The Nathan Barry Show

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 Introduction 01:37 Why growth tactics are only 1 of 5 levers 02:03 How Chenell hit 21,000 subscribers in 10 months 03:29 Why going deeper than everyone else stands out 04:40 Lever 1: Insanely valuable content 06:24 6 ways to make content insanely valuable 08:34 Mario Gabriele's S-1 breakdowns 10:11 Making readers the smartest person in the room 12:40 Why you should get on calls with your readers 13:28 Lever 2: Positioning 13:55 How a food waste app became The ADHD Weasel 16:05 Why positioning changes over time 18:54 How to find readers to talk to 20:28 How reader calls shaped Sam Vander Wielen's bundle 21:19 Lever 3: Building momentum 21:56 Why you should pick one platform 22:15 Why quizzes are working so well 26:21 The quiz that 9X'd The ADHD Weasel's growth 27:16 How to get noticed by creators you admire 28:46 Building a quiz for The Ladders of Wealth 29:47 Lead magnets that don't need new content 30:39 Using AI skills as lead magnets 32:01 Why you should post more on social 35:05 How to mine your best content 38:34 Why it's okay to repeat your best stories 39:43 Lever 4: Conversion 41:55 Chenell's spicy take on Linktree 43:35 How Dru Riley got a landing page to 40% 45:55 Why the wrong views won't convert 48:27 How Pat Walls positioned Starter Story's paid product 50:54 Lever 5: The one hardly anyone is doing 51:39 Why you need an "almost there" page 53:24 What makes a great welcome email 55:52 How to surprise new subscribers 58:21 Doing what bigger creators can't 1:02:12 Why you should subscribe to your own newsletter 1:03:55 Chenell audits Nathan's newsletter 1:06:38 The bar for Nathan's newsletter content 1:09:20 Splitting the podcast into its own email 1:11:36 Turning the book launch into content 1:13:44 Chenell reads Nathan's homepage headline 1:16:36 Sharing your success without bragging 1:18:42 Promoting the newsletter inside episodes 1:22:56 Fixing Nathan's conversion points 1:26:14 The hidden cost of double opt-in 1:29:49 How newsletters monetize 1:31:46 Why Packy McCormick's sponsored deep dives work 1:33:19 Group coaching and high-ticket offers 1:36:00 The pricing sweet spot for memberships 1:37:26 When paid newsletters work 1:40:48 How to price a paid newsletter 1:43:57 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 Chenell: Instagram: https://www.instagram.com/chenellco X: https://x.com/chenellco LinkedIn: https://www.linkedin.com/in/chenellco YouTube: https://www.youtube.com/@growthinreverse Website: https://growthinreverse.com Featured in this episode: Kit: https://www.kit.com Growth In Reverse: https://growthinreverse.com Newsletter scorecard: https://growthinreverse.com/scorecard The Generalist: https://www.generalist.com The ADHD Weasel: https://adhdweasel.substack.com Trends.vc: https://trends.vc Starter Story: https://www.starterstory.com The Ladders of Wealth: https://laddersofwealth.com Highlights: 06:24 The 6 ways to make content insanely valuable 26:37 The quiz that 9X'd The ADHD Weasel's daily growth 50:54 The growth lever almost no one is using 1:13:44 Chenell roasts Nathan's newsletter 1:31:46 How Packy McCormick gets paid 5 to 10X for sponsored deep dives

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 Introduction 01:22 The AI workflow every creator should set up 02:43 How Dan writes by talking to his AI 04:21 Why computer use is suddenly so good 05:12 How an agent reordered Dan's 8,000-word story 07:31 Turning an editor's taste into an AI skill 09:44 How to build a skill without writing it yourself 10:49 Using evals to make your skills better over time 12:45 Should you go deep on one AI platform? 15:29 Nathan's AI workflow for following up after events 18:24 Why Dan is so optimistic about AI 20:55 The three stages of adapting to new technology 23:59 Ambition in the age of AI 25:30 Why creators should stay diversified 26:01 Building an app for your audience in a weekend 27:08 Why every creator can now have a feed 29:08 How Dan uses custom feeds to run Every 31:06 Everyone can now work like Ryan Holiday 32:08 Why AI curation hasn't caught up with creation 32:51 Frontier alerts and writing for each reader 34:29 Why Every is hiring more engineers than ever 37:02 Why Dan says the newsletter is dead 40:21 When your open rate drops to zero 41:05 Seth Godin and being missed when you don't publish 42:27 Why OpenAI and Claude will build a new inbox 43:43 What actually replaces email? 46:26 How Dan is positioning Every for what's next 47:25 Why Every may stop chasing email signups 48:35 Pushing content through MCP servers 49:52 What creators should do to get ready 51:59 Why quality matters more than ever 54:00 What a high-quality audience has done for Dan 55:21 Why Nathan is underusing his AI tools 56:44 The Eight Levels of AI 58:02 How Every makes money 58:53 Splitting Every into frontier and product teams 1:01:56 Pirates vs architects 1:02:41 Kit's App Store and the cost of experiments 1:03:54 How Every launches experiments it won't support 1:06:04 Dan's hot take on AI and jobs 1:07:23 What Andrew Carnegie's story teaches us 1:08:07 What Dan is reading right now 1:10:24 Where to start with Every 1:11:05 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 Dan: X: https://x.com/danshipper LinkedIn: https://www.linkedin.com/in/danshipper Website: https://danshipper.com YouTube: https://www.youtube.com/@EveryInc/videos Featured in this episode: Kit: https://www.kit.com Every: https://every.to How Codex Happened: https://every.to/p/how-codex-happened The Eight Levels of AI Adoption: https://every.to/guides/the-eight-levels-of-ai-adoption After Automation: https://every.to/chain-of-thought/after-automation Highlights: 02:43 Why Dan writes by talking out loud to his AI 08:35 Turning 40,000 copy edits into a "Kate pass" 21:17 The agency rupture everyone feels with AI 37:29 Why the newsletter as we know it is dead 47:25 The one number Every might stop chasing

