BiggerPockets Real Estate Podcast

Brett Hundley doesn’t want an employer or a nine-to-five job. Ever. At just 32 years old, he has already retired from one career and is now chasing the freedom and flexibility that real estate investing can provide.

During his eight years as an NFL quarterback, Brett spent evenings after practice learning the ins and outs of real estate from teammates who had already discovered its wealth-building potential. Early on, he tried a little of everything—short-term rentals, new construction, and other investing strategies—before zeroing in on house flipping, which has since become his bread and butter.

Brett says the skills he developed running an NFL offense directly translate to the real estate investing world, where he now manages contractors, deadlines, and budgets instead of playbooks. His goal for 2026? Complete 24 real estate projects. But he’s not staying busy just to pass the time post-football. Like most investors, he’s after true financial freedom—not just the income but the flexibility to spend more time with family, travel the world, and retire on his terms.

In This Episode We Cover

Brett’s journey from NFL quarterback to veteran house flipper

How to find “great” deals in competitive markets with strong deal analysis

Quitting the nine-to-five grind and “retiring” with real estate investments

How to build out your own real estate investing team in any market

Completing 24 real estate “projects” per year (without working long hours!)

And So Much More!

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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) pay for one 

The one true way to tell if a tenant will be a great renter or a nightmare 

And So Much More!

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Struggling to find cash flow these days? You’re not the only one. Today’s guest built a portfolio of 50 rental properties before margins started getting thin, but one giant pivot changed everything—a pure cash flow play to complement the appreciation and tax benefits from his rentals. If you want cash flow, he’ll show you exactly where to find it!

Today, Devon Kennard makes 12%-14% returns with an investing strategy that doesn’t involve tenants or toilets: private money lending. Better yet, he’s often able to recycle the same capital multiple times per year for even faster returns. And yes, this is real, passive income. Despite scaling to over $12 million in assets under management (AUM), his tech stack allows him to spend just 25 hours a week on his real estate business.

It sounds too good to be true, but with some capital and a few tools, you could start doing private money deals that give you the monthly income you’re unlikely to find with normal rental properties. Devon shows you how to get started with as little as $10,000 and even breaks down a standard deal where he makes $5,000 in monthly cash flow—plus fees upfront!

In This Episode We Cover

How to generate massive cash flow with private money lending

Why Devon pivoted to passive investing after building a 50-property rental portfolio

How to structure your own private money deals (with as little as $10,000)

The three “levels” of private lending you can start using in 2026

The tech stack that makes private money lending easy for new investors

And So Much More!

Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠h⁠tt⁠ps://www⁠.biggerpockets.com/blog/real-estate-1271.

Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠[email protected]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.
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At 20 years old, Jefferson Simmons was kicked out of his frat house. The entire property was getting remodeled, so he and 47 other college kids needed a place to live. Time to rent…right? After being discouraged by the rentals in his area, he switched his Zillow tab from “Rent” to “Buy” and saw a $250K house for sale.

He was a sophomore in college. Could he really buy his first house?

Thankfully, he had been saving up for tuition since high school, but an academic scholarship now put the entire down payment in his hands. He pitched his parents on cosigning, and next thing you know, he was renovating a basement to fit as many frat friends as possible.

Now, just nine years later, Jefferson is financially free, with a rental portfolio generating $20,000/month in cash flow, all before the age of thirty. Today, Jefferson shares why he ditched law school to invest, the one thing that helped him scale his portfolio way faster, and how he’s consistently found underpriced deals that give him stellar returns. 

In This Episode We Cover

How to buy your first rental, even if you’re young, and even if you have little money

The partnership every new investor should look for to keep growing 

An expensive lesson Jefferson learned on his second real estate deal (huge renovation)

Is dropping out of school worth it to invest in real estate? Why Jefferson did it 

Why you should always make a low offer even if it doesn’t get accepted (at first)

The secret to scaling faster when you want to buy more than one rental per year 

And So Much More!

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This is the worst real estate investing advice I’ve ever heard—and I KEEP hearing it. If you go on to any “real estate investing” TikTok page, they say the same thing: use other people’s money, wait for the crash, interest rates will go down…and that’s not even the worst of the advice.

This type of real estate advice will make investors broke, put them in riskier positions, and stop them from retiring (early) with rental properties. I should know, I became financially free in just over a decade of real estate investing, and I didn’t follow ANY of the advice I’ll mention in today’s episode. 

If you’re about to buy a property with negative cash flow or skip small rentals and go right to the big buildings (multifamily), do not skip this video. Following any of this so-called investing “advice” could push you back ten, twenty, or thirty years from financial freedom, while the rest of the real investors hit their early retirement in just a decade.

In This Episode We Cover

Why you should not buy a “negative cash flow” rental and plan for appreciation 

Buying rentals with none of your own money? Here’s who should and shouldn’t do it

The “passive income” myth that catches many “investors” completely off guard 

Why Dave never quit his job for real estate (and you probably shouldn’t either)

Is BRRRR actually…dead? Why everyone has these “dead” strategies all wrong 

And So Much More!

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