Search a title or topic

Over 20 million podcasts, powered by 

Player FM logo
Artwork

Content provided by Insurtechs.io. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Insurtechs.io or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.
Player FM - Podcast App
Go offline with the Player FM app!

Unlocking QSBS for Startup Founders with Christopher Karachale

36:17
 
Share
 

Manage episode 508222112 series 3606786
Content provided by Insurtechs.io. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Insurtechs.io or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

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!

  continue reading

106 episodes

Artwork
iconShare
 
Manage episode 508222112 series 3606786
Content provided by Insurtechs.io. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Insurtechs.io or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

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!

  continue reading

106 episodes

All episodes

×
 
Loading …

Welcome to Player FM!

Player FM is scanning the web for high-quality podcasts for you to enjoy right now. It's the best podcast app and works on Android, iPhone, and the web. Signup to sync subscriptions across devices.

 

Copyright 2025 | Privacy Policy | Terms of Service | | Copyright
Listen to this show while you explore
Play