The next chapter
I’m sitting here at home, as workmen overhead diligently tear the roof off of my apartment building. I’m not complaining; the roof is a couple decades old and occasionally leaks (something, I’ve been told, roofs shouldn’t do). And there are enough roofing supplies on the sidewalk, in the halls of the building, in the elevator that I’m reasonably confident that when this roof goes, a new one will take its place to battle the elements a few decades more.
It’s distracting, though. I’ve been writing this note in my head for weeks now, trying to find the words to sum up my feelings at the end of one phase of my life, and the beginning of the next.
At the end of the year I’ll be stepping down from my role at WIN, and in January I’ll begin a masters program in Sustainability Science at Columbia. I found out I got in last Wednesday, I decided to go two days later, and in the time since I’ve been taking comfort in the blitz of actions necessary to transplant oneself from one coast to another in a month. Activity’s easy. Quiet’s hard.
The goal here, the reason I’m doing this, is I’d like to take my lessons from venture and apply them to startups that through their actions support and grow global biodiversity. These challenges are urgent and I’ve seen companies that are starting (and underserved) now, so my hope is to raise and deploy a small venture fund concurrently with my studies. I’ll learn soon enough whether LPs (or professors) think that’s as great an idea as I do.
I wasn’t sure how I’d feel going through this transition, and like the best moments in life it’s been a potent mixture of joy and sadness. The prevailing sentiment, though, has just been gratitude.
My team at WIN has been literally family to me. This job is a strange, wonderful, chaotic one, and yet every week for eight years we’d be back in Los Gatos, talking, laughing, debating about lunch.
Dena I’ve known half my life, and has showed me so much about how executives actually function. She’s gone through much in these past couple years, and has consistently encouraged me to be bold with the time I have.
My first boss at WIN, Michael, left a few years back to start Spider Capital, but he had the unenviable task of managing me. He taught me — and sometimes had to teach me again — what being a good investor actually entailed.
Satra is our newest team member, but made our last CEO Summit so easy it was stressful. Community at WIN has been a passion of mine since the beginning, and it wasn’t always easy to articulate to someone like Maynard why throwing events was important. Satra — and the inimitable Heidi Burns before her — has defined and elevated how we serve our community so well it just makes me beam.
Jonathan is actually a genius (he’s going to hate me for writing this), and in our 1:1s this year he was singularly instrumental in helping me see my path forward. If you ever have the chance to have his mind trained on you and the challenges you’re working through, I highly recommend it.
My parents will revert to simply being parents, but working with the two of them (my dad as “Maynard,” my mom as “CFO”) has been such an unexpected blessing. I wrote more on this when we published Dear Founder, but I’m so glad I took the chance I was given. Explaining to your mom why it’s a great idea to put money into a sneaker marketplace is an experience I wish for anyone.
I need to specially highlight Jeremy, who’s been a peer, a mentor, a colleague, and above all a friend. He’s been with me since almost the beginning, and we’ve gone to countless demo days, borne witness to dozens of companies through time, and made plenty of silly side-bets along the way (most of which I’ve won, for whatever that’s worth). He’s quietly and unselfishly helped me too many times to count, and has put up with all-too-elaborate pranks. I’ve seen him grow into the leader he is now, and I can’t wait to see how WIN moves forward under his stewardship.
Our Affiliates always had to be nice, but they didn’t have to be kind. I will cherish getting to know them and seeing how they conducted themselves so far along in their careers, and am grateful for the time they took to mentor, advise, and just hang out. In some of the times when I felt most cynical, it helped to remember that their success didn’t come at the expense of character. They also tolerated the silly awards I insisted on making and presenting at events, when I’m positive they all had much better uses for that time.
One of the hardest things this past week has been emailing founders I’ve worked with about this news, because as much as we made bets on them, they made bets on us. It’s been such a privilege to see and occasionally help these entrepreneurs navigate their paths, and to have made some lifelong friends in the process. It’s working with them that has made me feel like maybe I could keep doing this investing thing long-term, and I’m touched by how supportive they’ve been. I know they’re in good hands with the rest of the WIN team.
All this is to say nothing of the other investors, friends, neighbors, family, and city I’m now saying bye to (for a couple years. It’s fine.). It’s an unfortunate thing that you just can’t see how deep a plant’s roots go until you pluck it out of the soil. I’m grateful.
And I’m excited. I have loved and been passionate about ecosystems and how they change with time since I was a kid, and I think establishing a new harmony between nature and man will be one of the most creative, fulfilling challenges of the coming century. As I thought about how I could do more, I kept coming back to venture. This transition will need entrepreneurs of all stripes, and I’d like to take anything I’ve learned to support them as best I can.
I’m told the re-roofing will be done by tomorrow. The noise and chaos will quickly be forgotten, and in its place will be something new.
I’m grateful.
