This is part one of a two-part episode, keep an eye out for part two dropping n ext week . I sat down with Sam Thompson and we went deep on how we're using the new ChatGPT memory update - from self-reflection prompts to turning it into a personal coach and therapist. Sam shared some killer use cases like a CIA-style report on himself and even a custom SWOT analysis . Then we riffed on turning AI-generated images into real businesses . Sam told the story of a viral tweet he had about creating cus...
Apr 16, 2025•38 min•Season 2Ep. 157
I sat down with Shannon Jean , who's built and sold over 10 companies , and we talked all about the art of reselling. He shared how he made $557K net profit selling luxury handbags , and why building systems is the real game—no matter what category you're in. We covered how he connects directly with eBay and Poshmark execs to avoid account issues, how he uses liquidation sites like B-Stock , and why category only matters 30% —the rest is all systems and execution. Shannon also dropped gold on cu...
Apr 14, 2025•36 min•Season 2Ep. 156
HoldCo Bros are back! In this episode, Nik and I talk about the exciting advancements of ChatGPT 4.0 image generation , highlighting its ability to now edit pictures and create incredibly realistic AI images . We brainstormed potential business ideas leveraging this new technology, then we discussed the fundamentals of business success , where Nik introduced his framework emphasizing competitive advantage within idea and execution (grit, distribution, fulfillment, knowledge). We debated the sign...
Apr 11, 2025•38 min•Season 2Ep. 155
The United States is in Trump tariff turmoil , and while everyone's freaking out, I'm seeing opportunity . I don’t care about macroeconomics or politics , but I do care about business ideas . So in this episode, I walk through how to take advantage of what's happening right now. From using tools like Import Yeti and Jungle Scout to find hot products , to becoming a sourcing agent , launching a reverse engineering newsletter , or just figuring out where the next winners are coming from, this mome...
Apr 09, 2025•13 min•Season 2Ep. 154
Use promo code TKOPOD for 20% off Gumloop. I sat down with Max Brodeur-Urbas , founder of Gumloop , and got into all things AI automation . Max described Gumloop as an intuitive drag-and-drop tool where you can build powerful AI workflows without writing a single line of code, think Zapier, but supercharged with AI. We explored how Gumloop isn't just great for automating tasks like web scraping and sales outreach ; it's also a huge opportunity for people looking to start their own businesses or ...
Apr 07, 2025•45 min•Season 2Ep. 153
HoldCo Bros are back! In this episode, Nik and I explore the idea of launching an AI implementation agency to help businesses effectively navigate AI tools . We also dive into the concept of using wearable devices , like the Limitless pendant , for automated medical documentation , potentially replacing scribes. Additionally, we brainstorm various different applications for this technology, including sales coaching, enhancing employee productivity, and more. Learn more about Nik here : http://li...
Apr 04, 2025•32 min•Season 2Ep. 152
Welcome to this solo episode where I'm trying something a little different by going solo and focusing on key business principles that I find to be really important. What I wanted to do differently was explain these ideas through relatable stories and analogies , something I picked up from my teaching days . I share several personal experiences and then break down the business lessons we can take away from them. We talk about the significance of a solid foundation versus just outward appearances ...
Apr 02, 2025•22 min•Season 2Ep. 151
I sat down with Billy Howell to explore his journey into building and selling apps with AI as a self-taught solopreneur. Billy shared how he transitioned from defense consulting into the world of simple app creation. We talked about the power of AI -driven tools like Replit for rapidly creating simple solutions, and his first successful app. He talked about leveraging Upwork to find initial clients and build a freelance business. Billy also touched on his strategy for tackling "shiny object synd...
Mar 31, 2025•39 min•Season 2Ep. 150
HoldCo Bros are back! In this episode, Nik and I talk about the latest in AI and some unique business ideas. We begin by comparing ChatGPT and Perplexity , highlighting the strengths of Perplexity 's deep research function. Our conversation touches on our experiences with custom GPTs and the power of using AI for identifying emerging trends. We also discuss the current reality of AI agents versus more traditional RPA . Later, we explore the idea of leveraging AI to create forward-looking industr...
Mar 28, 2025•28 min•Season 2Ep. 149
Dear diary, here are all the businesses I accidentally started this month. Timestamps below. Enjoy! --- Watch this on YouTube instead here: tkopod.co/p-yt Ask me a question on or off the show here: http://tkopod.co/p-ask Learn more about me: http://tkopod.co/p-cjk Learn about my company: http://tkopod.co/p-cof Follow me on Twitter here: http://tkopod.co/p-x Free weekly business ideas newsletter: http://tkopod.co/p-nl Share this podcast: http://tkopod.co/p-all Scrape small business data: http://t...
Mar 26, 2025•22 min•Season 2Ep. 148
Here's part 2 of my latest conversation with Sam . If you haven't already, go listen to part 1 (Ep. #145) now! I sat down with Sam Thompson again and we talked about a bunch of potential business ideas . We started riffing on how people still pay for simple AI wrappers even though they could use AI themselves, which led us to think about simple AI models like a pay-as-you-go option for deep research . The conversation then bounced to the idea of a super simple ChatGPT-like interface that anyone ...
Mar 24, 2025•30 min•Season 2Ep. 147
HoldCo Bros are back! In this episode, Nik and I, Chris , talk about the power of the middleman business model as a great way to start a low-risk business today. We discuss the core idea of connecting buyers and sellers without dealing with inventory or providing services directly. I share the concept of a "Never Touch Plastic" marketplace , similar to Etsy , but focused on environmentally conscious consumers. We also talk about building an affiliate marketing website for plastic-free products ....
Mar 21, 2025•35 min•Season 2Ep. 146
I sat down with Sam Thompson ( https://x.com/ImSamThompson ), a regular on the podcast, to riff on business ideas , starting with the development of his sourdough GPT wrapper app and how he used AI to build a website for it in a few minutes. We then talk about his marketing plans for his InstantChef GPT wrapper, focusing on leveraging viral content through automation with tools like Zapier and BannerBear. Our conversation touched on copyright concerns when using others' content. I shared my expe...
Mar 19, 2025•36 min•Season 2Ep. 145
I sat down with Jordan Mix , a partner working with Greg Isenberg at Late Checkout , to talk about permissionless projects . We discussed what they are, and Jordan shared the core ideas behind Ryan Holiday's canvas strategy and Jack Butcher's permissionless apprentice philosophy. He shared a few fascinating stories about how undertaking these projects, such as creating custom sneakers and responding creatively to social media posts, led to unexpected opportunities with big names. Jordan explaine...
Mar 17, 2025•50 min•Season 2Ep. 144
HoldCo Bros are back! In this episode, Nik and I talk about the initial stages of starting a business and why founders are so important early on. Nik shares his thoughts on how to grow your business by gradually giving up tasks, always keeping the most important things for yourself . We also discuss some interesting business ideas, like renting out Cybertrucks . This leads to a conversation about creative marketing, specifically using Airdrop in unique ways at different events. Later in the epis...
Mar 14, 2025•37 min•Season 2Ep. 143
Get a free 30 day trial of HighLevel with this link only! https://www.gohighlevel.com/chris-koerner I sat down with HighLevel co-founder Robin Alex ( www.linkedin.com/in/robinalex ) to talk about launching a profitable agency using their all in one platform that is perfect for white labeling , including AI tools , and is very popular with SaaSpreneurs . He explained that it is the ideal platform for anyone who has a business or wants to start an agency, and he detailed exactly how he would do it...
Mar 12, 2025•53 min•Season 2Ep. 142
I sat down with Greg Isenberg to talk about AI, automation, and the tools shaping the future. He started by breaking down his current AI stack - what he’s using, what’s overrated, and what’s actually making him more productive . We talked about the biggest AI business opportunities , how to separate real innovation from hype, and why now is the best time to act on AI trends. Greg also shared his thoughts on the role of design and user experience in AI products and why the way we interact with AI...
Mar 10, 2025•44 min•Season 2Ep. 141
OG Episode that inspired Tyler: B2B Stump Grinding. Cash Cow or Dud? HoldCo Bros are back! In this episode, we feature Tyler ( https://x.com/StumpGuyTy ) , a listener who acted on our B2B stump grinding idea after hearing it on a previous episode, which led him to quit his 9-to-5 job . Tyler shares how he followed our advice word-for-word , testing the concept in Boise before launching in Provo . By implementing our strategies, he achieved impressive results, with $23,000 in September alone . He...
Mar 07, 2025•37 min•Season 2Ep. 140
I sat down with Marc Gaskins ( https://x.com/OvenPusher) of Event Kitchens to discuss his $337k/year event rental business in Charleston, South Carolina. Marc noticed caterers needed quality equipment and turned that opportunity into a thriving business. We explored how a bar fire led to community support, becoming a turning point. We also discussed the value of patient growth versus rapid scaling. Marc explained the unit economics of renting convection ovens , the benefits of a niche focus on c...
Mar 05, 2025•31 min•Season 2Ep. 139
Here's part 2 of my latest conversation with Connor . If you haven't already, go listen to part 1 (Ep. #135) now! I sat down with Connor Gross ( https://x.com/c_gro ), and we discussed whether it's too late to get into e-commerce , launching apps, or YouTube . We talked about AI agents and their potential, like reverse engineering successful YouTube channels or Shopify stores. Connor shared his e-commerce insights for 2025. We debated the future of content creation and the human element , becaus...
