Today's episode features Will Grimes on the "Your Playbook Podcast" with host, Alan Gordon.

In this episode of Your Playbook Podcast, host Alan Gordon sits down with Will Grimes, co-owner of Mile High Property Brothers and leader of Legit Agents, to discuss his journey from military service to entrepreneurship. Will shares his raw and unfiltered insights on resilience, sacrifice, and the realities of building a business from the ground up—literally starting with just $36 in his bank account.

He dives into his early struggles, including selling everything and sleeping in a pantry, to later scaling a multi-million dollar real estate business. Will talks about the discipline he learned in the Marine Corps, the lessons from his short-lived pro baseball career, and how quitting baseball still drives him today. He emphasizes the power of eliminating distractions, staying hyper-focused, and redefining success beyond traditional expectations.

The conversation also touches on fatherhood, coaching real estate agents, and the importance of leading by example in both business and family life. Will provides a no-BS perspective on personal development, decision-making, and why sometimes the hardest part of success is simply getting out of your own way.

If you're an entrepreneur, real estate agent, or just someone looking for motivation to level up in life and business, this episode is packed with valuable insights and tough-love advice from a man who's lived it.

In this episode, Will Grimes and Eli Schmidt take a nostalgic trip down memory lane, reflecting on their personal and professional evolution. From their brand-new podcast set to childhood experiences in music, sports, and the Marine Corps, they explore what it means to be multifaceted in life and business.

The conversation covers topics like breaking stereotypes, embracing diverse interests, and the importance of surrounding yourself with different types of people. They dive into everything from Odyssey of the Mind, marching band, and theater, to how those experiences shaped their ability to navigate the business world today. The episode is packed with humor, personal stories, and unexpected insights—including a hilarious band trip gone wild, reflections on real estate culture, and thoughts on what makes a great leader.

Chapters & Timestamps:

1. (00:00) - New Podcast Set & Evolution

   • Celebrating the new podcast studio and how the show has grown.

2. (05:45) - Breaking Stereotypes & Being Multifaceted

   • The value of having multiple passions beyond surface-level assumptions.

3. (12:30) - Will’s Nerdy Side: Odyssey of the Mind & Music

   • Will’s background in band, Odyssey of the Mind, and his surprising nerdy side.

4. (20:15) - The Wild Side of Band Life

   • A hilarious high school band trip story, drinking on the bus, and band kids being low-key crazy.

5. (30:00) - Leadership & Identity Beyond Titles

   • The difference between titles and true leadership in business.

6. (38:45) - Business Parallels: Real Estate & Fake Prestige

   • The smoke and mirrors of real estate marketing and why authenticity matters.

7. (46:10) - Curiosity & Success: Lessons from Nerds & Outliers

   • Why successful people often have unique backgrounds and deep curiosity.

8. (55:00) - Jiu-Jitsu, Music, & The Value of Different Circles

   • Finding camaraderie in different communities like jiu-jitsu and music.

9. (1:03:30) - The Importance of Adaptability

   • How being exposed to diverse experiences helps in business and life.

10. (1:12:15) - Closing Thoughts & Upcoming Guests

    • Wrapping up with reflections on growth, tattoos, and teasing future guests.