What’s your goal?
Before you invest a single dollar, ask yourself one very simple question: what am I actually trying to achieve? I know that sounds basic, but IMHO it is one of the most important questions in investing and one of the least asked. Most people jump straight to what stock to buy before they have even defined what they’re trying to achieve.
Are you investing to become wealthy? To preserve wealth? To generate income? To build something for your family, retire early, make a little extra money, or simply because markets are “fun” and intellectually interesting?
Those are completely different objectives, and different objectives should lead to completely different strategies. Someone trying to turn $100,000 into several million dollars should probably think very differently from someone with $10m whose main goal is making sure they never have to start over. One may need concentration, patience and a willingness to tolerate volatility, while the other may care much more about preservation, liquidity, taxes and avoiding catastrophic mistakes.
Neither person is right or wrong. They are simply playing different games, and one of the easiest ways to make bad decisions is to copy someone whose game has nothing to do with yours. Their portfolio may be perfectly rational for them and completely irrational for you.
Your objective should determine your strategy, and your strategy should determine what you own. What you own should determine what risks you are willing to accept, and those risks should make sense relative to the life you are trying to build. When that chain is broken, investing becomes much more random.
A lot of investors do the exact opposite. They buy something because it looks cheap, exciting, popular or because someone they respect owns it, then build the philosophy around the position afterward. The stock came first and the reasoning came second.
This is also why comparing returns without context can be so misleading. A 10% return may be fantastic for someone whose only goal is preserving a fortune while sleeping well, and completely inadequate for someone trying to multiply a small amount of capital many times over. The return by itself tells you very little unless you understand the objective behind it.
The same is true with concentration, diversification and cash. A concentrated portfolio can be intelligent or reckless, diversification can be intelligent or unnecessary, and holding lots of cash can be prudent or extremely expensive. There is no universally perfect portfolio because there is no universally identical investor.
One question I think matters even more is this: what is enough? If you never define enough, investing can become a game with no finish line. You can make millions, outperform for decades, and still feel behind because someone else always made more.
That is how people end up taking risks they never needed to take. They already won their game, but because they never defined what winning meant, they keep moving the goalposts. At some point the extra return may matter far less than protecting the freedom, time and security the money was supposed to create in the first place.
Money is not really the final objective anyway. It is a tool for buying optionality, independence, time, security and the ability to live life on your own terms. The portfolio should serve the life, not the other way around.
So before studying businesses, valuation, margins, balance sheets or the next great stock idea, study yourself first. Ask how much you need, how long you have, what you can afford to lose, what level of volatility you can genuinely live with and what outcome would actually make you satisfied.
These questions look simple, but they are fundamental to every important investment decision. The first investing decision is not what to buy. It is deciding what game you are playing and what winning that game actually means.
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The biggest flex isn’t a nice car, a big house or a huge portfolio.
It’s owning your time.
Tuesday at 11 AM and you want to golf? Go.
Your kid asks you to stop working and play? Done.
You want to take a month off? Take it.
Money is great.
But the whole point of building wealth is eventually not having to think about money.
Thoughts on Buybacks
One of the most underrated forms of compounding has almost nothing to do with explosive growth. It happens when a good business keeps buying back its own shares.
Imagine earnings grow just 5% a year. Nothing heroic and perhaps quote slowly. Now imagine the company also buys back 5% of its shares every year.
After 10 years, total earnings are only 63%. But earnings per share are 170% higher because those earnings are being divided among dramatically fewer owners. That’s a staggering difference.
That is the part I think investors underestimate. The business does not need to become 3 times larger for your economic interest to become almost 3 times more valuable.
Buybacks allow your ownership percentage to compound without you investing another dollar. You can go to sleep owning 1% of a company and, over time, wake up owning 2% simply because everyone else’s shares were repurchased by your business.
$NVR is a great example. The houses were only part of the story. For decades, $NVR kept shrinking the shares count while the underlying business continued producing cash.
And this is where buybacks become especially powerful. You do not need heroic revenue growth, heroic margins, or some giant new addressable market. You need a durable business, lots of free cash flow, a reasonable valuation, and a disciplined management that understands math.
