Why Silicon Valley’s Most Popular Rule Is Wrong | Comulate, Jordan Katz & Michael Mattheakis

EOAbout 4 min readAug 7, 2025Watch original
THE SUMMARYAI-generated

Key Concepts:

  • Startup idea generation outside Silicon Valley echo chamber
  • AI-driven automation in the insurance industry back office
  • Importance of product-focused approach over sales-oriented approach
  • Reimagining workflows with AI instead of optimizing existing ones
  • Contrarian thinking and validation through customer interaction

Commulate's Origin and Initial Challenges:

  • The founders, Jordan (CEO) and Michael (CTO), observed a saturation of tech solutions focused on Silicon Valley problems.
  • They identified the insurance industry as ripe for disruption due to its reliance on manual processes.
  • Initial outreach to insurance companies was met with skepticism; one company famously stated, "We don't need your services." This quote was displayed in their office as a reminder.
  • Commulate focuses on transforming the insurance industry with AI, specifically targeting back-office workflows.
  • Three years prior, the idea of automating insurance back-office tasks was considered unconventional.
  • Despite initial skepticism, Commulate has scaled to over eight figures in Annual Recurring Revenue (ARR).

Founders' Backgrounds and Formation of Commulate:

  • Jordan's experience building a complex software platform with 500 features, each only 5% complete, taught him the complexities of software development.
  • He sought to learn product management, inspired by Jackie, who ran product at Asana, and the book "Cracking the PM Interview."
  • Michael joined Brex as the 10th employee and witnessed its rapid growth.
  • He learned from the Brex founders the importance of seeing the business from both a high-level (10,000 ft) and a detailed (10 ft) perspective.
  • Jordan and Michael connected and started working on startup ideas during nights and weekends.
  • Michael left Brex to co-found Commulate with Jordan.

Problem Validation and Customer Discovery:

  • Initially, Jordan and Michael explored ideas based on their experiences at Asana and Brex.
  • They realized that the problems they initially identified weren't as significant as they thought, and existing solutions weren't as bad.
  • They shifted their focus to the insurance industry, specifically accounting workflows, after noticing the extensive use of paper, spreadsheets, and manual data entry.
  • They identified a unique accounting process specific to the insurance industry that lacked automated solutions.
  • Early customer discovery involved numerous Zoom calls to deeply understand customer workflows, edge cases, and existing processes.
  • Their product-focused approach, asking deep questions about workflows, helped build trust with customers.
  • An early customer expressed that Commulate was the first product vendor to truly understand their needs after 50 years in the industry.

AI and Workflow Reimagination:

  • Commulate's approach to AI focuses on reimagining workflows rather than simply automating existing processes.
  • They analyze complex customer processes (often depicted as flowcharts with 30+ steps) and simplify them to 3-4 steps using AI and software.
  • This simplification allows for a fundamental rethinking of how functions are performed.
  • The founders draw a parallel to the web-to-mobile transition, where successful apps (like Instagram) reimagined the user experience rather than simply porting websites to mobile.

Contrarian Thinking and Opportunity:

  • Commulate's initial focus on automating work in vertical industries like insurance was unconventional.
  • The founders advise looking where others don't want to look, as these areas often hold the greatest opportunities.
  • They emphasize the importance of personal validation and understanding of a problem, even if others discourage exploration.
  • The founders believe that AI has opened up a massive opportunity to address the hundreds of billions of dollars spent on manual work in the insurance industry.

Notable Quotes:

  • "We don't need your services." - Early potential customer, now one of Commulate's largest clients.
  • "50 years of working at this company working with you was the first time someone who's brought in a product has ever felt like they understood us" - Early customer.

Technical Terms and Concepts:

  • ARR (Annual Recurring Revenue): A measure of the revenue a company expects to receive from recurring subscriptions in a year.
  • AI Agents: AI-powered systems designed to automate tasks and processes within specific industries.

Logical Connections:

The narrative flows logically from the founders' initial search for startup ideas to their discovery of the insurance industry's inefficiencies. The video connects their backgrounds in product management and engineering to their customer-centric approach to problem-solving. The discussion of AI builds upon the earlier points about workflow complexity and the need for reimagination.

Data and Statistics:

  • Commulate has scaled to over eight figures of ARR.
  • 70% of the most recent Y Combinator (YC) batch is now focused on AI agents for specific industries.
  • Hundreds of billions of dollars are spent on manual work annually in the insurance space.

Synthesis/Conclusion:

Commulate's success stems from identifying an overlooked problem in a traditional industry, deeply understanding customer needs through a product-focused approach, and leveraging AI to reimagine workflows rather than simply automating existing processes. Their story highlights the value of contrarian thinking, customer validation, and a willingness to challenge conventional wisdom in the pursuit of innovation. The founders emphasize that the biggest opportunities often lie in areas that others have dismissed or ignored.

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