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 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 Series B. He explains why passion and execution are the top traits he looks for in founders, the importance of distribution strategies in insurance, and how technology adoption—from AI to blockchain—is reshaping the industry. Listeners will also hear insights on how dry powder in venture capital is pressuring funds to deploy capital, what East Coast versus West Coast funding dynamics look like in insurtech, and the future of emerging products in insurance. Whether you’re a founder seeking capital, an investor evaluating opportunities, or simply curious about the intersection of finance and insurtech innovation, this episode offers valuable perspective on where the industry is heading.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Jeffrey Fidelman :https://www.linkedin.com/in/jeffreyfidelman/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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 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 advanced strategies like trust stacking. This episode is a must-listen for startup founders, venture-backed entrepreneurs, and insuretech leaders looking to optimize their tax outcomes at exit.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Christopher A. Karachale :https://www.linkedin.com/in/christopher-karachale-093b1049/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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 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 into the macroeconomic landscape, evolving deal terms, and the rise of convertible notes and SAFEs in today’s uncertain venture environment. Whether you're an insurtech founder, a VC, or someone navigating startup law, this episode delivers valuable, SEO-optimized insights on how to structure your startup for long-term success.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Vikas Srinath :https://www.linkedin.com/in/vikas-srinath-64249416/----------------------------- Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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 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 the importance of data and operational efficiency. She opens up about the volatility of the post-COVID insurance landscape, why traditional marketing org structures are becoming obsolete, and how AI, machine learning, and better contract transparency are changing the game.Sarah also discusses how she’s using Fraction Method to advise marketing teams, cut technology waste, and guide firms through tech stack decisions—all with a passion for aligning ethics, business outcomes, and customer experience. Whether you’re a legacy carrier, B2B SaaS leader, or insurtech founder, this episode delivers actionable insights into modern marketing, martech strategy, and digital transformation.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Sarah Caputo :https://www.linkedin.com/in/sarahcaputo/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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 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 software platform focused on end-to-end servicing automation. He breaks down the challenges of raising capital as a first-time founder, assembling a founding team, and identifying the pain points in the insurtech ecosystem that AI can solve.Whether you're a founder, investor, or insurance professional, this episode delivers key insights into the intersection of artificial intelligence, user experience, and the operational backbone of modern insurtech solutions.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Nikhil Kansal :https://www.linkedin.com/in/nikansal/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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 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 and essential soft skills.The conversation covers GIS’s annual career fair, scholarship programs, professional development events like etiquette dinners and resume reviews, and why insurtechs should actively engage to shape the next generation of industry talent. Alyssa also gives a preview of the upcoming annual conference in Hartford, CT and shares actionable ways companies and professionals can get involved.Whether you’re a hiring manager, industry veteran, or a rising student in risk management, this episode is packed with insights on investing in the future of insurance and insurtech.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Alyssa Bouchard :https://www.linkedin.com/in/alyssabouchard/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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 leading marketing at legacy carriers, Erich shares the stark contrast between startup marketing and enterprise brand strategy. He unpacks how marketing has evolved from a central strategic function to one often undervalued in the executive suite—and why that’s a dangerous shift. The conversation explores how legacy insurers can modernize their storytelling, why CMOs are becoming fractional leaders, and the impact of generative AI on marketing teams and brand authenticity.Whether you're a founder building a go-to-market plan, a CMO at a traditional carrier, or an investor exploring the next big insurtech brand, this episode delivers clear, actionable insight on building lasting brand equity in insurance.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Erich de Oliveira :https://www.linkedin.com/in/erichd/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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 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 marketing” approach leverages AI to unlock 30–40% additional revenue by optimizing third-party traffic and cross-sell strategies. Whether you’re in insurtech, affiliate marketing, or SaaS, this episode is loaded with actionable wisdom and growth hacks from a true builder’s perspective.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Scott Shou :https://www.linkedin.com/in/scottshou/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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 changing landscape of insurance journalism, the importance of curiosity in newsrooms, and why property and casualty insurance is far from boring. He also dives into how storytelling in insurance is evolving, the impact of mental health awareness in industry coverage, and why the media is playing a larger role in how consumers and professionals understand risk, regulation, and innovation in the p&c sector. Whether you're in underwriting, claims, or just passionate about the insurtech space, this episode is packed with rich historical context, compelling stories, and real-world advice on careers, content, and curiosity.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Greg Crawford :https://www.linkedin.com/in/gcraw/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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-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. Moe also reflects on their product philosophy of providing "insanely easy" tools for agents, the cultural shift in insurtech adoption, and how integration and AI are shaping the future of insurance sales technology.Whether you’re an independent agent, startup founder, or someone fascinated by bootstrapped SaaS growth stories, this episode delivers valuable insight into building and scaling a tech solution inside a traditionally change-resistant industry.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Moe Latif :https://www.linkedin.com/in/mlatif/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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 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, the future of embedded payments, and the potential for deeper integration between CRMs and back-end accounting systems. If you're looking to understand how digital payments are reshaping the insurance value chain, this is the episode for you.