My first rental car was a home run. So I bought five more. You can guess how that went.
It started with the family minivan.
We wanted a new van. The old one was worth about $15K. Instead of selling it, I thought, why not rent it out?
So I put it on Turo. If you don't know Turo, it's basically Airbnb for cars. You buy a car, put it on the app, and people rent it short term.
For 20 months, that van netted about $500 a month.
No wrecks. No repairs. Nothing went wrong.
I made money while I had it, and I made money when I sold it.
An absolute home run.
So I did what most investors do after a win.
I thought, this is so easy. Why not buy five more?
Here's what happened to those five cars:
The first one got totaled
The second one got wrecked
The third one's engine blew up
The fourth? Pretty much every bad thing that can happen to a car happened to that car
And the fifth got totaled too
That's the whole point of this post.
Sometimes the worst thing that can happen to you as an investor is that your first deal works.
The slot machine problem
Our mentor Nelson Nash, author of Becoming Your Own Banker, used to say the worst disease someone can have is walking into a casino for the first time, pulling the arm on the slot machine, and hitting the jackpot.
It creates a false sense of reality.
That's exactly what the van did to me. It worked, and I took that good feeling straight into the next five cars.
So here's what I want you to remember:
There's no such thing as good or bad investments. There are only good or bad investors.
First, our September numbers
Every month, Russ and I share our full passive income report in public.
September came in at $66,760 gross and a little under $44,000 net.
Last month we walked you through a short-term rental business that made us $288,000, and why we'd never do it again.
This month is kind of the opposite story: a deal that worked "perfectly" the first time. And that's exactly what led me into trouble.
Three things I want you to walk away with:
1. One win doesn't make a strategy. It's a data point, not a pattern.
2. Most people invest, and when it works, they don't know why. When it doesn't work, they don't know why either.
3. It's not about Turo. Turo is the smallest part of this story. Swap in whatever you've invested in that went well: a rental property, private lending, a syndication.
By the end, you'll know how to tell the difference between guessing and investing.
I tried to do it the "right" way
Russ had already done car rentals with his daughter. By his own admission, they did it the wrong way: managing the rentals themselves in the app, buying new, expensive cars that took big depreciation hits.
I wanted to do it differently.
So I hired someone to manage it. The goal was to be completely hands-off.
Between December 2024 and October 2025, I bought five more cars: two Nissan Sentras, a Hyundai, a Nissan Rogue and an Infiniti QX60.
$48,250 all in. At one point I had six cars on the platform.
Here's how it played out:
First Sentra: totaled in September 2025
Hyundai: the engine blew up. I sold it for about $1,000, basically scrap
Infiniti QX60: my most expensive car at $13,000. Totaled about five months after I bought it
Nissan Rogue: got in a wreck. We repaired it, but by then I could see this wasn't sustainable, so I ended up giving it away as a donation
Second Sentra: the twin sister. Bought for $8,500 at the end of 2024. It made me money the whole time it ran, and then it got totaled too. The insurance paid me $7,300, and that's what got it into the black: about $1,000 ahead
One car out of five came out ahead.
Adding it all up
All in, I put $48,250 into those five cars.
Between rental income, insurance checks and sales, I got back about $35,000.
So I'm down about $13,000.
One home run. Five cars that gave more than half of it back.
Running it through the Golden Filter
Last month we introduced our Golden Filter. Three questions: fit, risk and outcome.
The goal isn't to decide whether Turo is a good or bad deal. It's to decide whether it's a good or bad deal for you.
So let's run it.
Filter #1: Fit
Last month I told you I'm the steady Eddie. I'm the brake pedal. Russ is the gas pedal.
So how does the brake pedal end up with six rental cars?
Honestly, the first one didn't feel like a risk. I already owned the van. If renting it didn't work, I could sell it.
It also felt a lot like when we turned my long-term rental into a short-term rental. That gave me a false sense of confidence that the two were similar.
And once the first car was easy, I stopped asking, "Does this fit me?"
I started asking, "How can I get more of this?"
That's the trap. One win turns off the part of your brain that asks the critical questions.
You stop checking the deal against your buy box, because the deal already proved itself. You don't make it prove itself again every time you buy another car.
Filter #2: Risk
This is where I thought I'd followed my buy box.
I was working with a proven operator. He'd been running Turo for himself at a high level and was already co-hosting a lot of cars. Unlike our short-term rental business, we weren't starting from scratch.
And the first car seemed to prove my assumption.
Then Russ asked me a question I couldn't answer:
Was it the van? Were the people renting it better drivers? Was it the market? Were you lucky? What actually made that first deal work?
Honestly? I couldn't have told you.
I thought it was a proven model. I was betting it would repeat itself.
Then I switched to different cars, and I went five for five on things going wrong. Three totaled, one blown engine, one wreck that ended in giving the car away.
Each car felt like a small bet. $8,000 here. $10,000. Maybe $13,000. No single car was going to sink me.
But the real risk wasn't the price of the car, and it wasn't the operator.
It was the people driving the cars. That's a variable I couldn't control.
And five small bets became a drag on the one deal that actually worked.
Filter #3: Outcome
How many ways could this strategy actually pay off?
One.
Rental income had to beat all the expenses, including depreciation and maintenance.
And what did I own? A car. Which loses value the day you buy it, and loses it even faster when strangers are driving it.
You know how it is when you rent a car.
Last month, in the short-term rental business, all we owned was furniture. This month it's cars.
Same exact lesson.
When a deal has only one way to win, the outcome isn't ideal. We want the things we own to have a chance to pay us along the way. With rental cars, that's just not an option.
Why the first win was so expensive
Here's the crazy part.
If the van had been a disaster, I would have walked away.
Instead it worked. And that's what cost me.
The worst thing that can happen to a guesser is getting it right the very first time. Because now you think you know what you're doing, and you never really did.
The same deal can make one person money and lose another person money. The difference is whether you understand why.
3 questions before you repeat a deal
Before you do a deal again because the last one worked, ask yourself:
1. Do I actually know why it worked? Not a guess. Can I name it?
2. Is that reason going to be true next time? Same price, same market, same operator, same luck?
3. If I do this five more times and it goes wrong, what's the most I can lose, and can I live with it?
If you're thinking about something you've done twice because it worked once, you're not alone.
Most people are guessing. They just don't call it that.
Want to see how close you actually are to financial freedom?
👉 Take the free Financial Freedom Quiz here
If you want to hear Russ grill me through the whole thing, the full video is here.
Next time something works, don't just ask how to do it again. Ask why it worked. If you can't answer that, you're not investing. You're guessing.
Talk soon,
Joey Muré
Wealth Without Wall Street
P.S. This is exactly what we work on inside the Passive Income Lab: know your Investor DNA, build your buy box, and run every deal through your filter before you ever send money. Want to see how it works? Join Russ and me at the free Passive Income Lab Masterclass, Mondays at 8pm ET. Save your seat here
P.P.S. Missed last month's story? Here's the short-term rental deal that made us $288,000, and why we'd never do it again. Read it here
DISCLOSURE: Wealth Without Wall Street provides educational and informational content only and does not provide legal, tax, financial, or investment advice. Any examples or case studies are illustrative and not a promise or guarantee of results. Earnings or income statements (if any) are not typical, and your results will vary based on factors such as your effort, experience, market conditions, and business decisions. You are responsible for your own actions and outcomes.
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