He hired exactly right — and still lost 3 months of runway

Series A company Rillet launched in 2024 and is growing fast: 5x revenue growth and nearly 200 customers including Windsurf, Decagon and Postscript.

But the accounting startup’s real competitive advantage might be how quickly co-founder Nicolas Kopp learns from expensive mistakes. 

His early bet on domain expertise over startup experience cost the company 3 months of runway — time he quickly converted into a systematic approach for when contrarian hiring works and when it doesn't. 

In this issue, Nicolas examines why a thoughtful, first-principles decision can still cost founders — and how to build safeguards that turn expensive lessons into lasting value.

The principle ⚛️

When first principles thinking backfires  

One of Nicolas Kopp’s first hires at Rillet, an AI native accounting platform, looked great on paper.

They were a former auditor and knew the accounting world well. They had deep ERP experience. They lived their customer’s workflows and breathed their pain points. 

Kopp brought them on to help with go-to-market under the assumption that if they understood the customer, every other facet of the job could be taught. 

But once in the role, it became clear that customer empathy alone wasn't enough. "They weren't fast enough at ramping up to some of the technical aspects of the job — like how to write a good cold outbound email and what tools to use there," Nicolas says.

When it became obvious the hire wasn't working, Nicolas faced a brutal reality: let them go and start the search over, or keep burning runway on someone who couldn't keep pace. He chose to cut losses, but the damage was done — three to four months of company lifecycle lost to a carefully reasoned plan that still missed the mark.

This wasn't poor judgment — Nicolas had done everything right. He identified a problem, developed a thesis, and executed thoughtfully. Unfortunately, the cost of being wrong as a founder is measured in time, not money. And running out of time kills startups.

When contrarian hires do work

Here's what makes startup decision-making so maddening: the same logic that failed in one context succeeded brilliantly in others. Nicolas's domain-first approach eventually produced some of Rillet's strongest performers:

• Former accountant → Head of Product: Learned to run research calls, write specs, and lead engineering — all on the job. Her background also helped engineers get closer to customers, simply by proximity.

• Ex-auditor → Head of CS: Deep domain knowledge + a knack for translating customer feedback made her a CS standout.

• Finance hire → Content lead: A natural writer who now drives Rillet’s LinkedIn strategy.

What helped these bets pay off 

What’s especially interesting about Nicolas is that most founders would have abandoned the domain-first approach after losing three months of runway. Yet he didn't. 

Instead of compromising his thesis that customer empathy beats functional skills, Nicolas doubled down — but this time with systems to accelerate the transformation.

Here’s a look at what made a difference the second time around.

🛠 Train in real time, not in theory

When one early hire stepped into a product role without prior experience, Nicolas didn’t hand her a guidebook — he showed her how to lead research calls live.

“We didn’t just talk about the process — I did the first calls with them,” he says. “I showed what good looked like, then stepped back and coached live. That’s what it takes.”

🧭 Coach, don’t cheerlead

“You need to give that person a lot of support,” Nicolas says. “Less in a parental way of cheering them on all the time. Moreso, if something is not great, we'll talk about it and we'll try and make you successful in this new role.” 

 🍕 Feed your hungriest workers

“Think about ‘what is the next project I can pull that person in?’ If they're hungry, if they're fast, if they have a really steep slope, keep an eye and scout for new projects that constantly push their boundaries a little bit as well,” he says. 

The pre-mortem: Questions to ask before going contrarian

The real lesson isn't about hiring tactics — it's about building decision-making systems that account for what you can't see. Even well-reasoned bets carry hidden costs, and the best founders learn to price them in.

If you’re considering a nontraditional hire:

• Do I have at least 3 months of runway to let this person ramp?

• Am I betting on someone to scale a system — or invent one from scratch?

• Will I know within 30–60 days if it’s working?

If the answer to any of these is no, you may not be betting — just hoping.

Listen to the full episode

Want the full story? Nicolas shares what worked, what didn’t, and what he’d do differently next time on “How I Screwed This Up.” 

→ [Link to episode]

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