I’m here with my family in Boston, MA this weekend…
Technically Cambridge…
For the 2025 NuVuX Summit, a disruptive educational model founded on MIT campus a decade ago, and a program our son was invited to participate in.
NuVu is an innovative educational model that empowers future leaders with skills to become independent thinkers and tackle the world’s biggest challenges through hands-on, creative projects.
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And after we got into town last night…
On a whim – about an hour before tipoff – Tylene and I decided to take the boys to their first ever Boston Celtics game, and splurged on some great seats just a few rows off the parquet floor…
Now, I’m not gonna lie…
These tickets weren’t cheap.
BUT after enjoying the experience as a family…
They were 100% worth it.
Why?
What’s the “financial calculus” and justification?
Well…
In [Issue #042] How to Keep Your Head Straight, I shared a bit of insight into my personal Investment Policy Statement…
And within that IPS, there’s an entire section devoted to a framework I use for how to think about investing in an annual “Experience Fund” for your family.
In the book Die with Zero, (which I read a few years ago and recommend), Bill Perkins makes a compelling case for the value of investing in memories earlier in your life because of the compounding nature of their value.
The earlier the memory is formed, the more time in your life (and in the lives of your loved ones) you get to enjoy that memory, and thus the more valuable that memory becomes.
Additionally, studies show that when asked about their best childhood memories, most adults cite a vacation or trip, often with their parents or grandparents.
So I believe (admittedly subjectively) these are all experiences worth investing in – because they pay dividends for years to come.
But here’s the question:
If we suddenly find ourselves in an economic downturn – and systemic rebalancing of world order due to trade tariffs (complicated further by disruptive impact of AI)…
Does everything change??
In other words:
Do we need to re-think the strategic decisions we’re making right now in our portfolios, our businesses, and our lives…
*IF* the world we face in the next 12-18 months is radically different from the world we live in today??
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It is a question I’ve been thinking deeply about.
And one I’ve been researching intensely over the past week.
So I thought I would share some of my latest thinking…
(Along with a few surprising things I’ve discovered…)
And a few important ideas YOU may want to bring into your awareness as you make plans for your business over the next 18 months.
1 | Fear & Loathing in Mar-a-Lago.
On Tuesday this week – in the midst of tariff-induced market turmoil – the DJIA moved 2000 points in response to Chinese tariff retaliation…
And in the middle of it all, I received a voice memo from a concerned private client in my advisory practice. Here’s what he asked:
“Ryan, with the market crashing, I’m starting to have clients texting me that “the sky is falling” and asking me to reduce my prices. Should I be making changes to my marketing and pricing model if we suddenly have a significant economic downturn? Your thoughts?”
My response?
Don’t make a knee-jerk reaction.
Take a breath.
And pause.
(A good practice in general.)
Because markets don’t free-fall forever. They tend to stabilize.
And sure enough – by the end of the week, after markets had made up about half the ground lost since the start of the month…
Fear and panic had largely subsided.
(At least temporarily…)
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But the bigger truth remains:
The level of uncertainty in the world right now is unlike anything we’ve seen since the early days of COVID.
And following last week’s [Issue #042] How to Keep Your Head Straight When the World Goes Sideways…
I wanted to dig deeper into the second- and third-order effects of multilateral trade tariffs.
To better advise my clients.
To refine my own investment thesis.
And to understand:
Could these trade tariffs actually be tactical maneuvers from a larger political playbook?
And if so…
What strategic moves should we be making in response – as business owners and investors?
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As always:
To understand the present…
We need to first understand the past – and what brought us here.
In other words:
Be Curious. Ask Questions. Seek Truth.
2 | The Changing World Order Taking Place Right Beneath Our Nose.
The opening photo in this week’s issue of The Digital Contrarian…
(The one with my son staring at the skeletons hanging from the ceiling…)
Was taken this weekend at the Harvard Museum of Natural History…
Looking up at that ceiling was a humbling reminder that even the mightiest entities on this planet are constantly at risk of extinction…
And that doesn’t just apply to biological species…
But also industry-leading companies…
(As we explored in [Issue #037] Wake Up Call: The Illusion of Permanence…)
As well as reserve-currency-issuing sovereign nations…
(As we will explore today…)
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This past week…
After finishing Nexus: A Brief History of Information Networks from the Stone Age to AI by Yuval Noah Harari…
I shifted my attention to Ray Dalio’s second book:
(A very timely read, given what’s unfolding globally…)
While Changing World Order offers valuable insights into the relationship between short- and long-term debt cycles…
A topic that we explored in [Issue #040] Make Your Move (Before It’s Too Late…)
It’s also a deep cut.
And for that reason, I don’t think it’s required reading for everyone.
However…
Dalio created a great 45-minute YouTube Video that summarizes the main ideas in the book – and I highly recommend you take a few minutes to watch it (even if this isn’t typically your jam…)
NOTE: I believe this dynamic is so important, I watched this video with my boys to help them understand this aspect of our complex global system.
I recommend watching it in the context of today’s conversation…
Because it provides essential context for understanding the timing and rationale behind trade tariffs – and the broader geopolitical game being played right now.
And once you understand that…
You’ll be better equipped to anticipate what’s coming – and respond accordingly in your business and marketing.
Let me explain…
3 | The Secret "Tariff Playbook" Sending Shockwaves Across the Internet.
