Cover of The Nathan Barry Show

The Nathan Barry Show

The Nathan Barry Show

By: Nathan Barry
Listen for free

Season's Savings | 0.99 €/month for 3 months

5.99 €/month thereafter - terms apply. Cancel monthly.
Summary
 As the CEO of Kit, Nathan Barry has a front row seat to what’s working in the most successful creator businesses. On The Nathan Barry Show, he interviews top creators and dives into the inner workings of their businesses in his live coaching sessions. You get unique insight into how creator businesses work and what you can do to increase results in your own business. One of the things Nathan is passionate about is helping you create leverage. Creator Flywheels let you create many copies of yourself so you don’t get bogged down with the little things in your business. Flywheels will help you reach a place where you can focus on revenue instead of busywork. Tune in weekly for new episodes with ideas and tips for growing your business. You’ll hear discussions around building an audience, earning a living as a creator, and Nathan’s insights on scaling a software company to $100M. Learn how to get more results with less effort and: Grow faster over time. Work less hard over time. Make more money over time.© 2026 Nathan Barry Economics Leadership Management & Leadership Marketing & Sales
Episodes
  • How to Grow and Monetize a Newsletter in 2027 (Full Strategy) | Chenell Basilio | 153

    How to Grow and Monetize a Newsletter in 2027 (Full Strategy) | Chenell Basilio | 153
    5 Nov 2026
    As the founder of an email marketing platform, you’d think my newsletter would be dialed in. But it turns out there's a lot I could be doing better. I think that's true for most creators, who get so caught up in growth hacks that their list slowly dies out or hits a plateau they can't get past.Chenell Basilio reverse engineers how the biggest newsletters grow and took her own newsletter, Growth in Reverse, to 21,000 subscribers in just 10 months. In this episode, Chenell walks me through the 5 levers behind newsletter growth, including how to make your content insanely valuable, how to build momentum with tactics like quizzes, and the one lever she sees hardly anyone using. Then she applies all of it to my own newsletter, from the headline on my site to how I share podcast episodes, and it turns out I have some work to do.If you're trying to grow your newsletter and want a total masterclass in how to do it, this is the episode for you.Timestamps:00:00 Introduction01:37 Why growth tactics are only 1 of 5 levers02:03 How Chenell hit 21,000 subscribers in 10 months03:29 Why going deeper than everyone else stands out04:40 Lever 1: Insanely valuable content06:24 6 ways to make content insanely valuable08:34 Mario Gabriele's S-1 breakdowns10:11 Making readers the smartest person in the room12:40 Why you should get on calls with your readers13:28 Lever 2: Positioning13:55 How a food waste app became The ADHD Weasel16:05 Why positioning changes over time18:54 How to find readers to talk to20:28 How reader calls shaped Sam Vander Wielen's bundle21:19 Lever 3: Building momentum21:56 Why you should pick one platform22:15 Why quizzes are working so well26:21 The quiz that 9X'd The ADHD Weasel's growth27:16 How to get noticed by creators you admire28:46 Building a quiz for The Ladders of Wealth29:47 Lead magnets that don't need new content30:39 Using AI skills as lead magnets32:01 Why you should post more on social35:05 How to mine your best content38:34 Why it's okay to repeat your best stories39:43 Lever 4: Conversion41:55 Chenell's spicy take on Linktree43:35 How Dru Riley got a landing page to 40%45:55 Why the wrong views won't convert48:27 How Pat Walls positioned Starter Story's paid product50:54 Lever 5: The one hardly anyone is doing51:39 Why you need an "almost there" page53:24 What makes a great welcome email55:52 How to surprise new subscribers58:21 Doing what bigger creators can't1:02:12 Why you should subscribe to your own newsletter1:03:55 Chenell audits Nathan's newsletter1:06:38 The bar for Nathan's newsletter content1:09:20 Splitting the podcast into its own email1:11:36 Turning the book launch into content1:13:44 Chenell reads Nathan's homepage headline1:16:36 Sharing your success without bragging1:18:42 Promoting the newsletter inside episodes1:22:56 Fixing Nathan's conversion points1:26:14 The hidden cost of double opt-in1:29:49 How newsletters monetize1:31:46 Why Packy McCormick's sponsored deep dives work1:33:19 Group coaching and high-ticket offers1:36:00 The pricing sweet spot for memberships1:37:26 When paid newsletters work1:40:48 How to price a paid newsletter1:43:57 Final thoughtsIf 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/showFollow Nathan:Instagram: https://www.instagram.com/nathanbarryLinkedIn: https://www.linkedin.com/in/nathanbarryX: https://twitter.com/nathanbarryYouTube: https://www.youtube.com/@thenathanbarryshowWebsite: https://nathanbarry.comKit: https://kit.comFollow Chenell:Instagram: https://www.instagram.com/chenellcoX: https://x.com/chenellcoLinkedIn: https://www.linkedin.com/in/chenellcoYouTube: https://www.youtube.com/@growthinreverseWebsite: https://growthinreverse.comFeatured in this episode:Kit: https://www.kit.comGrowth In Reverse: https://growthinreverse.comNewsletter scorecard: https://growthinreverse.com/scorecardThe Generalist: https://www.generalist.comThe ADHD Weasel: https://adhdweasel.substack.comTrends.vc: https://trends.vcStarter Story: https://www.starterstory.comThe Ladders of Wealth: https://laddersofwealth.comHighlights:06:24 The 6 ways to make content insanely valuable26:37 The quiz that 9X'd The ADHD Weasel's daily growth50:54 The growth lever almost no one is using1:13:44 Chenell roasts Nathan's newsletter1:31:46 How Packy McCormick gets paid 5 to 10X for sponsored deep dives
    Show more Show less
    1 hr and 45 min
  • The Newsletter Is Dead. Here’s How To Survive AI Agents | Dan Shipper | 152

