Context Window: AI, Insurance & The Humans Behind It

Kyle Nakatsuji, Dearborn Labs
  • 5.0 (3)
  • Entrepreneurship
  • Updated Daily

Welcome to Context Window: AI, Insurance & The Humans Behind It, the podcast for leaders, operators, and founders navigating the intersection of artificial intelligence and enterprise operations. Hosted by Kyle Nakatsuji, we discuss how real companies are deploying AI inside legacy industries like insurance, not as a hypothetical tech play, but as a practical blueprint powered by humans. Each episode features raw conversations with the builders and executives who are actually on the front lines managing data, scaling teams, and defining the future of business infrastructure.

Episodes

  1. Sep 15

    Will AI Take Your Job? Only If You Don't Use It | Rick McCathron, President and CEO of Hippo

    Rick McCathron, President and CEO of Hippo, gives the honest answer to the question every one of his employees is quietly asking about AI, and explains why thirty three years in insurance has taught him this panic has happened before. A Bakersfield kid who played left tackle at Oregon State until two ruptured discs ended it, Rick traces the path from underwriter trainee at Mercury, to running a Texas acquisition at twenty six after saying yes on the spot, to founding First Connect, to a meeting with Assaf Wand that was supposed to be business development and turned into the rest of his career. Discover why he says expense ratios have barely moved in forty years despite orders of magnitude better technology, why Hippo's hackathons now involve sitting beside the person doing the work, and what a South Carolina board member meant when he said no matter how many times you weigh a pig, it doesn't get any fatter. 00:00 - Cold Open 00:26 - Welcome and what Hippo actually does now 03:55 - Bakersfield, a left tackle at Oregon State, and two ruptured discs 05:05 - An assistant sheriff father and an independent agent family 09:39 - If you have personality be a reinsurance broker, if not be an actuary 11:25 - Why EQ beats IQ and why he hates Zoom 16:32 - The Dallas conference room and twenty panicked new employees 19:03 - The ninety tens and when the downside outweighs the upside 20:26 - A poker game, a promotion he did not want, and Texas at twenty six 25:20 - The three things, and doing twenty visits when the goal was fifteen 32:00 - Washing the car twice by two o'clock on Monday 35:14 - Starting First Connect with lunch instead of a salary 37:33 - A Texas storm, a reinsurance problem, and a meeting with Assaf Wand 40:11 - Everyone said direct to consumer, he bet on independent agents 43:36 - No company's path to success is ever a straight line 45:49 - Is AI going to take my job 47:29 - Expense ratios have not moved in forty years 48:38 - Claude for every employee and seat rides with the people doing the work 49:25 - The verbs in a business 50:25 - Weighing a pig doesn't make it fatter 51:40 - Vision without execution is hallucination Richard McCathron is the President & CEO of Hippo and has been a member of the Board of Directors since February 2017. Before Hippo, Rick held senior executive positions at various insurance companies, including First Connect Insurance as President & CEO, Superior Access Insurance as President & CEO, and Mercury Insurance Group as Regional Vice President. Rick is both a Chartered Property & Casualty Underwriter and a Certified Insurance Counselor and sits on the board of directors of Spinnaker Insurance Company, First Connect Insurance, The National Alliance of Insurance Education and Research, and Players Health. He is an advisor to several insurtech companies and holds a BS in finance from Oregon State University. Mentioned in this episode: Hippo — https://www.hippo.com/ Connect with Rick McCathron on LinkedIn — https://www.linkedin.com/in/richard-l-mccathron-514a4a4/ Subscribe to Context Window for more insights from the operators deploying AI inside real insurance companies. See what Dearborn Labs is building: We don't just talk about AI in insurance, we build the technology that powers it. Explore our latest projects and partnerships at https://dearbornlabs.com/

