Weekly #33: The 100-Year Fund: How to Build Generational Wealth and Secure Your Legacy
We gained +3.3% this week (+5% YTD) and AGX soared 106% since December. Explore strategies like the Rothschilds’ and Hermès' for creating lasting family wealth.
Hello fellow Sharks,
This week’s edition is packed — lots of updates and insights. (If you want to skip ahead to the Portfolio Update, click here.)
But first, a quick note on TACO (Trump Always Chickens Out) — a term coined by Robert Armstrong at the Financial Times.
When I saw it, I had to smile. Back on April 28, I titled the Weekly “Trump Chickened Out…”.
So close to nailing the acronym! If only I'd spent five more minutes thinking it through, I might've beaten the FT to the punch. Next time, I’m bringing guac.
Now, back to the markets: the portfolio gained +3.3% in the first week of June, bringing us to +5.0% YTD — continuing to outpace the S&P 500. Momentum is building across key names, and some new data this week is worth paying close attention to.
Happy Sunday reading!
~ George
Table of Contents:
In Case You Missed It
Stride Inc. Stock Deep Dive: Why It’s Up 59%—And Still Has 57% Upside From Here
This week, I posted a deep dive on Stride. Since adding LRN 0.00%↑ to the portfolio, the stock is up 60%, but I still see another ~60% upside from here. Despite the market’s allergy to anything labelled “for-profit education,” Stride is quietly compounding value: expanding margins and riding long-term tailwinds in career-focused online learning. A misunderstood compounder that still hasn’t graduated to fair value.
Thought of the Week: The 100-Year Fund: Building a Legacy for Future Generations
When I was younger, I juggled engineering studies with three part-time jobs just to scrape by. I had big ideas and side projects in mind, but life dealt me a suited 7-6. Not the worst hand, it had about a 43% chance of winning if it improved.
I played the hand I was dealt (aided by a scholarship, luckily) and built a decent life — no regrets. Still, I can’t help wondering if I can deal a better hand for my kids and descendants.
What about a suited A-10? 63% chance of winning.
Or even better, imagine an A-A, that is an 85% chance.
If my descendants start with an ace-10 (or a pair), they’ll have more bandwidth to pursue their dreams instead of scrimping day-to-day. That got me thinking of a radical concept: what if I created a side trust fund like a 100-year investment fund for the family? A friend of mine, MJ, brought up the idea a couple of months ago and ever since, it has been floating in my head.
Along the way, I looked into history’s real long-lived fortunes. The Rothschilds are perhaps the most iconic example. In the 1800s, Mayer Amschel Rothschild built what would become the world’s largest private banking empire, with his five sons establishing powerful branches across major European cities. This decentralized yet family-coordinated structure allowed them to dominate global finance during the 19th century.
But by the 20th century, the family's wealth had declined significantly. No, they don’t secretly run the world from a mountain lair — despite what conspiracy theorists claim. The truth is more grounded (and frankly, more human).
One contributing factor was exactly what you'd expect in a multi-generational story: dilution. Mayer Amschel insisted that the fortune be kept within the family, even encouraging cousin marriages to maintain control. His son Nathan, who led the London branch, continued this strategy. However, over time, with more descendants involved and fewer of them actively managing the banks, the wealth inevitably started to fragment. The empire’s unified strategy frayed as new generations pursued different interests or lacked the financial acumen (or appetite) of their forebears.
Add to that external headwinds — two World Wars, the nationalization of banks, the rise of American financial power — and you’ve got a classic example of the old saying: "Shirtsleeves to shirtsleeves in three generations."1
If you're a history buff, The House of Rothschild (vol 1 and vol 2) by Niall Ferguson are hands-down the most comprehensive take on the family — but fair warning, it’s not a beach read. We're talking 1,100 pages of footnote-rich financial and geopolitical context.
The Rothschilds beat the odds for longer than most, but even they couldn’t defy this law of financial gravity forever. It’s a warning about how difficult it is to sustain wealth across multiple generations — and why thoughtful structures, values, and education matter if your goal is a true legacy. Both Chinese and Scottish cultures have sayings reflecting this idea:
Chinese: “Wealth does not last beyond three generations.”
Scottish: “The father buys, the son builds, the grandson sells, and his son begs.”
Not everyone fails, though. Some families have cracked the code to multigenerational wealth.
Take the Dumas family, the heirs behind Hermès. Now in its sixth generation, Hermès is still majority-owned by the family, and fiercely so. What’s remarkable is not just the brand’s luxury cachet, but how the family structured ownership: tight control, long-term thinking, and a refusal to cave to short-term market pressures.
