Insurtechs.io

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 strategic acquisition by Vertafore, revealing hard-earned insights into timing the market, building valuable tech for a niche audience, and navigating a sale in a down market. Daniel also reflects on what founders often get wrong about exits, how M&A differs when strategic buyers are involved, and what he would do differently if he started again today. This episode is a must-listen for insurtech founders, operators, and investors who want a clear-eyed view of what it really takes to succeed and exit in today's market.

-----------------------------

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/

Daniel Metcalf :

https://www.linkedin.com/in/danielmetcalf/

-----------------------------

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 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 the broader implications of trust, distribution, and underwriting in modern insurance. Tony and Michael share their extensive industry perspectives—from the necessity of regulation to tech-driven disruption—and challenge listeners to think differently about how insurance can be more inclusive, accessible, and seamlessly integrated into everyday experiences. This episode is packed with insight for founders, investors, and incumbents navigating the future of 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/

Theresa Blissing :

https://www.linkedin.com/in/theresablissing/

Michael Waitze :

https://www.linkedin.com/in/michaelwaitze/

-----------------------------

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, 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 lines brokerage and eventually launched Rainbow—a software-enabled underwriting company focused on niche commercial markets like restaurants and wellness.

Bobby dives deep into the differences between building his first and second insurtech startup, the evolution of fundraising in today's market, and what makes a successful team in this space. He unpacks Rainbow’s underwriting-first model, their focus on agent partnerships, and how their internally-built technology platform enhances efficiency without sacrificing the human touch.

This conversation is packed with valuable insights on capital raising, product development, team-building, working with carriers, and scaling insurtech businesses sustainably. Whether you're a founder, investor, underwriter, or agent, Bobby’s tactical and honest reflections are 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-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/

Bobby Touran :

https://www.linkedin.com/in/bobby-touran-782a6513/

-----------------------------

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 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 and improving the underwriter experience, Steve and Mico break down the mechanics of deploying AI in real-world workflows. They also discuss how to think about ROI when evaluating insurtech vendors, the gap between carrier innovation goals and actual execution, and what the next evolution of insurance distribution might look like. This episode is packed with practical insights for carriers, MGAs, and tech partners navigating the 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-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 Reeves :

https://www.linkedin.com/in/sarah-gandy-reeves-49a70519b/

Matthew Sutika :

https://www.linkedin.com/in/matthewsutikanimbleins/

-----------------------------

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 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 as a crypto advisor at the SEC during pivotal cases like FTX and Terraform Labs. The trio explores practical use cases for blockchain in insurance, the emergence of stablecoins, challenges in underwriting crypto companies, the importance of custody and regulation, and the potential for MGA innovation and mutual models in a high-risk space. It's a thoughtful and in-depth look at how crypto is colliding with traditional insurance and where the real opportunities and threats lie.

-----------------------------

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/

Susan Holliday :

https://www.linkedin.com/in/susan-c-holliday/

David Crosbie :

https://www.linkedin.com/in/davidcrosbie/

-----------------------------

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 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 multimillion-dollar construction business, the humbling reality of working as a custodian, and how those trials forged the mindset that now fuels his mission to help others break through adversity. From NFL locker rooms to insurtech ITC Vegas stages, Marcus shares why building your personal brand, embracing failure, and being your own CEO is vital — especially for those entering a new chapter after a long career 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/

Marcus Ogden :

https://www.linkedin.com/in/marquesogden/

-----------------------------

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 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-planning tools, Caleb is on a mission to empower insurance sales teams with cutting-edge, easy-to-use technology. Learn how Launch helps producers identify niche markets, quantify risk, and guide clients beyond the premium, while increasing close rates and improving client alignment.

This conversation dives into the changing expectations of insureds, what producers are missing today, and how the future of sales enablement is unfolding in the insurtech world.

-----------------------------

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/

Caleb Cramer :

https://www.linkedin.com/in/caleb-cramer/

-----------------------------

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, 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 experience at the Connected Claims Conference to advice on fractional talent and navigating emerging markets, Ira unpacks key strategies for growing companies and professionals looking to make their next move.

This episode is a must-listen for hiring managers, founders, and professionals eager to understand the evolving landscape of insurtech recruitment.

-----------------------------

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/

Ira Ziff :

https://www.linkedin.com/in/iraziff/

-----------------------------

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, 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 conversation explores Josh’s early experience co-founding a robo-advisor platform in the 90s, his transition into executive search, and his leadership in launching initiatives like the Hartford InsurTech Hub and Imagine Incubator. Josh also discusses the patterns he’s seen across over 170 podcast interviews with startup founders, offering insight into what makes great leaders succeed, common blind spots, and the challenges international founders face in the U.S. market. This is a rich episode full of lessons from both sides of the insurtech table.

-----------------------------

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/

Josh Hollander :

https://www.linkedin.com/in/joshuarhollander/

-----------------------------

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, 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 licensed agents and nearly $15M in annualized premium.

Dan dives deep into the pivotal moments that shaped his business: the leap of faith into a high-rent office, the transformation brought on by marketing and automation, and the power of mentorship—both online and through mastermind dinners with industry peers. This episode is packed with insight on building momentum in a slow-starting insurance career, the value of systems and sales training, and why focusing on what you do best can be the most powerful strategy of all. If you're scaling an insurance agency or thinking about making the leap, this one's 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-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/

Dan Kitajima :

https://www.linkedin.com/in/dan-kitajima-493163a/

-----------------------------

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!