Mark Cuban says 'I've gotten beat' after investing $20M in 85 Shark Tank startups. What you can learn from his mistakes

Moneywise

Thu, September 17, 2026 at 2:15 PM GMT+3 8 min read

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Mark Cuban has made billions by betting on businesses. But even he admits that picking winners isn't easy.

During his 16 seasons on ABC's Shark Tank, Cuban invested roughly $33 million across at least 85 companies pitched on the show. And for years, the results weren't particularly encouraging.

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"I've gotten beat," Cuban told the Full Send Podcast in 2022 (1), saying at the time that his Shark Tank investments had produced a net loss on a cash basis.

But that wasn't the end of the story.

After Cuban's final Shark Tank episode aired in 2025, he told CNBC that he had invested "about $33 million" and received as much as $35 million in cash returns from his investments on the show (2).

Then there were the companies he still owned stakes in.

Cuban estimated the mark-to-market value of his remaining Shark Tank equity to be at "at least $250 million." That figure represents the estimated "fair value" of his ownership stakes rather than money he has actually collected — and those valuations could rise or fall before he sells.

Still, it's a remarkable turnaround from the losses Cuban described just a few years earlier.

It also illustrates something important about investing in young companies: The outcome of a bet may take years to become clear, and even a billionaire with extensive business experience can back plenty of companies that don't work out.

Picking the next big company is difficult

The deals made on Shark Tank generally resemble angel or startup investing, where investors put money into relatively young businesses in exchange for an ownership stake, hoping some will eventually become much more valuable.

The potential payoff can be enormous. So can the risk.

While the often-repeated claim that 90% of startups fail is difficult to substantiate, Shikhar Ghosh, a senior lecturer at the Harvard Business School, found that roughly 70% to 80% of venture-backed companies don't provide investors with the projected return on investment (3).

Of course, Cuban had something most ordinary investors don't: enough wealth to spread millions of dollars across dozens of companies and withstand the investments that failed.

Inevitably, not every investment worked out.

But the value Cuban says his portfolio has accumulated also shows why investors are attracted to the asset class in the first place. A relatively small number of successful companies can potentially make up for plenty of losing bets.

For everyday investors, the takeaway isn't necessarily that you need Cuban's ability to identify the next breakout company. It's that you might want to consider how much risk you're taking, to avoid depending on a single investment to succeed and to build a broader strategy around the money you're willing to put at risk.

Here are a few ways to do that.

Get access to more investment opportunities

Cuban's Shark Tank experience shows why investing in young companies can be so enticing. A winning bet can potentially deliver significant returns, even if plenty of other investments don't work out.

While most investors aren't sitting across from entrepreneurs on a reality TV show, there are ways to gain exposure to companies before they reach the public markets.

SoFi Invest offers access to alternative investment funds that include private credit, real estate, commodities and pre-IPO companies. Alternative investments can carry additional risks, however, so they may not be appropriate for every investor.

For those who prefer to stick with the public markets, SoFi's easy-to-use DIY investing platform lets you ⁠buy stocks, ETFs and more, with no commission fees and no account minimums.

SoFi is designed for both beginners and seasoned investors, with real-time investing news, curated content and the data you need to make smart decisions about the stocks that matter most to you.

Plus, for a limited time you can ⁠get up to $1,000 in stock when you fund a new account.

Start small and build consistency

Of course, you don't need Cuban's millions to start investing. For someone just getting started, consistently putting smaller amounts of money to work can help build an investing habit without requiring a large lump sum.

One way to do that is by building investing into your everyday spending.

With Acorns, you can automatically invest spare change from your everyday purchases into a diversified portfolio of ETFs managed by experts at leading investment firms like Vanguard and BlackRock.

For instance, if you buy a donut for $3.25, Acorns will round up the purchase to $4 and invest the change in a smart investment portfolio. So a $3.25 purchase automatically becomes a 75-cent investment in your future.

Diversification can take some of the pressure off

Starting small is one thing. Deciding where all those contributions should ultimately go is another.

Cuban could afford to spread $33 million across dozens of Shark Tank companies and wait years to see which ones succeeded. Most investors need a portfolio designed around their own goals, timeline and tolerance for risk.

If you prefer a hands-off, tech-forward approach to building wealth, Vanguard's Digital Advisor puts the investing expertise of one of the world's largest asset managers right at your fingertips.

It takes the guesswork out of investing by building a personalized portfolio for you using Vanguard's well-known low-cost ETFs and mutual funds — then keeps things running smoothly with automatic rebalancing.

The platform also offers guidance on saving for retirement and lets you set additional goals as your life evolves. It can even help you think through debt repayment strategies, potentially freeing up more cash to invest toward your long-term plans.

With a minimum investment of just $100, it's an easy way to get started with professionally guided investing.

For every $10,000 in an all-index portfolio, you'll pay approximately $15 to $16 per year.*

You can also test-drive the Vanguard experience with no advisory fees for the first 90 days.

*All investing is subject to risk, including the possible loss of the money you invest.

Know how much risk makes sense for you

Even a diversified portfolio still involves decisions about how much to invest, what level of risk to take and how those choices fit with the rest of your finances.

Cuban can withstand individual investments failing without jeopardizing his financial future. For an everyday investor who is saving for retirement or another major goal, the stakes can be very different.

A financial advisor can help crunch the numbers and build a plan that works.

But hiring an advisor can be a lifelong commitment, which might make or break your retirement. That's why finding reliable advisors is crucial.

That's where Advisor.com can come in. The platform connects you with an expert near you for free.

Advisor.com does the heavy lifting for you, vetting advisors based on track record, client ratios and regulatory background. Plus, their network comprises fiduciaries, who are legally required to act in your best interests.

Just enter a few details about your finances and goals, and Advisor.com's AI-powered matching tool will connect you with a qualified expert best suited for your needs based on your unique financial goals and preferences.

Finding the right advisor isn't always easy — there's no one-size-fits-all solution. That's why Advisor.com lets you set up a free initial consultation, with no obligation to hire, to see if they're the right fit for you.

Do your homework before trying to pick a winner

Cuban's experience also underscores another lesson: Even experienced investors can get individual investments wrong.

If you decide to go beyond a diversified portfolio and choose individual stocks yourself, having access to research can help you evaluate potential opportunities rather than simply chasing the next company that looks like a winner.

⁠For instance, Moby offers expert research and recommendations to help you identify strong, long-term investments backed by advice from former hedge fund analysts.

In four years, and across almost 400 stock picks, their recommendations have beaten the S&P 500 by almost 12% on average. They also offer a 30-day money-back guarantee.

Moby's team spends hundreds of hours sifting through financial news and data to provide you with stock and crypto reports ⁠delivered straight to you. Their research keeps you up-to-the-minute on market shifts and can help you reduce the guesswork behind choosing stocks and ETFs.

What's more, their reports are easy to understand for beginners, so you can become a ⁠smarter investor in just five minutes.

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