Shows
Insurtechs.ioRevolutionizing Insurance Settlements with Shannon Elsea, Founder of SettlementDoneEasyIn this episode of Founders Journey, Jeff sits down with Shannon Elsea, founder of SettlementDoneEasy, to explore how his platform is transforming the settlement payment process for insurers and law firms. With over 30 years of experience as a personal injury lawyer, Shannon shares his first-hand insights into the outdated paper check system that has led to increased delays, theft, and fraud—costing insurers billions. He explains how Settlement Done Easy eliminates these risks by enabling secure ACH payments directly from carriers to law firms, ensuring faster, safer, and more cost-effective transactions. Shannon also discusses shifting consumer expectations for digital pa...
2025-10-0816 minInsurtechs.ioNavigating Capital Raising, Advisory, and Emerging Trends in insurtech with Jeffrey FidelmanIn this episode, host Jeff Shi sits down with Jeffrey Fidelman, an investment banker and founder with extensive experience helping early-stage companies secure funding and scale. Jeffrey shares his journey from Morgan Stanley and HSBC to launching his own advisory firm, where he pioneered a "fundraise as a service" model. The conversation dives deep into capital raising strategies, the evolution of insurtech, and the critical role of advisory in building sustainable insurance businesses. Jeffrey discusses his first-hand experiences structuring innovative insurance carriers, navigating reinsurance markets in Bermuda, and advising insurtech founders from seed through...
2025-10-0140 minInsurtechs.ioUnlocking QSBS for Startup Founders with Christopher KarachaleIn this episode, host Jeff Shi welcomes Christopher Karachale, a leading tax attorney and expert on Qualified Small Business Stock (QSBS). They dive deep into what founders, investors, and early employees need to know about QSBS and how it can dramatically reduce tax liability during an exit. Christopher explains the mechanics of QSBS—from original issuance and the $50M gross assets test to the five-year holding requirement—while also clarifying common pitfalls around LLC conversions, S-corp elections, and secondary sales. The discussion highlights how insuretech founders can maximize their eligibility, whether through structuring early, leveraging IP contributions, or using adva...
2025-09-2436 minInsurtechs.ioStartup Law, Founder Equity & VC Strategy with Vikas SrinathIn this episode of Founders Journey, Jeff Shi sits down with Vikas Srinath, Partner and Innovation Leader at Prospera Law, to unpack the legal and strategic frameworks that fuel early-stage startups. Vikas shares his path into startup and venture law, his approach to working with both founders and investors, and how Prospera Law serves as a critical partner throughout the startup lifecycle. The discussion dives deep into common blind spots in founder legal planning, building scalable legal infrastructure, startup equity strategy, investor dynamics, and how insurtech and AI are reshaping startup law in 2025. Vikas also offers insight...
2025-09-1725 minInsurtechs.ioFrom Allstate to AI: Sarah Caputo’s Journey to Fraction Method and the Future of Marketing StrategyIn this episode of Founders Journey, Jeff Shi sits down with Sarah Caputo, a powerhouse marketing leader whose career has spanned Fortune 500 insurance giants, insurtech startups, and now her own venture, Fraction Method. Sarah shares how she built her career without a college degree, rising through the ranks at Allstate, spearheading digital transformation, and leading the marketing function at Plank, an AI-powered insurtech platform that was recently acquired.The conversation dives deep into Sarah’s evolution from agency life to in-house strategy, the strategic challenges of marketing intangible products like insurance and SaaS, and th...
2025-09-1032 minInsurtechs.ioAI-Driven Servicing for Modern Insurance Agencies with Nikhil KansalIn this episode of Founders Journey, Jeff sits down with Nikhil Kansal, co-founder and CTO of Oyster, to explore how a deep-rooted tech background is shaping the future of insurance. Nikhil shares his story, from tinkering with computers as a child to working at Stripe, and eventually launching Oyster—a company built on the belief that insurance can be transparent, efficient, and digitally driven.This episode covers Oyster's evolution from embedded personal insurance to its current model: providing AI-powered software for insurance agencies and brokerages. Nikhil dives into the company’s transition from a digital brokerage to a so...
2025-09-0323 minInsurtechs.ioBuilding Tomorrow's Insurance Leaders with Alyssa Bouchard of Gamma Iota SigmaIn this episode of Industry Voice, Jeff welcomes Alyssa Bouchard, Senior Vice President, Development at Gamma Iota Sigma (GIS), the national collegiate talent pipeline for the insurance industry. Alyssa shares her inspiring journey from student member to national leader, highlighting how GIS empowers future insurance professionals through scholarships, mentorship, and immersive career experiences.She breaks down how GIS bridges the gap between students and employers across carriers, brokers, TPAs, and the growing insurtech space. With 113 chapters and over 6,000 students across 167 universities, GIS is creating a diverse and well-rounded workforce equipped with both technical knowledge...
2025-08-2729 minInsurtechs.ioBuilding Insurance Brands: Legacy vs. insurtech with Erich de OliveiraIn this episode of Industry Voice, Jeff sits down with Erich de Oliveira, a seasoned marketing executive with two decades of experience across B2B and B2C sectors, including leadership roles at Simply Business and Corvus Insurance. Erich dives deep into what it means to build a brand from the ground up, especially in the insurtech world where trust and clarity are paramount.From his early days as employee #3 at Simply Business to leading marketing at legacy carriers, Erich shares the stark contrast between startup marketing and enterprise brand strategy. He unpacks how...
2025-08-2028 minInsurtechs.ioFrom Bootstrapped Startups to AI-Powered Lead Optimization: Scott Shou’s Founder JourneyIn this powerhouse episode of Founder's Journey, Jeff Shi sits down with Scott Shou, serial entrepreneur and current founder of Boardwalk Marketing. With two major exits under his belt before finishing college—including a $10M+ web hosting startup and a $40M+ exit for a car dealer CMS—Scott shares deep insights into startup growth, team dynamics, and product-market fit. From running high-volume lead gen experiments at Cogo Labs to launching his latest venture, Scott details how Boardwalk Marketing is turning non-monetized traffic into revenue gold for lead gen and performance marketers. You’ll hear how his unique “Shopify for marketin...
2025-08-1344 minInsurtechs.ioThe Evolving World of Insurance Media: Greg Crawford on 35+ Years in Journalism and P&C InsightsIn this episode of Industry News, Jeff sits down with Greg Crawford, editor at FT Specialist and a seasoned journalist with over 35 years in the media industry. Greg takes us on a journey through his storied career—from his start at AM Best and fast-paced reporting at Reuters during the Gulf War, to covering financial markets in Hong Kong and eventually landing in the insurtech world via P&C Specialist. Greg shares the changing landscape of insurance journalism, the importance of curiosity in newsrooms, and why property and casualty insurance is far from boring. He...
2025-08-0646 minInsurtechs.ioFrom Bootstrapped Startup to Vertafore Acquisition: The AgencyZoom Journey with Moe LatifIn this episode of Founders Journey, Jeff sits down with Moe Latif, co-founder of AgencyZoom, to talk about how a side project turned into one of the most beloved CRM platforms in the insurance industry and ultimately led to a successful acquisition by Vertafore. Moe shares how he and his co-founders identified a simple but critical problem in the insurance onboarding process and built a solution that quickly spread by word-of-mouth.This episode explores the scrappy early days—lugging duct-taped booths to conferences, sharing hotel rooms, and reinvesting every dollar back into the business. Mo...
2025-07-3047 minInsurtechs.ioRevolutionizing Insurance Payments: Greg Mallin on Agave Pay’s Vision for the FutureIn this episode of Industry Voice, Jeff sits down with Greg Mallin, a seasoned payments executive and Co-Founder of Agave Pay, to explore how payments are being reimagined in the insurance space. Greg shares his 25+ year journey through fintech, credit, and consumer finance before entering the world of insurance and transforming a legacy system plagued by inefficiencies. Learn how Agave Pay is streamlining workflows, enabling digital payments for carriers, MGAs, and agencies, and solving real pain points in a trillion-dollar industry. The conversation also dives into AI’s role in automating renewals and cancellations, th...
