The Nathan Barry Show

What does it take to scale a business to a multi-million dollar enterprise and beyond, all while maintaining profitability and a thriving culture? Chandler Bolt, founder of selfpublishing.com sits down in his bustling office to reveal the crucial shifts and strategic insights that propelled his company from the initial million-dollar milestone to hitting the ambitious $10 million mark and charting a course for even greater heights. From turning business into a game complete with scoreboards and "green days" to mastering product-market fit and the art of "reverse selling" in hiring, Chandler shares the unconventional wisdom he's gained on his journey. This episode is packed with candid advice for entrepreneurs at every stage, exploring the often-overlooked distinctions between revenue and profit, the true cost of growth, and the surprising benefits of in-person collaboration in an increasingly remote world. Timestamps: 00:00 Introduction 07:11 The three most important metrics & activities 14:26 Is the first million the hardest? 21:07 Profit over revenue for scaling 27:18 Three ways to grow a business 32:00 Reverse selling to attract top talent 37:29 Offboarding team members gracefully 43:24 The power of implementing strong processes 49:50 The need for scalable customer acquisition at $10M+ 55:23 The shift to an in-person culture 01:00:30 Remote vs. in-person debate 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 Chandler: YouTube: https://www.youtube.com/@ChandlerBoltOfficial Instagram: https://www.instagram.com/realchandlerbolt TikTok: https://www.tiktok.com/@realchandlerbolt LinkedIn: https://www.linkedin.com/in/chandlerbolt Facebook: https://www.facebook.com/chandler.bolt1 Website: https://www.selfpublishing.com Book a call with Chandler’s team: http://selfpublishing.com/work-with-us Featured in this episode: Kit: https://www.kit.com Self Publishing: https://www.selfpublishing.com

Steering a company from nascent idea to multi-million dollar revenue is rarely a smooth ride. Often, it's a journey fraught with uncertainty, tough decisions, and the internal battles no one sees. For Nathan, the guiding hand through much of this journey has been his coach, Dan Putt. As a co-founder of Reboot, Dan has spent years working with leaders and executives, helping them navigate growth without losing themselves in the process. In this episode, Dan shares not only his unique coaching philosophy - which emphasizes a deep, inside-out understanding of oneself, but also practical tools and frameworks that address common founder sticking points like imposter syndrome, the fear of conflict, and the allure of the "magic bullet" solution. Get ready to rethink your approach to leadership and personal development. Timestamps: 00:00 Introduction 02:23 Dan's coaching philosophy 04:36 The Greek God CEO and imposter syndrome 07:11 The "have to" versus "get to" reframe 10:00 What problems say about identity 12:56 Listening to understand: Beyond the words 15:46 Inside-out leadership development 18:31 The challenge of competitive responses 21:52 Journaling for self-discovery 25:21 Practical tips for consistent journaling 28:11 Getting clear on what you truly want 30:26 The "loyal soldier" concept 33:53 How personal traits drive ambition 38:39 The shift from "need" to "want" 41:43 Conflict as progress and care 45:34 Tools for navigating conflict 50:47 The "net" framework for communication 52:23 Avoiding problems vs. facing them 55:29 The temptation of the "magic bullet" 59:08 Feeling the fear without dwelling 1:01:21 The tantruming toddler metaphor for anxiety 1:03:00 Leading with curiosity, not fear 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: Website: https://danputt.com LinkedIn: https://www.linkedin.com/in/danputt X: https://twitter.com/danputt Company Website: https://reboot.io Featured in this episode: Kit: https://www.kit.com Reboot.io: https://reboot.io The Artist's Way by Julia Cameron: https://juliacameronlive.com/books/the-artists-way 750words.com: https://750words.com The Obstacle Is the Way by Ryan Holiday: https://ryanholiday.com/books/the-obstacle-is-the-way Extreme Ownership by Jocko Willink: https://echelonfront.com/Extreme-Ownership Highlights: 02:47 Understanding the spectrum of coaching approaches 08:24 The danger of linking self-worth to problems 13:44 The wisdom found at the emotional level 23:25 The clarifying power of daily journaling 34:05 How the "loyal soldier" shapes our drives 45:51 Why true care often requires conflict 53:49 Facing uncomfortable feelings builds resilience 1:01:05 Approaching anxiety like a tantruming child 1:03:54 Shifting from fear to wonder for better leadership

