Earn Your Leisure

40 Episodes
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By: iHeartPodcasts

Welcome to The Earn Your Leisure Podcast. Rashad Bilal and Troy Millings will be your host. Earn Your Leisure will be giving you behind the scenes financial views into the entertainment and sports industries as well as highlighting back stories of entrepreneurs. We will also be breaking down business models and examining the latest trends in finance. Earn Your Leisure is a college business class mixed with pop culture. We blend the two together for a unique and exciting look into the world of business. Let’s go!! #earnyourleisurepodcast

OVERTRADING Is A Guarantee You’ll Stay BROKE
Yesterday at 1:00 PM

More volatility doesn't mean you should take more trades. Learn why the most successful investors are the ones who have the discipline to do less.

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This ONE Rule in Options Trading Saved My Profits
Last Saturday at 4:21 PM

Options Trading Expert Troy Millings reveals the 100% strategy. Don't let market uncertainty steal your victories—learn when to sit on your cash. #hardlyinitiated

 

Subscribe and watch more videos here: https://www.youtube.com/@EarnYourLeisure

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Invest Fest | August 7-9, 2026
Grab early bird tickets now: https://www.investfest.com

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Pinky Cole Breaks Down Filing for Bankruptcy, Losing $100M Business — And Blueprint to Build It Back
Last Thursday at 4:44 PM

00:00 Losing It All Teaser
01:02 Meet Pinky Cole
03:01 Reality TV And Public Scrutiny
05:45 Why Bankruptcy Was Necessary
06:56 Winning The Property Case
09:39 Turning Pain Into Purpose
12:10 Darkest Moment And Comeback
14:53 Money Vs Visibility Engine
16:34 Mental Health And Marriage Strain
21:32 Redefining Success As Peace
23:31 Bankruptcy Explained Simply
28:48 Leadership Changes And Hard Calls
31:03 Final Straw And Filing Decision
34:14 Freedom From Pressure
35:19 Faith Through Darkness
37:07 Toxic Social Media Culture
39:37 Joining RHOA
41:59 Reality TV As Leverage
45:11 Cast Dynamics And Friendships
47:14 Operations Over Popularity
51:16 Hiring The...


Mastering the Art of Fundraising
Last Wednesday at 9:00 PM

In this insightful clip of EYL, hosts Troy Millings and Rashad Bilal sit down with successful entrepreneur and mentor Ryan Breslow to discuss the intricacies of fundraising for startups. Ryan shares invaluable lessons and strategies that have helped him navigate the challenging world of venture capital and investment without falling into common pitfalls. 

Ryan dives deep into his personal journey, recounting initially unsuccessful attempts at raising capital and the crucial advice he received from mentors like Michael Carter of Playco. One of the key takeaways from this conversation is the importance of building relationships rather than simply r...


Trademark Renewal Process: Key Information from Trademark Attorney Rosezena Pierce
Last Wednesday at 1:39 PM

In this enlightening clip of the EYL, join hosts Troy Millings and Rashad Bilal as they sit down with experienced trademark attorney Rosezena Pierce. Dive deep into the world of trademarks and get crucial insights on how to protect your brand effectively. *Episode Highlights:*

*Trademark Renewal:* Rosezena Pierce explains the renewal process and dispels common misconceptions. Unlike annual reports, trademark registrations need to be maintained between the 5th and 6th year anniversary, then the 9th and 10th year anniversary, and every ten years after that. *Scams & Spam:* Learn how to avoid common pitfalls and scams related to trademark...


Is the STOCK MARKET Being Manipulated?
03/30/2026

Financial analyst Ian Dunlap exposes the "worst kept secret" on Wall Street: intentional market manipulation and rigged volatility.

 

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Invest Fest | August 7-9, 2026
Grab early bird tickets now: https://www.investfest.com

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Is NOW the Best Time to Buy Gold?
03/29/2026

Experts discuss why gold remains a top asset in a volatile market. Learn why its value transcends thousands of years. #marketmondays

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Join the EYL community for deeper training and a more detailed approach:
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https://www.ianinvest.com

Invest Fest | August 7-9, 2026
Grab early bird tickets now: https://www.investfest.com

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TSA Shutdown Wasn’t About Money… It Was About Control
03/28/2026

"TSA crisis" is being utilized as an opportunity to normalize a militarized presence in public spaces, ultimately aiming for greater societal control rather than genuine security or financial efficiency.

