How to Find $10M+ Ideas in Markets We’d Never Worked In | Comulate, Jordan Katz & Michael Mattheakis

They built a multi-million dollar AI company by going against Silicon Valley's playbook. Jordan (CEO) and Michael (CTO) are the co-founders of Comulate — a startup that’s quietly transforming the insurance industry using AI. While most founders try to solve their own tech-world problems, they went the other way — diving into a space full of outdated workflows, skepticism, and "we don’t need your services" pushback. That same company that rejected them? Now one of their largest customers. This is a story about building genuine product-market fit, uncovering overlooked problems, and simplifying complexity with AI — all by listening more deeply than anyone else in the field. Are you chasing what’s trendy — or actually solving a real problem? 00:00 Intro 01:26 How to Know Someone’s the Right Co-founder 04:27 How to Break Into an Unfamiliar Industry 08:37 Applying AI to Solve the Right Problem EO stands for Entrepreneurship & Opportunities. As we're looking to feature more inspiring stories of entrepreneurs all over the world, don't hesitate to contact us at partner@eoeoeo.net LinkedIn | @EO STUDIO X | @eostudi0 Instagram | @eostudio.official Substack | @eostudio

Michael MattheakisguestJordan Katzguest

Aug 7, 202512mWatch on YouTube ↗

EPISODE INFO

Released: August 7, 2025
Duration: 12m
Channel: EO Studio
Watch on YouTube: ▶ Open ↗

EPISODE DESCRIPTION

They built a multi-million dollar AI company by going against Silicon Valley's playbook. Jordan (CEO) and Michael (CTO) are the co-founders of Comulate — a startup that’s quietly transforming the insurance industry using AI. While most founders try to solve their own tech-world problems, they went the other way — diving into a space full of outdated workflows, skepticism, and "we don’t need your services" pushback. That same company that rejected them? Now one of their largest customers. This is a story about building genuine product-market fit, uncovering overlooked problems, and simplifying complexity with AI — all by listening more deeply than anyone else in the field. Are you chasing what’s trendy — or actually solving a real problem? 00:00 Intro 01:26 How to Know Someone’s the Right Co-founder 04:27 How to Break Into an Unfamiliar Industry 08:37 Applying AI to Solve the Right Problem EO stands for Entrepreneurship & Opportunities. As we're looking to feature more inspiring stories of entrepreneurs all over the world, don't hesitate to contact us at partner@eoeoeo.net LinkedIn | @EO STUDIO X | @eostudi0 Instagram | @eostudio.official Substack | @eostudio

SPEAKERS

Michael Mattheakis
guest
CTO and co-founder of Comulate; former engineer at Brex.
Jordan Katz
guest
Co-founder and CEO of Comulate, focused on applying AI to insurance workflows.

EPISODE SUMMARY

In this episode of EO Studio, featuring Michael Mattheakis and Jordan Katz, How to Find $10M+ Ideas in Markets We’d Never Worked In | Comulate, Jordan Katz & Michael Mattheakis explores 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.

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