Policy in Wonderland

Hosted by Evyatar Amira

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Sep 2026

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About the show

To everyone, Insurance is a pretty boring subject, just as Alice was bored before she saw the white rabbit running into the hole. In Policy in Wonderland, we will take you down the rabbit hole of insurance, and you will be amazed at how this world is interesting, full of curiosity, and with amazing people, tech, and even imagination. Don’t forget, follow the white rabbit.

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33 recent

September 24, 2026Episode 3450 min

Beyond the Insurance Lens | Manjit Rana

What happens when we stop looking at every challenge solely through an insurance lens? In this episode of Policy in Wonderland, Evy Amira speaks with Manjit Rana, Executive VP, Insurance at Clearspeed, about the future of insurance innovation - and why many of the industry’s best ideas may come from outside it. Manjit shares his perspective on moving beyond “innovation theatre,” designing more frictionless and fair customer journeys, and rethinking insurance products for a world of embedded protection, connected ecosystems and dynamic data. The conversation explores: • Why insurance is still widely misunderstood • What mature innovation functions should actually do • How technology can reduce friction without increasing bias • Embedded insurance and the rise of protection ecosystems • Why future leaders need to think beyond their functional expertise • What founders need to understand before expanding into new markets • The value of stepping outside your comfort zone - and outside the industry A thoughtful conversation about creativity, leadership and building an insurance industry that better reflects the way people live, work and buy today. Subscribe to Policy in Wonderland for more conversations with the people shaping the future of insurance

August 13, 2026Episode 3237 min

Beyond the AMS with Michael Lebor

What comes after the traditional AMS? In this episode of Policy in Wonderland, I speak with Michael Lebor, President of Momentum AMP, about the future of independent insurance agencies and InsuranceAgency.ai - the company’s AI platform designed to move beyond answering questions and help agencies complete actual work. The average independent agency uses around 14 different technology systems, many of which do not communicate effectively with one another. Michael explains why the answer is not simply another tool, but an open ecosystem connecting agency data, existing systems, InsurTech solutions, and AI-powered workflows. We discuss how InsuranceAgency.ai is intended to become part of the agency’s operation: connecting different systems, supporting workflows, and enabling AI agents to perform repetitive tasks across servicing, sales, renewals, finance, and other areas. Michael also shares how Momentum mapped 165 workflows across seven types of agency work, and explains the important difference between asking ChatGPT a question and truly integrating AI into the business. As AI begins handling certificates, policy comparisons, renewals, client communications, and other insurance tasks, trust, control, and human oversight become even more important. Where will people continue to create the most value? And what will the independent agency look like three years from now? Michael’s honest answer is that no one can know with certainty - even six months ahead. But one thing is clear: “Hope is not a strategy.” Chapters: 00:00 – The “SaaS Apocalypse” and Independent Agents 00:20 – The 14-System Problem Inside Insurance Agencies 03:40 – Moving Beyond the Traditional AMS 08:50 – Building an Open InsurTech Marketplace 11:55 – The Vision Behind InsuranceAgency.ai 15:30 – Using AI vs. Truly Integrating It 22:45 – Seven Worker Types and 165 Agency Workflows 28:30 – Trust, Control and AI Mistakes 33:05 – What Will the Independent Agency Look Like? 36:30 – “Hope Is Not a Strategy”

