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The Entrepreneur DNA

The Shadow Side of Entrepreneurship: Stress, Money Shame & Why You’re Already OK | Tim Grimes

5/22/202643 min

Get your FREE copy of Tim's book 'Money, Your Friend' here: https://www.radicalcounselor.com/money-book

In this episode, I sit down with Tim Grimes—radical counselor, somatic coach, and bestselling author of Money, Your Friend—to tackle the side of entrepreneurship nobody puts on their Instagram highlight reel: the internal pressure, money shame, and chronic overthinking that silently sabotage even the most driven business owners. Tim breaks down why so many of us started this journey craving freedom but ended up more stressed than ever, and he shares the daily 10–15 minute practice from his book that helps you get radically honest about what you actually want and why you want it—not the Wolf of Wall Street version, but your truth. We go deep on somatic techniques for releasing stress through the body, the dangerous trap of becoming too passive with self-improvement and manifestation, why comparison culture on social media is making entrepreneurs anxious and broke, and why the real shift happens the moment you stop shaming yourself and accept that you’re already okay right now.

Tim Grimes

Tim Grimes is a radical counselor, somatic coach, and multiple-time bestselling author with over 20 years of experience working at the intersection of stress management, money psychology, and personal transformation. Known for his grounded, no-nonsense approach, Tim specializes in the “shadow side” of entrepreneurship—the internal pressure, fear, and shame that most business coaches don’t talk about. He is the author of Money, Your Friend, Relax More Try Less, and several other books on manifestation and self-improvement. Tim’s work helps entrepreneurs and individuals shift their relationship with money from fear-driven to grounded and calm—without toxic positivity or empty affirmations.

Tim’s Social & Contact Links

Website: https://www.radicalcounselor.com

Coaching: https://www.radicalcounselor.com/radical-change-coaching

Instagram: https://www.instagram.com/radicalcounselor

Email: radicalcounselor@gmail.com

About Justin:

Justin Colby is the host of The Entrepreneur DNA and The M.O.R.E Show podcasts and a best-selling author. He is a serial entrepreneur and a seasoned real estate investor with over 20 years of experience.

Driven by a passion to help entrepreneurs thrive, Justin created the Entrepreneur DNA community to support business owners in building wealth, systems, and long-term freedom. Through his podcasts, books, education platforms, and hands-on mentorship, he continues to help entrepreneurs scale with clarity and confidence.

Connect with Justin:

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Clips

Instagram Gurus Are Lying
Scream-Out Stress Hack
Facing Fear And Shame
Daily 'What Do I Want?'
Grind Vs. Relax Debate

Transcript preview

First 90 seconds

  1. Justin Colby· Host0:00

    What is up, The Entrepreneur DNA family? This is gonna be a good one. I think I say this all the time, but this is, because if you are an entrepreneur, if you're an aspiring entrepreneur, if you're launching or you're in the game fighting the good fight, you're gonna wanna pay attention to my next guest here. As always, these episodes are brought to you by the entrepreneur community. The community is built for you because I bring in guests just like this into the community to help us entrepreneurs not just survive, but to win in the entrepreneur game. So I have a multiple time bestselling author regarding stress management, which we all need some of that, and a radical counselor. Tim Grimes is here. How are you, bud?

  2. Tim Grimes· Guest0:40

    I'm very good, Justin. Thank you for having me.

  3. Justin Colby· Host0:42

    You're very welcome. So listen, I'm excited because, uh, we were joking kinda off-camera here is stress management is such a needed component of our lives. Many people get into the entrepreneur, uh, space, wanna be business owners 'cause they don't... They want-- Well, let me say it this way. They wanna create their own life. They want their own financial freedom. They don't wanna be told how to do it. They don't wanna slave for the man, so they take on the entrepreneur space. And you and I both know it's not for everyone. I believe everyone should do it to some level, but when I talk about stress, it is a lot easier. I always say I wish sometimes I was Tom Cruise on, in the movie "Cocktails," right? Just bartending on the beach where I didn't really have much money to speak of, but- Right ... man, no brains, no headaches,

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