Things I should have done sooner as a CEO:

  • 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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