Podcast Summary:

Earn Your Leisure – "RICH PAUL SAYS NO ATHLETE CAN AFFORD TO FLY PRIVATE ALL THE TIME"
Date: November 19, 2025
Hosts: Rashad Bilal and Troy Millings (with guest Rich Paul)

Episode Overview

This episode dives into the financial realities and mindsets behind the glamorous public images of elite athletes, with Clutch Sports founder Rich Paul offering raw insights into the real economics of sports, wealth, and generational opportunity. Paul debunks myths perpetuated by social media, discusses the importance of financial education and infrastructure, and shares personal experiences guiding athletes beyond their playing careers.

Key Discussion Points & Insights

The Realities of Athlete Wealth & Lifestyle

• Short Career Window:
  • Rich emphasizes that even the highest-earning athletes face a unique set of challenges—most notably, the brevity of their careers.
  • "They're done at 33. Everyone's not going to play to their 40. They're done when they're 33. That money's taxed. You know, they're paying a 55, 51 tax.” (03:57)
• Survivor's Remorse & Obligations:
  • Athletes often feel pressure to provide for extended family and social circles, compounding their financial stress.
  • "For athletes, we all have survivor's remorse, right?...we feel obligated." (03:39)

The Myth of Endless Luxury

• The Private Jet Fallacy:

  • Paul bluntly addresses misconceptions about athlete wealth, specifically the sustainability of flying private.
  • "No athlete can afford to fly private all the time. Yet we see so many athletes on the Instagram flying private. I fly Delta. I cannot afford to fly private. And that's okay with me." (04:37)
  • He clarifies he travels commercially and avoids flaunting the occasional luxury private flight online.
  • "The times I do fly private, you will never see it on Instagram because it's not for show." (08:47)

• Living Within Means:

  • "I'm just trying to get where I'm trying to go to make the money. I'm not trying to spend the money." (08:42)
  • Rich says he's content riding in Comfort Plus on Delta if it means economic responsibility.

Infrastructure, Collaboration, and the Black Wealth Gap

• Building, Not Flexing:
  • Paul stresses the importance of infrastructure, both in personal finance and in community development.
  • "You have to value infrastructure in any business, in anything, whether that's a family infrastructure, whether it's a business infrastructure...you can't scale without the infrastructure." (08:56)
• Breaking Cycles:
  • He reflects on the tendency to compete rather than collaborate among peers from similar backgrounds, which hinders generational progress.
  • "We want to conquer. That's why we're killing each other. We want to conquer. There can only be one king which allows you not to collaborate. If you don't collaborate, then that means we're not communicating. If we're not communicating, then that means we're unable to build what? A community?" (10:03)
• Generational Wealth & Mentorship:
  • Rich advocates for creative financial planning, such as pooling resources and learning from established investors, to plant seeds for future wealth.
  • "Imagine if we had our own fund that we allow him to oversee as well as someone from Blackstone or someone from Apollo or someone from Aries. And then we compounded just 20% of that income. I don't need the whole tree ... I just want a little piece of the bark." (09:40)

Personal Evolution and Humility

• Adapting & Letting Go:
  • Paul reflects on the importance of changing habits and mindsets once achieving success, especially for those from tough backgrounds.
  • "Once I made it out, I can't go back and glorify this, the same things and not give it up, right?" (11:30)
• On Opportunity & Capability:
  • He stresses capability over charity when creating jobs in his circle.
  • "But if you're going to ask me for a job, you also have to be capable of doing the work. I can't give you anything, right? You got to be capable of actually doing it once that opportunity is given. And so it's a two way street." (12:01)
• Managing Life’s Transitions:
  • Rich likens life stages to a car’s transmission—knowing when to accelerate, reverse, park, or go neutral.
  • "Life is all about managing transitions. You have to be able to. That's why a car comes with a transmission. To understand those gears, you got to know when to park, when reverse, when to stay neutral and when to accelerate." (12:35)

Humble Beginnings & Commitment to Growth

• Early Days with LeBron James:
  • Paul recounts his modest salary when working for LeBron and the deliberate choice to become financially independent.
  • "The most money I ever made working for LeBron was $48,000 a year... I was only on his salary for two years. That was since '06... It was important for me to get off of his payroll as fast as I possibly could." (12:56)

Notable Quotes & Memorable Moments

• “No athlete can afford to fly private all the time. Yet we see so many athletes on Instagram flying private. I fly Delta. I cannot afford to fly private. And that's okay with me.”
  (Rich Paul, 04:37)

• “I'm just trying to get where I'm trying to go to make the money. I'm not trying to spend the money.”
  (Rich Paul, 08:42)

• “We've all been in a situation where we had to make decisions. Say, you know what, let me just back up a little bit or let me just park it right here before or if it's going great, let me hit the gas and get to where I'm trying to go.”
  (Rich Paul, 12:40)

• “Once I made it out, I can't go back and glorify this the same things and not give it up, right?”
  (Rich Paul, 11:30)

Important Timestamps

• [03:28] – Financial education and planning conversation begins
• [04:37] – The economics of flying private & athlete spending myths
• [08:42] – Living within your means and humility around flying commercial
• [08:56] – Value of infrastructure in business and family life
• [09:40] – Generational wealth and the need for creative, collective investment
• [10:03] – Cultural pressures, competition vs. collaboration in Black communities
• [12:35] – Life transitions, transmission metaphor
• [12:56] – Story of working for LeBron and the drive for financial independence

Episode Tone & Style

Rich Paul’s delivery is both candid and motivational. The tone is straightforward, with an emphasis on honesty, humility, and actionable wisdom. Both the hosts and guest foster a genuine, no-nonsense dialogue that blends financial literacy with real life lessons from the highest echelons of the sports and business world.

Perfect episode for:
Anyone interested in sports, personal finance, building wealth from humble beginnings, and breaking cycles for future generations.