loader from loading.io

Why Most Pro Athletes Go Broke (and How Rashad Jones-Jennings Beat the Odds)

Money School Elite

Release Date: 10/16/2025

The Tax Strategy Making Family Offices Rethink Bitcoin w/ Eric Runge show art The Tax Strategy Making Family Offices Rethink Bitcoin w/ Eric Runge

Money School Elite

Most investors think Bitcoin is about price. At the high-net-worth level, a far more important conversation is happening around taxes. Because Bitcoin isn’t treated like a stock or a business. It’s treated as property. And that classification opens up strategies around taxation and capital movement that simply don’t exist in traditional asset classes. And once you understand that, the way you evaluate Bitcoin starts to change. Most high-net-worth investors don’t dismiss Bitcoin because they don’t understand it. They dismiss it because, from where they sit, it doesn’t meet the...

info_outline
Real Wealth Is Built Before the IPO, But You Can’t Access It w/ Mona DeFrawi show art Real Wealth Is Built Before the IPO, But You Can’t Access It w/ Mona DeFrawi

Money School Elite

Most people don’t realize that a large portion of real wealth is created before companies ever reach the public markets. In private companies, early-stage investments, and entrepreneurial ventures, growth happens the fastest. For a long time, that part of the market has been largely inaccessible to retail investors, reserved instead for institutions and high-net-worth individuals. And that has played a significant role in the growing gap in wealth. In this episode of Money School Elite, I sit down with Mona DeFrawi to unpack how this system actually works and what’s starting to change....

info_outline
The Fastest Way to Grow Your Business (It’s Not Strategy) w/ Greg McDaniel show art The Fastest Way to Grow Your Business (It’s Not Strategy) w/ Greg McDaniel

Money School Elite

Most people think success comes from strategy…better marketing, better positioning, better timing. But what if that’s not the lever at all? What if the thing that actually drives growth isn’t what you take, but what you give, freely, consistently, and without any immediate expectation of return? Because when you really look at how businesses grow, how opportunities compound, and how networks form, the pattern isn’t subtle.  The people who seem to “get ahead” aren’t always the smartest or the most tactical. They’re the ones who become connectors, who create value before...

info_outline
Real Estate Investing Isn’t Complicated, You’re Just Doing It Wrong w/ Joel Miller show art Real Estate Investing Isn’t Complicated, You’re Just Doing It Wrong w/ Joel Miller

Money School Elite

Most people don’t associate residential real estate investing with enjoyment. Between tenant issues, maintaining properties, and financing problems, it can really be a headache.  But the problem isn’t the asset class; it’s how you approach it. Because real estate, when done right, is actually one of the most forgiving businesses you can be in. What separates the people who enjoy real estate from the ones who burn out isn’t intelligence or even experience. It’s getting around the right people and getting the right education. What kind of information should you be consuming? How...

info_outline
Smart Money Is Leaving Cash Behind, Here’s Where It’s Going Instead w/ Ben Reinburg show art Smart Money Is Leaving Cash Behind, Here’s Where It’s Going Instead w/ Ben Reinburg

Money School Elite

Most investors believe that holding cash during uncertain markets is the safest move. If you stay liquid, wait for clarity, and avoid risk, you’ll be in a better position when opportunities come… or at least that’s the thinking. But what many high-income earners and investors don’t realize is that cash sitting idle isn’t neutral; it’s losing ground. Between inflation, taxes, and missed opportunities, capital that isn’t deployed is quietly working against you. And while many investors are pulling back, the most sophisticated capital, family offices, institutions, and sovereign...

info_outline
What’s Really Happening In Real Estate Lending Right Now? w/ Jonathan Yoo show art What’s Really Happening In Real Estate Lending Right Now? w/ Jonathan Yoo

Money School Elite

Many real estate investors believe success comes down to one thing: access to capital. If you can borrow money easily, scale quickly, and leverage aggressively, the thinking goes that your portfolio will grow faster. But what a lot of investors are learning right now is that capital alone doesn’t create successful deals. Structure does. In today’s lending environment, small mistakes in leverage, underwriting, or financing strategy can turn what looked like a solid deal into a long-term problem. And many investors don’t realize where those risks actually show up until after the...

info_outline
The End of Traditional Financial Advice? w/ Stefan Astheimer show art The End of Traditional Financial Advice? w/ Stefan Astheimer

Money School Elite

For a long time, truly personalized investment advice has been something only the ultra-wealthy could access. If you have tens of millions of dollars, you can hire advisors who don’t just sell you products. They build strategies around your entire financial life. But everyone else gets standardized portfolios and is told to keep contributing to their retirement accounts and stay the course. That’s starting to change. A new approach to financial advice is emerging, one built around a fee-for-service strategy instead of product sales. Instead of paying someone based on how much money they...

info_outline
What Banks Actually Look For Before Funding a Business w/ Sebastien Boyer show art What Banks Actually Look For Before Funding a Business w/ Sebastien Boyer

