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

What does it take to turn a YouTube channel into a valuable, sellable business? That's what I wanted to explore with this week’s guest, Tyler Chou (aka The Creators' Attorney).

Having spent 20 years as an entertainment attorney at giants like Disney and BuzzFeed, Tyler now represents some of YouTube's biggest channels, helping them navigate exits and build sustainable enterprises.

In this episode, Tyler pulls back the curtain on the legal mistakes creators often make, the crucial steps to take to protect your assets, and why sometimes, a creator doesn't need to sell at all - they just need a sabbatical. Tyler shares insights on how to build a business that can eventually sell for 8 or 9 figures, and what investors are really looking for beyond just views.

Timestamps:

00:00 Introduction
01:09 Private equity looks to buy YouTube channels
03:52 Creator burnout
04:52 Protecting your IP and avoiding mistakes
08:20 Diversifying revenue beyond AdSense and brand deals
10:43 Avoiding misclassification lawsuits
12:46 The problem with reaction channels
17:45 Why buyers love recurring revenue and technical products
23:11 The power of artificial scarcity
28:20 How to make your brand less dependent on the creator
37:48 Should creators sell their business?
43:49 You might need a sabbatical, not an exit
45:00 How to protect yourself from predatory buyers
51:08 Hiring operators to run products
54:19 The power of angel investors on your cap table
56:29 The value of books for creators
1:11:08 Building a network of channels
1:14:10 Where to find Tyler

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 Tyler:
YouTube: https://www.youtube.com/@TheCreatorsAttorney
LinkedIn: https://www.linkedin.com/in/thecreatorsattorney
Instagram: https://www.instagram.com/thecreatorsattorney

Featured in this episode:
Kit: https://www.kit.com

Highlights:
01:38 - Why private equity is buying YouTube channels
07:50 - The power of building independent revenue streams
12:58 - Why reaction channels are worthless to buyers
38:00 - The surprising downsides of taking an exit
59:20 - The power of books for creator credibility

What does it actually take to sell a creator business? That’s what I wanted to get into with Pat Flynn and Liz Wilcox, who sat down with me to share some big news. After 18 years of building Smart Passive Income, Pat has officially sold the business - and Liz is the new owner.

In this episode, Pat and Liz take us through the entire process, from why Pat decided it was time to let go, to how they valued and structured the deal, why Liz was the right person to take over, and how they planned the transition to make sure the audience felt supported. We also get into what makes a creator business sellable, including building systems, community, recurring revenue, and a brand that can thrive beyond its founder.

If you're building a creator business and want to understand how to make it more valuable, transferable, and ultimately sellable, I think you'll get a lot out of this conversation.

Timestamps:
00:00 Introduction
01:15 Pat's big announcement
02:48 Liz's journey to acquiring SPI
04:30 How SPI became a sellable business
06:27 Pat's massive success with Pokemon
08:21 The impact of SPI's community
10:47 Why Pat let go of SPI
12:38 Prioritizing community over profit
14:10 The financial aspects of the deal
16:15 The future of Smart Passive Income: Team WIN
18:30 What makes a business sellable
20:00 Merging Liz's brand into SPI
21:23 10x is easier than 2x
22:50 The challenge of selling a personal brand
24:50 The intentional transition process

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 Pat:
X: https://twitter.com/PatFlynn
Website: https://patflynn.com
YouTube: https://www.youtube.com/@patflynn
LinkedIn: https://www.linkedin.com/in/patflynn

Follow Liz:
Website: https://www.lizwilcox.com
YouTube: https://www.youtube.com/@thelizwilcox
LinkedIn: https://www.linkedin.com/in/liz-wilcox-58740b1b0

Featured in this episode:
Kit: https://www.kit.com
Smart Passive Income: https://www.smartpassiveincome.com
Built to Sell: https://builtosell.com
Will It Fly?: https://patflynn.com/book/will-it-fly
The Virtual Campground: https://thevirtualcampground.com

Highlights:
01:15 - The big announcement
07:12 - Liz's personal mission for SPI
14:32 - The Pokémon channel's incredible growth
25:27 - The profound impact of communities
35:40 - Negotiating and structuring a business sale