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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 Forecast #7: A Global Debt Crisis Will Reprice Democracy

December 24, 2025 • Addison Wiggin

Wars, technology races, and political upheavals — all of them rest on fiscal capacity.

In 2026, that capacity will tighten across the developed world simultaneously. Democracies will discover that generosity financed by debt carries conditions, whether voters approve of them or not.

Bond markets will not shout so much as clear their throats. Repeatedly.

Grey Swan Forecast #7: A Global Debt Crisis Will Reprice Democracy
Seven Grey Swans, One Year Later

December 23, 2025 • Addison Wiggin

Taken together, the seven Grey Swans of 2025 behaved less like isolated events and more like interlocking stories readers already recognize.

The year moved in phases. A sharp April selloff cleared leverage quickly. Policy shifted toward tax relief, lighter regulation, and renewed tolerance for liquidity. Innovations began to slowly dominate the marketplace conversation – from Dollar 2.0 digital assets to AI-powered applications in all manner of commercial enterprises, ranging from airline and hotel bookings to driverless taxis and robots. 

Seven Grey Swans, One Year Later
2025: The Lens We Used — Fire, Transition, and What’s Next… The Boom!

December 22, 2025 • Addison Wiggin

Back in April, when we published what we called the Trump Great Reset Strategy, we described the grand realignment we believed President Trump and his acolytes were embarking on in three phases.

At the time, it read like a conceptual map. As the months passed, it began to feel like a set of operating instructions written in advance of turbulence.

As you can expect, any grandiose plan would get all kinds of blowback… but this year exhibited all manner of Trump Derangement Syndrome on top of the difficulty of steering a sclerotic empire clear of the rocky shores.

The “phases” were never about optimism or pessimism. They were about sequencing — how stress surfaces, how systems adapt, and what must hold before confidence can regenerate. And in the end, what do we do with our money?!

2025: The Lens We Used — Fire, Transition, and What’s Next… The Boom!
Dan Amoss: Squanderville Is Running Out Of Quick Fixes

December 19, 2025 • Addison Wiggin

Relative to GDP, the net international investment claim on the U.S. economy was 20% in 2003. It had swollen to 65% by 2023. Practically every type of American company, bond, or real estate asset now has some degree of foreign ownership.

But it’s even worse than that. As the federal deficit has pumped up the GDP figures, and made a larger share of the economy dependent on government spending, the quality and sustainability of GDP have deteriorated. So, foreigners, to the extent they are paying attention, are accumulating claims on an economy that has been eroded by inefficient, government-directed spending and “investments.” Why should foreign creditors maintain confidence in the integrity of these paper claims? Only to the extent that their economies are even worse off. And in the case of China, that’s probably true.

Dan Amoss: Squanderville Is Running Out Of Quick Fixes