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Ryan Levesque

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The Digital Contrarianâ„¢

Ryan Levesque

Issue #042

| The Digital Contrarianâ„¢

How to Keep Your Head Straight…

When The World Goes Sideways.

Ryan Levesque

13 min read

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Earlier this week (days after taking this photo in front of the White House, while Tylene and I were in Washington DC for a wedding), President Trump announced sweeping new tariffs targeting imports from a wide range of countries.
 
 
Headlines screamed.
 
Nerves frayed.
 
Portfolios buckled.
And I found myself doing something unexpected:
 
Not panicking.
 
Not worrying.
 
Not freaking out.
 
Instead, in the middle of the market turmoil…
 
I opened up a blank document and started writing.
 
And what came out was something I’d been meaning to document – for years.
 
Something that (if I’m honest) I avoided because, while much of what I wanted to write was “in my head”…
 
The process of actually getting down on paper felt overwhelming.
 
So I procrastinated.
 
But when the market panic started, it was the stimulus I needed to finally sit down and draft my personal Investment Policy Statement (IPS).
 
What’s THAT??
 
And more importantly, what’s it got to do with YOU?
 
Well today, I want to share what I believe may be insightful…
 
And more specifically…
 
Why I believe taking a few minutes to document YOUR strategic decision-making framework…
 
(Whether for your investments, your business, or your life…)
 
…Is one of the most important steps you can take to keep your head straight when the world goes sideways.
 
Especially in times like this…
 

1 | Why This Moment Felt Familiar (& A Hard-Earned Lesson).​

Back in [Issue #039] Right Thesis, Wrong Timing, I wrote about my early investing journey in the stock market, transforming $5,000 into $85,000 during the bull market run of the 1990’s….
 
More recently I hosted a live session entitled “My $70M Mistake: What I Wish I Knew Before Selling My Company…” (A deal with multiple millions of dollars at stake…)
 
In both of these pieces, we explored the important role of luck and timing in success. And as I shared on that live call Zoom session:
 
“Sometimes when you sell, is actually more important than what you sell.”
 
(A reminder that’s worth writing down…)
 
* * *
Now, a few months ago…
 
Back in [Issue #027] Your Strategic Content Ecosystem I wrote how here on the farm we have an expression:
 
“There are no secrets in the snow.”
 
And while spring is (finally) upon us as I write this issue today…
 
In the long Vermont winter, here on the farm when fresh snow falls, every movement of every creature leaves a trace.
 
The fox can’t hide its path. The deer can’t conceal its track. The truth of what happened is there for anyone to see.
 
Market corrections are like fresh snow.
 
They reveal the tracks of every decision you’ve made:
 
The good ones.
 
The bad ones.
 
The lucky ones.
 
And the not-so-lucky ones.
 
It’s been over 30 years since my first trade as an investor…
 
And in the last 30+ years, I’ve experienced some big wins – and some big losses. And each one of those losses has left a mark on me.
 
But collectively, those losses have also left something else:
 
  • A set of beliefs
  • A scar-tissue-level intuition about risk
  • A backlog of lessons (Like “when is often more important than what“) that I said I’d one day codify into a clear investing strategy
 
So when the market panic hit this week, I knew it was time.
 
Not to react.
 
But to write.

2 | Okay, So What IS an Investment Policy Statement (And Who Needs One?)​

An IPS might sound like the kind of thing only big institutions create – university endowments and pension funds with billions in assets.
 
But I’ve come to see it as something much more personal. (And much more powerful.)
 
Your IPS is your personal investing rulebook.
 
And it’s not about trying to predict the future. It’s about deciding how you’ll behave when the future goes sideways.
 
Think of it like a Constitution for your wealth. A document that transcends your emotions and protects you from your worst impulses.
 
For me, the IPS covers things like:
 
  • My financial objectives (income vs. growth, timelines, target rates)
  • Income needs (how much I need for lifestyle and running the farm)
  • Portfolio structure and asset allocation (the non-negotiables)
  • Risk management rules (position sizing, loss thresholds)
  • Liquidity planning (how much stays liquid, and in what form)
  • Guardrails for behavior (what to do – and not do – in a crisis)
  • A system for classifying and tracking each investment (more on this below…)
 
But here’s what I want to make clear:
 
A document like this isn’t just for investing.
 
A good IPS is just one version of something every contrarian thinker needs:
 
A written framework that governs how you make decisions – especially when the heat turns up.
 
If you run a business, it might be your 18-month strategy doc.
 
If you’re planting a farm, it might be your crop rotation, seed start schedule, and livestock plans…
 
If you’re raising kids, it might be your Core Family Values (as I wrote about in [Issue #034] How to Become Anti-Fragile…
 
The form doesn’t matter. 
 
The function does:
 
When things get loud, the written plan keeps you grounded.
 
So I thought I would share with you here….

3 | Six Core Principles from My Personal IPS​

What follows are six (6) examples – based on real decisions I’ve documented in my IPS…
 
BTW – This is list is by no means exhaustive. I’ve taken a representative sample of what amount to be dozens of documented principles in my IPS.
 
For the purposes of this issue of The Digital Contrarian, I’m using hypothetical portfolio sizes ($1M to $50M) to illustrate these principles, but the ideas apply no matter where you are on the spectrum.
 
And just to be clear:
 
This isn’t financial, investment, or tax advice.
 
This is just a window into how I think.
 
Take what’s useful. Leave the rest.
 
Okay, here goes…

Principle #1: Investment Check Size Discipline

“Don’t write checks too small to matter or too big to recover from.”
Early in my investing journey, I made a classic mistake: I spread myself too thin across too many opportunities, believing I was “diversifying.”
 
The truth?
 
I was creating an unmanageable mess.
 
At a $1M liquid net worth, a $25K private real estate deal is 2.5% of your portfolio.
 
That’s meaningful.
 
At $10M, that same check is 0.25% – and if you’re still writing $25K checks, now you’re managing 40 line items just to deploy 10% of your capital.
 
I’ve now established clear position size minimums and maximums for every asset class, based on their risk profile and my total portfolio size.
 
My investment philosophy is that the check size should be big enough to move the needle. But small enough to cut if it goes south.
 
This rule forces me to be extraordinarily selective.
 
And it brings clarity to opportunity screening.
 
Especially in high-velocity markets (like with AI, for example) where new “opportunities” show up every week.
 
When you know your check size, you automatically filter out the noise.
 
Which takes us to…

Principle #2: No More Unsecured Debt

“I’d rather earn 7% with sleep than 20% with stress.”
Some lessons you have to learn the hard way.
 
I once invested $750K into a collection of high-yield debt instruments offering 20%+ interest, paid via monthly coupon.
 
They were unsecured.
 
The company went bankrupt.
 
I lost all of it.
 
(Yeah, that was pretty rough.)
 
But as tennis great Roger Federer stated at the commencement speech he delivered at Dartmouth College last year:
 

“When you’re playing a point, it has to be the most important thing in the world, but when it’s behind you, it’s behind you. This mindset is crucial. Because it frees you to commit to the next point, and the next point after that.”

 
(BTW – Check out the clip at 13:14 – There’s a great lesson in there that I thought was so good, I shared with my boys recently before bed…)
 
Today, I have a hard rule:
 
If there’s no tangible, enforceable collateral on a debt deal – I pass.
 
If someone dangles a 20% interest rate without offering hard assets as a backstop (in a senior, secured position), there’s a reason. The market has already priced the risk.
 
It’s not just about the yield. It’s about asymmetric downside.
 
Sleep-at-night risk matters more to me now than chasing the last basis point.
 
(And this isn’t just an investing principle – It’s a life principle.)
 
In this world so obsessed with optimization and “squeezing out every drop,” there’s a forgotten wisdom in building margins of safety.

Principle #3: No More Diligence by Proxy

“Just because someone smart is in the deal doesn’t mean they did their homework.”
This one took me having a million dollar loss to learn.
 
A few years ago, I invested in a deal because someone super smart that I deeply trusted was also in that same deal.
 
But I didn’t ask: Did they really dig in? Did they do their diligence? Or were they just following their trusted friend, who was following their trusted friend?
 
What I discovered was that there can often be 10 (or 100) investors in a deal, and none of them have actually done truediligence. 
 
Everyone assumes someone else had.
 
So today, my rule is simple:
 
If I’m not doing deep diligence – or paying someone I trust to do it specifically for me – I don’t invest.
 
(At the same time, as part of that diligence – I like to see institutional-grade sponsors, a material general partner (GP) co-investment, and ideally an institutional-level lead investor in the deal. e.g. CalSTRS (the California Teacher Pension Fund) is going to a much more thorough level of diligence than I could ever hope to do on an individual deal.)
 
That said, the bottom line is this:
 
Being contrarian means thinking independently. 
 
Not outsourcing your judgment to the crowd, no matter how impressive that crowd might be.

Principle #4: Liquidity Is a Timeline, Not a Binary Label

“A ‘redemption window’ is not ‘liquid’ when you need it now.”
I used to think in binary terms with my portfolio: liquid vs. illiquid.
 
Cash was liquid. 
 
Real estate wasn’t. 
 
Everything else fell somewhere in between.
 
Now, in my IPS I categorize every dollar by how quickly I can access it:
 
  • Tier 1:< 24 hours (cash, money market accounts)
  • Tier 2:< 7 days (T-bills, ETFs, public equities)
  • Tier 3:< 30 days (private credit, life insurance loans)
  • Tier 4:> 30 days (real estate, private equity, venture capital)
  • Etc. etc.
 
Why does this matter? 
 
Because in moments of crisis (or opportunity), timing is everything.
 
In February 2020, when markets suddenly crashed during the early days of COVID, I couldn’t access some funds that I thought were “liquid” because redemption windows suddenly changed.
 
Meanwhile, I discovered that some “illiquid” investments had features (like lines of credit I could take out against them) that made them more accessible than I’d thought.
 
This framework changed how I think about risk buffers, dry powder, and emergency planning.
 
Which takes us to…

Principle #5: Diversify Way Beyond the Obvious

“Asset allocation is just the beginning…”
Most investors diversify across asset classes and limit exposure on individual positions. 
 
That’s basic.
 
But after living through multiple cycles, I’ve added additional axes of diversification to my IPS. Like for example:
 
  • Institutional Custody: No more than 20% with any one custodian (e.g., Fidelity, Morgan Stanley, Wells Fargo, etc.)
  • Currency Exposure: Maintain 10–15% in non-USD assets
  • Insurance Compliance: Stay within FDIC and SIPC account limits
 
This might sound paranoid. Until it isn’t.
 
When Silicon Valley Bank collapsed in 2023, many entrepreneurs had business and personal accounts there – well beyond FDIC limits. When the dust settled, most got their money back, but the interim weeks were brutal.
 
These aren’t sexy rules. But they’re foundational.
 
And in moments of systemic risk, they might be the difference between temporary pain and permanent loss.
 
Contrarians think not just about what everyone sees, but what few are considering.
 
And this takes us to…

Principle #6: Classify Investments by Status, Not Just Type

“A position with no plan is a liability dressed as an asset.”
Most portfolio summaries sort by asset class or ticker symbol. 
 
That’s convenient for accountants, but almost useless for decision-making.
 
In my IPS, every investment has a status tag:
 
  • S1 – Allocating: Building position, actively adding
  • S2 – Holding: No action required, harvesting income
  • S3 – Under Review: Something feels off – watching closely
  • S4 – Exit: Wind it down or write it off
 
This simple classification forces me to tell the truth about what I’m holding.
 
It also makes quarterly reviews easier. I’m not sorting by type – instead, I’m sorting by intent.
 
And in investing (like in life), intent is everything.
 
Rather than treating my entire portfolio as a single entity to be judged by some aggregate return number, I now see it as a collection of stories – some still being written, others ready for their final chapter.

4 | Why This Goes Beyond Just Money​

Let me tell you a secret:
 
This newsletter isn’t really about money. 
 
Instead, it’s about clarity.
 
When things get shaky – whether in markets, business, or personal life – like with this whole Tariff Situation – it’s easy to start reacting emotionally.
 
Whether that’s chasing the hot thing in an opportunity cycle.
 
Or jumping out too early in a relief cycle.
 
Making decisions from a place of fear rather than conviction.
 
NOTE: I wrote briefly about Relief vs. Opportunity Cycles in this Facebook Post here below from last month, in case you’re curious.
But the antidote to emotional decision-making is simple:
 
Write down the rules when you’re calm – so you can follow them when you’re not.
 
It’s no different than what I teach my boys about dealing with pressure situations in sports or life:
 
“The time to prepare isn’t when you’re in the moment. It’s all the practice you’ve put in beforehand.”
 
Your version of an IPS will look different than mine.
 
(And it might not be about money at all.)
 
But if you don’t have a strategic decision-making document – one that’s updated, real, and brutally honest – consider this your sign:
 
Take ten minutes.
 
Open a blank doc. 
 
Write your version of clarity.
 
Then save it. Not just for today. But for the moment the headlines start screaming.
 
Because that’s when it matters most.
 
And this is how to keep your head straight when the world goes sideways.
 
Remember:
 
When it comes to investing – no matter what market conditions we’re facing….
 
There’s no better investment – than investing in yourself.
 
And that is exactly what this is.
* * *
Okay, I’ll leave you with that for now…
 
Remember to hug the ones you love…
 
And until next week,
 
Ryan :-)
 
P.S. I’m considering hosting a session that teaches my exact process for developing a strategic decision-making framework like the IPS I described today…
 
(As well as a TEMPLATE to follow and how to use AI to fast-track the entire process…)
 
Would you be interested in this?
 
This is something several private clients and members of my Strategic Advisory Group Mastermind have been asking me to put together…
 
Right now, my working title is:
 
“Clear Mind, Steady Hand: How to Make Better Decisions in Turbulent Times.”
 

If this is something you would be interested in – shoot me an email with the word “STEADY” to let me know.

 
Right now, between my writing, advising one-on-one clients, and leading my mastermind – my schedule is pretty full.
 
BUT…
 
If there’s enough interest, I’ll consider putting together a session on this in the coming weeks.
 
Just my way of helping prepare for whatever comes next.
 
Because in this increasingly unpredictable world, there’s at least one thing I *do* know for certain:
 
The clearer your rulebook, the steadier your hand when the world starts shaking.

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