Mar 03, 2025•29 min•Season 2Ep. 138
HoldCo Bros are back! In this episode, Nik and I talk about GPT Operator , Nik shares his insights on preparing for AI agents with standard operating procedures , treating them like new employees. I recount building a tool with Replit for a friend, potentially adding seven figures in value. I also share insights from spending seven hours with a West Texas oil billionaire , emphasizing long-term thinking and valuing the thought process over correct answers. Learn more about Nik here : http://link...
Feb 28, 2025•35 min•Season 2Ep. 137
I sat down with Kevin Throop , founder of Toasted Tours , and talked about creating his unconventional tour business. Kevin, formerly at Tesla , wanted to control his destiny, starting with $65,000 and a $3,000 school bus . He renovated the bus for wine tours in Temecula , using a "lipstick on a pig" strategy to make it appealing despite limited funds. Kevin launched with a basic Instagram account, focusing on appealing visuals and honest storytelling. He emphasized customer experience , includi...
Feb 26, 2025•59 min•Season 2Ep. 136
I sat down with podcast regular Connor Gross ( https://x.com/c_gro ), and we talked about practical applications of AI in business . Connor shared the story of an AI program boosting sales by instantly claiming leads in a Slack channel. We considered how executive assistants could dramatically increase their earning potential . I shared my experience running multiple ChatGPT operators , including one finding arbitrage opportunities in used cars. Connor recounted his dad's experience using Claude...
Feb 24, 2025•29 min•Season 2Ep. 135
HoldCo Bros are back! In this episode, Nik and I kick things off with a funny story about going to Raisin Canes while wearing a "Think You Should Leave" t-shirt . Then we talk about the booming Med Spa market , which is really driven by millennials who are both vain and obsessed with their health. Nik and I then discuss how there's potential in integrating Med Spas with golf courses and other membership-based businesses. I share my idea of starting a sauna/cold plunge business inside a gym or co...
Feb 21, 2025•51 min•Season 2Ep. 134
Sign up at HeyRosie .com and use code TKO50 for 50% off your first month I sat down with Jordan Gal ( https://x.com/JordanGal ) about how he built Hey Rosie , an AI voice answering service for small businesses , leveraging AI to provide a better alternative to traditional answering services. Jordan shared how his GPT wrapper addresses the challenges small business owners face with handling phone calls and converting leads, emphasizing focusing on solving customer problems rather than getting cau...
Feb 19, 2025•40 min•Season 2Ep. 133
Get a free 30 day trial of HL with this link only! https://www.gohighlevel.com/chris-koerner I sat down with Sam Thompson ( https://x.com/ImSamThompson ) again, and we talked about AI wrappers and a tweet from Greg Isenberg about DeepSeek and ChatGPT wrappers . We discussed interface loyalty and why user interface is more important than the AI model . Sam shared experiences with Creative OS and integrating into Facebook ad management . We also brainstormed actionable ideas like building a simpli...
Feb 17, 2025•38 min•Season 2Ep. 132
HoldCo Bros are back! In this episode, Nik and I discuss the world of controversial self-help gurus , specifically focusing on Dan Pena . We dissect Pena's background, from his early days in Florida to his claims of a massive oil empire and his now infamous $30,000 mastermind seminars . We analyze his aggressive persona and tactics, while trying to understand what makes him successful. We question the real value of his teachings, including his QLA principles , and if his advice is actually usefu...
Feb 14, 2025•40 min•Season 2Ep. 131
Get a free 30 day trial of HL with this link only! https://www.gohighlevel.com/chris-koerner I'm back with another Q&A episode! I start by sharing viral marketing stunts for an escape room and emphasize finding a "Kirk" for business partnerships. Then, I explain how to grow a local newsletter using Facebook groups and ads , and monetize through AI and high-ticket services. I discuss why premium domain names aren't valuable for crypto and suggest focusing on trending niches, like AI . Finally...
Feb 12, 2025•22 min•Season 2Ep. 130
Get a free 30 day trial of HL with this link only! https://www.gohighlevel.com/chris-koerner I sat down with podcast regular Sam Thompson ( https://x.com/ImSamThompson ), and we talked about how he's planning to launch an AI-powered recipe app using no-code tools and Facebook ads . We discussed his idea to become a free proposal consultant to get into the wedding business . He also shared his views on the importance of understanding business math like CAC and cash conversion cycle . We also touc...
Feb 10, 2025•33 min•Season 2Ep. 129
HoldCo Bros are back! In this episode, Nik and I discuss the world of sales and unexpectedly profitable business models, such as pest control , a field I have personal experience in. We examine how high incomes can be achieved through door-to-door sales , as well as the financial dynamics of the pest control industry. We also discuss the compensation structure of sales crews and the potential of renting out specialized licenses . We explore the idea of pest control as a convenience service rathe...
Feb 07, 2025•27 min•Season 2Ep. 128
