If You Want to Go Fast, Go Alone, If You Want to Go Far, Go Together

Everything is easier when you have good help

I had the idea, I had enough skills, and I had a version that was at least somewhat functional.

But I couldn’t keep making headway by myself. Time is the eternal enemy of the mortal. It was time to bring in reinforcements.

One friend had told me to sign up for the YC Startup School, which I did, and was working through their curricula. YC strongly emphasizes the importance of a cofounder.

I didn’t have a cofounder for any of my last startups except one, who was my girlfriend at the time, which is I’d… not recommend. The cofounder gap was another miss on the checklist of patterns to match to improve my chances of success.

I signed up for YC cofounder matching, and cranked through profiles to see who could be a good candidate. But I don’t really like meeting people online. It’s a real crapshoot. I love the internet but it poisons a lot of people’s brains, and it’s too easy to be false. I took calls and met some great people. While I was visiting SF, I met a few in person. None I’d make an offer to as a cofounder, more for a divergence between what they wanted to build than as a statement of their capabilities.

So I started calling friends again, asking them who would be a good cofounder. I got a bunch of referrals and started interviewing them. One friend pointed me to Wes.

I talked to Wes a few times and found he’d had three prior companies over the last 20 years. He said they’d never taken venture investment, which was a good sign - anyone that can build and exit multiple companies over decades without professional investment has a grasp of what a company takes to survive.

And within a talk or two, Wes had started to stand up his own version of the project, which was another really good sign.

One of the first things that he said was that a client-hosted solution would take too much work to turn on, for an MVP we needed something that clients could turn on in a few minutes without any effort. Wes suggested that we move to a CDN model with a reverse proxy, and build the Docker as the proxy.

Turning on the CDN would only take a few minutes of DNS changes for anyone to set up. And we could still deploy the container directly into the client environment, so client-hosted was still an option.

He suggested we move to away from our fixed-location defined-server host and into fly.io, a serverless cloud host. That we move to a monorepo so we could build all the elements of the app inside the same repo. That we automate our build and deploy process through Github actions. That we implement a tracking pixel for initial data collection so people could taste-test the analytics without having to turn over their routing to us.

I could go on, but the point was that Wes had the credentials, experience, and motivation to jump right in and start putting together the stuff we needed to take the demo from something “working” on my system into something that was alive on the internet.

Following the guidance from YC Startup School and Founder Matchmaking, I offered Wes the cofounder role with 50% equity split and a 4-year vesting schedule (1 year cliff, 3 year monthly).

I have my own twist, though - I always do a 12-week evaluation period. That means either of us can break away in the first 3 months for any reason or no reason, no harm done, no hard feelings. We have a 3-week check-in to make sure we’re still aligned, then a 6-week check-in, and a 12-week check-in. If we make it past all three without any serious concerns from either side, we move ahead with the formal engagement, backdating it to the start of the evaluation period.

I’ve done this for every executive, advisor, board member, employee, and contractor I’ve ever hired. It’s helped highlight issues early and avoid committing. It’s a great way to engage someone who you’ve not worked with before while making sure you have an escape hatch if needed.

For those keeping track at home, I organized the company in Apr ‘24, built my demo by Jun. Wes and I met in Jul and agreed to set Aug 1 as the start of the trial period. We set a presumptive date of Sept 1 for a working MVP.

Time is the greatest enemy of the mortal! Would our dear heroes prevail against all odds? Or would we be struck down?

To find out, tune in next time, same bat time, same bat channel!