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Welcome to the latest edition of the Healy Wealth Management newsletter, your monthly guide to navigating the financial complexities of life.
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On June 12, SpaceX went public in the largest initial public offering (IPO) in history. Within days its market cap soared past $2.5 trillion, matching Amazon’s, the fifth-largest company in the world.
Before you decide whether to buy, there’s a distinction almost everyone skips, and it’s the difference between making a smart decision and an expensive mistake. Ben Graham drew a hard line between investing and speculating decades ago, and most people calling themselves investors today are actually doing the latter without realizing it.
History is brutal here: railroads, automobiles, aviation, the dot-com boom. Revolutionary technology and a good investment aren’t the same thing, and Google proves why.
In the video link below, John Healy presents the one question you should ask yourself before you buy stock in SpaceX:
“I never truly break, I just change my form.
What was once a smooth ride now needs a step performed.
What am I?”
A number of our clients enjoy planning and funding “expensive” family vacations when the grandkids are out of school. If you’ve ever paused and wondered whether this was a responsible thing to do, you’re not alone. Most disciplined savers feel a flicker of guilt watching a big number leave the account, even for something this good.
Here’s the reassurance, grounded in both research and planning: for the clients with whom we’ve run the numbers, that flicker of guilt is usually not telling you something true about your finances. It’s an old habit talking, the one that got you to a healthy net worth in the first place by being careful.
But care and hesitation aren’t the same thing, and conflating them can quietly cost you years of irreplaceable time. Bill Perkins, in his book Die With Zero, has a phrase for what these trips actually buy: a “memory dividend.” Unlike a purchase that depreciates, a shared trip pays you back every time it’s recalled, told, and retold, for the rest of everyone’s life who was there. A week in Tuscany with three generations under one roof isn’t a expense that disappears the day you fly home. It shows up at Thanksgiving for the next twenty years.
The financial reality backs this up more than people expect. For most of our long-term clients, a properly funded plan has real room for this kind of spending without threatening retirement security, especially when it’s planned for rather than treated as an impulse. That’s the actual answer to “can we afford this?” – a number from your plan, not a feeling. If it’s been a while since we ran that scenario for you, it’s worth revisiting before you book the next one.
A few ideas, if you’re weighing where to take everyone next:
Multi-generational classics
Meeting in the middle, internationally
Built around a milestone
Lower-cost, still high-memory
The goal isn’t to spend recklessly. It’s to stop treating thoughtful, well-funded family time as a luxury you have to apologize for. If you’re sitting on a trip idea and wondering whether the numbers support it, that’s exactly the conversation to bring to us.
“I don’t think we’re as amazing as our parents are… I’m not going to have any struggles to tell my kids about. What’s my story going to be like?
‘Ah, son, once, when I was flying from New York to LA, my iPad died!'”
Aziz Ansari
On July 18, 2001, Warren Buffett stood in front of a packed auditorium at the University of Georgia’s Terry College of Business. The S&P 500 was sitting about 28% below the all-time high it had set on March 22, 2000. The dot-com bubble had burst, and the wreckage was still falling.
It’s worth remembering where Buffett stood in the eyes of the market at that moment. For years, he had been written off as a relic. Through the back half of the 1990s, while internet and technology stocks compounded at astonishing rates on the theory that traditional valuation no longer applied, Buffett kept talking about cash flows, discount rates, and businesses he could actually understand. To a lot of people, that made him look like he’d missed the new era of investing entirely, a has-been still playing checkers while everyone else had moved on to a different game.
Then the game ended. The new era investors who had dismissed him were nursing devastating losses in former darlings. Buffett wasn’t the only one vindicated. He was part of a minority of value investors who’d stuck to their principles while being told they were obsolete. But the math of what happened next is the real point. Buffett hadn’t beaten the bull market of the late 1990s; by his own admission he’d lagged it, sitting out gains other investors were posting. What he’d done instead was avoid the collapse that followed. A smaller gain compounded through the boom, paired with a far smaller loss through the bust, had put him ahead of most of the people who’d outrun him on the way up. Not losing was its own form of winning.
So when a student in that room asked him a deceptively simple question, “how do you find the intrinsic value of a company”, the answer carried a different weight than it might have in 1999. This wasn’t theory. It was the explanation for why he was right.
Buffett’s definition was direct: intrinsic value is “the number that if you were all-knowing about the future and could predict all the cash that a business would give you between now and judgement day, discounted at the proper discount rate – that number is the intrinsic value of a business”.
The Bond You Can’t Read
Buffett continued his answer by making a comparison most people overlook. “When you look at a United States government bond, it’s very easy to tell what you’re going to get back. It says it right on the bond.” The interest payments and the principal repayment are printed right on it. You don’t have to guess.
A stock certificate doesn’t come with that printout. The cash flows aren’t written on it anywhere. Buffett’s view is that this is precisely the analyst’s job: to take a stock certificate representing a piece of a business and effectively turn it into a bond, by estimating what the business is going to pay out over time.
That reframing is the whole exercise. Every investment, whether it’s a share of stock, a farm, an apartment building, or oil in the ground, comes down to the same question: you’re laying out cash now to get more cash back later, and the real questions are how much you’ll get, when you’ll get it, and how sure you can be.
Notice what’s missing from that question. It isn’t a question of how many analysts recommend the stock, what the trading volume looks like, or what the chart shows. It’s strictly a question of how much cash the business will generate. Price targets, momentum, and sentiment don’t enter into it at all.
One Business, Whole or in Pieces
Here’s a distinction that separates Buffett’s approach from how most people think about the stock market. Whether he’s buying an entire company or a small slice of one, Buffett says he always evaluates it as if he were buying the whole business. The question is the same either way: what will this business produce, and when will it produce it?
That mental model matters because it forces a different kind of discipline. You’re not asking “will this stock go up.” You’re asking “what is this business worth as an enterprise, and is the price I’m being asked to pay for my slice of it reasonable?”
The Honest Limitation
The part of Buffett’s answer that’s easy to skip past is the most important one, especially given the moment in time in which he was standing. He was direct about the fact that this framework simply doesn’t work for every business. It only works when you understand the economics of the business. If you can’t answer the question of what a business will generate and when, you can’t really buy the stock with any conviction. You can still gamble on it if you want to, but he won’t.
Buffett was candid that there are entire categories of companies, internet stocks among them, where he simply can’t answer that question and so he stays away.
That’s not a failure of analysis. It’s the discipline itself. Buffett isn’t claiming he can value everything. He’s claiming he only invests in what he can value, and he’s comfortable walking past everything else.
The Takeaway
Standing in front of that room in July 2001, Buffett wasn’t offering an abstract investing lesson. He was explaining, in plain terms, the discipline that had just kept him out of a bubble nearly everyone else mistook for a new paradigm. The lesson wasn’t that he predicted the crash. It’s that he never needed to. He simply refused to pay for businesses whose future cash flows he couldn’t reasonably estimate, no matter how loudly the market insisted that old rule no longer applied.
At Healy Wealth Management, we follow a disciplined value investment strategy. That means working to understand and estimate the value of every security our clients own in their portfolios. We would rather understand what we own and underperform a euphoric market than chase a story we can’t underwrite. After all, the businesses we can actually value are the ones that will generate the returns baked into our clients’ financial plans.
It’s worth noting that the parallels to today aren’t subtle. The current enthusiasm around artificial intelligence has many of the same hallmarks as the dot-com era Buffett was speaking into in 2001: a transformative technology, genuine and real, wrapped in valuations that assume flawless execution and unsustainable growth, with little patience for the question of what cash these businesses will actually generate and when.
We don’t know how the AI story ends any more than anyone did with the internet in 1999. What we do know is that the discipline of sticking to businesses we can value, rather than ones we can only hope to value, is the same discipline that served patient investors well the last time a “new era” insisted the old rules didn’t apply.
“The line separating investment and speculation, which is never bright and clear, becomes blurred still further when most market participants have recently enjoyed triumphs. Nothing sedates rationality like large doses of effortless money.”
– Warren Buffett,
Berkshire Hathaway Annual Letter to Shareholders,
February 28, 2001
Answer:
An escalator.