Insurtechs.io

In 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 crit...

In 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 a...

In 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 bli...

In 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 platf...

In 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 ev...

In 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...

In 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 l...

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, and product-market fit. From running high-volume lead gen experiments at Cogo Labs...

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 eventually landing in the insurtech world via P&C Specialist.

Greg shares the chan...

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 insurance onboarding process and built a solution that quickly spread by word-of-mout...

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 plagued by inefficiencies. Learn how Agave Pay is streamlining workflows, enabling digit...

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 drives transformative growth. From Jeff Bezos’ leadership principles to the adoption c...

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 measurement and confidence scoring, and reflects on how gen AI democratizes capability acros...

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 founders a transparent look into the venture capital mindset, including how funds dec...

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.

Andrew and David recount how they transitioned into leadership during the pa...

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 and exiting multiple tech and insurance ventures, including RightSure, Lender Bridge...

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 conversation, offering founders, executives, and investors practical guidance on pub...

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 invaluable for any agency owner thinking about growth, preparing for an exit, or und...

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 dives into building Annuity Giants Agents Academy, a subscription-based training mode...