InsurePodcast

Ben Shaw

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Entrepreneurship

InsurePodcast is Ben Shaw’s interview podcast about the people changing how insurance work gets done. Season 1 went inside independent insurance agencies. Season 2, Post-SaaS Insurtech, examines how AI is changing what insurance technology companies deliver, how they price it, and what customers can build on their platforms.

1d ago

InsurTech & SaaS #2: Fabio Faschi

The conversation explores the intersection of AI and insurance SaaS, focusing on the evolution of technology in the insurance industry and the implications for brokers and carriers. Fabio Faschi shares his journey from traditional insurance to the tech side, discussing the challenges and opportunities presented by AI in enhancing operational efficiency and customer service. The conversation explores the evolving role of AI in software development and organizational dynamics, emphasizing the balance between human expertise and AI capabilities. It discusses the implications of AI on productivity, decision-making, and the future of work, particularly in industries like insurance. Takeaways AI transforms insurance operationsBuilding vs. buying technology AI enhances productivityHuman expertise remains crucial Chapters 00:00 The Evolution of Insurance Technology03:57 Navigating the Broker's Experience with Technology10:35 The Build vs. Buy Dilemma in AI13:44 Customization and AI in Insurance Solutions18:04 Understanding Client Needs in AI Deployments21:31 The Evolution of AI in Software Development26:03 AI's Impact on Organizational Dynamics30:09 Navigating the Future of Work36:00 Skepticism and Trust in AI40:17 Embracing AI for Efficiency
Oct 13

InsurTech & SaaS #1: Chris Longano

The conversation explores the evolving landscape of SaaS in the insurtech space, focusing on the impact of AI, the shift towards outcome-based selling, and the changing needs of customers. Chris Longano shares insights from his experiences at various companies, including Rhoads and Noldor, highlighting the importance of adaptability and strategic partnerships in the industry. Takeaways AI is reshaping SaaS dynamicsOutcome-based selling is crucial Chapters 00:00 The Evolution of SaaS in Insurtech03:01 Headless SaaS and AI Integration06:00 The Role of Professional Services in AI09:05 Noldor's Approach to Reporting and AI11:48 Outcome-Based Selling in SaaS14:57 Rhoads: A Case Study in Insurtech18:12 Changing Customer Needs in Compliance20:56 The Future of Business Models in Insurtech24:05 Partnerships and OEM Strategies in SaaS
Jun 15

InsurePodcast #11: Eli Diamond

From a workers' compensation adjuster internship in college to building a commercial insurance book at one of the largest brokerages in the world, Eli Diamond has taken a somewhat unconventional path into insurance. Raised in Syracuse, New York, Eli began his career at The Hartford before moving to the agency side, where he discovered he preferred representing business owners rather than carriers. Today he works as a commercial producer at Gallagher following the acquisition of Tompkins Insurance, where he spent the first years of his brokerage career. In this conversation, Eli walks through what life actually looks like for a young producer building a book from scratch. We discuss prospecting, networking, cold calling, and the challenge of earning trust in an industry where many business owners have worked with the same broker for decades. He explains why he views the role as fundamentally consultative rather than sales-driven, and why relationships continue to matter more than almost anything else in commercial insurance. We also spend time on the mechanics of placing business. Eli explains how producers, account managers, marketing teams, wholesalers, and underwriters interact behind the scenes, how carrier appetites actually work in practice, and why certain classes—particularly construction and roofing risks in New York—can be difficult to place. Along the way we discuss cyber insurance, the current market environment, carrier relationships, and the role AI may eventually play in prospecting and account research. Finally, Eli reflects on what has surprised him most during his first few years as a producer, why so many people leave the profession early, and what keeps him motivated despite hearing “no” every day. It’s a candid conversation about persistence, specialization, relationship-building, and what it takes to succeed as a commercial insurance broker in today’s market. Show notes and transcript
Jun 1

