Will Grimes on Sacrifice, Leadership, and Building a Bulletproof Mindset | Your Playbook Podcast w/ Alan Gordon

Will Grimes on Sacrifice, Leadership, and Building a Bulletproof Mindset | Your Playbook Podcast w/ Alan Gordon

Author: Will Grimes and Eli Schmidt February 22, 2025 Duration: 52:43

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 a crowded field of get-rich-quick schemes and superficial advice, Real Estate Re-Defined offers a different path. Co-hosts Will Grimes and Eli Schmidt built their own successful practices from the ground up, and they understand the daily grind and strategic decisions that separate a fleeting side hustle from a lasting enterprise. Will, a Marine Corps veteran, applies a disciplined, no-nonsense leadership philosophy to the business, while Eli provides the operational savvy. Together, they move past the industry clichés. You won't find rehashed cold calling scripts or cheerleading for outdated tactics here. Instead, each episode is a deep dive into the practical systems, the necessary mindset shifts, and the adaptable strategies that actually work in the current market. They discuss building a genuine brand, creating efficient workflows that free up your time, and developing the resilience to handle inevitable setbacks. This podcast is for the agent or investor who is tired of the noise and ready to do the real work of constructing a business that thrives long-term, not just survives the next transaction. Listen to Will and Eli for candid conversations, hard-won lessons, and a redefined perspective on what sustainable success in real estate truly requires.
Author: Language: en-us Episodes: 50

Real Estate Re-Defined
Podcast Episodes
172: Make Credit Cool Again w/ Dylan Shively [not-audio_url] [/not-audio_url]

Duration: 1:10:08
Episode Summary In this episode, hosts Will Grimes and Eli Schmidt dive into the world of credit repair with industry expert Dylan Shively. Known for his no-nonsense approach to fixing credit issues, Dylan shares insight…
170: Say No to Grow: The Power of Boundaries in Business [not-audio_url] [/not-audio_url]

Duration: 41:47
In this episode, Will and Eli dive into a conversation about the upcoming "Bulletproof Your Business" event, and touch on strategies for creating a sustainable, resilient real estate business. The hosts also reflect on t…
167: Growing In and Out of Circles: When to Let Go [not-audio_url] [/not-audio_url]

Duration: 1:14:17
In this episode of Day One Dollar Zero, Will Grimes and Eli Schmidt dive into the concept of “circles” — the personal and professional relationships you grow into, grow out of, and protect. They share real-life experienc…
166: How To Win in Real Estate: Your Top 5 Questions Answered [not-audio_url] [/not-audio_url]

Duration: 1:30:24
In this episode, Will Grimes and co-host Eli Schmidt dive into the top five questions they frequently receive from real estate agents. Will leads the discussion with Eli providing his insights and expertise throughout. T…
165: How to Be 40 and Beyond: Insights from Author Noah Dean [not-audio_url] [/not-audio_url]

Duration: 2:03:42
Episode Summary: In this episode, Will Grimes and Eli Schmidt sit down with Noah Dean, author of "It's a Process," to discuss the significance of turning 40, the journey of self-discovery, and the importance of faith and…
164: Brian Davila - Finding Fulfillment Through Faith and Business [not-audio_url] [/not-audio_url]

Duration: 1:18:18
Brian Davila is a Real Estate Investor, Entrepreneur, and partners with Ryan Pineda. In this conversation, Will and Eli discuss Brian's path to entrepreneurship and real estate investing. They talk about Brian's experien…
163: Boxing, Conspiracies, and Spiritual Warfare [not-audio_url] [/not-audio_url]

Duration: 1:20:36
We had some fun in this podcast! With so much going on in the world right now, we wanted to take an episode just to catch up on some of the latest hot topics. We discuss various topics, including the Jake Paul fight, the…