like, you need to get a bookkeeper. You need to have full PNL access, understand your cash flow because your cash is your gas tank. And I had no clue how close to. But it, I mean, the way we were both very concerned. I literally was spending Thanksgiving with my family, going over the P and L, going over our cash flow, seeing like how close we were to putting Appsumo out of business. And I was like, holy shit. Like complete miscommunication on my. It was 100% my fault because I should have been asking for more visibility, managing the full P and L. And so number one, I over invested in inventory. Number two, because I didn’t know inventory, I didn’t know about inventory turnover rates and conversion cycles. And so we had way too much inventory.

John Melizanis: I was going to say you bought all this and how’d you know you were going to sell it?

Ayman Al-Abdullah: Exactly.

John Melizanis: You didn’t.

Ayman Al-Abdullah: We didn’t. We had to do a ton of write offs the following year as a result of it, and probably 250,000. That’s a little equivalent of taking a Ferrari and crashing against a brick.

John Melizanis: Wall, you know? Yeah.

Ayman Al-Abdullah: Yeah. So, yeah. So, I mean, it’s. It was a very painful mistake that I made. Number one, almost putting the business out of business. Number two, overinvesting in the wrong things, quite frankly. And then number three, just not having full P and L visibility. And so my philosophy is, you know, like, you know, when I hear that from CEOs, I hear it all the time, and they’re like a. I feel like I’m about to put the company out of business. I’m like, you know what? Congratulations, You’ve graduated. Like, you’re not really CEO until you’ve cried over your P and L on Thanksgiving dinner. Like, that’s the joke that I give. And it’s like, honestly, like, it’s kind of like the trials and tribulations that a lot of founders need to go through for sure, in order to make it through C and L and actually take their finances seriously. Because up until that point, you’re making so much money that you’re just like, I don’t even need to look at my cash flow. I need to look at my P and L. It’s like, we’re just going to grow the business.

John Melizanis: Yeah, I’m curious too. Like, at that level of, like, app sumo business, stuff like that, like, kind of with that growth trajectory, what have you seen as, like, a big factor of, like, failure in a lot of these businesses too? Because, like, it seems like all the positive is online. Obviously all people talk about all the wins and, like, the revenue numbers up into the right stuff like that.

Ayman Al-Abdullah: Yeah.

John Melizanis: But, like, obviously a version of that is like you just spend a million bucks out of nowhere. But that’s also kind of like you guys are trying to think about growth, stuff like that, and instances where the businesses, like, was it times where the business didn’t make a whole bunch of money in profit? You’re like, well, I don’t know why the fuck it’s not working like. Like that too. Or was it always just kind of up and to the right? For the most part, I think that.

Ayman Al-Abdullah: Oftentimes people just think about the CAC to LTV ratios.

John Melizanis: Okay.

Ayman Al-Abdullah: And they just go, hey, let’s just spend as much as we can up into the CAC limit because our CLV is 3x. So for those that, you know, are brand new to the entrepreneurship game, Silva is your customer lifetime value. So let’s say your customer life and value is $300. Your customer acquisition costs, which is your CAC, it’s $100. And so it would seem normal If I can spend $100 to acquire a customer, I’m going to make 3x back of my money. And so why wouldn’t I just keep dropping a hundred dollars?

John Melizanis: Yeah.

Ayman Al-Abdullah: And so I see this is like one of the biggest mistakes that founders can make is they think that the a hundred dollar, the 3x CAC to LTV ratio means they’re, they have free reign to drop the hundred dollars. And so I’ll see some founders spend as much as they can to grow, but then they realize, like, oh, I’m, I’m spent. Let’s just say I spent all of this money in month one. But then they don’t realize that their CLV is actually over three years. So I’m literally pulling all of my cash, burning all of my cash up front, and I’m basically growing myself into bankruptcy and hoping that over the next two and a half years that this is going to pay off. And it happens.

John Melizanis: Cycles just so off, pretty much so off.

Ayman Al-Abdullah: And this is. So if you just focus on the ca, the CAC LTV ratio and you see a lot of gurus out there like, oh, that’s the only thing that matters. Yes. Until it doesn’t. Until you’ve grown yourself into bankruptcy. And I’ve seen several companies actually grow themselves into bankruptcy for sure. And it’s like things are just going up into the right. We’re going like crazy. They hire an ads team, they spend like crazy, and then they go, why don’t we have any cash? Why is there no cash in the bank? Why can’t I buy inventory for Black Friday? Oh, now I got to take out debt.

John Melizanis: Because you spent it all.

Ayman Al-Abdullah: You spent it all acquiring customers that have yet to give you the money back.

John Melizanis: Yeah.

Ayman Al-Abdullah: And so you have gone actually into the negative for this customer and you hope you get it back over the next two, three years. But guess what? You’re not going to be able to because you have no freaking inventory.

John Melizanis: So you want even be alive in three years.

Ayman Al-Abdullah: You’re not even going to be alive in three years. And so that’s one of the biggest mistakes that I see founders make, number two is, you know, making, making the wrong strategic decisions, which is, hey, you decide to launch something new. And so we talked about that, that founder focus. There’s a joke. Year one through year five, keep the main thing. Keep the main thing interesting. Founders in year six go on board. What’s. Let me start something new. And then in year seven, they go, let’s go back to the main thing. The main thing really?

John Melizanis: That’s a joke.

Ayman Al-Abdullah: All the time. All the time. And so I see a lot of founders getting that shiny object syndrome. They want to launch something new, and then in hindsight, they’re like, damn, I should have just stuck with the main thing. So that’s a. That’s a big mistake. If your goal is to grow the main thing, honestly, like, the biggest one is just maintaining cash. Like, you can recover from a bad hire, you can recover from bad strategy. The only. The only time you get knocked out in business is when you run out of cash.

John Melizanis: Yeah, that’s.

Ayman Al-Abdullah: That’s the. That’s the ultimate knockout.

John Melizanis: Interesting. Yeah, that’s a good way to put. That is the truth. If there’s no more money left, there’s no more.

Kyle Russell: Yeah.

John Melizanis: Anything left, it’s done. Yeah.

Ayman Al-Abdullah: I hope I can go get debt. I hope I can use credit cards. But it’s like, at that point, you’re. You’re. You’re pulling the emergency shoot way too late.

John Melizanis: Yeah.

Ayman Al-Abdullah: And you’re hoping that it saves you before you hit the ground.

John Melizanis: For sure. I’m also curious on the coaching, too. Cause I know you got into that recently. Not recently. Like, what, three years? Yeah, three years type thing. What made you kind of go into that? I know it’s a little different than what you were doing, but I’m curious, kind of what made you go into that? How’s that been? Stuff like that, too. Yeah.

Ayman Al-Abdullah: John, man, the plan wasn’t to do anything, right. It was, like, right off in the sunset and, like, sit mai ties on the beach.

John Melizanis: Yeah.

Ayman Al-Abdullah: The problem is, like, you know, guys like us, we get bored. So, you know, two, three weeks in, I’m like, sipping the Mai Tai on the beach. I’m reading the book, and I’m just like, this sucks.

Kyle Russell: Is this it?

Ayman Al-Abdullah: Yeah. Well, it was awesome. Day three.

John Melizanis: Yeah. Yeah.

Ayman Al-Abdullah: Day four, day five, day six, I’m like, all right. Yeah, party on. And by day seven, you’re like this. I’m done.

John Melizanis: Yeah.

Ayman Al-Abdullah: You know, and so you end up realizing, like, oh, like, if you enjoy the game, you enjoy the game. And so the question is, like, okay, well, what do I do next? And so I wasn’t ready to get back in the trenches, you know, But I opened up my email inbox, and I saw 400 emails from companies that had saw me step down, saw what I did at AppSumo, and we’re looking for a CEO, and I just wasn’t ready to take any of those opportunities. But a couple were from friends, and one of them was like, hey, let’s just meet up for coffee. We met up for coffee and we, we ended up, we, we chatted, talked through him and I. He ended up, you know, telling me, he’s like, Ayman, that coffee was one of the most impactful things for the business that I’ve ever, I’ve ever had. I’ve spent hundreds of thousands of dollars in coaching. This coffee by itself was way more impactful than all that coaching. He’s like, I don’t care what your rate is. Like, I need to hire you as a coach. I’m like, I don’t, I’ve never coached before. I don’t do coaching.

John Melizanis: Yeah.

Ayman Al-Abdullah: He’s like, he’s like, whatever it is, like, I’ll pay it because it’s so impactful. And so I was like, all right, fine, let’s, let’s try it. I enjoy, I enjoyed. I enjoy talking business for the coffee.

John Melizanis: Yeah.

Ayman Al-Abdullah: Yeah. Well, I enjoy talking business. So I’m like, sure, let’s do it. And then two months later, he introduced me to two more CEOs. And then all of a sudden, people started talking about me. My reputation started to grow. I’ve had several world famous founders and CEOs tweet about me, which just grows my waiting list even more. And, you know, so I’ve been very fortunate that I’ve got like, like, if you, if you watch them on YouTube, I’ve probably coached them. And so it’s been, it’s been an awesome journey.

John Melizanis: It’s crazy. Yeah, yeah, yeah, yeah, yeah. Well, I don’t anything else.

Kyle Russell: I was going to say, as someone who’s gotten more into the consulting space as well in the coaching space, it’s like, it’s something you have to love doing because it’s not, it’s not a very scalable thing. No, it’s, it’s, it kind of, it’s almost goes backwards on where you want to go in entrepreneurship because it’s all about kind of scaling your dollar per hour. And in most instances when you’re coaching, you’re diluting your dollar per hour because there’s not a lot of leverage involved unless you, you know, bring other people in the mix and hire other coaches, but then they don’t have the same experiences and principles and the teachings that you can provide. So it’s very interesting. You know, you kind of come at a crossroad there.