2025-07-2331 minInsurtechs.ioThe Future of Insurance Innovation: Lessons from History with Steve AndersonIn this episode, we sit down with Steve Anderson, best known for his work with The Bezos Letters, to explore how the past informs the future of innovation in the insurance industry. Steve shares his deep knowledge of insurance, technology, and risk, drawing from decades of experience to help founders, carriers, and investors understand what truly drives transformative growth. From Jeff Bezos’ leadership principles to the adoption curve of new technologies, this episode is packed with insights on how traditional insurers can embrace change and how insurtech founders can navigate resistance in legacy systems. Steve also discusses the biggest mi...
2025-07-1644 minInsurtechs.ioAI Infrastructure, Gen AI Reliability, and Scaling Smart with Kevin McGrath of Meibel AIIn this episode of Industry Voice, Jeff Shi and Alex Moy welcome Kevin McGrath, co-founder of Meibel AI, for a deep dive into how product and engineering teams can operationalize generative AI with confidence. Kevin shares insights from decades of experience in infrastructure at scale, explains Meibel’s unique approach to AI reliability via measurement and confidence scoring, and reflects on how gen AI democratizes capability across industries. From building billion-dollar businesses with lean teams to identifying overlooked sectors ripe for AI transformation, this episode is packed with actionable insights for builders in insurtech, fintech, and beyond. Kevin also di...
2025-07-0954 minInsurtechs.ioNavigating Venture Capital & Insurtech Evolution with Dave WechslerIn this episode of Insurance VC, PE, and M&A, host Jeff Shi sits down with Dave Wechsler, Principal at OMERS Ventures, for a deep dive into the evolving landscape of venture capital and insurtech. Dave shares his unconventional path from launching startups to leading one of the most active fintech and insurtech investment portfolios. He offers founders a transparent look into the venture capital mindset, including how funds decide where to invest, the importance of matching stage and thesis, and why most pitches get rejected. Dave and Jeff explore insurtech’s journey from 1.0’s disruptive beginnings to today’s 2.0...
2025-07-0256 minInsurtechs.ioCorrell and PerezIn this episode of Industry Voice, Jeff Shi sits down with Andrew Correll and David Perez, the driving forces behind InsurTech ATX — Austin's thriving grassroots insurtech community. They share the origins of InsurTech ATX, which started as a humble meetup in 2016 and has grown into a vibrant, international hub for insurance and tech professionals. Andrew and David recount how they transitioned into leadership during the pandemic and scaled the group through community engagement, thoughtful programming, and strategic sponsorships. The episode dives into how Austin’s unique mix of insurance talent and tech innovation fosters insu...
2025-06-2749 minInsurtechs.ioThe Entrepreneurial Rollercoaster of insurtech and Beyond with Jeffery ArnoldIn this engaging episode of Industry Voice, host Jeff Shi sits down with serial entrepreneur and best-selling author Jeff Arnold. The conversation delves deep into Arnold’s dynamic journey through insurance, insurtech, private equity, and even professional sports ownership. Jeff shares how he went from stand-up comedy in North Hollywood to building and exiting multiple tech and insurance ventures, including RightSure, Lender Bridge, and Lender's Portal. With ten books under his belt—five of them Amazon #1 bestsellers—Jeff reflects on how he transformed academic struggles into thought leadership through discipline and creativity. He opens up abo...
2025-06-2538 minInsurtechs.ioNavigating IPOs, SPACs, and AI Valuations in insurtech with Michael BlankenshipIn this insightful episode, Jeff Shi is joined by Michael Blankenship, Partner at Winston & Strawn and Managing Partner of the Houston office, to unpack the current and future landscape of IPOs, SPACs, and M&A within the insurtech and broader insurance industry. Michael brings nearly two decades of legal and capital markets expertise to the conversation, offering founders, executives, and investors practical guidance on public company readiness, regulatory navigation, and capital strategy.The episode covers the evolution and regulation of SPACs, why the market cooled, and what a potential rebound might look like. Michael...
2025-06-2330 minInsurtechs.ioNavigating the M&A Landscape for Independent Agencies with Mike Mensch & Colby AllenIn this powerhouse episode of Insurance VC, PE, and MA, host Jeff Shi is joined by Michael Mensch and Colby Allen from Agency Brokerage Consultants to explore the complex, ever-evolving landscape of mergers and acquisitions in the independent insurance agency space. With over 500 transactions under their belt, Mike and Colby share insights that are invaluable for any agency owner thinking about growth, preparing for an exit, or understanding their agency's valuation. They dive deep into the foundational mistakes agency owners make, the difference between valuations and real-world value, and how to strategically prepare for an optimal exit. The conversation...
2025-06-2050 minInsurtechs.ioFrom Captive Agent to annuity Leader: Tracy Lownsberry on Scaling Education-Driven SalesIn this powerful episode, host Jeff Shi sits down with Tracy Lownsberry to unpack his evolution from a captive insurance agent to the founder of the largest social media community for annuity professionals. Tracy shares how his early experiences shaped a deeper commitment to transparency, education-based sales, and doing business the right way. He dives into building Annuity Giants Agents Academy, a subscription-based training model that’s reshaping how agents and advisors learn about annuity sales — without the usual recruiting strings attached.Tracy opens up about leveraging AI and CRM tools to scale his prac...
2025-06-1832 minInsurtechs.ioNavigating M&A, Lending, and Growth Strategies in the Insurance Industry with Kelly DrouillardIn this episode of Insurance VC, PE, and M&A, Jeff Shi sits down with industry icon Kelly Drouillard to unpack the complexities of insurance M&A, lending strategies, and agency growth. With over 30 years of experience spanning carrier, reinsurance, and capital markets, Kelly brings a deep well of insight into insurance transactions. She breaks down the agency ownership lifecycle—from growth and optimization to perpetuation—while offering tactical advice on when and how to sell.Kelly also explains the nuances between SBA 7A loans and traditional bank lending, the risks and rewards of equi...
2025-06-161h 15Insurtechs.ioBuilding Scratch Agencies & Podcasting Community with Sean Fitzgerald & Stephen TurnbullIn this episode, host Jeff Shi welcomes Shawn Fitzgerald and Stephen Turnbull, the dynamic duo behind the Scratch Agency podcast. Together, they share their journey of launching their own scratch agencies in New York and how their similar-but-different paths led to the creation of a podcast that has grown into a vibrant community for independent insurance agents.They dive deep into their reasons for documenting their journey, the importance of community and mentorship, and how their mastermind group is helping scratch agents across the country avoid costly mistakes. The episode also explores how regional...
2025-06-1341 minInsurtechs.ioBootstrapping a Flood MGA: Inside Flow Flood's Growth Story with Abbe Sulton & Michael PallasIn this episode, host Jeff Shi sits down with Flow Flood co-founders Abbe (A.B.) Sulton and Michael Pallas to explore their unique path from insurance distribution to building a flood-focused insurtech MGA. The conversation dives deep into their early days running a retail agency during the 2008 financial crisis, discovering market inefficiencies in residential flood, and evolving into a full-stack digital MGA with multiple binding agreements across 43 states. A.B. and Michael share their strategies for leveraging SEO, digital distribution, and legislation changes to grow their flood book, how their trip to Lloyd’s of London unlocked new reinsurance pa...
2025-06-1138 minInsurtechs.ioGlobal Insurance Transformation, Community, and the Power of Mindset with Rory YatesIn this thought-provoking episode, Jeff sits down with Rory Yates, Group Vice President of Corporate Strategy at EIS, to explore his dynamic journey from a tech-savvy athlete to a global leader in insurance transformation. Rory opens up about growing up in poverty, using sports to earn an education in the U.S., and his pivot from launching one of the first internet banks in the UK to helping reshape the global insurance landscape.The conversation dives deep into how legacy mindsets—not legacy technology—are holding the industry back, why true transformation requires customer-centric plat...
2025-06-0936 minInsurtechs.ioFixing the Insurance Data Problem: Roman Stepanenko on Conversions, Governance & RecordLinkerIn this episode of Founders Journey, Jeff sits down with Roman Stepanenko, founder of Record Linker and co-founder of RiskMatch. Roman shares his fascinating transition from software developer to insurtech entrepreneur, starting with the creation of RiskMatch and continuing with his latest venture, Record Linker.They dive deep into the overlooked and often painful world of insurance data conversions and governance. Roman breaks down how legacy systems, poor reference data quality, and post-M&A chaos affect brokers—especially those trying to centralize operations. He explains how Record Linker uses machine learning to drastically reduce ma...