July 10, 2026Episode 3137 min

From Policy to Protection with Clinton Houck from FAIR

Will AI replace insurance agents, or are we asking the wrong question entirely?In this episode of Policy in Wonderland Media, host Evy Amira sits down with Clinton Houck, Head of Partnerships & Distribution at FAIR. Clint grew up in a multi-generational insurance family and has sat in nearly every seat in the industry—from underwriting and commercial lines to owning multiple digital and traditional agencies. Today, he leads distribution for a company redefining vehicle protection. Together, they go down the rabbit hole to dissect why traditional "reactive" insurance models are hitting a wall, how the rise of AI is actually going to train (rather than replace) the next generation of risk advisors, and the hidden unit economics behind why monoline auto insurance struggles with retention. Clint breaks down FAIR’s unique strategy: moving mechanical breakdown protection (warranty) out of traditional car dealerships and dropping it directly into the independent insurance channel as a powerful tool for agent stickiness and alternative revenue streams. In this episode, we explore:* The AI Roleplay Revolution: Why agentic AI and live simulation companies (like Symphony AI) are quietly reshaping how new agents generate expertise to replace retiring industry giants. * The Unit Economics of Distribution: Why digital monoline auto policies often churn every 6–8 months, and how multi-year warranty contracts lock in premiums and fundamentally alter agency retention. * The Specialty Shift: Moving from a traditional "policy salesman" to a holistic family and business risk manager. *InsurTech Founder Blindspots: The biggest mistakes founders from outside the ecosystem make when pitching products to legacy carriers and busy agencies. ⏱️ Timestamps:00:00 – Welcome to Policy in Wonderland: Meet Clint Houck01:24 – Clint's multi-generational journey through the insurance seats03:43 – The inflection point: Internet leads in 2012 vs. AI in 202606:17 – Captive vs. Independent agencies: Leveraging choice and depth08:38 – What is FARE? Redefining the auto warranty space10:32 – Auto Insurance vs. Auto Warranty: Bridging the coverage gap11:54 – The stickiness factor: Fixing the 6-month churn cycle14:20 – The psychology of the cross-sell: Why mechanical breakdown is an easy pivot16:46 – Rewriting the trust: Moving away from the car dealership model20:17 – Where AI actually creates immediate value behind the scenes22:46 – Symphony AI & the future of training the next generation of risk advisors26:27 – Inside the State Farm Ventures lens: Founder mistakes & InsurTech blindspots30:15 – Deciphering customer segments in insurance distribution32:53 – The 2030 Agent: The return of human-to-human connection and trusted advisors 🔗 Connect with Us:📌 Follow Evy Amira on LinkedIn: https://www.linkedin.com/in/evyatar-amira-adv/📌 Learn more about Wonders Bridge: https://wondersbridge.com/📌 Subscribe to the Policy in Wonderland Newsletter for more structural risk insights: https://www.linkedin.com/build-relation/newsletter-follow?entityUrn=7130201439502557188Don't forget to Like, Subscribe, and Share this episode if you found value in engineering the future of risk! 🐇🌪️#insurance #InsurTech #AI #InsuranceDistribution #Warranty #RiskManagement #PolicyInWonderland

May 21, 2026Episode 3058 min

Inside California’s Insurance Crisis with Insurance Commissioner Candidate Patrick Wolff

What happens when one of the most important insurance markets in the world comes under pressure? In this episode of Policy in Wonderland, Evy Amira — founder of Wonders Bridge , insurance advisor, and host of Policy in Wonderland — sits down with Patrick Wolff , financial analyst, insurance professional, two-time U.S. chess champion, and candidate for California Insurance Commissioner, for a deep conversation about the state of California’s insurance market and where it may be heading next. Together, they discuss: ♟️ What fundamentally broke in California’s insurance market ♟️ Wildfires, catastrophe exposure, and systemic risk ♟️ The rapid growth of the FAIR Plan ♟️ Why California may be lagging in insurance innovation ♟️ AI, underwriting technology, and prevention models ♟️ The role of regulation in catastrophe-exposed markets ♟️ How incentives can be aligned to reduce losses and improve resilience They also explore broader questions around insurance regulation, market structure, transparency, and the future relationship between technology and traditional insurance carriers. And finally, Evy asks Patrick one unexpected question: Which insurance industry figure would he invite to a chess match — and why WB was his answer 👀 California’s Insurance Commissioner election will take place on June 2, 2026, making this one of the most important regulatory conversations in the insurance industry today. Important disclaimer: This episode is intended solely for educational and professional discussion purposes. It does not constitute political endorsement or support for any candidate or political position. The purpose of this conversation is to provide meaningful insight, professional analysis, and thoughtful discussion around insurance markets operating under pressure. #Insurance #Insurtech #CaliforniaInsurance

September 13, 2025Episode 2915 min

From ITC Vegas to the 19th Hole - Policy in Wonderland with Stephen Goldstein

Sometimes the most valuable moments at a global conference don’t happen on stage - they happen at the 19th hole . In this episode of A Wonderland of Possibilities , I talked with Stephen Goldstein (Founder & Managing Principal at TETRA G, ITC Life, Health & Benefits Advisory Board member) about: 🔹 The power of authenticity in leadership🔹 How golf can teach you to listen, adapt, and play the long game🔹 Why real connections often start outside the meeting rooms