Ayman Al-Abdullah: I mean, you have to enjoy. I love it. I really. Because it’s an opportunity for me to be in the trenches without being in the trenches. Yeah, Yeah, I really enjoy it. You know, to me, I love the game of entrepreneurship. And I mean, to me, I’ve always been just a natural coach in general. I enjoy. I enjoy seeing athletes thrive. And so I enjoy the game. And to me, it’s not even about the money. I mean, honestly, like, I used to do it for free and I realized, like, nobody would listen. And so now I tell John on the right over here, I. I charge because when you pay, you pay attention. And so, like me, charging my premium rates is a feature, not a bug. And it’s because you’re paying that you take the meeting seriously and you take the advice seriously.

John Melizanis: Yeah, Yeah.

Kyle Russell: I was. I was. For one of my business, I was putting off running ads. And like, I’m an ads guy. I’ve been running ads for E commerce brands for seven years. I was just putting it off and I ended up just like, paying a guy for coaching. He was just like, yeah, basically just do the thing, you know, you needed to do. But now because you’re paying me, you’re actually going to listen to my advice. And so I did it and, you know, six weeks, got it to work very well.

Ayman Al-Abdullah: That’s right.

Kyle Russell: We’re still running it now.

Ayman Al-Abdullah: Yeah. It’s like, I have a personal trainer. I know how to work out. You know, I know how to work out. But it’s like the fact that I’m. And it’s funny, it’s like, not even that much. Like $100 for the hour.

John Melizanis: Yeah.

Ayman Al-Abdullah: The fact that I paid, I’m like, I gotta show up. Like, it’s like, you know, it’s just the fact that it’s on my calendar and I paid for means I got to get my workout in 100%.

Kyle Russell: Yeah.

John Melizanis: I think we got to wrap this up because we gotta.

Kyle Russell: Yeah, this is good. It was a very compact. And that’s all he is, super compact. Has all the concise.

John Melizanis: Yeah, yeah, yeah.

Kyle Russell: You got a big Twitter.

Ayman Al-Abdullah: Not really. Like 20,000.

John Melizanis: That’s big enough.

Kyle Russell: Pretty big. I got like 300.

John Melizanis: Do you want people to find you?

Ayman Al-Abdullah: No.

John Melizanis: You don’t. Right?

Ayman Al-Abdullah: I hope this episode gets like, four views.

John Melizanis: Where can people find you if you want them to find you?

Ayman Al-Abdullah: Don’t look for me.

John Melizanis: Find them online. I’ll tell you. Yeah, your free content’s really good too, though.

Ayman Al-Abdullah: I appreciate that.

John Melizanis: I know Even before we work together, even like that notion template that you have, like just the basic one that is free.

Kyle Russell: I love notion.

John Melizanis: Like game changer.

Ayman Al-Abdullah: I got a notion template for everything. So if you need if you need something notion related DM me, I’ll probably send you the template.

John Melizanis: Yeah. Literally anything. Like, yeah, hiring, firing, I got it all.

Kyle Russell: Sops.

Ayman Al-Abdullah: I’ve got over like 4,000 notion templates, so that’s crazy. Yeah.

Kyle Russell: I remember the first time I saw Justin Kemperman’s. He sent me something about like he was showing me on like a hiring process and I was like, this is so sick. And since that day, everything, I’ve just moved it over.

John Melizanis: I do think every company should have like a wiki notion. Yeah, like that, like the whole. I don’t know what you call it, but like I call it like a ship, dudes, wiki in a sense it just has all like pieces of the business. Game changer.

Ayman Al-Abdullah: Well, I have the free, so that’s. Yeah, I got the free one. It’s pinned on my profile. People want to grab it. They can.

John Melizanis: Yeah, cool. That’s about it.

Kyle Russell: Sweet.

John Melizanis: He has some more coaching. You can’t work with him at capacity. Yeah, yeah, no, but I appreciate you coming on, dude. I know this is a trip for you too far, guys. Shot whoever. Who’s sponsoring this one?

Kyle Russell: Do you remember Omnisend?

John Melizanis: Omnisend. Yeah, Omnisend, we love best.

Kyle Russell: Best email marketing tool for not only e commerce brands but other companies, you know.

John Melizanis: Yeah.

Kyle Russell: Like we’ve been using them for on and off for seven years now, since we got started. And they’re great.

John Melizanis: Very user friendly, 100% send you to all subscribers. Up to almost like 4K subs on this one. Yeah, yeah. TikTok’s big. Instagram’s big.

Kyle Russell: Just got a re. Monetized.

John Melizanis: Remonetized.

Kyle Russell: So if it’s pennies. But it’s, it’s funny, you know, it’s what it’s like, it’s like logging your wins on the whiteboard, you know, it’s just like, all right, you know, we got to get a dollar from this. Two, two here, three there.

Ayman Al-Abdullah: Is it for TikTok?

John Melizanis: No, no, no, no.

Kyle Russell: YouTube.

Ayman Al-Abdullah: YouTube. Yeah, yeah, yeah, yeah.

Kyle Russell: You’d think we were monetized on TikTok. We have like 70k. Yeah, but that was all from like one guy. But anyways, that’s the whole story.

John Melizanis: Anyways, appreciate you guys catch on that.

Kyle Russell: See you in the next one.

John Melizanis: Thank you later.

Nobody really teaches you how to do it.

I took a software marketplace company from $3m to $80m+ in six years as CEO.

Here’s my story (buckle in – it gets bumpy)

The Beginning

“I just don’t have enough time!!”.

It was 11pm and I was monitoring a critical launch for an AppSumo partner.

I was Stressed, Overwhelmed, Burnt out.

To add insult to injury, my team was too.

But since I was CEO, I thought I had to be involved in everything. I remember telling one of my mentors that I felt like my job as CEO was “Chief Emergency Officer”.

Constantly putting out fires.

He told me something that changed my life:

“If you’re always putting out fires, you’re the arsonist”

What CEO really means

I was the bottleneck and I knew it

But I just kept pushing it off.

(I was too busy to stop being busy)

Emergency after emergency….

At the time, I had my hand in all the jobs.

I was…

• Jumping on sales calls
• Meeting with our bookkeeper
• Updating our P&L and budget
• Reviewing email copy
• Monitoring the launches at 10pm
• Answering customer support tickets

… In addition to managing the team.

If I took a screenshot of my calendar at the time, it would look something like this:

And Rachel said “No” to Dinner in case you’re wondering 😢

It felt like I was both everywhere and nowhere all at once.

I was being spread thin and pulled in million different directions.

Something had to change…

Funny but true

But one day something clicked.

So when the team told me they needed a new copywriter.

Instead of doing what I always did, writing a job description for a copywriter.

I wrote one for a Recruiter instead.

(I was ready to hire 1 to hire 10)

Amateur CEO: Team says they’re burn out Throws up a mid job post saying they’re hiring Runs a gut-feel interview process Takes whoever accepts the job offer within budget Get frustrated when they’re surrounded by C players Experienced CEO: Anticipates team hiring needs based on Forecast Develops a multi-year recruitment strategy Creates a Copywriting worthy job posting Actively sources candidates (A Players aren’t job hunting) Screen applications and resumes Conduct initial phone/video screenings Administer assessments and tests Schedule in-person/virtual interviews Evaluate candidates and gather feedback Conduct reference checks Make a compelling job offer with 80%+ close rates Completes the onboarding process Surrounded by A and B players Professional CEO: Hires a recruiter to do all of the above Only interviews the top 3 candidates Team of A Players

She came in and immediately put in a professional recruiting process:

• Wrote a funny job posting
• Actively sourced candidates (’A’ Players aren’t job hunting)
• Screened and Interviewed Candidates
• Created a Compelling Job Offer that was accepted
• Completed the onboarding

The Change

BTW that “Copywriter” (Ilona) ended up becoming our COO 6 years later.

She is easily one of the most critical hires to AppSumo’s growth story.

This was a huge epiphany moment for me:

Ilona and team.

Of COURSE a focused specialist would outperform me.

If this was true for recruiting, why wouldn’t this be true for other departments?

After that – everything changed.

I was no longer involved in everything.

In fact – my job was to be involved in almost nothing.

I asked my team to take full ownership of their departments.

I would no longer be their safety net.

Before, they knew they could always rely on me to jump in and help out.

Now, I wanted them to fully own it:

“Olman, I need you to build out a sales team”

“Ilona, I need you to send me a “Full Send” ready emails”

“Nick, I need the Affiliate Program to bring in 8 figs next year”

Over time, my schedule started to free up:

Hopping on 10 sales calls/week became a 30-min check-in with Olman.

Writing copy for 5 hours became reviewing email results with Illona.

Doing customer support daily became seeing rising NPS scores via my CEO Dashboard.

As an individual contributor, you have tangible results.

“I closed this deal” or “I wrote this copy”.

But as the CEO, your output is now the team’s output.

My Team

As my team took more ownership, my calendar got increasingly empty.

If I took a screenshot of my Calendar at $50m, it would have looked something like below.

To the point where I questioned, “What exactly do I do here anymore?”.

My empty calendar

Before, when I went on vacation, I still lived in Slack and Email.

Now, when I went on vacation, no one was pinging me…

My phone was dry.

Instead of seeing it as a point of pride, I became insecure.

I even remember Noah Kagan asked me one time in a Board Meeting:

“You have a team and your calendar is empty… what exactly do you do here?”

This kept me up at night:

“Am I even needed anymore?”

The short answer: Yes, I was.

Most companies fall apart when the CEO steps away from the company to go “chill”.

What the CEO does now is create the frameworks so your leadership team can operate without you:

There are only 5 things a CEO can’t delegate: Vision (where you’re going) Culture (how you operate) Hiring Exec Team (who will build it) Allocation of Resources (how we spend our money) Cash (ensure survivability) If you feel overwhelmed as CEO, you’re doing too much Everything else (including managing of the team) can and should eventually be delegated. Understanding when and how to scale is crucial. I dive deeper into this in 14-Step Guide to Scaling Your Business.

