The Money Mondays – "You Deserve to Be Rich" with Rashad Bilal (Earn Your Leisure) – E155

Host: Dan Fleyshman
Guest: Rashad Bilal
Release Date: January 5, 2026
Duration: ~42 min (content 00:05–42:11)

Episode Overview

In this inspiring episode, Dan Fleyshman talks with Rashad Bilal, co-founder of Earn Your Leisure (EYL), bestselling author of "You Deserve to Be Rich," and a leader in business education. They unpack the journey of EYL from its genesis as a hashtag to a multifaceted media, events, and education empire. Rashad shares practical financial advice, entrepreneurial insights, lessons from creating live events, and the importance of giving back—making this essential listening for aspirational businesspeople.

Key Discussion Points & Insights

1. The Origins of Earn Your Leisure and the "You Deserve to Be Rich" Mindset

• Rashad’s Background: Rashad introduces himself as co-founder of EYL, a platform focused on providing accessible business and finance education. (01:38)
• The Book Title’s Significance:
  • Rashad shares that many people sabotage themselves because they don't believe they deserve wealth. He wrote "You Deserve to Be Rich" as a blueprint for personal finance—less about money, more about mindset.
  • Quote: “You can give somebody all of the information … if they don’t deep down believe that they actually are worthy of success, they’re not going to actually go through with it.” (02:34)
• Brand Origin:
  • The phrase "Earn Your Leisure" began as a hashtag Rashad used—at first, reluctantly—before broad adoption inspired the launch of the podcast and ensuing media brand. (06:13)
  • Memorable anecdote: People used the hashtag on vacation photos, and even asked if it was a multi-level marketing company.

2. Scaling Events: From Pop-Ups to Invest Fest

• Early Live Events:
  • Only 16 weeks into EYL, they ran a packed networking event in Carson, CA, which validated their in-person impact. (06:53)
  • Rolled out free events across cities (Brooklyn, Atlanta, Houston, Chicago), each one growing in attendance (from 100 up to 600). (08:03)
• Paid Events and Invest Fest:
  • The first paid event sold 500 tickets—on the day of Kobe Bryant’s death—signifying a model they could replicate.
  • COVID halted plans but attending a Miami event by Marcus (“Him 500”) inspired Invest Fest: a true business “festival,” not just a conference. (10:13)
  • First Invest Fest: About 400–500 people—planned in just eight weeks. (11:20)
  • Steve Harvey Partnership: An EYL interview with Steve Harvey led to him headlining and partnering for Invest Fest, helping expand the fest to 14,000 attendees, and growing further to 25,000 by the latest editions. (12:12)
• 2026 Plans:
  • Ongoing innovation with features like $250,000 pitch competitions, vendor marketplaces (400+ vendors), and expanded programming.
  • “The focus is, how can we make the experience better and better every year … speakers, vendor marketplace, pitch competitions, different value adds.” (13:50)

3. The Value of In-Person Events

• Why Attend?:
  • Networking is the irreplaceable value, building relationships with 25,000 like-minded peers.
  • “If you don’t make at least five very valuable relationships, you’re going about it the wrong way. These relationships can change your life.” (15:09)
  • Inspiration is another key: seeing what’s possible, forging memories, and feeling part of a movement.

4. EYL University vs. Traditional Education

• Structure & Value:
  • EYL University provides not just content, but regional chapters for in-person networking, exclusive classes, and community apps.
  • Designed for people who want hands-on learning and direct access to experts (e.g., free-flow Q&A with Rashad himself).
  • “It’s similar to a public school versus private school... for those that want more community and depth.” (17:36–21:49)

5. Barriers to Wealth: What Holds People Back?

• Scalability:
  • Rashad explains that reaching higher incomes is about scaling yourself, often by changing the vehicle (e.g., industries or business models).
  • Example: Transition from a financial advisor (limited by hours/clients) to leveraging social media/online business to multiply effect and income. (22:02)
  • “Sometimes you have to realize … you might have to look at different avenues to take what you’re passionate about, take your skillset, and scale it.” (24:47)

6. When to Start Investing

• As Soon As Possible:
  • Investing should begin once you have discretionary income—anything above essentials should have a plan.
  • “Anything over what you need to live is all discretionary … and you should put as much of that as you can into investing.” (25:07)