2025-06-0632 minInsurtechs.ioHow Melon Local Became a Powerhouse for Insurance Marketing with Whitney OlsonIn this episode of Founders Journey, Jeff sits down with Whitney Olson, co-founder and CEO of Melon Local, to unpack the story of how a boutique digital marketing agency became a trusted partner for some of the nation's top insurance agents. Whitney is joined by Senior Director of Paid Search, Megan, and Senior Director of Business Development, Katie Olson, to share how Melon Local turned a living-room startup into a 70-person team spending over $2.5 million a month on paid media.Whitney shares how her background in hospitality and her husband’s experience as a to...
2025-06-0421 minInsurtechs.ioThe Evolution of insurtech with Denise Garth, Chief Strategy Officer at MajescoIn this powerful episode, Jeff sits down with insurtech trailblazer Denise Garth, Chief Strategy Officer at Majesco. With over three decades of experience in both business and IT across insurance carriers, vendors, and global industry organizations, Denise brings unmatched insight into the evolution of the insurtech landscape. From launching Majesco's now top-ranked podcast to being one of the earliest voices championing digital transformation, Denise unpacks the industry's decade-long journey with technology, the shift from legacy systems to GenAI, and what innovation truly means for carriers today. Denise shares how she foresaw the impact of...
2025-06-0246 minInsurtechs.ioRevolutionizing Insurance Tech and Lead Gen with Steve MohrIn this episode of Industry Voice, we sit down with Steve Mohr, a seasoned insurance technology entrepreneur and founder of The Insurance Index. Steve takes us through his multi-decade journey in the insurance and insurtech space, from starting out as a producer in Florida’s non-standard auto market, to building revolutionary agency management tools, and now leading lead generation and distribution efforts for NowCerts through his new platform, LeadX.We dive into the pivotal moments of Steve’s career—his early success with eAgent in the Allstate ecosystem, his transition to LightSpeed Voice, and how he...
2025-05-3034 minInsurtechs.ioThe Evolving Role of Strategic Partnerships in Insurance Distribution with Jeff PireuIn this episode of Industry Voice, host Jeff Shi sits down with Jeff Pireu, Vice President of Strategic Partnerships at First Choice, a MarshBerry company. With over 30 years in the insurance industry—spanning claims, sales, and executive leadership roles at Nationwide—Jeff shares his journey from carrier-side leadership to the forefront of agency distribution. The conversation dives into the complexities of building scalable strategic partnerships, filtering insurtech solutions for real agency ROI, and creating tech councils that help vet emerging tools for First Choice members. Jeff also discusses how First Choice distinguishes itself in the competitive aggregator and franchise ecos...
2025-05-2836 minInsurtechs.ioRethinking Insurance Distribution with Patrick TulliusIn this episode, host Jeff Shi sits down with Patrick Tullius, Managing Director at INS Capital Group, to dive deep into the evolving world of insurance distribution, insurtech innovation, and the critical role of MGAs in bridging the gap between carriers and cutting-edge technologies. Patrick brings his extensive experience in investment banking and his unique perspective on raising capital, building programs, and aligning incentives between underwriters and distributors. The conversation explores why the most successful MGAs have deep actuarial roots, how embedded insurance can scale across verticals, and what VCs should really be looking for when evaluating insurtech opportunities...
2025-05-2633 minInsurtechs.ioHow to Sell an Insurtech Startup in a Down Market with Daniel MetcalfIn this episode, we sit down with Daniel Metcalf, co-founder of Smart Harbor, to explore the complete lifecycle of building and exiting an insurtech business. Daniel shares the origin story of Smart Harbor, a company born out of the belief that independent insurance agents needed modern digital tools to compete with direct writers. He talks about the company's evolution from its startup days to a strategic acquisition by Vertafore, revealing hard-earned insights into timing the market, building valuable tech for a niche audience, and navigating a sale in a down market. Daniel also reflects on what founders often get...
2025-05-2332 minInsurtechs.ioEmbedded Insurance, Risk Carriers, and insurtech Innovation with Theresa Blissing & Michael WaitzeIn this episode of Insurtechs.io, host Jeff Shi is joined by Theresa Blissing and Michael Waitze to unpack the dynamic evolution of embedded insurance, the strategic role of risk carriers, and what drives the next generation of insurtech innovation. The conversation dives deep into how customer-centricity is reshaping product development, the differences between U.S. and Asia-Pacific markets, and the broader implications of trust, distribution, and underwriting in modern insurance. Tony and Michael share their extensive industry perspectives—from the necessity of regulation to tech-driven disruption—and challenge listeners to think differently about how insurance can be more incl...
2025-05-211h 06Insurtechs.ioBuilding a Software-Enabled Underwriting Company with Bobby TouranIn this episode, Jeff Shi sits down with Bobby Touran, the two-time founder and CEO behind leading insurtech startups Pathpoint and Rainbow. Bobby shares his journey from building software-driven companies to founding two specialized underwriting and distribution platforms within the commercial insurance space. Hear how Bobby transitioned from the world of engineering-led startups into surplus lines brokerage and eventually launched Rainbow—a software-enabled underwriting company focused on niche commercial markets like restaurants and wellness.Bobby dives deep into the differences between building his first and second insurtech startup, the evolution of fundraising in today's ma...
2025-05-1944 minInsurtechs.ioUsing AI to Drive Underwriting Efficiency at Scale with Sarah Reeves & Matthew SutikaIn this episode, we dive into the future of underwriting transformation with Steve Reeves, Chief Insurance Officer at Voxel, and Mico Sutika, VP of Sales. Hosted by Jeff Shi, this conversation explores how Voxel is applying advanced AI and machine learning technologies to solve long-standing inefficiencies in commercial underwriting. From automating data ingestion to surfacing high-quality leads and improving the underwriter experience, Steve and Mico break down the mechanics of deploying AI in real-world workflows. They also discuss how to think about ROI when evaluating insurtech vendors, the gap between carrier innovation goals and actual execution, and what the...
2025-05-1653 minInsurtechs.ioFrom the NFL to Insurtech Vegas: Marcus Ogden’s Unbreakable Mindset and Story of RedemptionIn this powerful episode of Industry Voice, Jeff sits down with Marcus Ogden — former NFL offensive lineman turned motivational speaker, entrepreneur, and insurtech advocate. Marcus opens up about his extraordinary journey from football stardom to personal and professional rock bottom, and how he clawed his way back through grit, authenticity, and purpose. He recounts the collapse of his multimillion-dollar construction business, the humbling reality of working as a custodian, and how those trials forged the mindset that now fuels his mission to help others break through adversity. From NFL locker rooms to insurtech ITC Vegas stages, Marcus shares why bu...
2025-05-1237 minInsurtechs.ioCrypto Meets Insurance: Risks, Regulation & Real-World Use CasesIn this episode of Industry Voice, Jeff Shi sits down with two industry veterans, Susan Holliday and David Crosbie, for a deep dive into the intersection of crypto, blockchains, and the insurance world. Susan shares her extensive experience leading strategy at Swiss Re and her early encounters with blockchain technology, while David recounts his transition from teaching crypto at UPenn to serving as a crypto advisor at the SEC during pivotal cases like FTX and Terraform Labs. The trio explores practical use cases for blockchain in insurance, the emergence of stablecoins, challenges in underwriting crypto companies, the importance of...
2025-05-1238 minInsurtechs.ioModernizing Insurance Sales Enablement with Caleb Cramer of LaunchIn this episode of Industry Voice, Jeff Shi is joined by Caleb Cramer, Chief Revenue Officer of Launch. Caleb shares his journey from traditional B2B sales into the insurance space and discusses how Launch is transforming the producer-client relationship. From his days at AgencyZoom and Ascend to helping agencies improve enterprise risk management through Launch’s unique assessment and action-planning tools, Caleb is on a mission to empower insurance sales teams with cutting-edge, easy-to-use technology. Learn how Launch helps producers identify niche markets, quantify risk, and guide clients beyond the premium, while increasing close rates and improving client al...