For example, if you’re no longer involved in the hiring process…

How do you create the rubrics so your leaders can hire (as if you were in the room with them)?

At AppSumo, this was our hiring litmus test:

AppSumo Hiring Frameworks

Define the core values

• At AppSumo, ours were: hungry, humble, & weird.

Create hiring rubrics

• Does this person raise the average?
• Would I be afraid if they went to a competitor?
• Would I want to hang out with them if we were stuck on a 5-hour layover?

If someone doesn’t check those boxes, why are we moving forward with this hire?

The Process

One of the most dangerous quotes in business:
“Hire smart people and get out of their way”

If you dont create guardrails for your team to stay focused, it’s easy for them to get distracted

Listen to Will Ahmed (CEO of WHOOP) talk about scope creep:

One of the most dangerous quotes in business:
“Hire smart people and get out of their way”

If you dont create guardrails for your team to stay focused, it’s easy for them to get distracted

Listen to @willahmed (CEO of @WHOOP) talk about scope creep:pic.twitter.com/2TrA9yxyEB— Ayman Al-Abdullah 🧱 (@aymanalabdul) November 18, 2024

What was my process for creating these frameworks?

1. Identify your ideal outcome
2. How do we learn from our mistakes?
3. What has worked well for us in the past?

How We Create Frameworks

What is our ideal outcome?

Ex: For hiring, an A player who is fully onboarded and doing their job.

Historically, what has worked for us?

Ex: Internal referrals from our team who know our culture > putting out a job description on LinkedIn.

What mistakes have we made in the past?

Ex: Hiring based on title rather than need.

We need a really good email marketing manager -> We’re looking for someone to run our emails who is world-class at copy.

“But I can’t trust that my team will get the same results that I can!!”

Of course, they won’t.

They’re never going to get the results you need on Day 1.

CEO

Where most CEOs fail is in delegating the final draft rather than the rough draft.

Instead of saying, “Go write this piece of copy, it’s due on Friday at 5pm”

Say, “This email is going out on Friday…

Send me a rough draft by Monday so we can meet to review it”

Then, by the time it’s Friday, it’s 90% complete.

The best CEOs create checkpoints for their team.

Over time, the rough draft that started at 60% will be 80%, then 90%, and so on.

Soon enough, your team will be delivering work that’s BETTER than the work you could have ever done on your own.

In the beginning, you are the firefighter. But when you’re the CEO, your job is to Create the Fire Departments:

• Create guardrails
• Elevate the standards

This transition from $1M to $10M is where most CEOs struggle. I explore why in Why Most $1M CEOs Fail at $10M.

• Check in with your team regularly

Central Valley fire station

Your goal is to continuously build the systems in place in order to have an empty calendar

Week by week, quarter by quarter, you’ll create an unstoppable machine

Conclusion

Was this helpful?

Do you find yourself stressed and working too much?

I help 7-Figure Founders become $100m CEOs (by working less)

Bookmark this article.

Follow me on X / Twitter @aymanalabdul for more content like this!

THE END.

You see my 1:1 coaching business has a 2+ year waiting list.

I want to help more CEOs. So I looked into more ways I can scale myself.

So I launched a course.

I tried group coaching… and that wasn’t it.

You see, I think of myself like a conceriege medicine doctor for your business.

And I can’t both diagnose and fix 10 different problems in a Zoom Call.

The problem is that the CEOs were very happy with the program, NPS was high, and it was doing very well financially.

Me speaking

Doing what I love most

But then I discovered live workshops (and LOVED doing them).

The Collaboration

So when Codie Sanchez and I collaborated on a course early last year.

Collaborating with Codie

She asked if we should do a live workshop to help launch it in June.

Ya boi said Ab-So-Ruckin-Lootely.

People loved it so much that we sold out half the room to come back within 15 minutes

Someone said they spent over $100,000 on coaching and this was the best, most impactful thing they’ve ever done.

Thank you Spencer!

So Codie and I did it again

And people said it was EVEN BETTER than the last time

Me and Codie

Want to hear about the Next One?

Click here to get on the waitlist.

“Every year, I invite 100 of the most interesting people in the world to spend two days in my hometown of Victoria, Canada. It’s not a conference. I hate conferences. Conferences are usually about small talk and bragging at the bar. Listening to talks instead of talking. They favor the bold extroverts. The loudest person wins, and no attempt is made to facilitate conversation and friendship amongst the group. This event is different. It’s called Interesting People, and it’s happening on July 25 and 26th at The Fairmont Empress.”

Andrew is an entrepreneur, investor and billionaire**

I added the ** by billionaire because I think he might be a Canadian billionaire and thus only worth a mere $700M USD.

Andrew Wilkinson

Somehow I snuck an invite even though I’m clearly NOT a billionaire.

But to be honest… the morning of my flight – I almost didn’t go.

I was tired, just got back from a ton of travel, and honestly just wanted to chill at home for a week. I almost ate the cost of the flight and travel and stayed home instead.

But the morning of, I said F It, lets go. And I’m glad I did.

Here’s how it went.

Interesting People Event

I got to catch up with a bunch of old friends – and meet up with some new ones.

Shaan Puri, host of the My First Million podcast was there.

As were some other internet famous people, like Greg Isenberg.

We also got some productivity hacks from Sam Corcos, founder of Levels (Continous Glucose Monitor).

I was even asked to speak about “How To Grow a $100m Company”.

Me speaking on stage

The Next Morning

The next morning I got a surprise text from my good friend Nick Gray.

And as a reply, I obviously said “yes”.

I got to meet so many cool people and had a blast teaching my methodology – people seemed to like it too. Had a ton of people reach out after my talk.

Group photo

Additionally, Andrewand I got to geek out about business, tactical stuff, and life in his beautiful waterfront home.

Me and Andrew Wilkinson

Heading Home

On the flight back from Victoria, I reflected.

I wasn’t even supposed to be here.

Instead it was one of the most impactful events I’ve ever been to.

It was a reminder to me…

As the former CEO of AppSumo, where I helped grow the company from $3M to $80M in revenue, I've learned invaluable lessons about what it takes to build successful businesses in today's rapidly changing landscape.

In this podcast, I share my framework for helping companies reach $100M in revenue, why understanding your core value proposition matters more than chasing trends, and how to think about AI adoption in your business.

We explore everything from the death of SEO to why some companies are still crushing it at trade shows, and what it means to truly know your strengths as a leader.

Video

Watch my guesting here

Transcript

Neville Medhora: Joining us today on the pod, Ayman Al-Abdullah. Welcome, man.

Ayman Al-Abdullah: What's up, Neville?

Neville Medhora: Thanks for joining. So quick intro about Ayman. Ayman was the CEO of AppSumo and he got it on track from doing 3 million a year to $80 million a year. Great tag lab, by the way. That's pretty awesome. He became a meme lord for a while and then started Agoge. Consulting is doing great, getting CEOs as clients, killing it with that. And I would love to learn a little bit more about it. So welcome to the pod, man.

Ayman Al-Abdullah: Oh man, Neville.

Neville Medhora: Yeah. So let's talk about this first. You had this pretty sweet gig at AppSumo. You did really, really good with it, but then you moved on to like start your own consulting practice. What was that transition? What was that about?

Ayman Al-Abdullah: So I'd always say there's three phases of a company's growth. There's the startup phase, scale up phase, and the grow up phase. So startup typically gets you to around $5 million in revenue. That's really around product market fit. Scale up phase is around company creation. So it's really around taking the team, getting things out of the founder's hands and then grow up is really around protecting the legacy that you've built. I'm terrible at the startup. I hate to grow up and I love the scale up. And I found myself coming in at AppSumo, had already found product market fit was already a really great brand. Noah done an amazing job getting it to that next level. Anton had famously taken it over and it was very easy for me to plug in and immediately have something that I could now inject with the company creation, the stuff that I get excited about. So when I was able to take AppSumo from 3 to 80, I found myself as we're approaching $100 million in revenue, starting to creep into grow up mode. And I'm starting to realize like, hey Noah, we're rapidly growing. We're at that point, we're doubling year over year and I'm like, it's probably time for us to look for a CEO because to me, I think a CEO is perfect at each stage of the individual startup. But I found myself being less excited and less really the right fit for the next phase of the company's growth.

Neville Medhora: So I mean, that takes a lot of it because you had a pretty sweet gig and you weren't like fired by any means. I think it was like the opposite of like they wanted you to stay on.

Ayman Al-Abdullah: Yeah.

Neville Medhora: And you left and a lot of us were like, what the hell's going on in his life that he would leave this sweet gig? And I actually - and in retrospect, I've talked to a lot of CEOs who moved that phase. A couple people we mutually know have left their companies because they got so big, and they're just like, I'm not the guy for this.

Ayman Al-Abdullah: That's right.

Neville Medhora: To manage 400 people is a different thing than managing a small, ragtag team.

Ayman Al-Abdullah: That's right.

Neville Medhora: And so how did you know that? Were you just, like, finding the work less enjoyable and you're like, I know where this is headed. I can see the future and this is not going to be good. Is that the case, or did you know this from before that, like, I had these three phases and I'm good at this one?

Ayman Al-Abdullah: Yeah. So the analogy that I use is it's kind of like a sports analogy. In the beginning, the founder is the star player jumping for the ball in every game, playing 42 minutes, the spotlight is on them. Eventually you move into player coach, where you have a small team, but you're still doing a lot of the work, but you're coaching up that small team. If you really want to get to beyond 5 million, 10 million, you kind of have to put the ball down and assemble a solid team. So that's when you become the coach. That's really where I enjoy is that coach, the sideline, the person that's not on the court, but rather there with a clipboard and really assembling the best team possible. As we start to approach $50 million in revenue, you now have to move into the owner's box. And it's really a much more political game where everything you're saying is it's a game of telephones, four or five things removed. And it's almost like you're a mini politician of a mini city. And it's completely different dynamic. And some people are excellent at this. Me personally, I enjoy being a little closer. I like being on the ground floor. And I found myself, if I stayed there, I would essentially be holding the company back.

