#9 – OVERHAULING INSURANCE – COLE WINANS – FLYREEL



When it comes to the founding of insurance industry upstart Flyreel, there’s been nothing quick or easy.

“Everyone reads the TechCrunch article about so and so raising $5 million and it just seems so effortless.  And that just wasn’t our experience at all,” admits Cole Winans, the tenacious founder and CEO of the rising Denver-based startup.  Winans is the latest founder to share his experiences, insights and embarrassments in another revealing episode of Series A-The Podcast.

“Trust me.  People say after your first no it gets easier, but the only thing harder than getting 50 consecutive nos is 51,” he tells host Jim Brisimitzis.

But eventually he started hearing yes, and Flyreel has emerged as a leader in the business and residential space, creating a unique new platform that promises to revolutionize the way everyone’s property and possessions are insured.

Flyreel leverages AI and machine learning to capture and then catalog everything in a business or home.

We’ve learned that a lot of these businesses are insuring properties sight unseen or they have to spend a significant amount time effort and money having to have an inspection done.  It all adds up to a problem where because of the lack of transparency and accountability carriers can’t accurately price premium.  They’re using high level analytics  and predictive modeling to guess the value of these properties and now we just let them know,” Winans says.

Winans and his team were in Redmond recently at Microsoft headquarters for a hackfest where engineers from his company and the Microsoft for Startups team worked feverishly to help prepare the Flyreel platform for scale.

“With your (Microsoft) engineers and the talent that you have internally on leading really the next wave of technology on automation, AI and the like, it’s been a dream,” Winans says of the partnership that leverages the Azure platform.

Winans shares the struggles he faced as a solo entrepreneur, escaping to the solace of rural Missouri to build out his platform after facing a series of rejections.  He offers keen insights on fundraising, hiring his first partner, and working with investors.  He provides a valuable perspective on the burgeoning Denver-area startup ecosystem, and why you don’t need to be on one of the coasts to be successful.  And perhaps most importantly, he discusses trusting your gut.

“One of the things I’ve learned is a lot of people are ready and willing to give you advice, and most of them – even the experts that have been in the space for years – are mostly wrong because your case is different than anyone else’s that they’ve seen,” Winans says.

Listen to the lastest edition of Series A-The Podcast with host Jim Brisimitzis now on iTunes, Google Play, Stitcher or Blubrry.


Leave a Reply

*