Fittingly the most consequential crypto development came last on the calendar–and has earned its place in our finale.
On August 7, 2025, President Trump signed Executive Order 14330: Democratizing Access to Alternative Assets For 401(k) Investors (Fact Sheet, Text, Federal Register copy). Last week, nine Republican lawmakers sent this letter to SEC Chair Paul Atkins in support, opening with:
We write to express our support for President Trump’s August 7, 2025, Executive Order 14330 on “Democratizing Access to Alternative Assets for 401(k) Investors” (EO). We applaud the EO’s policy “that every American preparing for retirement should have access to funds that include investments in alternative assets when the relevant plan fiduciary determines that such access provides an appropriate opportunity. . .to enhance the net risk-adjusted returns[.]”
On its face, there is absolutely nothing wrong with Americans having “access to funds that include investments in alternative assets.” The problem, as it so often is, is definitions. Bitcoin is not an alternative asset (at least not in the way the nine Republicans are using the term), and as such, one cannot invest in it.
First, Some Recent History
The cracks started early. At Consensus 2017, Fidelity CEO Abigail Johnson surprised many by praising crypto:
I’m here because I love this stuff… all that the future might hold.
In traditional financial circles, it was a rare vote of confidence. Charlie Munger had called it “rat poison.” Warren Buffet doubled down: “rat poison squared.” Jamie Dimon was a skeptic. Aswath Damodaran shouted from the rooftops that Bitcoin is not an investment. For a while, it seemed crypto might never win the tradfi hearts.
Fidelity Gets Serious
In spring 2022, Fidelity Investments announced it would allow companies to offer employees the option to invest up to 20 percent of their 401(k)s in Bitcoin. Dave Gray, head of workplace retirement offerings and platforms, said:
There is growing interest from (retirement) plan sponsors for vehicles that enable them to provide their employees access to digital assets in defined contribution plans, and in turn from individuals with an appetite to incorporate cryptocurrencies into their long-term investment strategies.
But Not Everyone Was Convinced…
Madeline Hume, CFA and Morningstar Research Analyst, commented:
While Morningstar is not against cryptocurrency—and full disclosure, I own some bitcoin—Fidelity’s strategy for capitalizing on the crypto momentum is misplaced. At this stage, mixing bitcoin and 401(k) plans is a terrible idea.
…Including Elizabeth Warren
In May 2022, Senator Elizabeth Warren and Senator Tina Smith sent a letter to Fidelity CEO Abigail Johnson questioning the plan. They took some heat for it. Then, three months later, they teamed up with Senator Richard Durbin and sent another letter (PDF) to Johnson, warning:
Retirement accounts must be held to a higher standard, one that Bitcoin and other unregulated digital assets fail to meet.
In November, the trio followed up again (PDF), urging Fidelity to “seriously reconsider its decision to allow plan sponsors to offer Bitcoin exposure to plan participants.”
…And The Department of Labor
In 2022, The Department issued a compliance release (PDF), cautioning:
In recent months, the Department of Labor has become aware of firms marketing investments in cryptocurrencies to 401(k) plans as potential investment options for plan participants. The Department cautions plan fiduciaries to exercise extreme care before they consider adding a cryptocurrency option to a 401(k) plan’s investment menu for plan participants.
Vanguard Chooses To Be Careful
Vanguard is Jack Bogle’s legacy. Here is what he said about Bitcoin:
Bogle passed away in 2019, but Vanguard remained true to his ethos. They put their foot down in January 2024, doubled down in March, and tripled down in December–breaking from Fidelity.
The Tide Has Turned
When Abigail Johnson said she “love[s] this stuff,” Bitcoin was trading in the $2,000-$2,500 range. Later that year, it flirted with $20,000. By early 2019, it had dropped to the $3,000s. In November 2021, it hit an all-time high of $69,000. After retreating to the $16,000s, it surged again to an all-time-high of $124,290 on August 14, 2025. It now fluctuates between $110,000-115,000.
Through it all Bitcoin’s fundamentals have never changed. So, what has? A couple of things:
Its price; and
Most people’s opinions, based on the price.
Let’s take a look.
Finance Heavyweights: Buffett / Dimon / Damodaran
Buffett, to his credit, has remained consistent–aside from a rare moment of frustration.
Same with Jamie Dimon. Critics call him out for doing business in Bitcoin, but we see no issue there.
