Why Can't Founders Replace Themselves?

There's a reason the only way to get the "Founder" job title is to start the company — because there's no way to hire for it otherwise.

When I was running my first company, I was in my mid-20s with a hilarious lack of experience. The company was growing quickly, and we went from "a few people in a room" to "a few hundred people in a room," and soon my lack of experience (and pimples) was becoming very evident.

I was scared, so I set out to find a replacement for me, someone who could not only bring more experience but more confidence to the staff in executive leadership. We found an "old guy" who, at the time, I think was maybe 38, probably less, but he had some gray hair and was orders of magnitude more mature than the lot of us.

Try #1: Can't Train Passion

My first replacement lasted less than six months. It didn't make any sense to me. He had the experience, he was smart, and he was disciplined - all things I was not. But it wasn't until the first time that I saw him extol the virtues of our startup to others I realized I had made a costly mistake.

During the client pitch for our ad agency, which I would normally give, he spouted facts, but none of them came with any passion. Imagine your favorite pitchperson (Steve Jobs or Sam Jackson) giving a pitch completely monotone — devoid of passion. That same tone came across in our staff meetings, where it was clear he understood the product and the company, but he had no true passion for it. To him, it was just a job.

That passion is something that Founders tend to have instinctively because, well, we built the friggin' thing! We automatically convert the pride of creation to the passion of pitching. Many of us have been doing it so long we don't even realize it, but getting a newbie to "fabricate" that passion and the emotion it inspires is damn near impossible for outsiders.

Try #2: It Helps to be Likable

So we went back to the well and found a second replacement. This time we found someone with a genuine passion for the company and the industry. We pulled a class amateur recruiting move — hiring for what that last person "wasn't" versus what we actually needed.

The next person was certainly passionate and capable, but as it turns out — kind of a douche. In meetings, he would get super fiery, but often at the expense of everyone else in the room, essentially talking down to them while extolling the virtues of our vision and opportunity. Shit.

That was the first time I experienced a "palace revolt" where the entire staff would come to me and say, "Please make him leave!" in much less kind words. That's when I realized that the people that we had hired had joined because somewhere in the interview process, they actually liked me. Hiring a new person who wasn't likable was me pretending that all of my relationships would just magically port over to anyone else who took my title.

Try #3: Incentives Don't Align

By the time we got to the third hire, about 2 years into this process, the team and I were exhausted. At this point, we needed someone who could share the passion but also connect with the troops. I recommended we hire my #2, who happened to be someone I trusted personally very much.

When they took the job, there was a sigh of relief in the company because everyone finally knew what they were getting. I thought I was done. For the next few months, things ran like clockwork, and I could finally see myself moving on to something new.

But then I started to notice a pattern. We were no longer taking risks. We weren't doing things "just because they should be done" versus "what makes the most sense in the P&L." I would come to realize that while our third attempt was certainly competent, their incentives were to hit revenue targets and manage headcount — not to build a "great company."

So much of what we do daily, from who we recruit to how we shape the product to the culture we create is done because our incentive personal incentive to simply build a great company is hard-wired into us. Those details, while sometimes minor from the outside, collectively are what make great companies.

It is easy to say that there are people with more experience or talent than we do, but we can't pretend they will ever fully replace the Founder. If we can accept those losses, we might be OK, but if we think we'll get a 1:1 replacement, we're kidding ourselves.

In Case You Missed It

Founders, Time is Your Greatest Asset (podcast) Thinking long-term is a total game-changer. It not only toughens you up, but it also attracts investors and partners who are in it for the long run, boosting your chances of scoring lasting success in the crazy world of startups.

The Goal is NOT to be a Startup Sure, Startups get more opportunities to grow and funding offers to expand. But you can’t stay in this phase forever.

What Happens After I've Made It? We always dream about our startups making it big. But what happens when they really do? What happens when all of the risks actually turn into the payouts we had always hoped for? Are we actually happier?