Of course price matters enormously. Buying back stock cheaply increases the ownership of remaining shareholders at attractive prices, while buying it back at absurd valuations destroys value.
Growth gets most of the attention because it is easy to see and investors and the whole Wall Street fashion show are conditioned to jubilation over GROWTH. Buy prudently buying back shares intelligently is much quieter, and in many cases more effective for the sensible shareholder.
Sometimes the greatest compounding is not a business growing faster and faster. It is the same good business being divided among fewer and fewer owners.
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The Voting Machine Is Loud. The Weighing Machine Is Patient.
As I mentioned at the start of this year, this is likely one of the most bifurcated markets we have seen in over a decade.
Mr Market has been in a voting mood for the last year or two. For many high-quality businesses, the weighing machine has broken.
Those chasing the voting machine may look very smart for the next couple of years. Those chasing the weighing machine may look very foolish. Within four to five years, I believe that relationship has a high probability of inverting. The people following applause today may look foolish. The people following fundamentals may look obvious in hindsight.
One of the most difficult periods in investing is when what is supposed to make sense does not make sense — and does not make sense for a long time. A few months is easy. A year is doable. Several years is where most people break. They throw in the towel, usually at precisely the wrong time.
This is why I admire how Nick Sleep communicated with his investors. He often ended letters by thanking them for their patience and their understanding of the process.
He understood something many managers forget: the quality of the investors you attract can shape long-term results as much as the quality of the businesses you buy.
A large part of Nomad’s success was not only Amazon and Costco. It was the temperament of the people who owned the partnership with him.
That is why it is so important to keep a company’s fundamentals and destination as your North Star.
If the short-term stock price — the voting machine — is your compass, you will often feel like you are swimming with the tide, only to look up and realize you are far from shore.
When fundamentals are the North Star, you do not lose the route even when the current is against you. You are far more likely to reach the destination.
This is harder now than it used to be. We live in a hyperconnected world of constant short-term comparison. Delayed gratification has become unnatural. Same-day shipping, infinite feeds, and instant answers have trained the mind to expect the next hit tomorrow.
Investing does not work that way.
If you are watching prices every day, you are doing yourself a disservice as an owner.
There is a reason so many of the greatest investors spend far more time reading and researching than staring at tickers. Reading is not decoration. It is a way to drown out noise, suppress a biological craving for immediate feedback, and stay ready for the opportunities that actually matter.
The stock market will still be here if you do not look today, or this week. If the businesses you own are high quality and deeply entrenched, they will still be here too.
The lesson is simple and uncomfortable: process is not validated by the last twelve months of price action. It is validated by whether you still own what is worth owning when the crowd has moved on.
Patience is not a personality trait. It is a competitive advantage that most people cannot hold long enough to collect.
As Benjamin Graham put it: “In the short run the stock market is a voting machine, but in the long run it is a weighing machine.”
Airports have seen more genuine kisses than wedding halls ever have
Hospitals had more heartfelt prayers than churches ever will
Even graveyards have heard more "I Love You"s than bedrooms
Because if there's one thing humans are really good at... it's appreciating things especially when they're about to lose them
I mean, I didn't really appreciate family or what it meant until I moved halfway across the Earth and completely stopped seeing them
I never thought or valued my health until out of nowhere I had to spend a week in the hospital and lost it
You see, we ignore our health until it disappears and we take people for granted until they are no longer here
We waste years of our life wishing for the next chapter only to immediately spend the rest of our lives missing the ones that we finished rushing through
And that's what's so scary about life; is that one day you'll realize that today is the good old days
So stop waiting for your life to be perfect before giving yourself permission to appreciate its beauty
Hug your friends.
Call your parents.
Take the picture and enjoy the moments because you know it: life will teach you its value by taking them away.
I haven’t talked about this much…
About 5 years ago, I was miserable at my job.
I had a good amount invested in stocks and my 401k, but I knew I needed to go into overdrive if I wanted financial freedom.
So I made myself uncomfortable.
