Season 3 · 84 Episodes
Underwrite · The Insurance Conversation

The most importantindustry in the worldhas the quieteststories.

Long-form conversations with underwriters, actuaries, and agency owners — the minds that move markets, rarely given a microphone.

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Est. 2022 · Chicago, IL
Proof of depth

Three conversations.
Judge for yourself.

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Hard MarketEP. 081 · 1h 14m
Margaret Hollis, Senior Underwriter, Zurich NA
Margaret Hollis
Senior Underwriter, Zurich NA

What a Hard Market Actually Feels Like From the Underwriting Desk

"When capacity contracts, you see who actually understood the risk they were writing. Most people were just following the market up."

34%
Agency SuccessionEP. 076 · 58m
Robert Castillo, Principal, Castillo & Vance Insurance
Robert Castillo
Principal, Castillo & Vance Insurance

Agency Succession Is a Slow-Motion Crisis Nobody Wants to Talk About

"The average agency owner is 61. Their best producer is 58. And neither of them has had the conversation about what happens next."

Claims PhilosophyEP. 069 · 1h 08m
Dr. Yuki Tanaka, VP Claims Strategy, Tokio Marine HCC
Dr. Yuki Tanaka
VP Claims Strategy, Tokio Marine HCC

The Philosophy Behind Claims: Why Every Denial Is a Brand Decision

"Every claim file is a moment of truth. The policy was a promise — claims is where you find out if the company meant it."

The salon

Faces behind
the conversations.

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James Whitfield, Host & Executive Producer at Underwrite, portrait
84 episodes

James Whitfield

Host & Executive Producer · Underwrite

The industry has a vocabulary problem. When actuaries speak to agents, they're speaking different dialects of the same language.

Priya Nambiar, Co-Host at Underwrite, portrait
61 episodes

Priya Nambiar

Co-Host · Underwrite

InsurTech founders think they're disrupting a broken industry. Most of them haven't read a reinsurance treaty.

"Most financial media covers insurance from the outside. We cover it from the inside — where the actual decisions are made."
— Underwrite, Season 1 launch statement
Thomas Okafor, Chief Actuary at Berkshire Specialty, portrait
8 episodes

Thomas Okafor

Chief Actuary · Berkshire Specialty

Risk is not a number. Risk is a story about the future that we're pricing today with imperfect information.

Claire Oduya, Independent Agency Owner at Oduya & Partners, Dallas, portrait
5 episodes

Claire Oduya

Independent Agency Owner · Oduya & Partners, Dallas

Succession isn't a transaction. It's a decade-long conversation you should've started when you were too busy growing to think about it.

Marcus Delacroix, VP Underwriting at Chubb Commercial, portrait
6 episodes

Marcus Delacroix

VP Underwriting · Chubb Commercial

A hard market is the industry's correction mechanism. It's uncomfortable because it means someone was wrong about risk for five years.

"84 episodes. Every single guest has said something in the first twenty minutes that they've never said publicly before."
— James Whitfield, Season 3 opener
Soo-Jin Park, InsurTech Founder & CEO at Risklayer AI, portrait
4 episodes

Soo-Jin Park

InsurTech Founder & CEO · Risklayer AI

We built technology for an industry we didn't understand. The podcast helped us understand what problem we were actually solving.

The archive

Not a feed.
A curriculum.

84 episodes organized by the questions that matter most to people who work in insurance.

01
8 Episodes · EP. 081

Hard Market Survival

When capacity contracts and pricing corrects, how do underwriters, agents, and carriers navigate the pressure? Eight conversations from the front lines of the hardest market in a generation.

UnderwritingPricingCapacityReinsurance
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02
6 Episodes · EP. 076

Agency Succession

The average agency principal is 61. What happens to the book, the relationships, and the culture when they're ready to step back? Honest conversations about transition, valuation, and legacy.

M&AValuationCulturePerpetuation
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03
7 Episodes · EP. 069

Claims Philosophy

Every claim is a test of whether the policy was a real promise or just paper. Claims executives rarely get to speak candidly. Here, they do.

ClaimsCoverageLitigationCulture
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11 eps

InsurTech Reality Check

TechnologyAI
9 eps

How Actuaries Think

ActuarialModeling
10 eps

Carrier Strategy

StrategyLeadership
The Brief

One page.
Every episode.

Every episode distilled into a one-page executive summary — the argument, the insight, the three things worth knowing. Delivered Tuesday morning.

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