InsurePodcast #10: Brian Mahon

Brian Mahon spent a decade inside startups and top-100 firms before launching Igloo Insurance in June 2025. One year in, he joins Ben to talk about what it actually takes to build an independent agency from scratch — and where the work still feels broken. We get into his multi-line book (roughly 60% commercial, 39% personal, the rest life), his cyber-liability niche, and the omnichannel hustle behind finding clients: Erie's brand pull, chambers and referral groups, cold calling done right, and direct mail. Brian walks through a real homeowner's quote from first phone call to bind, explains why personal lines collects more data than commercial, and maps the carrier-appointment maze that nobody hands you a guide for. The back half is about where AI can help an agency: prospect research, policy comparisons and underwriting narratives. Brian compares AI findings with human review and explains why quoting remains difficult to automate across carrier systems, report costs, coverage decisions and binding workflows. A candid, practical look at year one of agency ownership in South Central Pennsylvania. Show notes and transcript
May 23

InsurePodcast #9: Kristyn Ruth with Skye Saleh

Kristyn Ruth runs Think Pink Insurance out of Texas. She started in insurance the way few people do: she'd been selling cars for eighteen years, opened a dealership in 2018, and didn't want to keep referring her finance customers out to other agents — so she got licensed and started writing the policies herself. Eight years later she runs a multi-line operation with seventy-seven agents across forty-plus states, spanning P&C, life, annuities, and group benefits. Her business partner is Skye Saleh, who came from a counseling, medical-administration, and chief people officer background. They met as client and agent, became friends, and formed a separate group benefits agency together in 2024 — Skye bringing the inside-the-HR-department perspective that most benefits brokers don't have. This is the first episode of the show focused on group benefits, and a useful contrast to the personal lines and small commercial conversations that have come before. Skye walks through what a typical day looks like for a benefits broker — getting census data, working through the general agency, the back-and-forth on pricing when the employer hits sticker shock. Kristyn explains the recruiting-led structure of her P&C side: how she finds independent agents through Alignable, how Go High Level holds the agency together, and how she runs the carrier panel across forty states while still picking up three new appointments in a single week. The conversation goes in a different direction from most episodes. Less time on the placement workflow, more time on what Kristyn calls mindset — the part of running an agency that most operators underestimate. We talk about the servicing burden that surprises new agents, the chargeback problem that comes with selling something a customer can't afford long-term, and Kristyn's unusual recruiting philosophy: she'll plug agents into training and back-office support, but she has no patience for producers who won't figure things out themselves. Skye offers the counterweight, framing the same work through the lens of pouring into people and growing the mindset before chasing the close. Show notes and transcript: https://insurepodcast.com/episodes/season-1/group-benefits-multi-state-agency-kristyn-ruth-skye-saleh Kristyn: LinkedIn · Skye: LinkedIn
May 22

InsurePodcast #8: Doug Wenz

Doug Wenz is Vice President at Associated Insurance Services in Plainville, Connecticut. He's been licensed since 2017 and has spent fifteen years in sales — the kind of producer whose LinkedIn tagline reads "Challenging Insurance Industry Norms" and who means it. He got into insurance the way few people do: lightning struck his car overnight, GEICO fought him on the claim, and after he won the fight (and almost didn't get handed the check at the office), he told the story at a BNI meeting where a producer at BearingStar Insurance recruited him on the spot. In the eight years since, Doug has built something unusual. After spending five years at his previous firm running personal lines and learning commercial the hard way, he pivoted to a business model that runs almost entirely on referrals from other producers. A producer at another agency who can't write a New York Labor Law contractor account — or any other hard commercial risk — calls Doug. He swims in the contractor space, lives comfortably in surplus lines, and works closely with R-T Specialty, CRC, and RPS. We get into his typical day (meditation at 5:30, no meetings before 11), the carrier panel he runs across The Hartford, Travelers, Chubb, and Acadia, and why the marketing reps make or break a carrier relationship. We talk through the workflow texture. The data-gathering problem that no startup has solved despite many trying. The supplementals and loss runs that are his biggest pet peeve — including a sharp take on The Hartford's new system that sends a link to the insured rather than sending loss runs directly. Why the commission economics of personal lines make it nearly impossible to serve a $1,000 home policy well, and how that compound problem is breaking the industry. Where he sees AI fitting in — eliminating the marketing person on the front end so the producer can do the work with the client directly — and a sharp warning about hallucinations after a viral LinkedIn post where someone showed an AI fabricating an entire second life insurance quote and nobody in the comments noticed. His through-line is education. Doug wants to train the next generation of producers — not because he's nostalgic, but because the system is broken in ways the corporate structure can't fix. He keeps coming back to a single point throughout the conversation: most insureds don't know what they don't know, and that asymmetry is the industry's deepest problem. Show notes and transcript: https://insurepodcast.com/episodes/season-1/contractor-insurance-surplus-lines-doug-wenz Doug and Associated Insurance Services: LinkedIn
May 22

