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

I recently sat down with Shawn Blanc, a creator I've known for years, to talk about what it takes to keep reinventing yourself and your business over a long career.

Shawn has spent the last 15 years building and evolving his business, from an ebook and sponsorships to his flagship Focus Course, masterminds, retreats, and eventually a completely new direction.

In this episode we discuss what Shawn calls “the burden of opportunity”, how to decide which opportunities are worth pursuing, and what happens when you realize the thing holding your business back might actually be you. Shawn also shares how he knew it was time to move on from the business that had built his career, and how that decision ultimately led to one of the biggest breakthroughs his business has ever had.

If you're building a creator business and thinking about what the next version of it should look like, you'll get a lot out of this conversation.

Timestamps:
01:13 Early Days: From Apple Blogger to Product Creator
04:35 First Product Launch
13:00 The "Bling Ding": $100K in a Week
20:37 The Burden of Opportunity: How to Say No
30:00 Business Stagnation
35:45 The Power of Community
45:40 The Pivot
51:00 The Big Breakthrough
55:10 Biggest Lessons

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

Follow Shawn:
Instagram: https://www.instagram.com/shawnblanc
LinkedIn: https://www.linkedin.com/in/shawnblanc
X: https://twitter.com/shawnblanc
Website: https://shawnblanc.net

Featured in this episode:
The Focus Course: https://special.thefocuscourse.com

Highlights:
20:37 The Burden of Opportunity: How to Say No
45:40 The Pivot
51:00 The Big Breakthrough

Are online courses really dead? I recently sat down with attorney-turned-entrepreneur Sam Vander Wielen to discuss her latest course launch that generated over half a million dollars in just four days.

In this episode, Sam shares the exact strategies she uses to consistently achieve massive success with her webinars and online courses, proving that these methods are far from "dead" in today's creator economy.

We also discuss the power of personalized customer interactions, Sam’s genius email list strategy that keeps her audience engaged and growing, and how she tackles the challenges of AI while maintaining an authentic and profitable brand.

If you have a course or are thinking of building one, you need to watch this entire episode.

Timestamps:
00:00 Introduction: Courses, Launches, & AI
01:20 Breaking Down a $500k Launch
02:49 Consistent Revenue Beyond Launches
04:48 Refilming with Kit Studios
06:17 Webinar Sign-ups & Email List Growth
14:00 The Weekly Lead Magnet Newsletter Strategy
20:30 The Unscalable Strategy: Personalized Videos
25:00 Unreasonable Hospitality & Handwritten Notes
31:00 The Impact of Podcasting on Business Growth
35:00 Order Bumps: Adding $100k to a Launch
36:00 AI and the Legal Industry
41:00 Financial Splurges: Cars & Property
44:00 Investing in Your Team

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 Sam:
Instagram: https://www.instagram.com/samvanderwielen
Website: https://www.samvanderwielen.com
Podcast: https://www.samvanderwielen.com/podcast
LinkedIn: https://www.linkedin.com/in/samvanderwielen

Featured in this episode:
Kit: https://www.kit.com
Typeform: https://www.typeform.com
Sam's book: https://www.samvanderwielen.com/book

Highlights:
01:20 Breaking Down a $500k Launch
14:00 Newsletter Strategy
20:30 The Power of Personalized Videos

What does it take to build a $1.5M business with only a 20,000-person email list and a YouTube channel? I sat down with Layla Pomper, the founder of ProcessDriven, who has done exactly that. Layla built her business to 150,000 YouTube subscribers teaching small business owners how to systemize their operations. What I found particularly insightful was her journey from services to courses, and back to a hybrid model that's now allowed her to triple her income. She shares what she's seeing many creators miss, her unique approach to sales calls, and the "one weird trick" that made all the difference in her business. If you have a course or are thinking of building one, you need to watch this entire episode.

Timestamps:
00:00 Introduction
01:16 Layla's revenue ceiling with courses
02:47 Layla's original course model
04:32 How Layla added services to break through the ceiling
06:45 Pricing model of Layla's services
08:15 Explanation of Layla's pricing structure
11:00 Layla's counterintuitive sales strategy
14:08 Key metrics Layla tracks in her business
17:13 Finding and fixing bottlenecks
20:44 The power of a small, engaged email list
23:19 Revenue per subscriber analysis
25:26 Simplifying complex business models
32:46 The best of products and services combined
40:15 Turning client questions into YouTube content
49:00 The value of customer conversations in services
57:24 The tailored productized service structure
1:01:36 Mistakes when adding services
1:03:07 The critical mistake of undercharging
1:04:09 Layla's lead generation strategy
1:07:08 YouTube content strategy and calls to action

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 Layla:
Website: https://www.processdriven.co
YouTube: https://www.youtube.com/@LaylaPomper
LinkedIn: https://www.linkedin.com/in/laylapomper

Featured in this episode:
Kit: https://www.kit.com
The Goal: https://www.goodreads.com/book/show/11128.The_Goal
Built to Sell: https://builtosell.com
SCORE: https://www.score.org

Highlights:
01:29 – Breaking through the infamous revenue ceiling
12:07 – The powerful impact of listening in sales
30:30 – The circularity of business growth
43:10 – Creating content by answering real questions
55:18 – Giving customers what they actually want