120 Doors & $5M in Debt to 700+ Successful Flips featuring Jimmy Vreeland

In this episode, we sit down with my longtime friend and CG member, Jimmy Vreeland—a guy who’s gone from military grit to entrepreneurial gold. We talk about everything from his time at West Point and deployments overseas, to how a book recommended by his mom ignited a passion for real estate while he was in uniform.

Jimmy shares how he built a multi-market real estate business with multiple verticals, including wholesaling, property management, and education, and the mistakes and wake-up calls he faced along the way. If you’re still working a W-2 job, have a small portfolio, or even running a full-time investment company, this conversation has something for you. We talk real about building wealth, making the leap, growing through masterminds, and building a business that actually supports the life you want.

 

Episode Highlights & Timeline:

[0:00] - Introduction

[1:45] - Jimmy’s business model and how his real estate empire is structured

[4:09] - Early dreams, West Point, and a pivotal decision just before 9/11

[6:52] - The moment his dad dropped the truth about his football dreams

[12:29] - How Rich Dad Poor Dad (and Oprah!) started Jimmy’s real estate journey

[14:55] - Sending money home from deployment to start buying rentals

[16:28] - Transitioning from Army to medical sales during the 2008 crash

[19:22] - What Stryker taught him about sales and mental toughness

[23:04] - The “newborn baby moment” that led to quitting his job

[27:01] - Why “balance” doesn’t exist—and why Jimmy lives on the edge instead

[30:36] - Building culture through the “5 F’s” framework in his business

[34:00] - The evolution of purpose, faith, and business leadership

[45:11] - Discovering mastermind communities and stumbling into CG

[49:04] - The CG wake-up call: 120 rentals, no systems, no real business

[54:03] - The myth of passive income and what really creates financial freedom

[56:30] - The danger of leaving your W-2 too soon

[1:04:44] - How Jimmy implements fast—and why it’s been his secret weapon

[1:08:10] - Being the hero in your family’s story

 

5 Key Takeaways:

1. You don’t need to leave your W-2 to start investing – Jimmy built his first 6 rentals while still deployed overseas and working full time.

2. Passive income is earned through active effort – His 120 rental properties looked great on paper, but they were mismanaged and not profitable until he built real operational systems.

3. Sales experience is a foundational skill – Jimmy’s medical sales career taught him how to get in front of tough clients, ask better questions, and close deals—skills he still uses today.

4. The right community accelerates growth – Joining Collective Genius exposed blind spots, gave him real feedback, and helped him go from operator to owner.

5. Purpose beats profit – Eventually, Jimmy realized that chasing meaning and becoming a hero in his family’s eyes was more motivating than chasing cash flow alone.

 

Links & Resources:

 

• Connect with Jimmy: https://vreeland-capital.com/
• Rich Dad Poor Dad by Robert Kiyosaki: https://a.co/d/3cwQRXy
• The Dream Manager by Matthew Kelly: https://a.co/d/ey8WmBH
• Learn more about Collective Genius: https://thecollectivegenius.com/
•  

If this episode gave you something to think about, helped you reflect on your journey, or lit a fire under you—leave a review, follow the show, and share it with a friend who’s on the edge of their next breakthrough. This is how we grow together.