In 2010, when LVMH attempted to take control, the Dumas family banded together, forming a holding company to block the attempt and successfully preserve their independence and legacy.
Then there’s the Mars family, of Mars Inc. fame (yes, the M&Ms, Snickers, and pet food empire). They’re notoriously private — and still 100% family-owned, despite being one of the largest private companies in the U.S.
The company isn’t publicly traded, so it doesn’t chase quarterly earnings hype.
Leadership stays within the family or among aligned professionals.
The Mars family promotes a culture of value creation over showy consumption. (You won’t find Mars heirs flaunting yachts on Instagram.)
The Mars family's story is fascinating and full of twists—I highly recommend listening to the Business Wars episodes covering Mars Inc.
What’s the common thread between these exceptions to the shirtsleeves proverb?
Tight ownership structure
Clear governance (often through trusts, boards, or family constitutions)
Cultural values that reward stewardship, not entitlement
Willingness to say no to short-term gains for long-term compounding
It’s not easy. It requires systems, values, and — frankly — luck. But the point is: it’s not impossible.
And maybe, just maybe, that’s what the 100-year fund is all about — giving future generations a fighting chance not to end up back in shirtsleeves.
The punchline is in compounding.
Einstein maybe said:
Compound interest is the eighth wonder of the world. He who understands it, earns it… he who doesn’t, pays it.
To illustrate, a one-time $10,000 investment at 10% annual growth becomes about $175,000 after 30 years, but nearly $137 million after 100 years!
Yes, you read that right.
This snowball effect is real—Warren Buffett likens compound interest to a snowball rolling downhill, growing larger as it picks up snow. Likewise, socking away just $200 a month over, say, 40 years, then letting it ride until year 100 would turn out to be many hundreds of millions (around $500 million). Imagine if your kids continued depositing $200 weekly after you're gone—the fund could easily surpass $1 billion.
The takeaway isn’t “hide all your cash until your great-great-grandkids come of age” — you’ve got to live and spend now too — but it shows that even modest savings, left alone, can grow into astonishing legacies over a century.
Raising Kids to Value Intangibles, Not Things
Another key piece: mindset.
We can't just hand our kids cash and expect positive outcomes. If our children grow up idolizing nice cars, big houses, and the biggest BBQ grill on the block, we’ve partly lost before we start.
Instead, let’s nurture values, relationships and purpose. Psychology and marketing research agree: once basic needs are met, spending on experiences and meaningful work brings greater satisfaction than material possessions. A study out of UT–Austin found people were consistently happier spending on experiences (travel, learning, family time) than on possessions.
In practical terms, that means emphasizing things like curiosity, kindness, creativity and hard work. Teach kids that money is just a tool — it shouldn’t drive them to stay in a job they hate or marry someone for a tax bracket. If they learn to value education, friends and giving back, then any money we pass on will be used wisely.
Millennials and Gen Z are, in fact, highly entrepreneurial. A recent survey found 66% of Millennials aspire to start their own business. I expect that as technology evolves, new generations will be even more entrepreneurial. Providing a safety net can only help that spirit. Just knowing a trust or fund exists can give young people the peace of mind to try something entrepreneurial that others without a safety net might avoid (like me in my 20s).
Locking in the Wealth: Trusts and Legal Structures
Okay, so we want to save and grow for 100+ years — how do we make sure no one (including us!) taps it prematurely?
In practice, this means using legal structures that lock up the money. One approach is a dynasty trust. This is a special kind of trust written to last many generations: beneficiaries get only limited access (say, for education or emergencies), while the trustee reinvests the rest. The goal is to keep the funds compounding rather than outright handing them out.
Now, I’ll admit—I haven’t gone super deep down the rabbit hole on this yet. Setting up a dynasty trust isn’t cheap (think ~$10K in legal fees), so part of me wonders if this is something we should only bother setting up 40 years from now, just before we head for the great bull market in the sky. But I’ll keep digging and let you know what I find. There may be a smarter, cheaper way to get 80% of the benefits without the full legal headache.
If you’ve found a better way to do this (or have strong opinions), let me know in the comments — I’d love to learn from you too.
Dynasty trusts can also shield the assets from estate taxes, creditors, or divorcing spouses — they literally “keep the funds safe” for the family’s future.