Subscribe and watch more videos here: https://www.youtube.com/@EarnYourLeisure

Join the EYL community for deeper training and a more detailed approach:
https://www.eyluniversity.com

Join the number one stock club in the world:
https://www.ianinvest.com

Invest Fest | August 7-9, 2026
Grab early bird tickets now: https://www.investfest.com

See omnystudio.com/listener...


Why Selling Isn’t “Selling Out” | Richelieu Dennis on Essence Fest Fallout & Black Business Issues
03/26/2026

00:00 Fear of Selling Out
01:09 Meet Rich Dennis
04:40 SheaMoisture Origin Story
06:41 Family Business Rules
08:33 From Harlem Table to Retail
12:37 Building the Right Team
15:00 Impact Supply Chain in Africa
17:32 Backlash and Exit Strategy
26:36 Generational Wealth Reality
30:50 Capital Talent and Competition
36:53 Grace and Community Support
44:09 Why Big Brands Get a Pass
47:39 Economic Pressure Builds
49:43 Entrepreneurship at Risk
51:18 Unemployment Gap Explained
53:07 Capital Over Credentials
55:41 Losing Cultural Institutions
58:03 EssenceFest Backlash Lessons
59:51 Festival Pillars and Vision
01:03:45 Teyana Taylor Curator Role
01:04:22 Future of Media and Wealth<...


How to Perfect Your Elevator Pitch
03/25/2026

Welcome back to EYL! In this clip, we are joined by the incredible Ashaala Shanae, who provides invaluable insights on how to perfect your elevator pitch. Whether you're preparing for Invest Fest or any other pitch scenario, this video is packed with actionable advice to help you stand out and make a lasting impression.

*Key Points Discussed:*

1. *Clear and Concise Messaging:*
   Rashad Bilal kicks off the conversation by emphasizing the importance of a clear and concise message. Knowing who you are, what you do, who you serve, and what you offer is crucial.

...


Understanding Real Estate Markets: Capitalize on Down Commercial Real Estate Markets
03/24/2026

Welcome back to another insightful clip of Market Mondays! In this clip, hosts Troy Millings, Ian Dunlap, and Rashad Bilal sit down with veteran real estate mogul Don Peebles to discuss the current state of the commercial real estate market and strategies to thrive during downturns.

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I Don't Trust Any Jewelers" Here's Why
03/23/2026

In this thought-provoking clip from "Black Out with Ian & Rashad," Rashad Bilal, Ian Dunlap, dissect the long-held beliefs around diamonds, wealth, and traditions. The conversation kicks off with Rashad Bilal questioning the true value—and marketing scam—behind diamonds, revealing how their perceived worth was crafted through strategic advertising and artificial scarcity over the past century. Ian Dunlap then expands on the idea, pointing out how diamond prices have plummeted in the past decade and highlighting how the story of diamonds as a "girl's best friend" is more marketing myth than real value. Dive deeper as Rashad Bilal uncovers the...


Are College Degrees are a Becoming Worthless?
03/22/2026

The era of "go to school, get a job" is officially over. With AI looming and 30% of grads facing unemployment, the traditional education system has become a debt-fueled Ponzi scheme.

Subscribe and watch more videos here:    / @earnyourleisure  

Join the EYL community for deeper training and a more detailed approach: https://www.eyluniversity.com

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Invest Fest | August 7-9, 2026 Grab early bird tickets now: https://www.investfest.com

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Stop Chasing Volatility Before You Get LIQUIDATED
03/21/2026

If you aren't putting in 8–10 hours a day on the charts, you shouldn't be chasing market ramps. Ian breaks down why "safety" is the best play for 90% of investors right now.

 

Subscribe and watch more videos here: 

 / @earnyourleisure  

 

Join the EYL community for deeper training and a more detailed approach:

https://www.eyluniversity.com

 

Join the number one stock club in the world:

https://www.ianinvest.com

 

Invest Fest | August 7-9, 2026

Grab early bird tickets now: https...