I invested more. I built multiple income streams. I forced myself to learn options.
Today, I make more through options and dividends than any salary could pay me, and I have full financial freedom.
The crazy part?
As I realized I didn’t NEED my job anymore, I hated it less and less. The stress disappeared because I was there by choice, not necessity.
And I probably never would have learned the skills that changed my life if I hadn’t been so uncomfortable in the first place.
Being uncomfortable is sometimes the best way to become comfortable.
@realroseceline Are you considering setting aside your investment portfolio as a private fund for management and subsequent transfer to the next generation? Thank you
@realroseceline@DD17_Capital That's a great point! I often remind myself that there's a big difference between information and hype. The true importance of this topic will only become clear over the years.
I asked to pitch me investing topics, business ideas, etc. There were a lot of fantastic suggestions, but @DD17_Capital stood out the most. I promised I’d pick my favorite and write about it, so here it is.
The Market Isn’t Your Biggest Opponent. The Algorithm Is.
Social media has given investors something previous generations never had: unlimited access to information. That’s an incredible advantage, but it also comes with an invisible cost. Every headline, every viral thread, every notification, and every prediction quietly influences how we think about businesses long before we ever buy a stock.
Most investors believe they’re making independent decisions. In reality, they’re making decisions inside an environment carefully designed by algorithms. The market hasn’t changed nearly as much as the way we experience it.
The fascinating part is that algorithms don’t optimize for truth. They optimize for attention. Fear spreads faster than facts, confidence spreads faster than uncertainty, and bold predictions spread much faster than thoughtful analysis because those emotions keep people scrolling.
Imagine two investors discussing the exact same company. One says it could compound at roughly 18% annually over the next decade if management executes well. The other says it’s the next 10 bagger and anyone who doesn’t buy it is an idiot. Guess which post reaches millions of people.
Over time, this quietly changes the way investors think. The companies appearing in your feed every day begin feeling like the best opportunities, not because you’ve studied them more carefully, but because your brain mistakes familiarity for quality. Psychologists call this the availability bias, but social media has turned it into a daily habit.
The same thing happens with FOMO. Most people believe they experience it because stocks go up. I think they experience it because thousands of strangers constantly remind them about opportunities they missed while almost nobody talks about the disasters they avoided.
Social media creates a completely distorted picture of reality. You see screenshots of 300% winners, predictions that a stock is going to the moon, and victory laps from people who happened to be right. You rarely see the years of waiting, the mistakes, the permanent losses, or the thousands of ideas that quietly failed.
The greatest damage isn’t convincing someone to buy one particular stock. The greatest damage is changing what investors consider normal. Once your brain becomes accustomed to stories about extraordinary returns, an exceptional business compounding at 20% annually suddenly feels boring.
Businesses haven’t become faster. Costco still opens stores one at a time. Visa still processes payments one swipe at a time. Wingstop still builds restaurants one location at a time. Reality still compounds slowly, but social media has trained investors to expect instant gratification from businesses that were never designed to provide it.
The irony is that the attention economy and the investment economy reward almost opposite behaviors. The attention economy rewards speed, confidence, emotion, certainty, and constant activity because that’s what generates engagement. The investment economy rewards patience, humility, probability, independent thinking, and long periods of doing absolutely nothing because that’s how wealth compounds.
Think about who benefits every time you open the app. The platform gets paid when you scroll. The influencer gets paid when you watch. The advertiser gets paid when you click. Your brokerage gets paid when you trade. Nearly everyone in the investing ecosystem benefits from your activity, while the investor usually benefits from patience.
This creates a fascinating conflict of incentives. The entire internet encourages you to do something every day. The market often rewards doing nothing for years. One system monetizes your attention, while the other rewards your discipline.
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The myth of luck
People love talking about luck. Someone builds a billion dollar company and they were “lucky.” Someone bought the right stock at the right time and they were “lucky.” Someone met the love of their life by chance and they were “lucky.” Looking backward, life often appears random. Looking closer and thinking deeply, it usually isn’t.
