From Corporate to Cash Flow: Real Estate Investing, Passive Income & Fund Strategies with Tom Dunkel

In this episode of the Massive Passive Cashflow Podcast, I sit down with real estate investor and serial entrepreneur Tom Dunkel to unpack nearly 30 years of hard-won lessons in building wealth through strategic investing. From his early days in aerospace mergers and acquisitions to building a $63M distressed mortgage debt business, Tom shares how he transitioned from corporate finance to financial freedom—using real estate as the vehicle.

As the Managing Director of Eagle Capital Investments, Tom has raised over $50 million across four asset classes and helped investors gain access to institutional-quality deals through his innovative fund-of-funds model. A battle-tested entrepreneur, Tom has built two 8-figure companies, failed on six others, and mentored countless entrepreneurs along the way. Outside the boardroom, he's an avid golfer, lead singer in a rock band, and a dedicated philanthropist supporting causes like Tunnels to Towers and a memorial scholarship at William & Mary.

We discuss his fund-of-funds investment model, raising private capital, generating passive income through private lending, and the importance of finding your niche in a competitive real estate market. Tom also opens up about building (and rebuilding) businesses, giving back through charitable causes, and living a life designed around freedom, impact, and purpose. If you're a real estate investor, entrepreneur, or anyone looking to grow smarter and invest wiser, you won’t want to miss this episode.

What You Will Learn:

• How Tom transitioned from aerospace M&A to real estate after being fired in 2006

• The strategy behind his $63M distressed debt business and what made it work

• What went wrong with his earlier business ventures—and what he learned from the failures

• Why finding your niche is critical to building a successful real estate company

• How to structure fund-of-funds deals that benefit both operators and investors

• The importance of education, agility, and building the right team

• How Tom is using his success to give back through music, mentorship, and charitable giving

Links & Resources:

Email:[e-mail]

Phone Number: [phone]

Eagle Capital Investments Website: eaglecapitalinvestments.com

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