  2. Aug 27

    Buy the Expertise Not the Code with Bryan Falchuk, President and CEO of PLRB

    Bryan Falchuk, President and CEO of PLRB, unpacks why hubris is the thing standing between the insurance industry and real change, and why cash is what lets carriers avoid ever feeling the cost of it. A kid who got serious about insurance because his Venezuelan father could not look at a Ferrari without calculating the premium, Bryan traces the path from a Liberty Mutual internship to McKinsey, to running US operations at Beazley, to Chief Claims Officer at Hiscox commuting weekly from Boston to Atlanta, and into an advisory practice that started three months before the world shut down. Discover why he thinks build versus buy is the wrong question entirely, why one carrier spent heavily on a digital claims experience and then switched it off, and why losing a hundred pounds taught him something that applies to every transformation project he has ever worked on. 00:00 - Cold Open 00:48 - Twenty six years and why insurance lets the world function 03:53 - A Venezuelan father, a Ferrari, and the seed that got planted 10:21 - Economics, Chinese, philosophy, and finishing in three years 15:24 - Growing up overweight and where the drive to fix things started 18:01 - The teacher who stopped to actually understand him 24:40 - Why investors say they look for founders who have been damaged 29:39 - McKinsey, and whether it would still change you today 43:23 - Three ways into a turnaround and the one that only flatters you 48:44 - Eleven months, a glass wall, and a $198 expense report 52:51 - Hiscox, the commute, and missing thirty percent of his son's life 57:36 - The insurtech idea he thought was the stupidest he had ever heard 01:09:03 - The cook, the chef, and two very different kinds of AI 01:14:28 - The carrier that shut off its own digital front door 01:20:25 - Why build versus buy is the wrong question 01:22:05 - Protecting your alpha when knowledge is the advantage 01:25:10 - Do a Day and why you never lose a hundred pounds today 01:35:18 - Hubris, we can't because, and how might we Bryan Falchuk is the President and CEO of PLRB, the Property and Liability Resource Bureau, an insurance industry trade organization serving member carriers on property and liability coverage questions. He is also the Founder and Managing Partner of Insurance Evolution Partners, and the author of the best selling book series The Future of Insurance along with Do a Day, the personal philosophy he built after losing more than a hundred pounds. He has given several TEDx talks. Before PLRB, Bryan spent more than two decades across the insurance value chain, including corporate strategy and personal lines at Liberty Mutual, the P&C practice at McKinsey, distribution and US operations at Beazley, Chief Claims Officer at Hiscox USA, and growth at insurtech Hi Marley. He holds an economics degree from Bowdoin and an MBA from Tuck at Dartmouth. Mentioned in this episode: Bryan's books, TEDx talks, and writing, including "Do a Day" — https://bryanfalchuk.com/ The must have and must not have exercise Bryan walks through — https://www.bryanfalchuk.com/TheMustExercise.pdf Subscribe to Context Window for more insights from the operators deploying AI inside real insurance companies. See what Dearborn Labs is building: We don't just talk about AI in insurance, we build the technology that powers it. Explore our latest projects and partnerships at dearbornlabs.com

