As bitcoin adoption has continued to accelerate over the past few years, there are many investors with decades of success in legacy financial markets that have taken notice and helped lead the charge. Let’s take a closer look at five legendary investors that have shown increasing belief in bitcoin. In my humble opinion, you don’t want to bet against these gents.

Tim Draper

Tim Draper is a Silicon Valley entrepreneur and founding partner of VC firm Draper Fisher. Draper reportedly first purchased bitcoin in 2012. In 2014, he purchased 29,656 bitcoin from the U.S. Marshals for $18.7 million ($632 per coin). His purchase consisted of bitcoin that had been confiscated by the U.S. government from the Silk Road black market.

Draper has been making bitcoin price predictions since 2014. His initial predictions came to fruition. His more recent predictions have been slightly off, due to what he says was a “Government that regulated rather than encouraged new technologies. Our new government is more encouraging.”

Towards the end of November of 2024, Draper shared his thoughts with Benzinga: “It is a long-term trend. Bitcoin is just better technology than using banks and governments as the trusted third party. It is transparent, global, open, keeps perfect records, etcetera. It will make the world wealthier. When retailers (for currency) and governments (for taxes) realize that Bitcoin will save them money on each transaction, then there will be a great incentive for everyone to use Bitcoin.”

Larry Fink

As we shared in an article in mid-April, Larry Fink’s about-face with respect to his views on bitcoin has been well documented. BlackRock’s IBIT is the largest spot bitcoin ETF, currently holding over 575,000 bitcoin, or 2.75% of the fixed supply of 21 million bitcoin.

In mid-July, the BlackRock CEO described his journey from proud skeptic to “major believer” in bitcoin. He told CNBC that after studying it, he now believes that bitcoin is a “legitimate financial instrument,” especially if you believe that countries are debasing their currency.

On January 22nd at the World Economic Forum’s conference in Davos, Switzerland, Fink told Bloomberg he believes bitcoin could climb to $700,000 per coin due to currency debasement fears. He stated, “If you’re frightened about the debasement of your currency or you’re frightened of the economic or political stability of your country, you can have an internationally based instrument called Bitcoin that will overcome those local fears.”

Ray Dalio

Ray Dalio is the founder of Bridgewater Associates, the world’s largest hedge fund. His early skepticism from 2017-2019 was similar to Larry Fink’s. In May of 2021, he told CNBC that he owned “some bitcoin.” At the time, Dalio said, “Bitcoin’s greatest risk is its success,” alluding to the fact that government regulation could hamper its success. In December of 2024, he touched on the importance of holding “hard money” like bitcoin and gold.

Dalio’s cautious interest has continued, as he recently told CNBC in Davos that right now bitcoin makes up about 1% of his portfolio.

Bill Miller

Bill Miller served as chairman and CIO of Legg Mason Capital Management, and is considered a legendary value investor. Miller gained notoriety for beating the S&P 500 15 years in a row from ‘91-05. He was an early investor in Amazon, and became one of the earliest prominent proponents of bitcoin. His initial purchases began in 2014 when bitcoin was only $200 per coin. Miller likens bitcoin to digital gold due to its “game-changing technology.”

In January of 2022, Miller shared that bitcoin and investments tied closely to bitcoin represented 50% of his personal assets. Aside from owning bitcoin outright, he also owned shares of bitcoin mining companies and MicroStrategy, the largest corporate bitcoin holder.

Miller has advocated for the average investor to allocate 1% of their net worth to bitcoin: “I think the average investor should ask himself or herself, what do you have in your portfolio that has that kind of track record – number one, is very, very under-penetrated; can provide a service of insurance against financial catastrophe that no one else can provide and can go up 10 times or 50 times? The answer is: nothing.”

Paul Tudor Jones

Paul Tudor Jones founded his hedge fund, Tudor Investment Corporation, in 1980. Jones initially rose to fame after predicting the “Black Monday” stock market crash in 1987.

Jones’ positive view on bitcoin began in 2020, when he said, “The best profit-maximizing strategy is to own the fastest horse. If I am forced to forecast, my bet will be Bitcoin.” He believed that bitcoin could continue to outperform other assets and act as a hedge in a high-inflation environment. In 2020, Jones shared that he had about 2% of his assets in bitcoin.

This percentage has continued to rise, as 13F filings show that as of September 30, 2024, Jones owned 4.4 million shares of BlackRock’s iShares Bitcoin Trust (IBIT).

The Latest Digital Assets News –> Your Inbox

At Crossover Capital, our number one goal is to provide people with the support, knowledge, and access to make informed decisions about their financial futures. Building a foundation for success starts with steady support and a customized approach. Crossover Capital is here to provide the necessary tools we believe are required for growth and to be a champion for our clients’ success.

If you want to receive tools, knowledge, and digital asset insights delivered directly to your inbox twice a month, subscribe here.

Investment advisory services offered through Crossover Capital Brands, LLC (dba Crossover Capital), a Registered Investment Advisor with the U.S. Securities and Exchange Commission.

This material is intended for informational purposes only. It should not be construed as legal or tax advice, and is not intended to replace the advice of a qualified attorney or tax advisor. This information is not an offer or a solicitation to buy or sell securities. The information contained may have been compiled from third party sources, and is believed to be reliable.

Alternative investments – such as hedge funds and private equity/venture capital funds – are speculative and involve a high degree of risk. Likewise, the emergence of digital assets comes with its own speculative characteristics and involves a high degree of risk. Various digital assets have unique features, and the regulatory risk environment continues to change as governance requirements, rules, and lawsuits emerge. There may be material differences in the type of marketplaces available for digital assets, and there could be significant restrictions or limitations on withdrawing from or transferring these types of investments. Digital assets may incur higher fees when compared to traditional assets, and these expenses may offset returns.

Crossover Capital may not be able to independently verify digital asset valuations provided by institutions that hold or offer digital asset services. As a result, Crossover Capital will generally rely on information reported to it by third parties. As such, the information contained herein is for informational purposes. Clients should recognize that they may bear digital asset-based fees and expenses at the manager-level, as well as indirect fees, expenses, and performance-based compensation for digital assets. Spot bitcoin exchange-traded products were recently approved for listing and trading by the SEC. However, such approvals do not indicate SEC approval to use or invest in bitcoin. Clients should remain cautious and aware of the various risks associated with digital assets that have a value tied to bitcoin or other crypto related products.