Neville Medhora: Huh. And so I assume in your own life you were probably like, I'm relatively financially set for a while and I'm just going to go start my own thing, or what were you thinking? Yeah, I remember you ended up starting, like, a consulting company.

Ayman Al-Abdullah: Yeah.

Neville Medhora: Did that come out of people just asking you a lot of questions? Is that how that came about?

Ayman Al-Abdullah: Well, no. I mean, the plan was sort of to, like, ride off in the sunset and sip mai tais on the beach. Right? I mean, yeah, at that point, I was like, oh, it's time to take a sabbatical. Enjoy the fruits of my labor. And, you know, obviously at the time, the market is doing well, crypto is doing well. And so, like, there's a lot of things that people were buying $400,000 NFTs at that time. So I was just like, look, let me just take some time off. But, you know, guys like us, we get bored quick. And I found myself being bored and going, well, what do I do next? And I open up my email inbox, and I had 400 emails from companies that were looking for their next CEO. And I personally was not ready to jump back into the trenches yet, but a couple of them were friends, so I'm like, I'll do a fun coffee with you. And so we met up for coffee and they were just asking me questions. And one of them was like, I've spent hundreds of thousands of dollars on coaching. This one hour has been more valuable than everything I've just spent. Like, whatever your rate is, let me know and I'll pay it. I'm like, I've never done coaching or consulting before. They're like, okay, well, here's what - I'm paying other people. I think I can pay you X. And I was like, all right, you know, you're a friend. Let's just start it. We started that engagement the very next week. He introduced me to three more people. Those three people introduced me and got to the point where my waiting list just started to grow from there.

Neville Medhora: Are we allowed to ask prices about this kind of stuff?

Ayman Al-Abdullah: Probably not, because it...

Neville Medhora: I hate saying my own prices publicly.

Ayman Al-Abdullah: So the issue is that I've raised my prices three times in the last two years. And so, like, the last thing I want to do is, like, communicate the price. And then someone's like, oh, well, that's the price. And it's like, I've since doubled it since then. So I will say, yeah, it's a pretty sizable investment.

Neville Medhora: Okay, interesting. I imagine the 5, 4, 5 figures.

Ayman Al-Abdullah: At least, not... Yeah, probably more so.

Neville Medhora: And then like, how - this is fascinating. I love it when something like this organically happens where you're like, I wasn't trying to start this. As so many people were saying, I'm going to give you money. That's right, that it starts. In fact, all my best products were usually like, hey, can you help me do this? Can you help me do this? And I'm like, what if I just made a product about this and helped a lot of people do it?

Ayman Al-Abdullah: That's right, yeah. It's like pretty simple, a hundred percent. I always tell founders, you know, you've hit product market fit when it feels like you're wearing a meat suit in a dog park. So like, if you are literally feeling like I am getting hounded by all these individuals asking me like, do you have this? Do you have this? There's probably a good signal to noise ratio there where you should probably do something.

Neville Medhora: Did you ever go down the route of I should record a course?

Ayman Al-Abdullah: No, no to me. Like I have, I've, I think I've bought well over a few dozen courses that just sit unused. And so I did not want to create something that no one was going to use. So founders, CEOs, they're busy, they just don't have time to do courses. They will have time to pick up a template. So my wiki famously has got like 2 million views on Twitter or X now free. It's a one click install and it immediately gives you a wiki for you to install into your business. You're not having to watch 12 hours of videos. It's a one click, it's done in less than 10 seconds. I would much rather have those quick winners than recording a course.

Neville Medhora: Also, it sounds like the problems that you're dealing with are not lending itself towards a course.

Ayman Al-Abdullah: No, 100%.

Neville Medhora: Like a CEO of a hundred million dollar company asking questions. There's too many vagaries right to be a course.

Ayman Al-Abdullah: Well, every single scenario. The reason I enjoy the one on one coaching, one on one consulting is different because I'll give you an example. When you're hiring a designer, a designer at AppSumo needs to ship fast, ship dirty and iterate over time. A designer at Apple needs it to be pixel perfect on day one. So I can't create a course of like, here's how to hire a great designer because that's dependent on the culture of the company. And so I have to first understand, well, is this company on track to IPO or exit? Does this company want to last for 100 years or are they looking to flip it in three years? And so depending on the nuances of the company, it's kind of like, yes, you could have a generic personal fitness program, but if you really want to take things to the next level, you probably need to get blood work done. You probably need to make sure that things are highly personalized to the individual in order to maximize the results for that particular person.

Neville Medhora: Okay, so what are you doing with these clients? Is this kind of like a weekly type of - I'm always just fascinated by this because here's the funny thing. You haven't actually created anything other than just like your knowledge. And you're selling that for a large amount of money. And for like a software company that sells something for 30 bucks a month, they would have to keep a customer for like 20 plus years to even equate to what like you charge a customer.

Ayman Al-Abdullah: So this, the most common is a monthly check in where we're doing like almost like a monthly board meeting where it's like here, what did you say you were going to do in the last month? What are you going to do in the next month? And so we'll typically have this monthly board check in where we're reviewing the previous month's financials, we're reviewing the previous projects, and we're seeing are we on track? Do we need to adjust the sales in order to ensure that we're heading in the right direction? Know oftentimes all it takes is a 3 or 4% shift to get from Boston to Bermuda. And so we're sort of adjusting those sales in between those. We're voice noting, we're checking in, we're texting, we're WhatsApping, hey, I've got a issue with X, Y and Z. We'll immediately jump on a quick phone call. And the way I like to think about it is like, I am your concierge medicine doctor for business. And so I become the first point of contact for a lot of these CEOs where it's like, hey, I'm dealing with X, Y and Z. It's like, let's go and address it.

Neville Medhora: Huh, Interesting. Okay, so they just get direct access to you. There's not like a super formalized product process or anything?

Ayman Al-Abdullah: Well, there is. So I basically walk the CEOs through a framework called the nine steps, the nine figures. Having seen over a thousand companies launch at AppSumo, and now having worked with dozens, close to over 100 CEOs, now I got to see the repeatable plateaus that plague most companies from getting to the next level. And so at each of these nine steps, we want to take the CEOs through this framework in order to ensure that we have these foundations in place. I literally just did a summit with Cody on Tuesday, Monday, Tuesday - Cody Sanchez, for those that are listening, where we walk through the nine steps, the nine figures, and we had individuals in the room that were doing 10, 20, $30 million in revenue going, yeah, I know these basics in the beginning. And by the end of day one, they're like, holy shit. I have been building this business on rocky foundation. No wonder my marketing is falling apart. My strategy is off. I'm churning and losing employees on a daily basis. It's because they had not set the foundation. I see this happen all the time where a company will drive to 10, $20 million in revenue on the back of the founder's hustle and then implode in on itself because the foundations weren't there.

Neville Medhora: Hmm, interesting. What about some of the technical skills that you've picked up since then? I was curious about this because, like, I always like learning new software. Like, I feel like I'm like a freelancer at heart. Like I'm learning how to do Figma and Framer right now and I'm like watching videos and stuff and it just like, I totally, I feel like it's like a hobby to learn new pieces of software for me.

Ayman Al-Abdullah: Yeah.

Neville Medhora: Are there any technical skills that you've picked up through this other like, I mean, like WhatsApp is not really a technical skill. Any software that you use to keep track of stuff or anything like that?

Ayman Al-Abdullah: I mean, the core is Notion. You know, I carved out a week to go through Thomas Frank's Notion course. Highly recommend all CEOs - to me, Notion is excellent because regardless of tool, whether you're using Loom, Google Drive, Figma, Notion has a really good integration where you can copy paste these links and pop it right in there. The search functionality in Notion is phenomenal. Have you ever tried to search on Google Drive? Like, how does a search company screw up search so badly? So Notion allows you to go like, well, where did I leave that exact comp spreadsheet? Where is the CEO handbook? Where did we leave onboarding? Boom. All of that is in Notion. That's why we've used the wiki. That's number one. Number two, 100% AI. Whether you're using ChatGPT, Claude, there's so many AI tools out there, you 100% need to be leveraging. If you're not using AI right now, it's the equivalent of being in the 90s, not using the Internet.

This approach to leveraging tools reminds me of patterns I share in My CEO Story.

So leveraging all these AI tools, in addition to that, there's a lot of these use case specific tools. So like I use Organimi for org charts. I use Loom videos. By the way, Loom just released AI SOPs. So you literally record a Loom video and then press SOP and it automatically creates an SOP that you can send to your VAs or your assistants. So all you have to do is record yourself doing things once. So 100%, I love leveraging - I mean obviously CEO of AppSumo, I love leveraging software. I think software enables individuals to take things to the next level. It's the modern toolkit for the CEO.

Neville Medhora: Yeah, it's like the modern being really strong and being able to dig the deepest ditch. Back in the day, that was valuable. Now you're just like, who has these skills? Yeah, anytime I meet like a designer or someone like that or a video editor, that's really good and you just look at the other work and you're like, whoa. You're just like, there's that, that, that, that's something, that's something.

Ayman Al-Abdullah: Well, like let's just use video editing as an example. Like everyone can use CapCut, but if you go like one level deeper and we're going to use Adobe After Effects, that probably requires 2x more effort, but the results are 100x. So like when I see a video that's using After Effects, it separates so much better than an individual that's just using CapCut captions. And so like yes, it required 2x more work to make that happen. But you look at the views and the views are 100x of that video. And so the effort was worth it. So I would much rather an individual, a designer, a CEO, your finance team, I love a use a tool called Fathom for finance financial analytics. I would much rather these individuals level up the tool sets, even if it requires a little bit more effort because the results that you get back are exponential.