  3. Aug 13

    Go First and Go Positive with Joe Schmidt, partner at Andreessen Horowitz

    Joe Schmidt, partner at Andreessen Horowitz, unpacks why insurance work is finally addressable by software and what actually gets him excited about a founder before he writes a check. A Notre Dame linebacker who arrived as a fifth string preferred walk on and left as team captain and MVP, Joe traces the path from three goals written down at five years old to Accel, to building a business unit from scratch inside Ethos, and back into the investing chair at a firm managing more than $90 billion. Discover why he calls insurance a bits business that never had anything worth adopting until now, why the most recognizable logo can be the wrong first customer, and why nobody has used AI to invent a roof shingle that survives a hailstorm. 00:00 - Cold Open 02:01 - Orange County, three older sisters, and a competitive Counter Strike habit 07:50 - The three goals a five year old wrote down, including Notre Dame 12:37 - Fifth string to a nationally televised start 17:50 - The hour with the head of admissions that decided everything 25:41 - "Joe, why are we gonna put you in the game?" 36:03 - Hitting reset, 200 meetings, and never asking for a job 44:56 - Leaving venture for Ethos to earn the operator's empathy 52:11 - Oil wells and pipelines, the two businesses being built in insurance AI 56:14 - Bits, atoms, and the roof shingle nobody is inventing yet 01:06:29 - Lighthouse customers or land grab 01:10:57 - Quick fire, go first and go positive Joe Schmidt is a partner at Andreessen Horowitz, where he invests in early stage software, fintech, and insurtech. The firm manages more than $90 billion in total assets. Before returning to venture he spent time as an operator at Ethos, joining the life insurance company at roughly fifteen people and helping build the agent business that carried it to a multibillion dollar valuation. He started his investing career at Accel. Joe played linebacker at Notre Dame, arriving as a preferred walk on and finishing as team captain and most valuable player. He writes regularly on go to market strategy for AI companies and lives in San Francisco with his wife, his son, and their dog named Chipotle. Subscribe to Context Window for more insights from the operators deploying AI inside real insurance companies. See what Dearborn Labs is building: We don't just talk about AI in insurance, we build the technology that powers it. Explore our latest projects and partnerships at dearbornlabs.com

  4. Jul 29

    Why AI Should Industrialize Expertise Instead of Replacing It | Travis Hedge, Co-Founder + CEO Vouch

    Travis Hedge, Co-Founder and CEO of Vouch Insurance, unpacks how he built an AI-enabled brokerage for the innovation economy and cuts through the generative AI hype. A former venture investor at SVB Capital who grew up in his family's insurance agency, Travis traces the path from a third-grade career report that read "I want to be an insurance agent" to serving more than 6,000 clients from incorporation through IPO. Discover why speed to service is 40% of what clients actually value, why half of them still want to talk to a human even on a small policy, and his conviction that AI should industrialize expertise, not replace it. 00:00 - Cold Open 02:54 - Growing up in the family agency and the dinner-table boardroom 16:57 - Pitching Nationwide on a venture strategy 22:57 - Learning the venture business at SVB Capital 33:05 - Building the "SVB for insurance" 36:49 - Ten policies, then zero: fighting for product-market fit 39:37 - Vouch 2.0 and going all in on an AI-native brokerage 51:00 - The six elements of brokerage value and why speed is 40% 55:21 - When your client's insurance advisor is ChatGPT 01:00:21 - Quick fire: "Discipline is freedom for the happy warrior" Travis Hedge is the Co-Founder and CEO of Vouch Insurance, the AI-enabled brokerage for ambitious companies across technology, healthcare and life sciences, financial services, and professional services. He grew up in the insurance industry and spent his early career in venture capital at SVB Capital, where he saw firsthand how insurance gaps stalled fundraising, contract execution, and growth for fast-moving startups. He co-founded Vouch in 2018 with Sam Hodges, built its revenue engine as CRO, and became CEO in 2026. Today Vouch serves more than 6,000 clients and gives growing companies the guidance of a large enterprise long before they are one. Subscribe to Context Window for more insights from the operators deploying AI inside real insurance companies. See what Dearborn Labs is building: We don't just talk about AI in insurance, we build the technology that powers it. Explore our latest projects and partnerships at dearbornlabs.com

  5. Jul 16

    Why AI Rewards the Problem Owner | Steve Lekas, Co-founder & CEO of Branch Insurance

