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...
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Episode List

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

Feb 26th, 2026 5:37 PM

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 helping creators gain more leverage in the modern economy. Invest Fest Tickets: investfest.com Invest Fest Pitch Comp: https://investfest.com/pitch-competition/ Red Panda: Ianinvest.com EYL University: https://eyluniversity.com/ #EarnYourLeisure #JeffFrommer #Entrepreneurship #CreatorEconomy #Equity #Ownership #Business #WealthBuildingSee omnystudio.com/listener for privacy information.

Are Cheap Stocks All SCAMS?

Feb 24th, 2026 2:00 PM

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:https://www.eyluniversity.com Join the number one stock club in the world:https://www.ianinvest.com Invest Fest | August 7-9, 2026Grab early bird tickets now: https://www.investfest.comSee omnystudio.com/listener for privacy information.

When To Sell a Stock

Feb 23rd, 2026 6:04 PM

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. If they are no longer one or two in the space, and competitors are clearly winning, that is a real reason to exit. Permanent capital loss risk is rising. Too much debt, weak balance sheet, dilution, shrinking market, or “hope” is the strategy. Risk rules were violated. If you use a stop-loss or max drawdown rule (example: 25%), you follow it. A long term timeframe is not an excuse to ignore risk management. Opportunity cost is too high. Even if it might recover, your money could work harder elsewhere in a stronger business or better trend. In short: Do not sell just because you are scared or because the headlines are loud. Sell when the goal is met, the thesis changes, the moat is gone, or risk management demands it. 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, 2026Grab early bird tickets now: https://www.investfest.comSee omnystudio.com/listener for privacy information.

3 Stocks Set to EXPLODE in 5 Years

Feb 22nd, 2026 2:00 PM

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 Elon knows how to pick the next dominant category; skeptics argue it’s speculative, Tesla’s car business has weakened, politics could create backlash, and founders like Elon get more forgiveness (and access to capital) than most entrepreneurs. They end by agreeing robotics is real and coming, especially for factory and repetitive work, but questioning the extreme forecasts like “hundreds of millions” of humanoid robots in the near term. 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, 2026Grab early bird tickets now: https://www.investfest.comSee omnystudio.com/listener for privacy information.

The Coinbase Trap_ Why Short-Term Trades are DANGEROUS Right Now!

Feb 21st, 2026 2:00 PM

They used Coinbase as a real-time example of why short-term trades can be dangerous, especially around earnings. The setup looked bearish: crypto was in a down cycle, other platforms like Robinhood had already shown crypto revenue weakness, Coinbase depends heavily on crypto (with a big chunk tied to Bitcoin), and Coinbase’s earnings came in with misses plus weak guidance and even analyst downgrades. A short-dated put seemed logical. But after-hours price action flipped the script. Despite all the “bad news,” Coinbase popped hard, likely from institutional buying and a short squeeze, and the put got crushed because options traders can’t adjust positions after 4pm. The lesson: even when you’re “right” on the fundamentals, short-term options can still lose because momentum, squeezes, and liquidity hunts can override logic. Their takeaway: if you insist on trading puts, give yourself more time (they suggested roughly 1 month, maybe up to 6 weeks), avoid tight stops, and account for volatility so you don’t get wicked out. 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, 2026Grab early bird tickets now: https://www.investfest.com See omnystudio.com/listener for privacy information.

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