Side note: the old “rule against perpetuities” used to limit trusts to about 21 years after the last living beneficiary, but most places have reformed this. In fact, some U.S. states now allow trusts to run for centuries — Florida allows up to 360 years and Delaware/South Dakota allow trusts essentially in perpetuity.
The hard part is writing the rules. You might specify that the fund cannot be touched until certain conditions are met, or that descendants can only withdraw small, fixed amounts. We can even incentivize behaviour: for example, you could require grandchildren to stay employed, get degrees, or avoid debt before drawing from the trust. The trust could be drafted to pass your wisdom to the future generations. In other words, you’re not just locking away money — you’re embedding your family’s values and purpose into the rules.
We should also consider the possibility of adding to the fund over time. If your kids appreciate it, maybe they will contribute too. Even if all you do is stash a bit each year, it compounds powerfully. (And yes, we all still have to eat and enjoy life — nobody’s saying we become miserly monks. But automating a modest savings plan is the trick.)
Withdrawing Smartly: Nibbling, Not Gorging
Of course, I don't envision handing one lucky descendant the entire pot in 2125 and disappearing. The real goal is sustainability. I call it the '100-year fund,' but ideally, it evolves into a '1,000-year fund'—unless by then humans (or androids!) have transcended the concept of money altogether.
One idea: once the fund reaches a sizable threshold (say $100–200 million), start taking out a fixed fraction per year (e.g. 1–2%) and distributing that among all eligible descendants.
Maybe cap it per person (for example, $200k/year each) so that each branch of the family gets a fair share and the rest keeps growing. This way, every generation lives off the interest, but the principal keeps compounding. Each inheritor then has a real safety net — enough to quit a job they hate and pursue a passion, start a non-profit, or weather a crisis — without ever capturing the entire pot.
In practice, this is not far off from how college endowments or pension funds operate (they typically spend ~4–5% per year). It encourages responsible spending: go to med school, start that research lab, write that novel — but not to blow through the inheritance on a dream superyacht.
And yes, a little goes a long way.
For example, with a 1% withdrawal rate, a $100 million fund would generate $1 million per year. Split five ways, that’s $200,000 each — not an obscene amount, but more than enough to give someone the freedom to chase their ambitions. If there were 10 descendants, each would receive $100,000 annually. And if there were just one? They’d still get $200,000, while the remaining $800,000 would be reinvested back into the fund to keep the engine compounding.
To see the payoff: imagine if dozens or hundreds of families did this. We’d effectively seed hundreds of future startups, charities, and innovations. After all, even famous “self-made” titans had family help.
Take John Mackey, the founder of Whole Foods. He borrowed $45,000 from his dad to open his first natural foods store in 1978 — a move that eventually led to an $13.7 billion Amazon acquisition decades later.
If you’re into business stories and podcasts, I highly recommend checking out the Business Wars series on Whole Foods. This is actually the second time I’ve plugged Business Wars (no affiliate deal here, I just genuinely enjoy the show).
Or consider Reed Hastings, co-founder of Netflix. Before starting the company, he sold his first startup, which was funded in part by family connections and early support. That cushion gave him the freedom to swing bigger the second time around.
Even Warren Buffett had a running start: his father was a U.S. Congressman and stockbroker. Warren grew up immersed in financial discussions and bought his first stock at age 11.
The point is about having a true safety net. If your basic needs are covered by a steady annual income from a 100-year fund, you can afford to take bold swings. You can try, fail, and try again, without the risk of financial ruin.
Imagine if more people had that kind of runway. How much untapped innovation, art, science, and wealth might we unlock?
By creating this kind of long-term capital base, we’d be unlocking opportunities that wouldn’t exist otherwise. If our grandchildren can afford to experiment (and fail safely), who knows what Warren Buffetts or Emmas Watsons they might become?
In a way, a 100-year fund is a thought experiment: we’re not surrendering our lives to it, but structuring our legacy so that future generations have choices. We’ll still give, spend, and enjoy life — but with an eye to those who come after. If I wake up in 2125 (courtesy of science and AI keeping me youthful), maybe I’ll get to watch it in action. If not, at least I’m planting seeds now.
What legacy will you leave beyond your own lifetime?
Argan, Inc. earnings results — up 106% since inclusion
On December 23rd, 2024, I picked AGX 0.00%↑ as my top stock for 2025. I shared the thesis with my Patreon readers (before migrating to Substack) and shared updates.
Fast-forward eight months, and the shares are now up 106%.
So far, the thesis has played out almost exactly as expected: a multi-year upcycle in U.S. power infrastructure, driven by data centers, reshoring, and grid reliability demands, is feeding into a surge in large-scale natural gas and renewable energy projects.
