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

Brokerage

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Cheri Martinen, Managing Partner, OneDigital

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Cheri Martinen, Managing Partner, OneDigital

Cheri Martinen bought her family's fourth-generation insurance agency with no intention of selling. She built it into a niche powerhouse — writing more wildland firefighter contractor policies than anyone on the West Coast — before OneDigital made her an offer that was actually about the people, not just the book. In Episode 161, she shares how she ran an agency that was always ready for diligence, why the AMS filing cabinet problem remains unsolved, and what she learned at a recent CIC class that should alarm every agent and business owner: AI-generated content may already be excluded from your GL policy — and most people have no idea.

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Curtis Barton, CEO of ALKEME

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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.

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Jack Siney, co-founder and CRO of FrontRace

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Jack Siney, co-founder and CRO of FrontRace

Jack Siney built FrontRace out of a real operational crisis: when COVID sent his sales team home, all the organic knowledge transfer that happened in an office disappeared overnight. The internal tool he built to fix that problem became a nine-figure exit. In Episode 157, he explains why your sales process probably has twice as many steps as you think, why AI on the business side is not ready yet, and what insurance agencies should be doing right now to prepare for the tools that will actually matter in 2027.

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Gary Eastman, founder of SwiftBonds

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Gary Eastman, founder of SwiftBonds

Most insurance professionals have heard of surety bonds. Almost none of them can explain what one actually is. In Episode 156, SwiftBonds founder Gary Eastman — attorney, 18-year surety specialist, and self-described young person by industry standards — breaks down how surety works, why it underpins trillions of dollars of economic activity that barely anyone in InsurTech is paying attention to, and why a niche still running on 1980s underwriting models is finally ready for a technology moment.

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Luis Pino, CEO Agentero

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Luis Pino, CEO Agentero

Luis Pino built ProducerFlow by accident — it started as an internal compliance tool for Agentero, the carrier-agency network he founded after leaving CoverWallet, and became a standalone product when carrier partners kept asking if they could buy it. In Episode 154, Luis explains what producer compliance actually involves, why carriers approach AI with a fundamentally different risk appetite than agencies, and why the question of the insurance agent's survival in an AI-native world is one of the most genuinely open questions in distribution right now.