A group of new angel investors approached me, asking for help evaluating some startups they were considering. They were stunned when I told them the company everyone saw as having the most potential actually had a problem. To be fair, the company had a lot going for it: a clear problem, a compelling solution, and a healthy number of early adopters. But the very thing they were most excited about was my biggest concern: the two founders.
The company was started by two childhood friends. They were roommates at Stanford, still lived together years after graduation, came up with the startup idea together, and quit their jobs together. They were, essentially, the type of founding duo whose lives revolved around cheap burritos and all-night coding sessions.
The angel investors told me the two founders couldn’t be closer – so close, in fact, that they firmly believed their relationship would propel them to success.
I didn’t see it that way.
When Personal Relationships Become Professional Roadblocks #
It’s comfortable and secure to build a startup with a friend. I get it; I’ve been there. My first company was with a friend I’d known since childhood. We spent nearly every weekend at each other’s houses growing up, had inside jokes only we understood, and knew each other’s entire extended families. We literally grew up like brothers. So, theoretically, we were prepared for every demon and monster the startup world could throw at us.
But a startup doesn’t care about your origin story. It cares about 2 AM strategy arguments, pivot plans under investor pressure, and the messes created by delayed feature launches or user churn. These aren’t just technical issues; they’re relationship stress tests. Big ones. And being best friends doesn’t make them any easier.
Frankly, our friendship, far from helping us navigate startup challenges, instead caused us to avoid them, because those challenges ceased to be merely startup challenges. They became deeply personal relationship challenges. Think about it: when your co-founder is also your best friend, a simple “no” or “not yet” can easily stop being strategic advice and start feeling like a personal attack.
For example, I remember my best friend/co-founder and I argued dozens of times over product interface design, and each time it ended in arguments. Of course, it was supposed to be a professional disagreement, but I assure you, at the time, I also felt personally betrayed.
Ultimately, I couldn’t tell if I was mad about the product choice itself, or mad that someone who was supposed to be my best friend wasn’t supporting or trusting me. That’s no way to run a startup. And that’s the core risk of founding with a friend: Friendship magnifies mistakes because founders struggle to separate professional friction from personal identity. You don’t get pure conflict; you get feedback steeped in emotional baggage. You get increasingly blurred lines, and the higher the stakes, the blurrier those lines become.
Why Friction Trumps Friendship #
By the way, this isn’t just my personal experience. Yes, my startup with my best friend was challenging, but I’ve also seen dozens of other early-stage teams fall short this way. What might start in high spirits – “We finish each other’s sentences!” – often quickly devolves into avoidance: avoiding difficult conversations, avoiding performance reviews, and avoiding decisions that might make the other person feel sidelined, undervalued, or, worst of all, expendable.
Simply put, when your startup relies on someone you love like family, you can’t make objective decisions. You make protective decisions. And protective decisions kill companies.
In fact, your interactions with a co-founder should be the complete antithesis of “protective.” That’s because a good co-founder relationship is defined more by “friction” than “friendship.” Friction sharpens the team and makes the company better. You need a co-founder who will challenge you, see your blind spots, bang on the table at a meeting with you, and tell you that the feature you’re proud of is stupid. You need someone who wants what’s best for the company, not just what’s best for you. Most importantly, you need to be fully capable of offering the same level of critical collaboration to your co-founder.
This means that finding a co-founder is about finding the right person to build a company with… not your favorite person to get pizza with. Stop thinking about whether you’d swipe right on Tinder and start thinking about whether you can match each other’s work ethic and passion for the problem at hand.
I guarantee you, the greatest co-founder partnerships in startup history weren’t forged at summer camp or late-night bar crawls. They were born in accelerators, hackathons, or from a shared obsession with a particular market or problem. These relationships are built on mutual respect, complementary skills, and a clear understanding of roles and responsibilities.
When these co-founder relationships work, they are incredible. Often, they are even more beautiful than the closest friendships because, beyond the extreme commitment, they are also deeply professional. They not only gel temperamentally but, more importantly, are aligned in their mission, and that alignment allows them to weather storms that would sink most friendships. Because in a startup, the most important thing isn’t how much you like your co-founder. It’s how well you can work together when things go wrong. And remember, in a startup, something big will always go wrong.
That’s not a hypothetical. That’s a guaranteed certainty.
So, while a deep bond between co-founders sounds great in theory, what really signals potential is co-founders with a burning passion for what they’re building. When you find that, you know they actually have a shot at making it work.