    Steve Lekas, Co-founder and CEO of Branch Insurance, unpacks the gritty reality of building a full-stack insurtech and cuts through the generative AI hype. As a 20-year insurance veteran who previously built the first U.S. online home insurance business at Esurance, Steve reveals the intense perseverance and deep economic understanding required to innovate in a legacy industry. Discover his "Shawshank Method" of career growth, why treating scalability as an early-stage goal is a trap, and why he believes the true benefits of AI will ultimately reward the "owner of the problem". 00:00 - The "Shawshank" Method of Perseverance 03:49 - Steve’s Origin Story: From Building PCs to Insurance 14:18 - The 2-Year HR Campaign to Get Into Allstate 43:07 - Building the World’s First Online Homeowners Product at Esurance 51:47 - The 10-Year Vision: Pitching Big Insurance 55:16 - Pitching Your Spouse and Finding a Technical Co-Founder 01:05:20 - The Hype Check: Where AI Actually Fails in Production 01:11:13 - Why Scalability is a Trap for Early-Stage Startups 01:23:18 - Why AI Rewards the Problem Owner Steve Lekas is the Co-founder and CEO of Branch Insurance, a full-stack insurance company that uses data, technology, and automation to make home and auto insurance simpler to buy and less expensive. A 20-year insurance veteran, Steve began his career at Allstate before moving to Esurance, where he built and launched the industry's very first platform allowing users to purchase homeowners insurance directly over the internet. Prior to founding Branch in 2017, he served as President of the Insurance Services Office's personal lines business for Verisk Analytics, and he currently serves as the Vice Chair of the Executive Committee for the American Property Casualty Insurance Association. Subscribe to Context Window for more insights from the operators deploying AI inside real insurance companies. See what Dearborn Labs is building: We don’t just talk about AI in insurance, we build the technology that powers it. Explore our latest projects and partnerships at ⁠dearbornlabs.com

  6. Jun 25

    You Can’t Automate a Process You Don’t Have | CJ Przybyl, Co-Founder and CEO of Reserv

    In the inaugural episode of "Context Window: AI, Insurance & The Humans Behind It,” we sit down with CJ Przybyl, co-founder and CEO of Reserv and adjunct professor at UChicago Booth, to cut through the generative AI hype. As a second-time Insurtech founder who has rapidly scaled Reserv to serve over 100+ clients, from tech-native MGAs to Fortune 500 carriers, CJ reveals the reality of building an AI-native third-party administrator. Discover why replacing humans was never the goal, and how his team is using AI to execute thousands of practical, operational upgrades that are actually transforming the insurance claims industry. 00:00 - The Cold Open: You Can't Automate What You Don't Have 01:40 - CJ’s Origin Story: From Motorola Flip Phones to Insurtech 18:50 - The Reality of Entrepreneurship vs. Investment Banking 26:20 - Catching the Car: Onboarding 90 People in 60 Days 41:20 - Lead Bullets vs. Silver Bullets: What Works in the Insurance Business 47:00 - The Strict ROI Trap Holding Legacy Carriers Back 54:10 - The Real AI Disruption: Infrastructure vs. Operations CJ Przybyl is the Co-Founder and CEO of Reserv, an AI-powered third-party administrator redefining the property and casualty insurance claims industry. A pioneer and second-time founder in the Insurtech space, CJ leads his team in leveraging human-centered technology and AI orchestration at scale to transform claims handling into a smarter, faster, and more transparent process. Beyond Reserv, he serves as an adjunct professor of entrepreneurship at the University of Chicago Booth School of Business. Subscribe to Context Window for more insights from the operators deploying AI inside real insurance companies. Connect with Kyle Nakatsuji on LinkedIn: https://www.linkedin.com/in/kylenakatsuji/  Connect with CJ Przybyl on LinkedIn: https://www.linkedin.com/in/cj-przybyl-9061383/  Learn more about Reserv: https://www.reserv.com/ See what Dearborn Labs is building: We don’t just talk about AI in insurance, we build the technology that powers it. Explore our latest projects and partnerships at https://dearbornlabs.com/

  • 6 Episodes

Ratings & Reviews

5
out of 5
3 Ratings

About

Welcome to Context Window: AI, Insurance & The Humans Behind It, the podcast for leaders, operators, and founders navigating the intersection of artificial intelligence and enterprise operations. Hosted by Kyle Nakatsuji, we discuss how real companies are deploying AI inside legacy industries like insurance, not as a hypothetical tech play, but as a practical blueprint powered by humans. Each episode features raw conversations with the builders and executives who are actually on the front lines managing data, scaling teams, and defining the future of business infrastructure.

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