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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!

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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
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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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HoldCo Bros are back! In this episode, Nik and I talk about

Learn more about Nik here: http://linktr.ee/cofoundersnik

Share your ideas with us:

• Nik@cofounders.com
• Chris@cofounders.com

Timestamps below. Enjoy!

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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
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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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I sat down with Sam Thompson again and we talked about how starting a business really isn't that complicated. We broke down why perfect logos, pricing models, or websites don’t matter early on, and how getting on sales calls with nothing to sell is often the best place to begin. We shared an example of a guy who launched a Google Maps optimization service from scratch (no prior experience) and closed clients in under 30 days. We also talked about pricing strategies, paid ads, building confidence through customer conversations, and even how AI tools like Replit and ChatGPT can be packaged into customizable templates and sold as one-time products. If you’ve been thinking about launching something simple but powerful, this idea might be exactly what you need.

You can find Sam on X/Twitter (https://x.com/ImSamThompson) and check out what he’s building at https://www.unlimitedcontent.com/

Timestamps below. Enjoy!

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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 Impatience with Action, Patience with Results
03:02 The Power of First Party Customer Research
06:00 Adapting to Customer Needs
08:55 Understanding Willingness to Pay
11:47 The Importance of Action Over Research
15:05 Pricing Strategies for Success
17:59 Creating Value for Customers
19:58 Navigating Idea Hopping
23:44 Innovative Product Ideas and Market Fit
30:45 Replit Wrapper Idea