Should you sell your business, or build it to own forever? Ankur Nagpal sold Teachable for $250 million and Carry for $76 million. I bootstrapped Kit and turned down a $200 million acquisition offer from Spotify. We took very different paths as founders.

I sat down with Ankur to break down why we made those choices and how they've played out. We get into the key considerations for selling a company vs. building it to own forever, why raising venture capital can quietly trap founders into a specific kind of business, and the hiring and go-to-market tactics Ankur used to build two companies from scratch.

Ankur also shares how founders can use the QSBS tax break to keep millions more from an exit.

If you've ever thought about selling your business, or you're trying to decide whether to bootstrap or raise venture capital, this is the episode to listen to before you make that call.

Timestamps:
00:00 Introduction
01:37 Teachable's Story
03:39 Why Ankur Sold Teachable
04:47 Nathan's Approach to Building
07:16 Building to Sell vs. Building to Keep
08:34 Carry's Story
09:30 Understanding QSBS Tax Benefits
16:06 Being Bought vs. Having to Sell
16:40 Why Raise Capital for Carry?
18:25 Bootstrapping vs. VC
22:54 Lessons for Second-Time Founders
26:10 Ankur's Next Chapter: USVC
28:36 Recruiting Great Talent
32:24 Our Contrarian Beliefs
34:50 Go-to-Market Strategies
39:18 Ankur's AI Content Strategy
46:25 Staying Focused
48:58 Content Workflows
59:16 Product Market Fit Evolution
01:02:08 Closing Thoughts

If you enjoyed this episode, please like and subscribe, share it with your friends, and leave a review. I read every single one.

Learn more about the podcast: https://nathanbarry.com/show

Follow Nathan:
Instagram: https://www.instagram.com/nathanbarry
LinkedIn: https://www.linkedin.com/in/nathanbarry
X: https://twitter.com/nathanbarry
YouTube: https://www.youtube.com/@thenathanbarryshow
Website: https://nathanbarry.com
Kit: https://kit.com

Follow Ankur:
X: https://twitter.com/ankurnagpal
LinkedIn: https://www.linkedin.com/in/ankurnagpal
Instagram: https://www.instagram.com/ankurna

Featured in this episode:
Teachable: https://teachable.com
Carry: https://carry.com

Highlights:
03:00 The Perfect Exit?
10:40 QSBS Tax Benefits For Founders
18:30 Bootstrapped vs. VC: Which is Higher Status?
23:20 Product Market Fit for Second-Time Founders
32:20 Our Contrarian Beliefs

$300M+ Founder: What Nobody Tells You Before Selling Your Business | Ankur Nagpal | 146

The Nathan Barry Show

$300M+ Founder: What Nobody Tells You Before Selling Your Business | Ankur Nagpal | 146