GSI Banner
  • Free Access
  • Contributors
  • Membership Levels
  • Video
  • Origins
  • Sponsors
  • My Account
  • Sign In
  • Join Now

  • Free Access
  • Contributors
  • Membership Levels
  • Video
  • Origins
  • Sponsors
  • Contact

© 2025 Grey Swan Investment Fraternity

  • Cookie Policy
  • Privacy Policy
  • Terms & Conditions
  • Do Not Sell or Share My Personal Information
  • Whitelist Us
Beneath the Surface

Porter Stansberry: A Repeat of MicroStrategy’s +2,400% Return

Loading ...Addison Wiggin

September 12, 2025 • 5 minute, 28 second read


100 baggers

Porter Stansberry: A Repeat of MicroStrategy’s +2,400% Return

“People who bet on all of the horses in a race always have a winner, but never make any money.”

-Thomas Phelps, 100-to-1 In the Stock Market

September 12, 2025 — Michael Saylor and I know each other.

I won’t go into the details here. It’s the kind of story I don’t want to leave a paper trail on. But if you’re at this year’s conference… pull me aside and I’ll share the full story face-to-face when I can maintain full deniability.

Anyway, Saylor’s name is everywhere nowadays.

But before 2020, I’d wager most people would’ve drawn a blank.

The pandemic forever changed that though.

With the world in turmoil, the CEO of MicroStrategy found himself in a rut.

His company’s stock hadn’t moved in years and it seemed devoid of any story that could propel it upward.

While the market valued MicroStrategy at $1.5 billion, it was a far cry from the tens of billions the company had been worth over two decades earlier during the dot-com bubble.

A time when Saylor’s personal stake alone had grown to almost $10 billion.

Now, Saylor was no stranger to taking entrepreneurial risk and the attendant cycle of boom and bust.

Just a few years after graduating from MIT where he studied aeronautics and science, Saylor had launched MicroStrategy in 1989 with a few friends.

The company initially focused on boring data-mining software. But as the internet bubble took off, Saylor deftly re-positioned MicroStrategy to benefit, buying up domain names such as hope.com and voice.com.

MicroStrategy stock soared, climbing to $313 per share in 2000, more than 30x its IPO price of $12.

The bursting of the dot-com bubble in 2000 hit MicroStrategy hard. But unlike thousands of other companies that filed for bankruptcy, the company survived.

Barely.

The stock slid all the way down to $0.45 per share, a 99.9% decline from its peak.

A collapse that landed Saylor on the cover of the New York Daily News with the unenviable title of the man who “Lost $6 Billion In A Day.”

Turn Your Images On

Still he did what needed to be done to survive, settling an inquiry by the SEC and undertaking a 10-for-1 reverse split on shares of MicroStrategy.

Over the ensuing decades, the company limped along.

Saylor was searching for the “next new thing,” a trend that he could ride as he had the growth of the internet.

He struggled to find one.

Aware of cryptocurrencies soon after their emergence, he initially dismissed Bitcoin in a 2013 Twitter post as a fad whose “days are numbered.”

But now in 2020, amid the thick of COVID, Saylor found himself re-thinking his views on Bitcoin.

A keen student of financial history, Saylor grasped that the federal government would print and spend trillions to reflate the economy after the pandemic.

These measures could well precipitate inflation.

The more he studied Bitcoin, the more he came to believe it could be one of the biggest beneficiaries of this reflationary spending.

More importantly, he came to believe in Bitcoin as the digital version of “sound money.” And so later in 2020, Saylor pitched MicroStrategy’s board on an audacious plan:

Take half of the company’s $500 million cash pile and invest it in Bitcoin.

The board agreed, and MicroStrategy made its first purchases of the cryptocurrency at a price of around $11,000 per coin.

Although Bitcoin dipped to $9,000 soon after, it finished 2020 above $26,000, more than double MicroStrategy’s initial cost basis.

That was all the vindication Saylor needed to invest with conviction.

With his board’s support, he began borrowing aggressively to increase MicroStrategy’s stake in Bitcoin, taking on billions in debt to accumulate the cryptocurrency.

Drawing on his decades’ experience at the helm of a public company, Saylor tapped into all the different ways MicroStrategy could raise fiat money to plough into continued Bitcoin purchases – bank loans, convertible debt, and even secondary sales of the company’s stock.

