InsurTech Talks

Why One API Wasn't Enough: Duncan Crystal on Strategic Placement at Scale

He Got Into Insurance for Revenge. Then He Built the Library the Industry Never Had.

Nine Months After the SaaSpocalypse: What Michael Nadel Actually Learned

The Elbow Chart: How Rick Zullo Actually Decides What Makes an Insurance Startup Investable

What Happens Behind the Badge: Inside ITC Vegas 2026

Capital, Underwriting, Distribution, Trust: A VC's Framework for Where Insurance Value Actually Lives

Stop Trying to Detect Fakes. Prove What's Real Instead.

The Data Problem Nobody Has Fully Solved: Inside Delegated Authority with Paul Templar

The Problem Is Not the Technology. It Is the People Using It.

The Man Who Built InsurTech Before It Had a Name

We Talk Too Much About Technology and Not Enough About People

The AI Race Moved to the Construction Site. Shepherd Is Building the Insurance for It.

The Filing Cabinet Nobody Fixed — And the AI Liability Gap Nobody Is Talking About

You Can't Play the M&A Game If You're Not Growing Organically First

The Safety Net Your Claims Team Doesn't Know It Needs

Parametric insurance isn't just a claims shortcut. It's a bridge to new capital, a hedge against climate volatility, and — when hybridized with traditional coverage — a smarter way to get customers…

You Think Your Sales Process Has 22 Steps. It Actually Has 57. FrontRace Is Here to Show You the Difference.

The $100 Billion Niche Nobody Talks About: A Surety Bond Primer with SwiftBonds Founder Gary Eastman

From Wearables to $100M: How Kinetic Comp Learned to Listen to Its Customers

The Compliance Layer Nobody Built — How ProducerFlow Turned an Internal Tool Into a Business

The Health Insurance Broker Has Been Underinvested For Too Long — Gyde Is Here to Fix That

The 80% of Insurance Documents Nobody Is Reading — And What Upstage Is Doing About It

Wildfire Conflagration Is Its Own Peril — And Insurance Has Been Getting It Wrong

The Insurance Industry Has a Clerk Problem — And Technology Is the Only Way Out

Under Fire and Still Showing Up: Kobi Bendelak on Israeli InsurTech Resilience

How to Navigate the Evolving Insurance Industry: Insights from Experts

Transforming Insurance: How a Startup is Redefining the Industry

Better Building Materials Are an Underwriting Strategy, Not Just a Climate One

Nobody Wants to Plug a Billion Dollars of Premium Into an Unproven Startup

A 95% Accurate AI Model, Chained Twenty Steps Deep, Gets the Job Right 30% of the Time

Direct-to-Consumer Life Insurance Failed Because Nobody Wants to Buy Insurance Alone

The Real Competitor to Every Core System Vendor Is Excel

The Cheapest Way to Grow Your Book Is to Stop Losing the Customers You Already Have

I sat down with Lior Keren of Pumpkin to explore the intersection of pet care and insurance.

Six Weeks Out From a Show With 700 Exhibitors and Fourteen Concurrent Stages

The User Experience Is the Tip of the Iceberg. The Product Is the Claim.

Why Does Shipping a Truck 100 Miles Cost the Same to Insure as 1,500?

Policy Administration Is a Data Model Problem That the Industry Has Been Treating as a Workflow Problem

The Industry Kills Innovation, So Stop Selling It Tools and Just Do the Work

The Product Nobody Had Built: Fertility Insurance You Own Yourself

Mahesh Vinayagam named his company on a flight from Phoenix to New York, roughly eight years ago, with a Bloody Mary in hand and a napkin in front of him.

They Agreed Mileage Was the Most Important Data. Then They All Said No.

Not a Seed Fund: Concentrated Bets, Curated Rooms, and Niche Lines Nobody Wants

Your Employer Picked Your Carrier. If That Carrier Doesn't Cover Your Doctor, You Never Had a Choice.

The Reason LegalTech Said No: Your Product Reduces Their Billable Hours

Data Is the New Oil. When's the Last Time You Got Paid for Yours?

