In 1992, when I was 10 years old – my maternal grandparents passed away.
They died within a year of one another.
And after they passed away, they didn’t have much to their estate – but they did leave my sister and me a small inheritance of $5,000 each.
(That’s them in the photo; I think I am probably 7 or 8 in that picture. And yes, that is me in both a turtleneck and a mullet. You’re welcome :-)
Now, I have to imagine that most ten year old kids would’ve probably put that $5,000 in their bank account.
Instead, I convinced my parents to let me use it to learn how to invest it in the stock market.
And it changed my life.
I remember spending hours upon hours pouring over the Standard & Poor tear sheets trying to figure out what stocks to buy. I read everything that Peter Lynch wrote – including One Up on Wall Street, Beating the Street, and Learn to Earn.
This was pre-internet – but you could call an automated system through the push button landline and dial a stock ticker symbol over the phone to get a “real-time” quote (delayed by about an hour).
I would call dozens of times each day.
Over the next eight years, from 1992 to 2000, I watched my initial $5,000 investment swell to close to $85,000.
Some of my best performing investments were AMAT, INTC, and MSFT, riding the personal computing bonanza – and the corresponding semiconductor supply chain explosion powering that growth.
I wish I could say it was skill or innate investing aptitude, but the truth is this:
There was a lot of luck involved.
In fact, my timing could not have been luckier:
I started buying in 1992… And sold at almost the top of the market, right before the dot com crash of 2000.
Why?
Because I needed to cash out in order to pay for my tuition at Brown when I enrolled… in the fall of 2000.
Yeah. Pretty lucky, right?
But here’s the thing…
During this same period, 30 years ago – starting around 1995…
A respected indicator known as the Shiller P/E Ratio, which was developed by Yale economist Robert Shiller, began signaling “irrational exuberance,” predicting a significant market collapse.
The signals were undeniable: valuations were historically stretched, investor euphoria was palpable.
It felt logical to exit the market.
Yet investors who heeded that warning in 1995 missed out on one of the greatest bull market runs in market history, including the NASDAQ’s breathtaking 139% surge in 1999 alone.
And this contradiction has haunted me for decades:
If I had waited to sell – even by just a few weeks…
A good chunk of those gains would’ve been wiped out.
At the same time, if I had sold when Alan Greenspan made his famous Irrational Exuberance speech 5 years before the actual crash, I would’ve missed out on the run-up.
I got lucky.
But what would’ve been worse?
Being five years too early – or five minutes too late??
1 | Luck, Skill, and an Uncomfortable Truth.
Humans have this interesting psychological quirk:
We readily attribute our successes to skill and hard work, yet conveniently attribute our failures to misfortune or bad timing.
Behavioral economists call this “Attribution Bias.”
It’s deeply human and incredibly seductive.
It protects our ego, making us feel smart when we win and innocent when we lose.
But this bias is dangerous.
It prevents us from clearly seeing reality – particularly the hidden, outsized role luck and timing play in our lives.
In the world of investing, nothing illustrates this more dramatically than the Shiller P/E Ratio, also known as the CAPE Ratio (Cyclically Adjusted Price-to-Earnings).
Developed by Nobel Prize winning economist Robert Shiller, it famously predicted the dot-com collapse years before it actually happened.
Those who trusted Shiller’s logic too early lost untold potential profits; those who ignored it too long saw their portfolios obliterated practically overnight.
The uncomfortable truth is this:
Right Thesis, Wrong Timing (RTWT) can look exactly like being wrong – until history sorts it out.
And this is playing out in front of us right now as we speak…
2 | The Accelerating Pace of Luck and Timing in Today's World.
When Goldman Sachs hired me as a 21 year old skinny kid who was studying Neuroscience and East Asian Studies (and someone who didn’t take a single finance class in college…)
I had to prove I belonged at Goldman and “defend” my aptitude for investing by explaining my education came from actually doing it, not from learning about it in some class.
Fast forward 20+ years later, this past week in Boston I had to “defend” my aptitude for investing once again – by delivering an annual “portfolio defense” of my personal investment portfolio to my investor peer group. A super smart room of sophisticated investors..
Now, in case you’re curious – a “portfolio defense” isn’t about convincing others you’re right; it’s about identifying blindspots and exposing vulnerabilities in your investment thesis.
My former classmate at Brown, Zach Teutsch asked a great question in the comments of the thread from that Facebook post above when he asked:
Following my portfolio defense – the rigorous debate that took place in the room thereafter – was fascinating.
What stood out most clearly wasn’t disagreements about market direction.
Instead, it was uncertainty about timing.
Virtually everyone in the room agrees that something significant is coming – a major economic shift.
