I Just Lost $25,000: What I Learned from My Worst Real Estate Deal (Ever)

Real Estate Rookie

BiggerPockets

Entrepreneurship, Education, Investing, Business, How To

4.7 • 1.8K Ratings

🗓️ 4 February 2026

⏱️ 50 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Ashley just did her worst real estate deal. Ever. We always talk about the good real estate deals, but what about the bad deals? The rental properties with the nightmare rehabs or the messy evictions? The truth is that the lessons learned from these blunders often propel us toward bigger and better deals. Welcome back to the Real Estate Rookie podcast! Today, we’re going over one of Ashley’s recent deals, where she lost over $25,000. But it could have been even worse. As you’re about to hear, she bit off a little more than she could chew, tackling a new investing strategy with a much more difficult renovation than she signed up for. Ashley shares what went wrong while analyzing the property, the huge mistake she made during the due diligence phase, and how a little indecision snowballed into thousands in holding costs. But most importantly, you’ll learn what Ashley’s taking away from this painful experience so that her next deal is much better for it! In This Episode We Cover Breaking down Ashley’s worst real estate deal ever (and a $25,000 loss!) The critical mistake Ashley made during the due diligence phase Why time is of the essence when taking on a large rehab project Why you should always “test” new strategies, markets, and partnerships The real estate tax benefits that can help offset a “bad” deal on paper And So Much More! Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.biggerpockets.com/blog/rookie-675 Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠advertise@biggerpockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

Click on a timestamp to play from that location

0:00.0	Everyone loves hearing about the deals that worked, the burrs, the home runs, the ones that changed everything.
0:06.4	But nobody talks about the deals that quietly drain your bank account.
0:11.0	So today we're doing the opposite.
0:12.7	We're breaking down deals that we actually lost money on.
0:16.1	And we'll walk through what went wrong, the red flags we missed, and what we'll probably never do again if we were
0:21.4	Rookie investors.
0:27.3	This is the Real Estate Rookie Podcast. I'm Ashley Care. And I'm Tony J. Robinson. And with that,
0:32.3	let's get into the episode for today. So, Tony, I thought today would be a great episode to talk about a deal I just
0:39.5	lost money on. And it's actually the first deal that I have lost money on. And I say this
0:47.0	with some disclaimers, as in I haven't sold a ton of properties, only done four flips, I think, and two were with like a
0:57.0	super experienced investor. So two were really only on my own. So I don't have a larger frame of
1:04.3	properties that I've sold. So maybe, you know, down the road, there will be more losses when I
1:08.7	actually sell a property. But yesterday, I just closed on my first bad deal.
1:15.9	So I thought we could use this as a therapeutic session to talk about the emotional damage,
1:21.1	the financial damage, and the lessons learned moving forward.
1:25.0	Before we jump in, Ash, I just want to frame for the listeners.
1:29.3	Is a deal automatically a bad deal if you lose money on it?
1:34.3	Or is there a scenario where you maybe lose money on a deal, but it's still a good deal?
1:41.3	Just like from a theoretic standpoint, like, you know,
1:44.8	strategic standpoint, do you feel that there's a scenario where you could lose money on a
1:50.2	deal, lose money on a transaction, but in your mind it'd still be qualified as a good deal?
1:57.6	I guess if I got tax benefits from it, maybe, you know, like maybe if I looked at
	...

Please login to see the full transcript.

Previous episode | Next episode

Disclaimer: The podcast and artwork embedded on this page are from BiggerPockets, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of BiggerPockets and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.