Forget the List of Vendors. Just Describe What You Need.

Insurance Is Not a Plastic Cup. It's a Relationship That Lasts a Year, With Moving Parts.

Data Isn't Wrong. It's Just Never Synchronized.

Innovation Isn't Disruption. It's SpaceX Wanting NASA's Money, and NASA Wanting SpaceX.

Insurance Companies Aren't Spying on You. They're Trying to Send You a Warm Blanket.

68% of P&C Carriers Run Three or More Policy Systems. Almost None Get an Apples-to-Apples View.

Insurance Is a Laggard Industry. You Can Get an Amazon Package Faster Than a Quote.

Imagine If Auto Insurers Wouldn't Cover Collision Unless You Bought It Within 30 Days of the Car

Points, Badges, and Leaderboards Are Just the Tip of the Iceberg

Cargo Delay Has Been Excluded From Marine Insurance for 400 Years. Nobody Ever Fixed the Exclusion.

Enablement, Not Disruption: You Don't Change Insurance, You Upgrade the People Who Run It

Japan's Insurance Market Is Bigger Than China's. It's Also Nearly Impossible to Enter From Singapore.

The CVC Head Who Negotiated: I Can Only Say No, and Every "No" Goes in a Spreadsheet

Carriers Paid Under $50 for an Underwriting Inspection for Decades. That Math Stopped Working.

Insurance Benefits More From Traditional AI Than From GenAI. Almost Nobody Understands the Difference.

Insurance Doesn't Actually Have a Failure Culture. Make a Big Mistake as an Underwriter and Nobody Says "Thank You for Learning."

US Vets Don't Want Anything to Do With Pet Insurance. They're Afraid of Becoming Human Health Insurance.

Less Than 10% of the 80 Million Americans Turning 65 Have Any Way to Pay to Grow Old

A Restaurant That Adds Happy Hour Three Nights a Week Is a Different Risk Than the One You Underwrote

A Forest Fire Can Retroactively Invalidate a Carbon Credit You Already Paid For

150 Midwest Carriers Went Into This Year Without Reinsurance

Everyone Says Smart Money vs. Dumb Money. Kate Johnson Calls It Hogwash.

Extract the Declination Reason From the Email. Never Ask an Underwriter the Same Question Twice.

The Missing Layer Wasn't Exotic. It Was Finance 101: Have Someone Check the Collateral Actually Exists.

Don't Build the Comparative Rater. Bring the Right Product Straight to the Agent's Desk.

$4 Billion in Reinsurance Premium, Zero to That in Five Years. That Growth Rate Should Have Been the Red Flag Itself.

Insurance Quoting Can Take 30 Seconds. On the Internet, That's the Same as a Website That Doesn't Work.

VC Wants Growth at All Costs. Insurance Wants Safe and Steady. Those Two Instincts Are Structurally Opposed.

40% of an Underwriter's Time Goes to Opening Emails and Hand-Keying Data

When You Leave an Employer, Nobody Sends You a TriNet Email Anymore

Don't Raise Just Enough to Get By. Raise What You Need, Plus Some, and Stop Playing the Market.

Not All Insurtech Is IndieTech. But All IndieTech Is Insurtech.

45 Minutes, Five Systems, One Quote. Better Agency's Whole Thesis Is Collapsing That Into Five Minutes, One Screen.

We Put the Whole First Symposium Together in Six Weeks. No Sponsors, No Tickets Sold, Off We Went.

Nobody Had Ever Legally Defined "Cold Storage" Before. It Was Sitting Undefined in Policy Language.

6,000 Quotes to 35,000 Quotes Year Over Year, Without Hiring 100 New Underwriters

Do You Want to Be an Insurance Company, or a Tech Company That Sells to Insurance?

The Ship Sank. Lloyd's Paid the Claim. Then, By the Principle of Subrogation, the Gold Belonged to the Insurer.

Half of America Doesn't Know This Product Exists. The Other Half Thinks It's Only for Accidents.

It Started at a Panera Table Outside DC. Six Months Later, 1,500 People Showed Up in Vegas.