Start 2026 strong with a handpicked collection of the best advice from this year's top moments! This episode is a treasure trove of actionable insights designed to elevate your business and personal growth. We've curated the moments that resonated most, offering practical strategies for everything from scaling your business and building a thriving community to mastering content creation and leveraging social media. Get ready to learn from the best and apply these game-changing lessons to achieve your goals this year! Timestamps: 00:00 Introduction 00:30 Dan Martell: The Buyback Loop for Capacity 01:56 Transferring Tasks with the Camcorder Method 04:05 Filling Your Calendar with High-Value Activities 06:00 Mindset and Beliefs for Growth 07:51 Chris Donnelly: The Cohort Model for Scaling 11:16 The Scarcity Principle in Product Launches 13:40 Jay Clouse: Building Small, Engaged Communities 16:16 The Gold Standard of Community Building 17:38 Pat Flynn: YouTube Shorts to a Million Subscribers 19:14 The Power of Quantity Over Quality 21:55 Nicole Burke: Instagram as a Storefront 24:05 Creating Entertaining Content that Drives Shares 26:49 Jefferson Fisher: Crafting Viral Reels Without a Script 29:52 Testing and Refining Your Reel Content 31:37 The Crucial First Three Seconds of a Reel 33:10 Avoiding Subjective Content Judgment 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 Featured in this episode: Kit: https://www.kit.com Highlights: 00:25 – Dan Martell's Capacity Buyback Loop 04:25 – The Ladder of Success for Habits & Skills 08:01 – Chris Donnelly's Cohort-Based Course Model 13:44 – Building Small, Engaged Communities Effectively 17:42 – Pat Flynn's YouTube Shorts Million Milestone 21:55 – Nicole Burke on Instagram Storefront Strategy 31:37 – Jefferson Fisher's Tips for Viral Reel Hooks

Many entrepreneurs and marketers feel like they've missed the boat on short-form video. The common thought: "That worked a few years ago, but it's too saturated now." But what if that's a myth? Colin Landforce, founder of Cut30, argues that with a unique perspective and consistent effort, anyone can achieve massive results, regardless of follower count. He's seen students with under 1,000 followers generate tens of thousands in revenue, proving you don't need millions of views to make a significant business impact. Colin reveals his three-step framework for taking short-form video seriously, alongside the critical role of hooks, and how to simplify your strategy to win big. Timestamps: 00:00 Intro: The biggest opportunity in media 01:14 Why short-form video is a generational opportunity 02:26 Breaking the myth of saturation 05:48 The power of small audiences 10:48 Why founders should create their own short-form content 12:50 The shift from side project to serious business 14:39 Break the seal - just start 17:08 How to make your first simple "one shot" video 20:25 Learn the edit - basic chops in CapCut 23:33 The importance of efficiency in short-form content 29:26 Do it again tomorrow - consistency is key 34:13 How to generate an endless supply of content ideas 36:03 The three keys to a compelling hook 37:41 The "everyone's been asking me" hook 40:28 The impact of visual hooks beyond motorcycle crashes 43:01 The power of props in visual hooks 48:16 Brainstorming short-form content from this podcast episode 50:45 Crafting a tight, efficient short-form video example 54:51 Why short-form is Colin's primary driver for any business 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 Colin: Instagram: https://www.instagram.com/landforce TikTok: https://www.tiktok.com/@landforce_ LinkedIn: https://www.linkedin.com/in/colinlandforce Cut30: https://course.cut30.co Website: https://landforce.com Featured in this episode: Kit: https://www.kit.com Cut30: https://course.cut30.co Highlights: 02:15 The myth of saturation in short-form video 06:02 Small audience, huge business impact 14:08 Short-form video: the biggest opportunity in media 24:41 The accordion method for content efficiency 32:36 Track inputs, not outputs, for personal growth 52:12 Words to make your hook more efficient 56:45 Localized algorithms for niche businesses

The secret to building a content machine that reaches millions, all without spending a dime on ads? According to Ryan Holiday, it starts with making content people actually want to consume. In this live interview from Austin, Texas, Ryan pulls back the curtain on how Daily Stoic went from an obscure philosophy discussed only in academia to a global phenomenon. From cultivating an audience one platform at a time to transforming a single piece of content into a multi-platform strategy, discover the counterintuitive lessons from a master of timeless ideas and modern media. This isn't just about stoicism; it's a masterclass in building a resilient, impactful career designed to stand the test of time. Timestamps: 00:00 Building a timeless content machine 02:17 Why ditch every ad and pivot to content? 06:07 The power of algorithms and meeting your audience where they are 08:27 Creating content you genuinely want to make 10:49 The Marathon video and turning experiences into content 13:26 Crafting a content flywheel that actually works 16:46 How a team translates one piece of content across mediums 20:09 What is a "pseudo event" and why do you need one? 24:21 From ghost town to content goldmine 28:47 Expanding your "set" beyond the studio 32:50 The value of "certification" in content creation 34:54 Lessons from Ghost Town Living's organic growth 39:46 How content creation impacts your life and thinking 42:36 Embracing different mediums, no matter your personal preference 45:11 Writing as a lagging indicator of deep work and research 47:53 Why AI can't replace the human touch in deep work 51:38 The process behind "Conspiracy": a narrative nonfiction deep dive 55:08 Parenting for wisdom: cultivating curiosity and deep dives 1:01:11 Navigating demand when starting out 1:05:06 Balancing art and commerce for long-term impact 1:08:52 The freedom of a profitable business 1:11:58 The ongoing challenge of discipline 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 Ryan: Website: https://ryanholiday.net X: https://twitter.com/ryanholiday Instagram: https://www.instagram.com/ryanholiday LinkedIn: https://www.linkedin.com/in/ryanholiday Daily Stoic: https://dailystoic.com The Painted Porch: https://paintedporch.com Featured in this episode: Kit: https://www.kit.com The Painted Porch: https://www.paintedporcom Daily Stoic: https://dailystoic.com Daily Dad: https://dailydad.com Backroad Ventures: https://www.backroad.co Ghost Town Living: https://www.youtube.com/@GhostTownLiving Kit Studios: https://kit.com/studios Highlights: 02:04 - From ads to in-house content creation 07:03 - People finding Ryan through the "algorithm" for free 12:25 - How one experience creates multiple content assets 20:51 - How a tuna recipe went viral for Matthew McConaughey 31:00 - The art of "certification" and making real life content come alive 46:57 - Why physical note cards are crucial for deep work 1:07:56 - Profit as permission to create more art

In this episode, I sit down with Dan Putt, my coach for the last six years, to explore the journey of building a company and the personal transformation that comes with it. We reflect on Kit's growth to over $50 million ARR and discuss the significant shifts in my leadership style, particularly moving from consensus-driven decision-making to confident clarity. Dan and I dive into the importance of identifying and separating reversible from one-way decisions, the power of embracing uncertainty, and the profound impact of connecting with your core "why." Viewers will gain insights into fostering personal growth, navigating leadership challenges, and building a mission-driven company that truly matters. Timestamps: 00:00 Introduction 02:10 Early bootcamp and Kit's growth 04:02 Nathan at 29 vs. now 06:15 Evolution of decision-making 08:20 The "way that works" philosophy 10:15 The difference between right and best decisions 12:10 Coinbase's decision-making framework 14:40 Clarity on decision timelines 16:20 Defining options and decision-makers 21:00 Impact of leadership on results 22:55 Reconciling consensus and decisive leadership 25:30 Building the muscle of making decisions 28:40 Responsibility for positives and negatives 30:10 Taking your seat as a leader 32:45 The clarity of the boundary 35:20 The single-axis fallacy 37:40 The unchanging "why" 43:10 The physics of money and audience 46:00 Equipping people with tools and training 49:00 Recentering on the mission 51:00 Giving work real meaning 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: Website: https://danputt.com LinkedIn: https://www.linkedin.com/in/danputt X: https://twitter.com/danputt Reboot: https://reboot.io Featured in this episode: Kit: https://kit.com Reboot: https://reboot.io Medium: https://medium.com

In this episode, I sit down with Rob Jentsch, an education leader and consultant, to discuss his mission of providing remarkable education to more students globally. We dive deep into his journey from volunteer work in El Salvador to becoming a high school teacher, and then into management consulting, all driven by a desire to improve educational outcomes. Rob shares his current business model, which balances high-ticket consulting with a passion for serving smaller, impactful organizations. We explore strategies for him to scale his impact, build an online presence, productize his services, and optimize his time through a powerful "flywheel" approach, all while maintaining his commitment to his family and personal well-being. Viewers will learn about user-centered design in curriculum, effective strategies for growing an online audience, and how to balance purpose-driven work with business growth. Timestamps: 00:00 Introduction 02:10 Rob's transformational experience 04:09 Obsession with high-quality education access 12:40 Rob's business journey and desire for change 14:40 Shifting from workaholism to more time with family 16:01 Current business revenue and growth 26:40 Productizing services to scale impact 29:27 Standardizing offers and cohort-based learning 32:45 The challenge of onboarding superintendents 36:58 Setting boundaries for optimal impact 41:40 The power of high standards and belief 44:10 Fueling content from client insights 46:12 Choosing LinkedIn as the primary platform 54:15 Creating a feedback loop for content 56:29 The art of reposting successful content 58:30 Promotion strategies: comments, partners, email lists 1:01:05 The virtuous cycle of the flywheel 1:03:00 Iterating and measuring the flywheel 1:05:00 Key takeaways and future plans 1:07:05 The power of sequential skill-building 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 Rob: LinkedIn: https://www.linkedin.com/in/rob-jentsch Website: https://adgneducation.org Featured in this episode: Kit: https://kit.com GrowthTools: http://growthtools.com ADGN Education: https://adgneducation.org

In this episode, I sit down with Bill Burnett & Dave Evans, Stanford Design Professors and best-selling authors, to discuss how they've helped millions rethink their careers and purpose through their "Design Your Life" framework. We dive into the surprising journey developing their best-selling book, the core principles of "design thinking" applied to life, and the critical role of understanding human needs. Later, we get tactical, breaking down their ambitious goal to reach 10 million people with their new book, "How to Live a Meaningful Life," and explore effective strategies for leveraging communities, media, and digital platforms for impactful book promotion. Timestamps: 00:00 Introduction 02:00 Two essential ingredients for a meaningful life 04:23 What we do at Stanford 07:28 Coaching is a trend 10:13 Why plans don't work for life design 12:22 There is more aliveness in you than one life 15:41 From FOMO to JOMO 19:45 How to prototype your life choices 24:00 How to choose when there are too many opportunities 28:28 From Star Wars toys to Apple 32:20 From Mechanical Engineer to Electronic Arts 36:11 Making your life a beautiful experience 39:09 The simplicity of building a meaningful life 42:06 Responding to a deep longing 46:11 Leadership and authenticity 48:41 Goal for the new book 53:23 Lessons from wildly successful books 57:00 Inspirations for book promotion 1:01:46 The flywheel of reviews 1:05:13 Unfair advantages in book promotion 1:10:51 Connecting with students and educators 1:16:30 The power of mass media 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 Follow Bill: LinkedIn: https://www.linkedin.com/in/bill-burnett-4225401 Website: https://designingyour.life Book: https://designingyour.life/how-to-live-a-meaningful-life Instagram: https://www.instagram.com/the.art.shadows Instagram (shared): https://www.instagram.com/fullyalive_bydesign YouTube: https://www.youtube.com/@designingyourlifethebookmo6856 Follow Dave: LinkedIn: https://www.linkedin.com/in/dave-evans-62148 Website: https://designingyour.life Book: https://designingyour.life/how-to-live-a-meaningful-life Instagram (shared): https://www.instagram.com/fullyalive_bydesign YouTube: https://www.youtube.com/@designingyourlifethebookmo6856 Featured in this episode: Kit: https://www.kit.com Designing Your Life: https://designingyour.life How to Live a Meaningful Life: https://designingyourlife.com/how-to-live-a-meaningful-life

In this episode, I sit down with Nicole Burke, founder of Gardenary, to unpack her dynamic strategy for building a 7-figure brand primarily through short-form visual content. Nicole shares exactly how she leverages Instagram to generate millions of views and drive revenue, all while embracing her identity as a business owner who leverages social media, not just an influencer. We dive deep into her content methodology, breaking down the essential categories of reels—entertain, educate, showcase, and invite—and how each contributes to a robust growth and sales funnel. Timestamps: 00:00 Introduction 02:11 Growing a Service Business with Instagram 04:08 Scaling a Garden Design Business 06:26 Transitioning to Digital and Diversifying Revenue 08:24 The Showcasing Strategy: Content Creators & Authenticity 10:04 Breaking Down Gardenary: Education, E-commerce, & Certification 12:57 The Instagram Storefront Analogy 16:26 Leveraging Algorithms: The Share Button's Power 19:07 Educational Content: Answering FAQs & Tracking Saves 22:31 Showcase Content: Inspiring with Results & Aspiration 26:00 The "Invite": Making the Ask Effectively 28:01 The Magic of Automation: From Comments to Conversions 32:26 Free Ad Experimentation with Organic Content 36:20 Crafting Engaging Content: Relatable Pain Points & Humor 41:17 Nicole's Metrics for Content Success 45:10 Instagram's Content Funnel: Reels, Posts, Carousels, Stories 52:19 Stories for Direct Sales & Community Engagement 56:51 Six Types of Videos Anyone Can Make 1:02:13 The Face-to-Camera Hack: Conquering the Fear 1:06:51 The Power of Documentary-Style Video 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 Follow Nicole: Instagram: https://www.instagram.com/heynicoleburke LinkedIn: https://www.linkedin.com/in/nicole-johnsey-burke-136628154 Website: https://heynicoleburke.com Gardenary's Instagram: https://www.instagram.com/gardenaryco Gardenary's Website: https://www.gardenary.com Featured in this episode: Kit: https://www.kit.com Gardenary: https://www.gardenary.com

In this episode, I sit down with Eric Rhodes, DJ and content creator with over 3 million followers, to discuss how to monetize his massive audience beyond traditional events. Eric shares his journey from professional DJ to viral social media sensation and explores the challenges of earning revenue when much of his content features copyrighted music. We brainstorm two main paths for monetization: deepening engagement with music fans, and serving a specific niche of aspiring DJs. We dive into strategies for segmenting his audience, developing high-value lead magnets, and creating educational products like courses or masterminds, all while maintaining control over his time and balancing his passion for DJing with his family life. Timestamps: 01:21 Eric's Social Media Following Breakdown 03:00 The Start of Eric's Online Content Creation 05:07 Key Factors in Eric's Rapid YouTube Growth 08:44 The Importance of Feedback in Content Creation 10:48 Using Negative Feedback for Improvement 13:38 Eric's Current Business Revenue and Breakdown 16:35 The Trade-offs of Reduced Travel and Events 19:40 Segmenting the Audience: Fans vs. DJs 27:07 The "Skill That Makes Money" Framework 32:00 Strategies for Patreon Growth and Fan Engagement 46:17 High-Ticket Offers and Masterminds 54:10 Using Lead Magnets for DJ Audience Growth 01:03:55 The Value of Packaging Knowledge into a Course 01:10:15 Next Steps for Building a DJ Education Business 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 Follow Eric Rhodes: Instagram: https://www.instagram.com/djericrhodes Website: https://theericrhodes.com YouTube: https://www.youtube.com/channel/UCNqLnC4Mc6nGY1ad-aLxxqw TikTok: https://www.tiktok.com/@djericrhodes Featured in this episode: Kit: https://www.kit.com Ampersand Studios: https://ampersandstudios.co Patreon: https://www.patreon.com SitePoint: https://www.sitepoint.com Whisper: https://github.com/openai/whisper ChatGPT: https://chat.openai.com

In this episode, I sit down with Jay Singh, founder of Casper Studios, to explore how AI voice agents are transforming how we create, communicate, and collect information. We dive into how Jay helped Kit’s team automate workflows with voice-based AI, why voice will soon replace typing entirely, and how creators can use tools like Whisper Flow and 11 Labs to turn ideas into finished content faster. Jay also gives a live demo, showing exactly how to build a working AI voice agent from scratch. Timestamps: 00:00 Introduction 01:10 Hitting a $2M run rate with AI implementation 03:34 How Kit’s team uses AI to build internal tools 05:11 Building an automation culture with AI education 06:48 Why voice will replace typing 09:21 The Apple example and how voice got good again 12:16 Why speaking first creates more authentic content 18:52 The power of transcripts as creative building blocks 22:06 Using voice to collect team insights and automate discovery 26:22 Live demo: building a working AI voice agent 33:02 Setting guardrails and testing your AI agent 40:24 How creators can integrate voice feedback loops 47:48 How AI changes human interaction and trust 50:01 Practical next steps for creators using voice 54:15 Final takeaways and what’s next for Casper Studios 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 Follow Jay: LinkedIn: https://www.linkedin.com/in/jaysingh10125 X: https://x.com/JSingh_08 Website: https://casperstudios.xyz Featured in this episode: Casper Studios: https://casperstudios.xyz Kit: https://www.kit.com Eleven Labs: https://elevenlabs.io Wispr Flow: https://wisprflow.ai

In this episode, I sit down with Jessica Miller, business strategist and founder of Jessica Miller Coaching, to uncover four keys that will help you unlock $100K in hidden profit inside your existing business. Jessica shares how to identify the “Hell Yes” offer that energizes you and your audience, simple add-ons and bundles that boost profit instantly, and how to reactivate past clients and turn referrals into a predictable growth system. We also dive into real client examples—from $80-an-hour coaches turning into $30K earners, to brick-and-mortar shops doubling revenue overnight. If you want to find the hidden money already inside your business, this episode is your roadmap. Timestamps: 00:00 Introduction 01:10 Jessica’s journey from pharmacist to business strategist 04:11 Leaving corporate after a health crisis and starting over 06:19 Why so many entrepreneurs struggle with profit 08:21 The key to more profit is doing better, not more 09:17 The first lever: creating your “Hell Yes” offer 13:25 How pricing and positioning change everything 17:16 Client example: the concert pianist who sold $30K in six weeks 21:41 Turning a low-ticket membership into a $120K cohort program 24:26 The second lever: add-ons and bundles 30:29 How tiered pricing can 2–3x your income 34:10 The third lever: reactivation—selling to warm leads again 37:46 The candle bar business that grew 76% year-over-year 43:10 The hidden cost of your energy and how to optimize it 46:54 Capturing contact info to reactivate clients 53:31 The fourth lever: referrals and the “plus one” SOP 59:10 Building referral systems into your business 01:03:00 Measuring results and optimizing every flywheel 01:10:00 Jessica’s worksheet to uncover hidden profit 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 Follow Jessica: Jessica's Free Worksheet : https://jessicamillercoaching.com/nathan Website: https://www.jessicamillercoaching.com Instagram: https://www.instagram.com/jessicadioguardimiller LinkedIn: https://www.linkedin.com/in/jessica-miller-coaching-growth-consultant Featured in this episode: Jessica's Free Worksheet : https://jessicamillercoaching.com/nathan Jessica Miller Coaching: https://www.jessicamillercoaching.com Kit: https://www.kit.com

In this episode, I sit down with Erin Green, founder of Audacious Labs, to break down how to design a course that actually changes behavior. Erin spent 15 years inside agencies building programs for IKEA, Google, and Amazon before developing her framework for turning expertise into transformative learning experiences. We dive deep into what makes most courses flop, how to create real outcomes for students, and how to use AI to design and validate better programs faster. If you’re building a course or product that needs to deliver real results, this episode will show you exactly how to do it. Timestamps: 00:00 Introduction 02:45 Why most courses fail to create results 07:31 The five stages of Hook to Habit: Hook, Start, Build, Flow, Habit 11:22 Creating easy wins to build momentum 14:30 Feedback loops and building confidence 17:57 Flow and skill mastery 24:22 Using behavioral design to make learning stick 31:09 The power of pre-selling and running workshops 35:23 Designing your learning journey backwards 39:55 The importance of bad examples in learning 43:14 Why confidence comes before competence 47:32 Designing opportunities for practice and feedback 56:19 Using AI to organize and refine your ideas 01:04:37 Choosing the right platform and testing small 01:13:00 The biggest mistake course creators make 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 Follow Erin: LinkedIn: https://www.linkedin.com/in/er-green Website: https://www.audaciouslabs.io Featured in this episode: Audacious Labs: https://www.audaciouslabs.io Kit: https://www.kit.com Highlights: 09:12 – Why your competition isn’t other courses, it’s Netflix 14:30 – Building confidence through feedback loops 24:22 – Behavioral design tactics that make learning stick 56:19 – How to use AI to refine and structure your course ideas

In this special episode, I sit down with my friend Frannie Wilson to interview her for my new book "The Ladders of Wealth. We explore her journey of running Ampersand Studios for over 16 years and how she’s reinventing her business after buying out her longtime partner. Instead of having the conversation over a cup of coffee, we decided to record one in the studio instead. We dive into what it takes to scale an agency without burning out, why delegating fulfillment is critical, and how Frannie is using systems, subcontractors, and culture-building to position her team for growth. She shares lessons from managing people, creating replicable offers, and handling the challenges of sales, client retention, and leadership. If you’re navigating the leap from founder-doer to CEO—or building a creative agency that lasts—this episode is packed with insights. Timestamps: 00:00 Introduction 01:15 Frannie’s 16-year journey with Ampersand 04:00 Buying out her business partner and reinventing 07:05 Balancing recurring revenue and one-off projects 10:30 Delegating fulfillment and avoiding bottlenecks 13:55 Building systems and hiring contractors 17:30 The role of values and culture in small teams 22:10 Lessons from managing people and avoiding drama 27:30 Productizing services vs. custom work 33:00 Smarter hiring with test projects 39:30 Landing and qualifying clients the right way 52:30 Retaining clients and handling tough situations 59:45 Final reflections and advice 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 Follow Frannie: Instagram (personal): https://www.instagram.com/frannie_pack LinkedIn: https://www.linkedin.com/in/frannie-wilson Ampersand Studios (Instagram): https://www.instagram.com/ampersand_studios Ampersand Studios (Website): https://ampersand-studios.com Featured in this episode: Ampersand Studios (Instagram): https://www.instagram.com/ampersand_studios Ampersand Studios: https://ampersand-studios.com/

In this episode, I sit down with Lily Jones, founder of Educator Forever, for a coaching session to map out how she can scale her education business from $700K to $1M and beyond. We dive into Lily’s unique flywheel that connects training teachers with agency work, why she’s hitting a growth plateau, and how focusing on sales could unlock her next stage. Lily shares her journey from kindergarten teacher to entrepreneur, what she’s learned building two businesses in one, and how to prioritize growth without burning out. If you’re looking to evolve a multi-offer business without splitting your focus, this episode is a blueprint. Timestamps: 00:00 Introduction 01:17 Lily’s backstory and why she left the classroom 04:43 From teacher to curriculum developer 07:15 How free classes built her first audience 10:26 Creating the Curriculum Development Foundations program 13:19 Building a two-sided business: teachers and agency 16:28 Mapping the Educator Forever flywheel 19:35 Revenue growth 23:05 Where the business plateaued and why 26:31 Increasing project size and repeat contracts 30:56 The case for hiring salespeople 34:20 Finding focus by niching down in K–5 curriculum 38:29 Exploring recurring and higher-paying projects 42:18 Selling into schools as a future growth path 46:55 Balancing opportunities with clear priorities 50:12 Building a long-term roadmap to $1.5M+ 54:46 Takeaways and next steps 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 Follow Lily: Website: https://educatorforever.com Instagram: https://www.instagram.com/educatorforever LinkedIn: https://www.linkedin.com/in/lily-jones-b940457b Featured in this episode: Educator Forever: https://educatorforever.com Educator Forever Agency: https://educatorforeveragency.com Kit: https://www.kit.com

In this episode, I sit down with Kristin Flanary, co-founder of the $1.2M Glaucomflecken brand, for a coaching session on how to scale to $10M by building systems, productized services, and new revenue streams. We dive into Kristin’s unique journey blending healthcare satire, advocacy, and entrepreneurship, and map out how to grow beyond skits and sponsorships into licensing, joint ventures, and an agency model. Kristin shares the challenges of balancing inbound opportunities, managing a lean team, and creating scalable offers that go beyond her and her husband’s personal involvement. If you want to see how to scale a creator business from seven to eight figures without losing focus, this episode is for you. Timestamps: 00:00 Introduction 02:05 Kristin’s backstory: medicine, family, and near-death experiences 05:57 How comedy and satire became a business 07:01 Growing to 1.2M revenue with skits, podcasts, and shows 10:39 The big goal: scaling to $10M 14:01 Breaking down all current revenue streams 17:21 Skits as the foundation of the business 20:59 Building a small but mighty team 22:25 The dream hire: data and analytics 24:22 Exploring licensing and education opportunities 29:15 Managing inbound opportunities and “dreamer” ideas 33:32 The problem with too many projects at once 37:59 Sponsorships, keynotes, and cashflow challenges 43:25 Why a productized service or agency model could scale 48:55 Pricing tiers and the $3K vs $5K agency offer 52:04 How licensing and agency ideas connect 59:10 What the team would need to reach $1M in agency revenue 01:03:29 Recap and key takeaways 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 Follow Kristin & Glaucomflecken: Website: https://glaucomflecken.com Instagram: https://www.instagram.com/ladyglaucomflecken LinkedIn: https://www.linkedin.com/in/ladyglaucomflecken X: https://x.com/lglaucomflecken Podcast: https://glaucomflecken.com/podcast Featured in this episode: Glaucomflecken: https://glaucomflecken.com The Glaucomflecken Podcast: https://glaucomflecken.com/podcast Kit: https://www.kit.com

Creator Flywheels: https://creatorflywheels.com In this episode, I share how creator flywheels can help you get greater results with less effort by turning scattered tasks into systems that compound over time. I break down the three laws of flywheels, how to design them for your business, and examples that took my own projects from stalled growth to unstoppable momentum. I also show how to measure and improve your flywheels with a simple weekly check-in, plus the exact flywheels that scaled Kit, my podcast, and top creators’ newsletters. If you’ve been stuck in chaos or linear processes, this episode will show you the path to compounding growth. Timestamps: 00:00 Introduction 01:00 The three ways of running a business: scattered, linear, flywheel 02:43 The three laws of flywheels: flow, ease, growth 04:37 The Million Subscriber Flywheel (Sahil Bloom case study) 07:29 How sponsorships and reinvestment compound growth 10:02 How to measure flywheels in 15 minutes a week 13:04 The Direct Sales Flywheel that scaled Kit 16:23 Why concierge migrations unlocked growth 17:43 Real-world flywheels and compounding effort 18:21 The Podcast Production Flywheel 20:57 Fixing friction with tools and teleprompters 21:59 The five steps to building your own flywheel 23:40 Enrollment info for Creator Flywheels course 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 Featured in this episode: Creator Flywheels: https://creatorflywheels.com Kit: https://www.kit.com Creator Network: http://creatornetwork.com SparkLoop: https://www.sparkloop.app Sahil Bloom: https://www.sahilbloom.com In this episode, I share how creator flywheels can help you get greater results with less effort by turning scattered tasks into systems that compound over time. I break down the three laws of flywheels, how to design them for your business, and examples that took my own projects from stalled growth to unstoppable momentum. I also show how to measure and improve your flywheels with a simple weekly check-in, plus the exact flywheels that scaled Kit, my podcast, and top creators’ newsletters. If you’ve been stuck in chaos or linear processes, this episode will show you the path to compounding growth. Timestamps: 00:00 Introduction 01:00 The three ways of running a business: scattered, linear, flywheel 02:43 The three laws of flywheels: flow, ease, growth 04:37 The Million Subscriber Flywheel (Sahil Bloom case study) 07:29 How sponsorships and reinvestment compound growth 10:02 How to measure flywheels in 15 minutes a week 13:04 The Direct Sales Flywheel that scaled Kit 16:23 Why concierge migrations unlocked growth 17:43 Real-world flywheels and compounding effort 18:21 The Podcast Production Flywheel 20:57 Fixing friction with tools and teleprompters 21:59 The five steps to building your own flywheel 23:40 Enrollment info for Creator Flywheels course 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 Featured in this episode: Creator Flywheels Course: https://creatorflywheels.com Kit: https://www.kit.com Creator Network: http://creatornetwork.com SparkLoop: https://www.sparkloop.app Sahil Bloom: https://www.sahilbloom.com

