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

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 Introduction01:37 Teachable's Story03:39 Why Ankur Sold Teachable04:47 Nathan's Approach to Building07:16 Building to Sell vs. Building to Keep08:34 Carry's Story09:30 Understanding QSBS Tax Benefits16:06 Being Bought vs. Having to Sell16:40 Why Raise Capital for Carry?18:25 Bootstrapping vs. VC22:54 Lessons for Second-Time Founders26:10 Ankur's Next Chapter: USVC28:36 Recruiting Great Talent32:24 Our Contrarian Beliefs34:50 Go-to-Market Strategies39:18 Ankur's AI Content Strategy46:25 Staying Focused48:58 Content Workflows59:16 Product Market Fit Evolution01:02:08 Closing ThoughtsIf 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/showFollow Nathan:Instagram: https://www.instagram.com/nathanbarryLinkedIn: https://www.linkedin.com/in/nathanbarryX: https://twitter.com/nathanbarryYouTube: https://www.youtube.com/@thenathanbarryshowWebsite: https://nathanbarry.comKit: https://kit.comFollow Ankur:X: https://twitter.com/ankurnagpalLinkedIn: https://www.linkedin.com/in/ankurnagpalInstagram: https://www.instagram.com/ankurnaFeatured in this episode:Teachable: https://teachable.comCarry: https://carry.comHighlights:03:00 The Perfect Exit?10:40 QSBS Tax Benefits For Founders18:30 Bootstrapped vs. VC: Which is Higher Status?23:20 Product Market Fit for Second-Time Founders32:20 Our Contrarian Beliefs