When you’re surfing and get caught in the whitewater after a big wave, the feeling can be terrifying – you’re “caught on the inside.” I love this phrase because it conveys a feeling all humans have felt some version of: when things get a little intense, your body is burning oxygen, and you lose track of which way is up. This is how I’ve begun to reflect on my time this summer while attempting to launch my own VC fund: staring down the barrel of the gun of raising 7 or 8 figures of other people’s money became a bit overwhelming, if not intimidating.
I found myself procrastinating by spending a lot of time writing code with the help of AI. And eventually I realized that maybe I should be riding this wave myself, not as an investor, but as a builder.
*My git contributions have benefite…
When you’re surfing and get caught in the whitewater after a big wave, the feeling can be terrifying – you’re “caught on the inside.” I love this phrase because it conveys a feeling all humans have felt some version of: when things get a little intense, your body is burning oxygen, and you lose track of which way is up. This is how I’ve begun to reflect on my time this summer while attempting to launch my own VC fund: staring down the barrel of the gun of raising 7 or 8 figures of other people’s money became a bit overwhelming, if not intimidating.
I found myself procrastinating by spending a lot of time writing code with the help of AI. And eventually I realized that maybe I should be riding this wave myself, not as an investor, but as a builder.
My git contributions have benefited significantly from AI
If you’ve followed my career at all, you’ll know I’ve always been a builder at heart, and the more time I spent organizing the preliminary work for a fund, the clearer that vein of my identity became.
The Builder-Investor
In late 2024, I stepped away from my role as a General Partner at TwentyTwo Ventures after helping Katey close out the final batch of investments in our Fund VI. We haddeployed more than $15 million into dozens of really exciting Y Combinator startups, and it was so exhilirating helping support founders right at the beginning of their journey once again after having worked at Kickstarter and Y Combinator.
And even though I came to it with a decent understanding of VC, lots of experience and past investments, my time at TwentyTwo really helped me cement my understanding of seed capital from the inside of a small seed stage fund. It was also so refreshing to be back in the saddle of the startup-world alongside some really exciting ideas and great founders. But I felt myself getting a little antsy, and after some encouragement from friends and family, the natural next step felt obvious: raise my own fund.
I spent the first half of 2025 exploring that idea with a trusted friend and a handful of incredible advisors. We made a deck, refined a thesis, tried to agree on a name, and generated a ton of interest from my network.
A few months in, I hosted a dinner with potential LPs and advisors that galvanized me. The conversation jumped from AI’s impact on labor markets and its possible cultural implications, to the future of human creativity and what we really want from technology. The mood in the room was obvious: with the advent of LLMs, we’ve arrived at a spooky inflection point in human history – we’re simultaneously surrounded by an undeniable wave of opportunity but also wary about what is about to change.
I didn’t quite realize it at the time, but this wave had begun to pull me under.
I’ll never forget the first time when I started up Claude Code in early 2025 and kicked off rehabilitating an old project. A week or two later I looked up and realized I could build things in a week that would have taken 3-4 developers a month. Like many other people over the last year, this drive overtook me. I started pushing out side projects left and right: a cat breed analyzer, a prototype of a 15th anniversary edition of Emoji Dick translated by Claude, a number of open source libraries, and countless other quick hack projects that seemed to just keep coming.
The most engrossing project has been a digital version of the tabletop game Monikers for my dear friends over at CMYK games. Though I had never written an iOS app before, I built it in Swift. In only a couple of months, I’ve shipped a stable beta to a dozen play-testers, built on top of a robust Rails backend. I’ve even incorporated a complex translation management engine that handles internationalization for thousands of cards across a dozen languages, from Thai to Hebrew.
So, that same week as our pre-fund dinner, when I found myself losing track of time, shipping things at an embarrassing pace, my partner Louise said something that hit home:
You LOVE it, you love building things, just admit it.“
She was right.
Money, what is it good for (especially now)?
Amidst all the code projects and VC conversations, I began to get the sense that AI had begun shifting the ground under venture capital itself.
While trying to distill our best guess at what the next generation of companies would look like for the fund, I wanted to focus on:
- Companies using AI to exploit a vertical their founders were experts in;
- Products that differentiated on something other than shipping software fast – cultural savviness, human factors, hardware, etc.;
- Teams that understood the new bottlenecks, like the exhaustion of publicly available data to train on. But we kept returning to the same question: when AI tools can almost replace a full engineering team, what exactly is the VC model solving for? If founders can validate ideas with $50K instead of $500K – and can reach profitability – what’s the venture money value prop?
Capital used to be a scarce resource but even in this post-ZIRP world, money and frothy valuations feel abundant for founders. But now MVPs can be built with minimal headcount. Founders who could get funded by anyone are choosing their investors based on everything except the check size – domain expertise, distribution channels, talent networks. And while I was confident I could bring lots of value across those dimensions, it became clear that AI is accelerating venture capital’s transformation from a financial product into an even thinner service business.
For someone who’s happiest in build mode, it started to feel strange to focus on investing during the most exciting moment for builders in a generation.
A pivot, of sorts
I’m not abandoning investing and I don’t think VC is going anywhere anytime soon. There are lots of crazy ideas out there that need a lot of money quickly, and VC will always be great for that. I just realized I didn’t want to be fighting these headwinds while missing out on doing what I enjoy most.
So the good news is that I’m going to continue backing exceptional founders shipping great ideas and I’m lucky enough to be able to do it using my own capital. But I’m going to be doing it as someone who’s building alongside them, not as someone managing other people’s money through a traditional fund structure.
I’m still figuring it out, but this will probably be some combination of angel investing, syndicating deals to friends who had expressed interest in my fund, partner-investing in projects where I can contribute technically and building products that demonstrate a thesis rather than just funding it.
What’s Next
For the foreseeable future I want to be heads-down building the kinds of products I can’t stop thinking about – the technically complex learn-as-you-go and creatively weird projects that only someone with my particular blend of interests would pursue. The kind of stuff that pulls you in for hours and helps you understand a new corner of the universe.
Over the last year, sometimes this has meant developing games, other times it has been complex financial modeling software. I’ve even gotten into modeling power demand curves for a friend’s energy company. It’s exhilarating and I’m totally hooked.
In terms of investing, I’m most interested in strategically backing founders attacking problems I can get viscerally excited about. But I also love the weird stuff that breaks my brain in the best way – projects at the intersection of art and technology, tools that shouldn’t exist but do, gutsy movies, and whatever else grabs me.
To those who were ready to back our fund – thank you. I’d love to bring you into specific deals as they arise. To those building weird and/or great things at this moment – let’s talk. The builder-investor model might not be for everyone, but for those of us who can’t stop shipping and have the resources to do it, it feels like the only honest way forward.
Look around, this couldn’t be a more exciting time to build things – I’ll see you on the inside.
Playa Marbella, Costa Rica