An old friend called last week with the question everyone asks: "What should I invest in?"

 

He'd come into some money and wanted the inside track. Should he flip houses? Buy an Airbnb? Buy up rentals out-of-state? Which neighborhoods were about to pop and double in the next decade?

 

I told him something I’ve been mulling over, the same thing that's shaped my own real estate game for 25 years and will guide the next 25.

 

"Ask yourself this: In 20 years, what will you kick yourself for not buying?"

 

I wish I'd bought more charming houses in great neighborhoods. 

Because those things went up in value big-time.

 

And I’ve owned it all. Apartments. Airbnbs. Retail buildings. Restaurant buildings. I’ve flipped houses. Heck, I bought a church.

 

But nothing increased in value like my bread-and-butter houses on quiet, tree-lined streets.

 

"But I want cash flow," my friend responded.

 

"Dude, nothing cash flows at first," I told him. "But play this out - you buy three $1.5 million houses over 20 years. By retirement, they're worth $3 million each with $1 million mortgages remaining."

 

"That's $2 million equity per house. Six million bucks total. Add your paid-off primary residence and you're crushing 99% of retirees."

 

"Just buy the nicest houses in the best neighborhoods you can afford."

 

The oldest, dumbest, most bulletproof real estate advice there is.

 

Here's another thing: Pick a dead-simple financial target that actually excites you (besides winning the Powerball).

 

For most people it's some version of: "Paid-off house plus $5 million invested."

 

I told him to focus on that.

 

Honestly, what else do you need?