The Nathan Barry Show

Today I'm joined by Sam Vander Wielen, a former lawyer who built an eight-figure creator business while recovering from brain surgery.In this episode, we explore how Sam went from burnt-out lawyer to building a $1.6M/year digital product business with just one full-time employee. She shares the strategy behind her evergreen funnel, the mindset shifts that helped her grow, and the systems that kept the business running after losing both of her parents.Timestamps:00:00 Introduction01:16 Discovering Her True Calling in Business03:00 Frustrations with the Legal Industry06:15 Early Signs of Entrepreneurial Spirit08:55 Food Blog to Legal Templates Pivot10:24 Starting with SEO and Organic Content13:01 First Month Revenue & Early Wins15:47 Scaling to 1.6M with One Product17:19 “All Roads Lead to the Email List”18:42 Evergreen Webinar Funnel that Converts21:04 Ad Strategy & Scaling Mistakes23:29 Voice of Customer Research System26:30 The Power of a Simple Product Suite28:04 Navigating Brain Surgery & Caregiving33:45 Building a Business While Grieving38:50 Dropping Social Media & Saying No41:27 Systems for Automation & Scrubbing43:30 The Power of Writing a Weekly Newsletter44:52 Book Launch: When I Start My Business I’ll Be Happy47:10 Why “Community Over Competition” is BS49:18 Preparing for Craft & Commerce51:17 What’s Next for SamIf you enjoyed this episode, please like and subscribe, share it with your friends, and leave us a review. We read every single one.Learn more about The Nathan Barry Show: 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.comFollow Sam:Newsletter: https://www.samvanderwielen.com/samsidebarInstagram: https://www.instagram.com/samvanderwielenWebsite: https://www.samvanderwielen.comBook: When I Start My Business I’ll Be Happy – available wherever books are soldFeatured in this episode:Ultimate Bundle: https://www.samvanderwielen.com/ultimate-bundleKit: https://kit.comMelissa Griffin: https://melissagriffin.comCraft + Commerce: https://convertkit.com/craft-commerce

Today I'm joined by Jay Singh, AI expert and founder of Casper Studios, to explore how AI is transforming both product creation and internal workflows for creators and businesses alike.We dive deep into the future of personalized software, unlocking AI use cases for creators, and building tools with platforms like Cursor, MindStudio, and Replit. Jay shares how creators can implement fast, practical automations to save time, boost output, and stay ahead in a rapidly changing AI landscape.You'll learn how to identify your best automation opportunities, spin up AI-driven products from transcripts and meeting notes, and use AI to turn raw data into insight, revenue, and leverage.Timestamps:00:00 – Introduction02:17 – Why AI Helps 95% of Tasks—but Gets Used for 50%06:12 – Creators, Voice, and the Future of AI08:33 – Jay’s Background at Microsoft & LinkedIn10:09 – The 3-Step Framework for AI Product Thinking13:26 – Automating Finance, Accounting & Accuracy18:02 – How Jay’s Agency Designs AI Workflows20:19 – Zapier, MindStudio & Real AI Implementations24:36 – Going From Transcript to Product Requirements in Minutes27:11 – V0, Cursor & AI Product Design Workflows33:07 – Kit's App Store Vision & The Future of Personalized Software38:15 – Building AI Tools Without Knowing the Future42:24 – AI Tools Every Creator Should Be Using45:42 – Meeting Transcripts → LinkedIn Content48:19 – AI-Powered Weekly Metrics Reports for Creators51:06 – How to Spot Your Own Automation Opportunities55:09 – Why Everyone Thinks Their Job is “Safe” From AIIf you enjoyed this episode, please like and subscribe, share it with your friends, and leave us a review. We read every single one.Learn more about The Nathan Barry Show: 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.comFollow Jay:LinkedIn: https://www.linkedin.com/in/jaysinghX: https://x.com/JSingh_08Website: https://casperstudios.xyzFeatured in this episode:MindStudio: https://mindstudio.comCursor: https://cursor.shV0: https://v0.devFireflies: https://fireflies.aiReplit: https://replit.comKit: https://kit.com