Every Company Has a Digital Profile. Insurance Just Hasn't Been Using It.

Kobi Bendelak and Gilad Shai talk about a new initiative to host insurance executives and investors delegations to the vibrant center of InsurTech innovation in Tel Aviv and Jerusalem, Israel.

One Client Pays Less for Health Insurance Today Than They Did in 2009

80% of the People Who Bought His First Policy Were Otherwise Completely Uninsurable

The Costco Model: Sell Everyone Else's Products Well, Then Slowly Build Your Own Kirkland Brand

Two-Thirds of the Optimal Transactions Happen When the Market Doesn't Trust the Information. Insurance Runs on That Missing Third.

12 Insurers Went Insolvent After Hurricane Andrew. After a Storm Ten Times Larger, One Did.

Munich Has More Insurtechs Tied to It Than Silicon Valley Does

How Do You Quantify That Someone Can No Longer Water-Ski With Their Family?

The Small Business Owner Is a Very Unloved Insurance Customer. Beam Wants to Give Them Big-Company Benefits Anyway.

Insurance Is a Product Built on Differentiation. So Why Is Insurance Marketing Standardized?

We're Not an Agency. We're the Product Manufacturer.

No One Has Ever Told an Insurance Carrier They're Too Cheap

A Boater Built an MGA for Boaters. Insurance Was Invented in the Maritime Space Anyway.

THC Stays in Your System Long After You're Sober. A DUI Charge Doesn't Care.

Your Wealth and Your Health Are the Same Balance Sheet. Retirement Planning Rarely Treats Them That Way.

A Borrowed Volvo Saved His Father's Life. Not Everyone Gets Access to That Volvo.

The Holy Grail Isn't a Better App. It's the Independent Agency Channel.

The Data Gets Built Once for a Renewal, Then Thrown in the Bin

Carriers Are Great at Managing Expenses. They're Just Not Good at Deploying Technology.

Agents Have Been Making Bad Technology Look Good for a Long Time

The Building Isn't $50 Million. It's $500,000. The Data Just Came In Wrong.

The Last Integration You'll Ever Need to Make

100 Out of 100 People Said They'd Never Buy Travel Insurance. That Was the Opportunity.

30 Open Browser Tabs Is the Real Adjuster Problem

1.2 Billion Vehicles, Not Policies Written: Sizing the Real Market

Health Insurance Is Insurtech's Biggest Boogeyman

In 1985 You Could Get an Oracle Trial License. In 2014, No Policy Admin System Offered the Same.

ITC 2021's Real Theme Wasn't Technology. It Was Capacity.

A 1998 Truck and a 2020 Truck Get the Same Quote From Every Incumbent

Three Engineers With No Insurance Background Built a Dental Insurer From Scratch

Lemonade Didn't Buy Metromile's Data. It Bought Its Claims Team.

Insurance Technology Will Never Have as Many Investors as Biotech. That's the Business.

Why Isn't Anyone Asking Startups What Loss Ratio They Targeted, and What They Actually Hit?

The Lowest-Ranked Value Proposition Was the Entire Company

The Top Competitor to Low-Code Isn't Another Vendor — It's Custom Code

Liri Halperin Segal opened Episode 51 fresh off a talk at the UN, describing Parliament 51 — a social impact venture she co-founded with Danielle Ofek aimed at closing the gender gap in corporate…

Sabine VanderLinden has spent 25 years in and around insurance, and this episode traced most of that path: from Lloyd's of London, where she arrived via an Erasmus exchange program from continental…

From Boots-on-the-Ground Inspections to 459 Milliseconds

Caribou Honig opened Episode 48 talking about crabbing on the Chesapeake Bay — a piece of chicken tied to a string, attached to a $3 PVC pipe from Home Depot, stuck in the sand while you wait with a…

A Rewards Program That Doesn't Trip the Rebate Laws

The Question Every Underwriter Actually Needs Answered: What Does This Business Do?

