On Cofounders: Batman, Robin, and Really Hard Relationships

I've spent a lot of time thinking about cofounders. Who you start with — whether you start with anyone at all — and what happens when a partnership has to grow up alongside the company you're building.

A while back I listened to Hiten Shah, the longtime CEO and cofounder of Crazy Egg, talk about the five companies he's started over the last two decades. One thing he said stuck with me. Across all five, he has preferred to start 50/50 with a partner. Not 51/49. Not "we'll figure out the split later." Fifty-fifty.

His reasoning surprised me a little. He wasn't arguing that cofounders are equal in every moment — he was arguing that leadership is a living thing. On some days, on some problems, one person leads and the other follows. On others, it flips. He calls it the Batman and Robin approach. You are always both. You just take turns about which one you are this week.

That's a very different picture of a cofounder relationship than the one usually pitched in Silicon Valley, where there's a lot of pressure to name the CEO early, draw the org chart, and get the equity split to reflect "who's really driving." The Batman and Robin frame doesn't deny that leadership matters. It just refuses to freeze it. And coming from a multi-time founder who has spent twenty years inside these relationships, it's worth sitting with.

The question before the question

Before you debate the split, though, there's a bigger question: should you have a cofounder at all?

I've built companies every way you can. I've had cofounders. I've gone solo. I've had early employees who were effectively cofounders in everything but the cap table. I've had operating partners, board members, and investors who shaped a company as much as any title-holder. What I know about all of them is the same: these relationships are complex, they take real time, and they evolve — often in ways nobody predicted on day one.

The data doesn't make the choice any easier. Carta has reported that roughly 83% of venture capital dollars go to companies with multiple cofounders.

If your path is venture-backed, the market has a clear preference, and ignoring it has a cost. At the same time, leadership misalignment consistently shows up as a top-three reason companies fail. The same structure that attracts the money is the structure most likely to crack under pressure.

So the honest answer isn't "always have a cofounder" or "go it alone." The honest answer is: choose carefully, and choose for the company you are actually building — not the company a pitch deck template thinks you should be.

What most founders don't realize going in

Here is the part I wish someone had said to me early. Many founders start companies before they have had a meaningful, long-term, committed relationship with anyone other than their parents.

A cofounder relationship asks you to negotiate, accommodate, fight, forgive, and keep showing up — often under financial stress and public scrutiny — with a person you may have known for less than a year before choosing them.

That isn't a character flaw. It's a setup most of us walk into without realizing what we're signing up for. Building a company with someone is, in many ways, the first adult partnership a founder has. It's where you learn how you handle conflict. How you handle fear. How you handle winning. How you handle not winning.

The company is the visible output. The real work is the relationship that produces it.

Choosing the path, the timing, and the partner

When I work with founders now, most of the conversation isn't about product or go-to-market. It's about three choices that quietly determine everything downstream.

1. The path — solo, cofounded, or somewhere in between with a strong early team. Each has a different risk profile, a different financing reality, and a different emotional load. None is inherently better. They just ask different things of you.

2. The timing — some partnerships are right for the idea but wrong for the moment. A partner who's excited about the vision but can't go full-time for another year is a different bet than a partner who's ready to jump today. Neither is wrong. They just aren't the same decision.

3. The partner — this is the one founders rush. Hiten's 50/50 Batman-and-Robin only works if you actually have someone whose values, stamina, and honesty you trust across a decade of weather. Equity is cheap to promise. Trust is not. And the best time to test for trust is before the first wire hits the bank account, not after.

Where I've landed

I used to think the goal was to find the one right answer — the structure that would just work. I don't believe that anymore. I believe the goal is to enter the choice with open eyes: to know why you're choosing a partner (or not), to be clear about what you're asking of them and what they're asking of you, and to build in enough honesty that the Batman and Robin roles can actually switch when they need to.

A founding partnership isn't something you close. It's something you keep choosing.

Your turn

I'd love to hear from you. What's your founder story? Have you gone solo, with a cofounder, or somewhere in between? What has worked, what has surprised you, and what would you do differently if you were starting again tomorrow?

Send me a note — or better, tell me in person on a trail somewhere. Those are still the best conversations.