7. Cash Reserves vs. Inflation

• Optimal Savings:
  • Dan’s Rule: Save up to 6–12 months of household expenses; beyond that, excess should be working (inflation will erode parked cash). (26:08)
  • “Every dollar that you’re not investing, you’re losing money on … Because if it’s not growing, then it’s losing.” – Rashad (28:06)

8. How to Choose What to Invest In

• Education Before Investing:
  • Rashad suggests beginning with index funds or dollar cost averaging; some exposure to crypto like Bitcoin is wise.
  • For entrepreneurs: start small, self-funded, and avoid unnecessary debt to ease pressure and allow for smart growth (MVP-first approach). (29:11)

9. The Trap of Lifestyle Creep

• Avoiding Overhead Increase:
  • As income rises, avoid matching it with higher expenses; reflect on money as a tool for wealth-building, not just spending.
  • “Lifestyle creep is a real thing … The more money you make, the more money you spend usually … That’s why most people … they stay broke no matter how much money they make.” (32:09)
  • Encourage thinking of money as “a tool to make more money.”

10. The State of the Podcast & Content Industry

• Platform Mega-Deals:
  • Recent five-year, $200M+ deals signal the power of big shows, but moving content off YouTube (to exclusives) can create barriers.
  • Rashad questions whether audiences will shift behaviors and warns of industry oversaturation:
    • “A lot of people are not original and just copy what’s already been done … It’ll be interesting to see how this plays out.” (37:20)
  • Streaming and attention spans are changing content consumption trends.

11. The Power and Responsibility of Charity

• Why Give Back:
  • “It’s all reciprocal … the more you help, the more you get.”
  • Giving, even at small levels, makes a difference—“Something that doesn’t hurt you and could help somebody, why would you not do it?” (38:54)
  • Taking care of others is a societal good and lessens reliance on institutions like the government.

12. Legacy and Wealth Transfer

• On Leaving Wealth to the Next Generation:
  • Rashad, with only one child now, expects to leave a substantial share but hasn’t fixed a percentage.
  • “You leave money for your family, you leave money to charity … as my sole heir, he’ll probably get a substantial part of it.” (41:19)

Notable Quotes & Memorable Moments

• "Money is a tool ... you need it, you want it, you have to have it." – Dan (00:05)
• "If they don’t deep down believe that they actually are worthy of success, ... they’re not going to actually go through with it." – Rashad (02:34)
• "The relationships can change your life." – Rashad (15:09)
• "The more you help, the more you get." – Rashad (38:54)
• On investing: "Anything over six months savings ... you should invest." (27:44)
• On overhead: "Lifestyle creep is a real thing … You start to rethink your relationship with money." (32:09)

Timestamps for Key Segments

• Intro & Money Mindset: 00:05 – 02:24
• Earn Your Leisure Origin: 02:24 – 06:49
• Live Events & Invest Fest Evolution: 06:49 – 13:50
• Networking Value at Events: 13:55 – 17:36
• EYL University Explained: 17:36 – 21:49
• Scalability & Breaking Income Ceilings: 21:49 – 24:47
• When to Invest: 24:47 – 26:08
• Cash vs. Inflation: 26:08 – 28:43
• Picking Investments: 28:43 – 31:16
• Lifestyle Creep & Wealth Preservation: 31:16 – 34:45
• Podcast Industry Mega-Deals: 34:45 – 38:42
• Charity & Giving Back: 38:42 – 40:55
• Legacy & Wealth Transfer: 40:55 – 41:51
• Rashad’s Socials & Wrap-up: 41:57 – 42:11

Final Thoughts

This episode delivers a dynamic mix of Rashad’s journey, concrete financial advice, and entrepreneurial wisdom. Listeners are left with actionable insights on investing, scaling, building relationships, and giving back, all while being encouraged to break free from limiting beliefs around money and wealth. The chemistry between Dan and Rashad, frank conversations, and real-world anecdotes make this a must-listen for anyone ready to “deserve to be rich.”

Connect with Earn Your Leisure:

• All platforms: @EarnYourLeisure
• Rashad Bilal on Instagram: @RashadBilal

Remember: “Money is a tool to make more money. Change your mindset and your results will follow.”