2025-05-0920 minInsurtechs.ioNavigating Executive Search in Insurtech: Clarity, Talent, and Market Trends with Ira ZiffIn this episode of Industry Voice, we sit down with Ira Ziff, a veteran in executive search with nearly three decades of experience. Ira shares his expertise on bringing clarity to hiring strategies in the insurtech sector, offering insight into the challenges of dysfunctional job descriptions, retention issues, and misaligned expectations between employers and candidates. From his recent experience at the Connected Claims Conference to advice on fractional talent and navigating emerging markets, Ira unpacks key strategies for growing companies and professionals looking to make their next move. This episode is a must-listen for hiring managers, founders...
2025-05-0724 minInsurtechs.ioBuilding Community & Talent in insurtech with Josh HollanderIn this episode of Industry Voice, host Jeff Shi welcomes Josh Hollander, President of Horton International USA, host of the insurtech Leadership Podcast, and co-founder of the insurtech Association. Josh shares his remarkable journey from investment banking and fintech entrepreneurship to becoming a key community builder and talent strategist in the insurance and insurtech ecosystem. The conversation explores Josh’s early experience co-founding a robo-advisor platform in the 90s, his transition into executive search, and his leadership in launching initiatives like the Hartford InsurTech Hub and Imagine Incubator. Josh also discusses the patterns he’s seen across over...
2025-05-0531 minInsurtechs.ioFrom Selling Shoes to Building a $15M Insurance Empire with Dan KitajimaIn this episode of Industry Voice, host Jeff Shi welcomes Dan Kitajima, founder of one of the largest farmer’s insurance agencies in California. Dan shares his journey from working at a sneaker store in college to becoming a top-performing insurance agent. He opens up about the grind of building his agency from scratch—starting with two people in a shared conference room—and scaling to over 22 licensed agents and nearly $15M in annualized premium.Dan dives deep into the pivotal moments that shaped his business: the leap of faith into a high-rent office, the tr...
2025-05-0236 minInsurtechs.ioBuilding Careers in Insurance Through TikTok and Empowerment with Samantha RidgewellIn this episode of Industry Voice, Jeff Shi sits down with Samantha Ridgewell, Managing Director of Empower Development, to explore how social media—particularly TikTok and LinkedIn—can reshape the way young professionals discover and enter the insurance industry. Samantha shares how her engaging content has influenced over 200 people to find roles in the London insurance market, and offers an insider’s look at Lloyd’s of London, including the unique culture, ecosystem, and generational shifts within the market. From building community through creative digital content to founding her own company while on maternity leave, Samantha’s story is a...
2025-04-3045 minInsurtechs.ioBuilding a Legacy of Impact: From Insurance to Philanthropy with Anthony GruppoIn this powerful episode of Insurance Dads, hosts Matt Sutika and Jeff Shi sit down with the ever-inspiring Anthony Gruppo—a serial entrepreneur, board chair, author, and philanthropist. Anthony opens up about his incredible journey from blue-collar beginnings and early sales jobs to leading major organizations like USI and Marsh, and ultimately founding Vantage Insurance Partners. But what truly sets Anthony apart is his unwavering commitment to making a difference through his family's foundation, which supports autism programs and senior care.Anthony shares how personal experiences, including being a foster parent and having a gr...
2025-04-2842 minInsurtechs.ioTransforming Insurance Through Embedded Distribution: Charles Merritt on Building BuddyIn this episode of Founders Journey, host Jeff Shi sits down with Charles Merritt, co-founder and CEO of Buddy, to unpack his entrepreneurial path from cinematography and tech startups to founding a pioneering insurtech platform. Charles shares how his curiosity and creativity led him from media production to product innovation, ultimately co-founding Buddy to make insurance more accessible through embedded and ecommerce-ready distribution. He explains the original vision behind Buddy’s on-demand accident coverage, the challenges and lessons from launching during the pandemic, and the company’s pivot to becoming an enterprise SaaS platform for insurance carriers.
2025-04-2546 minInsurtechs.ioFrom Engineer to insurtech Founder: Sivan Iram’s Journey with Flow SpecialtyIn this episode of Founders Journey, host Jeff Shi sits down with Sivan Iram, Co-Founder and CEO of Flow Specialty. From coding in his childhood bedroom in Israel to navigating the complexities of venture-backed growth in Silicon Valley, Sivan shares a detailed, candid look into his entrepreneurial journey. He talks through his transition from software engineering to business leadership, the genesis of Flow, and how he and his co-founders identified a gaping opportunity in the wholesale and specialty commercial insurance market.Sivan dives into the highs and lows of fundraising—raising $20M across seed an...
2025-04-231h 10Insurtechs.ioBuilding Better Insurance with Data, AI, and a Mission-Driven Mindset with Martin EllingsworthIn this episode of Industry Voice, host Jeff Shi sits down with analytics and insurance veteran Martin Ellingsworth. With a career spanning over four decades—from the Air Force to corporate America to startup culture—Martin shares invaluable insights on transforming the insurance industry through data, ai, and human-centered innovation. The conversation explores the evolution of analytics in insurance, from the early days of fraud detection models and unstructured data to today’s potential with tools like ChatGPT and AI-enhanced image recognition. Martin reflects on his work with giants like Fireman's Fund, USAA, and J.D. P...
2025-04-2142 minInsurtechs.ioFrom $16M Exit to Building Intelligent Agencies with Mick HuntIn this episode of Industry Voice, Jeff sits down with Mick Hunt—consultant, serial entrepreneur, and founder of Premier Strategy Box and Mic Unplugged. Mick shares his incredible journey from a promise he made to his mother at age 10 to building and selling his insurance agency for $16 million by age 32. The conversation dives deep into lessons in leadership, time management, and how Mick is helping agency owners become better CEOs with his consulting firm. Mick also unveils what he’s building next: AI-powered learning systems and digital twins designed to elevate the next generation of insu...
2025-04-1844 minInsurtechs.ioBuilding AI-Powered Claims Solutions: A Deep Dive with Timon GreggIn this episode of Founders Journey, host Jeff Shi sits down with Timon Gregg, co-founder of a cutting-edge claims technology company. Timon shares his journey from Oxford to launching an AI-driven third-party administrator (TPA) in the U.S., tackling inefficiencies in the insurance claims process. He breaks down how AI-powered automation is transforming claims management—from fraud detection to digital FNOL—and why he and his co-founder relocated to Silicon Valley. Timon also discusses the company’s rapid growth, investment backing, and future plans, including scaling their AI claims solutions and acquiring TPAs. Tune in to hear how AI is res...
2025-04-1617 minInsurtechs.ioInnovating Insurance Brokerage: Michael Malfa on the Growth & Future of BoardWalk InsuranceWelcome to another insightful episode of Founders Journey! In this episode, Jeff sits down with Michael Malfa, the co-founder of BoardWalk Insurance, a leading Canadian property and casualty brokerage specializing in commercial P&C. Michael takes us through his journey into the insurance industry and how he co-founded BoardWalk with a vision to bring innovation and efficiency to the traditional brokerage model.Throughout the conversation, Michael highlights the unique challenges facing insurance brokers today and how BoardWalk is addressing these issues by leveraging technology. He shares the story behind their proprietary agency management system...
2025-04-1432 minInsurtechs.ioCrypto Meets Life Insurance: Building the First Bitcoin-Based Carrier with Zachary TownsendIn this episode, Jeff sits down with Zachary Townsend, co-founder and CEO of Meanwhile, the world’s first bitcoin-denominated life insurance company. Zach walks us through his journey from working in government and fintech to building a YC-backed startup acquired by Silicon Valley Bank, and now pioneering in insurtech. He dives deep into the origin of Meanwhile, how a late-night “aha” moment turned into a seed round led by Sam Altman, and how Bitcoin is reshaping life insurance as we know it. Zach also shares how Meanwhile is built to serve a global, decentralized economy and what it means to off...
2025-04-1143 minInsurtechs.ioBridging Finance and Technology: A Fintech Vision for Insurance with Timothy LiIn this episode, host Jeff Shi sits down with fintech innovator Timothy Li to explore the evolving intersection of financial services and insurance. With a background spanning consumer lending, banking, and tech startups, Timothy brings a deep understanding of how fintech infrastructure can revolutionize traditional insurance operations. The discussion delves into Timothy’s entrepreneurial journey, lessons from launching and scaling multiple ventures, and the critical role of infrastructure and compliance in both fintech and insurtech. Timothy also highlights how adapting successful fintech frameworks can drive innovation in the insurance space, offering insights into automation, underwriting, and distribution strategies for fu...