ICYMI – There is an economic paper that’s been sending shockwaves across the internet:
It’s a 41-page paper by Stephen Miran – a Harvard economist, senior advisor to Trump, and chair of his Council of Economic Advisors.
He’s widely considered the brain behind the current “Trump Tariff Turmoil.”
In this paper, Miran outlines a compelling U.S.-centric case for expanded trade tariffs – and reveals a multi-step tariff playbook that (as you’ll see in a moment) we are likely in the midst of watching unfold.
(Hint: What feels like chaos might actually be a carefully choreographed sequence of moves…)
As I dove deeper this week, curiosity got the best of me…
So I took a few hours to read the paper.
(Warning: It is dense.)
But once again – YouTube to the rescue.
This video distills the paper’s main arguments and explores the broader financial and economic implications in plain English:
Here’s the tl;dr:
The trade tariffs we’re seeing today are Phase 1 of a 3-phase strategy…
A strategy designed to play out over the coming months.
Which gives us insight into how to prepare…
And what moves we might want to make in our businesses right now.
4 | So What Strategic Business Moves Should We Be Making?
You may have heard that Trump claimed in a speech that Charles Schwab (the person, not the firm) made $2 Billion in a single day in the middle of this market chaos.
And on an infinitely smaller scale, I have friends who decided to enter the market last Friday when the market hit the (current) bottom, and have scaled their positions since.
In short:
The short term volatility we’re likely to experience in the coming weeks and months will create additional opportunities like this…
Not just as an investor, but also as a business owner…
But in order to take advantage of these opportunities, you need to have three (3) things solidly in place:
#1: Your Overall Economic Thesis
After doing the recommended reading in this email (or at a minimum watching the recommended videos)…
And after considering the available data, what do YOU believe to true and what’s YOUR overall thesis?
For example:
Do you believe that U.S. on-shoring of manufacturing will actually happen in response to tariffs – and that we’ll see $3,500 iPhones as a result?
Or do you believe that any increased costs associated with tariffs (say, on China) will be offset by a corresponding weakening of foreign currencies (say, the RMB relative to the USD), due to balancing economic forces?
Or alternatively, do you believe this is simply a tactical move on the geopolitical chessboard – designed to both appease a populist base and pressure trade allies into becoming economic vassal states?
Or how about this one here:
Do you believe the uncertainty created by this tariff turmoil – along with slowing economic activity – was a calculated move designed to pressure central banks into cutting interest rates, thereby stimulating the economy?
(And thus, lower interest rates are likely on the horizon…)
Or do you believe it was a profiteering move – effectively a sovereign form of insider trading – designed to line the pockets of a few politicians and their cronies, further contributing to the widening wealth gap, the likes of which we haven’t seen since the Gilded Age?
(Or a bit of both?)
These are the kinds of issues you want to have a position on – to inform your overall economic thesis.
Which, in turn, informs your market thesis…
Which, in turn, informs your industry outlook for the business you find yourself in…
So you can decide what strategic moves to make over the next 18 months.
(Or have a personal strategic advisor in your corner – someone who offers a grounded perspective on how to think about all this in relationship to your business – a role I serve for my clients…)
Which brings us next to…
#2: Your Watch List
You need to have a “watch list” of opportunities you’re actively tracking – so you’re ready to pounce when the right conditions align.
For example:
In investment terms…
This might include alerts or limit orders on public securities you’re watching – ready to move once their price or yield hits a certain level – using tools like Seeking Alpha, or similar.
In business terms…
It might include ideas for new product lines or services you could launch once the timing is right – or in response to external changes…
Or a list of strategic partners (or even acquisition targets) you’re keeping a close eye on.
But in either case, what’s critical is having your watch list organized, prioritized, and actionable – so that when the window opens…
You’re ready to move.
Because sometimes (as we saw in the markets last Friday)…
These moments can be shockingly short-lived.
Which brings us to…
#3: Dry Powder / Spare Capacity
You can’t pounce on opportunity if you’re redlining.
You need to maintain spare capacity.
You need to keep cash on hand that’s ready to deploy.
You need to preserve mental space, so you’ve got time to think – and aren’t stuck in reactionary fight-or-flight mode.
Because it’s only when you’ve got breathing room…
That you can be opportunistic.
When you’ve got these three ingredients in place:
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A clear Thesis
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A well-organized Watch List
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And some Dry Powder
You’re primed to seize opportunities as they arise…
No matter what gets thrown our way over the next 12–18 months.
5 | Lastly, Remember to Shine the Flashlight Where Nobody is Looking...
One last thought I’ll leave you with:
Whenever a single news story overwhelmingly dominates the headlines – and it’s one that’s been artificially manufactured by man…
(Meaning: it’s not a natural disaster…)
I can’t help but wonder:
Like a magician using sleight of hand and misdirection to steer our attention:
“Look over here! Look over here!”
Is there another story unfolding quietly in the background – one we’re unknowingly being distracted from?
As a contrarian and independent thinker, I believe it’s worth pausing to reflect on that…
Especially before we wrap our conversation today.
Because in the ongoing quest to:
Be Curious. Ask Questions. Seek Truth.
Don’t forget to shine the flashlight where nobody else is looking…
And remember to look up.
You might be surprised with what you find.
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Okay, I’ll leave you with that for now…
As always, I welcome your thoughts…
And after you’ve taken a moment to watch the recommended videos – Please do take a moment to shoot me an email (I read every email.)
And in the meantime…
Be sure to hug the ones you love.
Until next week,
Ryan :-)
