Tom Dunkel - Wins, Wipeouts, and Million Dollar Lessons

REL Freedom Podcast

REL Freedom Podcast
Tom Dunkel - Wins, Wipeouts, and Million Dollar Lessons
Apr 02, 2026
Mike Swenson

What does it really take to build an 8-figure business… and survive the crashes along the way? Tom Dunkel is a battle-tested entrepreneur who’s spent nearly 30 years in the trenches of business. He’s built two 8-figure companies, lost six, and raised over $50 million across multiple asset classes. Tom doesn’t just talk about success—he’s lived the full spectrum of wins, setbacks, and hard-earned comebacks. 

Now serving as Managing Director of Eagle Capital, Tom helps investors grow their wealth through operator-backed deals, but his true passion is still building businesses from the ground up. From assembling elite teams to turning chaos into clarity, he brings real-world strategy you won’t find in a textbook. 

We dive into the lessons failure teaches, what separates good operators from great ones, and how to keep pushing forward when things don’t go as planned. Plus, you’ll hear how Tom balances high-stakes business with life outside the office—as a competitive golfer, rock band frontman, and advocate for causes that matter. If you’re an entrepreneur, investor, or someone chasing your next big win, this episode is packed with insights you can actually use.


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Episode Artwork Tom Dunkel - Wins, Wipeouts, and Million Dollar Lessons 34:05 Episode Artwork Jay Conner - Raise Millions Without A Bank 28:29 Episode Artwork Leo Young - Tesla Sales Star to Mobile Home Park Owner 30:08 Episode Artwork Tim Woodbridge - From Scrubs To 25 Mobile Home Parks 33:48 Episode Artwork Alex E Edwards - Mortgage Before Marriage 30:43 Episode Artwork Mike Cobb - The Overseas Escape Plan 32:00 Episode Artwork Ashley Romiti -The Smart Exit: 1031 Exchanges & DST Investing Explained 37:44 Episode Artwork Gil Vaisman - Turning Garages Into Gold 29:16 Episode Artwork John Collins - Buy a Home With $0 Down 28:02 Episode Artwork John Knowlton - From Success To Significance 33:53 Episode Artwork Loodmy Jacques - From Port-au-Prince to Real Estate Powerhouse 34:15 Episode Artwork Michael Russell - Short-Term Rentals, Hostels, and Hotels 36:26 Episode Artwork Mike Swenson - Capital Raising Tips After 250+ Units Closed 28:16 Episode Artwork Kevin Shtofman - How AI Is Powering the One-Person Real Estate Business 28:59 Episode Artwork Cory Long - If AI Can’t Find You, Your Clients Won’t Either 34:27 Episode Artwork Amelia Turbyfill - Luxury, Leadership, and Legacy 30:03 Episode Artwork Erin Krueger - From Solo Agent To Powerhouse Team 31:15 Episode Artwork Matthias Gruenwald - Turning Mobile Home Parks Into Gold 32:12 Episode Artwork Joel Kraut - 7 Steps To Financial Freedom 32:13 Episode Artwork Carlotta Thompson - Ex IRS Auditor Saving Business Owners Millions 30:24 Episode Artwork Tanh Truong - From Pills To Properties: How a Pharmacist Built Financial Freedom 35:22 Episode Artwork Ian Noble - Business Owner Turned RE Investor 34:04 Episode Artwork Mike Swenson - How to Find Your First Investment Property 25:21 Episode Artwork Bonny Wayman - Turning Smart Asset Management Into Wealth 33:48 Episode Artwork Neil Henderson - From W2 To Wealth 38:16