AI Summary
5 min readHenry Washington and Dave Meyer have more than two decades of combined real estate experience, and they want you to learn from their failures. "If anybody tells you they've never lost money in real estate, either they're not doing deals, or they're lying to you," Washington says. Meyer adds that the goal is not to avoid mistakes entirely — "you're still gonna screw up" — but to avoid a catastrophic error. The two hosts walk through six specific ways investors fail, each grounded in a mistake one of them has made personally.
Trust no one, verify everything
The number one way to fail, according to Meyer, is "overly trusting other people or random people." He is not saying everyone is untrustworthy. He is saying investors skip due diligence on the people they work with — agents, lenders, contractors — and that has cost him more than any bad deal analysis. "I am not trying to blame other people for my failures. It's my fault. I did not do enough due diligence," Meyer says. Washington agrees: when he was newer, he would take an agent's word on rent comps or after-repair value. Now he interviews multiple agents and calls references before committing. The simplest version of this mistake is accepting the first contractor quote you get. Quotes can vary by tens of thousands of dollars.
Underwrite for the downside, not the upside
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What you'll learn
- 1 (00:00) **Episode Open & Intro** - Henry Washington and Dave Meyer introduce the premise: they'll share their biggest real estate failures so listeners can do the opposite.
- 2 (01:51) **Mistake #1: Overly Trusting Other People** - Dave's top failure is trusting random people without doing due diligence.
- 3 (04:28) **Mistake #2: Calculating Cash Flow the Easy Way** - Henry's top failure is subtracting mortgage from rent and calling it cash flow.
- 4 (13:04) **Mistake #3: Waiting to Talk to Lenders & Agents** - Dave says failing to talk to lenders until you're "ready to buy" is a critical error.
- 5 (15:38) **Mistake #4: Not Getting an Inspection** - Henry warns new investors against skipping inspections.
- 6 (23:36) **Mistake #5: Allowing Deferred Maintenance to Accrue** - Dave says not repairing things properly and letting maintenance pile up is a surefire way to fail.
- 7 (27:40) **Mistake #6: Not Screening Tenants Properly** - Henry's final failure is failing to call tenant references, past landlords, and employers.
+ Full timestamped outline available in the app
Guests on this episode
Show Notes
If you want to generate passive income with rental properties, reach financial freedom, and make the most money with the least stress, do not do any of these six things. There are six ways to fail at real estate investing in 2026, and if you get even a couple of these wrong on your first or next deal, you could be out of the game for years to come. Trust us, we’re now dealing with five-figure emergency costs because we didn't follow the tips we’re sharing today.
Both Henry and Dave have reached financial freedom in around a decade by doing real estate the right way. But that doesn’t mean they haven’t made very costly mistakes. Whether it’s tenants, repairs, using the wrong calculations, or waiting to talk to this specific person, there are a few crucial landmines to avoid on your next investment property.
So, we’re going through the six ways to fail at real estate investing. If you do the opposite of these six, you’ll make money faster, with way less stress, scale smarter, and probably reach financial freedom even quicker than Henry or Dave.
In This Episode We Cover
What Dave does every single time before he hires someone to work on his rental
The one mistake that led to an $80,000 (that’s right) repair bill
The wrong way to calculate “cash flow” that will have you losing money every month
Why most new investors waste months or years by not talking to these two people
Are home inspections really worth it? This is who should (and shouldn’t)
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