$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 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