Replacing Oneself as CEO

I am very happy to announce that Fred McIntyre has joined awe.sm, the company I founded and have led for the last 4 years, as CEO (read more about it on TechCrunch). My new role is Head of Product Development in which I will continue to lead product, strategy, and engineering.

This is at once one of the hardest and best things I’ve ever done.

There’s a lot of great writing out there on hiring non-founder CEOs from a business perspective: if you don’t want to have to do it, do these things (I definitely didn’t do enough of them); if you think you might need to do it, think about these things; and if you’re going to do it, try to do it like this. So what I really want to talk about is the personal side of this process from my perspective as the founding CEO.

I wish I could say this was my idea, but frankly I wasn’t self-aware enough to come up with it. To be an entrepreneur I believe one must have a somewhat irrational belief in your own capabilities, otherwise you’d never be dumb enough to start a company. Regardless of any perceived glamor, most entrepreneurs I know will tell you that starting and running a company is fucking hard and there’s often more misery than joy. But there’s just something broken in us that makes the prospect of doing anything else seem even worse. For those of us with this particular defect, I think the Peace Corps slogan sums it up: entrepreneurship is “the toughest job you’ll ever love.” The thing in me that drove me to quit my job, move in with my parents, and start awe.sm is the same thing that kept me going through incredible stress and the lowest of lows to make it to our Series A and it’s the same thing that kept me from asking for the help it was clear to everyone around me that I needed.

I put hiring a CEO in the same category as taking an acqui-hire or just closing up shop and moving on — things I would think about at 4am in the office on those darkest nights when I’d have a bout of sobriety about the insanity I’d turned my life into. And ultimately, things that represented the one unacceptable option motivating me to push even further beyond my limits I’d long surpassed: failure. In the early days, the only way for me to keep awe.sm from failing was to tie my fate with the company’s. If awe.sm failed, I failed. But as we switched from lean startup to growth company, I didn’t fully realize how making my ego a shareholder went from being necessary for survival to being a limitation on what we could achieve.

Fortunately, I have an amazing Board that cares about me as a person as well as an investment. Mark, Ian, and Ryan took the time to help me see why something needed to change, and, to their great credit, gave me the decision of what to do. I will never forget the emotional tornado (roller-coaster doesn’t do it justice) of that day. After 3 and a half years of fusing my self-worth with the success of the company in the crucible of startup survival, it was impossible to tear them apart without pain. But while my first reaction was disappointment and failure, it was almost immediately washed away by a wave of relief. I knew everything they were saying was true, arguably better than they did, and I knew change was inevitable, but I had no idea how stressful and exhausting maintaining my internal reality distortion field had been until they gave me permission to turn it off.

The basic choice we had in front of us was to sell the company or hire a CEO. We had plenty of money in the bank, a great engineering team in an impossible hiring market, and real valuable hard-to-build technology, so we were in a better position for a sale than many acqui-hires. Personally, I still owned 30% of the company outright and selling would have kept me from having to give up the CEO role. On the flip-side, we would be starting from scratch on the CEO search and it would ultimately mean signing up for a Series B (i.e. more dilution) and several more years of awe.sm. The Board said they would support either decision, but only I could make it. Talk about a gut-check!

Guess which one I picked :-). It was far from an easy decision, I agonized over it for weeks and got advice from a lot of smart and experienced people (thanks everyone!). I made the choice and told the Board; they asked me if I was sure and I told them I was; I had second thoughts and talked about it with a bunch more people; the Board asked me again if I was sure, I said I wasn’t but I was committed. And all this was before we even started recruiting a CEO! I ran the search process, screened all the candidates, and ultimately had the final say on who we hired.

I chose not to sell because I believe the opportunity for awe.sm is too big to ignore, and I chose Fred because he shares that belief. When Fred accepted his offer, Mark Suster said that he thought this would be the best year of my career. I hope he’s right, but I’m at least certain it will be the best year of my life since starting the company.