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 You won't find rehashed cold calling scripts or cheerleading for outdated tactics here.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
181: More Than Meets the Eye - Owning Your Unique Journey [not-audio_url] [/not-audio_url]

Duration: 50:06
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, an…
180: Stop Thinking Like an Employee: The CEO Playbook for Agents [not-audio_url] [/not-audio_url]

Duration: 54:45
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 "transa…
179: Secrets Of A Veteran Real Estate Agent - Tina Hare [not-audio_url] [/not-audio_url]

Duration: 2:46:50
In this episode, we welcome back our good friend, Tina Hare, for her second appearance on the podcast! With over 20 years of experience in the real estate industry and a track record as the #1 agent for a major brokerage…
178: Redefining What Success Means to You [not-audio_url] [/not-audio_url]

Duration: 45:57
In this episode of Re-Define, hosts Will Grimes and Eli Schmidt kick off a fresh chapter with engaging discussions on personal growth, navigating busy schedules, and balancing day jobs with passion projects. They share t…
177: Saying Goodbye [not-audio_url] [/not-audio_url]

Duration: 1:15:06
This is the final episode of Day One Dollar Zero.