Video: Flyreel Transforms the Insurtech Landscape with AI

Cole Winans, founder and CEO of Flyreel, describes what goes into scaling a startup from a desk and two people to a technology-based business that is changing how insurance does business.

A hockey player and software engineer, Cole shares the ups and downs and lessons learned from building a consultancy practice to building a company that now employs nearly two-dozen people.

In one of our most open founder discussions yet, Cole talks about the euphoria of gaining that first angel investor. He candidly discusses the dark days of pivoting away from two great solutions that wouldn’t monetize. He shares how his flooded basement confirmed Flyreel’s claims AI assistant’s market potential and more.

  • There are many benefits of being a curious generalist turned entrepreneur wearing many hats.
  • Growing 10X, from two people to twenty over 18 months, makes open and regular communications 100X more critical. Employees need to know the CEO as a person, not as a title.
  • It is the world’s worst feeling to potentially risk losing money from people who trusted and believed in you.
  • But—if you keep pushing and creatively pivot, listen to customers, and keep communicating to your investors at every turn, you can build a better product and a better business that turns a profit.
  • Learn how Flyreel is building a culture based on humility, where people take their work seriously, but not themselves.



Cole Winans, CEO and founder of Flyreel, is a self-taught technologist and entrepreneur who launched and sold his first technology business at age 14. Prior to Flyreel, he developed and deployed more than 100 successful enterprise and consumer software products and applications. His expertise extends to mobile technology, artificial intelligence (AI), computer vision, and cloud application development.


Flyreel sells solutions to property and casualty insurance companies for underwriting, claims, and risk management. An AI assistant guides home and business owners through their own home inspection for insurance applications. Flyreel helps insurance carriers better understand the property to serve customers. Flyreel identifies critical risks and hazards that are important to both the carrier and the property owner.