2025-04-0938 minInsurtechs.ioGrowing Insurance Trends and Legal Challenges With Lauren Ybarra’s ExpertiseWelcome to this insightful episode of Founders Journey! Today, Jeff is joined by Lauren Ybarra, an accomplished legal expert specializing in insurance law. Lauren takes us through her career, from her early ambition to become a judge to her eventual transition into the complex world of insurance law. She shares her work experiences with major companies like Zepco reels, Charbroil grills, and Sagicore Life Insurance Company, illustrating the breadth of her expertise.During the conversation, Lauren provides key advice for startups, focusing on the importance of strategic compliance and understanding state jurisdictions in insurance...
2025-04-0725 minInsurtechs.ioAI-Powered Sales in P&C Insurance: Scaling Mav AI with Matthew BlackIn this episode of Founders Journey, Jeff sits down with Matthew Black, founder of Mav AI, to explore how AI is revolutionizing sales and lead management in the P&C insurance space. Matthew shares his journey from a tech-obsessed teenager to building cutting-edge AI solutions for agencies and brokers. They discuss the evolution of AI from chatbots to LLMs, the challenges of scaling insurance sales, and why SMS remains the highest-performing channel for engagement. Matthew also dives into how Mav AI helps agencies break through growth ceilings, optimize lead handling, and leverage AI-powered automation for better efficiency. This conversation...
2025-04-0445 minInsurtechs.ioFrom Marketing to Ethical Hacking: Josh Crumbaugh’s Cybersecurity JourneyWelcome to another insightful episode of Founders Journey! In today’s episode, Jeff interviews Josh Crumbaugh, an influential figure in the ethical hacking world and the founder of PhishFirewall. Josh shares his inspiring transition from a marketing career to becoming a leader in cybersecurity, recounting how his passion for ethical hacking developed and eventually led to collaborating with top red teams and Fortune 500 companies.Throughout the conversation, Josh explains the human elements of cybersecurity that motivated him to establish PhishFirewall, a company focused on training individuals against cyber attacks using behavioral science. He also di...
2025-04-0253 minInsurtechs.ioRevolutionizing Property Insurance Claims with Elnor RozenrotIn this episode of Founder Journey, host Jeff Shi sits down with Elnor Rozenrot, a seasoned entrepreneur with deep experience in corporate leadership and venture capital. Elnor shares his unconventional path to entrepreneurship, driven by his passion for innovation and disruption. He reflects on his time leading innovation at LG Electronics and his venture capital work focused on transformative technologies.Elnor introduces his latest venture, Claimsetter, which aims to revolutionize the property insurance claims process. Inspired by a friend's difficult claim experience, Claimsetter streamlines the entire process—from pre-claim engagement to contractor coordination and pa...
2025-03-3130 minInsurtechs.ioRevolutionizing Insurance Ratings: A Deep Dive with Joseph PetrelliWelcome to another insightful episode of Founders Journey, where host Jeff is joined by Joseph Petrelli, the founder and CEO of DemoTech. In this engaging conversation, Joseph reflects on his remarkable career in the insurance industry, starting in 1969, and how a Reader's Digest book ignited his passion for actuarial science. From his early days at the Insurance Rating Bureau to his leadership role at Nationwide Insurance, Joseph's journey is one of perseverance and innovation.The discussion highlights the founding of DemoTech in 1985, an independent rating agency that has redefined rating processes for regional specialty...
2025-03-2836 minInsurtechs.ioTransforming Financial Advisory with AI Innovations by Sam RobinsonWelcome to this episode of Industry Voice with Jeff! Today, Jeff is joined by Sam Robinson, co-founder of an innovative financial advisory company that’s transforming the industry through AI. Sam’s journey into financial services began after a deeply personal experience—the cancellation of his father’s insurance policy in 2015—motivating him to step into the world of financial advising and entrepreneurship.In this insightful conversation, Sam shares how his time at Edward Jones and Northwestern Mutual prepared him for co-founding a business that leverages AI to streamline and optimize financial advisory practices. His compan...
2025-03-2632 minInsurtechs.ioJourney of Building a Cutting-Edge insurtech Platform with David WatsonWelcome to this episode of Founders Journey! Join us as David Watson shares his inspiring entrepreneurial path in the world of insurtech. David recounts his journey from working at Chick-fil-A to founding Blue Lake Insurance and developing the innovative platform Risk Advisor. His story illustrates the dedication and vision required to succeed in the insurance industry.David dives into the challenges of building Risk Advisor, which aims to streamline insurance processes through automation and data optimization for agents. He shares valuable insights on raising funds, collaborating with co-founders, and creating a user-friendly interface for...
2025-03-2433 minInsurtechs.ioThe Founder’s Journey: AI, Fraud Prevention, and Insurance with Sunil MadhuWelcome to another exciting episode of Founders Journey! In this episode, host Jeff sits down with Sunil Madhu, a seasoned entrepreneur and founder of six successful companies, including the $5 billion giant, Socure. Sunil shares his incredible journey from systems architect to startup founder, with a focus on IT risk and security, and how these experiences shaped his entrepreneurial path.Sunil delves into his latest venture, Instant, which harnesses the power of AI to provide businesses with fraud loss insurance. He offers valuable insights into the challenges of building this innovative solution, gaining backing from...
2025-03-2138 minInsurtechs.ioThe Evolution of Bamboo Insurance in the Industry with Taylor MobleyWelcome to this episode of Founder's Journey! Join us as Taylor Mobley, the CFO of Bamboo Insurance, shares insights into the company's innovative strategies and evolution in the insurance market since 2020. With a rich background in public accounting and experience at Ernst Young and Kemper, Mobley discusses how Bamboo prioritizes technology and omni-channel distribution to achieve capital efficiency.In this episode, Mobley dives into the challenges Bamboo faced entering the California market and their plans for expansion into Texas. He emphasizes the importance of leveraging proprietary technology for risk assessment, particularly regarding hailstorms, and...
2025-03-1931 minInsurtechs.ioBuilding Benekiva and the Future of Insurance Solutions with Bobbie ShrivastavIn this episode of Founder's Journey, Bobbie Shrivastav shares her remarkable transition from technologist to a prominent founder in the insurtech space. Starting in 2015 with her first startup, Doxmore, Bobbie was inspired to digitize documents after experiencing the inefficiencies of paperwork during her maternity leave. Her journey led to the creation of Benekiva, a revolutionary claims solution platform for life insurance and annuities, born from a pivotal partnership with a financial advisor.Bobbie discusses the hurdles faced while building Benekiva, the importance of strategic investments, and how listening to customers has been key to...
2025-03-1738 minInsurtechs.ioHow Oak Street Funding Drives Insurance Success with Scott StarsWelcome to another insightful episode of Insurance VC, PE, and M&A with Jeff, where we delve into the complexities of insurance lending with Scott Stars, a key figure at Oak Street Funding. Scott discusses his transition from a successful career at HSBC to his current leadership role in the specialized world of insurance loans. This episode offers valuable insights into Oak Street’s unique approach to financing and their focus on supporting the growth of captive agencies, aggregators, and independent insurance models.Scott sheds light on Oak Street’s loan products, from working capital to acquisitions, and explains the...
2025-03-1427 minInsurtechs.ioUnderstanding Insurance Deal Complexity and Ecosystems with Grant GriffinWelcome to another insightful episode of Insurance VC, PE, and M&A. Today, host Jeff sits down with Grant Griffin, Vice President of Investment Banking at Sherman Company, to delve into his transition from retail insurance to leading M&A efforts in the insurance sector. Grant shares his expertise in navigating the intricacies of insurance mergers and acquisitions, offering listeners a behind-the-scenes look at the complex and varied deal-making process.In this episode, Grant discusses the vital role that understanding the insurance ecosystem plays in successful M&A transactions, as well as the influence of macroeconomic factors like interest...