Damodaran, inexplicably, changed his stance. Maybe he thinks it doesn’t matter and markets will do what markets do. But it does matter. Someone of Damodaran’s caliber referring to Bitcoin and alternative investments in the same breath (despite him saying the exact opposite just a few years ago), gives cover to the nine Republicans who wrote:
...every American preparing for retirement should have access to funds that include investments in alternative assets…
The Damodaran we knew four years ago would’ve called that idea (Bitcoin’s inclusion in retirement plans) ridiculous. Now? We’re not sure. Unfortunately, unsuspecting Americans nearing retirement may wind up paying the price.
Hume, the Morningstar Analyst
It’s unclear what Hume thinks of Bitcoin today, but her initial statement hinted at a slippery slope. After concluding that Bitcoin and 401(k)s don’t mix, she explained:
Here’s why: Our recent research shows that cryptocurrency is still very much a speculative asset. At this point, the asset class lacks academically substantiated valuation models. Stocks have free cash flows and bonds have loan principals that can be modeled and give these securities their value. Bitcoin has neither, and that makes it too volatile for direct investment through a 401(k).
She was right–but for the wrong reasons. Mixing Bitcoin and 401(k) plans is indeed a terrible idea. It always was, still is, and always will be. Calling crypto speculative doesn’t require “recent research.” It’s universally true–whether Bitcoin goes to zero or a million.
To her credit, she was more firm in this video:
When we like to think about cryptocurrencies, we don’t think of them as an investment, we think of them as a bet. (around the 3:50 mark)
Speculation is a better word than “bet.” Bets typically involve games or claims on contingent events–not assets with indefinite life. That subtlety aside, at least she’s one of the few who knows better than to call Bitcoin an investment. Great–Americans need more people like her making those statements.
Unfortunately the signals are getting crossed. If you’re convinced Bitcoin isn’t an investment– and it sounds like she is, just as we are– then say it all the time, on all the platforms. Pound the table. Shout it from the rooftops. Phrases like “recent research” and qualifiers like “too volatile for direct investment” are not enough.
Senator Warren
Elizabeth Warren hasn’t changed her stance on crypto–but it wasn’t quite right to begin with. In her first letter (press release, PDF) to Abigail Johnson, she wrote:
Investing in cryptocurrencies is a risky and speculative gamble, and we are concerned that Fidelity would take these risks with millions of Americans’ retirement savings.
Senator, you cannot invest in crypto. And buying it isn’t gambling either, even though it might appear or feel that way on the surface. Throwing all these words into one sentence has diluted your rightful concern, and inadvertently strengthens the speculative side of crypto.
The Department of Labor
The Department of Labor did change its stance. In 2025, it rescinded its 2022 guidance in full.
Vanguard
Vanguard is Jack Bogle, but he is long gone, short-term expectations are real, and Fidelity is winning the hearts and minds of the new generation with its lax crypto stance. For a while, it looked like Vanguard would hold firm–doing what was likely best for its long-term reputation and brand value. But now, it seems the firm is rethinking its position. “Avoid it like the plague?” Jack Bogle’s words may soon be just a distant memory.
Final Thoughts
History may not repeat itself, but it often rhymes. In the 1920s, figures like the Jackal of Wall Street thrived by feeding speculative appetites. The economy was booming… until it wasn’t. Congress found that half of new securities were worthless. The Jackal earned the dubious honor of being cited during the congressional hearings which ultimately led to the Securities Act of 1933 and The Securities Exchange Act of 1934–the foundation of the SEC.
It was a solid response. It protected future generations. But make no mistake: It was reactionary. For many, the damage was already done.
That solid foundation is facing an uncertain future. The Securities Act of 1933 was called the “truth in securities” law for a reason; it was about ensuring full and fair disclosure. Since 1970, quarterly filings have been a cornerstone of that disclosure, but that cadence is under pressure. The twice-a-year reporting idea gains momentum daily. In other words: More speculation is on the horizon.
And then there’s crypto.
We believe most tokens are securities–even if the SEC disagrees. We’re convinced they lack intrinsic value–even if Pompliano and others dispute the concept itself. We also believe that many retirement accounts are in real danger, even if plan administrators see things differently.
It’s impossible to predict the next crisis. No one can time it. If someone claims they can, run for the hills. That said:
If the finance gods have a sense of humor, 2029 might be the year. Great Depression Reloaded–exactly one century later.
Disclaimer: So we’re not mistaken as crypto shorts hoping to profit from a crash, we’re not anti-crypto and we’re not short; in fact, we are long. We understand some of the underlying technology holds real promise. America can be the crypto capital of the world–but only if we first agree on what investing means.
For many Americans, having access to alternative assets is a good idea, but… Bitcoin is not an alternative asset one can invest in. It’s a speculative tool that may make one rich quickly. Or not.
For those who don’t grasp that reality, retirement may never come.
