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EO StudioHow to Find $10M+ Ideas in Markets We’d Never Worked In | Comulate, Jordan Katz & Michael Mattheakis
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At a glance
WHAT IT’S REALLY ABOUT
How Comulate found an eight-figure AI wedge in insurance back-office
- Comulate’s founders deliberately avoided the saturated “solve your own tech problems” playbook and instead hunted for neglected pain in insurance back-office and accounting workflows.
- They broke into a skeptical, relationship-driven industry by doing deep product-style discovery calls, mapping real processes, and earning trust through domain understanding rather than salesmanship.
- Early rejection (“we don’t need your services”) became signal—not truth—once they gathered broader evidence, persisted, and later converted that same skeptic into a major customer.
- They argue the best AI products come from questioning why workflows exist and removing outdated constraints, simplifying 30-step flowcharts into a few steps instead of automating every legacy edge case.
- The broader thesis is that vertical, historically under-software industries contain hundreds of billions in manual work, making them prime terrain for AI-driven transformation over the next decade-plus.
IDEAS WORTH REMEMBERING
5 ideasGo where tech isn’t already overfishing for problems.
They believe “solve your own problem” concentrates founders in the same tech-native pain points; looking in industries like insurance reveals abundant, underserved operational problems.
Treat early skepticism as a data point, not a verdict.
The dismissive “we don’t need your services” call initially shook them, but more interviews revealed the problem was real—sometimes a stakeholder just isn’t exposed to the pain.
Win traditional industries by leading with product depth, not a pitch.
Their advantage was asking detailed workflow and edge-case questions, which built credibility and led customers to feel understood—unlocking early champions.
Map the whole workflow before you build anything substantial.
They invested heavily in Zoom-based process discovery, often producing complex flowcharts; this grounded product decisions in reality rather than assumptions from outside the domain.
AI’s biggest payoff is simplification, not automation of complexity.
Instead of encoding a 30-step legacy process into software, they look for which steps existed due to old constraints and compress the process into 3–4 steps using modern software and AI.
WORDS WORTH SAVING
5 quotesSo there's a popular belief in Silicon Valley of the best way to find startup ideas is to try to solve your own problems. But if everyone in the tech industry is following that path, it leads to this saturation of problems for folks in the tech industry. That's what led us to the insurance industry. Quickly realized there's unsolved problems everywhere.
— Michael Mattheakis
The f- first thing I hear is, "You know, I just wanna tell you, you know, I'm taking this call as a favor, but we don't need your services. We have solved for this already. We're all set. I'm just trying to do this as a favor."
— Jordan Katz
And that company that told us, "We don't need your services," is now one of our largest customers.
— Michael Mattheakis
I think the real question is about, like, what fundamental constraints created these workflows in the first place, and do those constraints actually, like, still exist?
— Jordan Katz
I think the biggest advice I have is, like, look where others don't wanna look.
— Jordan Katz
SPEAKERS
Michael Mattheakis
guestCTO and co-founder of Comulate; former engineer at Brex.
Jordan Katz
guestCo-founder and CEO of Comulate, focused on applying AI to insurance workflows.
High quality AI-generated summary created from speaker-labeled transcript.
