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
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Troy Korsgaden - Inflection Point

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Troy Korsgaden - Inflection Point

In this episode, Troy Korsgaden and I talk about his latest book, "Inflection point," and his experience consulting insurance agencies and insurance carriers and other life hacks. Troy started his insurance career in 1983. He has instructed and spoken with hundreds of thousands of executives, agents, brokers, and staff members. He authored six books promoting his mission to help the insurance industry to wake up to the radical transformation that is taking place.

Don't put the sale first, don't put the commission first. That comes at the end.
It'll come naturally, it always has. So just be like water, let it flow and as it comes to you serve the customer and then be prepared to offer your product solution.

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Ryan Mathisen - co-founder and CEO of GloveBox

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Ryan Mathisen - co-founder and CEO of GloveBox

In this episode, I had a fun conversation with Ryan Mathisen, CEO, and co-founder of GloveBox. We talked about GloveBox, growing up in an insurance agency, MMA, guerilla marketing, and the upcoming GloveBox’s market place.

“Let’s show them the policies that they don’t have”

In our session, Ryan points to the conditions and the “systems” currently in use that make GloveBox’s value proposition so appealing. He adds depth to this with his experience growing an agency in Denver, CO.

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Emilio Figueroa - Chief Insurance Officer at Foresight

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Emilio Figueroa - Chief Insurance Officer at Foresight

In this episode, I had the pleasure of talking with Foresight's Chief Insurance Officer Emilio Figueroa. Our conversation quickly turned into a Q&A and of an Insurance 101 class.

“…we would maintain the MGU as a distribution platform and just purchase a shell company... then start writing business under that shell as long as we have the the necessary reserves and the correct reinsurance partners to help us.”

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Denise Garth - Chief Strategy Officer at Majesco

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Denise Garth - Chief Strategy Officer at Majesco

In this episode, I enjoyed talking with Denise Garth, the Chief Strategy Officer for Majesco. Denise is responsible for leading marketing, industry relations, and innovation to support Majesco’s client-centric strategy, working closely with Majesco customers, partners, and the industry.

In October 2020, Denise was recognized as Top 50 women in SaaS for 2020 for her contribution to the SaaS industry.

…this pandemic has been a tipping point for many industries to rethink their business models and rethink digital. Business and consumer behaviors have dramatically changed. I know mine have… We all need to rethink how we're going to move forward into a different era of insurance, specifically as an industry, given the dramatic changes and behavioral changes and expectations that customers have now.

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Kazy Hata - Founder and CEO of Just In Case

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Kazy Hata - Founder and CEO of Just In Case

In this episode, I had the honor to talk with Kazy Hata CEO and founder of Just-in-Case. Kazy-san has over 15 years of insurance-related service experience. In 2016, he founded Just in Case, the first Japanese InsurTech startup. Today, after four years of operation, Just in Case offers five distinct products and three unique business models.

normally an insurance company does not have an engineer/designer internally, but for an IT startup to have an engineer/designer internally it's a normal thing. it's just like to inhale air. So let's do something normal as an IT company but with the insurance knowledge in it, or you know, spirit in it.