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.

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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!