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Beneath the Surface

The Tenev Dilemma

Loading ...Addison Wiggin

January 30, 2025 • 3 minute, 30 second read


goldMain StreetPopulismWall Street

The Tenev Dilemma

“Once in a while you get shown the light… in the strangest of places if you look at it right.”

– Jerry Garcia


 

January 30, 2025 — And so it begins…

Three seemingly random ideas hitting our “inbox” at the same time — can’t be a coincidence. “Rabbit holes” don’t just appear on their own.

Yesterday, I had just wrapped up a brand-spanking-new Wiggin Session interview with Grey Swan Investment Fraternity Contributor Mark Jeftovic.

At the end, Mark Jeftovic was unpacking what he calls “hyperbitcoinization,” or the rapid increase and stabilization of digital assets in the global monetary system.

As I was digesting that, one of our researchers pointed to an op-ed in the Washington Post by Vlad Tenev.

To add to the intrigue, I had a report on my desk from Mike Huckabee, with whom we had a publishing relationship before President Trump appointed him as U.S. Ambassador to Israel.

On the cover, Huckabee summarized his analysis of Trump’s regulatory approach to Wall Street and the SEC thus: “Those on the right side of Trump’s investment policies will be millionaires. Those on the wrong side will be left behind.”

Et voila. Three ideas… no clear path.

So let’s make one.

Let’s begin with Tenev.

Vlad Tenev, the co-founder and CEO of Robinhood, argues that everyday investors are locked out of the best startup opportunities — companies like OpenAI and SpaceX — while the ultra-rich reap the rewards.

Meanwhile, retail investors are left playing in the high-risk sandbox of meme stocks, has-beens, and questionable IPOs.

Robinhood was supposed to be the great equalizer. Tenev and Baiju Bhatt launched the platform in 2013 with a promise: free and easy access to investing.

But in 2021, that promise came under fire when Robinhood restricted purchases of GameStop stock during its now-infamous short squeeze (other brokers did the same).

Many believed the move wasn’t about “protecting” investors but shielding hedge funds like Citadel Securities.

Tenev isn’t wrong about one thing: SEC regulations make it easier for the ultra-rich to access private markets while smaller investors get stuck with the lower-performing scraps.

But he fails to mention that Robinhood makes its money selling users’ trading data to Citadel, which then profits by front-running those trades.

In other words, when you put in a bid for Tesla Motors shares, you may pay a penny more as Citadel’s algorithms spoof some bids to drive up the price. A penny ain’t much, but do it a few billion times a day, and soon you’re talking real money.

That means that Robinhood, for all its populist branding, serves Wall Street’s biggest players first.

Now, the ground is shifting. The rise of digital assets and tokenization could finally open private markets to everyone from the ground up, not the bottom down.

Trump has made it clear in his second week in the White House that he’s pushing policies to accelerate blockchain-based investments, giving retail investors access to a playing field long dominated by insiders.

So, the real question isn’t whether the rules should change — they already are. It’s whether Tenev and companies like Robinhood will actually champion financial democratization or simply find new ways to funnel small investors into Wall Street’s favorite profit machine.

That’s the dilemma.

To solve it we need a good dose of Grey Swan methodology. As Gretzky said, we have to“skate to where the puck is going,” not sit on our arses and wait for the puck to come to us.

More to come as we connect the dots of populism (both political and financial)…

Regards,


Addison Wiggin,
Grey Swan

P.S. One of the places the financial puck is going is toward higher gold prices. The metal is close to hitting a new all-time dollar high of $2,800 per ounce. As promised, you can find our latest gold forecast here.

Fair warning: The headline number you see as a prediction for gold’s price has been dubbed “outrageous” by our publisher.

But after seeing our data, he’s also been pushing to get this info out as soon as possible. Take a look and judge for yourself. And let us know what you think: addison@greyswanfraternity.com


Grey Swan #2: The Crack-Up Boom Reaches Terminal Velocity

January 1, 2026 • Addison Wiggin

The crack-up boom does not signal immediate collapse. Monetary policy gets a new master… inflation rages… and investors chase stocks as a means of keeping pace with their savings.

Markets may even finish 2026 higher than they begin. Many investors will still lose purchasing power along the way. Terminal velocity will feel like momentum… until reality hits.

In 2026, expect breathtaking advances, with the AI narrative remaining dominant, and sudden reversals to occur quickly. Expect liquidity to remain plentiful and erode discipline even more.

Grey Swan #2: The Crack-Up Boom Reaches Terminal Velocity
Grey Swan #3: The Midterms Deliver a Socialist Majority in the House

December 31, 2025 • Addison Wiggin

If the socialist agenda lands, the reaction matters as much as the results of the initial vote.

A hostile House gridlocks legislation. Investigations proliferate. Impeachment chatter returns. Executive authority stretches to compensate.

The political goal of the reactionary strategist will be to muck up the Trump realignment as much as possible to regain power in the House, the Senate (eventually), fortify the courts and ultimately take back the Oval Office. 

Trump will not face a midterm defeat like past lame-duck presidents. We’ll see a host of creative efforts to assert executive authority and override the people’s House. The checks and balances bestowed by Montesquieu at the very root of the Republic will be tested as never before.

Grey Swan #3: The Midterms Deliver a Socialist Majority in the House
Grey Swan #4: America’s Covert Resource War in South America

December 30, 2025 • Addison Wiggin

If the U.S. can no longer afford to police the world, it will prioritize what sits closest to home. Oil, lithium, copper, rare earths, food, and shipping lanes in the Western Hemisphere matter more to America’s economic resilience than abstract security guarantees signed eight decades ago.

The Financial Times captured this shift late in 2025, noting that U.S. foreign policy is “increasingly transactional, geographically compressed, and resource-oriented.” Bloomberg went further, describing a “hemispheric retrenchment” underway beneath the noise of global diplomacy.

We have observed passively that empires of the past, burdened by debt, stop expanding ideologically and start contracting strategically. If nothing else, this is a guide that helps decipher Trump’s comedic efforts at the podium on the second-term victory tour he’s on.

Grey Swan #4: America’s Covert Resource War in South America
Grey Swan #5: The European Union Fractures Under the Weight of War, Debt, and Bureaucracy

December 29, 2025 • Addison Wiggin

By 2026, all four supports will demonstrate that they’ve weakened simultaneously. As true as it may or may not be, it’s not likely to be understood, let alone covered by old-school national media.

Debt narrows choices. War hardens politics. False bureaucratic authority substitutes for something, trust, maybe. Nationalists will be more than willing to fill the vacuum.

Europe’s fracture will feel gradual. Policy coherence will erode further. Markets will adapt and look to the Middle and/or Far East to finance the Ponzi finance on display in New York and London.

Grey Swan #5: The European Union Fractures Under the Weight of War, Debt, and Bureaucracy