How to replace yourself as CEO…

A couple of weeks ago, I shared the story of how I wrote a GrowthAssistant thread on Twitter that went viral and led to 400+ leads in 24 hours. The thread took me < 30 mins to write and BOOM.

But here’s what happened next: Adriane had hundreds of people to call and after that, scores of new assistants to recruit… from a foreign country. At that point, we made maybe 15-20 placements TOTAL.

From that point on, we started making 25+ placements PER MONTH.


One challenge I've had as a bootstrapper is competing for talent w/ large cos that offer better benefits.

I use Rippling PEO to even the playing field by offering:

— Medical, vision, dental, and supplemental coverages (typically only available to big cos)

— FSA/HSA accounts to save employees money

— Medical concierge to answer employee health care questions

Rippling is payroll, benefits and more. (I used them long before they sponsored!)

Adriane had an unfair advantage. While it was overwhelming, she was like Tom Brady with 2 mins left in a game. She called a previous person who had worked for her.

She quickly found 2 sources in the Philippines and 2 recruiters. And she set up an interview process and an ATS (Applicant Tracking System).

I had written the thread and gotten the business but she actually threw the winning touchdown pass.

Adriane has a unique gift of being focused, hardworking, and matching the right talent to the right organizations. She’s a mix of rigor and nurture.

She originally wanted to start a daycare and I’m sure she would have brought those same skills to that venture!

I tell that story because it illustrates the hardest part about starting and running a business:

Being CEO. A big part of my job is finding the right CEOs.

I’ll walk you through what I look for, and what I think it takes to be a strong CEO. Then I’ll show you how to recruit CEOs.

Unfair advantage

I’ve Tweeted about one of the unfair advantages I had when launching Ampush, my digital media company.

When I left my job at Goldman Sachs, I got to keep my subscription to GLG, a service that let me call experts about anything I wanted to learn.

Through those calls, I uncovered a need: lead generation for online schools. That launched my business. The relationships I built helped fund that business.

Other examples from CEO's of Gateway X companies:

Adriane - Before launching GrowthAssistant, our outsourced marketing company, she had built massive recruiting machines for her first company, DRW Trading. She knew how to do this and I knew growth marketing.

Kasey - Before launching Aux Insights, our PE advisory company, she had done tons of M&A/Diligence in her previous role for digital marketing businesses. This complemented my Ampush experience + my network of PE.


Anyone who thinks they can start a company on their own doesn't need me and isn't interested in partnering with Gateway X. That's totally fine and actually works by design.

Someone who is eager to learn, wants feedback and to grow into the Founder/CEO role is a critical hiring criteria for me. I spend a ton of time directly coaching/teaching. I model behaviors, frameworks, and examples.

The person not only has to be hungry for that but actively soliciting it. It takes a lot of humility and ambition to have that level of coachability.

Importantly, I draw pretty strict lines around decision-making and ensure the CEO knows it’s their decision (and then back that up by not overriding it or "told you so"-ing them.)

Side note: If you don’t have a coach, I wrote about how to get one and work with them here.

My team and I are rigorous about our process. We use this evaluation form to guide us.


There's a famous value from Nike "your job is not done until THE job is done." I love that for ownership.

I tell every CEO partner of mine: if I'm on top of details that you are not, that is a big problem. I'm not day-to-day in the business. I have no reports. No specific operating responsibilities. So it’s a red flag for me if I'm spotting details they are not.

Ownership btw is way more than "do you take care of the job." To me, it also means:

  • Do you have high standards?

  • Do you want to win/hate losing?

  • Do you have high degrees of accountability?

  • Do you actively put me to work?

This has been one of the harder things to gauge and why we instituted an EIR program (more on that below).

Entrepreneurial Rigor

I said in a previous newsletter that this is the only trait I hire for.

My Ampush co-founder and BFF, Nick Shah, and I coined this term in 2017 when we did an internal culture reboot.

What we had observed over helping develop hundreds of people is GOOD people tended to either hustle – meaning they moved fast, were creative, resourceful etc. – OR they were rigorous – meaning they were logical, quantitative or reflective.

But GREAT people were always… BOTH.

At some point, most founders will want to replace themselves but they’ll struggle to do it well.

Here’s what I learned about attracting the right CEO.

1) I build relationships - my best partnerships have come from long-standing relationships. See my previous email about friendship. It matters!

2) I come with a compelling value prop - a) founder-level ownership, b) de-risked venture because I can bring customers/know-how, and c) MOST importantly, my WHY for doing this is to coach/care for my CEO partners. They are my customers and I'm here for their personal growth. The money is secondary (and follows).

3) I come with a big social following. That’s one of the benefits of this email and my social presence on Twitter/LI. I'm attracting a ton of folks. Even better, by making what I stand for clear (bootstrapping, cash flowing, long-term, personal growth), I tend to attract like-minded folks which narrows the funnel rapidly!

4) I have a 3-month entrepreneur in residence (EIR) program, where my team and I work directly on one or multiple ideas with the CEO/Founder. It’s hard to know if someone is the right hire through conversations. The EIR program tells us all we need to know. It answers EVERY question above.

Regardless of how well you lead as CEO or how strong the CEO you hire is, leading a company is full of challenges.

Andrew, who heads Bootstrapped Giants, was struggling to launch our podcast.

He called to tell me how guilty he felt about it because he’s been podcasting for over a decade. This should have been easy.

We talked and made a plan together, but before I ended the conversation I reminded him that after getting past this one we’ll have other challenges.

It’s part of the process.

What characteristics do you admire in good CEOs? Hit reply and tell me.

I'm constantly looking to improve my process.