What if insurance isn’t actually about protection—but about who understands risk better than anyone else?

Tanner Hackett has spent his career at the edge of massive shifts—helping build Lazada into Southeast Asia’s e-commerce backbone, then co-founding Button to ride the mobile commerce wave. Now he’s the founder and CEO of Counterpart, an insurtech company rebuilding small business insurance with AI-driven underwriting, real-time risk insights, and a growing dataset across 35,000+ policies.

In this episode, Tanner breaks down why insurance—one of the largest financial markets in the world—still runs on outdated assumptions, and how Counterpart is quietly rewriting the math.

In Today's Episode We Discuss:

00:01 – Introduction and Tanner Hackett Background

00:33 – Early Career: Lazada and Southeast Asia E-commerce

01:30 – Building Button and Mobile Commerce Insights

02:03 – Founding Counterpart and Shift to Insurance

02:19 – Initial Idea: HR Tech to Insurtech Pivot

04:11 – What’s Broken in Insurance Today

06:15 – Why Previous Insurtech Startups Failed

08:16 – Understanding MGA and Insurance Business Model

09:16 – Why Now Is the Right Time for Counterpart

11:49 – Rethinking Value in Insurance

13:07 – Insurance Categories Counterpart Focuses On

17:28 – Distribution vs Underwriting Bottlenecks

19:45 – Data Advantage and Underwriting at Scale

21:25 – Insurance Basics for Startups

27:02 – Counterpart’s End-to-End Platform Approach

29:28 – AI, Data Infrastructure, and Pricing Risk

33:48 – Building a Data Moat in Insurance

35:10 – Founder Advice: Reducing Risk and Lowering Premiums

38:05 – Real-World Claims and Insurance Stories

39:21 – Fintech and HR Tech Companies Tanner Admires

40:58 – Long-Term Vision for Counterpart

42:29 – Closing Thoughts and Future of Insurance

“Insurance is a math problem—but most of the industry is still pricing to averages.”

“Every dollar paid out on a bad claim gets passed on to the next customer. That’s the system we’re fixing.”

Tanner’s journey started with marketplaces and marketing tech. Now he’s building a company where the product isn’t just coverage—it’s understanding risk at a level traditional insurers never could. Because in the end, the companies that win in insurance aren’t the ones with the biggest balance sheets. They’re the ones who see the risks others miss.

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