There’s a question asked of investors which I’ve always struggled to answer. It’s the variation of “what’s your favorite investment?” Makes me twitchy (for reasons in that link). It’s such a common question, that I need a better answer than a scowl. But like all good answers, it couldn’t be forced or invented, it needed to be uncovered. And finally I know how to respond because three years into Homebrew, we’ve now seen a critical mass of founders hit a specific milestone in their development. And that phase is my “favorite.”

It’s when the founders realize they have something that’s scaling. That the startup is still hella fragile but they’re way past product<>market fit. That their future success is really going to depend on strength of team and culture, not just how much more work they can put on their own shoulders. That customers would be very disappointed if this startup wasn’t around. It’s when hiring accelerates. It’s when a CEO realizes this company may be their next 10 years. That the key insight was right. And it’s ok to walk the high wire tightrope with a mix of confidence, humility, enthusiasm and stress. To be yourself as a leader and to want to improve as one.

So far we tend to see this transformation roughly midway between an A Round and B Round (your specific results may vary). For me, as an investor, it’s a thrilling moment. Not because of being able to imagine an eventual financial success for the company – that comes way later – but because all startups begin with a vision in their head of what could be built. And we commit to helping the team create the best version of that company. So the inflection point where those dreams really start turning into code, into product, into headcount, into revenue, into momentum. THAT’S my favorite point. And so my “favorite” Homebrew investments tend to be whichever companies are at that moment of their growth.