AI Is Coming For Your Job… Everyone Will Be Forced To Become Entrepreneurs (w/ Sinéad Bovell)
03/19/2026

The future isn’t coming… it’s already here. In this episode of Earn Your Leisure, we sit down with AI expert Sinéad Bovell to break down what’s really happening in the world of artificial intelligence—and what it means for your future, your career, and your money. From the rise of OpenAI and the mass adoption of AI in 2022, to predictions that white-collar jobs could be automated by 2028, this conversation goes deep into how fast the landscape is shifting and why most people are underestimating it.

Sinéad shares her journey into becoming an AI expert, i...


The GENIUS Clause in Allen Iverson’s Lifetime Reebok Deal
03/18/2026

Allen Iverson’s lifetime contract with Reebok is one of the smartest business moves in sports history. Find out how his "Deferred Income Annuity" secures his future with a massive $32M payout.

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7 Warning Signs the Economy is WEAKENING Right Now
03/17/2026

From skyrocketing credit card debt to a freezing housing market, we dive into the 7 data points showing the true state of the US economy. Is a major correction inevitable?

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How Yo Gotti Almost Lost EVERYTHING to the IRS
03/16/2026

Yo Gotti opens up about the massive financial wake-up call that nearly cost him 15 properties. Learn why he didn't pay taxes for 5 years and how he finally fixed his real estate portfolio.

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Why the Market CRASHES Every February (And How to Profit)
03/15/2026

History repeats itself. Discover the seasonal cycle that causes the stock market to dip every February and March, and how smart investors use this "pre-season" to build generational wealth.

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4 Stocks That Are Actually WAR-PROOF
03/14/2026

Market volatility is rising, but these 4 "all-weather" stocks are designed to survive global conflict and economic crashes. We break down the ultimate defensive portfolio for uncertain times.

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Mr. Tendernism Breaks Silence On Going Independent, No Equity & Fight For The “Tendernism” Trademark
03/12/2026

Mr. Tendernism sits down wMrTendernism #BBQ #Entrepreneurship #FoodCulture #BlackEntrepreneurs #Pitmaster #Tendernisments on the internet. With over 50 years dedicated to mastering barbecue, Walter Johnson explains how his passion for the culinary arts turned him into a world-renowned pitmaster and the face of “Tendernism.”

In this conversation, Mr. Tendernism breaks down his journey traveling to all 50 states to perfect his craft, the origin of the word “Tendernism,” and how he developed the signature seasoning and technique that made his food legendary. He also discusses going viral on social media, learning the internet in real time, and how the unexpected visit fr...


How to Buy a House with ZERO Credit or Down Payment
03/11/2026

The NACA program is the best-kept secret in real estate, but most people quit before they finish. We go behind the scenes on the "rigorous" process, the mindset you need to survive the paperwork, and how to finally own property without the traditional bank hurdles.

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Join the EYL community for deeper training and a more detailed approach:
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Invest Fest | August 7-9, 2026<...


Why Netflix Refused a $110B Deal (And Why It Was GENIUS)
03/10/2026

In a world of massive media mergers, Netflix just made a shocking power move by walking away from Warner Bros. We dive into the debt, the politics of Larry Ellison, and why "saying no" might be the best investment Netflix ever made.

 

Subscribe and watch more videos here: https://www.youtube.com/@EarnYourLeisure

Join the EYL community for deeper training and a more detailed approach:
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Join the number one stock club in the world:
https://www.ianinvest.com

Invest Fest | August 7-9, 2026
G...


4 Recession-Proof Stocks That Are Totally AI-PROOF
03/09/2026

Everyone is chasing the AI hype, but what happens if the bubble bursts? We identify 4 "Consumer Staple" powerhouses like Walmart and Caterpillar that dominate their niche and remain safe from AI disruption for the next 20 years.

 

Subscribe and watch more videos here: https://www.youtube.com/@EarnYourLeisure

Join the EYL community for deeper training and a more detailed approach:
https://www.eyluniversity.com

Join the number one stock club in the world:
https://www.ianinvest.com

Invest Fest | August 7-9, 2026
Grab early bird tickets now: https://w...