Neville Medhora: I tell people all the time because we originally before copywriting course, I was teaching people how to freelance and I was always like, you got to become a triple threat. And that's a concept I first heard from Mark Andreessen, the famous venture capitalist, right? He's like going out with one skill into the workforce as like going to war with the butter knife and going out to the workforce with three skills that you're like roughly 70% good at. Like going out there with like full body armor and a gun, 1,000% and so, and so I always tell people. And the concept now has evolved into a certain. There's a term you're familiar with, Full stack.

Ayman Al-Abdullah: That's right.

Neville Medhora: Yeah, I love that concept.

Ayman Al-Abdullah: Yeah. I mean, let's just - let's just - you're a trunk fan.

Neville Medhora: Yeah.

Ayman Al-Abdullah: Okay. So copywriter, if he was just a copywriter, if he was just going out there and writing funny tweets, probably has a normal following. But he takes that and he stacks that with memes, he stacks that with business knowledge. All of a sudden, he's one of the most followed accounts on Twitter. Matt Gray was, for the longest time just posting out. Here's how I grew my social account. Then all of a sudden, he started doing these drawings. Now all of a sudden, his social account started taking things to the next level. And so to your point, social right now is like the equivalent of like the UFC when it first came out, where there's a lot of these one trick ponies, like, I know karate or I know kendo, and you - it's like, well, which style is the best? But then when you had someone that could combine styles, all of a sudden they were so dominant. They had a little bit of wrestling, a little bit of jiu jitsu, a little bit of boxing, and they just absolutely dominated the competition. And so you take a look at the world's best fighters today, it's these multidisciplinary fighters. The same thing is true in business. I think Elon Musk's wife famously said this, where it's like, Elon, if he was just a good business person would probably not be that interesting. But the fact that he's good at business, he's good at physics, he's good at visionary, he combines all additional skills is the reason he's now one of the richest people of all time.

Neville Medhora: So, so let's continue on that, that thread. I have a whole thing here about like, content marketing. Maybe we'll get into that right now. So it's like multidisciplinary content marketing. You said social media is like the early days of the UFC. Meaning you think it's just starting?

Ayman Al-Abdullah: Oh, it's a hundred percent.

Neville Medhora: Because when we were growing up, like, social media was a joke. That's right, Social media was funny. Like if someone had a Zanga or a MySpace or like posting on Facebook back in the day, you're like, oh God, dude, do something better with time.

Ayman Al-Abdullah: Right?

Neville Medhora: And now you're like, wait, this is like everyone's job now. Like CEOs are like required almost to be. They're like, you have to be like Brian Chesky. You have to be posting on Twitter all the time, posting on xyz. And so, so now you just see that as like a grownup thing. Is social media just part of everything now?

Ayman Al-Abdullah: Something really interesting has happened in the last 10 years where people are no longer following companies, they're following individuals. And so, like, the Joe Rogan's are now more valuable than all the media companies combined. The Oprahs of the world are now more valuable than all of the magazines combined. And so people don't want to follow companies, they want to follow individuals. And so it is impossible for you to be a $100 million CEO if you do not have a social presence. If Elon Musk texts the VP at another company, that VP immediately jumps on a call. If the CEO of Cisco, sorry, if you're listening to this, texts anybody, nobody's responding. If you do not have a social presence, you are not going to be able to attract top talent, close incredible deals, and really compete in this new market if you do not have a good social presence.

Neville Medhora: Yeah, I remember when he bought Twitter, people were like, why is he buying Twitter? And of course there's like the freedom of speech type of thing or whatever, that argument, but at the same time, it's like he was Tesla's biggest marketing channel, 1,000%. And Tesla makes hundreds of billions of dollars in revenue. And you're like, well, 44 billion compared to that. It's like. And he was going to get kicked off Twitter, by the way. That's the way it was going because Twitter hated him.

Ayman Al-Abdullah: Interesting.

Neville Medhora: And then the thing happened with Donald Trump etc. So he's just like, he must have been doing this calculation that I need to spend this money. It's like advertising money. Almost one. Yeah. To make sure I stay on this platform.

Ayman Al-Abdullah: I think Greg Eisenberg mentioned like the ATM framework. Meaning first one is attention, next is trust, then you get the money. And so the most important skill is the attention. If you're not getting attention, you can never translate that into trust. You can never - I mean even take a look at Liver King doesn't have, doesn't have any trust. But because he got the attention, he got the money. Right. And obviously that's short lived. But if you can combine all three together then 1000%, that's how you dominate. And so Elon Musk acquiring Twitter. Yes. He makes it seem like it's altruistic and oh, I'm doing this for free speech. That's bullshit. He 100% knew that this is a power play. He is literally buying the town square. And now he controls the algorithm, he controls what gets seen, he controls making sure that every tweet that he sends out gets the exposure that's necessary in order for him to move the markets and move the dynamic and ultimately make him richer.

nt. So I've noticed. Do you notice that with a lot of the CEO that you're seeing just like SEO, kind of like flounder but like social media just like massively go uphill?

Ayman Al-Abdullah: Yes to the first one? No to the second one. So 100% SEO. I believe the latest reports from Gartner is Google searches are down 33% year over year as a result of AI. And so Google results, period, are just cratering. And so if your business was built on top of SEO 100%, you're already seeing a 20 to 40% reduction in your revenue year over year. That's number one. Number two, Google just released three major updates this year that drastically changed the way they think about rankings. And so if you didn't get adjusted by just the pure volume of search, you may have gotten hit by the new algorithm changes. At its core, though, is are you only relying on one or two marketing channels? And so to your point, is social the thing that takes off? Maybe. For others it could be PPC. For others, it could be trade shows. For others it could be billboards. We were joking about that yesterday. So you have to figure out, well, what is the diversified revenue stream that allows me to ensure that if I have a 40% shift in one of my marketing channels, I could easily throw some more gasoline on the fire and ensure another social channel, another marketing channel, another way to acquire customers is able to take up that space?

Neville Medhora: Yeah. And it also, Sam Parr, one of our good buddies, he had a great quote and he said, if you're building your business on top of a social media channel, it's like renting an office space and a place where the rent goes up every 18 months.

Ayman Al-Abdullah: Oh, I love that.

Neville Medhora: And I was like, oh, that's pretty good. Also, you could just get banned from one of these things very quickly. I got kicked off Twitter one time for posting a photo, and it thought it was porn. It was like a picture of me and a buddy or something. And for some reason, it triggered a porn thing and we're like, what the hell happened?

Ayman Al-Abdullah: Wow.

Neville Medhora: And it kicked me off of Twitter for 12 hours.

Ayman Al-Abdullah: That's ridiculous. Because literally all my comments are filled with porn bots.

Neville Medhora: No, no, this is pre Elon taking over. And I remember thinking, I was just like, wow, all that work just down the drain for. And there's no one you can contact about this?

Ayman Al-Abdullah: No.

Neville Medhora: Like really nothing you can do? Maybe tell someone else to complain for you or something like that. But you - your stuff really quick. So being in front of all those other audiences, also behind the scenes, I work with a lot of companies and we do a lot of direct mail. So people are like, direct mail is coming back. And, you know, I'm just like, I don't think it went away.

Neville Medhora: Yeah, I don't think it ever went away. People aren't - people are more entranced by something like Instagram rather than like, hey, I got a piece of mail.

Ayman Al-Abdullah: That's right.

Neville Medhora: Yeah. So I do think there's a lot. When you said even trade shows, I see companies that they spend, you know, $100,000 on PPC and they spend $100,000 at a trade show and come back with all these, like, clients. Yeah. And you're just like, oh, this, this - the old school stuff of just getting in front of actual people is still quite powerful. If social media is not the only way to do it.

Ayman Al-Abdullah: Well, you have to start with, well, who's my ideal customer? Who's the buyer? Right. And if the buyers are going to the trade shows, you need to be at the trade shows, you know, and if your buyers are on social media, you need to be on social media. If you're marketing to plumbers, they're not looking at a reel on Instagram to choose their next service provider. Right. You gotta go where - you gotta meet them where they're at. And so oftentimes people think about the marketing channel first rather than thinking about who do they serve and who's actually the decision maker first. And then reverse engineer - where does that person live? Where are they making decisions? And how do I build a marketing engine that feeds directly into that customer persona rather than the other way around?

Neville Medhora: What do you think about podcasting? A lot of YouTubers are like, I'm quitting YouTube. And what they mean is, they're not quitting YouTube. They're quitting making, like, crazy videos every seven days. And what they're all saying at the end of the video is like, I think I'll just start a podcast. So, I mean, essentially what we're doing right now, you have, like, a conversation. Have you seen results off of these podcasts?

Ayman Al-Abdullah: Once again, it depends on your avatar. Right. For someone like Chris Do 1000%, it becomes one of his greatest feeders, because who are his customers? His customers are designers. And what are designers doing? They're consuming content on YouTube, on Spotify, and so it directly feeds and builds into his engine. If you are a roofing company, the last thing you need to be doing is starting a podcast, because homeowners are not listening to a podcast to hear about roofing insights. You 100% should be knocking on doors, putting up billboards figuring out how am I getting Google reviews. Your time is way better spent meeting your customers where they're at rather than trying to do what everyone else is doing.

Neville Medhora: All right, so let's go back to some of your CEO stuff. I find this fascinating because you're talking to all these different CEOs. I feel like you're uniquely positioned to see the future in some way. What industries are killing it? What industries are hurting? Do you see any like, overall trends of like what's doing well right now? I would assume, like AI stuff like that? Any like interesting insights you're seeing over there?

