Between February and March 2020, the S&P 500 lost 34% of its value in just 33 days.
$8.5 trillion in wealth gone… faster than any market crash in the previous 100 years.
I know this one personally as I was in Hanoi, Vietnam for what was supposed to be a two-week trip… but I didn't make it home for five months due to the ensuing pandemic.
I'm thinking about that period a lot right now.
Because since late October 2025, markets have been hit by two bearish forces colliding at once.
First, the Saas-pocalypse…
A roughly $3 trillion wipeout in global software stocks… sparked by fears that autonomous AI will eradicate the moat of traditional software businesses.
Then since late February, we’ve had the Israel-Iran war and the Strait of Hormuz closure. Oil is flirting with $100 a barrel… with a myriad of second and third order consequences facing us off the back of that.
And right on cue, Goldman Sachs and BlackRock have both warned this is not a short, sharp shock… they're calling it the beginning of a prolonged period of disruption.
So yes, they’re asking whether this time is indeed different.
But here’s something to think about…
We can look back at the last 15 years and say wow… what a time to be invested.
The market was straight up and to the right after all…
But let’s contrast this with actually living through it…
In 2011, just as we seemed to have turned the corner from the Global Financial Crisis… the S&P 500 fell 19.4% in a matter of months. With congress deadlocked in a debt ceiling standoff… and America's debt was downgraded for the first time in history.
Then in late 2018, rising interest rates and trade war fears sent the market down 19.8% in a single quarter. Christmas Eve 2018 being the worst Christmas Eve for stocks on record.
Then 2020, the 34% collapse in 33 days and the fastest bear market ever recorded outside of Black Monday.
Then as recently as 2022… a 24% decline as the Federal Reserve raised rates at the fastest pace since the 1980s… to fight inflation that had just hit a 40-year high.
So even in the glorious past 15 years… on 4 separate occasions we watched our portfolios lose a fifth, a quarter or a third of their value
And each time the financial media found compelling, well-sourced reasons why this time the damage might be permanent.
Yet each time they were wrong!
Because everything seems a lot smoother in hindsight… and we tend to forget the bumps along the way.
The current situation has alarming elements… we’ve got an active military conflict, an oil shock layering stagflation risk onto already fragile sentiment… and a real genuine possibility that central banks delay rate…
I'm not dismissing any of that.
But I'd note one thing the doom-and-gloom framing consistently misses this...
Equal-weighted indices… small caps… and international developed markets have quietly rallied 9–13% since October.
The investors who've navigated every one of those prior crashes without blowing up their portfolios aren't smarter than the rest.
They've just spent time around people who've seen it before.
People who remember March 2020, who held through 2022, who can tell you what it felt like to stare at a 30% drawdown and not sell.
That's the real edge, perspective.
Specifically, the kind you absorb from being in a room with people who've actually earned it.
Which is why I'm putting on Investormania II this May 14–16 in Tampa, Florida — and why the timing feels more relevant than I'd planned when we booked the venue.
Three days with investors and traders who've navigated every crash above, and some before it.
The kind of room where you sit next to someone who bought heavily in March 2020 or held through 2022, and can walk you through exactly what they saw, what they did, and what they wish they'd done differently.
Oliver