The Sweet Sweet High of Your First Yes

I don’t have too many hard-and-fast rules about investors because tech changes too quickly for that, but conviction for me is certainly a must. Conviction is the opposite of “maybe”, the dreaded word that has tortured so many founders. Having conviction and ending up way wrong is so much cooler than equivocating to avoid embarrassment. It’s about swinging for the fences after all, and fuck yes or no is what pushes us all forward.

That first yes tho.

It’s the hardest one to get and perhaps the most satisfying. It’s the one that comes from someone that isn’t your mom or your rich cousin or your old boss. It’s that glimmer of validation that maybe what your working on MIGHT be a thing. To someone. Someday.

To create an entire fund around the first yes is a bold and challenging move, because you don’t have the safety net of “the numbers”. To be able to see potential in a group of two or three people who may not even have a product yet is a fun challenge and something I admire about everyone in the business of writing the first check.

When I first met Nick Chirls, I was struck by his conviction. He is passionate about tech and forward-thinking. I met Alex a bit later and he too has this same conviction. It’s quite rare. Nick was an investor in Grand St. via betaworks and recently left to start a new fund called Notation Capital. I have been working in tech for a while, and have spoken with hundreds of investors at all stages. They are the real deal.

I am super excited to be joining their efforts as a Part-Time Partner, along with John Lax and Alex Chung. I’ll be helping out from afar with Notation and feel really lucky to be part of this. I’m still at Etsy, working on something new for them and obsessing about marketplaces all day.

Over the past 10 years we have seen the success of incubators and accelerators, and what I like is that Nick and Alex are trying something different. It’s a new model and it’s intriguing. I can’t wait to see how it evolves.

While I am embarrassed to bring up Dumb & Dumber at a time like this (wait no actually I am not), I feel like this clip most accurately sums up my feelings on all of venture capital, startups, and fundraising in one neat clip.