EO StudioHow to Find $10M+ Ideas in Markets We’d Never Worked In | Comulate, Jordan Katz & Michael Mattheakis
CHAPTERS
- 0:00 – 0:58
Escaping “solve your own problems” saturation by going where tech isn’t looking
The founders challenge the Silicon Valley mantra of only building for your own pain points, arguing it concentrates startups in the same narrow set of tech-industry problems. They explain why that logic pushed them toward insurance—a space full of unsolved, high-friction workflows.
- •“Solve your own problem” can lead to idea saturation inside tech
- •Big opportunities exist in industries that software hasn’t modernized
- •Insurance stood out as a domain with pervasive inefficiencies
- •Outsider perspective can reveal overlooked pain points
- 0:58 – 1:32
Comulate’s contrarian bet: AI for insurance back-office workflows
Jordan introduces Comulate and frames the initial skepticism: two founders with no insurance background trying to automate back-office insurance operations. He contrasts that early doubt with the company’s traction, reaching eight figures of ARR.
- •Positioning: transforming insurance operations with AI
- •Initial narrative sounded implausible to incumbents
- •Focus on back-office workflows rather than flashy front-end experiences
- •Traction milestone: scaling to 8-figure ARR in ~3 years
- 1:32 – 2:02
Learning product the hard way: from overbuilt side project to PM craft
Jordan recounts building an overly complex product in college and realizing that great software requires discipline and craft. This pushes him toward product management and a deliberate apprenticeship mindset.
- •Early product attempt: too many features, nothing finished well
- •Realization: building great software is harder than it looks
- •Discovery of product management as a path to mastery
- •Intentional learning as a precursor to entrepreneurship
- 2:02 – 2:58
Targeted apprenticeship at Asana—and meeting a future co-founder
Jordan describes choosing Asana specifically to learn from strong product leadership. He then explains meeting Michael and recognizing uncommon founder potential in an early conversation.
- •Choosing a job as a learning vehicle, not just employment
- •Seeking mentorship and high-caliber product environment
- •First meeting signals strong founder compatibility
- •Early founder “pattern recognition” before any idea exists
- 2:58 – 3:58
Michael’s Brex lessons: pairing 10,000-foot strategy with 10-foot execution
Michael shares what he learned during Brex’s rapid scale from ~10 people to hundreds. He emphasizes the rare ability to hold long-term ambition and weekly execution details simultaneously.
- •Brex scaling experience as formative founder training
- •Duality: big vision (massive company) + tactical growth/feature execution
- •Importance of product/design detail alongside strategy
- •Why this operating model matters in early-stage startups
- 3:58 – 4:34
Choosing the moment: leaving Brex to start building together
Michael explains how the timing aligned—Jordan leaving Asana, their growing conviction, and nights/weekends experimentation. The chapter closes with Michael committing to the leap into entrepreneurship.
- •Iterating on ideas part-time before quitting jobs
- •Momentum from friendship and repeated founder conversations
- •Timing and personal readiness as key decision factors
- •Transition from exploration to full-time commitment
- 4:34 – 5:35
Breaking into an unfamiliar industry: rejecting weak ideas and discovering insurance accounting pain
The founders explain that their initial ideas didn’t hold up under customer validation. As they explored insurance, they found intense reliance on paper/spreadsheets and uncovered a uniquely complex accounting layer with little automation.
- •Customer discovery invalidated their first set of ideas
- •Insurance workflows: heavy manual transfer between analog and legacy systems
- •Accounting emerged as the highest-leverage wedge
- •Observation: insurance has an extra “type” of accounting others don’t
- 5:35 – 6:45
Earning trust as outsiders: skepticism, setbacks, and deep workflow interrogation
Jordan recounts early calls where industry contacts dismissed them as a favor-taking distraction. Michael explains how they reframed the rejection, kept gathering evidence, and invested heavily in Zoom-based process understanding.
- •Cold start problem: outsiders lack credibility and access
- •Early dismissals can feel like existential signals
- •Rejections may reflect limited internal visibility, not lack of need
- •Persistence via continuous customer conversations and evidence-building
- 6:45 – 8:07
Product-led discovery as a trust engine: understanding edge cases better than vendors
They argue their advantage was approaching customers as product builders, not salespeople. By asking detailed questions about workflows and edge cases, they built unusually strong trust and domain understanding, leading to early champions.
- •Product mindset: diagnose deeply before proposing solutions
- •Edge-case curiosity builds credibility in complex operations
- •Customer quote: first vendor who truly “understood us”
- •A few champion relationships can bootstrap early product-market fit
- 8:07 – 8:43
From “we don’t need this” to a top customer: persistence compounds
Michael revisits the original rejection and reveals the twist: that same company became one of Comulate’s largest customers. The founders emphasize the value of persisting through ambiguous early feedback while building bottoms-up conviction.
- •Early negative feedback isn’t always predictive
- •Bottoms-up confidence comes from many data points, not one call
- •Markets can “wake up” to the need as you clarify and prove value
- •Long sales cycles and shifting awareness reward persistence
- 8:43 – 9:16
Applying AI to the right problem: challenge the constraints that created the workflow
Jordan reframes AI opportunity: not just speeding up existing processes, but questioning why the process exists at all. The focus shifts to identifying outdated constraints and redesigning the workflow accordingly.
- •AI shouldn’t only optimize legacy workflows
- •Key question: what constraints originally shaped the process?
- •Determine whether those constraints still exist in an AI era
- •Reimagining the function creates larger advantage than incremental automation
- 9:16 – 10:42
Platform-shift playbook: simplification beats mapping complexity into software
Michael compares the AI shift to web-to-mobile: winners redesign for the new platform rather than porting old patterns. He describes mapping customer processes into complex flowcharts, then using software/AI to collapse them into a few steps.
- •Analogy: mobile winners redesigned experiences (not web-porting)
- •AI shift similarly enables new primitives and workflows
- •Process mapping reveals unnecessary complexity
- •Product strategy: reduce 30-step flows to 3–4 steps via automation
- 10:42 – 11:51
Why vertical AI is exploding now—and how to find $10M+ opportunities
Michael notes that vertical workflow automation was once uncool but is now popular (e.g., AI agents for every industry). Jordan advises founders to look where others avoid, validate in the field, and seek the truth directly rather than relying on consensus.
- •Vertical AI impact is highest in software-neglected domains
- •Trend evidence: many new startups targeting “AI agents for X”
- •Advice: explore spaces others dismiss; contrarian discovery matters
- •Don’t outsource belief—do firsthand validation and customer work
- 11:51 – 12:48
The long-run prize: hundreds of billions in manual work and a decade-plus opportunity
They close by framing the scale of the opportunity: enormous spend on manual insurance operations and a multi-decade software wave driven by AI. The chapter ends on optimism about being early in a massive transformation.
- •Manual work in the space totals hundreds of billions annually
- •AI opens automation possibilities previously out of reach
- •Comulate aims to be at the forefront of the shift
- •Framing: one of the biggest opportunities in the next 10–20 years
