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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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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