Last year alone – four years into its foray into Bitcoin – MicroStrategy raised a staggering $23.2 billion in combined debt and equity to fund its ongoing crypto purchases.

As Bitcoin’s price has risen, it now trades for around $115,000, MicroStrategy’s stock has experienced an even greater parabolic rise.

Today the company, renamed Strategy, has a market cap of $103 billion – and investors have seen returns of more than 2,400% in a little over 5 years.

It’s one of the greatest growth stories of recent years and one that almost nobody could have seen coming.

For anyone who has ridden the MicroStrategy gravy train, congratulations.

And for those who missed it, I believe you could have a rare second chance.

Erez Kalir and I just hosted an event to unveil what we believe could potentially be the next MicroStrategy.

We detailed a company that is as little-known as MicroStrategy was back in 2020… with the very real potential for similar upside.

Just as MicroStrategy had a “boring” business before it pivoted to investing in Bitcoin, so too does the stock we want to share with you.

In MicroStrategy’s case, the legacy business was software. For our target, it’s financial services. And the underlying business is far stronger.

What’s more, the CEO is the polar opposite of Saylor… you’re never going to see him on CNBC pumping his stock or making outlandish promises.

He’s like Buffett in that way. He would never tell you to go out and buy his stock, it would be anathema to his personality.

But make no mistake: this could be one of the most lucrative investments of the next decade – a rare, truly asymmetric opportunity.

And we shared the full story with you. Including why right now could be your last chance to get in before five looming catalysts converge to potentially send the stock rallying.

Good investing.

Porter Stansberry
Porter & Company & Grey Swan Investment Fraternity

P.S. from Addison: Porter’s research is top-notch, focusing on quality investments, stories the mainstream media won’t touch – and where to find the proverbial 100-bagger stocks that can turn every $1,000 invested into $100,000.

It’s a bold statement.

Having just one asymmetric trade in your portfolio can knock years off your investment journey – either shortening the time to retirement, or allowing for a more vibrant one.

Porter’s latest research, which he dubs the most asymmetric return potential he’s ever seen, can be found here. It’s well worth a watch. Have a great weekend!

If you’d like, you can drop your most pressing questions right here: Feedback@GreySwanFraternity.com. We’ll be sure to work them in during the conversation.


When Debt Strangles Growth

October 22, 2025 • Lau Vegys

U.S. government debt is edging closer to the $38 trillion mark — now well over 120% of GDP. That puts the U.S. in the same league as basket-case economies like Venezuela, Sudan, and Lebanon. Not exactly the kind of company you want to keep.

But it makes sense: history shows that once a country crosses this threshold, things start to break — and it’s rarely just one thing. I’ve talked a lot about that in the past.

When Debt Strangles Growth
Dunning-Kruger and The Greatest Fool

October 22, 2025 • Addison Wiggin

An admission: we’re mildly obsessed with the private credit markets.

When there’s a bull market in everything — AI stocks, financials, rare earths, gold and silver — it helps to keep an eye on the plumbing.

One chart tells the tale: since 2015, bank loans to non-depository financial institutions (NDFIs) — think private equity and private-credit funds — have soared nearly 300%.

Consumer loans, residential mortgages, commercial real estate? Flat as Kansas. Post-2008, Basel III and Dodd-Frank made leveraged and middle-market lending so capital-intensive that banks stepped back.

Dunning-Kruger and The Greatest Fool
Source of the “Debasement Trade”

October 22, 2025 • Addison Wiggin

Gold dropped nearly 2% yesterday. But with the massive increase in fiat currencies globally, that’s an opportunity to buy more cheaply.

With that much cash sloshing around the system, the “debasement trade” is a go.

Source of the “Debasement Trade”
The Dominoes Keep Falling in the Move to Digital Money

October 21, 2025 • Ian King

Trillions of dollars are already being transferred and tracked on the tokenized rails that Visa, JPMorgan, Mastercard and other major financial institutions plan to scale globally in the next 12 months.

Meaning, there’s no longer such a thing as “crypto vs. the banks.”

Because the same financial giants that crypto once tried to replace are taking the best parts of blockchain — speed, transparency and programmability — and fusing them into the system they already control.

And as each domino falls, it brings us closer to a world where money moves as easily as data.

It means that by the end of 2025, digital dollars could settle more value than PayPal ever has.

So if you’re still treating digital money as “the future,” you’re already a step behind.

The Dominoes Keep Falling in the Move to Digital Money