    The Newsletter Is Dead. Here’s How To Survive AI Agents | Dan Shipper | 152
    29 Oct 2026
    What happens to your newsletter when the first thing to read it isn't a person, but an AI agent? For anyone who has built a business on email, that shift is coming a lot faster than most of us expect.I sat down with Dan Shipper, co-founder and CEO of Every, a company that writes about AI, builds AI software, and gets to test the models before they're released. Dan has interviewed Sam Altman and is one of the people closest to the cutting edge that I know. We get into how good AI has become at using your computer, why Dan thinks the newsletter as we know it is dead, why OpenAI or Anthropic will likely build a new kind of inbox, and the one number his team is chasing right now that they might stop chasing soon. Dan also shares why, despite all the change, he's so optimistic about where this is going.If email sits at the heart of your business, I think you'll get a lot out of this conversation.Timestamps:00:00 Introduction01:22 The AI workflow every creator should set up02:43 How Dan writes by talking to his AI04:21 Why computer use is suddenly so good05:12 How an agent reordered Dan's 8,000-word story07:31 Turning an editor's taste into an AI skill09:44 How to build a skill without writing it yourself10:49 Using evals to make your skills better over time12:45 Should you go deep on one AI platform?15:29 Nathan's AI workflow for following up after events18:24 Why Dan is so optimistic about AI20:55 The three stages of adapting to new technology23:59 Ambition in the age of AI25:30 Why creators should stay diversified26:01 Building an app for your audience in a weekend27:08 Why every creator can now have a feed29:08 How Dan uses custom feeds to run Every31:06 Everyone can now work like Ryan Holiday32:08 Why AI curation hasn't caught up with creation32:51 Frontier alerts and writing for each reader34:29 Why Every is hiring more engineers than ever37:02 Why Dan says the newsletter is dead40:21 When your open rate drops to zero41:05 Seth Godin and being missed when you don't publish42:27 Why OpenAI and Claude will build a new inbox43:43 What actually replaces email?46:26 How Dan is positioning Every for what's next47:25 Why Every may stop chasing email signups48:35 Pushing content through MCP servers49:52 What creators should do to get ready51:59 Why quality matters more than ever54:00 What a high-quality audience has done for Dan55:21 Why Nathan is underusing his AI tools56:44 The Eight Levels of AI58:02 How Every makes money58:53 Splitting Every into frontier and product teams1:01:56 Pirates vs architects1:02:41 Kit's App Store and the cost of experiments1:03:54 How Every launches experiments it won't support1:06:04 Dan's hot take on AI and jobs1:07:23 What Andrew Carnegie's story teaches us1:08:07 What Dan is reading right now1:10:24 Where to start with Every1:11:05 Final thoughtsIf 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/showFollow Nathan:Instagram: https://www.instagram.com/nathanbarryLinkedIn: https://www.linkedin.com/in/nathanbarryX: https://twitter.com/nathanbarryYouTube: https://www.youtube.com/@thenathanbarryshowWebsite: https://nathanbarry.comKit: https://kit.comFollow Dan:X: https://x.com/danshipperLinkedIn: https://www.linkedin.com/in/danshipperWebsite: https://danshipper.comYouTube: https://www.youtube.com/@EveryInc/videosFeatured in this episode:Kit: https://www.kit.comEvery: https://every.toHow Codex Happened: https://every.to/p/how-codex-happenedThe Eight Levels of AI Adoption: https://every.to/guides/the-eight-levels-of-ai-adoptionAfter Automation: https://every.to/chain-of-thought/after-automationHighlights:02:43 Why Dan writes by talking out loud to his AI08:35 Turning 40,000 copy edits into a "Kate pass"21:17 The agency rupture everyone feels with AI37:29 Why the newsletter as we know it is dead47:25 The one number Every might stop chasing
    Show more Show less
    1 hr and 12 min
  • Why Community Beats Followers (And How to Build One) | Jayson Gaignard | 151