Today I’m joined by Lars Tiger, a Norwegian music producer who makes $500,000 a year—almost entirely profit—working just two hours a week from his home in the south of France.We dive deep into the experiment that made it possible: releasing thousands of piano tracks with no marketing, using pure volume to generate income and data. Lars shares how he redefined quality, stopped chasing perfectionism, and built a flywheel that creators in any industry can apply.You’ll learn how volume creates financial stability, how to think like a fisherman (not a perfectionist), and why quantity—not quality—is the fastest path to mastery.Timestamps: 00:00 Introduction 01:26 Lars’ $500K/yr, 2-hour workweek model 04:12 Creating 1,000 tracks with zero marketing 08:10 Why 80% quality is enough (and often better) 14:05 The Pottery Class Experiment 17:52 From hits to stability: the math behind his model 20:21 Why Spotify only brings in 15–20% of revenue 22:30 What actually drives plays (hint: not TikTok) 25:42 Helping traditional artists embrace volume 30:38 Can this model scale to $1M+? 34:50 YouTube, repurposing, and platform expansion 39:00 Balancing freedom vs scale 46:04 Faceless creators, pen names, and creative freedom 52:02 What are you optimizing for?If you enjoyed this episode, please like and subscribe, share it with your friends, and leave us a review. We read every single one.Learn more about The Nathan Barry Show: https://nathanbarry.com/showFollow 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.comFollow Lars: Website: https://www.larstiger.com Instagram: https://www.instagram.com/larstiger/ LinkedIn: https://www.linkedin.com/in/larstigerFeatured in this episode: Lars’ Free Music Catalog Course: https://www.larstiger.com ConvertKit: https://convertkit.com Flywheels Course: https://nathanbarry.com/flywheels The Personal MBA: https://personalmba.com#musicproducer #entrepreneur #songwriter

Today I’m joined by Tiffany Uman, a transformational coach and marketing strategist who built her multi‑million dollar coaching business from scratch.In this episode, Tiffany shares the four pillars behind her success, reveals how she transitioned from corporate L’Oréal to launching her business during maternity leave, and outlines her proven strategies for scaling revenue and driving client transformation.Timestamps:00:00 – Introduction01:27 – Tiffany’s Four Pillars of Business Growth03:28 – From Corporate Executive at L’Oréal to Entrepreneur06:39 – Starting a Coaching Business While on Maternity Leave11:24 – Balancing Family & Business Growth16:28 – Identifying and Overcoming Key Man Risk20:19 – The Turning Point: Scaling Beyond $500K24:14 – How to Break Past Growth Plateaus32:00 – Diversifying Revenue Streams & Leveraging B2B37:14 – Tiffany’s Approach to Building a Team41:12 – Elevating Team Members to Reduce Dependency on You45:18 – Identifying & Overcoming Limiting Beliefs49:02 – Using Flywheels to Create Sustainable Growth53:17 – Leveraging AI to Streamline Operations1:00:03 – Where to Follow Tiffany & Closing ThoughtsIf you enjoyed this episode, please like, subscribe, share, and leave a comment with your thoughts or questions for a future episode – we read every single one!Learn more about The Nathan Barry Show: https://nathanbarry.com/showFollow Tiffany Uman:Website: https://tiffanyuman.comLinkedIn: https://www.linkedin.com/in/tiffany-uman-career-strategy-coachInstagram: https://www.instagram.com/tiffany.umanTikTok: https://www.tiktok.com/@tiffany.uman X: https://x.com/tiffanyumanYouTube: https://www.youtube.com/@UCQqfl93s1XEyc5pbMYoyF_g 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 Featured in this episode:Tiffany Uman Coaching - https://tiffanyuman.comAndrew Huberman - https://www.youtube.com/@UC2D2CMWXMOVWx7giW1n3LIg Ryan Holiday - The Obstacle In The Way (book) - https://ryanholiday.net/books-courses/Deliverability Defined Podcast - https://deliverability.transistor.fm/Lil Jon's Wellness Wednesdays - https://liljon.kit.com/newsletterMicrosoft – https://www.microsoft.comL’Oréal – https://www.loreal.comLinkedIn Learning – https://www.linkedin.com/learning

