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

EPISODE · Jun 30, 2025 · 28 MIN

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

from The Koerner Office - Business Ideas and Deep Dives with Chris Koerner · host Chris Koerner

Check out my newsletter at TKOPOD.com and join my new community at TKOwners.comToday 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 [email protected] below. Enjoy!---Watch this on YouTube instead here: tkopod.co/p-ytAsk me a question on or off the show here: http://tkopod.co/p-askLearn more about me: http://tkopod.co/p-cjkLearn about my company: http://tkopod.co/p-cofFollow me on Twitter here: http://tkopod.co/p-xFree weekly business ideas newsletter: http://tkopod.co/p-nlShare this podcast: http://tkopod.co/p-allScrape small business data: http://tkopod.co/p-os---00:00 The Great Boat Burning Debate02:46 Understanding the Risks of Entrepreneurship06:00 Personal Stories of Burning the Boats08:52 Strategic Planning for Business Success12:08 The Journey of Stephen Hale13:20 Navigating Career Transitions14:47 The Journey to Ownership and Entrepreneurship16:40 Navigating the Early Days of a Startup19:16 Balancing Confidence and Insecurity20:08 The Joy of Building and Creating24:09 Overcoming Fear and Taking Risks26:44 Lessons Learned and Moving Forward

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

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This episode was published on June 30, 2025.

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