But is it imminent? Or will it take five years to materialize?
It’s the “Right Thesis, Wrong Timing” (RTWT) question all over again:
Is it better to be five years too early – or five minutes too late??
* * *
The recent selloff over the last few weeks erasing $5 trillion in market value is jarring nerves and stirring anxiety, only amplifying this unease.
But what makes our current moment so uniquely challenging is the unprecedented acceleration of technological change.
In our recent discussion in [Issue #033] The Coming Collapse?, I noted how AI’s disruptive force is advancing at an exponential pace that defies conventional economic adaptation.
Unlike some of the previous technological revolutions that we explored together in [Issue #028] The Return to Real Movement – like the steam engine, electricity, or even the internet – AI’s impact isn’t governed by the natural limitations of the physical world.
When the industrial revolution transformed manufacturing, implementation required building physical factories, training workers, establishing supply chains.
The pace of change, while revolutionary, was inherently constrained by material reality.
As Chris Anderson (head of TED), has famously stated:
“Atoms are expensive, but bits are free.”
Because AI advances exist primarily in the digital realm, where transformation can happen globally, virtually overnight. As I wrote:
“The pace of change during other technological breakthrough periods (e.g. industrial revolution), was largely rooted in the physical world – so there was a natural governor limiting the practical pace of change… This time, what we are seeing is happening at an accelerating, exponential pace – which our human brains have a difficult time grasping.”
And related to our discussion today around the importance of timing, that last statement is key. Acceleration creates a new timing paradox:
Windows of market opportunity that once remained open for years might now close in months – or even weeks.
The margin for timing error has compressed dramatically, making both “too early” and “too late” increasingly costly (and likely) positions.
So the question is naturally: What can we do about it?
3 | Timing's Brutal Lesson from the AI Race: The Manus Example.
This principle isn’t confined to traditional investing. It’s relevant to the offers you put out into the world, and it’s brutally evident in technology:
Just days ago, Manus Invite Codes were selling on the secondary market for astronomical sums – some paid as much as $10,000 simply to join the beta.
As an aside (and not to brag… okay just a little.) I literally *just* got access to Manus minutes ago, literally while I was writing this newsletter (I’m not even kidding…)
And no, before you even ask, I’m not going to sell my access code like some cut-rate AI courtesan :-)
The point is this:
This rapid-fire evolution underlines a new reality: timing windows have compressed. Being early by just months – or even weeks – can feel as disastrous as arriving too late.
(Like those who dropped $10K to get “early” access to something that they could’ve waited literally another day or two to get access to for free.)
The Manus example parallels what we’re seeing across the entire AI landscape. As noted in “The Coming Collapse,” the pace of technological advancement at this moment is breathtaking:
“The disruption that AI is having – and the accelerating pace of technology we’re seeing landing on our doorstep in just the last week – China’s DeepSeek, OpenAI’s Operator, etc. etc… Is naturally putting virtually every (current) white collar profession at risk of being obsolete – perhaps far sooner than many may have thought even just a few months ago…”
What’s particularly unsettling about this acceleration is how it defies our intuitive sense of pacing.
Human cognition evolved to understand linear change – each step roughly equivalent to the last.
But technological progress, especially in AI, is fundamentally exponential.
Each advancement builds upon all previous ones, creating a curve that starts deceptively slowly before suddenly rocketing upward at a pace that feels impossible to track, let alone anticipate.
And it’s precisely this exponential acceleration that makes timing so critical and so difficult. The gap between “too early” and “too late” shrinks with each technological iteration.
In my practice, I serve as Strategic Advisor to a small group of entrepreneurs, and what I tell them based on my experience 7x Inc. 5000 / 2x Exits / Investing / etc. is this:
Strategic positioning in a world of uncertainty isn’t about eliminating risk – it’s about distributing it intelligently across different possible futures. It’s about building resilience against timing errors while maintaining exposure to your core thesis.
BTW – As an aside, if you have interest in working with me 1:1 as a private client – I am considering opening up one (1) private client spot later this month. You can get your name onto my priority notification list here. (And if you really want that spot sign up here now. I expect that there will be more demand than I can accept.)
Want to work with me one-on-one?
Join my private client waitlist and be first to know when I have availability for new 1:1 clients.
4 | Timing Anxiety in Current Markets: What's Really Happening?
Today, as we see volatility rattling markets – NASDAQ and S&P movements swing widely amid investor anxiety – it feels reminiscent of those uneasy days in the late 1990s.
Readers frequently ask me: “Is this the collapse you mentioned earlier? How long will it last? Where are the safe havens?”
The truth is uncomfortable but simple:
Nobody truly knows with certainty.