Today I’m joined by Matthew Kepnes (Nomadic Matt) to break down how to turn travel into a profitable business in 2025.Matt has spent over 15 years traveling full-time, building one of the world’s most recognized travel brands. We discuss how travel creators can monetize effectively—through email, events, and brand deals—while staying authentic.Matt shares his five-step system for making money while traveling, from why every creator needs a website to how to sell experiences and build a loyal community.Timestamps:00:00 - Introduction01:22 – From Budget Traveler to Travel Entrepreneur03:06 – The Turning Point: How Matt Built His Blog05:04 – The $75 a Day Strategy: Traveling Affordably07:17 – Why Travel Content is Still Profitable in 202509:30 – The 5 Essential Steps to Making Money While Traveling12:57 – Why Every Creator Needs a Website in 202515:25 – The Power of Email Lists & Webinars for Monetization19:48 – Building Community Through Events & Tours22:55 – The Truth About Travel Brand Deals27:21 – Scaling a Travel Business Without Burnout30:57 – Lessons from Attending 15 Taylor Swift Concerts35:10 – How to Monetize a Travel Blog Without Relying on Ads40:16 – The Best Ways to Land High-Paying Brand Deals45:45 – What’s Changed in the Travel Industry Post-COVID50:26 – The Updated Edition of How to Travel the World on $75 a Day52:30 – Closing Thoughts: The Future of Travel Content CreationIf you enjoyed this episode, please like and subscribe, share it with your friends, and leave us a review. We read every single one.Learn more about The Nathan Barry Show: https://nathanbarry.com/showFollow Nathan:Instagram: https://www.instagram.com/nathanbarry/LinkedIn: https://www.linkedin.com/in/nathanbarry/X: https://x.com/nathanbarryYouTube: https://www.youtube.com/@thenathanbarryshowWebsite: https://nathanbarry.comFollow Matthew:Instagram: https://www.instagram.com/nomadicmatt/Website: https://www.nomadicmatt.comX: https://x.com/nomadicmattLinkedIn: https://www.linkedin.com/in/nomadicmatt/Featured in this episode:How to Travel the World on $75 a Day: https://www.nomadicmatt.com/how-to-travel-the-worldKit: https://kit.comHome Exchange: https://www.homeexchange.comSouthwest Airlines: https://www.southwest.comJapan Rail Pass: https://www.japanrailpass.net

Today I'm joined by Ali Schwanke for a coaching session to map out how she can add $100K in creator income to her thriving services business.We dive deep into pricing, bundling digital products, and leveraging Ali’s existing audience—showing exactly how to build profitable, scalable offers without cannibalizing core services.You'll learn our approach to identifying your best passive income opportunities, packaging your expertise into clear products, and quickly validating your idea before launching.Timestamps:00:00 Introduction01:13 Marketing Is Simple When Your Strategy Is Sound03:07 Escaping Marketing Chaos06:18 Why Most LinkedIn Outreach Fails08:02 How Ali Built Simple Strat10:08 Growing Her HubSpot YouTube Channel15:59 Mapping Revenue & Audience Assets21:11 Finding Ali’s Best Passive Income Opportunities25:48 How to Price & Package Digital Products38:51 Using Decoy Pricing To Boost Sales46:39 Designing the Perfect Pilot Program55:18 Recap & Next StepsIf you enjoyed this episode, please like and subscribe, share it with your friends, and leave us a review. We read every single one.Learn more about The Nathan Barry Show: 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.comFollow Ali:LinkedIn: https://www.linkedin.com/in/alischwankeWebsite: https://www.alischwanke.comInstagram: https://www.instagram.com/alischwanke/X: https://x.com/alischwankeYouTube: https://youtube.com/@HubSpotHacksFeatured in this episode:Simple Strat: https://www.simplestrat.comMarketing Deconstructed: https://marketingdeconstructed.comHubSpot Hacks: https://youtube.com/@HubSpotHacksTubebuddy: https://www.tubebuddy.comKit: https://kit.comHighlights:00:09 – We need to retrain how we think about marketing01:13 – “Marketing is simple when strategy is sound”03:07 – Start with what already works08:20 – From YouTube tutorials to a $2M agency16:00 – Potential offers and decoy pricing45:40 – Becoming the “Oprah of marketing”

Today I’m joined by Charli Prangley as we revisit our bold rebrand from ConvertKit to Kit - a journey of rapid change, decisive leadership, and preserving what truly matters. In this episode, we explore how we built a new identity without starting from scratch, the lessons learned along the way, and how our internal culture has evolved as a result.Timestamps:00:00 Introduction to Branding00:49 The Kit Rebrand Journey01:55 Lessons Learned from Rebranding05:11 Maintaining Brand Equity06:39 Challenges and Successes08:25 The Importance of Brand Strategy12:42 Messaging and Positioning15:33 Internal Shifts and Bold Actions18:56 Kit's Self-Belief and Leadership22:45 Creating Tutorials and Overcoming Roadblocks24:51 Celebrity Endorsements and Success Stories25:28 The Impact of a Strong Brand31:24 Executing a Successful Rebrand36:27 Dreaming Big and Making It Happen39:27 Reflecting on Leadership and Growth43:13 Final Thoughts and EncouragementIf you enjoyed this episode, please like and subscribe, share it with your friends, and leave us a review. We read every single one.Learn more about The Nathan Barry Show: 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.comFollow Charli:Instagram: https://www.instagram.com/charliprangleyLinkedIn: https://www.linkedin.com/in/charliprangleyTwitter: https://twitter.com/charliprangleyYouTube: https://www.youtube.com/user/charlimarietvWebsite: https://charlimarie.comFeatured in this episode:Kit: https://kit.comKoto (Brand Strategy Partner): https://www.kotoagency.comSquare Black (Development Agency): https://squareblack.comTom Brady’s Newsletter: https://www.tombrady.com/newsletterMorgan Freeman: https://themorganfreeman.comHighlights:06:03 – Churn: The Leaky Bucket Challenge15:05 – Unpacking the 6-Step Direct Sales Flywheel22:05 – Overcoming Migration Objections with Concierge Setups29:21 – The Zero-to-One of Personal Branding36:08 – Scheduling & Measurement: Locking In Daily Priorities49:20 – Innovating Pricing Strategies for Expansion Revenue