September 8, 2025Episode 2844 min

The Power of Parametric: Adaptive’s Mission to Reinvent Protection

When two industry leaders Michael Gulla (CEO, ex-Hippo) and Arik Arik Yelovitch (CTO, ex-Hippo) - decided to build Adaptive Insurance, they set out to solve one of the biggest blind spots in commercial insurance: business interruption.As Michael shared: “Most small businesses don't go out of business because of a major climate catastrophe. They're die-by-a-thousand cuts… when they have an insurance event that then takes 3 to 4 months before their carrier can fully adjudicate that claim.”Adaptive’s answer: #parametric #insurance powered by AI and real-time climate data. With simple if-then triggers - “If the power goes down for 12 hours, then I get $10,000” - SMBs get immediate liquidity, backed by Tokio Marine HCC, to keep their businesses running.📖 Read more in our co-article on The Underwriter: From Catastrophes to Coverage - https://www.linkedin.com/pulse/from-catastrophes-coverage-evyatar-amira-jynnf 🎧 Watch the full conversation now on Policy in Wonderland Podcast.

February 14, 2025Episode 2727 min

The Mr. Beast of Insurance: Gordon Coyle - 27

Meet Gordon Coyle, dubbed "The Mr. Beast of Insurance" - a third-generation insurance broker who's transformed his family's 95-year-old business through YouTube. With over 600 videos and generating 3-4 qualified leads daily, Gordon shares how he's revolutionizing insurance marketing through digital content. From his key takeaways at ITC 2024 to practical tips on building trust through video, discover how traditional insurance expertise meets modern digital innovation. Gordon's Youtube channel - https://www.youtube.com/@TheCoyleGroupNY

February 7, 2025Episode 2634 min

Time to Market Meets Quality: with Rob Seconitne - 26

Join us with Rob Secontine, VP of Sales at EmTech Group, as we dive into the future of insurance quality assurance and automation. In this episode, discover: How insurance carriers are revolutionizing their QA processes Why "Day Two" issues matter in insurance software The power of reducing testing time from 2,500 hours to just 30 Fresh insights from ITC 2024 The democratization of quality assurance Whether you're a carrier, InsurTech startup, or insurance professional, learn how quality testing is reshaping insurance technology development. Don't forget to subscribe to our newsletter for more in-depth insurance innovation insights!

January 10, 2025Episode 2550 min

How We Created an Age of Fire with Stephen Pyne - 25

In this timely episode of Policy in Wonderland, we're joined by Stephen J. Pyne, America's preeminent fire historian and author of "The Pyrocene." From his 15 seasons fighting fires at the Grand Canyon to becoming a leading voice on fire's role in shaping our world, Pyne offers crucial insights into humanity's complex relationship with fire. As wildfires impact communities worldwide, Pyne explains: Why fire is a "shapeshifter" and how it defines our era The difference between "good" and "bad" fires How urban fire differs from wildland fire Why developed countries face increasing fire challenges What we can learn from fire's history to secure our future Whether you're in insurance, emergency services, or simply concerned about our changing world, this episode offers essential insights into one of humanity's oldest relationships. Our thoughts are with those affected by wildfires - stay safe and informed.

December 31, 2024Episode 2437 min

#Ep 24 | Beyond The Shiny (AI) Tools with Vidur Nayyar

Fresh from ITC Vegas 2024, join us for an insightful conversation with Vidur Nayyar, founder of Upchange.ai and former McKinsey consultant, as he shares his unique perspective on insurance transformation. In this episode, we explore: Plus, Vidur shares invaluable advice for InsurTech startups and his vision for the future of insurance innovation. Whether you're an insurance professional, tech innovator, or curious about the transformation of this vital industry, this episode offers practical insights and strategic perspectives you won't want to miss. Connect with Vidur: LinkedIn: https://www.linkedin.com/in/vidur-nayyar/ Upchange.ai: https://www.upchange.ai/ #PolicyInWonderland #InsurTech #InsuranceInnovation #ITC2024