Cord didn't win. What now?

Across the last six months, I’ve been making my way through the practical reality of Cord not working out. I was the co-founder and invested more than 4 years of my life in that company. We built some good tech. We built a very strong engineering team. We landed 15,000 commits in a TypeScript/React monorepo. Shipped a command line tool for stacked diffs on GitHub. We memed so damn hard. We had two significant brushes with acquisition. But we didn’t win the game.

We also made lots of mistakes and spent loads of time and money on the wrong things, which we didn’t know at the time were the wrong things. We weren’t unique on this front. Most startups spend a bunch of time figuring out what their company isn’t. I’m not going to deep dive into our every shortcoming and misstep in this post. Folks who know me well can probably guess I’ll be enumerating those details again and again for the rest of my days. In this post, I want to keep it lighter and focus on where to go from here.

Eventually we had to face the reality that for the amount of money we were spending, the amount of time and energy we’d put in, and the commercial traction we were seeing… it wasn’t really working. We hit some non-trivial ARR numbers (in the territory of $500K), but that wasn’t enough to justify the big team and big expenditures. We also failed more or less entirely on GTM. I’m a product engineer who never aimed to learn about marketing and sales, but I can say I learned a hell of a lot. Sadly, it wasn’t enough.

We open sourced Cord and it’s now live and running in many production applications. I’m so proud to say that customers were able to adopt Cord, get the systems up and running, and mostly ignore it because it’s just super stable. Cord engineering was damn good.

One of the biggest lessons of Cord is that building great tech isn’t enough if you’re trying to sell software to software companies. You have to solve problems they can’t and/or don’t want to solve. We were constantly faced with product leaders (VPs of Product, CPOs, PMs, etc.) who were very excited about adding Cord to their existing product. They saw the value unambiguously. And then we’d get to the dev team and face a stonewall of NIH syndrome alongside a clear preference for building it all themselves, even when that meant shipping a vastly less-useful product to their end users. Many were the home-built chat features we lost deals to which were shockingly bad. In some cases, literally unusable. We were selling solutions to the problems that the dev teams wanted to solve. Alas. Alack.

So, we gave the investors back a big portion of the money we received. We ended Cord with multiple years of runway left. We could have kept grinding on that initial investment. Maybe hindsight will show that we should have. What I do know is that after 4 years of hard grinding and not winning, I was really careworn and in need of some time away from being constantly in the founder hot seat. I needed some time and space to lick my wounds, reflect on what I got wrong, and to decide what the heck to do next.

So, what now?

Never in my career have I had so many paths forward, all with totally different financial trajectories, lifestyle implications, stress levels, and potentials for growth.

Option 1: Be a founder again. I’m really scared of this. Being a founder took a huge toll on me emotionally and physically. It put a big strain on my family. One thing that makes me confident is that many of the hard calls we had to make at Cord taught me that my decision making is actually pretty good. Better than I gave myself room to believe. I also learned so much at Cord that is directly applicable to being in that hot seat again. It would be really different the second time around. But is it worth the stress and worry and constant sense that the world is on your shoulders? At Cord, I learned so much about who to hire. Who not to hire. Most agonisingly, what to do when you have a stellar candidate who isn’t a fit for the stage of the company at the time. About managing teams and how to balance team harmony with exposing the urgency needed to succeed in a startup. I learned so much about fund raising, GTM, sales, and the end-to-end of building and shipping a product. We built rock solid developer APIs, CLI, webhooks, UI components, NPM packages, and killer documentation. We served dozens of great customers. I know those roads. On top of all of this, I’ve got some truly amazing folks who want to go this road with me post-Cord. In some ways, it feels like this is the obvious choice. A second chance at the adventure with salty veterans who learned the same hard lessons the same hard way.

Option 2: Join a company as an early engineer. This seems like the most obvious option if I want a blend of the potential big upside of succeeding at a startup with the lower-stress of not being a founder. As an ex-founder, I’m better poised than ever to help a company grow. I can look back at my earlier years as a tech lead / senior engineer and see so many ways in which I wasn’t understanding the assignment. I was caught up in engineer priorities, not company priorities. Having been a founder, I know it just doesn’t matter that your tech is great if you’re not winning the game. And how the tech needed to win the game is often not the tech that engineers are drawn to. I know now to never take my eyes off the game-winning moves, even when it’s tantalising to just build great tech. One of the surprising things for me as a founder was seeing truly brilliant engineers — people far beyond my own abilities — walling-off problems to match what they found tractable or interesting. Even as the business languished. I know first-hand what a treasure it is when the doers can bind themselves to the business outcome rather than the tech. I could just go be that engineer in someone else’s company and not live so directly under the Sword of Damocles.

Option 3: Go back to big tech. I’m 4 years older now. I’m at a different stage of my life than I was when I left Facebook and felt the world could wait while I dawdled for a while. Big tech had a stability that I haven’t felt in 8 years. I could also feel confident that I was doing work that actually mattered in the world. It also pays way better. Being a startup engineer has so many upsides, but none of them are financial unless you win the game. There’s a very real pull to go find a big tech company, find a problem space I’m excited about, and get back to a working style I know super well. Maybe I’d even take holidays.

Option 4: Bootstrap something. One of the things that’s available to me, somewhat uniquely compared to other engineers, is the opportunity to prototype something quickly and cheaply and see if I can get it off the ground as a solo dev or very small company. I’m a user interface engineer in my soul. One of the things I learned at Cord is that to this day I’m still quite an accomplished frontend engineer. It also seems like I’ve got a much broader (and shallower) skillset than almost all of the engineers I know. I’m waaaay less skilled as a backend engineer than most proper “backend” folks. Still, at Cord I did all of the initial devops and deployment work. Setup the databases. Ran the server infra. Setup the developer workflow. Reviewed literally all the code for a long time. Hired the entire eng team. I also helped hire the sales team, co-authored a lot of our marketing collateral. I built our developer documentation system and completely rebuilt our company website… three times (changing things as we learned who we were and weren’t and what our needs actually were). I can’t help but feel that this extreme generality ought to hold the key to starting something small that earns me enough money to have the lifestyle I want for my family… without the sturm und drang of running a “proper” company. But that also comes with the downside of loneliness and an even more crushing sense that the world is on my shoulders. And, as I sit here today, I don’t know what the project is. Hrmph.

And the winner is…

Honestly, I don’t know yet. I wish it was as easy as seeing a blindingly stellar opportunity in front of me and leaping at it. But so far I haven’t seen any paths that look so clear cut. Rather, they each seem both promising and fraught in their own idiosyncratic ways. Variable and unpredictable.

In my soul, I know I’m motivated by building technical things. Especially products. Beyond that, I’m not so sure. For now, I’m stuck with the immortal words of Natasha Bedingfield:

🎶 The rest is still unwritten. 🎶