James' World 2

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Back in the 1920s, Charles Mitchell — the swaggering head of National City Bank, the forerunner to Citigroup — had a ritual. He would take his bond salesmen to lunch at the Bankers Club, perched atop the Equitable Building at 120 Broadway, and point to the city below, stretched out in miniature. “There are six million people with incomes that aggregate thousands of millions of dollars,” he’d say. “They are just waiting for someone to come to tell them what to do with their savings. Take a good look, eat a good lunch, and then go down and tell them.”

For Mitchell, finance and the new instruments of wealth — stocks, margin loans, investment trusts, and even exotic foreign bonds — were not to be hidden away but promoted like any other product. “It has always seemed to me that there is, and always has been, too much mystery connected with banking,” he liked to say.

He wasn’t alone in preaching the gospel of access. John Raskob — a top executive at General Motors, a born promoter and the man who built the Empire State Building — famously declared, “Everybody ought to be rich!” He explained: “I didn’t see why the working men and women of our country should not be let in on the tremendous profits being made in America today.” Raskob set out to create one of the first mutual funds, explicitly designed to give “the little fellows” a chance to join the boom.

Nearly a century later, we are in the grip of a sweeping new age of financialization and innovation — the boldest transformation in money and investing since the 1920s — that is also driven by the idea of expanding access to markets. Private equity, venture capital, and private credit, once the preserve of institutions and wealthy individuals, are now about to be repackaged for the masses, even woven into 401(k) retirement plans. Crypto tokens are being sold as a way to buy slices of private firms like SpaceX and OpenAI, in the gray zone of securities law.

It all comes amid a new stock boom, fueled by a mania for A.I., and with a new administration in Washington that is determined to loosen rules — creating a permissive spirit similar to the one that passed for innovation in the 1920s. The Trump administration is working on rolling back key provisions of the Dodd-Frank Act, easing capital requirements for midsize banks, and sidelining the Consumer Financial Protection Bureau — an agency born after 2008 to police predatory lending. Congress, for its part, has advanced measures like the Genius Act and, more recently, the so-called Financial Innovation and Technology for the 21st Century Act — billed as modernization and, in practice, opening the gates for crypto and other speculative products.

And just as in Mitchell’s day, they have their boosters. “Only the biggest companies can go public, which limits opportunities for the little guy,” Vlad Tenev of Robinhood has said, insisting that “the next frontier is making sure these opportunities are open to retail investors.” Marc Rowan of Apollo is equally blunt about retirement savings, arguing that asset managers have “leveraged the future of retirement to four stocks,” which will prove to be “an irresponsible thing for us to have done.”

What has shifted are the buzzwords and the gloss; what has not is the promise — that the American dream itself could be remade into a get-rich fantasy, a promise first popularized in the 1920s. Mitchell’s belief that stocks and bonds were for everyone and should be sold “over the counter, just the same way a clerk sells a necktie,” helped elevate him alongside Babe Ruth and Charles Lindbergh as a symbol of American ambition. Financiers became celebrities and graced the covers of Forbes (started in 1917) and Time (started in 1923) for the first time. Those magazines may have declined in recent decades, but today this same message — of the thrill of a democratized financial sector where anyone can become rich — is fed to us in infinite scrolls on social media of aspiration and envy.

For decades, most Americans have missed out on the stock market’s riches: Nearly 40 percent of Americans don’t own any stock at all, and more than 90 percent of all equities are controlled by the wealthiest 10 percent of families. Access has long been fenced off by rules around “accredited investors,” a legal category created in the 1930s to protect households from risky, opaque offerings. The qualifications are strict: You need $1 million in net worth (excluding your home) or an income of at least $200,000 a year ($300,000 for a couple). The idea is that only the wealthy can afford to lose money in speculative deals. In practice, the definition gives the richest households — about 18 percent of American families — privileged entry into private markets. They can buy into companies like Facebook or Uber years before the public ever has the chance, capturing the overwhelming share of the gains. By the time the average investor can purchase shares on a stock exchange, much of the upside has already been taken.

Now that barrier is being steadily lowered. What was once a bright line meant to keep average investors out is being blurred in the name of access. It is not hard to see the appeal of breaking open those gates and allowing ordinary savers a shot at the kinds of returns that built fortunes for institutions and elites.

Yet history offers a blunt reminder: When transformation comes this quickly, it rarely benefits everyone unless it is paired with transparency, oversight, and regulation. The dot-com boom of the late 1990s was pitched as a democratizing moment, too, until it collapsed under a wave of hype and fraud. The pattern is familiar, stretching back to 1929: Whenever access expands faster than safeguards, charlatans rush in and ordinary investors are often left holding the bag.

The greatest speculative asset class of the past decade has been cryptocurrency, a realm where risk itself is part of the appeal. For years it was dismissed by some of the most venerated investors, like Warren Buffett, as a plaything for gamblers and thrill-seekers. But under a crypto-friendly Trump administration, a new group of financiers is working to reimagine it as something every American should own — not just through exchanges and wallets but through investment vehicles built to slip into retirement accounts and mutual funds.

No one has embraced this idea more passionately than Michael Saylor of the business-software company Strategy (formerly known as MicroStrategy). With his silver beard, clipped diction, and unblinking certainty, Saylor carries himself less like a corporate manager and more like a prophet who believes he has glimpsed the future before anyone else.

For most of its life, Strategy sold analytics tools to corporations. But Saylor has completely recast it. Over the past few years, he borrowed more than $2 billion through debt offerings and convertible notes to buy over 200,000 Bitcoins — worth more than $13 billion at recent prices. Today, Strategy’s stock no longer trades on software sales; it rises and falls almost entirely with the price of Bitcoin. For investors, the appeal is obvious: It is an easy way to buy into Bitcoin’s upside, wrapped in the familiar clothing of a public stock.

Saylor himself has become more than a chief executive; he is Bitcoin’s evangelist in chief. On podcasts, TV hits and conference stages, he preaches the virtues of “digital gold” with a fervor that blends salesman and prophet. To his followers, he is a folk hero who showed Wall Street how to bet big on the future. And so far, he has been right: As Bitcoin recovered from its 2022 crash, Strategy’s shares have soared — rising even faster than the coin itself. Nearly half the company’s stock is now held by retail investors. It is such a popular stock that it was added to the Nasdaq 100 index in late 2024, further attracting almost $4 million a day from individual traders, cementing its status as a cult favorite on Main Street as much as on Wall Street.

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Photo illustration by Ricardo Tomás

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