The Nathan Barry Show

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

When James Clear last spoke on the Craft & Commerce stage, Atomic Habits hadn't even been released. Now, it's sold over 30 million copies worldwide. I was delighted to welcome James back to the same stage 8 years later to unpack what he’s learned from creating one of the bestselling books of the last decade. In this conversation, James shares his insights on how to create a timeless product, how he built an email list of over 4 million subscribers, and the revolutionary publishing model he’s building with Authors Equity. James also answers burning questions from the audience on simplifying complex ideas, building lasting entrepreneurial friendships, protecting your identity as a creator in public, and James’s personal mission in life. If you’ve ever wondered what goes into creating a bestselling book, I think you’ll get a lot out of this episode. Timestamps: 00:00 Introduction 01:07 Expectations for Atomic Habits' success 02:54 Selling 30M+ copies 04:48 Timeless marketing principles 07:18 Positioning for long-term book sales 09:39 Building the world's largest single-author newsletter 12:44 Current effective growth tactics 14:01 Cross-pollinating platforms for growth 16:51 The vision behind Authors Equity 20:51 The Atomic Habits tipping point 23:09 Why books are an underrated business model 24:48 Simplifying complex ideas 27:54 Cultivating lasting entrepreneur friendships 31:33 Protecting your identity as a public creator 35:30 Why choose traditional publishing over self-publishing? 39:17 Mining for stories and metaphors 43:24 What makes Authors Equity different? 48:50 Daily habits for rebuilding momentum 51:50 James’s life mission 54:24 Authors Equity: working with self-published authors 58:05 James's parting thoughts: 10-year and 1-hour timeframes 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 James: Website: https://jamesclear.com Newsletter: https://jamesclear.com/3-2-1 X: https://twitter.com/jamesclear LinkedIn: https://www.linkedin.com/in/jamesclear Instagram: https://www.instagram.com/jamesclear Featured in this episode: Kit: https://www.kit.com Atomic Habits: https://jamesclear.com/atomic-habits Authors Equity: https://www.authorsequity.com Highlights: 02:10 - James's initial expectations for Atomic Habits 09:39 - How James built the world's largest single-author newsletter 23:09 - Why books are an underrated business model 48:50 - James’s daily habits for rebuilding momentum 51:50 - James’s life mission

Many creators dream of building an empire, but how many actually pull it off while still making time for family and personal passions? That's what I wanted to dig into with Ben Greenfield. He’s been podcasting since 2008 and has built a massive personal brand around health and wellness. But what really fascinated me is how he's leveraged that brand to launch not just one, but two other businesses that are scaling to entirely different levels: a supplements company and a revolutionary health tech platform. I sat down with Ben to break down his entire revenue pie, his strategies for growing multiple companies, and how he keeps his personal brand from becoming the bottleneck in his rapidly expanding empire. If you've built a creator business and are wondering what it would take to turn it into something much bigger, I think you'll get a lot from this episode. Timestamps: 00:00 Introduction 01:12 The early days of podcasting 03:00 Early revenue and online ventures 04:15 The lightbulb moment: Scaling IP online 05:59 Mapping out Ben Greenfield Life revenue 06:33 Audience and platform scale 07:31 Podcast revenue breakdown 09:18 Coaching and its growth potential 11:03 Life Network and Life Market 12:16 Total personal brand revenue breakdown 13:19 Integrated ad packages and whitelisting 16:09 Affiliate revenue and long-term partnerships 17:27 Team structure for Ben Greenfield Life 20:29 Lessons for scaling content businesses 22:45 Lifestyle design and work-life balance 23:52 Launching Kion 28:44 Disentangling personal brand from Kion 31:32 Leveraging brand for launch, then scaling independently 35:44 The new venture 39:55 Life OS's rapid growth and scale 42:47 The power of recurring revenue models 44:31 Intentional scaling beyond personal brand 47:47 Building an empire vs. a lifestyle business 49:30 Ben's daily lifestyle and routine 52:16 Wrap-up and where to find Ben 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 Ben: YouTube: https://www.youtube.com/@bengreenfieldlife Instagram: https://www.instagram.com/bengreenfieldfitness LinkedIn: https://www.linkedin.com/in/bengreenfield Website: https://bengreenfieldlife.com Featured in this episode: Kit: https://www.kit.com Boundless: https://shopbengreenfieldlife.com/products/boundless-updated-revised Kion: https://getkion.com Highlights: 04:15 - The lightbulb moment: Scaling IP online 12:16 - Total personal brand revenue breakdown 20:29 - Lessons for scaling content businesses 31:29 - Don't let your brand be the bottleneck 47:47 - How to build both empire and lifestyle businesses