Only a few close friends and family know this, but in 2023, I was quite certain I was done with the venture and technology business. Despite our financial success, my first firm Notation did not survive. That doesn’t mean we abandoned it. My former partner and I still manage the funds there together and work closely with the founders we’ve backed, but we no longer make investments in new companies and the firm itself will eventually be no longer.
I won’t share all of the gory details, but suffice to say a combination of business partnership misalignments, running really hard in venture for almost a decade, fertility and marital issues, and the weird loneliness that many of us felt during Covid, had me feeling really low. Oddly enough, this was coming off a period where I experienced my first meaningful financial successes in my career, primarily from investments in our first two Notation funds. Unfortunately the money didn’t make the feeling inside feel any better.
For a culture that claims to celebrate failure, there sure is a lot of celebrating success, hero worship and humblebrags (see VC brags). Except for the occasional blog post discussing lessons learned from shutting down a startup, the reality is that the vast majority of the industry is scared to talk about failure. I think part of this comes from fear of making the next fundraise harder, both for founders and VCs, but I think it’s equal parts human nature – that no matter how many times someone tells you it’s ok, that failure is celebrated here, in the moment it feels shameful.
I’m resilient. My mother gave me this gift, and it was hardened through a number of formative experiences in my childhood, which I’ll write about in a future post. I had grown accustomed to pushing through low periods, performing reasonably well, and not thinking too hard about it. But in hindsight this period was different.
The problems I faced in 2023 weren’t necessarily bigger than others I’ve encountered before, but their resolutions were hazier, if not impossible. There wasn’t an easy fix to any of them. The decisions required in early-stage venture require extreme focus and clarity – a few decisions can make or break a fund. I was operating in a complete haze and I don’t think I fully realized it until several years later. The jury is still out for our third Notation fund, and there are some bright spots and founders, but I know for sure I was not at my best, both in how I made decisions and how I showed up for the people around me.
I convinced myself that I had made commitments to our LPs and founders, and quitting would be the ultimate failure and betrayal of trust. But in hindsight the real courageous act would have been to stop investing and return the money to our investors. To take a break. Perhaps that was the most consequential decision I got wrong in that period. I should have also shared my lows and my fears with more people that I trusted.
In the years since, I’ve made hard decisions to be granted the opportunity to start new chapters. Most importantly, my wife and I are happier than we’ve ever been in the 30 or so years since we’ve been together (yes we’ve been dating on and off since we were 12), and we have two gorgeous little kids now too. I’m building Asylum with new partners I am grateful to spend time with and learn from every day, a firm that I’m proud of, that I think can be great, and feels closer to who I am and where I am in life.
But the most important lessons from 2023 were the ones I learned about myself (as they often are). That resilience doesn’t always mean pushing through. That my mental state has real measured impact on the quality of my decisions. That we go through rough patches and need breaks. That life is streaky.
To anyone going through a low, there are lots of others experiencing different but similar lows, and that behind the humblebrags and ripping and killing it, there’s real insecurity and perhaps even worse, some really bad decisions.
Stay calm. Stay humble. Stay clear. Keep going, even if that means taking a breather, to ultimately go even further.
Much love.