How to not break up with your cofounder
Go together or don't go at all
In this issue of Product for Engineers, James Hawkins shares how he and PostHog cofounder Tim Glaser keep their relationship healthy.
1. You need to be equal partners
Tim (my cofounder and co-CEO) and I started with quite asymmetric experience.
I had previously been a VP of sales, responsible for sales, support, and account management. Tim was an insanely talented, 23-year-old engineer, and was much earlier in his career – I’m nearly 10 years older.
I diligently pushed myself hard at school, got straight As, and went to one of the top universities in my country. Tim quit school at 16 because he realized he was earning more than his teacher, and has worked ever since.
Despite these differences, we realized it was important to be equal partners in PostHog from the outset. We took 50:50 equity in the company and, once we could afford to do so, took the same salary, too.
Not doing so felt wrong on a human level because we were motivated by the idea of going on a fun, ambitious journey together. But it also felt illogical on a strategic level.
Most startups fail because the cofounders break up – more so than failing to find product-market fit. (source = I made it up, but it’s extremely common and often business problems can be traced back to dysfunction at the top)
Therefore, I’d argue you should just minimize the risk of you and your cofounder breaking up. Anything that could cause resentment, like a lack of evenness at the outset, should be avoided.
Despite our differences in experience, I frequently feel I’m underperforming relative to Tim and need to remind myself how effective we’ve been together.
2. Good relationships aren’t set and forget
You need to be intentional about the way you work together day-to-day.
Making time for each other is vital. We have an hour every week, but we block out time afterwards, so we can overrun if we feel like it. An important issue shouldn’t be left unresolved just because you ran out of time on your calendar.
We’re a remote company, but we still spend plenty of time together. When travelling together, for example, Tim and I always book an Airbnb instead of booking separate hotel rooms.
This grounds us back in the early days of PostHog when we worked 16-hour days, and pivoted numerous times. It also maximizes opportunities for us to talk freely about problems and opportunities, and stops us stewing on things in isolation.
We have lunch and dinner together whenever we can. I love Indian food, but my partner hates it, so dinner with Tim is an opportunity to indulge in this and talk about what’s on our minds. We both love breakfast at Dishoom.
Our longest-running habit is a doc we started five years ago that we put all our thoughts and feelings into each week. I treat anything that frustrates me as a flag that I must put it in there, alongside the positive, exciting things that happen too. Tim does the same.
Ultimately, relationships only work when you can talk easily about how you feel. This is very basic. I’d encourage you to carry this principle into any relationship. Not doing so causes resentment. Building habits like this will make this easier and stops your cofounder relationship going stale.
3. Don’t get attached to titles
A CEO is perceived as being “in charge” of the CTO, but do you actually work like this?
We started with these titles because it seemed logical and normal, but we soon realized it’s not how we operate, or how we’ve driven great results, so we decided that we were co-CEOs. We’d rather label what is working well for us than worry about how this looks to everyone else. Our responsibilities internally are very clear.
We feel we make better decisions like this, and our intrinsic instincts complement each other. For example, I tend to push up ambition, and Tim is world-class at setting the pace, clarity, and making it all happen.
This doesn’t mean you shouldn’t use typical CEO / CTO titles, or whatever makes sense for you. Just don’t let those titles define how you work together.
4. Work on the things you care about most
Not getting attached to titles allows Tim and I to adjust our roles based on what we’re uniquely good at, what we enjoy, and the needs of the company at any point in time.
In practice, if I seem to care about something more than Tim, it’ll probably end up as part of my responsibilities, and vice versa. This keeps us motivated and energized by working on new problems and ideas, rather than stuck in lanes.
For example, I owned sales when we were an early-stage company because it was all about going on calls and dealing with customers. Later on, Tim stepped in for a while when we needed to figure out processes, how we handle sales data, and other thorny problems he had the skills and temperament to figure out.
Right now, we split our responsibilities around the products we care most about, and are uniquely qualified to help progress:
Tim is focused on platform teams, our data warehouse and customer data platform, and new products like LLM observability. He’s great at execution and understands the ins and outs of these products better than I.
I’m focused on marketing, and AI-first products and features like Max AI, our “AI product manager”, which we believe will become the default interface for much of PostHog. I love pushing ambition and taking bets, so this suits me perfectly.
There are also a handful of things we both want to be involved in, such as people and strategy. We think both of us being involved leads to the best decisions here, and keeps us aligned.
5. Zoom out to solve problems
If you’re struggling to agree on a specific problem, it’s always best to zoom out and solve it in the abstract. For us this means going back to core principles, which then go into our company handbook.
For example, we once had someone we valued asking to take a sabbatical, and we struggled with how to solve for this person. Instead of focusing on this individual’s request, we asked ourselves two key questions:
Are people able to take lots of time off at PostHog in general? (We offer unlimited holidays with no managerial approval required, so we said yes to this.)
Are sabbaticals compatible with the kind of company we want to build, and our long-term ambitions?
We eventually decided against offering sabbaticals, even if it meant we might lose someone we really liked, because it was incompatible with the ambition and commitment we need to succeed.
By solving for the abstract, we took personal feelings out of the equation and thought more deeply about the long-term impact, and the culture, we want.
Misalignment is another important flag here. If you feel like you’re pulling in different directions, it’ll get amplified through each layer of your company
For example, we’ve struggled to get on the same page around how design works at PostHog. We both want good design, but have had very different perspectives on how to tackle it, and thus the kind of people we should hire. The way this gets painful is we spend a month recruiting, then the “less involved” of us rejects candidates at the final stage that everyone else is very keen to move forward with.
Again, we solved this by zooming out and codifying our thinking in our company handbook, which then gave us a reference for making better decisions in the future.
6. Focus on opportunities before problems
After running PostHog for a while, we realized that our 1:1s had evolved into a list of difficult problems to solve. This meant that every session felt hard and draining.
On feeling this happening, we realized it meant we were only focused on defence, but you can’t win thinking this way! We were never talking about opportunities.
To fix this, we structured our shared doc (the one I mentioned earlier) to simply be (1) good stuff (2) bad stuff, and we always start with the good stuff first, because starting with the bad stuff means there’s no real energy to do “optional-feeling” opportunistic things.
Remember that startups win on their upside because everything is screwed up by default, so make sure you spend plenty of time on it. You may just find that problems start seeming smaller when you’ve got incredibly positive things happening.
Had we changed nothing, I’m certain our working relationship would have suffered by being overly focused on negatives.
7. Shared values make everything easier
As I outlined at the start, on paper Tim and I are very different.
I’m older, less technical, and I’m married with two kids. We took very different paths in both education and career. Tim loves pineapple on pizza; I think it’s a mortal sin.
But we do share some immutable values around work and the type of the company we want to build.
We both value:
Speed over perfection
Individual contribution
Proactivity
Giving people autonomy
Being ambitious
And we both dislike:
Fluffy, enterprise sales BS
Hypothetical plans where no one does anything
Pointless meetings
We didn’t talk about these things before we started working together, we just got lucky, but they are fundamental to why we work well together.
These values have shaped everything we do at the company, and ensure that even when we disagree on specifics, we can trace things back to a shared value. If we had very different values, I’m certain we’d have failed long ago.
So, when you go looking for your cofounder, think and talk about what values you share, because you probably won’t luck into it like we did.
Finally, if you’re thinking about going it alone, think again. You’re more likely to succeed if you have a cofounder who is as motivated and into it as you are.
It’s more fun, too.
Words by James Hawkins, Pizza Margherita fundamentalist.
Amazing
thank you for this text, it resonates with me