In Q1 FY2026, Argan reported revenue of $193.7 million — up 23% y/y — with gross margins hitting a robust 19%, and diluted EPS of $1.60, up 88% from last year. Operating leverage is kicking in, with EBITDA margins expanding to 15.6%, thanks to strong execution and a favourable project mix at Gemma (its power plant EPC subsidiary).
The company also continues to sit on a pristine balance sheet: $546 million in cash and no debt.
Meanwhile, backlog surged to $1.86 billion (up 36% YTD), powered by full notice-to-proceed on the 1.2 GW Sandow Lakes gas project and continued momentum from Trumbull Energy Center and several renewable contracts. Management expressed confidence on the earnings call that total backlog will surpass $2 billion within the next six months — a milestone that, if hit, would mark a record high for the business.
Not everything was perfect: its Industrial Construction segment (Roberts) saw a revenue dip due to project timing, but management noted that its $91 million backlog should translate into “meaningfully higher” revenue in the coming quarters. The telecom segment (SMC) remains small but stable. One of the underappreciated elements of AGX’s story is how they’ve retained pricing discipline and margin consistency despite the project size increasing — there were no loss projects this quarter, which speaks volumes in EPC land.
Looking ahead, the outlook remains promising — but after a 100%+ rally, it’s time for a careful re-evaluation. Over the coming weeks, I’ll be updating my model to reassess the upside from here. There’s still room for this to run, but a move of this magnitude warrants a close look at whether AGX remains the best use of our capital going forward, or whether it’s time to rotate into a fresher opportunity.
Stay tuned.
Portfolio Update
The outperformance continues.
So far in June, the portfolio returned +3.3%, more than double the S&P 500’s gain.
Quarter to date, we're up +14.7%, blowing past the S&P 500’s +6.9%.
Year to date, the portfolio is now up +5.0%, compared to the S&P 500’s +2.0%.
And since launching the newsletter, our portfolio has delivered a +13.0% return, 3x the return of the S&P 500, which is up +4.3% over the same period.
We’re not chasing fads. We’re identifying mispriced opportunities, backing them with conviction, and letting compounding do the heavy lifting.
Let’s keep beating the tide.
Contribution by Sector
Tech, industrials, and gold were the main contributors to the portfolio this period — no surprises there given their strength in recent months.
Technology led the charge, driven by continued optimism in semiconductors and AI infrastructure names.
Industrials benefited from strong backlog growth and infrastructure tailwinds — names like AGX and POWL didn’t disappoint.
Gold chipped in the gain, as gold prices held firm near record highs amid persistent macro uncertainty.
On the flip side, education and consumer cyclicals were slight drags. Both sectors saw modest profit-taking after strong runs earlier in the year — nothing thesis-breaking, just some air being let out of the tires.
Contribution by Position
(For the full breakdown, see Weekly Stock Performance Tracker)
+55 bps AGX 0.00%↑
+35 bps CLS 0.00%↑ (TSX: CLS)
+30 bps TSM 0.00%↑
+29 bps IAG 0.00%↑ (TSX: IMG)
+27 bps POWL 0.00%↑
+8 bps MFC 0.00%↑ (TSX: MFC)
-1 bps DXPE 0.00%↑
-2 bps LRN 0.00%↑
-8 bps KINS 0.00%↑
That’s it for this week.
Stay calm. Stay focused. And remember to stay sharp, fellow Sharks!
Further Sunday reading to help your investment process:
How My BS Detector Made Me a Better Investor — and Less Fun at Parties
10 Timeless Investing Lessons from Warren Buffett (That Still Work Today)
Connecting the Dots in Stock Investing: Sharpening Your Mosaic Thinking
"Shirtsleeves to shirtsleeves in three generations" is a proverb that describes a common pattern in family wealth:
The first generation starts with nothing and works hard (in their shirtsleeves) to build wealth.
The second generation inherits that wealth and maintains it, often having been raised with an appreciation for the effort it took to build.
The third generation, having grown up in comfort, lacks the same discipline or work ethic — and often squanders the fortune, ending up back where the first generation started: in shirtsleeves.
Love the 100Y fund concept. Being pondering about it recently. Explore Liechtenstein for trust and foundation structures. They have quite strong propositions without the shortcomings typical of offshore jurisdictions.
PS: A great read about 100Y portfolio allocation is “The Allegory of the Hawk and Serpent” by Artemis.