005. ‘Mo founders, ‘mo problems – Startup dysfunction by cofounder count
If you've ever worked at a startup, you're going to want to read this one 👀
Hi I’m Jen, and welcome to Safe For Work – a newsletter on scaling organizations, navigating a tech career, and tales of being a startup addict.
Cofounders. Can’t live with them. But also, can’t build mega successful companies without them.
Cofounders are should be your closest allies, but when interpersonal issues come up, it can flip things on their head.
Our culture tends to talk about tech founders as larger-than-life, (mostly) boy geniuses who single-handedly create billions of shareholder value and thus, are worthy of our collective worship.
But 1) building a successful company is never a solo effort, and 2) no matter how brilliant the founders are, they are still human and fall into very human dysfunctional patterns. Founding teams are the perfect example of the ways that interpersonal dynamics can quickly turn dysfunctional in the high pressure environment of a startup. As common as this is, it’s rarely discussed – so my hope is that by sharing this post today, more teams can see / address the problems early, and go on to achieve their full potential.
It’s easy to gloss over, but cofounder dynamics are incredibly important. The human relationships are critical to the success of the startup, especially at the early stages. Not finding product-market fit might be a primary killer of startups, but cofounder drama is a secret threat. (Another is bad hiring, a topic I write about a lot).
Over the years as a Startup Advisor focusing on Talent/People, I’ve heard too many behind-the-scenes stories about cofounder dysfunction. From the two cofounders at a well-known startup who parade their “great friendship” in press and fundraising, but secretly can’t stand each other in private – to the founder who gave their cofounder a sandbox in the corner to play in, and then complains about having to share equity with someone they consider dead weight. Misery is all too common, partially due to the lack of dialogue around recognizing the patterns early and working through them.
Most VC’s won’t tell you this. They can’t – it’s a group that’s famously good at business but bad at people (and sometimes bad at both 🙃). Many even play into the dysfunction themselves. All the more reasons to be aware.
So let’s break it down: Does more cofounders mean more problems?
The Solo (1) Founder
The dysfunction loop: Hyper-independence ↔ Never figures out how to scale themselves and ask for the appropriate help → Eventually crash and burn(out).
What it looks like:
Heavy is the head that wears the crown – The solo founder’s brilliance may shine through in coding, sales, or fundraising, but when it comes to scaling, they quickly get stretched too thin and starts to falter. Unless supported by a truly world-class executive team, the loss of appropriate oversight over various parts of the business leads to untenable problems.
Likely has an “I have to do everything myself” mindset, sometimes subconsciously. This makes it very difficult for anyone around them to give them meaningful feedback, stunting their growth as a leader. Loneliness and stress becomes a self-created prison. Anyone who reaches a certain level of success very quickly is at risk of losing touch with reality, but it hits the solo founder particularly hard. (See: “The J.K. Rowling problem”)
The company becomes exact copy of your weaknesses – e.g. The technical founder, who despite being CEO, puts all of their focus on Engineering and as a result, Sales and Ops stagnates and becomes the blocker to growth.
No slack for when sh*t happens – whether it’s a temporary funk, a personal crisis, or sustained burnout, no extra bandwidth means any life event can endanger the business.
How to make it work:
Focus on sustainability! Successful businesses are not built overnight, so the company needs you to stay healthy.
Invest in an extraordinarily strong support system. While this is important for all founder teams, it’s the most critical for the solo founder. Some possible ideas (pick one at a time to explore and integrate): Executive coaches, therapists, various health & wellness resources (e.g. personal trainer, acupuncture, yoga/meditation, etc.). Quality time with family and friends who have nothing to do with the business.
Ask for help. Too many high-powered people still think asking for help is a sign of weakness. It’s actually a sign of maturity.
“Ask for help. Not because you are weak. But because you want to remain strong.” - Les Brown
Duo (2) Founders
The dysfunction loop: Getting entrenched into a codependent dynamic with rigid roles. Usually comes down to a power struggle pattern that has too *much* or too *little* conflict.
What it looks like:
When the dynamic duo is good, it’s really good – ideally a complementary mix of strengths and weaknesses, on a foundation of trust that allows the pair to build a true partnership and grow together. Unfortunately, the duo is also one of the hardest dynamics to navigate when things *aren’t* going well. As they say, it’s better to be single than partnered up with the wrong person.
Much like a romantic couple, the duo can get trapped in anxious <> avoidant loops. Examples: 1) One founder is more dominant, and the other more passive, but both hold resentments about the roles they play. 2) One founder is focused on fundraising/building the hype, and the other one that’s actually grinding through the day-to-day of the business, again with tension mounting.
Competition for control may show up in unproductive ways, e.g. Dividing up the business into 2 focus areas, then having proxy fights through those functions (e.g. Eng vs. Sales), which devolve into more complicated power struggles involving the teams under them.
How to make it work:
All of the above solutions for Solo founders, AND:
In a duo dynamic, a lot tends to go unspoken/swept under the rug – there’s no 3rd founder to force things to the surface – so it’s even more important to carve out time for the founders to be honest with each other, air out feelings, and actually work through conflict.
