Re-Define Podcast

In this reflective and honest episode of Re-Define, Will and Eli dig deep into their own journeys to unpack the profound difference between conviction and convincing. They share openly about moments in their personal lives and careers when they found themselves pushing too hard to persuade others, only to realize that true influence and respect come from internal confidence and clarity—what they call conviction.

Will and Eli discuss how tempting it can be to chase after every new opportunity or idea, especially during periods of growth. Yet, they acknowledge that the constant pursuit of external validation or approval often leads to burnout, frustration, and compromised integrity. Through heartfelt storytelling and candid introspection, they explore how shifting their mindset to operate from true internal conviction allowed them to become better leaders, business partners, fathers, and friends.

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.

In this episode of Re-Define, hosts Will Grimes and Eli Schmidt break down what it truly means to have a CEO mindset as a business owner—especially for real estate agents. They challenge agents to move beyond the "transactional mindset" and start thinking like business owners, focusing on branding, systems, delegation, tracking, and scaling. Will and Eli emphasize the power of marketing, automation, and strategic decision-making to ensure long-term success rather than just chasing the next deal. If you're tired of feeling stuck in the daily grind and want to build a sustainable, profitable business, this episode is for you.

🎙️ Topics Discussed:

Why most real estate agents think like employees, not business owners.

The difference between working in the business vs. working on the business.

How personal branding gives agents a competitive edge.

The power of AgentHQ as a centralized system for tracking and nurturing leads.

How to use funnels, retargeting, and automation to generate consistent leads.

Understanding highest and best use of time—stop doing it all yourself.

The importance of coaching and mentorship to accelerate growth.

Why tracking key business metrics is essential for decision-making.

How thinking like a marketer can scale your real estate business.

How successful CEOs prioritize delegation and hiring.

Chapters & Timestamps

[00:00] Intro & Catching Up

[03:30] The "Employee Mindset" vs. The CEO Mindset

[10:45] Why Branding Matters for Real Estate Agents

[17:20] The Power of Systems: How AgentHQ Helps Scale

[25:15] Funnels, Lead Nurturing & Retargeting Explained

[32:40] Tracking Metrics & Business Growth Strategy

[40:10] The Biggest Mistakes Agents Make with Marketing

[48:50] The Role of Coaching & Mentorship in Success

[55:30] How to Delegate & Free Up Your Time

[1:02:00] Final Takeaways & CEO-Level Action Steps