InsurTech Talks

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

In this episode, Bryan Falchuk and Gilad Shai talk about Bryan’s new book “The Future of Insurance vol. 2.” It will be easier to send you directly to Amazon and purchase Bryan’s book because that’s…

Jim Albert, chairman and co-founder of Neptune Flood Insurance, and Gilad Shai talk about Neptune, podcasting, using API, the power of AI as a multiplier in the insurance industry, insurance programs…

In this week's episode, Gil Arazi, founder and managing partner of FinTLV Ventures, joins Gilad Shai to discuss FinTLV's fund meteoric growth, the fund's investment thesis, and playing the piano,…

In this week's episode of insurTechTalk by InsurTechLA, Michael Byrne shares his knowledge and insights on the legal structure and strategy when launching a new InsurTech venture, in which territory…

In this episode, Bobbie Shrivastav, co-founder and CPO of Benekiva, talks with Gilad Shai about the challenge of life insurance companies to manage claims, Nigel Walsh's fitness program, female…

In this episode, Susan Hatten, COO of BrokerTech and a senior manager at Holmes Murphy, and Gilad Shai talk about BrokerTech Venture' 5 towers (Accelerator, Early Stage Investments, Innovation,…

Thomas Verduzco-Weisel, Director Central Europe for CoreLogic | Symbility and an active InsurTech evangelist and Gilad Shai come together on Thomas's Clubhouse "Insurance Innovation"…

In this episode, James Bowen, CEO and Co-Founder of Energetic Insurance, joins Gilad Shai to talk about Credit Insurance in the renewal energy industry, the gap in underwriting loans, having great…

In this episode, Phillip Naples, CEO and co-founder of Layr, a digital insurance brokerage pumped up with AI and magic, talks with Gilad Shai about Layr (of London), placing the rails for insurance,…

In this episode, Jeff McCann, CEO and Founder of APOLLO, and Gilad Shai talk about APOLLO, an online insurance company based out of Vancouver, Canada, merch, Jeff's vision, investors, and Good to…

In this episode, Isaac Espinoza, Head of Reinsurance at Root insurance, a Columbus, Ohio, based car insurance company that recently, October 28th, 2020, went public on the Nasdaq, and Gilad Shai talk…

InsurTechTalk by @InsurTechLA Episode 27 In this episode, Samantha Chow, the Life, Annuity, and Health Markets Lead at EIS Group, and Gilad Shai talk about CoreTech, the frictionless experience that…

In this episode, David McFarland and I talk about Coterie, empowering the Small Medium Business (SMB) insurance with APIs and a digital binding authority. David elaborates on working with other…

In this episode, I am pleased to host Robert Smithson, CEO & Founder of JUST Insurance (Insurer). It is a vibrant and very educational conversation. Robert and I talk about JUST, fair insurance,…

..in early 2017, everybody was still trying to find their way. The term \[InsurTech\] didn't really have a solid definition, but more than anything, our clients were quite paranoid about being…

In this episode, Dan White, managing partner at NINETY, and I talked about Dan’s “insurance bets” for 2021. Dan talked about Micro Insurance; lessons learned from micro-insurance that carriers can…

In this episode, Brian Anderson and Gilad Shai talk about investments in InsurTech startups. We warmed up the conversation with Patagonia (VC) vest and then moved to hotter topics as SPAC, the shift…

In our conversation, Jay D’Aprile and I talked about the "War for Talent," the challenges that the legacy companies face, the influence of the COVID pandemic on the workforce's future, and the…

This episode is different. Instead of talking about InsurTech, this week's guest, Daniel R'bibo, an Area SVP at Arthur J. Gallagher, enriches our knowledge about a topic that is close to InsuTechLA's…

In this episode, I had the pleasure of hosting Ed Gaze. Ed joined Lloyd’s in August 2018 following ten years as a consultant at KPMG and EY, specializing in technology and data.

In this episode, I had the pleasure of hosting Avi Tuschman. Avi is the Chief Innovation Officer and founder of Pinpoint Predictive. He is a Stanford StartX entrepreneur and an internationally…

In this episode, I had a very interesting conversation about Cybersecurity with Avi Bartov, the CEO and co-founder of GamaSec. GamaSec provides pre-breach services helping commercial lines insurance…

In this episode, I had the pleasure of hosting Ben Munro. Ben and I talked about delivering commercial insurance via API, about his company--Briza, building a company that service insurance agents…

For this Holidays Special, Jay Weintraub and I had a jolly conversation, that I admit, was longer than planned, but it was entertaining.

In this episode, I enjoyed talking with Jeremy Bluvol and CEO and co-founder of ANAGRAM.

Well over a century ago our mobility solutions shifted from horseback to horsepower, and ever since then AAA has helped pave the way for the advancement of new technologies that significantly…

Jake is CEO of Everyday Life Insurance, a Boston-based tech startup that is making life insurance smarter and more inclusive for everyday people. Inspired by the opportunity to use breakthrough…

Troy Korsgaden is a highly sought-after insurance and financial services consultant. He is the principal of Korsgaden International, which specializes in global marketing, distribution, agency…

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…

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.

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…

Japan is known for being a complex of contradictions and amazements to the outside visitor. On one hand, it is a conservative, hierarchical culture and it is slow to react. On the other hand, it is…

Cover Desk Founder and CEO Andy Priesman is an insurance industry veteran with significant and extensive operational experience. He knows what it takes to make an independent insurance agency run…

For this episode, I had the pleasure to chat with Paul Tyler. Paul Tyler serves as Chief Marketing Officer for Nassau where he leads the marketing strategy, direct-to-consumer channel, and innovation…

In this episode, I had the pleasure to host Sidd Gavirneni. Sidd is the CEO and co-founder of Zeguro, a cybersecurity, and a cyber insurance company focused on small and mid-size businesses. Based in…

This is my first pre-recorded, no audience, unscripted podcast. I am very happy that my first guest was Mauricio because it requires energy and a very interesting story to tell so we can keep the…