Ways I grew in 2022

Four of my firsts in 2022

First Fundraise

Before Manifold, “fundraising” seemed like a mysterious black box reserved for other people to approach:

  • Mind-boggling sums of money at play
  • How does equity even work?
  • VCs seemed vicious — who are these people?

My previous startups were all bootstrapped, and I’d drawn the mentality of “bootstrapping is virtuous, VC money is poison” from the Indie Hackers crowd. But Manifold made much more sense as a funded startup, and it seemed like part of a lifelong dream, to walk the path of a “proper startup founder”

Since raising Manifold’s Seed and Seed+ round, as well as getting a few six-figure grants, fundraising seems much less mysterious to me now. Fundamentally it’s not that different than applying to jobs. Work your network, write a resume, line up a bunch of interviews, and negotiate your value.

Beyond giving me the confidence that raising money is a thing I can personally do, fundraising taught me how money flows in the startup ecosystem. This then helps me step back and understand the pain points for things like 🪙Why impact certs might be really good — a proposal only made sense after developing a practical knowledge (as opposed to book knowledge) of equity.

First Hire

The purpose of raising all this money for Manifold was to expand our team. (Headcount is basically the only significant expense in most software startups). Luckily for us, our user demographic includes a lot of software engineer-types, so it wasn’t a very hard sell to find people to join our team.

At Streamlit, I’ve found candidates, interviewed them, and sold them on joining my team — so I’ve had some experience with the different pieces involved with hiring. But hiring Manifold’s first engineers was very different, as my cofounders and I have the ultimate responsibility for the hire/no-hire decision.

I hate saying “no” to people. This can be good in some contexts; I think people generally find me nice and approachable, and I’m pretty good with moving forward with candidates we’re excited about. But with hiring, I actually need to say “sorry, we can’t give you this thing you really want”.

First Offsite

Planning a 20+ person, 2-week team offsite in Mexico City

After visiting the FTX (rip) Fellowship program in the Bahamas, I was super excited about the prospect of meeting up again in person for a team onsite. Could we replay this model ourselves?

The answer turned out to be yes! Making an offsite happen shares a lot with making a project or startup happen; they are both impositions of someone’s will into reality. To make an offsite happen, you need to balance:

  • A cohesive guest list
  • An exciting venue
  • A flexible itinerary

Each one only works with the other, in kind of a cold-start problem. The guests want to know where you’re going and what you’re doing; the venue depends on where the people are and what you want to do; and the itinerary needs to fit the interests of the guests and the fruits of the locale.

I’m especially proud because Mexifold was fairly groundbreaking, de novo innovation where I didn’t have an existing example to work on (the closest were my previous New York hacker house, and the Bahamas trip). Also, a lot of small decisions I made (such as room choices and having common areas) I think played out quite well. It bonded together our team and our community; created a template for future offsites; and formed the kind of company that I myself would want to work at.

First Relationship

This is the most surprising way I grew — I might have guessed at some of the other developments of 2022, but ending up in a happy, stable, nurturing relationship was more or less a black swan event for me.

Things that surprised me:

  • That I can fall in love; that the same addiction I’ve felt toward certain books or video games, I could feel towards another human being. Love songs make sense now. It’s difficult to recall what life was like before.
  • That someone could fit me so well. For a long time, I’d been approaching dating with a cynical mindset like “The One doesn’t exist, it’s all about navigating tradeoffs”… but since meeting Rachel I’ve thrown that philosophy out the window.
  • How much time a partner takes. It’s time I’m more than happy to give up; but now I understand why friends who enter relationships disappear for a few weeks. See 🗼Ambition & Relationships