Pitch the Ceiling: James Hawkins on Ambition and Building PostHog

Here is something that nobody tells you when you are building a business: the version of your idea that makes you nervous to say out loud is often the version worth saying.

James Hawkins figured this out mid-flight. He is the CEO of PostHog, a software company that went through five failed ideas before finding the one that stuck, and he said something at a Y Combinator session in Paris recently that I keep turning over. "At the start we were almost apologetic," he told the audience. "We were trying to find a little place in the market, hiding away from other companies that were bigger than us." Then they stopped doing that. And things got easier, not harder.

That is a counterintuitive enough claim that it deserves some unpacking. But before we get to the argument about ambition — which applies well beyond the startup world — there is a partnership story here that I think matters more.

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Hawkins runs PostHog with his co-founder Tim. When they started out, they divided responsibilities the way most founding teams do: Hawkins was CEO because he had a sales background, Tim was CTO because he was the technical one. Logical. Clean. Also wrong.

After a while, Hawkins noticed he was gravitating toward product decisions and getting restless on the sales side. Tim was having the mirror experience — anxious about what was happening in sales, energized when he got to operate like a system-builder. They had each drifted toward each other's lane without quite meaning to.

Their solution was to just swap. Officially. No drama, no months of deliberation. Hawkins took product. Tim took sales. "We both had tons of energy," Hawkins said. "It's like a new job. And we just both went much harder."

What strikes me about this is not the swap itself — it is the trust that made the swap possible. Two people who knew each other well enough to say, you are better at my job than I am, and I am better at yours. That is not a structural decision. That is a relationship decision. And it is the kind of thing that only works if the partnership is solid enough to survive a little ego exposure.

Hawkins also described a more recent division of labor, when he decided PostHog needed to go all-in on AI and needed one person to drive it without distraction. Tim took over everything else — finances, hiring, operations — so Hawkins could focus entirely on building with the engineering team. "I didn't have to worry about anything else," Hawkins said. "I didn't do any one-on-ones or anything like that. I just kind of randomly did off-sites or met up with engineers to get them to build things with me."

That arrangement requires a level of mutual trust that most business partnerships never develop, because most business partnerships never get tested that way. One person essentially says: I will hold the entire company together while you chase the thing you believe in. And the other says: I believe in it enough to let you do that.

I have watched a lot of small business partnerships over the years, and the ones that break almost always break on a version of this moment — when one person wants to go big and the other wants to stay safe, or when neither person is willing to give the other room to be fully themselves inside the business. Hawkins and Tim apparently solved this by treating their roles as tools rather than identities. You pick up the tool that fits the job. You put it down when it stops fitting.

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Now to the ambition argument, which Hawkins made plainly and which I think holds up outside the startup context.

The intuition most founders and small business owners carry is that a modest, achievable idea is easier to sell — to investors, to partners, to early customers — because it seems more credible. You are not overselling. You are being realistic. You are protecting yourself from embarrassment if it does not work.

Hawkins says this instinct is backwards, at least in terms of what actually happens when you pitch. Smaller ideas, he argues, are harder to get people excited about. The person you need to convince is always asking, consciously or not: Is this worth my attention? Is this worth my money? Is this worth my time? A modest idea gives them easy reasons to say no. A genuinely large idea reframes the question.

"If you're more ambitious, you're more remarkable," he said. "If something is remarkable, people will remark upon it — you get word-of-mouth growth. If what you're building is unremarkable — a really narrow point solution — you can definitely still be successful, but you have an easier time if you're building something that is fundamentally more compelling."

The marketing logic here maps directly onto Main Street. Think about what made the independent bookstore down the street survive when the chain next door closed. It usually was not that the bookstore was playing smaller — it was that they were doing something so specific and committed that people talked about it. The curated kids' section. The Friday author readings. The staff picks that actually reflected real taste. Remarkable. People remarked upon it. The cautious play — keep the inventory broad, compete on price, stay out of trouble — that is the one that does not survive.

The flip side of Hawkins' argument, which he was honest about: bigger ambition means a more bimodal distribution of outcomes. The investors who want safe and modest will be less interested. The ones who want transformational will be more interested. You are not making fundraising universally easier; you are sorting for a different room.

That is probably worth knowing before you decide how to frame the big ask.

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There is a cultural layer to this conversation that Hawkins got into when talking about European versus American founders, and it is uncomfortable in the right way. He observed that European founders — he is British — tend to ask themselves what if it fails? where American founders tend to ask what if it works?

He is not the first person to make this observation, and it is not universally true. But I think the underlying point lands beyond geography: most people who are building something calibrate their stated ambitions downward before they even open their mouths, because they are pre-managing someone else's reaction. They are already having the argument they imagine they will lose.

"You're just default screwed as a startup," Hawkins said. "So it is all upside. You just can't win on downside."

That framing — you are probably going to struggle anyway, so you might as well swing big — is not nihilism. It is actually a pretty grounded risk calculation. If you are going to take on the work and the risk and the sleeplessness of building something from nothing, the incremental cost of going after something larger is usually smaller than people think. And the potential return is not.

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PostHog's own story is an interesting data point here. They pivoted five times before landing on the product that worked. Four or five rejected ideas, each one tested in weeks rather than years — Hawkins described chasing one potential customer across multiple trains and a bus for a $300-a-month contract, just to learn that the customer would never pay more than that. That information was worth the trip fare. They moved on.

What they eventually built was ambitious enough that PostHog's software can now, in some cases, detect a problem in a product and fix it before anyone on the team knows the problem exists. Whether that lands for you as remarkable or unsettling probably depends on where you sit. But nobody ignores it. That is the point.

The ambition did not make the path shorter or the work easier. It made the work worth remarking on.

And I think that is the actual answer to the question most founders, and most small business owners, are really asking when they stand at the edge of the bigger idea: not can I do this? but is it okay to want this?

From what Hawkins described, the answer appears to be yes — and also, it turns out, strategically useful.

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Dorothy "Dot" Williams covers small business and entrepreneurship for Buzzrag.