Money School Elite

Starting a business is often framed as a simple equation: have a good idea, take it to the bank, and secure the funding. But the reality is very different. Most business owners aren’t rejected because their idea is bad. They’re rejected because they approached the capital the wrong way. So many deals fail before they ever reach underwriting, and it’s not because of the opportunity. It’s preparation, structure, and understanding how lenders evaluate risk. Banks aren’t investors looking for the next big idea. They operate under strict guidelines, regulatory frameworks, and underwriting...

info_outline
The Financial Reality of Pro Snowboarding and How to Escape It w/ Stevie Bell show art The Financial Reality of Pro Snowboarding and How to Escape It w/ Stevie Bell

Money School Elite

Every athlete knows the music will eventually stop. Whether you walk away on your terms, are forced out by injury, or have a contract that doesn’t get renewed, your career will inevitably end. In leagues like the NFL, NBA, or MLB, that ending can still leave you financially set. You might walk away with generational money. In action sports, that’s rarely the case. A pro snowboarder can start earning real money in their teens. They can travel the world, land major sponsors, build a name, and live what looks like a dream career. But very few retire with enough money to last a lifetime. The...

info_outline
The Real Reason AI Valuations Are So High w/ Daniel Nikic show art The Real Reason AI Valuations Are So High w/ Daniel Nikic

Money School Elite

In today’s market, AI valuations are expanding faster than fundamentals can justify. Companies with minimal free cash flow are being priced as if dominance is already secured.  Capital continues to circulate between venture portfolios, strategic partners, and ecosystem incumbents, reinforcing growth narratives that assume liquidity remains abundant. But markets don’t reward narratives forever. When growth slows or capital tightens, the question shifts from projected upside to structural durability. Does the business generate real cash? Does it control proprietary data that compounds...

info_outline
 
More Episodes

From the outside, pro athletes look like they’ve made it; like they’ll never have to worry about money again. Multi-million-dollar contracts, highlight reels, and luxury lifestyles suggest money will never be an issue. 

But behind the scenes, most players are one injury, one bad decision, or one contract away from financial ruin.

The truth is, the average NBA career lasts just 4 years. Taxes, agents, lavish spending, and poor planning chip away at earnings until the fortune is gone, and with no plan for life after the game, many athletes end up broke and starting over from scratch.

But it doesn’t have to be that way. With the right mindset and strategy, those same athletes can turn short-term income into long-term impact. 

That’s exactly what Rashad Jones-Jennings did, proving that reinvention is possible. He built a second career in real estate, transforming his hustle into $60 million of affordable housing developments that are reshaping communities.

Most players never make that leap. They leave the game without financial literacy, without a plan, and without the discipline to turn short-term income into long-term security. The difference isn’t the size of the contract, it’s the ability to shift from consumer to builder, from spending money to multiplying it. 

How did Rashad set himself up for real estate success? What’s the secret to running a thriving development business that also makes a difference?  

In this episode, we unpack the lessons from Rashad’s journey, why most players lose even when they earn millions, and how affordable housing represents one of the most overlooked wealth-building opportunities in today’s market.

 

Things You’ll Learn In This Episode 

-The athlete's money myth
Big contracts shrink fast under taxes, fees, short careers, and lifestyle creep; most players aren’t set for life; they’re set for struggle. How do you design a plan that outlasts the spotlight?

-Affordable housing, unfair edge
While developers chase luxury, demand is starving for well-built, smaller-footprint homes. How did Rashad pre-sell an entire tiny-home community before a single structure went up?

-Operations over hype
Sourcing materials creatively and knowing line-item costs turns vision into profit and investor trust. How do you become an excellent operator in real estate development?

 

Guest Bio

Rashad Jones-Jennings is a retired NBA player, real estate developer, land flipper, and community builder. Transitioning from the world of professional basketball, Rashad is now dedicated to creating attainable housing solutions through the development of luxury tiny home communities. His focus is on providing innovative housing options in our ever-growing economy, creating living spaces anyone can call home. Rashad is passionate about sharing insights and fostering conversations around alternative housing. He also co-hosts a podcast called Big Man Tiny Homes, where he explores the nuances of tiny home living, urban development, and sports. To learn more, visit postprocapital.com

 

About Your Host

From pro-snowboarder to money mogul, Chris Naugle has dedicated his life to being America’s #1 Money Mentor. With a core belief that success is built not by the resources you have, but by how resourceful you can be. Chris has built and owned 19 companies, with his businesses being featured in Forbes, ABC, House Hunters, and his very own HGTV pilot in 2018. He is the founder of The Money School™ and Money Mentor for The Money Multiplier.

His success also includes managing tens of millions of dollars in assets in the financial services and advisory industry and in real estate transactions. As an innovator and visionary in wealth-building and real estate, he empowers entrepreneurs, business owners, and real estate investors with the knowledge of how money works.

Chris is also a nationally recognized speaker, author, and podcast host. He has spoken to and taught over ten thousand Americans, delivering the financial knowledge that fuels lasting freedom.



 

Check out this episode on our website, Apple Podcasts, or Spotify, and don't forget to leave a review if you like what you heard. Your review feeds the algorithm so our show reaches more people. Thank you!