Today I’m joined by Laura Sprinkle for a live coaching session on scaling her new affiliate-tracking SaaS, Rootabl, from $5,000 MRR to $25,000 MRR while maintaining the flexibility and freedom she values. Laura has deep expertise in affiliate launches and is now shifting into the software world - facing new challenges like churn, onboarding friction, and deciding which features to build first.We map out her next steps - from clarifying her ideal target customer and harnessing personal branding for trust, to using direct outreach as a repeatable engine for sustainable growth. You’ll learn why concierge migrations can be a secret weapon, how to choose the right community integrations, and why narrowing your audience often leads to better results.Timestamps:00:00 Introduction01:14 Why Creator-Led SaaS Is Harder (Yet More Rewarding)02:39 How Laura Reached $5K MRR07:36 Tackling Churn and Onboarding Friction11:29 Using Personal Branding to Increase Conversions14:55 The Direct Sales Flywheel Explained19:48 Turning “Concierge Migrations” into a Competitive Advantage30:57 Choosing Your Integrations Wisely31:24 New Features vs. Doubling Down on Existing Ones37:17 Reducing Churn40:16 Narrowing Your Customer Profile for Faster Growth45:45 Using Outreach to Drive Predictable Revenue47:11 Introducing Tiered Pricing for Expansion50:26 Tracking Progress & Staying Focused51:52 The Power of Iteration in SaaS Growth01:02:54 Closing ThoughtsIf you enjoyed this episode, please like and subscribe, share it with your friends, and leave us a review. We read every single one.Learn more about The Nathan Barry Show: https://nathanbarry.com/show Follow Nathan:Instagram: https://www.instagram.com/nathanbarry/LinkedIn: https://www.linkedin.com/in/nathanbarry/ X: https://x.com/nathanbarry YouTube: https://www.youtube.com/@thenathanbarryshow Website: https://nathanbarry.com Follow Laura:Website - https://laurasprinkle.com/ Rootabl (10% discount) - https://rootabl.com/special-offer/ Instagram - https://www.instagram.com/imlaurasprinkle/ Linkedin - https://www.linkedin.com/in/imlaurasprinkle/ Featured in this episode:- Rootabl: https://rootabl.com - Kit: https://kit.com - Mighty Networks: https://www.mightynetworks.com

