When to Fight

On cockroaches, startups, and starting over

Natascha and I bought a place in Brooklyn recently. Excitement faded to resignation when we (and our home inspector) discovered that our old but well maintained building was also covering a century’s worth of skeletons: pipes duct-taped together, a boiler on the brink. Our kitchen appeared to be the Coachella for cockroaches. 

People have remarked at how challenging our nine-month backpacking trip through Latin America must have been. Difficulties arose, of course, but challenges were surmountable. Generally speaking, we could always leave. And sometimes we did: after our second scorpion sighting in our Guatemalan hostel, we cut our trip a day short. 

Our trip was defined by flexibility and independence; it was situationally perfect. But recently, we’ve focused more on thinking through a longer time-horizon than we historically have. And to create anything lasting, the only way out of challenges is through them. We have to create the version of the world we want to live in.

I’m seeing this mindset shift arise in two areas: our new place, and my startup. I’ve already talked about the first, so time to address the second. I’ve talked about the general area of focus - building new solutions in venture capital to better align incentives between founders and investors - but I can share more about what I was working on. Past tense required, because I also made the hard call to shut it down.

Context on my startup, TXF: Most founders end up with no financial return, even as venture capital as an asset class performs. We created a solution to help founders invest a small share of their equity in other startups, providing them with tax-advantaged diversification and a much-needed founder community. To ensure proper portfolio quality, we went to market through VCs, offering to build this solution at no cost for investors to offer a high-performing subset of their portfolio. (Full deck here).

In our view, our solution helps address the mental health epidemic among founders and better aligns incentives between founders and investors. (Founders that have some downside protection are incentivized to swing bigger). While most investors privately agree with our assessment, none was willing to take the first step. We received some funding and founder commitments, but ultimately TXF wasn’t urgent enough to adopt.

I considered persisting, trying a different flavor of the solution. I thought about the battle against the cockroaches, and how a delicate combination of caulking pipes, boric acid, and lavender plants seems to have kept them at bay. Isn’t the only way out of a challenge through it?

Instead, I decided to move on. Startup founders have to solve problems and fight fires every day, but they only really have to win one battle. The key is to pick the right one. Although addressing the problems we tackled is fundamental, even existential, to the industry’s long-term health, I lost conviction that now is the right time. 

I’m taking on some consulting work in the short-term, but I’ve already begun to dive into some new projects, with every intention of making the next one work.