I’ve always found it interesting to think about co-founder relationships. I’ve been in a few myself, some which were not completely successful and then more recently working with Leo for the last 3 years has been an absolute joy. It’s fascinating to me how co-founders need to be different in many ways and at the same time have shared values they are aligned on. It’s a real art to find someone who you work well with and trust.
I recently watched a video of an interview with DHH from Basecamp and found the audience question on co-founders interesting and very in-line with my own experiences on what makes a good match.
Complementing each other in skill-set
"When two men in business always agree, one of them is unnecessary." - William Wrigley Jr
I think it’s super valuable to have different strengths as founders. I often see fantastic products from great engineers and product people, where I believe the product should be used by far more people. It’s probably because the founders are not naturally inclined to do marketing, and so keep working on the product.
"I see a number of startups where the founders are too alike. Either they agree on everything or even worse they do the same thing. Like starting a company with two programmers - I don’t think that’s a good idea. I think you need skills, and you need mentality, to complement each other." - DHH
In the early days of Buffer, I reached a point with the product where it had a couple hundred users and some paying customers, and I knew in my head that I needed to switch to marketing. There was validation that the product in the exact form it was in, was already useful to people. There was clearly more people out there who would find it valuable as well. However as a developer it was a real challenge to be effective at switching to marketing instead of fixing bugs or building out new features. Luckily for me, that’s when Leo came on board as my co-founder and had a massive impact since he was a great marketer.
It’s also useful to have different mindsets on the business aspects too:
"For me and Jason on skills, Jason was all about design and I was all about programming. So that was just a natural fit right there. On running the business, Jason is more of a risk-taker and I’m more conservative. I’m more about running the numbers and making sure everything’s alright, and Jason’s more like let’s just rip away everything and try something new and take a leap. I think you need both of those things to pull the business in the right way." - DHH
For me and Leo, we’re both scrappy and take the lean mindset. At the same time, Leo is probably more inclined to push something out of the door extremely early, whereas I like to be a little more calculated and logical and get the best balance of learning and not wasting time by building something out without validation, but still shipping something quite polished.
One of the most interesting ways Leo and I complement each other is on “doing” vs “reflecting”. I often joke that if Leo and I each have a daily todo list with 5 items on it, there is absolutely no question that Leo will get through his 5 tasks. For me, I struggle at times to get through everything. I work hard to be productive, however I also like to take time to reflect on the direction we’re going and ponder changes. We both aspire to be more like each other in this regard: I’d love to just crank through more, and Leo says to me he’d like to reflect more and sometimes realize not to do some tasks. We talk very regularly and help each other, and we end up at a nice equilibrium.
Aligned with each other on values and vision
"At the same time, you have to have some overlap too. Jason and I obviously share a lot of opinions about how to run a business and what is important and our values are incredibly alike, in terms of creating a sustainable long-term business that does well for both its customers and its employees. So you can’t just be polar opposites and expect that everything’s going to be daisy. There’s got to be overlap on important cultural values in the company, but outside of that seek as much diversity as you can." - DHH
The hard part of finding a great co-founder is that you want to sufficiently complement each other, but at the same time it’s vital to agree on fundamental values and what you want to do with the company. If one of you wants to flip the company within a couple of years and the other wants to make it their life’s work, it’s going to be difficult to agree on key decisions.
From an early stage it became clear that Leo and I were very aligned on many of the values which became the Buffer culture. I introduced Leo to How to Win Friends and Influence People and we spent countless hours discussing the principles and examples. Leo has always had tremendous gratitude for the opportunities he has had and is one of the most positive and happy people I know, and that was something I aspired to focus on more. I always enjoyed being very open and transparent about my learnings and progress and this came completely naturally to Leo too and he enjoyed pushing us further in that direction.
How did you meet your co-founder and what are the key ways in which you complement each other? I’d love to hear about your experiences
P.S. We need help with many areas of Buffer right now, to complement the existing great team. Check out our openings