The duo’s cycle can get very entrenched, so the key is to interrupt it. Work with a founder coach (I can share referrals). Hire a strong, experienced COO. Both resources, much like a couples therapist, is a neutral third party that’s positioned to focus on the dynamic together. Ideally, you can invest in this early, before the high-stakes pressure makes the conflict untouchable.
Trio (3) Founders
The dysfunction loop: Constant clanning - the human tendency to organize into Us vs. Them groups, which leads to insecurity and infighting that distracts from actual building.
What it looks like:
Much like the “three-body problem” found in physics, the trio is inherently unstable. One is almost always “left out,” while the other two form a binary, with the roles constantly in flux.
Due to the “odd one out” dynamic, unless there’s an extremely solid foundation (as individuals *and* as a trio), insecurities are bound to get surfaced. And these feelings, when unacknowledged and unprocessed, lead to “acting out” behaviors.
Some signs of unproductive behaviors include: Too many 1:1s instead of talking things out as a group. 1:1s that are mostly about passively venting instead of direct conflict. Constant worrying/whispering about what “the other person is doing” and playing social games, trying to “win” the majority to “their” side.
Carving up the different focus areas of the business can become even more contentious. There’s likely to be more problems with unequal skill levels and commitment of the founders. Cap table arguments start to get ugly.
How to make it work:
Even more investment in building emotional honesty and security. Explicit boundaries around 1:1s, e.g. agreement to not talk about the other unless 1) it’s rooted explicitly about work responsibilities or 2) you’re willing to say it to their face from a kind, productive place.
Pay attention to the dynamics, especially because a trio is inherently more complicated than a duo: A duo has just the one “pair,” but within a trio, there’s 3 pairs AND a triple – each with their own unique dynamic and potential for things to go off track.
In order to counteract unproductive 1:1s from taking over, more time must be carved out for the group. (If you think this sounds like a lot of work, wait until you get to the next section, where the true power of exponential growth kicks in…)
4+ Founders
The dysfunction loop: Congratulations! Your brand new startup gets to have politics from day 1 💀
What it looks like:
To be fair, a healthy 4+ person cofounder dynamic *is* possible – but statistically unlikely. The following questions must be addressed early and often: Who actually holds the power? How are decisions made? Where is the accountability? Are we avoiding hard conversations that would lead us to realize we don’t actually need 6 founders?
The dynamic is exponentially more complicated, and people end up spending too much time jockeying for position instead of Doing The Work. There’s even more Clanning and unprocessed feelings that get in the way of productivity.
There’s an explicit purpose to the role of a founder – it entails taking on the greatest amount of risks and committing to building, for the trade-off of future potential rewards. With too many cofounders, power gets too diluted (not to mention the cap table), and so does the commitment. Also, with larger groups, the easier it is for one to be removed by the others – making social games, insecurity, and paranoia even more likely.
Realistically, with 4+ founders, there’s a good chance that ~half will not last for more than a couple of years. Cofounder departures are almost always painful, time-consuming, and inordinately expensive – it’s always worth it to address it early (not unlike a prenup), or better yet, stick to 2-3 cofounders in the first place.
How to make it work:
Within a large founder group, there must be a separate layer that holds the stable power structure: a power layer within the power layer. This is most likely to be a strong CEO who is empowered to be the decision maker, with clear reporting chain and management capabilities to be holding the rest of the group accountable.
Whew. Y’all, I feel so much better having finally written this out – I suppose the observations that led to this post have been a loop in my head. By the time I’m brought into a startup to help with cofounder troubles, the situation is pretty dire. It’s frustrating to think about all the startups’ potential lost because of this, so all the more reason to talk about it. I know it’s hard, but I promise you, NOT talking about it is harder, and you don’t have to do it alone.
As mentioned above, I have a network of trusted executive coaches I can refer to founders, plus my team at Workflow and I specialize in helping startups get ahead of People problems, of which cofounder dysfunction is just one form. Even if you’re not sure what exactly you need, we’re happy to help you figure it out and point you in the right direction.
Overall, everything above is about navigating collaboration and power, with emotional growth at the center of it. Cofounder conflicts, as insurmountable they feel sometimes, are worth facing head-on, because how you address it can become the blueprint for how you approach People challenges as a company, with your behaviors cascading onto every employee you bring on. When the founders have a healthy balanced dynamic, the business will as well. It's the only way to succeed in this new market.
Founders are an extremely ambitious group, and until very recently, that ambition was only applied to Product and Growth. But just as you’re proud of your team’s technical prowess or sales chops, it’s possible to be People-smart and build an exceptional People Organization – it’s what you signed up for. You just have to start.
If you learned something new from this post, please 1) subscribe for more upcoming posts on startup/founder psychology and 2) share with your startup communities.
Jennifer Kim is the CEO/Founder of Workflow, an education and consulting company that trains the next generation of startup leaders on all things Recruiting, People Ops, and DEI. Through its flagship program, the HireEd Accelerator, Jen and her team have taught hundreds of startup leaders to make hiring a competitive advantage. Previously, Jen was Head of People at Lever and was Advisor to dozens of top startups. She is also a Venture Partner at Symphonic Capital, and is known for her hot takes on tech industry and culture as @jenistyping.
