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Don’t Quit Your Job… Yet. Listen to This First ⏐ Ep. #189

Check out my newsletter at TKOPOD.com and join my new community at TKOwners.com Today I talk about the most controversial question in entrepreneurship: should you quit your job to start a business? It’s something I’ve wrestled with for years, and in this episode I share the frameworks, personal stories, and mindset shifts that have helped me figure out when to go all in and when to hold back. Then I bring on my friend Steven Hale, who actually did it. He walked away from a high-paying job at a publicly traded company and launched Oak Bridge, which went from zero to 25 employees and nearly $6 million in revenue in just one year. We talk about the fear, the clarity, the hard choices, and why sometimes you need your options taken away in order to move forward. If you’re stuck at the edge of the leap, this one’s for you. You can reach out to Steven on LinkedIn or by email at steven@oakbridgeas.com 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://tkopod.co/p-os --- 00:00 The Great Boat Burning Debate 02:46 Understanding the Risks of Entrepreneurship 06:00 Personal Stories of Burning the Boats 08:52 Strategic Planning for Business Success 12:08 The Journey of Stephen Hale 13:20 Navigating Career Transitions 14:47 The Journey to Ownership and Entrepreneurship 16:40 Navigating the Early Days of a Startup 19:16 Balancing Confidence and Insecurity 20:08 The Joy of Building and Creating 24:09 Overcoming Fear and Taking Risks 26:44 Lessons Learned and Moving Forward

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You Don’t Need to Invent New AI Tool. Just Package One Use Case ⏐ Ep. #188

Check out my newsletter at TKOPOD.com and join my new community at TKOwners.com HoldCo Bros are back! In this episode, Nik and I talk about a bunch of AI wrapper ideas you could build today without needing to invent anything new. We talk about using ChatGPT to create personalized trivia games for parents and kids, then turn that into a full-blown business idea, just package it as a niche mobile app. We also brainstorm an AI handyman mentor, where ChatGPT walks you through fixing stuff around the house via voice and video. Later, we go deep on how image generation tools can power things like AI-powered postcards that show homeowners what their house would look like with new paint, windows, or landscaping. All real tools. All working today. You just need to package the use case.  Learn more about Nik here: http://linktr.ee/cofoundersnik Share your ideas with us: Nik@cofounders.com Chris@cofounders.com 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://tkopod.co/p-os --- 00:00 - Highlights 01:00 - Trivia Game Idea with ChatGPT 05:34 - Build a Family Trivia App 07:45 - AI Captures Family Stories 12:27 - HandymanMentors.com Idea 19:37 - DIY Kits for Learning Home Repairs 23:56 - ChatGPT as a Virtual Handyman 28:46 - Free Gifts Hack: Mailing Wedding Invites 31:07 - Personalized Postcards with AI 33:31 - Live Remodel Previews Using AI

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