Épisodes

  • 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 h et 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
    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 h et 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
    Oct 22 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
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    1 h et 28 min
  • AI Can't Copy This: Why Every Creator Needs an Origin Story in 2026 | Philip mckernan | 150

    AI Can't Copy This: Why Every Creator Needs an Origin Story in 2026 | Philip mckernan | 150
    Oct 15 2026

    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
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    1 h et 19 min
  • The #1 Way to Grow Your Audience in 2026 | Domonkos Eross | 149

    The #1 Way to Grow Your Audience in 2026 | Domonkos Eross | 149
    Oct 8 2026

    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
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    1 h et 8 min
  • How to Build an Unforgettable Personal Brand | Chris Do | 148

    How to Build an Unforgettable Personal Brand | Chris Do | 148
    Oct 1 2026

    Personal brand has become one of the biggest buzzwords in the creator world. Creators everywhere are launching offers, building funnels, and posting consistently, yet very few are creating something people actually remember.

    I sat down with Chris Do, Emmy award-winning designer and founder of The Futur, to talk about what it really takes to build a personal brand that stands out. We get into why most creators end up serviceable but forgettable, why branding comes down to differentiation, and the three-part framework behind brands people obsess over. Chris also shares why the real work of personal branding happens internally, how to find your voice phrase, and the trust triangle that decides who audiences believe. Partway through, he turns the interview around and starts coaching me, and we go much deeper than I expected.

    If you're building a personal brand and wondering why it isn't resonating yet, I think you'll get a lot out of this conversation.

    Timestamps:
    00:00 Introduction
    01:39 What it means to un-bland yourself
    02:48 Why branding is all about differentiation
    03:04 Why Apple has a brand and Dell doesn't
    04:31 How status and identity drive what we buy
    07:29 How Target built a brand
    10:42 How Kit positions its brand
    11:44 Moving from features to meaning
    14:11 Why most personal brands are really marketing funnels
    16:11 Why personal brand work is internal
    16:26 How we lose who we really are
    19:04 Chris starts asking the questions
    20:24 How getting sick at 24 changed Nathan's identity
    21:51 Why we tie our identity to what we do
    23:03 Who are you outside of your work?
    23:36 Why you are the gift
    25:51 How Chris answers "who are you?"
    26:36 The difference between design and art
    28:45 Why being true to yourself comes first
    29:45 Nathan's mission
    32:24 Why Chris moved from commercial work to content
    33:36 Why your brand needs to stand against something
    35:44 Finding your keyword and your nemesis
    37:03 Why the best heroes have great enemies
    40:39 The three-part personal brand framework
    41:49 Chris's own brand triangle
    42:33 Workshopping Nathan's personal brand
    43:30 Separating who you are from your company
    44:44 The story behind Chris's mission
    47:25 Why all strategy is autobiographical
    48:13 Nathan on feeling like a burden
    49:29 Nathan's story about his stepdad
    53:49 Chris's read on Nathan's story
    56:36 Finding Nathan's rallying cry
    59:28 Learning to accept help
    1:01:26 Why we trust people who aren't perfect online
    1:02:00 The trust triangle
    1:04:52 How to find your voice phrase
    1:08:21 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 Chris:
    Instagram: https://www.instagram.com/thechrisdo
    X: https://x.com/thechrisdo
    LinkedIn: https://www.linkedin.com/in/thechrisdo
    YouTube: https://www.youtube.com/@thefutur
    Website: https://thefutur.com

    Featured in this episode:
    Kit: https://www.kit.com
    The Futur: https://thefutur.com

    Highlights:
    03:04 Why Apple has a brand and Dell doesn't
    14:11 Why most personal brands are really marketing funnels
    40:39 The three-part framework behind Bryan Johnson's brand
    49:14 Chris turns the interview around
    1:05:17 How to find your voice phrase
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    1 h et 9 min
  • Forget Courses, Sell This in 2026 To Make 7 Figures | Jasmine Star | 147

    Forget Courses, Sell This in 2026 To Make 7 Figures | Jasmine Star | 147
    Sep 24 2026

    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
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    1 h et 13 min
  • $300M+ Founder: What Nobody Tells You Before Selling Your Business | Ankur Nagpal | 146

    $300M+ Founder: What Nobody Tells You Before Selling Your Business | Ankur Nagpal | 146
    Sep 17 2026

    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

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    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
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