Four of my firsts in 2022

First Fundraise

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

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: