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-io

Mav

Sign up today to claim your exclusive offer: https://hiremav.com/insurtechs

Who said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!

https://insurtechs-2.creator-spring.com

Follow Insurtechs.io :

https://www.linkedin.com/company/insurtechs/

https://www.youtube.com/@insurtechs

https://x.com/Insurtechs_io

https://www.instagram.com/insurtechs/

https://www.facebook.com/Insurtechs/

https://www.tiktok.com/@insurtechs

Listen to the Pod :

Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982

Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYh

Pandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614

Jeff 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-io

Mav

Sign up today to claim your exclusive offer: https://hiremav.com/insurtechs

Who said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!

https://insurtechs-2.creator-spring.com

Follow Insurtechs.io :

https://www.linkedin.com/company/insurtechs/

https://www.youtube.com/@insurtechs

https://x.com/Insurtechs_io

https://www.instagram.com/insurtechs/

https://www.facebook.com/Insurtechs/

https://www.tiktok.com/@insurtechs

Listen to the Pod :

Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982

Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYh

Pandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614

Jeff 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-io

Mav

Sign up today to claim your exclusive offer: https://hiremav.com/insurtechs

Who said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!

https://insurtechs-2.creator-spring.com

Follow Insurtechs.io :

https://www.linkedin.com/company/insurtechs/

https://www.youtube.com/@insurtechs

https://x.com/Insurtechs_io

https://www.instagram.com/insurtechs/

https://www.facebook.com/Insurtechs/

https://www.tiktok.com/@insurtechs

Listen to the Pod :

Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982

Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYh

Pandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614

Jeff 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-io

Mav

Sign up today to claim your exclusive offer: https://hiremav.com/insurtechs

Who said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!

https://insurtechs-2.creator-spring.com

Follow Insurtechs.io :

https://www.linkedin.com/company/insurtechs/

https://www.youtube.com/@insurtechs

https://x.com/Insurtechs_io

https://www.instagram.com/insurtechs/

https://www.facebook.com/Insurtechs/

https://www.tiktok.com/@insurtechs

Listen to the Pod :

Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982

Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYh

Pandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614

Jeff 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-io

Mav

Sign up today to claim your exclusive offer: https://hiremav.com/insurtechs

Who said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!

https://insurtechs-2.creator-spring.com

Follow Insurtechs.io :

https://www.linkedin.com/company/insurtechs/

https://www.youtube.com/@insurtechs

https://x.com/Insurtechs_io

https://www.instagram.com/insurtechs/

https://www.facebook.com/Insurtechs/

https://www.tiktok.com/@insurtechs

Listen to the Pod :

Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982

Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYh

Pandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614

Jeff 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-io

Mav

Sign up today to claim your exclusive offer: https://hiremav.com/insurtechs

Who said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!

https://insurtechs-2.creator-spring.com

Follow Insurtechs.io :

https://www.linkedin.com/company/insurtechs/

https://www.youtube.com/@insurtechs

https://x.com/Insurtechs_io

https://www.instagram.com/insurtechs/

https://www.facebook.com/Insurtechs/

https://www.tiktok.com/@insurtechs

Listen to the Pod :

Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982

Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYh

Pandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614

Jeff 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-io

Mav

Sign up today to claim your exclusive offer: https://hiremav.com/insurtechs

Who said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!

https://insurtechs-2.creator-spring.com

Follow Insurtechs.io :

https://www.linkedin.com/company/insurtechs/

https://www.youtube.com/@insurtechs

https://x.com/Insurtechs_io

https://www.instagram.com/insurtechs/

https://www.facebook.com/Insurtechs/

https://www.tiktok.com/@insurtechs

Listen to the Pod :

Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982

Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYh

Pandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614

Jeff 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-io

Mav

Sign up today to claim your exclusive offer: https://hiremav.com/insurtechs

Who said insurance isn’t sexy? Prove ‘em wrong – grab your merch today!

https://insurtechs-2.creator-spring.com

Follow Insurtechs.io :

https://www.linkedin.com/company/insurtechs/

https://www.youtube.com/@insurtechs

https://x.com/Insurtechs_io

https://www.instagram.com/insurtechs/

https://www.facebook.com/Insurtechs/

https://www.tiktok.com/@insurtechs

Listen to the Pod :

Apple Podcast - https://podcasts.apple.com/us/podcast/insurtechs-io/id1775588982

Spotify - https://open.spotify.com/show/2jAGcKCT2v6rdWea3nvrYh

Pandora - https://www.pandora.com/podcast/insurtechsio/PC:1001094614

Jeff 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!