2025-03-1246 minInsurtechs.ioBuilding Insurtech Communities & Investing in Innovation with Tony LewIn this episode of Founders Journey, host Jeff Shi sits down with Tony Lew, co-founder of insurtech New York, to discuss his journey from software engineering to building one of the most influential insurtech communities. Tony shares how he and his partner David Gritz started insurtech New York, their challenges in pivoting through the COVID-19 pandemic, and their success in fostering industry connections. The conversation also dives into insurtech New York’s venture arm, their investment strategy, and the trends shaping the future of insurtech. If you’re interested in how insurtech startups can scale, attract funding, and build stro...
2025-03-1035 minInsurtechs.ioLessons in Persistence from Wade Millward’s Insurance Franchise SuccessWelcome to this exciting episode of Founders Journey, where host Jeff interviews Wade Millward, a pioneering entrepreneur in the insurance industry. Wade recounts how he and Jeff first connected at an insurtech event in New Mexico three years ago, bonding over their shared passion for innovation. Wade's story starts as a third-generation insurance professional, navigating early struggles before finding his true calling in entrepreneurship.Wade dives deep into his journey of founding a unique insurance franchise concept. He shares the highs and lows of building software, managing investor relationships, and how persistence fueled his success. Wade emphasizes the importance...
2025-03-0746 minInsurtechs.ioITC Vegas Reflection: Building Talent Pipelines with Laurissa BerkIn this episode of Post-ITC Reflection, we sit down with Laurissa Berk, Director of Global and Experiential Education at the University of Connecticut. Laurissa shares insights into how UConn is bridging the gap between academia and industry, particularly within the insurtech space. She discusses the university’s approach to fostering talent pipelines, the significance of ITC Vegas for students, and the importance of industry events in shaping future careers. Laurissa also highlights UConn’s competitive selection process for student participation and how these experiences are helping students secure real job opportunities. Tune in to hear how the next generation is m...
2025-03-0611 minInsurtechs.ioBuilding a Life Saving Device and a CRM Empire with Beau BrattonWelcome to this episode of Founders Journey, where Jeff dives into an inspiring conversation with Beau Bratton, a pioneering entrepreneur in CRM solutions. From his Santa Barbara roots to building a game-changing CRM tool in the insurance industry, Beau’s journey is one of resilience, innovation, and adaptability. He shares how his early telemarketing roles paved the way for Speed to Contact, later known as Ricochet 360, and the hurdles he overcame, including intellectual property challenges, to expand into diverse sectors like solar and mortgage.As they discuss Ricochet 360’s future, Beau highlights AI advancements, a new mobile app, and his...
2025-03-0536 minInsurtechs.ioITC Vegas Reflection: Event Takeaways & Industry Trends with Jon SpaugyIn this episode of Post-ITC Reflection, we sit down with Jon Spaugy to unpack his experience at ITC Vegas. Jon, a seasoned industry professional and event organizer, shares his first-time experience attending the conference as a registered participant. He reflects on the sheer scale of the event, key takeaways on networking, and how ITC fosters connections beyond just the convention floor. Jon also discusses how his own event, Agent Brokers United, is evolving, and what lessons he’s taking from ITC to improve his own show. From innovative exhibitor booths to the growing presence of independent agents and insurtech cr...
2025-03-0420 minInsurtechs.ioBuilding a Global Insurance Recruiting Empire with Nick HoadleyIn this episode of Industry Voice, host Jeff welcomes Nick Hoadley, founder of Insurance Search and host of the Insurance Coffeehouse Podcast. Nick shares his journey from law to insurance broking, and how his experiences led him to build a successful executive search firm specializing in the insurance and Insurtech industries. He dives into the evolution of his podcast, which now boasts over 25,000 listeners, and discusses the key differences between the UK and US Insurtech landscapes. The conversation also explores the growing insurance markets in Bermuda and Cayman, the impact of talent migration, and the rising competition from emerging...
2025-03-0340 minInsurtechs.ioBehind the Scenes of Insurtech: Event Mastery & Community Building with Thien PalmerIn this episode of Industry Voice, host Jeff Shi sits down with the powerhouse behind some of the biggest events in Insurtech, Thien Palmer. Known for her ability to create high-impact experiences, T has been shaping the industry's conference landscape for years—often behind the scenes. From orchestrating the first offsite event at ITC to leading major activations for Insurtech Insights, she’s been the connecting thread behind countless industry gatherings. Thien shares her journey into the Insurtech space, how she built her two companies—Jet The Agency and T Palmer Agency—and her approach to curating events that aren’t j...
2025-02-2852 minInsurtechs.ioITC Vegas Reflection: Insights from Alexis Vaughn on Insurance, Insurtech, and Building LegacyIn this special episode of the Post-ITC Reflection series, Jeff Shi is joined by Alexis Vaughn for an engaging discussion about her journey in the insurance industry, her experiences at ITC Vegas, and the impact she's making through Offcourse Consulting. Alexis shares how she transitioned from being an insurance agent to a corporate broker, then into the InsurTech space, eventually founding Offcourse, which supports InsurTech startups, brokers, and carriers. She also dives into her work with Lloyd’s Lab, Insurtech Atlanta, and the UConn Fintech program, where she’s helping to bridge the talent gap and bring more diversity into...
2025-02-2742 minInsurtechs.ioITC Vegas Reflection: Insights from InsurTech’s Biggest Event with James BenhamIn this episode of Post ITC Reflection, host Jeff sits down with James Benham, CEO of JBKnowledge and Terra, to break down key takeaways from ITC Vegas. James, an entrepreneur, investor, pilot, and InsurTech thought leader, shares his perspectives on AI trends, the future of InsurTech, and the evolving venture capital landscape. He also discusses the importance of bootstrapping, the rise of pragmatic AI applications in claims processing, and the ongoing shift from InsurTech 2.0 to 3.0. With his wealth of experience as a podcast host and keynote speaker, James provides valuable insights on the conference’s biggest themes, networking strategies, an...
2025-02-2644 minInsurtechs.ioITC Vegas Reflection: Key Takeaways with Kyle GeoghanIn this episode of Post ITC Reflection, host Jeff Shi sits down with Kyle Geoghan to discuss the biggest trends and insights from ITC Vegas. Kyle, co-founder of Indem, shares his journey from growing up in a family insurance business to launching an InsurTech startup powered by generative AI. They dive into how AI is reshaping the industry, the shift in exhibitor conversations at ITC, and the growing role of brokers in InsurTech. Kyle also offers a thought-provoking take on the parallels between AI and the rise of the internet, as well as what the next few years may...
2025-02-2541 minInsurtechs.ioMastering Insurance Agency Growth & Leadership with Troy KorsgadenIn this episode of Industry Voice, host Jeff Shi welcomes the legendary Troy Korsgaden to discuss his extensive career in the insurance industry. Troy shares his journey from building one of the largest Farmers agencies in America to becoming a sought-after consultant and speaker. He reveals key strategies for scaling an insurance agency, building a high-performance team, and adapting to the evolving industry landscape. Troy also talks about his latest venture— 'Korsgaden Insights Magazine' —and how he's using it to provide valuable industry knowledge. This conversation is packed with insights on leadership, discipline, and the future of insurance. Don't miss...
2025-02-2434 minInsurtechs.ioThe Journey from Intern to Sales Academy Founder with Michael WeaverWelcome to another episode of Industry Voice with Jeff! Today, Jeff interviews Michael Weaver, founder of Weaver Sales Academy and a prominent figure in the insurance industry. Michael shares his journey from an internship at an insurance agency during college to launching his own scratch agency with his wife, which ultimately led to the creation of Weaver Sales Academy. Throughout the episode, Michael dives deep into the role of structured training in developing successful insurance producers and leaders. He discusses the impact of Weaver Sales Academy’s on-demand sales training, the importance of leadership development, and his vision for fu...
2025-02-2133 minInsurtechs.ioITC Vegas Reflection: Insights & Innovation with Bobbie ShrivastavIn this special episode of our post-ITC Vegas reflection series, host Jeff Shi sits down with InsurTech veteran Bobbie Shrivastav to break down the key moments, trends, and takeaways from ITC Vegas. Bobbie shares her thoughts on how ITC has evolved since 2018, the importance of industry connections over content, and the innovative ways companies are using technology in insurance. She also opens up about her next big move—launching her fourth company in the insurance space—and the lessons she's learned about smart capital and co-creation. From standout booths to industry shifts, this conversation is packed with valuable insights for...
