loader from loading.io

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

Money School Podcast

Release Date: 10/16/2025

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 Podcast

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 Podcast

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 Podcast

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 Podcast

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 Podcast

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
Wealthy People Upgrade Everything… Except This w/ Ted Ryce show art Wealthy People Upgrade Everything… Except This w/ Ted Ryce

Money School Podcast

​​As people make more money, they tend to get sharper about almost everything. They think long term, manage risk better, hire experts, invest wisely and optimize their businesses and portfolios. But when it comes to health, a lot of people are still running the same basic playbook everyone else is. Standard labs, five-minute appointments, and just waiting until something breaks. When you want to level up in every area of your life, the conversation shouldn’t be, “Am I sick right now?” It should be, “Where am I headed, and how early can I catch it?” The people who are strong,...

info_outline
“I Can’t Afford a Coach” Is Why You’re Stuck w/ Patrick Engasser show art “I Can’t Afford a Coach” Is Why You’re Stuck w/ Patrick Engasser

Money School Podcast

When you’re struggling in business or just starting out, the last thing you think you need is a coach. You think you can’t afford it, you’re not ready, or you should wait until you have better results first. But every time someone feels like that, that’s actually when they need a coach the most. Most people see coaching as something you do later. Once things are going well, the money is there, and you’ve “made it” enough to deserve help. But that’s not really how it works. Coaching isn’t there to reward you for being successful. It’s there to stop you from wasting years...

info_outline
Putting Your Money in Buckets Is a Trap, Do This Instead w/ Joseph Kovacevic show art Putting Your Money in Buckets Is a Trap, Do This Instead w/ Joseph Kovacevic

Money School Podcast

Most people think financial freedom comes from earning more, saving harder, or finding the perfect investment. But the real trap isn’t income…it’s the way we’re taught to store and move money. We’re told to separate everything into neat little buckets: checking, savings, mortgage, credit cards, investments. And somehow, even when we’re “doing well,” the system still feels tight, slow, and exhausting. The traditional system is wildly inefficient by design. A 3–4% mortgage isn’t really 3–4% at all. It’s closer to 12–15% in simple interest once you account for...

info_outline
How to Stop Leaving Money Inside the Tax Code w/ Zach Newberry show art How to Stop Leaving Money Inside the Tax Code w/ Zach Newberry

Money School Podcast

Most high-income earners assume their tax situation is handled once they hire a CPA and start filing. The return gets done, nothing breaks, and it’s easy to believe that if something mattered, it would already be happening. But that assumption quietly costs people money. Not because they’re reckless or aggressive, but because compliance gets mistaken for strategy, and basic leverage never gets activated. Zach Newberry works with business owners and real estate investors who earn well, and still find themselves on the wrong side of the tax game. What he sees over and over isn’t missed...

info_outline
The Ultimate Investing Advantage Is…Boredom w/ Irwin Boris show art The Ultimate Investing Advantage Is…Boredom w/ Irwin Boris

Money School Podcast

Most investors never question the structure they’re investing in. They accept tight assumptions, back-end-heavy returns, and illiquidity as the price of access, assuming the payout will arrive before anything goes wrong. But when timing slips, liquidity tightens, or markets shift, those assumptions become traps. The deal didn’t fail because the idea was bad. It failed because it never paid the investor enough to wait. Irwin Boris has spent decades operating on the other side of that equation. After more than $5 billion in deal flow, he learned to treat any model that needs to be “screwed...

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!