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 Introduction 01:23 How Jayson connected Nathan to 50 entrepreneur friends 02:15 Why Jayson wasn't always a super connector 02:57 The loneliness that led to Mastermind Dinners 04:14 Never beg for a seat when you can build your own table 05:29 Why the host gets the most status in the room 06:14 Lower-lift ways to bring people together 06:49 How Summit Series started with a ski trip 08:57 Start with the easiest yes 09:28 The anchor tenant strategy 10:27 Nathan's author mastermind with James Clear 11:06 Partnering to host the room 12:35 Organizing a team to play above your level 13:21 Will Guidara's gratitude for being invited 14:51 Buying access and the speed of relationships 15:43 Money, moxie, and service 15:58 Andrew Wilkinson's $57,000 lunch with Bill Ackman 17:58 Moxie and the power of cold emails 19:30 The man who stood up Mark Zuckerberg 20:45 Nathan chickens out of meeting his heroes 22:55 Eight seconds of courage 24:02 Leaving energy vs. lingering energy 24:47 Nathan's 45-second intro to Chris Brogan 25:44 How a quick hello led to a call with Steven Bartlett 27:06 Why you shouldn't put people on a pedestal 27:53 Abundance vs. scarcity when meeting people 29:47 Service and Ryan Holiday's apprenticeship 31:20 Why Benjamin Graham told Warren Buffett he was overpriced 31:58 Why "How can I help?" is the wrong question 32:18 How Jayson built a relationship with Shep Gordon 33:12 How to offer help that's actually specific 36:00 The relationships that weigh you down 38:55 Why all relationships go dormant naturally 39:45 Why entrepreneurs and creators feel isolated 41:17 Craft + Commerce as an annual pilgrimage 42:35 Conferences vs. masterminds vs. communities 46:00 Conversations that normally take years 48:00 Do great work and your network will find you 49:55 How great work raises your hit rate 51:54 Why you're not ready for Diary of a CEO 53:35 Putting in the reps on camera 54:28 Ramit Sethi's advice on media training 56:39 Increasing your surface area of luck 59:38 Jayson's friends-only email updates 1:02:06 The email that saved MMT in 2020 1:04:59 Who to include on your update list 1:05:50 Nathan's missing annual review 1:07:22 The 90-minute quarterly update 1:08:17 A fan base vs. a community 1:09:59 Curating like the bouncer at the club 1:10:36 Kit's triads and MMT's MM3s 1:15:00 People come for content, stay for community 1:15:47 The ask, give, praise model 1:18:26 How praise reinforces the value of the network 1:21:02 Praise cards mailed 90 days later 1:24:18 Why the book is called Community Made 1:27:06 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 Jayson: Instagram: https://www.instagram.com/jaysongaignard X: https://x.com/jaysongaignard LinkedIn: https://www.linkedin.com/in/jaysongaignard Website: https://www.jaysongaignard.com Featured in this episode: Kit: https://www.kit.com MMT: https://mmt.community Community Made: https://communitymade.com Highlights: 02:22 Jayson had two people at his bachelor party 24:02 Leaving energy vs. lingering energy 49:55 Why great work changes your hit rate on everything 1:02:06 The friends-only email that saved MMT 1:21:02 The praise cards Jayson mails out 90 days later

