There's No Perfect Time to Bet on Yourself

Someone in a recent CEO roundtable asked me what made me the entrepreneur I am today, after building multiple hundred million dollar businesses. The honest answer isn't a strategy. It's a conversation I had with my wife.

I was 35, we'd just had our second kid, my wife wasn't working, and I wanted to leave a stable path to become a co-founder at a company that could pay me close to nothing. In this video I share what she said that changed everything: she gave me one year to prove it had legs, or I'd go get a real job. That was the gift, the gift of time, and the gift of a forcing function. There's no perfect time to bet on yourself. But if there's a problem you can't sleep until you solve, find a partner and a forcing function, and get moving.

⏱ TIMESTAMPS
(00:00) The question I got in a CEO roundtable
(00:53) From a $10M company to a $10B company
(01:16) Meeting the Terminus co-founders in 2015
(01:39) Pitching account-based advertising on a whiteboard
(02:19) "Why don't you become a co-founder?"
(02:43) Going home to tell my wife
(03:37) "Do you want to be an entrepreneur at 35 with two kids?"
(04:46) Why I couldn't say no to this problem
(05:23) The three things she did that became the inflection point
(06:00) The gift of time and the gift of a forcing function
(06:59) That day, I became an entrepreneur
(07:13) There's never a good time. The best time is now.
Give yourself the time you need. But create a forcing function that isn't forever.

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