My co-founder and I broke up. Here's a post-mortem.

My cofounder of a year and I recently parted ways, and I thought that I'd take some time to write down our experience, and how we came to the decision to stop working together. I think it's an under-talked about part of the startup journey for a lot of people, and while in our case the breakup was not at all acrimonious, the feelings of failure and disappointment are still there.

First off, a little background on the two of us: David and I met through mutual friends in New York City. He was an algorithmic trader who had studied math and CS at MIT, and I was a software engineer/freelance journalist who'd covered the technology industry for years for publications like the New York Times and Wired. On paper we were a really strong team. Not only were we technical and pedigreed, I was also clearly a hustler! It's hard to break into traditional publishing and if I could do that while also holding down a day job as a software developer, I could definitely start a startup in a bull market. In retrospect I was pretty arrogant.

I saw this tweet a while back that says that as a founder, your product is clarity, and I feel that perfectly sums up the biggest problem that David and I had, which was a lack of it. Coming out of the gate, we didn't have a clear idea of a problem we wanted to solve, or even a persona we wanted to target. We were would-be founders in search of an idea. And while that isn't necessarily damning, it was compounded by the fact that we didn't have obvious domain expertise which would guide our search — i.e. you're two ML PhD's, you should probably start an ML startup; you've spent 10 years in manufacturing, you build a solution for factories.

My work experience consisted of five years in infrastructure engineering, first in Observability at Uber, and then in local search infrastructure at Google. But these were big companies, where I was a line engineer, a cog in the machine. I didn't feel like I had visibility into the process of actually creating an infrastructure product, talking to customers, understanding their needs, architecting the whole system. David, meanwhile, had spent his entire career at Hudson River Trading, a super successful algorithmic trading firm, but he had left precisely because he was bored of trading and wasn't particularly interested in building financial infrastructure. He was also philosophically opposed to crypto. This meant that some of the areas where we had perhaps the most founder-market fit, we were not considering. (Side Note: the other area where I arguably had domain expertise was media/journalism, but we were forewarned that building a content business was not a great idea, especially if we were technical and could do something else.)

We ended up doing basically a brute-force search through the space of startup ideas. Most of our ideas were B2B, but a few were B2C, or in the creator space. (It's long, but if anyone is interested, I outline all our projects at the end of the post). The B2C projects typically arose from our own problems and we would do just a minimal amount of asking around in our networks or putting up a landing page to validate the idea before diving in and building. For B2B projects, we were running a bit more blind, since we typically did not have work experience ourselves in the area we were exploring, so we would reach out to certain personas on LinkedIn, for instance, account execs, ask about their workflow, develop hypotheses for specific problems they had, and then try to come up with a solution. We both read The Mom Test and were aware that people would regularly lie to you in an effort to be nice or encouraging, and we tried to stave this off by sticking to factual questions and asking people to screen-share their existing setups as much as possible.

One thing that we struggled with was when to switch from "we want to learn about the space" mode to "here's a solution, what do you think?" mode. The Mom Test seemed to imply that by presenting any idea at all, you were biasing the interview subject, but it also seemed impossible to get good feedback by perpetually speaking in generalities. This was further contradicted by studies that show that people are more truthful when they have concrete artifacts to respond to; in order to jog their judgement, it helps to show mocks and demos.

Another thing I struggled with, despite the admonitions of The Mom Test, was asking the tough questions. Because conviction was generally in short supply for us, I think I instinctively recoiled sometimes from asking questions that might further deplete it. And while we did prep for the calls sometimes, we should have prepped more. In particular, we didn't always go into the calls with certain hypotheses in mind that we wanted to test, or gather more data for. It was often a more dispersive conversation that, while enlightening, didn't necessarily get us closer to identifying either a problem or a solution.

The reality is that even so, a lot of the products we worked on probably would be viable (or we could at least raise money for), but we never stuck with one of them long enough to find out. We would work on something for a while, get bored of it and realize that we didn't want to spend the next ten years of our lives on it, and then want to move on to something new. There were a few exceptions, where we worked on something for longer and didn't see the traction we needed to, but by and large we were pivoting a lot, and for a lot time, between wildly disparate areas.

The other thing we did too much of was over-intellectualizing. It wasn't that we weren't aware this was bad. But it was really challenging to avoid because when we didn't over-intellectualize we often ran into issues like market size. The wisdom from VC's and other founders was that the market by far was the biggest contributor to a startup's success, and when a good team met a bad market, the market won. So we would see problems we thought were real and interesting, but then worry about whether the market was big enough, and lose conviction. The pressure to build a venture back-able startup often prevented us from building any business at all.

Lots of companies fail because of co-founder conflict, but I actually think that under different circumstances David and I could have been successful together, i.e. if we had a clear sense of the problem we wanted to solve/the product we wanted to build and we were both really excited about it. The experience of being cofounders also hasn't, I think, fundamentally changed our view of each other. I still think that David is someone with incredibly strong principles who works extremely hard and is extremely smart.

But results speak for themselves and after a year of kind of going to circles on various ideas, it was clear that something wasn't clicking. We thought about bringing on a third co-founder, someone with more domain expertise, but our interests were sufficiently divergent that maybe the way forward wasn't together.

David is taking a bit of time off, and he's looking at joining some other early stage projects. I recommend him wholeheartedly. You can drop him a line at itsdchen@gmail.com.

I am taking some time (probably through the rest of the summer) to focus on my writing. I have four or five big pieces on various parts of the technology industry that I've been itching to work on for a while, but felt like I couldn't because I should be 100% focused on the startup.

I am also doing some consulting work for tech and finance firms, mostly writing strategy-type memos.

Some other ideas I'm interested in exploring:

If you're interested in any of the areas above, DM me on Twitter or drop me a line at yirenlu92@gmail.com.