Choose Your Own Adventure: the Big Bet we played at Wine List

Faced with no product-market fit, we had a couple of major plays during our time. This post details the background and decision-making behind one of those.

When I talk with early-stage, pre-PMF founders, I often talk about 'Big Bets'. Determining the order of magnitude for a Big Bet is a tricky task.

At Wine List, we introduced a "By The Glass" product iteration. This was, operationally and strategically, a substantially big bet.

Ultimately, it didn't save us. But I want to re-examine the decision to do that…