InsurePodcast #7: Brandy Henriquez with Tom Polowy

Note: this episode recording got interrupted, so there's a sharp cut halfway through. Brandy Henriquez and W. Tom Polowy run Insure Connecticut, an independent brokerage based in West Hartford and licensed in seventeen Eastern states. Brandy came to insurance from twenty years in radio and entertainment production. After looking at real estate and insurance as his next chapter, he landed at a State Farm captive in May 2022, ran it for two and a half years, and left when the captive model stopped letting him serve his customers the way he wanted to. Tom started his own agency during what he calls "the P&C apocalypse" of COVID — a period when carriers were closed to new appointments and there was almost nothing to write. The two of them partnered in 2024: Brandy oversees personal and commercial insurance, Tom focuses on wealth management, and together they run a content studio with podcast rooms on the side. In this conversation we get into how Insure Connecticut operates differently from most independent brokerages. Brandy walks through the AI workflow they've built around Cara — feeding carrier appetites into an AI tool that helps them figure out who to quote a hard Connecticut property with before they ever pick up the phone. We talk about their carrier panel — about twenty for home, twelve for auto, plus wholesale through Burns & Wilcox and others — and their internal "Alan," the guy on the phone with underwriters who solves whatever Cara can't. We get into the workflow texture: SOPs by line of business, dec page and ACORD form intake, and the limits of every AMS and rater on the market. Tom is sharper than most agency owners on marketing strategy. He talks about why most agencies aren't actually running businesses — they're just existing, buying leads, doing what they've always done. Insure Connecticut runs eighty to a hundred leads a month, almost entirely through SEO, with referral partnerships from real estate and mortgage professionals layered on top. We get into what he's learning about AI engine optimization — including a regular stream of referrals from ChatGPT and Claude that he didn't believe when it first started happening — and his honest take on why no startup has solved the agency workflow problem yet despite many trying. Brandy closes with a reminder that gets lost in the scaling race: a lead is a person with a problem. Show notes and transcript: https://insurepodcast.com/episodes/season-1/insurance-agency-seo-ai-brandy-henriquez-tom-polowy Brandy, Tom, and Insure Connecticut: myinsurect.com
May 22

InsurePodcast #6: Sydney Troski

Sydney Troski has been licensed in life and health insurance since 2023. Based in Boiling Springs, South Carolina, she works as an independent life insurance agent under an IMO, focusing on whole life, term life, and mortgage protection for families and individuals. She is one of the younger agents on the show and one of the few who came in without a long runway of capital — which means everything she's learned, she's learned by doing it wrong first and then doing it again. Sydney has switched IMOs five or six times by her own count. Each move taught her something: what a recruiting-first model actually looks like from the inside, how compensation structures get designed to benefit the upline rather than the producer, and why some carriers have a reputation for not paying claims. She now works with a company whose CEO built a proprietary quoting tool that matches clients to the most likely approval at the best rate — something she says she wished existed from day one. In this conversation we get into what the daily grind actually looks like for an agent who is still building. The morning dial sessions — sometimes a hundred calls, sometimes five hundred — and the mental reset she has to take in between. The lead buying math: why it works, why it fails, and why recycled leads are a gamble every time. The organic marketing she does through Facebook groups and why the timing problem makes it mostly a long shot. We also get into the moment a former client called to warn her that someone from her first company was trying to flip her policies — and what that says about the parts of this industry that nobody talks about in the recruiting pitch. Sydney is honest about where she is, what she got wrong early, and what she thinks it actually takes to get to $15,000 to $20,000 a month on your own pen. Show notes and transcript: https://insurepodcast.com/episodes/season-1/life-insurance-leads-imo-lessons-sydney-troski Sydney Troski: LinkedIn

InsurePodcast is Ben Shaw’s interview podcast about the people changing how insurance work gets done. Season 1 went inside independent insurance agencies. Season 2, Post-SaaS Insurtech, examines how AI is changing what insurance technology companies deliver, how they price it, and what customers can build on their platforms.

Creator

Ben Shaw
Years Active

2026
Episodes

13
Rating

Clean
Copyright

© 2026 Ben Shaw
Show Website

InsurePodcast