My dear friend Dr. Ruth Buczynski likes to say that certainty is the enemy of intellectual humility.
What we do know is that times of extreme volatility and anxiety often mark transitions – moments where the market is recalibrating.
And these are often the times of greatest opportunity – like for example, my private client whom I’m advising who just 3x’d his target revenue on a product launch this month that generated $2.7M in gross revenue – in part because of the “Zig when they Zag” Contrarian Strategic Moves we designed together…
The technological thesis – that AI will fundamentally restructure employment across virtually all knowledge work – seems increasingly certain.
But the timing?
THAT remains the multi-trillion-dollar question.
Will this transformation unfold gradually over decades, allowing for social adaptation and new forms of employment to emerge?
Or will it accelerate so rapidly that millions find themselves displaced before economic structures can evolve to accommodate them?
Each scenario demands radically different preparation, yet the underlying thesis remains identical.
This is precisely why timing, not directional correctness, has become the central strategic challenge of our era.
What makes this particularly difficult is that we have no historical precedent for technological change at this pace and scale. We’re navigating truly uncharted waters, where traditional economic models offer limited guidance. As I noted in [Issue #033]:
“We are in uncharted territory. And in unprecedented times like this when ‘letting history be our guide’ can only take us so far… Imagination can be more important than analysis.”
5 | So, Is it Better to Be 5 Years Too Early or 5 Minutes Too Late?
Reflecting back on my ten-year-old self, staring at S&P tear sheets and trying desperately to figure out if I was “right” about the market, I realize I didn’t fully grasp how much timing mattered.
(I mean, I was just a kid.)
But today, 30 years later – after scaling multiple companies, multiple exits, and as both an investor and advisor – what I’ve learned is this:
It’s neither inherently better nor worse to be early or late. What matters most is knowing which side you’re erring on – and why.
It’s like this:
If you’re early, patience and resilience become your superpowers.
If you’re late, agility and humility are what you’ll need most.
(It’s worth reading those last two lines again.)
Because either way, clarity about your timing biases provides a profound advantage.
The question itself – early or late – is actually less important than the reflection it triggers, IMHO. Admitting uncertainty isn’t a sign of weakness; it represents intellectual maturity. In fact, it’s wisdom.
Because recognizing the hidden, critical role luck and timing play is exactly how you begin to master them.
In our current moment of accelerating technological change, I believe this awareness of timing’s centrality has never been more crucial.
The AI revolution that we’re just entering into presents us with a timing paradox more consequential than any in modern economic history. As I wrote in “The Coming Collapse”:
“Anyone who expresses certainty around future events over which they do not have control – is someone to be viewed with deep skepticism… Think in terms of the range of future possibilities – particularly the ones not getting headline attention in the media. And make preparations rooted in probability… Not a singular, inevitable black and white future…”
As the poker player Annie Duke wrote in her book, Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts
This approach – embracing probability rather than certainty, preparedness rather than prediction – offers the most robust strategy for navigating the complexity of “timing”.
Build optionality into your life and work. Make moves and build assets that retain value across multiple possible futures. Embrace scenario planning rather than single-point forecasting.
(In other words, ask yourself: What is the percent chance in your estimation that your prediction will play out within the timing you’re predicting? 10% 50% 80%? And then, what’s your level of conviction in that prediction?)
Perhaps most importantly, maintain “intellectual humility” about timing even while holding strong directionalconvictions.
In a world changing as quickly as ours, that might be the most valuable strategic advantage you can have.
So when faced with that impossible question – early or late?
Perhaps the wisest answer isn’t choosing one or the other, but making strategic moves to survive and thrive either way no matter what.
Those are the moves I’m making.
In my portfolio.
On my farm.
In my business.
And with my clients.
* * *
Okay, we’ll wrap this one up for today.
Have a great rest of your weekend…
And remember to hug the ones you love.
Until next week,
Ryan :-)
P.S. Going forward, I’m considering sending weekend access to The Digital Contrarian only to members subscribed to my new Substack…
(Possibly, I haven’t decided yet…)
But just to be safe… If you enjoy reading this newsletter over the weekend, and you haven’t yet subscribed to my Substack (it’s 100% free) I highly highly recommend you do that (it takes 30 seconds).
Simply do the following:
Step 1: Subscribe to The Digital Contarian Substack:
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And that’s it, you’re done! :-)
P.P.S. Lastly… So what do you think??
Is it better to be five years too early? Or five minutes too late?
I’m curious what you think. SHOOT ME AN EMAIL to let me know – I read every single reply that comes through (even when my bandwidth is limited and I’m not able to immediately reply to each and every message). Let me know your thoughts :-)