Ayman Al-Abdullah: I think first and foremost education's getting commoditized. I think people are not no longer paying for courses, communities, knowledge the way they used to because the quality of content now on YouTube for free in order to garner attention is significantly higher than it was. And so if you are building an education based business, it's 100% an uphill climb and a uphill battle. If you can instead take that knowledge and turn it into a template, tool or even piece of software that is 100% taking off. Number two, it is significantly harder to do business now than it was three years ago. For everybody. There's a lot more headwinds. We were joking around earlier. People were buying $400,000 NFT profile pics three years ago. It's a lot harder to acquire customers, acquire talent and really just be in business now than it was three years ago. We are 100% in economic winter. And I don't know if really any industry is spared. I think if anything, some industries may have taken longer to be impacted. You know, like commercial real estate was doing great when everyone else is falling apart. Now it's in the shitter. Government was doing great. Now things are getting tightened up. And so I think when you take a look back at 2008, almost every industry is getting impacted. It's just a matter of depending on when so what companies are doing well. The companies that are doing really well are ones that help other individuals make money. And so when you're thinking about how am I helping my customers acquire customers, how am I helping my customers save money, how am I helping my customers get things to the next level? If you can be directly tied to revenue, you will 100% be a lot more defensible. I think you and I were talking about this yesterday, which is, yeah, maybe email newsletters don't move the needle, but maybe what you're doing with the CRO stuff, 100%, we can tie that directly attributable to revenue. That's a much more defensible business because you can point to the dollars that you're contributing and it becomes much easier thing to justify on the P and L budget totally.

Neville Medhora: Every year I like to try some sort of little project. And this year I was trying something along those lines. And I used to be, I used to think that you just get this new idea and you try it and you do it. But of course it takes many iterations. And as we know, more and more successful people. I'm just like, wow, everyone has like, I guess what you call a pivot many, many different times before they really found the right thing. And so I was giving myself 6 months to 12 months to figure figure this out. And I started roughly around Q2, trying some things. And one of them was a newsletter agency like we talked about.

Ayman Al-Abdullah: Yeah.

Neville Medhora: And everyone's like, you need to start a newsletter agency. Newsletters are hot right now. Get people to do it. And we've had a couple clients that said, hey, can we start a newsletter? The problem is once you get over about 10 grand a month, they could just hire a really good writer to do it. And then the other thing is, we've actually gone in and trained some places to make newsletters. And you know what, it was really easy once we got them like the format to make the newsletter, they took over and made a pretty good newsletter every single time. And I'm like, they don't really need me or my company at all. They just needed the framework to get started. So it's like, okay, I can make a company starting newsletters, but that's, that's about it. And it's not really tied to revenue. Newsletters are not tied to revenue. Most places maybe AppSumo sends out an email every day, right? That's tied to revenue. But most places is just like, hey, it's like a bulletin update. That's it. Here's some cool stuff in our industry. Stay top of mind Cool. That's what a newsletter is. And I was like, oh, these are not tied to revenue. If I'm going to spend the next five years doing this, I think that's going to be a tough spot to be.

Ayman Al-Abdullah: That's smart. That's a smart insight because it's your point. It's either not revenue generating, which means it's not a priority, or it is revenue generating, which means they want to bring it in house. And so like you are always going to be living in that weird middle zone where I'm either not that valued or I'm going to be quickly replaced.

Neville Medhora: Yeah. And then with the AI stuff, you just kind of like, okay, where's the puck going to be this in five years? Right. ChatGPT is what, 1.6 years old? It's not even two. It's not even a toddler yet.

Ayman Al-Abdullah: Wow.

Neville Medhora: So, so let's say when it reaches five years old, is it going to be able to write an 80% good newsletter? I mean, the answer is, yeah, like, there's no data.

Ayman Al-Abdullah: Right.

Neville Medhora: And, and so you have to think like, okay, is that going to be a problem as well? And so I started going towards things that are like, just, can I prove my revenue on day one?

Ayman Al-Abdullah: Right.

Neville Medhora: And that, that's been like a, that's been my marker.

Ayman Al-Abdullah: That's awesome.

Neville Medhora: Speaking of this, whenever you see CEOs that have a business idea, do you ever talk about, like, their early life? Like, how long does it take people to find the right idea that took off? Do you know, do you have insights on that?

Ayman Al-Abdullah: No, I'm terrible at the beginning. So, yeah, I can't speak to that.

Neville Medhora: You have no idea. You're good at seeing an idea that's already taken off and people are clamoring to get in on it, and you're good at optimizing it.

Ayman Al-Abdullah: Well, the founder is a detective. Like, they're sniffing things out and they're going, well, where exactly is their revenue? I am - that is not my area of expertise and I do not want to speak on that because, yeah, I mean, quite frankly, I'm just terrible at it. So that's something that comes naturally to me. Whereas individuals like Noah, like Sam, they love taking things from 0 to 1. I think, like, Noah's got like a dozen companies that have gone from zero to seven figures because, like, he, like, that's built into his DNA. He literally launched Million Dollar Weekend, right? So, like, he loves that shit. Whereas myself, I'm like, hey, this has got a lot of potential. We could totally turn this into a hundred million dollars business. That's where I'm going to come in.

Neville Medhora: Where did you get that insight that you're - how do you know that about yourself so well?

Ayman Al-Abdullah: Well, there's an exercise I take my CEOs through, which is, let's go through the four or five moments in your life that you were most proud of, that even if you could tell no one else, you would still be proud of it. And those things tell me a little bit more about the core of who you are as a person. And so for me, when I look back at my life, the things I'm most proud of, obviously AppSumo, you know, coming in, I remember even jumping on a call with no, I'm like, I think this thing's got a lot of meat left on the bone. Hiring individuals like Alona that I knew had a ton of potential and seeing her rise from copywriter to now COO of AppSumo, I joined my fraternity when it was one of the worst on campus and when I graduated as one of the best. To me, the core thread amongst all of the moments that I was most proud of was unlocking untapped potential. And so what I love about what I do now is I can see I get to pick and choose who I get to work with. You know, I have - if I were to go sequentially through my waiting list, it would take over three years to reach the bottom. And so I get to pick and choose which companies. I'm like, this one's got potential. I want to work with this individual to take things to the next level. Because to me, that's what gets me most excited, is finding something that it's still rough and loose. It's got, you know, a little rough around the edges and really polishing and turning into that diamond in the rough.

Neville Medhora: Interesting. So taking stock of what you were most proud of kind of like.

Ayman Al-Abdullah: Just tells you about yourself 1,000%.

Neville Medhora: Yeah, well, because there are some transformations you see in public and it's - I don't even know this is a good example. But like you see someone like Mark Zuckerberg and this is like a, these are like once in a generation type thing. So to compare yourself to this is like insane. There's too many things, right? But you see like he became, he was like a just a kid programming and then he turned into a fast growing startup CEO and now he's, you know, the CEO of one of the largest companies on the planet. And these are totally different skill sets. I think you've seen this with like Warren Buffett too, just moving up through these ranks. Those are very, very unique cases where that person has adapted with each step. And you're saying like, I'm only good at this and I'm really good at this, so I'm not going to even try to get better at that. Yeah, to me that shows a strong amount of like just knowing yourself very, very well. Of like, I'm not good at that.

Ayman Al-Abdullah: Yeah.

Neville Medhora: And I do find that impressive.

Ayman Al-Abdullah: Well, I appreciate that. You're right. Like, who has really been able to navigate the multiple phases of taking the company from inception all the way to massive. It's like Mark Zuckerberg, Jeff Bezos, even Steve Jobs had to like get fired three times before he finally figured it out. Right. Bill Gates, like, look, I am nowhere near any of those guys. And so I have zero illusions to think that I can handle both starting a company, scaling company and taking it to IPO or that level. And so I'd much rather operate in my zone of genius, the things that get me most excited, rather than trying to learn all three phases of the company's growth.

Neville Medhora: That's pretty sick to know that about yourself. I don't know how to transfer this, so I'll do a Jerry Seinfeld. Like, what's the deal with AI? Now this is like you mentioned before that like not doing AI is kind of like back in the day of like, you know, the Internet's coming about and you're like, that stuff's stupid.

Ayman Al-Abdullah: Yeah.

Neville Medhora: I had a guy who was like a little bit of a mentor and he owned a big company called Golf Smith. I was introduced to him by a friend and he said at the time when I met him, their online retail was doing - their online retail was doing way bigger than their in person retail and had stores across the country. And he's just like, the way that that started was just someone in the company was just like, we gotta start a website. And this is at the time when like having a website was, it was like a novelty. People weren't really making a lot of money on the web. And then sure enough, over time that became their primary income source. And, and he was like, I was just so glad someone was doing it inside the company. What are you seeing people do with AI? Like any like interesting applications yet? Because we're still so early that a lot of the applications that you think are going to be cool are actually not that cool. But then there's other things that like, like Loom - you do an SOP and just writes it out. I don't think anyone thought about that in the beginning. No one thought that that was a thing.

Ayman Al-Abdullah: Right.

Neville Medhora: People thought like it would write your emails for you. It turns out like just writing your emails for you is not like the best use case of it, but it's other stuff.

Ayman Al-Abdullah: Well, I think we first have to understand AI. I think that oftentimes people are not true - it's really difficult for founders and CEOs to understand how their business plays into new disruptive technologies. I mean, we both grew up in the era of pre Internet, post Internet and we just saw how many companies were either blindsided by the Internet or leveraged it in order to take things to the next level. And this repeats itself over and over again in any new disruptive technology. And like one of my favorite is back in the 1900s when the Ford Model T came out. It came out, didn't even call it an automobile or a car. They called it a horseless carriage. They didn't even understand how to market this thing. And you know, Ford famously said if I asked my customers what they wanted, they would have asked for a faster horse. And at the time there was over 1800 cars, horseless carriage companies. Today there's just a handful. And so this disruptive technology that launched over a hundred years ago has completely transformed the way cities are completely transformed. I mean, how many industries are built on the back of automobiles? Additionally, how many industries have gone through recessions as a result of that? Like back in the day, everyone had horses. The horse industry went through a 40 year recession after the horseless carriage automobile industry came out. But what people don't realize is the horse industry is bigger today than it was in the 1900s. Really huge Kentucky Derby, million dollar horses. It's a luxury brand now. Think about the companies that were making saddles back then. Most of them were blindsided. Who survived? Those that transitioned to making leather interiors for vehicles. And so understanding how is my company going to evolve with this new disruptive technology? It starts with number one, what are my unique assets? Number two, what is the job that I do? And so when Loom thought about, what is the - why do someone record a Loom? I'm recording a Loom so I can show someone else asynchronously how I do something or share with them information. And so instead of going, how do we leverage AI? You have to first ask, what is the job I do for my customers? And then could AI make this better? And so instead of thinking about the technology, think about the problem that you solve and then ask yourself, could AI make this better?

