The Reasoning Show
The Reasoning Show AI moves fast. Thinking clearly matters more.
The Reasoning Show cuts through the hype to explore how the smartest people in enterprise AI actually make decisions — the strategy, the tradeoffs, and the hard lessons no press release mentions.
Every week, hosts Aaron Delp and Brian Gracely sit down with the founders building the tools, investors funding the shift, and operators running AI in the real world. Not hype. Not panic. Just clear-headed conversations with people who have to make actual decisions.
Because the AI revolution isn't just happening. It's being reasoned through.
New shows every Wednesday and Sunday.
Topics: Enterprise AI strategy · LLMs in production · AI leadership · Agentic AI · Digital Sovereignty · Machine Learning · AI startups · Cloud Computing
The Reasoning Show
(Part I) MetLife Digital Accelerator Powered by TechStars
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Brian talks with the founders from Buddy, Enroll Hero and FitBliss, as part of a behind-the-scenes engagement with TechStars and the MetLife Digital Accelerator in Cary, NC. This show is Part 1 of a series of interviews with companies that are innovating and disrupting the insurance industry, in cooperation with corporate partner MetLife in Cary, NC.
Show Links:
Show Notes:
Company 1: Buddy
[Update] Has a signed reinsurance commitment from their Lloyd's syndicate, so their product is fully backed
CEO: Charles Merritt
Richmond, VA
On-demand accident insurance to enable people to explore the world and have adventures.
- Adventure/outdoor people
- Extreme sports
Company 2: Enroll Hero
[Update] Secured pilots with MetLife and Northwestern Mutual
Founders: Mark Lee and Bryan Kocol
Santa Monica, CA
Helping people make it easier to get the right Medicare
“The TurboTax for Medicare”
- 10,000 people a day are turning 65
- Direct to consumer business; challenges of building trust
- “Total costs of care” vs. “Monthly Premium” costs
Company 3: FitBliss
[Update] Closed Salesforce as a customer and 10x'ed their revenues
CEO: Navid Rastegar
San Francisco, CA
"Optimize Well-Being and Productivity"
- Integrate with many devices and services
- Like a personal trainer or financial planner for well-being
- Both an employee and employer tool
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