Stillwater Investing

Stillwater Investing Stillwater Investing is an independent advisory firm based out of Bangor, Maine.

Our job is to give you advice on saving money, building a portfolio, and reducing the risks that are often overlooked with investing.

What if your wealth got stronger when the world gets chaotic?That’s the real gift of antifragility. A powerful idea from...
05/14/2026

What if your wealth got stronger when the world gets chaotic?

That’s the real gift of antifragility. A powerful idea from a finance hero Nassim Nicholas Taleb.

It’s not just an investing concept. It changes lives.

Imagine an investor who loaded up on rental properties with high-interest loans during the easy-money years. Then tensions flare in Iran, oil spikes, inflation jumps, and the economy tanks. Tenants stop paying. Houses sit on the market for months. The only way to sell is a brutal fire sale.
The greedy get smashed! Some will be forced to liquidate at the worst possible time.

The antifragile become emperors. They had dry powder, conservative financing, and built-in cushions. They buy the distressed properties at deep discounts, lock in higher future yields, and come out far stronger.

Keys of the "Antifragile" Mindset
1. The Danger of the "Middle" (The Barbell Strategy)
The "middle" is where most people lose money. It’s the "moderate risk" mutual fund that drops 30% in a crash but only gains 7% in a bull market.
The Logic: By putting 90% in "boring" safety (cash, T-bills) and 10% in "aggressive" bets (startups, high-upside options), you cap your downside at 10% while leaving the ceiling wide open.

2. The "Absorbing Barrier" (Avoiding Ruin)
This is the most critical lesson. In mathematics, if you have a 99% chance of success but a 1% chance of "total ruin," and you play the game long enough, the probability of going bust is 100%.
Most people focus on the 99% gain; the antifragile focus exclusively on surviving that 1% "end of game" scenario. Build Antifragility. Design things so volatility makes you stronger (extra cash reserves, low leverage, small high-upside bets).

3. Demand Skin in the Game — Only trust people who lose when you lose. This is the ultimate BS detector.
If a financial advisor suggests a product but doesn’t have their own net worth in it, they aren't an advisor, they’re a salesperson. You want to follow people who "eat their own cooking."

4. Ignore most noise — Cut daily financial headlines. Focus on what never changes.
We live in an era of "information obesity." Most daily financial news is just "narrative fallacy"—people inventing reasons for why the market moved 0.5% today.
The Taleb Litmus Test: If you won't care about a piece of news in a year, don't give it 5 minutes today.

5. Avoid ruin at all costs — Never take a risk that can end the game.
Antifragility isn't about predicting the future. It’s about being the only one left standing when the "predictable" future fails.

Which of these resonates most with where you are right now — or what’s one way you’ve already made your life or portfolio more antifragile?

Comment below. I read every one.

*Investing always involves risk.

Back in a sharp currency squeeze a few years ago, some sophisticated accounts watched their American option hedges quiet...
05/13/2026

Back in a sharp currency squeeze a few years ago, some sophisticated accounts watched their American option hedges quietly drift in ways the models never flagged.

Why? Because the effective life of the option wasn’t fixed at maturity. Rate differentials shifted, and the early-exercise window — the point (or range of points) where it becomes optimal to exercise the option before expiration — started jumping around unpredictably. The forward hedge they thought was locked in… was not.

In plain terms: exercise time is stochastic — it moves with real-world variables like interest rates, carry, and volatility. Most risk systems ignore this and treat it as deterministic (fixed and predictable). That’s a dangerous assumption.

This mismatch creates convexity — the asymmetric extra payoff or protection that emerges when those hidden variables interact. Standard models systematically undervalue it because they assume smooth, stable inputs. In reality, those inputs are turbulent, and that turbulence can generate meaningful extra value… or hidden risk.

This is exactly why we built Stillwater’s process around real-world convexity and optionality instead of textbook assumptions. We account for those shifting exercise windows and second-order effects — the hidden currents beneath the surface — so portfolios don’t get caught flat-footed when financing and timing behave as they actually do.

For clients with $1M+, it means fewer nasty surprises and genuinely more resilient capital through uncertain markets.

If you want a clear-eyed review of how your hedges, options, or overall portfolio handle these kinds of realities, we are happy to walk through it with you.

*Investing always involves risk of loss.

Managing your own money sounds straightforward… until the painful lessons teach you otherwise.As a business owner you’ve...
04/14/2026

Managing your own money sounds straightforward… until the painful lessons teach you otherwise.

As a business owner you’ve proven you can build something of value. You pour your focus and capital into what you do best. But investing the wealth you’ve created is a different game entirely.

Markets test your discipline at the worst possible moments. Emotional decisions, overconcentration, or missing overlooked risks can quietly erode what took years to build.

I’ve spent 25+ years studying the markets—long before founding Stillwater Investing. After the Navy and UMaine, I learned one thing: Disciplined, simple ex*****on consistently outperforms complexity.

That’s why Stillwater exists. We take the heavy lifting off your shoulders with:
🔹 True Independence: No affiliations with banks or insurance companies. Our advice is 100% fiduciary.
🔹 Transparent Fees: A straightforward 1% AUM fee. No hidden charges, no layered costs.
🔹 Defensive Strategy: We focus on reducing the risks that others overlook so you can stay focused on your business.

If you have money to invest and want to avoid learning those "painful lessons" the hard way, let’s talk. We offer a complimentary portfolio review to give you a clear picture of your fees and risk—no obligation, no pressure.

🔗 Visit stillwaterinvesting.com or DM us to start the conversation.

- Hartt



*Investing always involves risk of loss.

11/08/2025

On True and False Friendship.

You have sent a letter to me through the hand of a “friend” of yours, as you call him. And in your very next sentence you warn me not to discuss with him all the matters that concern you, saying that even you yourself are not accustomed to do this; in other words, you have in the same letter affirmed and denied that he is your friend. Now if you used this word of ours in the popular sense, and called him “friend” in the same way in which we speak of all candidates for election as “honourable gentlemen,” and as we greet all men whom we meet casually, if their names slip us for the moment, with the salutation “my dear sir”—so be it. But if you consider any man a friend whom you do not trust as you trust yourself, you are mightily mistaken and you do not sufficiently understand what true friendship means. Indeed, I would have you discuss everything with a friend; but first of all discuss the man himself. When friendship is settled, you must trust; before friendship is formed, you must pass judgment. Those persons indeed put last first and confound their duties, who, violating the rules of Theophrastus, judge a man after they have made him their friend, instead of making him their friend after they have judged him. Ponder for a long time whether you shall admit a given person to your friendship; but when you have decided to admit him, welcome him with all your heart and soul. Speak as boldly with him as with yourself. As to yourself, although you should live in such a way that you trust your own self with nothing which you could not entrust even to your enemy, yet, since certain matters occur which convention keeps secret, you should share with a friend at least all your worries and reflections. Regard him as loyal, and you will make him loyal. Some, for example, fearing to be deceived, have taught men to deceive; by their suspicions they have given their friend the right to do wrong. Why need I keep back any words in the presence of my friend? Why should I not regard myself as alone when in his company? There is a class of men who communicate, to anyone whom they meet, matters which should be revealed to friends alone, and unload upon the chance listener whatever irks them. Others, again, fear to confide in their closest intimates; and if it were possible, they would not trust even themselves, burying their secrets deep in their hearts. But we should do neither. It is equally faulty to trust everyone and to trust no one. Yet the former fault is, I should say, the more ingenuous, the latter the more safe. In like manner you should rebuke these two kinds of men— both those who always lack repose, and those who are always in repose. For love of bustle is not industry—it is only the restlessness of a hunted mind. And true repose does not consist in condemning all motion as merely vexation; that kind of repose is slackness and inertia. Therefore, you should note the following saying, taken from my reading in Pomponius:“Some men shrink into dark corners, to such a degree that they see darkly by day.” No, men should combine these tendencies, and he who reposes should act and he who acts should take repose. Discuss the problem with Nature; she will tell you that she has created both day and night.

Farewell.
-Seneca the Younger

10/26/2025

Seneca’s warning on discursiveness reminds us that in thinking depth is superior to motion.

He warns that chasing too many books—or too many ideas—leads to confusion instead of wisdom. If you’re serious about growing in your field, don’t try to read everyone.

Find the few who truly think well, and study them deeply.

The Power of Investing EarlyJill starts investing at age 20. Jack starts at 30.Both invest $1,000/month. Both stop after...
09/23/2025

The Power of Investing Early

Jill starts investing at age 20. Jack starts at 30.

Both invest $1,000/month. Both stop after 45 years. Both earn an average 8% monthly return.

By age 75:
Jill’s account → $11.7M
Jack’s account → $5.2M
The difference? Time.

Each contributed the same $540,000. Jill’s account doubled in size simply because she started earlier.

Compounding changes lives.

👉 Want to see more examples of compounding in action? stillwaterinvesting.com/why_invest

👉 Want our help investing? Join the Stillwater client team here: https://www.stillwaterinvesting.com/get_started

*Investing always involves risk.

09/16/2025

The drone rises over Lyndon, Vermont.

Below us, rivers and forests remind us of scale and perspective. The words of Seneca reminds us of something even rarer: the value of our time.

We guard our money. We measure our possessions. Yet the most irreplaceable asset—time—slips away unnoticed. Seneca wrote to his friend Lucilius two thousand years ago, but his words cut through just as sharply today: “Nothing, Lucilius, is ours, except time.”

This video isn’t about investing in the markets. It’s about investing in the only thing that makes those markets matter—your life.

At Stillwater, we believe that clear thinking, calm perspective, and wise choices compound just like capital. Seneca shows us that wealth isn’t only measured in numbers, but in hours well-spent and days well-lived.

Soaring with Stillwater is an invitation:
To pause.
To reflect.
To place value where it belongs—on the moments you can never get back.

*Investing always involves risk.

The rare few. The one percent.They show up when it’s hard—when the waves are big, when others stay home.That’s the same ...
08/28/2025

The rare few. The one percent.
They show up when it’s hard—when the waves are big, when others stay home.

That’s the same mindset we serve at Stillwater: helping the elite build wealth, resilience, and a enduring legacy.

*Investing always involves risk.

🚨 Final Call! 🚨Today is the LAST DAY to register for the Penobscot Passage at the $50 early bird rate.Tomorrow, prices g...
08/15/2025

🚨 Final Call! 🚨

Today is the LAST DAY to register for the Penobscot Passage at the $50 early bird rate.

Tomorrow, prices go up.

Join us on the mighty Penobscot River for an unforgettable day on the water. 🛶

Whether you’re taking on the Long Course or cruising the Short Course, this is your chance to save money and secure your spot.

The Penobscot Passage: Honoring the Brave
📅 Race Day: August 23, 2025
📍 Launch from the Joshua Chamberlain Bridge, Bangor, Maine

💥 Register now before the price increases:
https://paddleguru.com/races/PenobscotPassage2025

08/12/2025

How do we give young men purpose—and get them productive again?

In this short from Episode 3 of the Yet to Be Named Podcast, Dale Hartt—founder of Stillwater Investing—and Jason Harkins—founder of LaunchPad (formerly Scratchpad Accelerator)—discuss how to motivate young men who feel directionless. Looking back to FDR’s citizen work programs during the Great Depression, they explore whether community initiatives or larger-scale efforts can provide the purpose and productivity that jobs once did.

Check out Dale and Jason’s companies:
→ Stillwater Investing: https://lnkd.in/eWBMPKhP
→ LaunchPad: https://lnkd.in/ediMmHC6

🎧 Watch the full episode → https://lnkd.in/eHRYRdp9

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