Mark Cuban: ‘I’ve gotten beat.’ After investing 20M into his first 85 Shark Tank investments they lost money
May 17, 2026
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Mark Cuban became a billionaire by starting and selling multiple businesses, but most know him best from his time on the hit ABC show Shark Tank. As an investor on the reality show, he took a chance on at least 85 startup ideas pitched by contestants.
But in a 2022 interview, Cuban revealed that his broad suite of investment deals on the show actually made a net loss.
“I’ve gotten beat,” the billionaire told the Full Send podcast (1). Cuban invested $20 million dollars over hundreds of episodes since joining the show in 2011, and announced in the fall of 2024 that he was stepping down after 16 seasons.
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While initially he accounted for a net loss on a cash basis in 2022, after his final episode aired in 2025, Cuban told CNBC he earned up to $35 million in cash returns and that his mark-to-market equity from those businesses is worth “at least $250 million (2).” Since this metric measures the fair market value of investments, that number represents paper gains, not cash in hand.
So, what can you learn from his time there? This rare look behind the scenes of the reality TV show offers everyday savers and investors three key lessons.
Startups are risky
Investments popularized by shows like Shark Tank can best be described as angel investing, venture capital, or startup investing. That’s because the ideas presented on the show are usually from early-stage companies with a short track record and an eye-catching idea, rather than from established businesses.
When considering Cuban’s track record relative to how this asset class generally performs, his investment success rate isn’t unusual. While there’s a common myth in the startup world that 90% of startups fail, Harvard Business School estimates the figure is closer to 75% (3).
Regardless, most startups are more likely to fail than deliver outsized returns.
Make safe bets
Even with a high failure rate, the high-risk nature of startup investing can be a thrill for high-net-worth investors like Cuban, with well-diversified portfolios and plenty of assets to play with. But for the average investor who is looking for a secure retirement, it’s probably better to consider guaranteed returns and low-risk investing.
A high-yield account like a Wealthfront Cash Account can be a great place to grow your uninvested cash, offering both competitive interest rates and easy access to your money when you need it.
A Wealthfront Cash Account currently offers a base APY of 3.30% through program banks, and new clients can get an extra 0.75% boost during their first three months on up to $150,000 for a total variable APY of 4.05%.
That’s ten times the national deposit savings rate, according to the FDIC’s March report.
Additionally, Wealthfront is offering new clients who enable direct deposit ($1,000/mo minimum) to their Cash Account and open and fund a new investment account an additional 0.25% APY increase with no expiration date or balance limit, meaning your APY could be as high as 4.30%.
With no minimum balances or account fees, as well as 24/7 withdrawals and free domestic wire transfers, your funds remain accessible at all times. Plus, you get access to up to $8M FDIC Insurance eligibility through program banks.
Start small and be consistent
New investors will want to gradually become comfortable with the inherent risks of investing, since invested cash can go up or down. Investing is emotional, so starting small means you can experience those ups and downs on a nominal amount of income and test your risk tolerance.
Acorns allows you to build up your investing muscle using small amounts of cash.
Whenever you make a purchase with your linked debit or credit card, the app automatically rounds up the total cost to the nearest dollar and invests the change in a diversified portfolio. You can also link these investments to your IRA, ensuring you’re maximizing your retirement savings with every purchase you make.
Then there’s Moneywise’s top picks for the Best High-Yield Savings Accounts of 2026. It’s another great way to compare options for growing your savings safely.
Read More: Non-millionaires can now hoard property like the 1% — how to start with as little as $100
Established businesses are safer alternatives
Instead of focusing on early-stage companies with lofty expectations of future returns, everyday investors could turn their attention to established firms with robust track records.
For instance, Cuban acquired a majority stake in the NBA’s Dallas Mavericks for $285 million from real estate developer Ross Perot Jr. — 20 years after the brand was established. It’s gone on to be one of his most successful investments.
While you might not be able to buy a sports team, there are plenty of other investment opportunities that can be both accessible and fruitful.
Always research your investments first
Stock picking is notoriously risky, but there are ways to make safer investments and benefit from the wisdom of experts.