2025-02-2041 minInsurtechs.ioITC Vegas Reflection: Key Takeaways from Insurtech Connect 2024 with Bryan FalchukIn this special ITC Vegas Reflection episode, host Jeff Shi sits down with Bryan Falchuk to unpack their experiences at Insurtech Connect 2024. They discuss the overwhelming presence of AI at the event, how companies are racing to integrate AI into insurance, and whether this technological shift is truly revolutionizing the industry or just the next step in automation. Bryan shares his thoughts on the importance of using AI beyond just efficiency gains and the need for meaningful innovation in underwriting and risk selection. The conversation also dives into ITC’s evolving structure, the challenges faced by startups, the role of...
2025-02-191h 12Insurtechs.ioITC Vegas Reflections: Behind the Scenes with Nicole PeckIn this episode of ITC Vegas Reflections, host Jeff Shi sits down with Nichole Peck, the mastermind behind ITC Vegas 2024, to discuss the incredible effort that goes into creating the world's largest insurance innovation event. Nicole shares insights on the event’s evolution, the strategic planning behind its success, and the exciting new segments introduced this year—including ITC LATAM, BrokerTech, and Life & Health Benefits. From the challenges of running a massive event to the importance of customer experience, Nicole offers a behind-the-scenes look at what it takes to pull off ITC Vegas. Jeff also shares his reflections on this...
2025-02-1842 minInsurtechs.ioBuilding an Insurance Legacy and Innovating the Industry with Jason CassIn this episode of Industry Voice with Jeff, host Jeff Shi sits down with Jason Cass, a leading voice in the insurance podcasting space, to explore his remarkable career journey. From his early days in window sales to becoming a successful insurance agency owner, Jason shares the pivotal moments, mentors, and experiences that shaped his path. He discusses the challenges of breaking into the insurance industry, the importance of strategic partnerships—particularly with Travis Etheridge—and the origins of the Agency Intelligence podcast network.Jason delves into his innovative marketing and technology strategies, highlighting how AI and robotic process auto...
2025-02-171h 05Insurtechs.ioHow Simply IOA is Modernizing Insurance Options with Jason ButtsWelcome to another engaging episode of Industry Voice with Jeff! Today, Jeff sits down with Jason Butts, President of SimplyIOA, to discuss his remarkable career in the insurance industry. From his upbringing in an insurance family to leading an independent agency, Jason shares how his journey has shaped his innovative approach to insurance and customer service.In this episode, Jason recounts his transition from Allstate to launching SimplyIOA, focusing on homeowners' insurance in Florida. He delves into the unique challenges of the industry, particularly with home and auto insurance products, and how his company leverages cutting-edge technology and data...
2025-02-1425 minInsurtechs.ioThe Impact of California Wildfires on Insurance Litigation with Matthew Monson & Joseph PetrelliIn this episode, host Jeff Shi is joined by two industry experts, Matthew Monson and Joe Petrelli, to discuss the ripple effects of the devastating California wildfires on the insurance industry. They dive into the challenges of claims litigation, the financial strain on insurance carriers, and the growing role of the California Fair Plan as insurers retreat from the market. The discussion also covers the rising costs of reinsurance, the impact of regulatory decisions on pricing, and what the future holds for both insurers and policyholders in high-risk states like California and Florida. With billions in losses, skyrocketing claims...
2025-02-131h 25Insurtechs.ioRevolutionizing Claims with AI: How Strala is Transforming the Insurance Industry with Timon GreggIn this episode of the Claims Adjusted podcast, host MJ Martinez sits down with Timon Gregg, co-founder and CEO of Strala, to discuss how AI is revolutionizing the claims process. Timon shares his journey from algorithmic energy trading and private equity to co-founding Strala, a company dedicated to enhancing the claims experience for adjusters, insurers, and claimants alike. They explore the challenges faced by claims adjusters, the burnout caused by repetitive tasks, and how AI-powered solutions like Strala’s AI TPA can significantly improve efficiency, reduce cycle times, and create a more seamless claims experience. Timon also provides insights in...
2025-02-1324 minInsurtechs.ioFuture-Proofing the Insurance Industry through AI and Strategy with Bryan FalchukWelcome to this episode of Industry Voice, where Jeff sits down with Bryan Falchuk, a prominent leader in the insurance industry whose career includes management consulting, key roles at Liberty Mutual, and experience in international markets like Singapore and Hong Kong.Bryan shares his journey from consultant to Chief Claims Officer, offering unique insights into cultural nuances in global insurance markets and the importance of adaptability. The conversation dives into his work as an author and podcast host, exploring challenges in the industry, the impact of AI on underwriting, and the complexities of implementing innovative solutions in insurance.The...
2025-02-121h 03Insurtechs.ioExploring Virtual Healthcare and Telemedicine Innovations with Brian Del SavioWelcome to this episode of Industry Voice, where Jeff sits down with Brian Del Savio, Vice President of Sales at New Benefits, to explore their pioneering approach to non-insured benefits. In this conversation, Brian shares insights into his career shift from Guardian Life to New Benefits and the company's commitment to reducing health and lifestyle expenses for Americans. They discuss key trends, including the rapid adoption of telemedicine and the need for staying current with evolving technologies.Brian highlights New Benefits' unique offerings, such as virtual healthcare, mental health support, fertility assistance, and zero-dollar prescriptions, underscoring the shift toward...
2025-02-1029 minInsurtechs.ioThe Role of Technology in Catastrophe Response and Claims with Alan DemersWelcome to another insightful episode of Industry Voice with Jeff! In this episode, Jeff is joined by Alan Demers, whose career in the insurance industry spans decades, from his early work at Aetna Property Casualty to serving as Vice President at Nationwide. Alan shares his deep knowledge and experience in catastrophe response, recounting significant events like Hurricane Bob and how the industry’s approach has evolved over time.
Throughout the conversation, Alan delves into his various leadership roles, including leading the national CAT team and navigating the complexities of claims, quality assurance, and corporate venture capital. He discusses the ma...
2025-02-0736 minInsurtechs.ioEpisode 01: Mental Health in Insurance and the Launch of Project 55 with Brendan CorrIn the debut episode of the "Claims Adjusted Podcast" under the InsurTechs.io umbrella, host MJ Martinez welcomes special guest Brendan Corr. Together, they explore the challenges of mental health in the insurance industry, particularly in claims, and discuss Brendan's inspiring journey from the golf industry to insurance and the launch of Project 55. This innovative platform focuses on breaking the stigma surrounding mental health, providing education, resources, and community support for individuals and organizations. Brendan shares how Project 55 aims to empower claims professionals with tools for better mental health outcomes while creating a supportive workplace culture. Don’t miss th...
2025-02-0641 minInsurtechs.ioFrom Baseball to Business: Victor Gonzalez on Building a Marketing Community for Insurance Agents
Welcome to another insightful episode of Industry Voice! Today, our host sits down with Victor Gonzalez, a former professional baseball player turned insurance expert and marketing entrepreneur. Victor shares his unique journey from the sports world to the insurance industry, where he has built a thriving career despite challenges along the way.
In this episode, Victor reflects on his 10-year experience in insurance, from working with giants like State Farm and Allstate to founding and selling his own agency. He also delves into his current entrepreneurial venture in the marketing space, focusing on helping insurance agents take control of...
2025-02-0517 minInsurtechs.ioStacey Brown: Building Communities and Innovating the Future of InsurTech
Welcome to another inspiring episode of Industry Voice with Jeff! In this conversation, Jeff is joined by Stacey Brown, a trailblazer in the InsurTech industry. Stacey takes us through his remarkable career journey, starting in retail management, transitioning into IT during the dot-com era, and ultimately finding his true calling in the insurance world. His experiences are rich with inspiration and provide unique insights into the ever-evolving InsurTech landscape.
Throughout the episode, Stacey dives into pivotal milestones that defined his path, from his tenure at Travelers Insurance to his transformative work at Excel. He also sheds light on the...
