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. 📌 Subscribe for daily GTM OS strategy and leadership frameworks Head to runongtmos.com for more