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Greg Mallin :https://www.linkedin.com/in/greg-mallin-4a95134/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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 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 mistakes leaders make during transitions, the role of experimentation in innovation, and what Amazon can teach insurance about risk and reinvention. This is a can't-miss conversation for anyone passionate about the evolving insurance landscape.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Steve Anderson :https://www.linkedin.com/in/stevetn/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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 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 discusses U.S. innovation, AI regulation, and where he sees AI + robotics going next. If you're navigating the frontier of applied AI and want to build with reliability at scale, this conversation is a must-listen.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Kevin McGrath :https://www.linkedin.com/in/mcgrathk/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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 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 and the emerging 3.0 wave driven by AI innovation. The episode is packed with tactical advice on how to make your startup VC-ready, understanding lead versus follow investors, navigating board dynamics, and the realities of raising capital. If you’re a founder looking to understand the venture capital world or an operator curious about where insurtech is headed next, this conversation is a must-listen.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Dave Wechsler :https://www.linkedin.com/in/davewechsler/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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 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 insurtech collaboration, highlighting notable local players like Steadily, Hippo, Loop, Assurely, Romely, and more. Listeners will learn about their monthly events, the highly successful McGlinchey symposium, and their vision for 2025 — including more founder dinners, startup showcases, and expanded collaboration with industry stakeholders. This is a must-listen for anyone interested in the future of insurtech, grassroots innovation, and the power of community-driven ecosystems.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Andrew Correll :https://www.linkedin.com/in/andrew-r-correll/David Perez :https://www.linkedin.com/in/davidperezatx/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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, 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 about his foray into semi-pro soccer team ownership, the real ROI of sports investments, and his current mission: giving back to the industry through mentorship and board roles in various insurtech and AI startups.This episode is packed with authentic insights, entrepreneurial lessons, and inspiration for founders, investors, and insurance professionals looking to leave their mark on the industry. Whether you're curious about the evolution of insurtech, scaling agencies with AI, or writing your first book, this episode offers a wealth of takeaways.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Jeff Arnold :https://www.linkedin.com/in/rjefferyarnold/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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 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 also explores how AI is transforming valuations in the insurtech space, why board composition matters for IPO success, and what legal firms like Winston & Strawn look for when working with high-growth insurance companies.Whether you're a Series C founder preparing for the next big leap or an investor curious about market signals for 2025, this episode delivers critical insights on navigating capital markets in a rapidly evolving insurtech landscape.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Michael Blankenship :https://www.linkedin.com/in/mikeblankenship/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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 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 covers topics like owner dependence, growth strategy, poor sales management, and the impact of equity in modern M&A deals. They also address the reality of competing with PE-backed giants, navigating due diligence, and preparing for storms—both financial and literal—with special attention to the Florida insurance market. Whether you're two years from selling or two weeks into scaling, this episode is a masterclass in agency growth and transition strategy, featuring actionable advice and real-world war stories. If you're an insurance entrepreneur, this is one episode you can't afford to miss.Keywords: insurance agency M&A, selling an insurance agency, insurance agency valuation, insurtech mergers and acquisitions, independent agency exit planning, agency brokerage consultants, fractional CFO for insurance, insurance agency growth strategy, private equity insurance deals, insurtech market trends-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Mike Mensch :https://www.linkedin.com/in/michaelmensch/Colby Allen :https://www.linkedin.com/in/colbytallen/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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 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 practice, the philosophy behind designing optimized lead funnels via Facebook and social platforms, and why his community-driven approach is gaining traction. He also discusses what sets top-performing annuity advisors apart in 2024, how his team builds sustainable virtual businesses, and why ethical product recommendations matter more than ever.Whether you're an aspiring insurance agent, a seasoned annuity advisor, or a financial services leader exploring scalable growth strategies, this episode delivers unmatched value on building legacy, mastering annuity solutions, and optimizing the sales journey through real education and purpose.-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Tracy Lownsberry :https://www.linkedin.com/in/tracy-lownsberry/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!

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 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 equity partners, how to build creditworthiness, and creative capital structuring. This is a must-listen for insurance agency owners looking to scale, exit, or navigate complex financial decisions with clarity.Whether you're planning an acquisition, evaluating your agency’s valuation, or preparing for perpetuation, Kelly’s perspective offers critical guidance grounded in decades of real-world experience.Keywords: insurance M&A, agency lending, SBA 7A, insurance capital, insurtech, agency growth, exit strategy, equity financing, commercial insurance, agency valuation, private equity in insurance-----------------------------Thank you to our sponsors:Traq AI! To schedule a demo with Traq AI today -- https://calendly.com/traq/traq-ai-introduction-for-insuretechs-ioMavSign up today to claim your exclusive offer: https://hiremav.com/insurtechsWho said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!https://insurtechs-2.creator-spring.comFollow Insurtechs.io :https://www.linkedin.com/company/insurtechs/https://www.youtube.com/@insurtechshttps://x.com/Insurtechs_iohttps://www.instagram.com/insurtechs/https://www.facebook.com/Insurtechs/https://www.tiktok.com/@insurtechsListen to the Pod :Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYhPandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614Jeff Shi :https://www.linkedin.com/in/jeffshiva/Kelly Drouillard :https://www.linkedin.com/in/kelly-drouillard-ins/-----------------------------Disclaimer: Some of the links in this video description are affiliate links. This means that if you click on one of the links and make a purchase, we may receive a small commission at no additional cost to you. Your support helps us create more content, and we truly appreciate it! Thank you for watching!