{"type":"rich","version":"1.0","provider_name":"Transistor","provider_url":"https://transistor.fm","author_name":"The Nathan Barry Show","title":"$300M+ Founder: What Nobody Tells You Before Selling Your Business | Ankur Nagpal | 146","html":"<iframe width=\"100%\" height=\"180\" frameborder=\"no\" scrolling=\"no\" seamless src=\"https://share.transistor.fm/e/440b7e13\"></iframe>","width":"100%","height":180,"duration":3763,"description":"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.\nI 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.\nAnkur also shares how founders can use the QSBS tax break to keep millions more from an exit.\nIf 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.\nTimestamps:\n00:00 Introduction\n01:37 Teachable's Story\n03:39 Why Ankur Sold Teachable\n04:47 Nathan's Approach to Building\n07:16 Building to Sell vs. Building to Keep\n08:34 Carry's Story\n09:30 Understanding QSBS Tax Benefits\n16:06 Being Bought vs. Having to Sell\n16:40 Why Raise Capital for Carry?\n18:25 Bootstrapping vs. VC\n22:54 Lessons for Second-Time Founders\n26:10 Ankur's Next Chapter: USVC\n28:36 Recruiting Great Talent\n32:24 Our Contrarian Beliefs\n34:50 Go-to-Market Strategies\n39:18 Ankur's AI Content Strategy\n46:25 Staying Focused\n48:58 Content Workflows\n59:16 Product Market Fit Evolution\n01:02:08 Closing Thoughts\nIf you enjoyed this episode, please like and subscribe, share it with your friends, and leave a review. I read every single one.\nLearn more about the podcast: https://nathanbarry.com/show\nFollow Nathan:\nInstagram: https://www.instagram.com/nathanbarry\nLinkedIn: https://www.linkedin.com/in/nathanbarry\nX: https://twitter.com/nathanbarry\nYouTube: https://www.youtube.com/@thenathanbarryshow\nWebsite: https://nathanbarry.com\nKit: https://kit.com\nFollow Ankur:\nX:...","thumbnail_url":"https://img.transistorcdn.com/94Z7X6faUKE41kiKTRfZPH0m-h9g7ytYNEt5v0i7EJE/rs:fill:0:0:1/w:400/h:400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9kODMx/YjU2MDE1OGMwYTVj/YWE2MjUyOTkwNTVi/YmJkMy5qcGc.webp","thumbnail_width":300,"thumbnail_height":300}