AI and ML, Climate Risk, Startup, MGA, InsurTech, Construction Insurance, Renewable Energy
Gilad Shai
Episode 162 — Justin Levine, Co-Founder & ...

ustin Levine started as a civil engineer, ran risk management for a major New York City contractor, sold a construction tech startup, and spent time at Autodesk watching contractors generate data that no insurer was using. That gap became Shepherd. In Episode 162, Justin explains why the AI infrastructure boom is fundamentally a construction insurance problem, how Shepherd rewards contractors for technology they are already using to deliver up to 25% lower premiums, and why the Coalition-Allianz deal is the first real proof point that the InsurTech underwriting thesis is not just talk.

Episode 162 — Justin Levine, Co-Founder & CEO of Shepherd
Brokerage, MGA, MGU, AI and ML, Distribution, M&A
Gilad Shai
Curtis Barton, CEO of ALKEME

Curtis Barton started Alkeme in October 2020 with seven agencies, $25 million in combined revenue, and a simple argument: stop running a lifestyle business and start building generational wealth. Five years later Alkeme is at $350M+ in revenue, 35 states, 110+ locations, and 85+ acquisitions. In Episode 160, Curtis explains why most consolidators are more overleveraged than they admit, why organic growth is the only honest metric in the rollup game, and why every insurance brokerage — whether it wants to or not — is becoming a software company.

Curtis Barton, CEO of ALKEME
AI and ML, Claims Management, Claims, Agentic AI, Workers Comp, Startup, Founder
Gilad Shai
Heather Wilson, CEO of CLARA Analytics

A finger cut came in as a severity one workers comp claim. Nobody looked at it for 90 days. CLARA's models kept reading the incoming medical documentation — and caught the trajectory shift before any human did. By the time the alert fired, the case was heading toward amputation, not a bandage. In Episode 159, CLARA Analytics CEO Heather Wilson explains how claims AI actually works in practice: not as a replacement for adjusters, but as a 24/7 safety net that catches what tired eyes miss — and what she wants to accomplish before she leaves this industry: finally connecting the claims intelligence that closes cases to the actuarial intelligence that prices them.

Heather Wilson, CEO of CLARA Analytics
Parametric Insurance, MGA, Climate Risk, Reinsurance, Carrier, AI and ML
Gilad Shai
Sid Jha, CEO of Arbol

Sid Jha didn't come from insurance — he came from Citadel, trading commodities, pricing weather risk. In Episode 158, he explains how that background shaped Arbol's thesis: that parametric insurance wasn't just a claims shortcut, but a bridge to entirely new pools of capital that traditional insurance could never access. We also get into why Arbol stopped being a pure parametric company — and why being ideological about your product is the fastest way to miss what the customer actually needs.

Sid Jha, CEO of Arbol
Agent Technology, Brokerage, Core System, AI and ML, Agentic AI
Gilad Shai
Anupam Gupta, CPO at Applied Systems

AI won’t replace insurance brokers.

But it will change how their work gets done.

In Episode 148, I spoke with Anupam Gupta, Chief Product Officer at Applied Systems, about how AI is transforming the brokerage tech stack.

One idea stood out:

Instead of replacing humans, AI will become digital teammates working behind the scenes.

For example:

• AI agents preparing renewal packets
• Extracting data from submissions and emails
• Comparing carrier responses
• Surfacing missing coverages

The result?

Less administrative work.
More time for brokers to do what actually matters: advise clients.

One of my favorite lines from the episode:

“Imagine every employee showing up like your top 10%.”

That’s the real promise of AI in insurance.

Anupam Gupta, CPO at Applied Systems

Distribution

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Will Johnson, CEO and Co-Founder of Gyde

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Will Johnson, CEO and Co-Founder of Gyde

Will Johnson spent a decade at Oscar Health watching brokers — the most important node in health insurance distribution — get chronically underinvested in technology. In Episode 153, he explains how Gyde is fixing that: an AI-powered operating system combined with an acquisition-based partnership model that aligns incentives completely and brings a dedicated team into agencies post-acquisition to actually build the growth infrastructure together. The insight at the core of it is simple: most brokers are spending less than half their time on new business. Gyde exists to change that ratio.

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InsurTech Under Fire — Resilience, Insurtech, and the Future of Insurance with Kobi Bendelak

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InsurTech Under Fire — Resilience, Insurtech, and the Future of Insurance with Kobi Bendelak

InsurTech Israel CEO Kobi Bendelak crossed a desert, a border, and two countries to make it to InsurTech Insights London — during wartime. In Episode 151, he shares what that journey says about Israeli startup culture, how the InsurTech industry has matured from tech tourism to serious procurement, and why he believes core systems may be obsolete within a few years.