Insurtechs.io

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, Katie Olson, to share how Melon Local turned a living...

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 Majesco's now top-ranked podcast to being one of the...

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 tools, and now leading lead generation and distributio...

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 distribution. The conversation dives into the comp...

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 and his unique perspective on raising capital, buil...

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 the company's evolution from its startup days to a...

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 differences between U.S. and Asia-Pacific markets, and...

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 world of engineering-led startups into surplus lin...

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 automating data ingestion to surfacing high-quality leads a...

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 purpose. He recounts the collapse of his multimill...

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 transition from teaching crypto at UPenn to serving...

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 through Launch’s unique assessment and action-plan...

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 employers and candidates. From his recent experien...

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 the insurance and insurtech ecosystem. The conversa...

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 shared conference room—and scaling to over 22 lic...

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 the London insurance market, and offers an ins...

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 founding Vantage Insurance Partners. But what truly...

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-founding Buddy to make insurance more accessible throug...

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 software engineering to business leadership, the genes...

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 conversation explores the evolution of analytics in insur...

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 leadership, time management, and how Mick is help...

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 transforming claims management—from fraud detection to d...

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 bring innovation and efficiency to the traditiona...

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 of Meanwhile, how a late-night “aha” moment turne...

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 discussion delves into Timothy’s entrepreneurial journey...