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The Nathan Barry Show

The Nathan Barry Show

By: Nathan Barry
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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 Marketing & Sales
Episodes
  • If I Wanted to 10x My Revenue in 2027, I’d Do This | Matt Trinetti | 154

    If I Wanted to 10x My Revenue in 2027, I’d Do This | Matt Trinetti | 154
    Nov 12 2026
    Growing a membership from $500,000 a year to $5 million comes down to five specific things. In this episode, I map them out on the board using Matt Trinetti’s membership as an example. Matt is the cofounder of London Writers’ Salon, where 1,000 writers gather every weekday to write together in silence. They’re on track for $750,000 this year, and Matt wants to grow from 2,000 members to 20,000.In this episode, I give him the exact blueprint for how to get there. Up on the board, we get into why mission and vision come before any growth tactic, how to track your funnel and conversion rate at every step, why retention is one of the biggest levers in a recurring revenue business, and how to package your products so people know exactly which plan is right for them. If you run a membership or any subscription business, I think you'll get a lot out of this conversation.Timestamps:00:00 Introduction01:37 London Writers' Salon by the numbers02:06 Three membership tiers and the Residency04:28 The goal of $5 million and 20,000 members05:42 Why a revenue goal felt uncomfortable for Matt06:30 Why profit is permission to do it again tomorrow07:19 The five keys to scaling a membership07:43 London Writers' Salon's mission08:59 Why creative health will become a category10:45 Turning your mission into a vision with numbers11:26 How Kit sets its mission and vision13:11 Why your vision has to be big enough for your team17:09 Why Kit tracks counterbalancing goals18:36 How Writers' Hour started in the pandemic21:36 Why you need to obsess over your funnel21:52 Why a membership is really a SaaS business23:07 Mapping the membership funnel25:18 Matt's 27% trial conversion rate27:05 Why all traffic is not created equal27:52 Why a 5,000-person event barely converts28:39 How Kit gets three more upgrades a day30:27 Upselling without making members feel sold to32:58 Why retention is everything33:23 User churn vs revenue churn34:46 Why cohorts change your churn numbers36:33 Why retention is the biggest lever you have38:06 What cancellation surveys miss38:37 Why every membership needs a pause option41:04 Getting on calls with members who cancel42:01 Should you add new products?44:22 Why every product decision goes through the funnel46:03 How renaming a plan "hobbyist" changed what people bought47:01 Why Silver and Gold don't tell people anything50:15 When to launch a separate product53:04 How adding more can lower perceived value53:55 The $499 annual accelerator idea55:51 Why you need to measure 30-day churn58:17 LTV to CAC, the number that tells you when to scale1:01:28 How every metric feeds into LTV to CAC1:04:01 How to calculate customer acquisition cost1:06:12 Matt's three big takeaways1:07:24 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 Matt:Instagram: https://www.instagram.com/mtrinettiLinkedIn: https://www.linkedin.com/in/matthew-trinettiNewsletter: https://seekingwithmatt.substack.comFeatured in this episode:Kit: https://www.kit.comLondon Writers' Salon: https://londonwriterssalon.comCircle: https://circle.soThe Ladders of Wealth: https://laddersofwealth.comHighlights:06:30 Profit is permission to do it again tomorrow27:52 The 5,000-person writing event that barely converts38:37 Why a pause button could save your members53:55 Why I'd sell a $499/year membership instead of $49/month58:17 The one number that tells you when to scale
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    1 hr and 9 mins
  • 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
    Nov 5 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
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    1 hr and 45 mins
  • 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
    Oct 29 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
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    1 hr and 12 mins
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