He Taught a Computer to Read Textbooks Before He Taught It to Read Insurance Policies

Building Plaid for Car and Home Insurance

"Are You the Right Contact?" Is the Question Every Startup Should Ask

Ken Tashiro brings a background genuinely uncommon in insurance: raised in Tokyo by a Japanese and German family, educated at a German school through high school before university in Japan and…

Turning Insurance's Most Common Claim Into a Retention Tool

The Insurance Elephant, and Why Nobody Sees the Whole Beast

The Insurtech He Won't Name — and the Trust That Comes From Showing Up Every Six Weeks

What Eight Insurance Startups Learned the Hard Way

Flood Insurance, Sold the Way You Buy a Shirt

Gil Arazi began the conversation with a confession: before he played guitar and piano, he was a violinist with perfect pitch, something almost no one knows. Gilad, a lefty who never got past three…

Which Door Into Insurance? A Lawyer's Map of the 50-State System

The episode began with fitness. Bobbie and Gilad share a fitness-minded Twitter community, and she described the lockdown project that came out of it: a CrossFit-style gym in her basement, built up…

Susan Hatten dialed in from the Des Moines area, from the Holmes Murphy headquarters in Waukee, Iowa, where the office was at about 25 percent occupancy and a sense of normalcy was starting to…

When the Interviewer Becomes the Interviewee

A Lawyer and an Engineer Walk Into a Bar and Start an Insurance Company

Making the Smallest Accounts the Most Profitable

A 100-Year Company, Starting With a Reserved Ticker

From Honeymoon Hurricane to Head of Reinsurance

Samantha Chow owns the life, annuity and health markets at EIS Group, making sure the R&D, sales and marketing teams understand how the company's technology supports those industries. She brings more…

The Manufacturer of Small Commercial Insurance

Gilad opened with Buenos Aires: Christmas in summer, asados, and alfajores. Hugues Bertin has lived in Argentina for 15 years and has three sons there, though, he admitted, he doesn't like mate.

Life Insurance Is a Service, Not a Product Line

Auto Insurance That Looks Like a Prepaid Phone Card

From Cambodia to Cucumbers to Reinsurtech

Innovation as Risk Transfer for Business Models

Corporate Venture Capital, in a Patagonia Vest

The War for Talent Is Over, and Talent Won

Insuring the Movie, the Script and the Robotic Camera Arm

Ed Gaze joined Lloyd's in August 2018 after ten years as a consultant at KPMG and EY specializing in technology and data. The episode opened with Ed remembering Gilad turning up at Lloyd's in jeans…

Predicting What People Will Do, Without Knowing Much About Them

Avi Bartov is CEO and co-founder of GamaSec, which provides pre-breach services helping commercial lines brokers and carriers manage cyber risk and educate their policyholders. He served as an…

Ben Munro is CEO and co-founder of Briza, a Toronto-based company that connects agents with insurers for instant online delivery of commercial insurance. He has spent his career in insurance:…

This holiday special ran longer than planned, as Gilad admitted, and began with a tangent about lighting, chocolate babka from a bakery Jay always brings when Gilad visits New York, and who has more…

Making Health Benefits Understandable at the Front Desk

From Horseback to Horsepower to Whatever Comes Next

Life Insurance Is at Risk of Becoming a Luxury Good

The Customer Is at the Center: A Slogan That Has to Become Reality

Ryan Mathisen is co-founder and CEO of GloveBox, based in Denver. He grew up in insurance: his father started an independent agency about 35 years earlier, and Ryan remembers licking stamps and…

Insurance 101: MGA, MGU, Captives and Shells

Denise Garth is Chief Strategy Officer at Majesco, responsible for marketing, industry relations and innovation in support of the company's client-centric strategy. She is a recognized Top 50…

Five Products in Four Years, in One of the World's Most Conservative Markets

An Agent Builds the Back Office He Wished He Had

Building an Insurtech Community in Hartford

Sidd Gavirneni is CEO and co-founder of Zeguro, a San Francisco company combining cyber security and cyber insurance for small and mid-sized businesses. Its Cyber Safety solution unites risk…

Insurance Is a Tax on Doing Business. Intuit Wants to Change That