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When To Quit Your Job To Start A Business

35m | Sep 24, 2026

Most creatives with a full time job are stuck on the same question: is it time to leave yet?


Randle Denson jumped the first time as a newlywed. He quit his job, put the financial pressure on his wife, and tried to build a business that wasn't profitable enough to carry them.


Now he's building again, this time while keeping his creative director role, and he's taking a completely different approach.


In this conversation we get into why creatives either jump too soon or jump too late, what it looked like for me to build on the side for nine years before leaving, why a low priced offer made people stop showing up, and the thing most people miss: if your job is actually fulfilling, it gives you the mental freedom to build something on the side instead of the desperation to escape.


If you're working a 9 to 5 and building something after hours, this one is for you.


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