The Dumbest Smartest Things I Ever Did

One of the dumbest smartest things I ever did was fly to San Francisco to exhibit at Startup Grind in 2019.

We had launched GrowthMentor a few months earlier and were pre-revenue. I had about $5K left in runway, which is a generous word for the last of my personal savings, and I spent all of it on that trip, on the gamble that we'd come home with funding.

The math was insane and I knew it. The booth cost more than my rent, the flights cost more than the booth, and I remember running the numbers on the plane and deciding not to run them again.

We came home with nothing.

Nobody wrote a check, and the process of trying to get one made me want to off myself. I'm built to talk to customers, not to pitch a room that's already checking its phone. Every conversation was about the size of the market instead of the people in it. I'd spend twenty minutes explaining why mentorship doesn't scale like SaaS, watch the interest drain out of someone's face, and then go do it again with the next person. Somewhere around day three I understood that even if the money showed up, I didn't want the job that came with it.

The next month, broke and two months behind on rent, I figured out monetisation. I pivoted GrowthMentor from a marketplace play to a membership play, and we've been bootstrapped and profitable ever since.

The membership model fixed the thing fundraising never could have. Revenue from month one, nobody to report to, and every decision measured against whether members renew instead of whether a story pitches well. Seven years later GrowthMentor is 750+ mentors and over 60,000 sessions booked, and there's still no investor on the cap table.

Sometimes your dumbest move is the one that corners you into your best one. I look at that photo now, hoodie and lanyard, grinning outside the venue, no idea that running out of money was about to be the most clarifying thing that ever happened to the business.