Warning: This Oil Price Trigger Will CRASH The Market
03/08/2026

History repeats itself. From the 1973 embargo to the 2008 recession, oil has always been the ultimate economic indicator. We discuss why $93.50 is the "danger zone" that could wipe out corporate earnings and trigger a massive pullback.

Subscribe and watch more videos here: https://www.youtube.com/@EarnYourLeisure

Join the EYL community for deeper training and a more detailed approach:
https://www.eyluniversity.com

Join the number one stock club in the world:
https://www.ianinvest.com

Invest Fest | August 7-9, 2026
Grab early bird tickets now: https://www.investfest.com<...


3 Signs A Stock Is About To 10X
03/07/2026

Are you looking for the next Nvidia or Apple? We break down the 3 specific metrics—including the "Mote" and high inside ownership—that signal a stock is ready to 10X your portfolio in the next 5 years.

Subscribe and watch more videos here: https://www.youtube.com/@EarnYourLeisure

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Invest Fest | August 7-9, 2026
Grab early bird tickets now: https://www.investfest.com<...


2 Chainz on Biggest Wins & Losses, Million-Dollar Independent Grind & SpaceX Investment
03/06/2026

In this episode of Earn Your Leisure, we sit down with 2 Chainz for a powerful conversation about music, business, and building real leverage. He reflects on why now was the right time to write his new book, the power of trusting your intuition, and how his mother’s real estate career helped shape his mindset around ownership and investing.

 

2 Chainz also shares key lessons from his journey in the music industry, including making his first million on the Chitlin Circuit, buying himself out of a contract with $100K in a shoebox, structuring his record deal lik...


The Alarming TRUTH About The US Debt Spiral
03/04/2026

Subscribe and watch more videos here: https://www.youtube.com/@EarnYourLeisure Join the EYL community for deeper training and a more detailed approach: https://www.eyluniversity.com Join the number one stock club in the world: https://www.ianinvest.com Invest Fest | August 7-9, 2026 Grab early bird tickets now: https://www.investfest.com

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Mary J. Blige on Tax Issues, Strength of a Woman, Divorce, Paying Alimony, Acting, Music & Business
03/02/2026

Join us as Mary J. BlMaryJBlige #StrengthOfAWomanarkable journey! She candidly discusses her past struggle with a staggering $100 million IRS debt and the invaluable lessons it taught her. She sheds light on the exhilarating, yet challenging world of her acting and music careers, while explaining why a Verzuz isn't on her agenda. 

Listen to her unique perspective on paying a hefty $30,000 a month in alimony to her ex-husband. Mary also introduces us to her empowering project – a music festival titled 'Strength of a Woman'. She gives us a peek into her relationship with music mogul Diddy, her stance on...


5 Ways To Get RICH In This Market
03/02/2026

They close with Rashad's add-on: you need money to invest, so prioritize earning more, avoid debt traps, and have the discipline to stash/invest consistently, especially because inflation and rising costs make investing feel “mandatory,” not optional.

 

Subscribe and watch more videos here: https://www.youtube.com/@EarnYourLeisure

Join the EYL community for deeper training and a more detailed approach:
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Join the number one stock club in the world:
https://www.ianinvest.com

Invest Fest | August 7-9, 2026
Grab early bird tickets now: https...


The 300 Trade Rule Why You MUST Practice Before Going Live!
02/28/2026

This trading tip is about leveling up the right way: size up only after you have earned it through reps and time in the market, but never change your risk profile. The key is to keep your stop losses, targets, and discipline the same as you scale from 1–3 contracts into larger size, so you can actually benefit from big moves without getting sloppy after wins or emotional after losses. Practice relentlessly (hundreds of quality trades), then graduate in stages, staying conservative and consistent so you can stay in the game long enough to win big.

 

Sub...


Sold a Company for $75M & Didn’t Get Paid 🤯 The Business Secrets They Don’t Tell Entrepreneurs
02/26/2026

This week on Earn Your Leisure, Jeff Frommer shares the real story behind building and selling his $75 million podcast production company — and why big exit headlines don’t always tell the full story. He opens up about waiting on $65 million in stock from the deal, the dark side of acquisitions, and why pushing for cash can protect your future.

