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.

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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.

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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.

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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
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See omnystudio.com/listener for privacy information.