The story you leave out of your content could be the reason someone connects with your work. I sat down with Philip McKernan, author of One Last Talk, who has helped Olympians and World Cup athletes and consulted with the US Army and the Pentagon. We get into why your origin story matters, how to recognise the gifts you undervalue, and why the fear that drives success can eventually become exhausting. Philip walks me through his framework connecting story, gift, and impact, then coaches me live through my discomfort with promoting my upcoming book. A simple drawing exercise leads to a challenge I wasn’t expecting about who I’m letting down by holding back. If you’re building a personal brand but feel uncomfortable sharing your story or promoting your work, I think you’ll get a lot out of this conversation. Timestamps: 00:00 Introduction 02:00 The business pitch that needed a personal story 07:00 Philip’s own origin story 11:00 Helping an athlete reconnect with his purpose 17:00 Finding the gift you overlook 21:00 When fear-driven ambition becomes exhausting 24:00 Why I’m not afraid of my business disappearing 34:00 Buying a castle when business was down 95% 38:00 Building a better relationship with yourself 40:00 Why asking for help feels uncomfortable 43:00 Philip coaches me through a drawing exercise 47:00 The challenge I wasn’t expecting 54:00 Why being visible can feel frightening 57:00 An exercise to uncover your story 1:03:00 Understanding what your happiest days reveal 1:09:00 Learning from your darkest days 1:16:00 How sharing your story creates connection 1:18:00 Final thoughts and where to find Philip 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 Philip: Instagram: https://www.instagram.com/philip_mckernan/ LinkedIn: https://www.linkedin.com/in/philip-mckernan YouTube: https://www.youtube.com/@philipmckernan Website: https://philipmckernan.com Featured in this episode: Kit: https://kit.com One Last Talk: https://onelasttalk.com The Ladders of Wealth: https://www.simonandschuster.com/books/The-Ladders-of-Wealth/Nathan-Barry/9798893312393 Highlights: 02:00 The business pitch that needed a personal story 21:00 When fear-driven ambition becomes exhausting 43:00 Philip coaches me live 47:00 Why we undervalue our own work 57:00 An exercise to uncover your story

Most creators try to grow by posting more. More content, more platforms, more hours. But the biggest creators and thought leaders grow in a very different way, and most of it happens behind the scenes. I sat down with Domonkos "Doma" Eross, founder of Flowin, a creative agency for thought leaders, to talk about what actually drives audience growth right now. We get into his seven strategic steps to succeed as a thought leader, why creator partnerships are the number one source of growth in the creator economy, and Doma’s outreach technique for landing dream clients. If you've ever wanted to know the systems the biggest creators use to consistently grow their audiences, I think you'll get a lot out of this conversation. Timestamps: 00:00 Introduction 01:33 How Doma started working with thought leaders 03:03 Why direct outreach works 03:33 The Manchester United cold email 05:05 Why a well-packaged pitch gets attention 06:49 Using credibility to get past the first filter 08:06 How office hours turned into clients 09:13 Leaving energy vs lingering energy 10:13 Why curiosity beats a target list 11:59 How your network compounds 12:54 The seven steps to succeed as a thought leader 13:18 Step 1: Develop exceptional knowledge first 14:17 Step 2: Define your mission and theory of change 16:19 Step 3: Build an ecosystem strategy 18:21 Matching your ecosystem to how you make money 19:51 Step 4: Turn your ideas into the right content 21:18 Protecting clients from the wrong projects 22:38 Step 5: Build the right team 23:12 Why team size and influence don't correlate 24:55 How James Clear decides what to work on 26:32 Building a team around impact 28:26 The most surprising role on a thought leader's team 30:53 What thought leaders know about saying no 32:17 Focus on your craft and outsource the rest 33:22 Step 6: Creator partnerships, the #1 source of growth 35:14 Why Creator Network works better than list swaps 37:19 How partnerships work at a smaller scale 39:00 How much growth Creator Network drives 40:27 Why partnerships are a win-win 41:22 Set up partnerships before your podcast episode airs 44:27 Why the creator economy isn't competitive 46:32 What Doma has learned from his clients 47:57 Step 7: Build and perfect your organic channels 48:13 Why your newsletter is the only channel you own 49:56 Building a newsletter that sounds like you 53:05 The three phases of a book launch 54:15 Teasing your book in your newsletter 55:26 Why you need to book podcasts months ahead 56:08 The concentrated strike approach 56:34 How to pitch the biggest podcasts 58:48 Which podcasts actually sell books 59:50 The people behind podcast bookings 1:01:36 Using a live event to launch a book 1:03:37 How Doma runs Flowin 1:05:08 Why Doma doesn't want to scale 1:06:40 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 Doma: LinkedIn: https://www.linkedin.com/in/domonkoseross Website: https://flowin.consulting Featured in this episode: Kit: https://www.kit.com Flowin: https://flowin.consulting Highlights: 03:33 The Manchester United cold email 13:18 Why thought leadership is the result, not the goal 24:55 How James Clear decides what to work on 33:22 The #1 source of growth in the creator economy 53:05 The three phases of a book launch