 

We also break down why trust is the ultimate currency in business, when creators should negotiate equity, and why ownership is still the real American Dream. Plus, Jeff explains the vision behind Owm.ai and how it’s...


Are Cheap Stocks All SCAMS?
02/24/2026

Should you buy stocks under $20? We break down why most cheap stocks are cheap for a reason, what actually matters (volume, fundamentals, moat), and why focusing on 4 to 6 great companies beats chasing “the next 20 to 200” story.

 

Subscribe and watch more videos here: https://www.youtube.com/@EarnYourLeisure

Join the EYL community for deeper training and a more detailed approach:
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Join the number one stock club in the world:
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Invest Fest | August 7-9, 2026
Grab early bird tickets now: https://www.i...


When To Sell a Stock
02/23/2026

Sell a long term position when one of these is true:

 

You already hit your “freedom number.” If the goal is reached and you are locking in lifestyle security, reducing risk, or shifting into more stable assets, selling can make sense.

The fundamentals broke, not just the price. Revenue model changes, margins deteriorate, leadership issues, regulation, or the company loses its edge. If the business is no longer what you originally bought, it is not a “hold,” it is a new decision.

They lost their moat and fell out of the top tier...


3 Stocks Set to EXPLODE in 5 Years
02/22/2026

They debate “top 3 long-term holdings” and then pivot into a bigger conversation about Tesla and humanoid robotics.

 

One side picks Amgen, Eli Lilly, and Google as a 5-year core because healthcare demand is steady, those companies “print money,” and Google adds durable tech exposure with less drawdown risk. The other side counters with Nvidia, Google, and TSM (and briefly considers Tesla as a high-upside 5-year bet).

 

From there, the discussion turns into a push-and-pull on Elon and Tesla’s pivot: supporters argue Tesla is really a software, robotics, and autonomy play and that Elo...


The Coinbase Trap_ Why Short-Term Trades are DANGEROUS Right Now!
02/21/2026

Subscribe and watch more videos here:    / @earnyourleisure   Join the EYL community for deeper training and a more detailed approach: https://www.eyluniversity.com Join the number one stock club in the world: https://www.ianinvest.com Invest Fest | August 7-9, 2026 Grab early bird tickets now: https://www.investfest.com

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America’s #1 Club Owner Reveals What Entrepreneurs Are Doing Wrong (The $60M Blueprint)
02/19/2026

0:00 Intro at Park in DC + meet Mark Barnes
2:05 What Park is and why the location is elite
4:40 Club Dream/Love legacy and DC nightlife dominance
10:10 Customer service mindset: cleanliness, staff, experience
20:05 Origin story: messenger business, meeting Russell Simmons and Andre Harrell
22:30 Legendary house party that changed everything
41:40 Building Dream: buying the building and the renovation grind
46:30 Financing the build: $6M, hard money, high pressure
55:15 Black money vs white money in nightlife (why revenue exploded)
1:01:20 Gilbert Arenas million-dollar birthday party breakdown
1:09:15 Brunch formula and why brunch became the game changer<...


Why Your Pursuit of Work-Life Balance is KILLING Your Success
02/18/2026

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Join the EYL community for deeper training and a more detailed approach:
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Invest Fest | August 7-9, 2026
Grab early bird tickets now: https://www.investfest.com

See omnystudio.com/listener for privacy information.


Why Tesla is the Most BIZARRE Stock to Hold for 5 Years
02/17/2026

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Join the EYL community for deeper training and a more detailed approach:
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Invest Fest | August 7-9, 2026
Grab early bird tickets now: https://www.investfest.com

See omnystudio.com/listener for privacy information.


The SHOCKING Truth About $70,000 Private School Tuitions
02/16/2026

Subscribe and watch more videos here: https://www.youtube.com/@EarnYourLeisure

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Invest Fest | August 7-9, 2026
Grab early bird tickets now: https://www.investfest.com

See omnystudio.com/listener for privacy information.