How Rock Bottom Rebuilt Our Real Estate Business

From Rock Bottom to Real Estate Resilience: Our Story
In this special episode, Annie and I are interviewed on the Real Grit podcast with Neil Timmons, where we open up about our real estate journey—from buying our first rental to losing everything and building it back. We share the raw, behind-the-scenes story of how addiction, foreclosure, and personal breakdowns shaped our business today.

If you’ve ever struggled with staying focused, balancing work and family, or getting back up after failure, this one’s for you. We get real about the lessons, turning points, and mindset shifts that helped us create a sustainable investing business and a life by design.

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Episode Timeline:
[0:00] - Interview intro: From bartending to buying our first home
[1:00] - How we accidentally became landlords—and got hooked
[3:12] - Scaling with lease options and early cash flow goals
[5:05] - Learning real estate from books before the internet
[6:00] - The turning point: DUIs, job loss, and hitting rock bottom
[8:45] - Why getting sober was step one—and how we rebuilt from there
[10:15] - Moving into a destroyed flip to start over
[11:30] - Partnering with a commercial investor to regain momentum
[12:25] - Getting bank qualified again and rebuilding our rental portfolio
[13:33] - Shifting to creative financing and subject-to deals
[14:46] - Helping sellers in distress—because we’ve been there
[16:26] - How we help new investors design a business around their life
[18:09] - From work addiction to work-life balance: what changed
[20:04] - Looking ahead: our plans for flips, Airbnbs, and group coaching
[22:08] - Why we’re expanding our Airbnb strategy in Ohio
[24:00] - Final thoughts on giving back, mindset, and daily commitment

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5 Key Takeaways:
1. Your personal foundation is the root of your business success. Get that right first.
2. Failure isn’t final. We lost everything—and still rebuilt with more purpose.
3. Creative financing and partnerships can unlock big opportunities.
4. Build a business that supports your life—not the other way around.
5. Success requires intention. Design your lifestyle and let your business follow.

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Thanks for listening to this very personal episode. If it spoke to you, please rate and review The Real Estate Ride, share it with a friend, and don’t forget to subscribe. You never know who might need to hear this today.