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 #WealthBuilding

This week on Earn Your Leisure, Jeff Frommer shares the real story behind building and selling his $75 million podcast production company &mdash; and why big exit headlines don&rsquo;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.
&nbsp;
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&rsquo;s helping creators gain more leverage in the modern economy.
&nbsp;
Invest Fest Tickets: investfest.com
Invest Fest Pitch Comp: https://investfest.com/pitch-competition/
Red Panda: Ianinvest.com
EYL University: https://eyluniversity.com/
&nbsp;
#EarnYourLeisure #JeffFrommer #Entrepreneurship #CreatorEconomy #Equity #Ownership #Business #WealthBuilding

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

Earn Your Leisure

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

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/a74fb49d-deb6-456a-8c1c-b3fd00aae9ea/transcript

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.

 

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

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&ndash;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.
&nbsp;
Subscribe and watch more videos here: <a href="https://www.youtube.com/@EarnYourLeisure" aria-label="YouTube Channel Link: @EarnYourLeisure">&nbsp;&nbsp;&nbsp;/ @earnyourleisure&nbsp;&nbsp;</a>
Join the EYL community for deeper training and a more detailed approach:&nbsp;<a href="https://www.eyluniversity.com">https://www.eyluniversity.com</a>
Join the number one stock club in the world:&nbsp;<a href="https://www.ianinvest.com">https://www.ianinvest.com</a>
Invest Fest | August 7-9, 2026 Grab early bird tickets now:&nbsp;<a href="https://www.youtube.com/redirect?event=video_description&amp;redir_token=QUFFLUhqbFlZam9OanNOMmJkXzgzcURxOGNSX1pUVHVxd3xBQ3Jtc0tuS21BcXpzbUVSc2laY2xnV1R6bVhwSGctOHBzdXNOMVFiMHBqa00xYmJpakdLNER2RXN6NVFIS1E5aUptNnZhTWx4QnVieUhkbDJ0aVZtTl9jdWhJTWN1UW1VUDFLZUROazZyLW0wUmNZQWtJU01jYw&amp;q=https%3A%2F%2Fwww.investfest.com%2F&amp;v=dgbH5v75OR4">https://www.investfest.com</a>

The 300 Trade Rule Why You MUST Practice Before Going Live!

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/05a88318-f04e-4cfa-a3b4-b3ff00fe7f5f/transcript

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, 2026
Grab early bird tickets now: https://www.investfest.com

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 &ldquo;the next 20 to 200&rdquo; story.
&nbsp;
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

Are Cheap Stocks All SCAMS?

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/46a5b923-e9bd-4823-9d87-b3fa0129ef07/transcript

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, 2026
Grab early bird tickets now: https://www.investfest.com

Sell a long term position when one of these is true:
&nbsp;
<ul>
<li>
You already hit your &ldquo;freedom number.&rdquo; If the goal is reached and you are locking in lifestyle security, reducing risk, or shifting into more stable assets, selling can make sense.
</li>
<li>
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 &ldquo;hold,&rdquo; it is a new decision.
</li>
<li>
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.
</li>
<li>
Permanent capital loss risk is rising. Too much debt, weak balance sheet, dilution, shrinking market, or &ldquo;hope&rdquo; is the strategy.
</li>
<li>
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.
</li>
<li>
Opportunity cost is too high. Even if it might recover, your money could work harder elsewhere in a stronger business or better trend.
</li>
</ul>
&nbsp;
&nbsp;
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.
&nbsp;
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

When To Sell a Stock

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/e3b6ae6a-7ad3-4e49-a1f4-b3fa012929e0/transcript

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

In 1 playlist(s)

Earn Your Leisure

Social links

Follow podcast

Recent clips