The Nathan Barry Show

The online business world is changing. People have more information than ever at their fingertips, and the business models that many creators started out selling aren't converting the way they used to.
I sat down with Jasmine Star to talk about why traditional courses and memberships are becoming harder to sell, and the new hybrid offer model she now teaches her clients. We get into how to build offers around specific customer results, how to find out what people will actually pay for before you build, and Jasmine’s four-step framework for building a consistent $10K/month business. She also shares how she delivers high-touch coaching at scale, and the best ways to build trust with your audience in today’s “trust recession”.
If you’re building an online business and wondering what types of offers still work in today’s crowded online space, I think you’ll get a lot out of this conversation.
Timestamps:
00:00 Intro
01:18 Jasmine’s first digital offer
04:00 How her $197 course made $255K
04:40 Why she built a membership
06:22 The problem with traditional memberships
08:28 Building Social Curator
10:27 The creator economy after 2020
12:07 Why courses and memberships stopped working
13:12 The hybrid offer
16:40 How to price an offer
20:02 Turning coaching into a scalable offer
22:27 Who the offer is for
24:28 The 90-day $10K offer
26:30 The $4K Freedom Formula
29:32 How to keep clients accountable
33:50 Why asynchronous coaching works
35:36 Scaling coaching to hundreds of clients
39:25 How to market the offer
44:01 Using webinars to sell
47:13 Why long-form content is coming back
50:04 Measuring content performance
52:43 How Jasmine met Nathan
53:41 How to get high-value clients
55:29 Creating an offer people will pay for
59:55 Finding the right audience
1:00:49 Getting your messaging right
1:04:26 Finding your customer's pain point
1:06:10 Using DMs to build trust
1:09:38 Building a personal brand
1:11:48 Final 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 Jasmine:
Instagram: https://www.instagram.com/jasminestar
Website: https://www.jasminestar.com
X: https://x.com/jasminestar
LinkedIn: https://linkedin.com/in/jasmine-star
YouTube: https://www.youtube.com/@officialjasminestar
Featured in this episode:
Kit: https://www.kit.com
Social Curator: https://www.socialcurator.com
Highlights:
03:38 How Jasmine made $255,000 in five days
12:07 Why courses are no longer enough
17:31 How to find what people will actually pay for
33:50 People already have the information
36:15 Why Jasmine’s ROI guarantee isn't a money-back guarantee

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