From Haters to Hodlers: 5 Billionaires Who Converted to Bitcoin

For more than a decade, Bitcoin has sparked debate, fear, and fascination. Some see it as a bubble ready to burst, others as a hedge against inflation. It's especially revealing to watch how views shift among those who manage billions. 

We’ve selected five prominent billionaires who initially dismissed Bitcoin but later came to recognize its strength and became supporters. Each story shows how quickly perceptions of new technology can change.

Kevin O’Leary

Kevin O’Leary is a Canadian entrepreneur, venture investor, and well-known television personality, best known for his role on Shark Tank, where he earned a reputation as a tough and pragmatic businessman, earning the nickname “Mr. Wonderful.” He founded SoftKey Software Products, which was later sold for billions, and remains active in investing across tech, finance, and startups.

Even with his experience, O’Leary was once skeptical of Bitcoin.

May 2019: Total Rejection

In an interview with Cointelegraph, O’Leary called Bitcoin “garbage” and a “useless currency.” He pointed to the asset’s extreme volatility, its impracticality for large transactions, and the difficulties of using it in traditional business. His opinion formed after a failed attempt to buy property in Switzerland using Bitcoin. The seller insisted on guarantees that the amount would be fixed in fiat currency, which O’Leary saw as evidence that Bitcoin couldn’t function as a reliable means of payment.

May 2021: A Complete Turnaround

Two years later, O’Leary revealed that he invested 3–5% of his portfolio in Bitcoin. He explained the move by pointing to changes in the crypto market and the emergence of a more developed infrastructure for institutional investors. He also became a strategic investor in DeFi Ventures, a startup focused on decentralized finance, which was later renamed WonderFi Technologies after O’Leary’s own nickname.

Today: A Committed Supporter

Kevin O’Leary now believes that cryptocurrency will become part of every sector of the U.S. economy. He takes an active role in crypto conferences and discussions on digital asset regulation, and he emphasizes the importance of blockchain in transforming the global financial system. O’Leary also supports the development of sustainable mining, pointing out that environmental responsibility will be central to the future of crypto adoption.

In a recent interview, he summed up his shift in perspective: “I have millions of dollars, 20% of my portfolio is now in cryptocurrencies and blockchain.”

Raymond Dalio 

Ray Dalio is an American billionaire, investor, and the founder of Bridgewater Associates, the world’s largest hedge fund. He is known for his deep economic insights, his perspective on global financial trends, and his bestselling book Principles: Life and Work. For decades, Dalio has been considered one of the most influential investors on Wall Street.

September 2017: Sharp Skepticism

In an interview, Dalio described Bitcoin as a bubble and a highly speculative market. He pointed to its extreme volatility and its limitations as a medium of exchange, and he questioned whether it could develop in a sustainable way. He also suggested that governments might intervene and ban Bitcoin if it ever posed a real threat to fiat currencies.

2021: A Shift in Perspective 

By 2021, Dalio had significantly revised his view. In an interview with CNBC and in other public comments, he said that Bitcoin could play an important role in preserving wealth, particularly in a climate of rising inflation and weakening confidence in government currencies. He acknowledged that he owns Bitcoin, though he noted it represents only a small share of his portfolio.

Today: “Digital Gold”

Dalio now sees Bitcoin as a potential digital counterpart to gold, an asset that can hold its value during financial crises and periods of instability. While he continues to voice caution about regulation and the risk of government intervention, his view of crypto has become more measured. He acknowledges that it has become part of today’s financial reality and believes it deserves serious attention from investors.

Mark Cuban 

Mark Cuban is an American entrepreneur, billionaire, and owner of the Dallas Mavericks basketball team. He is also known as one of the “sharks” on the reality TV series Shark Tank.

September 2019: “I’d Rather Have Bananas”

In September 2019, Cuban expressed doubt about Bitcoin’s value, saying he would rather own bananas, since at least they can be eaten. He stressed that cryptocurrency has no intrinsic value and noted that most people find it too complicated to understand.

2021: A Shift in Perspective and Investment in Crypto Projects

By 2021, Cuban had reconsidered his stance on cryptocurrency. He began actively investing in blockchain and decentralized finance (DeFi) ventures. In interviews, he said DeFi reminded him of the early days of the internet, pointing to the technology’s potential.

Cuban also invested in Mintable, an NFT marketplace that raised $13 million in a Series A funding round in July 2021.

Today: A Web3 Evangelist

Cuban is now an active supporter of cryptocurrency and blockchain technology. He believes that DeFi and NFTs have the potential to significantly reshape both the financial system and the entertainment industry. He continues to invest in crypto projects and takes an active role in the development of the space.

John McAfee 

John McAfee was a British-American programmer and entrepreneur, best known as the founder of McAfee, the company that created the first commercial antivirus software. Throughout his life, he was known for his eccentric behavior and provocative statements, especially about Bitcoin.

Before 2016: Skepticism

Before 2016, McAfee voiced doubts about Bitcoin, citing its limitations as a currency and the slow speed of its transactions. He showed a preference for other technologies, such as privacy coins like Monero and blockchains with higher transaction capacity.

2017: The Legendary Bet 

In 2017, John McAfee dramatically changed his stance on Bitcoin and became one of its most vocal supporters. He predicted that Bitcoin would reach $500,000 by the end of 2020, later raising that forecast to $1 million. In July 2017, McAfee wrote on X: “if not, I will eat my dick on national television.”

By January 2020, he dismissed the statement, writing: “Eat my dick in 12 months? A ruse to onboard new users. It worked.”

Tragic Ending

John McAfee died in 2021. He was found dead in a prison cell in Spain, where he was awaiting extradition to the United States. The official cause was ruled as suicide, though some of his supporters have questioned that conclusion.

Jamie Dimon 

Jamie Dimon is the chairman and CEO of JPMorgan Chase, one of the largest banks in the world. He is known for his direct approach and strong influence in the financial industry. As an experienced banker, Dimon was long skeptical of cryptocurrencies, particularly Bitcoin. Over time, however, his stance has become more measured, especially in his view of blockchain technology.

September 2017: “Fraud”

In September 2017, Dimon called Bitcoin a fraud, compared it to tulip mania, and predicted its collapse. He said he would fire any JPMorgan employee caught trading Bitcoin, calling it too dangerous. He also argued that Bitcoin wouldn’t work and claimed it was worse than tulip bulbs.

January 2018: A Change in Tone 

In January 2018, Dimon expressed regret over his earlier remarks, saying he wished he hadn’t called Bitcoin a fraud. He also acknowledged the potential of blockchain technology, emphasizing that it is a real innovation with practical value.

Today: Distrust of Bitcoin, Loyalty to Clients

Although Dimon recognizes the potential of blockchain, he remains critical of Bitcoin. In December 2023, he described cryptocurrencies as “decentralized Ponzi schemes” and said the government should shut them down. However, in May 2025, JPMorgan Chase announced it would allow clients to purchase Bitcoin, despite Dimon’s personal skepticism. He stated that while he does not support Bitcoin himself, he respects his clients’ right to make their own investment decisions.

Conclusion

The stories of these billionaires show just how dramatically attitudes toward Bitcoin can shift even among the most influential investors. What began as outright rejection and public criticism has, in many cases, turned into investment and recognition of crypto as part of the future financial system. Their views may differ, but one thing is clear: Bitcoin can no longer be ignored. It has become a permanent part of the global investment landscape and a force even the most powerful figures in traditional finance must reckon with. This is more than a change in opinion; it reflects the moment when new technology and deep capital begin to align.