DiscoverThe Broke MillionairesE25: From Bartender to 7-Figure Real Estate Investor: How One Man Hustled His Way to the Top | Luke Gilbert
E25: From Bartender to 7-Figure Real Estate Investor: How One Man Hustled His Way to the Top | Luke Gilbert

E25: From Bartender to 7-Figure Real Estate Investor: How One Man Hustled His Way to the Top | Luke Gilbert

Update: 2025-04-16
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🎙 Episode Summary

In this powerful episode, Lauryn and Joshua sit down with Luke W. Gilbert, a real estate investor, agent, and entrepreneur whose journey from digging ditches and bartending in San Francisco to building a 7-figure real estate portfolio is nothing short of remarkable.

Luke opens up about the moment that changed his life, juggling parenthood while broke, reinventing himself as an electrician, and ultimately discovering real estate, land development, and tax strategy as the keys to building long-term wealth.

He also shares the behind-the-scenes truth about:

  • moving his family across states for a better financial future
  • scaling to 9 properties and a 100-door management portfolio
  • making $1.4M in one year and paying $0 in taxes legally through bonus depreciation
  • surviving a nightmare out-of-state rental with slab leaks
  • winning Rookie of the Year his first year as an agent
  • rebuilding his life, marriage, and mindset through sobriety and personal development

This episode is packed with mindset breakthroughs, practical strategies, and real, raw stories about the sacrifices required to build wealth.

🔑 Key Takeaways

1. You’re Not Stuck—You Need New Variables

Luke reveals how leaving San Francisco and later San Diego changed everything. He realized geography was destroying his financial future and making ownership impossible. Once he reframed his situation, opportunities opened. 

2. A Career Reset at 30 Can Still Change Everything

He went from bartending and digging ditches to becoming an electrician simply by calling a contractor every other day until he got hired. Tenacity became his secret weapon. …

3. Real Estate + Tax Strategy = Wealth

After discovering Kiyosaki and tax codes, Luke realized taxes are the #1 enemy of wealth creation. So he became a real estate professional and used bonus depreciation to offset massive income.
He bought seven properties in a year—and paid zero taxes on $1.4M of income

4. The Power (and Pain) of Out-of-State Investing

From Oklahoma to Idaho, Luke shares wins and losses—including a brutal rental with under-slab leaks that cost him over $15k in repairs and crushed his cash flow.
 “It’s not if you lose money in real estate, it’s when.” 

5. Building a Business That Serves Your Family

Luke openly discusses the strain entrepreneurship placed on his marriage and home life—and how he works to balance ambition with being a good husband and father. 

6. Coaching, Sales, and Helping Others Win

Luke is now building a coaching program designed to help real estate agents create predictable income, growth, and tax strategy—because most agents never make it through year one.

🧠 Mindset Moments

  • “What you think is a lot of money… isn’t.”
  • “Leadership is communicating the vision—even when no one else sees it yet.”
  • “Tenacity is my secret sauce.”
  • “You can’t study your way into out-of-state investing—you can only experience it.”
  • “The tax man sees me after depreciation; lenders see me before it.

Book recommendations
The 7 Habits of Highly Effective People: By Stephen R. Covey

Unfair Advantage: The Power of Financial Education: By Robert T. Kiyosaki


Reach out to Luke
Instagram: @luke.w.gilbert

We are looking for guests that have something helpful to share. If you or someone you know could make a good guest on the show, drop us a line to see if it would be a good fit info@thebrokemillionaires.com

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E25: From Bartender to 7-Figure Real Estate Investor: How One Man Hustled His Way to the Top | Luke Gilbert

E25: From Bartender to 7-Figure Real Estate Investor: How One Man Hustled His Way to the Top | Luke Gilbert

Lauryn & Joshua Massari