Neville Medhora: That's a great framework of looking at it because it just seems like I've seen a lot of product launches with AI and you're just like, well that's stupid. They're just trying to shove AI so in their next product update, they can be like, we have AI but they're not there yet. I feel for them.

Ayman Al-Abdullah: Yeah.

Neville Medhora: Because I'm sure at the top there, there's probably some CEO that's like, I can't even follow all this stuff.

Ayman Al-Abdullah: Totally.

Neville Medhora: And everyone's coming like we need AI and they're just like, just shove some shit out there and see what happens.

Ayman Al-Abdullah: Right.

Neville Medhora: But also, you know what's hopeful about that? For a lot of big companies, we witnessed this with the web. A lot of companies had strong fundamentals. They did a good job by their customers. They weren't using the web and they were a little late to the web maybe. But at the same time they waited until the web made sense for them. Right. So even a lot of B2B companies now, they don't sell their products on the web. Like if you're buying like optical routers and stuff like that for AT&T, for like large scale deployment, you can't just buy one on the web. You have to talk to a company and there's a whole process in it to see which one's the right one.

Ayman Al-Abdullah: Right.

Neville Medhora: So like those places saying like they missed out on E-commerce, you're like, well not really. In fact, they're still not doing E-commerce the same way. But there are companies like apparel, all that kind of stuff. Like if you're like Express for men, you're not selling online. Yeah, you're going to get screwed. So I do have hope that like even a lot of companies that are late to it, meaning like, you know, the stuff all just came out like two years ago.

Ayman Al-Abdullah: Yeah.

Neville Medhora: They're still not that late, which is kind of interesting.

Ayman Al-Abdullah: I think the companies that have the fundamentals, we were talking about the fundamentals. To me, the very first steps of any 100 million dollar company is three things. Persona, problem, promotion. Persona is who do you sell? Your problem is what problem do you solve for them? And then promotion is how do I get customers and acquire them profitably and scalably. And I'm reminded of a train company in the 1800s who they served was business travelers doing interstate commerce. And they were helping them go from one state to the other and essentially do business in between states. That's who they served. Business travelers. When they asked them their problem and they were solving it by running this train company, they said it's really difficult for us to transact from one state to the next because monetary - there wasn't a Federal Reserve, there wasn't a centralized way to transfer money. Some people were like, this looks counterfeit. It was a lot of back and forth. There's a lot of pain using money. And so this company was like, if we help business travelers do interstate commerce, we should probably help them solve this problem. And so what do they do? They roll out something called the traveler's check. So this train company solved the interstate commerce problem for their customer by rolling out travelers checks. That company, American Express, 1800s to this day, what are they doing? They're helping business travelers do interstate or international travel. It's the same customer, same problem, different technology. And so if you want to be a timeless company, company that lasts centuries, you have to think about those core things and ask yourself, how can I evolve regardless of what the technology is? Because products decay. But problems are timeless.

Neville Medhora: Great quote. Nice. I'm seeing a lot of programmers now get really excited about AI and the way they're going about it is maybe a little bit different. This is like, for you, as a business person approach it almost a different way than the programmer. The programmers is like, I'm going to make 25 companies in 25 days, right? I'm going to apply AI to this problem, AI to that problem. I'm going to copy that company, but put AI in it. And 95% of them just don't work out at all. Like, they just don't get traction. Probably because of this. They're not actually solving any problem.

Ayman Al-Abdullah: That's right. It's spaghetti on the wall.

Neville Medhora: Yeah. So someone who's a programmer, and by the way, I categorize myself as this type of person, I'm like, let's put a landing page out. That's my version of it. Let's put a landing page out. See, we can get customers and see what happens. And you're like, no one signed up. Okay, figures. Yeah, it's a bad idea. Kill it, move on to the next one. But they're doing like a lot of these experiments. And one, a smart program I talked to, he was like, the way I think of it is like, the AI is going to get more and more powerful. So when the next GPT, 5, 6, 7, 12 down the line, whatever comes out, will my product be better? That, that's the way they're thinking about it.

Ayman Al-Abdullah: So.

Neville Medhora: But I do like your way of just like, what are the end problems? And could AI help? Maybe not. Yeah, maybe not in certain places.

Ayman Al-Abdullah: I mean, the person who's most famously using AI right now to make a ton of money is Levels, Right, Peter? Levels. So when you look at him, he's almost always thinking about what is the problem to be solved, right. For him it's like, oh, individuals don't want to drop $30,000 for interior design. So could I use AI to create an interior design app? I don't want to spend a thousand dollars for headshots. Could I use AI to create more professional looking headshots? And so start with, what problems do my potential customers have? And could I leverage AI in order to solve it rather than, hey, how do I just slam AI into everything, every potential idea and hope one of them sticks?

Neville Medhora: Yeah, I mean, we've been seeing - so I run a copywriting company, right? So everyone always ask me is like, did ChatGPT just wipe out your company? And the answer is no, I thought it would. Right? That's the funny thing. It's like we teach how to write now there's this thing that just writes for you. And here's the funny thing that happened about it. We lost some mid level customers, right? So a customer that's just trying to write like emails for a doctor's office to say, can you reschedule appointment? ChatGPT is really good at that. That's like low level writing. Mid level writing is like a blurb on a newsletter. Then high level writing is Mark Andreessen, Balaji Savasanan talking about their experience in the crypto market, where it's going to go. That's difficult to replicate still. But the mid and low level stuff is relatively easy to replicate with ChatGPT in future versions of it. And so what we realized was we're like, how come it hasn't gone down? What, like, what happened there? And the reason is office hours. Every time we come to office hours, I talk to people about their problems. Most of them aren't saying, here's a long passage, can you update my text? They're all saying like, I have a page, it's not converting. Why? And we go, well, what if you put that up there? Like that one headline is just not clear about what you do? And then I'm like, what do you do? And they have a tough time getting it. So I pull it out of them. And then they're like, oh yeah, that sounds so much clearer.

Ayman Al-Abdullah: Wow.

Neville Medhora: Right? So it's not necessarily just the copywriting part. It's a - it's overall like we're talking about the other day. It's overall like CRO.

Ayman Al-Abdullah: That's right.

Neville Medhora: Conversion rate optimization. And what I realized, like, over time is like, people don't really care about the copywriting aspect of it or the design aspect. They just want that end result.

Ayman Al-Abdullah: That's right.

Neville Medhora: So I have always had a hard time showcasing our results visually. Because if I show you an email that did well in an email that didn't do well visually, zoomed out, they both look the same. Like, there's no - you can't really tell. And if you zoom in on specific passages, people are like, okay, whatever. Like, it's not fun to look at.

Ayman Al-Abdullah: No.

Neville Medhora: If you show someone like this logo versus another logo and be like, this one performed 20% better, they don't care about what it looked like. They just care about that 20%.

Ayman Al-Abdullah: That's right.

Neville Medhora: And I remember thinking like, oh, they care about the end conversion rate, the method I use to make it better. They don't give a - wow. They honestly don't care.

Ayman Al-Abdullah: Yeah.

Neville Medhora: The CEO, if they're like, this performs 20% better. We get 20% more leads, 200% more leads. That's all. They want to know what you did. Honestly, they don't care at all.

Ayman Al-Abdullah: Wow.

Neville Medhora: And so I was like, oh, that's my business. It's not necessarily just copyright.

Ayman Al-Abdullah: Totally. Yeah. It could be a color on the button. All they care about is that result.

Neville Medhora: Yeah. Oftentimes it's a combo of all the above.

Ayman Al-Abdullah: Totally.

Neville Medhora: It's a combo of like, what are you actually offering, who's the product and are you speaking to them? It's a combo of all those things. It's like multidisciplinary. Once again, full stack.

Ayman Al-Abdullah: That's right.

Neville Medhora: All those different things put together and then - but the other thing is copywriting with the foot in the door.

Ayman Al-Abdullah: That's right.

Neville Medhora: Because when I say, like, we'll improve your conversions, you're like, you know, dime a dozen. When you say copywriting, people go, oh, I wonder if that could help. But what we actually deliver to them is actually better design, better layout, UX, all that kind of stuff.

Ayman Al-Abdullah: That's right. And you're a genius of that. Like, you are really good at going, well, what exactly are trying to say here? How do we properly message this in a way that's effective? How do we ensure that we're tweaking the - the overall layout of the page in order to drive that conversion? And like, I've seen you do this multiple times at AppSumo, where you're like, hey, let's update this headline. Let's move this around. Let's make this image different. Let's change things. This feels not clear and like that - just natural and intuitive to you because of how much experience - you've been doing this for over a decade. You have such good experience across industries that you're able to do things where if someone's working on one business with one product line, they're so deep in the weeds, it's really hard for them to know how, like how a stranger would look at it, where you're able to provide that outside perspective and immediately have an uplift on their conversion.

Neville Medhora: Yeah, you probably experienced this with your CEOs. It's called familiarity blindness.

Ayman Al-Abdullah: That's right.

Neville Medhora: Whenever you're inside something, day after day, week after week after hour, hour, having meeting after meeting about something, honestly, you can't make any more changes to it.

Ayman Al-Abdullah: Right.

Neville Medhora: And so actually, for - for all my consulting, by the way, I tell people I'm like, I am not - I will look at your page before so I can get a gist of it. So you're not watching me read. But at the same time, I'm going to just do a once, but I can't look at it continuously or give you feedback beforehand before we get on the call. And the reason is I will get familiarity blindness with it and I'm being paid to look at it. So it's already coming in a different context. And so one of the best things we do is like, we have other people look at people's copy and like someone who's not even a copywriter can be like, I don't understand what that means. And you're like, and yeah, there's a problem with that headline.

