In 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, a…

In 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 event…

In 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 …

In 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 pla…

In 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 d…

In 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 measure…

In 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 foun…

In 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.…

In 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…

In 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 convers…

In 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…

In 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 …

In 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…

In 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 in…

In 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 i…

In 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 t…

In 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 …

In 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, Kat…

In 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 Majesc…

In 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 tool…

In 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 …

In 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 a…

In 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 t…

In 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 diffe…

In 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 …

In 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 automatin…

In 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 …

In 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 tr…

In 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 …

In 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 …

In 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 t…

In 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…

In 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 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 fo…

In 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-found…

In 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 soft…

In 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 convers…

In 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…

In 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 transf…

Welcome 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 bri…

In 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…

In 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 discus…

Welcome 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 compa…

In 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 …

Welcome 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 develop…

In 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…

Welcome 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 a…

Welcome 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 ste…

Welcome 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 t…

Welcome 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 ex…