What we call luck is often the delayed byproduct of consistently putting yourself in good positions. It has far less to do with predicting exactly what will happen and far more to do with making decisions that slowly improve the odds in your favor. Most people don’t notice this because the compounding is invisible while it is happening. By the time the outcome finally arrives, the years of preparation have been forgotten.
One of the biggest mistakes people make is believing life is a game of certainty. They spend their time asking whether something will happen instead of asking whether they are positioned if it does happen. Great investors, entrepreneurs, athletes and leaders understand this difference. They know they cannot control the future, but they can absolutely control how prepared they are for it.
Every decision changes the probability distribution of your future. Reading one more book probably won’t change your life. Neither will one workout, one conversation, one dollar invested or one networking event. The power comes from stacking those decisions year after year until the probabilities begin to heavily favor you. Eventually people call the outcome luck because they never saw the thousands of small decisions that produced it.
This is why people constantly confuse the harvest with the seed. They celebrate the company after it becomes worth billions but ignore the decade spent learning, failing, reading, improving and taking intelligent risks. They admire the investor after the stock has increased tenfold but rarely appreciate the thousands of hours spent studying businesses before making the investment. The harvest is obvious, but seeds were buried underground where nobody was paying attention.
The fascinating thing about life is that good decisions do more than increase your odds. They create optionality. Every dollar you save gives you another opportunity you can say yes to. Every relationship you build opens another door. Every skill you develop creates possibilities that simply did not exist before. Wealth is not just money. Wealth is having choices when opportunity finally knocks. Luck is when opportunity meets preparation.
Looking backward, these moments seem almost inevitable. Looking forward, they are almost impossible to identify. Nobody knows which book will change the way they think forever, which conversation will lead to a business partnership or which investment will transform their financial future. The goal is not to predict the exact opportunity. The goal is to keep putting yourself in positions where opportunities are more likely to find you.
One of the reasons I love investing is because it constantly reinforces this lesson. You do not need to predict recessions, elections, interest rates or tomorrow’s headlines with perfect accuracy. You simply need to consistently buy wonderful businesses at sensible prices, avoid permanent mistakes and allow time to do most of the heavy lifting. Positioning is usually far more valuable than prediction.
The same principle applies almost everywhere else in life. Healthy people are rarely transformed by one workout. Great marriages are rarely built because of one romantic vacation. Exceptional careers are rarely created because of one brilliant meeting. Extraordinary lives are usually nothing more than ordinary decisions compounded for an extraordinarily long period of time.
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If you plan to be a long-term owner of a high-quality, cash-generative business with a wide moat, you should actually prefer a lower or stagnant stock price — at least in the short term.
This is because share buybacks become significantly more accretive when the stock trades at a lower valuation.
Here’s a simple example:
Assume a company has 10 shares outstanding trading at $10 each ($100 market cap), and you own 1 share (10% ownership). The company has $20 in cash available for buybacks.
👉🏽 If the stock trades at $10: The company can repurchase 2 shares, or 20% of the company. After the buyback, only 8 shares remain. Your 1 share now represents 12.5% of the company — a 25% increase in your ownership stake.
👉🏽 If the stock instead trades at $30: That same $20 can only repurchase about 0.67 shares, or roughly 6.7% of the company. Your ownership would rise to just 10.7% — far less accretive.
While a rising stock price delivers better short-term returns, for long-term owners the real benefit of buybacks comes from increasing your ownership percentage of the business’s future cash flows.
A lower stock price allows the company to retire more shares with the same amount of capital, meaningfully increasing your stake over time.
In short: For patient, long-term investors, a depressed stock price can be a gift when the company is actively buying back shares ����𝘩𝘪𝘭𝘦 𝘪𝘵𝘴 𝘮𝘰𝘢𝘵 𝘤𝘰𝘯𝘵𝘪𝘯𝘶𝘦𝘴 𝘵𝘰 𝘸𝘪𝘥𝘦𝘯.
Most people give up on dividend investing too early.
Not because the strategy doesn't work.
But because nobody told them what to expect at each stage.
There are 3 stages every dividend investor goes through.
Here's what they look like: