Congrats, You Just Made the Worst Financial Decision of Your Life What would you do if your own dad told you your first flip was a total disaster…
Right after you bought the house?
That’s exactly what happened to DJ Dubuono.
But spoiler alert: it turned out to be the start of everything.
In this episode, Kristi Kandel and Erik Stenbakken sit down with DJ—one of our Local Real Estate Developer alums—for a wild ride through live-in flips, family dynamics, bad drywall jobs, and the high-stakes lessons you only learn when the money’s already on the line.
This one’s for the people who are in it for real. No fluff. Just the truth.
What we cover:
Why live-in flips are either genius or insanity (or both)
How DJ’s dad predicted failure—and why he wasn’t entirely wrong
The DIY mistakes that turned into construction wisdom
The importance of managing expectations with contractors
How to document everything (or pay the price later)Scaling up flips and raising capital the real way
DJ’s first-ever sight-unseen deal—and the septic system scareWhat mindset, patience, and pessimism really look like in action
Truth bomb: Nobody cares about your project like you do. So either learn the details—or get ready to pay tuition.
Find us on all major podcast platforms. Search The Real Estate Pessimist New episodes every week.
This isn’t just about real estate. It’s about getting real.
Want to become a STR Expert with Erik’s help? https://eriks-academy.teachable.com/p/str-in-an-hour
Ready to go from podcast listener to Local Developer with Kristi’s guidance?
Whether you're just getting started or ready to go all in, we've got the tools to help you build what matters in your own backyard.
→ Programs & Resources: https://www.localrealestatedeveloper.com/
→ 90-Day Masterclass: https://www.localrealestatedeveloper.com/build-it-course
→ Apply for the Mentorship Program: https://www.localrealestatedeveloper.com/dev-mentorship
#realestatepessimist #liveinflip #firstflipstory #contractorproblems #househackgonewrong #investortruths #realestateeducation #flippinghouses #localdeveloper #realtalkreels #entrepreneurjourney #realestatementorship #truthaboutrealestate
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