In this episode, I sit down with Barrett Brooks, coach to some of the biggest creators in the industry, to break down the five traps that keep creators stuck below one million in revenue and how to avoid each one. We talk about why search and algorithms are shifting, how to stop chasing “greener” business models, and why risk aversion quietly kills momentum. Barrett also shares the patterns he sees working with top creators, how to double down on what’s working without burning out, and the mindset shift every entrepreneur must make to step into true leadership. If you’re feeling stuck on the path to seven figures, this episode is your roadmap. Timestamps: 00:00 Introduction 01:11 Why creators get stuck below $1M 04:43 Betting your business on what used to work 07:44 Search, AI, and the future of traffic 13:28 Believing another business model will be easier 18:55 The grass-is-greener trap explained 27:13 Letting risk aversion kill your momentum 33:49 Playing out the worst-case scenario 40:23 Moving on too fast from what is working 49:43 Building systems vs chasing new ideas 55:25 Hiring without stepping into leadership 01:03:16 How to lean into conflict and feedback 01:07:21 Final thoughts on breaking through 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 Follow Barrett: Podcast: https://goodworkshow.com LinkedIn: https://www.linkedin.com/in/barrettabrooks X: https://twitter.com/barrettabrooks Instagram: https://www.instagram.com/coachbarrettbrooks Website: https://barrettbrooks.com Featured in this episode: Good Work Show: https://goodworkshow.com Barrett Brooks: https://barrettbrooks.com Kit: https://www.kit.com

In this episode, I sit down with Haley from the Kit team, to answer audience questions about building creator businesses, growing newsletters, and scaling software companies. We cover everything from how to find a solo SaaS idea as a non-technical founder, to mapping out a creator business from scratch, to scaling newsletters and identifying blue ocean opportunities. Haley also brings her behind-the-scenes perspective from working with creators at Kit. If you want a practical look at audience growth, business models, and the future of creator tools, this episode has it all. Timestamps: 00:00 Introduction 01:08 Finding SaaS ideas as a non-technical founder 07:36 Mapping out a creator business from scratch 18:25 Building a music career today vs streaming revenue 22:58 The power of storytelling and setting public goals 29:18 Newsletter growth strategies and creator pods 35:54 Identifying blue oceans in crowded markets 41:58 Gathering customer feedback the right way 48:32 Choosing the right early hires in today’s AI-driven world 50:46 Biggest strategic mistakes and lessons learned 01:03:40 Wrap-up and reflections 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 Follow Haley: Instagram: https://www.instagram.com/haleyjani LinkedIn: https://www.linkedin.com/in/haley-janicek X: https://x.com/haleyjanicek Featured in this episode: Kit: https://www.kit.com Creator Network: https://kit.com/creator-network Craft + Commerce: https://kit.com/conference

In this episode, I sit down with Ryan Beck, co-founder of Pray.com, a $30M platform reaching 10M people a month, to talk about his journey from jail at 18 to building one of the most impactful companies in the faith and creator space. We dive into Ryan’s backstory, how he and his co-founders built Pray.com, and the systems churches use that modern creators can learn from. Ryan also shares lessons on building double flywheels, turning sermons into scalable content, and how AI is transforming faith-based media. If you want to understand how to scale community, content, and revenue with timeless principles, this episode is for you. Timestamps: 00:00 Introduction 01:00 Ryan’s journey from jail to a new path 05:15 Studying ministry, computer science, and philosophy 09:20 From nonprofits to launching Pray.com 13:05 How Pray.com scaled to 19M downloads 16:21 The double flywheel model of B2C and B2B 21:29 Pastors as the most prolific content creators 25:15 Derivative content and monetization strategies 29:41 What creators can learn from in-person community 34:10 Dave Ramsey and mission-driven business models 40:12 Evergreen content and repurposing systems 47:00 How Pray.com leverages AI for translation and media 55:10 Building AI Bible and reimagining storytelling 01:00:00 Why email is still the number one channel for creators 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 Follow Ryan: LinkedIn: https://www.linkedin.com/in/purpose Pray.com: https://www.pray.com Featured in this episode: Pray.com: https://www.pray.com AI Bible: https://www.aibible.com Dave Ramsey: https://www.ramseysolutions.com Kit: https://www.kit.com