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

  • Free Access
  • Contributors
  • Membership Levels
  • Grey Swan Forecasts
  • Video
  • Origins
  • Sponsors
  • Contact

© 2026 Grey Swan Investment Fraternity

  • Cookie Policy
  • Privacy Policy
  • Terms & Conditions
  • Do Not Sell or Share My Personal Information
  • Whitelist Us
Swan Dive

How to Ruin a Business Without Really Trying

Loading ...Andrew Packer

July 18, 2025 • 4 minute, 3 second read


Integrityinvesting principlesmanagement

How to Ruin a Business Without Really Trying

“It takes 20 years to build a reputation, and five minutes to ruin it,” Warren Buffett once warned.

Perhaps that’s why social media has been flooded with news headlines, coverage, and memes since Wednesday night.

That’s when the CEO of a tech startup called Astronomer was caught on the jumbotron camera at a Coldplay concert, enjoying what looked like an intimate moment with what appeared to be the company’s HR manager.

Not present? Their respective spouses.

Astronomer is one of many unicorn companies today. It’s privately held and valued at over $1 billion.

That means there are dozens of investors, from angel investors to hedge funds, who put their capital – and their reputation – on the line to invest.

The latest filing notes that Astronomer has about 370 employees.

Today, that’s all in jeopardy. The damage done to the company by the actions of two of its key employees is all that it took.

Turn Your Images On

Imagine finding out that your spouse is either cheating on you… or, worse – they’re a Coldplay fan.

It’s most likely that the event, which became a social media storm on top of all the other drama this week, will blow over. The CEO and HR manager will likely be allowed to step down.

The company will likely move on. But even as this viral moment fades into memory, the impact may endure for years – with future investors being more hesitant to invest.

Management: A Make-or-Break Factor In Investment Success

Management is just one facet of any investment decision.

But it’s a challenging one because it doesn’t appear on the balance sheet. It requires a deeper dive beyond the numbers.

Chances are, if you’re a momentum trader, you just watch the price and buy as long as it’s been going up.

Value investors look to determine the total sum of a company’s assets and discounted future earnings, and look to buy at a discount to that figure.

Most likely, you’re somewhere in between. You own some value plays. You trade some momentum stocks. Life is good.

But every once in a while, you’ll run into the Enrons of the world – the companies whose behavior leads to a material risk to your investment.

Sure, it helps to be diversified.

But at the end of the day what really matters is management.

Ultimately, a company CEO has obligations beyond making decisions in boardrooms. They need to behave in a way that reflects well for the company that they run 24/7. They need to do the right thing, even when nobody is looking.

We used to have a word for that. It’s called integrity.

Build Your Community With Integrity

Integrity is in short supply today.

Corporate CEOs have to chase quarterly results, and the temptation to cut corners is great. We’ll see that play out with earnings season over the next few weeks – look for companies with a suspicious number of “one-time” events – chances are they aren’t one-time.

Members of Congress use the information they get from committee meetings during their part-time hours to substantially outperform the stock market. Until that’s fixed with clearer legislation and term limits, at least investors can follow along, albeit belatedly.

Families are working harder and harder to make ends meet, having their purchasing power eroded by inflation, and by the machinations of a central bank concerned with propping up asset prices, not wages.

It’s tough. I get it. But that’s also why it’s worthwhile. The road less taken is a more challenging one, but a more satisfying one.

This is why it’s crucial as an investor to look at who you’re investing with. Someone with a good idea and integrity will help you grow your wealth far more than someone with a great idea but who has no integrity.

And why it’s important to keep some of your wealth in honest forms of money like gold and, yes, bitcoin.

And there’s another theme here as well: The truth. It always comes out. Not always on the jumbotron, or on the front page of a national newspaper. But if you always live your life under the assumption that anything you do will be headline news – or the darling of social media – you’ll focus on the positive ways that can turn out.

~ Andrew

P.S. Integrity, trust, truth – themes we’ve touched on this week as we look at the unfolding news – are qualities always worth watching.

Issues of corporate governance – and wild stories about CEOs and management teams running amok – aren’t unusual.

In fact, real-world examples of corporate malfeasance have become inspirational for the series of novels that I’ve written. But what happened at that Coldplay concert this week sounds stranger than fiction.

Your thoughts? Please send them here: addison@greyswanfraternity.com


The Hindenburg Five

February 24, 2026 • Addison Wiggin

The stock market “rebalancing” is a polite way to put it. Energy and health care are getting a healthy boost. But tech hardware and software makers are still getting dressed down and have been asked to report to the principal’s office.

The great rotation underway has triggered a series of “Hindenburg Omens.” Five have occurred in recent weeks.

The Hindenburg Five
Piercing The Veil

February 23, 2026 • Addison Wiggin

The S&P 500 has traded in a 3.7% range over the past two months — less than half the 20-year median of 8.6%. One of the tightest ranges in modern history.

In trader parlance, the indexes are “flat,” a setup that often materializes before a sell-off at the top after a multi-year bull market.

Goldman Sachs told its own traders to be aware that institutional trading activity resembles a VIX reading near 35. Rather than a reading of 20, where the VIX has been trading over that same 2-month period.

The U.S. software ETF, IGV, tested its April 2025 lows last week and trades roughly 35% below its peak. The “SaaS-pocalypse” in software companies reflects the fear of Citrini’s 2028 scenario happening in real time.   That divergence now exceeds the spread seen at the peak of the Great Financial Crisis.

Under the surface, the “great rotation” we wrote about last week is threatening to widen.

Piercing The Veil
Oh. Canada

February 23, 2026 • Addison Wiggin

Despite its overly-educated 40-million-plus population, on a GDP per capita basis Canada is null. Collectively, the Great White North would rank as America’s second-lowest state, coming in above Mississippi, but below Alabama.

Oh. Canada
Matt Milner: SpaceX + xAI: What It Means for You

February 20, 2026 • Addison Wiggin

SpaceX is the most valuable private startup in history — and if its success continues, it might become the most valuable public company in history.

After all, as Musk famously said in 2023, “I have never lost money for those who invest in me and I am not starting now.”

For investors, SpaceX has been a wild, joyful ride — and now the journey continues!

Matt Milner: SpaceX + xAI: What It Means for You