Ayman Al-Abdullah: Right.

Neville Medhora: It's pretty cool. So familiar - bonus. Getting out of that. Anyways, man, this is a fantastic interview. Where can people - where can people find you? Follow you?

Ayman Al-Abdullah: Yeah, probably on Twitter, X whatever it's called today. It's probably the easiest way. Probably join my newsletter. I actually walk through the nine steps, nine figures in a monthly newsletter. So we're not throwing too many emails at you. And so each month you can be like, oh, I'm working on Persona, or I'm working on promotion, or I'm working on process. And so every month, sort of like a little nice little reminder of what should I be working on this?

Neville Medhora: I need to sign that up.

Ayman Al-Abdullah: Yeah, I have a -

Neville Medhora: Special email address that's a newsletter reader and I built a tool so I can read newsletters, like an RSS feed.

Ayman Al-Abdullah: Nice.

Neville Medhora: I want to see that. What's the website?

Ayman Al-Abdullah: It's just my name AymanAlAbdullah.com. Nice. Yeah, thanks so much, man.

Neville Medhora: This is awesome.

Ayman Al-Abdullah: Absolutely sweet.

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• Use a windows 10 activation method that works offline by creating a local KMS server.
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Activation Method — Requires Internet? — Requires Product Key? — Notes

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Pre-activated Windows Versions — No — No — May have legal risks

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"Always be cautious when using third-party activation tools and ensure you have good antivirus protection."

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Trial Versions — Free — Yes — Legal

KMSpico and Similar Tools — Free — No — Not Legal

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Recently, I had the pleasure of sitting down with Chris Do on the Futur Podcast to reveal the strategies that helped us dramatically increase customer lifetime value and skyrocket our revenue.

In our conversation, Chris and I debunked this common myth and explained why a laser-focused approach to serving specific customers will outperform trying to reach everyone, every time.

I shared real-world examples from my AppSumo journey, pulling back the curtain on how data-driven decisions and absolute clarity about who we were serving transformed our business.

We also explored why companies like Apple deliberately focus on creatives rather than trying to appeal to everyone, and how this principle can apply to businesses of any size.

Video

Watch the full video on YouTube by clicking here.

Or watch the video below:

Serve One, Not All: The Key to Big Profits

Full Transcript

Ayman Al-Abdullah: If I go to your website and you’re like, I’m a designer, it’s like, okay, maybe. Maybe I like some of your designs. Whereas if I go to your website and you’re like, I only design homepages for SaaS platforms doing north of seven figures, all of your examples, your portfolio, everything related to that is deeply aligned to the one thing that you’re best at. Now, all of a sudden, when I go to your website, I’m like, this is exactly who I need to hire.

Chris Do: Let me just clarify a couple of things. Person, problem, promotion person. Is that you?

Ayman Al-Abdullah: No, that’s your ideal client.

Chris Do: Oh, okay.

Ayman Al-Abdullah: Yeah.

Chris Do: All right. Tell me more then, I think.

Ayman Al-Abdullah: You have to start with: Who am I? Who am I serving?

Chris Do: Okay.

Ayman Al-Abdullah: I think the best entrepreneurs, the best creatives, they deeply understand their audience. They deeply understand who they serve. I think that a lot of times, if you don’t have this foundation, it will crumble as you scale your business. Because building a business without an ideal client in mind is like writing a love letter and addressing it to whom it may concern. Imagine that you wrote a love letter to your wife, and at the top it said, to whom it may concern; she would throw it out, and you’d never get married, versus writing a love letter to that individual. Everything you do, every piece of marketing that you roll out, every piece of product, every strategy is directly tied to that individual. And I’ll give you an example, Chris, at AppSumo, we were serving everybody when I joined. We were doing Udemy courses, we were doing SaaS tools, we were doing fonts and icons. So, we’re serving designers, we’re serving solopreneurs. And so I took a step back and I analyzed the data. I’m like, look, who is actually… Who loves us the most? Who do we love to serve? Who’s our most profitable customer? And that’s the key phrase: Who’s the most profitable customer? And most profitable is the person who sings our praises, isn’t a pain in the ass to work with, and continues to buy from us. And what we realized is there was one individual, marketing agency Matt Alliteration. I’m a huge fan. Marketing agency Matt was buying from us at almost a 10x rate of everyone else. And it’s because marketing agency Matt was buying licenses on behalf of his clients, versus the solopreneur, who was buying one license. So when we doubled down on marketing agency Matt, our marketing changed, our strategy changed, our product, everything changed. So now, instead of you can only buy one license of this tool, you’re buying 10. Instead of having no marketing agency focus for Easter, now we’re rolling out white labeling, we’re rolling out the ability to have multiple seats. So we’re doing all of these things with marketing agency Matt in mind.

I discuss the importance of focus in building teams in My 4-Question Test for Hiring.

That one decision alone, changing who we’re serving, directly led to us tripling our customer lifetime value, which then allowed us to triple our revenue as a result. So it has to start with who do I serve? Because from who you serve, which is the most profitable customer, your customer lifetime value increases, which makes your customer acquisition costs so much easier. It makes the ability to think about strategy and marketing easier. So, person, then the problem, then promotion.

Chris Do: Okay, some things to get through here. Do you credit your analytical accounting mind to comb through data and try to look for the needle in the haystack to find your most profitable customer? Did it become apparent that somebody looks at them like, dude, what are we doing?

Ayman Al-Abdullah: Yeah, I mean, I definitely have that data-driven mind. But at that time, I had a great team. You know, they’re the ones that are asking questions on my behalf. They’re able to go deeper and ask, who should we be going after? How do we get better at marketing? And so the ability to have a team that has higher standards than yourself, I think, is really critical. At that stage, when we were doing around $10 million in revenue, in order to figure out, hey, let’s dig into the data, let’s be a little bit more data-driven, but not too much. I see a lot of people get hamstrung, and they almost paralyze themselves with data. They get analysis paralysis. But I think that if you can get 70% accurate, you can make a decision and move forward in a way that has a lot more clarity and gives clarity to the team. I say all the time, a CEO can be uncertain, but they can't be unclear. I share more about CEO clarity in My CEO Story.. And so, make a decision and move forward, and you’re going to have much better clarity for your entire company in order to say, hey, this is who we serve. How does this serve marketing agency Matt? They’re using the lens of that with product decisions, marketing decisions. Everything goes through the lens of how does this serve marketing agency Matt? I think Amazon famously leaves a seat open at every meeting for their customer. How does this serve our customer? And I think the best companies in the world deeply understand that. And the worst companies in the world, the Kodaks, the ones that fell from their graces, it’s because they ignored and forgot who they actually served.

Chris Do: Okay. The problem with the person is it’s not easy to see. It’s not easy to commit to.

Ayman Al-Abdullah: Yeah.

Chris Do: And it’s one of the biggest challenges that people have, because the logic goes, if I narrow who I target, then aren’t I leaving a lot of opportunity on the table?

Ayman Al-Abdullah: Yeah.

Chris Do: To which you respond with, we were…

Ayman Al-Abdullah: Very worried about that, but what we realized is when we cut our target audience, we tripled our revenue.

Chris Do: Yeah.

Ayman Al-Abdullah: And the reason that that happens is it’s not that you’re ignoring solopreneur Sally, but by having that focus, you’re able to then deeply serve one individual, which allows you to increase your revenue. And as a subsequent side effect, solopreneur Sally is still served because now she’s getting better deals because we’re selling more, so we’re able to have better negotiating terms with our partners. And so the entire ecosystem benefits as a result. Apple, I mean, from the very beginning, Here’s to the Crazy Ones, right? The ones that are pushing the envelope, everything they do, every piece of equipment they roll out is to help creatives. And that doesn’t mean that I can’t do my accounting on a Mac. That doesn’t mean I can’t use my Mac for Chrome. But by them focusing on the creatives, those that are pushing the envelope, they end up serving everyone else. Now, they’re a $2 trillion company This principle of amplifying what works has been critical in my journey. I explore it in Amplify What Works., and with all their marketing, they’re basically just serving one type of customer.

Chris Do: Right. There’s something that I’m reminded of that Blair Enns says, which is the market is bigger than the target, and we worry that if we just go for the target, we lose out on all this. But in fact, when you’re super clear, you know how to write your love letter, and everything becomes clear. The messaging, the tactics, the strategy, the product mix, all that kind of stuff becomes super clear. You serve them really well. And then there’s actually… You hit all these other people around, which you said, like, solopreneur Sally.

Ayman Al-Abdullah: Yeah.

Chris Do: Still served and sold.

Ayman Al-Abdullah: Yeah. Well, let’s just use your designer example. If I go to your website and you’re like, I’m a designer, it’s like, okay, maybe. Maybe I like some of your designs. Whereas if I go to your website and you’re like, I only design homepages for SaaS platforms doing north of seven figures, now I’m like, this is exactly who I need to hire. All of your examples, your portfolio, everything related to that is deeply aligned to the one thing that you’re best at. Now, all of a sudden, when I go to your website, I’m like, this is exactly who I need to hire. And a lot of times people go, well, I want to serve everyone. I want to show my entire portfolio. I want to do, I do logos, and I do this, and I do that. And now people don’t want to hire mediocre. They want to hire the best, the best for what they can afford. And if you dilute yourself and say, I can do a little bit of everything, I’m going to go for the person that specializes. I’m going to go, who’s the best logo creator in the world? Who’s the best branding specialist in the world? Who’s the best YouTube thumbnail creator in the world? And the market is big enough that you can run a seven-figure business being hyper-targeted on one thing that you focus on. I mean, I think that Mr. Beast spends $20,000 per thumbnail. It’s like, there’s an opportunity regardless of what you want to focus on. And I think the key is just figuring out how do I get hyper-targeted on who I serve in a way that is going to serve them and allows me to grow my business by being hyper-targeted on the one person I serve.

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