Dave Portnoy says it took him 10 years to get to $1M — but now he’s ‘over the hump’ and can make $5M in a week

Vishesh Raisinghani

Mon, Jun 9, 2025, 2:11 PM 4 min read

For a man who built a media empire out of hot takes and hustle, Dave Portnoy’s biggest money lesson is surprisingly simple: “Once you get it, it's easy to get a lot more," he told Shannon Sharpe on a recent episode of the Club Shay Shay podcast.

The entrepreneur, who sold his company Barstool Sports to Penn Entertainment for about $500 million only to buy it back for $1 a few years later, says it took him a decade to accumulate his first million. But once he did, making money became significantly easier and he now claims to be able to generate $5 million in a week.

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"Once you get over the hump it just comes [to you]," says the 48-year-old online influencer.

Here’s why wealth creation can accelerate after you hit certain milestones.

Portnoy is referring to compound growth, a key strategy used by many to grow wealth. The late Charlie Munger often described it as “getting a snowball rolling down a hill.”

The snowball effect helps to explain why wealth creation accelerates once a person has hit certain financial milestones. An investor who starts off with no money and invests $1,000 a month in an asset that generates 10% annual returns would make $100,000 in 6.5 years. But with compound growth, that $100,000 would take just four years to grow to $200,000, and just three more years to reach $300,000.

This is because an investor with $100,000 is earning returns not only on their monthly contributions but also their accumulated wealth.

Put another way, an investor with $100 million in net worth can easily generate $5 million quickly — perhaps within a week — because they would need to earn just 5% on their assets to do so.

In fact, Portnoy admitted during the interview that he once “spent five hours just talking about the interest" he was earning on his cash after he got rich. "I couldn't believe it, I was making money not doing anything."

This is why your early financial milestones are so critical in your long-term wealth creation journey: the earlier you start investing large amounts of money, the longer it has to grow with the most growth opportunity.