Real Estate Re-Defined

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

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 five years in a row, Tina is a powerhouse of knowledge and expertise. She shares her top tips and strategies for real estate agents, including how to build a business fueled by referrals, create long-lasting client relationships, and dominate your local market. Whether you're a new agent or a seasoned pro, this episode is packed with actionable insights to help you elevate your game.

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 their candid thoughts on creative processes, the challenges of finding inspiration, and why it's okay to embrace imperfection in pursuit of your goals.

This is the final episode of Day One Dollar Zero.

In this episode, Will Grimes and Eli Schmidt sit down with Austin Hancock, a Marine Corps veteran turned successful real estate investor and performance coach. Austin takes us on his journey from a rebellious youth in Oklahoma to finding discipline in the Marines, and later channeling those lessons into entrepreneurship. He shares raw, unfiltered stories of challenges, triumphs, and the pivotal moments that shaped his career in building luxury homes and transitioning into real estate coaching. This episode is packed with lessons on resilience, leadership, and the power of taking risks to build a better future.

Join us as we explore the trials of transitioning from military to civilian life, the realities of navigating the high-stakes world of custom home building, and how Austin’s no-nonsense approach to self-improvement and business strategy led him to success. Whether you're a veteran, an entrepreneur, or just looking for inspiration, this episode is for you.

Key Takeaways:

Chapter Time Stamps:

Ever wondered if college tuition is negotiable? In this episode of Day One Dollar Zero, we sit down with Kelly O'Connor, founder of College Money Academy, to unravel the complexities of financing a college education. Kelly shares groundbreaking strategies to help families reduce the cost of college, avoid massive debt, and maximize opportunities for their children. From understanding financial aid packages to negotiating tuition rates, this episode is packed with invaluable insights for parents and students alike. Whether you're gearing up for college applications or planning ahead for the future, this is a must-listen!

Timeline

[3:45] - Meet Kelly O’Connor: Background and journey into entrepreneurship.
[15:20] - The pivotal moment: Discovering that college tuition is negotiable.
[22:35] - How financial aid packages really work—and why they’re often lowballed.
[30:50] - The importance of packaging your student for success: Clubs, grades, and leadership.
[42:15] - Breaking down FAFSA and the strategies to reduce your Expected Family Contribution.
[55:00] - How College Money Academy helps families save thousands on tuition.
[1:05:10] - Marketing, webinars, and reaching parents nationwide with the right tools.

Key Takeaways

College Money Academy: collegemoneyacademy.com

In this episode of Day Dollar Zero, Will Grimes and Eli Schmidt sit down with Taylor Cavanaugh, whose life sounds like it's straight from a movie. From serving as a Navy SEAL to joining the French Foreign Legion, Taylor’s journey is filled with incredible highs and humbling lows. The conversation covers everything from the realities of military life to the challenges of starting over after leaving it all behind.

Taylor opens up about the lessons he’s learned along the way, including why mastering the fundamentals is crucial, how to build resilience in the face of adversity, and the power of living with intention. He also shares how he transitioned from elite military units to becoming a performance coach, helping others build structure and self-discipline in their lives. It’s an honest, unfiltered look at grit, growth, and the mindset needed to overcome life’s toughest challenges. This is one episode you won’t want to skip.

Chapters

Website: https://www.taylorcavanaugh.com