Moby, an investment advice platform, can help you reduce the guesswork when selecting stocks and ETFs. In four years, across almost 400 stock picks, Moby’s recommendations have beaten the S&P 500 by nearly 12%, on average.
With their easy-to-understand market research, you can become a wiser investor in just five minutes, all with their 30-day money-back guarantee.
Diversification is important
Yet another key lesson from Cuban’s investments is that he spreads his money across different bets.
Cuban’s portfolio stretches far beyond the companies he’s chosen on Shark Tank. His business empire includes stakes in companies ranging from generic pharmaceuticals to tech and entertainment. His well-diversified approach could be one of the reasons why the entrepreneur has continued to build wealth despite several missteps and failed ventures along the way.
The lesson for ordinary investors is clear: diversify.
Invest in residential real estate
Real estate has historically been a robust market for investors. But since prices have soared, it has become increasingly hard to break into this market.
Luckily, new investing platforms are also making it easier than ever to leverage residential real estate.
Lightstone DIRECT’s direct-to-investor model ensures a high degree of alignment between individual investors and a vertically-integrated, institutional owner-operator — a sophisticated and streamlined option for individual investors looking to diversify into private-market real estate.
With Lightstone DIRECT, accredited individuals can access the same multifamily and industrial assets Lightstone pursues with its own capital, with minimum investments starting at $100,000.
According to a 2025 Deloitte survey, nearly 75% of commercial real estate leaders plan to increase their investments over the next 12 to 28 months (4). Most respondents cited commercial real estate’s inflation-hedging benefits as their reason for increasing their stakes.
Keep in mind that owning a share of commercial property does hold some risk — for instance, you could receive no returns, and these assets are often illiquid. Speak to a professional to determine whether this kind of investment is right for you, especially if you are retired or close to retirement.
Leverage gold as a safe haven
Then there’s gold. The precious metal remains a solid performer and the backbone of many wealthy investors’ portfolios. Its steady performance has made it a safe haven for many investors.
During the 2008 stock market crash, gold prices rose as share prices tumbled — cushioning the portfolios of investors who were savvy enough to diversify with this commodity.
With a gold IRA, you can build up your retirement fund with an inflation-hedging asset.
One way to invest in gold that also provides significant tax advantages is to open a gold IRA with the help of Priority Gold.
Gold IRAs allow investors to hold physical gold or gold-related assets within a retirement account, which combines the tax advantages of an IRA with the protective benefits of investing in gold, making it an attractive option for those looking to potentially hedge their retirement funds against economic uncertainty.
To learn more, you can get a free information guide that includes details on how to get up to $10,000 in free silver on qualifying purchases.
Diversify into fine art
Since art has low correlation to traditional stock markets, it can be a great way to diversify your portfolio.
In 1999, the S&P 500 peaked, and it took 14 long years to fully recover.
Today? Goldman Sachs is forecasting just 3% annual returns from 2024 to 2034. It sounds bleak but it’s not surprising: the S&P is trading at its highest price-to-earnings ratio since the dot-com boom. Vanguard isn’t far off, projecting around 5%.
In fact, nearly everything feels priced near all-time highs — equities, gold, crypto, you name it.
That’s why billionaires have long carved out a slice of their portfolios in an asset class with low correlation to the market and strong rebound potential: post-war and contemporary art.
It may sound surprising, but more than 70,000 investors have followed suit since 2019 — through Masterworks. Now you can own fractional shares of works by Banksy, Basquiat, Picasso and more.
Masterworks has sold 25 artworks so far, yielding net annualized returns like 14.6%, 17.6% and 17.8%.*
Moneywise readers can get priority access to diversify with art: Skip the waitlist here.
Past performance is not indicative of future returns. Investing involves risk. See important Regulation A disclosures at Masterworks.com/cd.
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Article sources
We rely only on vetted sources and credible third-party reporting. For details, see our editorial ethics and guidelines.
Youtube (1); CNBC (2); Harvard Business School (3); Deloitte (4)
This article provides information only and should not be construed as advice. It is provided without warranty of any kind.
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