    Why Community Beats Followers (And How to Build One) | Jayson Gaignard | 151
    22 Oct 2026
    Do you want to know how to get into rooms with people who are several levels above you?Jayson Gaignard is the reason about 50 of my favorite entrepreneur friends are in my life. He’s the founder of Mastermind Talks, an invite-only community for entrepreneurs, and the author of Community Made, which breaks down exactly how to build those key relationships yourself.In this episode, Jayson shares how to find your people, invest in them, and ask for help. We get into how to host your own event when you can’t get an invite, the three ways to get access to people above your level, and why “How can I help?” is the wrong question to ask.If you want to build relationships with people you admire, this is the episode to watch.Timestamps:00:00 Introduction01:23 How Jayson connected Nathan to 50 entrepreneur friends02:15 Why Jayson wasn't always a super connector02:57 The loneliness that led to Mastermind Dinners04:14 Never beg for a seat when you can build your own table05:29 Why the host gets the most status in the room06:14 Lower-lift ways to bring people together06:49 How Summit Series started with a ski trip08:57 Start with the easiest yes09:28 The anchor tenant strategy10:27 Nathan's author mastermind with James Clear11:06 Partnering to host the room12:35 Organizing a team to play above your level13:21 Will Guidara's gratitude for being invited14:51 Buying access and the speed of relationships15:43 Money, moxie, and service15:58 Andrew Wilkinson's $57,000 lunch with Bill Ackman17:58 Moxie and the power of cold emails19:30 The man who stood up Mark Zuckerberg20:45 Nathan chickens out of meeting his heroes22:55 Eight seconds of courage24:02 Leaving energy vs. lingering energy24:47 Nathan's 45-second intro to Chris Brogan25:44 How a quick hello led to a call with Steven Bartlett27:06 Why you shouldn't put people on a pedestal27:53 Abundance vs. scarcity when meeting people29:47 Service and Ryan Holiday's apprenticeship31:20 Why Benjamin Graham told Warren Buffett he was overpriced31:58 Why "How can I help?" is the wrong question32:18 How Jayson built a relationship with Shep Gordon33:12 How to offer help that's actually specific36:00 The relationships that weigh you down38:55 Why all relationships go dormant naturally39:45 Why entrepreneurs and creators feel isolated41:17 Craft + Commerce as an annual pilgrimage42:35 Conferences vs. masterminds vs. communities46:00 Conversations that normally take years48:00 Do great work and your network will find you49:55 How great work raises your hit rate51:54 Why you're not ready for Diary of a CEO53:35 Putting in the reps on camera54:28 Ramit Sethi's advice on media training56:39 Increasing your surface area of luck59:38 Jayson's friends-only email updates1:02:06 The email that saved MMT in 20201:04:59 Who to include on your update list1:05:50 Nathan's missing annual review1:07:22 The 90-minute quarterly update1:08:17 A fan base vs. a community1:09:59 Curating like the bouncer at the club1:10:36 Kit's triads and MMT's MM3s1:15:00 People come for content, stay for community1:15:47 The ask, give, praise model1:18:26 How praise reinforces the value of the network1:21:02 Praise cards mailed 90 days later1:24:18 Why the book is called Community Made1:27:06 Final thoughtsIf 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/showFollow Nathan:Instagram: https://www.instagram.com/nathanbarryLinkedIn: https://www.linkedin.com/in/nathanbarryX: https://twitter.com/nathanbarryYouTube: https://www.youtube.com/@thenathanbarryshowWebsite: https://nathanbarry.comKit: https://kit.comFollow Jayson:Instagram: https://www.instagram.com/jaysongaignardX: https://x.com/jaysongaignardLinkedIn: https://www.linkedin.com/in/jaysongaignardWebsite: https://www.jaysongaignard.comFeatured in this episode:Kit: https://www.kit.comMMT: https://mmt.communityCommunity Made: https://communitymade.comHighlights:02:22 Jayson had two people at his bachelor party24:02 Leaving energy vs. lingering energy49:55 Why great work changes your hit rate on everything1:02:06 The friends-only email that saved MMT1:21:02 The praise cards Jayson mails out 90 days later
    Show more Show less
    1 hr and 28 min
adbl_web_anon_alc_button_suppression_t1
No reviews yet