How our startup died but relationship survived
6 actionable tactics for a healthy & effective co-founder relationship
I love the fact that after going through the extremely difficult decision and process of wrapping-up Track — our consumer tech startup we worked on for two years — Henry Oakes and I can still go to our favourite North London pub together for a pint (The Lamb). However, I don’t take our relationship for granted, nor do I think we just got lucky — we worked hard on it, even if we didn’t always get it right.
Despite being in the midst of winding-down Track I feel compelled to share my reflections on what we did to cultivate a relationship that endured, even as we approach the end of the Track (sorry, had to). But first, some context…
Henry and I met in 2016 on a year-long MBA programme at Imperial College Business School in London. I’d come from a career in marketing, keen to embark on my first startup and Henry had just exited his first business. On completion of the programme, we launched Track — an AI-powered money manager designed for homeowners. We hit a good run of milestones, including launching on iOS and Android, having a few hundred users, being backed by a VC and expanding the team. However, after a failed crowdfunding campaign on Seedrs, we were unable to secure the required funding for the business and made the call to wrap things up.
So, let’s get into it. What did we do to give ourselves the best chance of a healthy and effective business relationship (p.s. I think this stuff is relevant in most relationships I have, but this will be through the lens of a co-founder.)
1. Start with YOURSELF
Attempting to better understand yourself in terms of what makes you tick, what triggers you emotionally, what do you love/hate, what are your strengths/weaknesses, what type of person energises/drains you, you get the point; is paramount to a successful relationship.
By simply being curious about better understanding yourself, you are already in the right headspace, you are already demonstrating emotional maturity.
For example, I tend to get emotional when there is a conflict between Henry and I. Now nothing wrong with getting emotional, I can’t help that, that’s my inner chimp (learn more in Dr Steve Peters’ powerful mind management book The Chimp Paradox), however, what does cause issues is if I act on impulse when in that emotional state.
Tactic #1 — Sleep on it. Henry and I will sleep on any major decisions but particularly if there is a disagreement on the course of action. When emotion settles, clarity emerges.
Keeping with the theme of self-awareness, let’s talk about empathy. It is very hard to truly listen to what someone says if you can’t open your mind to the possibility that your point of view isn’t the only one. This is made easier by self-awareness and confidence.
If you are in a discussion with your co-founder, I cannot stress enough the importance that they believe you are truly listening and considering their point of view. Otherwise, it doesn’t matter what you say next, the walls have come up. You can have a strong point of view and confidence, while still being open and considerate to others’ views. Henry was a good example of this.
Tactic #2 — Argue both sides. When we have an important decision to make (or there is a disagreement), we argue both sides of the aisle, no matter what side you sit on. For instance, a classic, to make a hire. Together we both argue tooth-and-nail for why hiring a product manager, for example, is the best course of action and we’d be stupid not to. Then together we both argue as passionately why hiring a product manager would be a stupid idea. This tactic forces you to loosen your grip on preconceived opinions and offers a much higher chance of not just a resolution, but the correct course of action being taken.
Tactic #3 — Daily mindfulness practice. I do a 15 mins meditation [most] mornings. One sure way to be out of tune with your own emotions is a busy mind running circles in your head. Give your mind a break by focusing on your breath each day and I reckon you’ll see benefits personally and by extension, in your relationships.
Lastly, a bonus tactic, I started therapy about a year into Track and found it hugely helpful in my self-exploration — it supercharged it. While the reason for starting therapy wasn’t solely Track, I have no doubt it helped my contribution to our founder relationship.
2. Make it a priority
I massively underestimated the concerted effort that would be required to maintain a healthy and effective relationship between us. I shouldn’t have been surprised; in an early-stage startup, you’re spending more time with your co-founder than anyone else in your life! Systems need to be put in place — here are a few that worked well for us.
Tactic #4 — Track Founders Forum. This was all about creating space for praise and feedback. Every couple of months we would get together outside the office (usually for breakfast) and take turns sharing the following:
About yourself:
- What I think I’ve been doing well
- What I think I could do better
About your co-founder:
- What they’ve been doing well
- What I’d love to see more of
The format worked well. And you’ll notice the wording on the last question “love to see more of”. I got this tip from one of Tim Ferriss’ podcasts, it’s a way of giving constructive feedback that does not get the other person on the defensive.
Feedback is a gift, but it’s hard to get. The Founders Forum allowed me to hear feedback from Henry like; try to waffle less when an investor asks a question, push the outsourced dev agency harder and many other actionable pieces of feedback. And it, of course, allowed me to share my thoughts with Henry.
Tactic #5 — Friday Fun. Everyone’s busy and no less so than having a crack at building a business from the ground-up. Nevertheless, each Friday at 1600 we prioritised having a game of tennis, followed by a beer and what we called our “On Track” end-of-week meeting. It comprised of saying what the wins of the week were and where the next wins are coming from.
Now I don’t know tangibly what whacking a tennis ball around, having a pint together and talking about wins and future wins each Friday did for Henry and me, but I usually went into the weekend feeling good.
Actually, as a side note and another bonus tactic, we were very good at celebrating wins in general. For example, when we got invested in by VC, we went and played virtual golf. I thank Henry for this tradition, and I learnt later that it is so easy to just bounce from one thing to the next in a startup and that taking the time to stop and pat yourself on the back is super important. Your brain remembers the dopamine release and that gets you through the inevitable next challenge that is around the corner.
3. Laughter
Yes, it’s stressful at times. Yes, it seems like your project is the centre of the universe and the weight of the world is on your shoulders. Yes, there will be times of conflict with your co-founder. Yes, there are a plethora of unpleasant emotions like fear, uncertainty, imposter syndrome and insecurities. But among all of this, one of the things Henry and I did well was not take things too seriously and so I leave you with a final tactic.
Tactic #6 — Have a laugh. They say laughter is the best medicine and I have to agree when it comes to co-founder relationships. The importance of this throughout our relationship has become more apparent to me as we wind-down Track. Recently, we’ve laughed hard as we reminisce — one example being a final meeting with a VC partner before they committed to invest, it was the end of November and we both had very questionable Movember ‘taches. Alas, it went well and they invested!
So that’s it from me. A big thank you to Henry and everyone who was a part of Track’s journey. I’m excited by what’s next after putting a line under Track and also that because of Henry and my continued relationship, it’s cool that another business together is a possibility — time will tell.
Request: share your own experience/tactics/observations of co-founder relationships — I’m interested in this topic and business psychology in general so would be keen to hear!
Recommended reading: Henry’s piece “Winding up my startup” is an honest diagnostic of why Track failed and is littered with insights about fundraising.