Mark Cuban's 'Hail Mary' Bitcoin Strategy: How a 10% Gamble Could Make You Rich

Who doesn't dream of waking up significantly richer? In 2017, billionaire entrepreneur and Shark Tank star Mark Cuban shared his straightforward wealth-building playbook in a Vanity Fair video. His nine rules emphasized living frugally, building savings, avoiding credit card debt, and continuous learning. However, one piece of advice stands out for those with a high risk tolerance and a speculative mindset.

The 'Hail Mary' Bitcoin Rule

Cuban advised, "If you're a true adventurer and you really want to throw the Hail Mary, you might take 10%, put it in Bitcoin or Ethereum... but if you do that, you've gotta pretend you've already lost your money." This approach sets a clear boundary: cap your crypto investment and mentally write it off as a loss from the start.

He compared it to collecting items like sneakers or baseball cards—speculative and valuable only if others are willing to buy. "It's a flyer," he noted, emphasizing that "something's worth what somebody else will pay for it."

Potential Returns and Market Context

At the time of Cuban's advice, Bitcoin was trading around $5,600. Fast forward to 2025, and it has averaged near $100,000. For example, a $5,000 investment then could be worth nearly $90,000 today, while $15,000 could approach $270,000.

Emotional Management and Contrasting Views

Cuban's strategy isn't about market timing; it's about managing emotions. By treating the invested money as lost, investors can avoid stress and keep the rest of their portfolio stable. In contrast, Warren Buffett has consistently rejected cryptocurrencies, calling Bitcoin "rat poison" and predicting a bad ending, arguing it lacks intrinsic value and could collapse if demand wanes.

Cuban's 'Hail Mary' advice stands out for its realism—it doesn't promise gains but encourages emotional detachment, ensuring financial stability regardless of the outcome.