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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


The Internet Just Got Its Own Money

November 20, 2025 • Ian King

Every major tech shift has followed a similar pattern. As information moves faster, the money follows.

The telegraph made news global and opened up a world of investment opportunities. Radio, and then television, ignited a new wave of prosperity for investors. And the internet made communication instant, creating fortunes for those who saw what was coming.

Now standards like x402 are doing the same for AI and digital payments, potentially putting Jamie Dimon’s empire in jeopardy.

If you have Coinbase building the payment rails, Circle handling settlement and projects like Worldcoin and Particle Network solving for identity and wallets — do you really need a bank to validate transactions and keep track of who owns what?

All of these companies are helping to build a new layer of fintech infrastructure. And they’re all working toward an economy that runs continuously, without the need for corporate scaffolding.

The Internet Just Got Its Own Money
Jensen Huang’s Double Exhale

November 20, 2025 • Addison Wiggin

“What if you held a bond auction and nobody showed up?” That’s the perennial question plaguing a Treasury Secretary.

Yesterday’s $16 billion auction of 20-year Treasurys didn’t go as well as Bessent would have liked.

High yield: 4.706%

Bid-to-cover: 2.41 (below the 10-auction average of 2.71)

Demand is softening at the exact moment the government needs to roll over debt at record levels.

Jensen Huang’s Double Exhale
The Carry Trade Meltdown

November 20, 2025 • Addison Wiggin

With Japanese yields soaring, the returns on the carry trade are lower. Carry trades are likely getting unwound, pushing Japanese bond yields even higher.

The unwinding of the carry trade also helps explain why many individual stocks listed on the New York Stock Exchange have crashed by 40-50% from their recent highs. Investors are selling the target assets of the trade in order to pay back their yen-based loans before their profits get squeezed.

The Carry Trade Meltdown
Coinbase Wants to Dominate the Internet Capital Markets

November 19, 2025 • Ian King

On November 10, Coinbase announced a new platform that lets users buy crypto tokens before they list on the exchange.

The company calls it: “a more sustainable and transparent way for projects to distribute tokens.”

In other words, we’re moving into ICO 2.0. But this time there will be more rules.

Coinbase Wants to Dominate the Internet Capital Markets