2025-01-3149 minInsurtechs.ioInsurance Litigation Frequency: KPMG Moves Into Legal with Matthew Monson & JosephIn the first episode of our new series, "Insurance Litigation Frequency," host Jeff Shi is joined by legal experts Matthew Monson and Joseph Petrelli to discuss KPMG's groundbreaking move into the legal space. Together, they explore the implications of this shift for the insurance and legal industries, analyze emerging trends, and provide expert insights into how firms can navigate these changes. Don't miss this engaging discussion on the intersection of insurance, litigation, and innovation.
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2025-01-281h 05Insurtechs.ioArlind Mucaj’s Journey from Wall Street to Building Insurtech HartfordIn this insightful episode of Industry Voice, host Jeff Shi sits down with Arlind Mucaj to explore his dynamic journey through the insurance and InsurTech sectors. A seasoned professional with over 16 years of experience, Arlind shares his story of falling into the insurance industry, transforming processes at major carriers like Travelers, The Hartford, and Hartford Steam Boiler, and his passion for leveraging technology to drive innovation.
Arlind also delves into his pivotal role at InsurTech Hartford, working alongside industry leaders to foster a community that bridges traditional insurance expertise with cutting-edge technological advancements. From navigating the early challenges of...
2025-01-2436 minInsurtechs.ioInnovating Auto Insurance: Inside Root’s Strategies with Jason ShapiroIn this episode of Industry Voice, host Jeff Shi sits down with Jason Shapiro from Root Insurance to explore how the company is transforming the auto insurance landscape. Jason shares his unique journey from automotive technology to managing revenue for Root's B2B distribution.
The conversation dives into Root's innovative strategies, from their partnerships with Carvana and Goosehead Insurance to their commitment to reducing friction for independent agents. Jason highlights how Root leverages telematics and user-focused technology to deliver affordable, equitable insurance options while adapting to market demands.
Tune in to hear insights on Root’s...
2025-01-1739 minInsurtechs.ioInsurtech Slopes: Redefining Networking for Founders and InvestorsJoin host, Jeff Shi as he sits down with David Gritz and Stacey Brown to dive into the world of Insurtech Slopes, an innovative event designed to break free from traditional networking molds. Discover the origins of this unique winter forum, which combines business collaboration with outdoor adventure, fostering deep connections among Insurtech founders and investors.
With insights into past events, including their impactful workshops and engaging discussions, the trio highlights how Insurtech Slopes creates memorable experiences that balance professional growth with personal enrichment.
Tune in to learn about the event's history, what's coming up...
2025-01-1518 minInsurtechs.io27 Years of Innovation in Performance Marketing: Insights from Joey LinerIn this episode of Industry Voice, Jeff Shi engages in a thought-provoking discussion with Joey Liner, a distinguished leader in the performance marketing industry. Joey reflects on his remarkable journey, beginning with his early career in call center services and later transitioning into media and lead generation. Drawing from his 27 years of experience, Joey shares invaluable lessons, industry insights, and advice for professionals looking to excel in performance marketing.
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2025-01-1035 minInsurtechs.ioThe Evolution of InsurTech and Building Community with David GritzIn this episode of Industry Voice, Jeff sits down with David Gritz, co-founder of InsurTech New York and a prominent leader in the InsurTech space. David shares his remarkable journey from working in tech to building a thriving community that bridges the gap between startups and investors in the insurance industry.
David recounts his introduction to InsurTech in 2015 during a business turnaround project that led to the creation and eventual sale of Zero, a workers’ compensation software company. From there, his involvement with the Silicon Valley insurance accelerator laid the foundation for the launch of InsurTech New York in 2019. To...
2025-01-0346 minInsurtechs.ioShaping the Future of Insurance: Insights from Bobbie ColliesWelcome to another episode of Industry Voice with Jeff! In this insightful conversation, Jeff is joined by Bobbie Collies, the Chief Insurance Officer at Coterie Insurance, to explore her impressive 21-year journey in the insurance industry. From her early days as a Commercial Lines Underwriter Trainee at Society Insurance in Wisconsin to leadership roles in Secura and regional mutual carriers, Bobbie shares valuable insights from her extensive career.
Bobbie highlights her transition to InsurTech and how Coterie is revolutionizing the insurance landscape. She discusses the vital role of technology, particularly APIs, in modernizing processes and driving innovation within the...
2024-12-2732 minInsurtechs.ioNicholas Ayers on Building Better Agency, M&A with GloveBox, and Driving GrowthWelcome to another episode of Founders Journey with Jeff! In this episode, Jeff chats with Nicholas Ayers about his incredible journey to founding Better Agency, shares insights into the M&A between GloveBox and Better Agency, and dives into Nicholas’ exciting plans for the future as the new Head of Growth at GloveBox. Whether you're a founder navigating your own path, interested in mergers and acquisitions, or simply curious about scaling innovation in InsurTech, this episode is packed with valuable insights and lessons learned.
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Thank you to our sponsor Traq AI!
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2024-12-211h 16Insurtechs.ioNavigating Insurance Industry Valuations and Transitions with Carey WallaceIn this episode of Industry Voice, host Jeff Shi welcomes Carey Wallace, a dynamic entrepreneur and founder of Agency Focus, who shares her incredible journey from a tech startup to a leader in insurance consulting. Dive deep into Carey’s insights on helping agencies prepare for valuation, develop exit strategies, and ensure seamless transitions for long-term success. Carey discusses how emotional readiness, financial preparation, and strategic business planning are key pillars for agency transitions. This episode is packed with practical advice for agency owners contemplating their next steps, whether planning internal successions, external sales, or growth strategies.
Ca...
2024-12-2044 minInsurtechs.ioGloveBox Acquires Better Agency: A Deep Dive into the Founder’s Journey with Ryan MathisenIn this episode of Founder's Journey, host Jeff Shi sits down with Ryan Mathisen, co-founder of GloveBox, to explore the strategic merger and acquisition between GloveBox and Better Agency. Ryan provides an inside look at the M&A process, sharing key details about how the partnership came together and the long-term vision driving the decision.
Ryan also reflects on his entrepreneurial path to founding GloveBox, offering valuable insights into the challenges and opportunities of building a successful InsurTech business. From the early days of starting the company to navigating the competitive InsurTech landscape, Ryan shares lessons learned and advice...
2024-12-1339 minInsurtechs.ioActuarial Science Meets InsurTech: Leadership, Data Challenges, and Social Media with Chelsea AdlerWelcome to another exciting episode of Industry Voice with Jeff! Today, Jeff dives deep into the world of actuarial science and InsurTech, featuring guest Chelsea Adler, a seasoned actuary and social media influencer. Chelsea shares her career evolution, from her early days working in her father's insurance office to becoming a leader in the InsurTech space.In this episode, Chelsea reflects on her transition from State Farm to Root Insurance, offering insights into the cultural shift she experienced moving from a traditional insurance giant to a fast-paced startup. She also addresses the complexities of actuarial work, particularly when dealing...
2024-12-1333 minInsurtechs.ioHow Daniel Seong Leveraged Social Media for Insurance SuccessIndustry Voice: How Daniel Seong Leveraged Social Media for Insurance Success
Welcome to today's episode of Industry Voice with Jeff! In this exciting conversation, Jeff sits down with Daniel Seong, a successful insurance agency owner and TikTok influencer, to explore his remarkable journey from humble beginnings to industry leadership. Get ready to be inspired as Daniel shares his personal story and the strategies behind his business growth.
Daniel recounts his path from an immigrant childhood and military service to overcoming financial struggles and thriving in the insurance world. He discusses how Yelp, Google reviews, and social media—especially TikTok—help...
2024-11-1640 minInsurtechs.ioTransforming Insurance with AI: Kyle Geoghan's Founder Journey at IndemnTransforming Insurance with AI: Kyle Geoghan's Founder Journey at Indemn
In this episode of Founders Journey, host Jeff Shi welcomes Kyle Geoghan from Indemn. Kyle discusses his path from growing up in an insurance family to co-founding his company. Key themes include the challenges faced by independent insurance agents, the transformative power of generative AI, and Kyle's development journey. He highlights their first product, wedding and event insurance, and dives into the broader applications of AI in insurance. The episode also touches on Kyle's experiences with fundraising, product market fit, and the importance of...
2024-11-0940 min