Today I'm joined by Haley from the Kit team for a Q&A where we answer your questions about building a creator business that lasts.We explore everything from why major celebrities are suddenly launching newsletters to the practical choices creators face - like when to stay solo versus build a team, or whether to focus on high-ticket or low-ticket offers. Plus, we share real examples from both sides of these decisions.You'll learn how to make strategic choices that fit your goals, build sustainable systems that scale, and maintain balance while growing your business.Timestamps:00:00 - Introduction02:02 - The Truth About Working with Matthew McConaughey05:07 - Why Everyone is Launching a Newsletter (And Should You?)12:13 - Which Celebrities Should Start a Newsletter?15:46 - How Do You Balance Creativity With Execution?19:42 - Should Entrepreneurs Build a Personal Brand?30:59 - How Do Successful Creators Prioritize Self-Care?37:27 - High-Ticket vs. Low-Ticket Offers: Which Makes More Money?42:31 - How Far Can You Grow as a Solo Entrepreneur?49:00 - Are You a Creator, a Coder, or a CEO?53:34 - Should You Focus More on Product Creation or Marketing?57:24 - How to Stay Productive Without Burning Out01:01:12 - How Does Nathan Get More Done Than Most People?01:05:00 - Closing ThoughtsIf you enjoyed this episode, please like and subscribe, share it with your friends, and leave us a review. We read every single one.Learn more about The Nathan Barry Show: 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 Follow Haley:Instagram: https://www.instagram.com/haleyjaniLinkedIn: https://www.linkedin.com/in/haley-janicekX: https://twitter.com/haleyjanicekFeatured in this episode:Kit: https://kit.comBrian Feroldi: https://www.brianferoldi.com/Matthew McConaughey’s Newsletter: https://lyricsoflivin.com/Hasan Minhaj: https://www.hasanminhaj.com/Morgan Freeman: https://www.instagram.com/morganfreeman/Lil Jon’s Newsletter: https://liljon.kit.com/newsletter/Tom Brady’s YouTube: https://www.youtube.com/@tombrady/Tom Brady’s Newsletter: https://tombrady.com/Cristiano Ronaldo’s YouTube: https://www.youtube.com/@cristiano/The Armchair Expert: https://armchairexpertpod.com/Damian Lillard: https://www.instagram.com/damianlillard/Jo Franco: https://www.instagram.com/jo_franco/Caitlin Clark: https://www.instagram.com/caitlinclark22/Travis Kelce: https://www.instagram.com/killatrav/Jason Kelce: https://www.instagram.com/jason.kelce/Kylie Kelce: https://www.instagram.com/kykelce/Dermot Kennedy: https://www.dermotkennedy.com/Codie Sanchez: https://codiesanchez.com/Justin Welsh: https://www.linkedin.com/in/justinwelsh/Danny Iny: https://www.linkedin.com/in/dannyiny/Jed Eglington Episode: https://nathanbarry.com/60/Sahil Bloom: https://www.sahilbloom.com/James Clear: https://jamesclear.com/Paperboy: https://www.paperboystudios.co/Derek Sivers: https://sive.rs/

Today I'm joined by Isaac French for a coaching session on his next moves after turning a $2.3 million property investment into a $7 million exit, while building multiple six-figure digital revenue streams. We map out his options - from launching a content agency and building more properties to scaling his YouTube presence - and explore how to choose between opportunities when you're optimizing for both impact and quality of life. You'll learn our framework for evaluating opportunities, why enterprise value isn't just about tangible assets anymore, and how to grow strategically without sacrificing what matters most.Timestamps:00:00 Introduction01:29 How I Sold an Airbnb Business for Millions03:26 Email Marketing Funnel That Makes $200K/Year07:36 Should I Start an Agency, SaaS, Real Estate Business, or Creator Business?11:29 Starting an Agency vs Building SaaS14:55 Evaluating Future Paths19:48 Making Money vs Quality of Life as an Entrepreneur30:57 Why Isaac Keeps His Business Team Small31:24 The Truth About Starting Agencies and SaaS Businesses37:17 Exploring New Property Ideas40:16 The Value of a Small Property45:45 Growing on YouTube as a Business Owner47:11 Growing an Email Newsletter50:26 Balancing Cash Flow and Equity51:52 The Value of Audience and Personal Brand01:02:54 Closing ThoughtsIf you enjoyed this episode, please like and subscribe, share it with your friends, and leave us a review. We read every single one.Learn more about The Nathan Barry Show: 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 Follow Isaac:Instagram: https://www.instagram.com/isaacfrench_ Website: https://www.isaacjfrench.com X: https://twitter.com/isaacfrench_ LinkedIn: https://www.linkedin.com/in/isaacjfrench Featured in this episode:Kit: https://kit.com Darrell Vesterfelt: https://darrellvesterfelt.com Sean Sweeney: https://www.seandsweeney.com New Story: https://www.newstoryhomes.org Brett Hagler: https://www.bretthagler.com Live Oak Lake: https://www.liveoaklake.com Paperboy: https://www.paperboy.co Nick Huber: https://www.instagram.com/sweatystartup Somewhere: https://www.somewhere.com Marshall Haas: https://www.marshallhaas.com Sahil Bloom: https://www.sahilbloom.com Shane Martin: https://www.linkedin.com/in/shane-martin-micro Lil Jon's Newsletter: https://liljon.kit.com/newsletter Codie Sanchez: https://codiesanchez.com Dan Martell: https://www.danmartell.com Mark Manson: https://markmanson.net Highlights:10:51 The Warren Buffett Secret to Success21:06 The Two Sides of Wealth: Cash Flow vs. Enterprise Value24:13 Every Creator Needs to Master Taxes30:30 Small Teams, Big Visions31:46 The Slow Climb to SaaS Success32:12 Building Paperboy52:34 Idea Banking