What Drives Stock Prices?
A Look Into the Underlying Forces That Determine How Much Money Investors Make From Their Stocks
Recent years have seen a surge of speculation that, by some measures, looks similar to the dot-com era. Generally speaking, most investors have made a lot of money, but a few folks have generated absurd returns on what is essentially a non-sustainable momentum trade that, when it turns – and I believe it will – is not likely to end well. (I remain steadfastly convinced that most of the advantages of large language models are going to go to integrations of existing software platforms and that the frontier models essentially are more similar to airlines in cost structure than the old-line software companies. Most folks are not running cutting-edge medical research or the like. Instead, locally run private models are the future because the forces of capitalism cause the cost advantages to become extreme. Boardrooms will eventually wake up to this fact and I think the landscape looks very different two years from now. We’ll see.)
In any event, to alleviate my own concern for my fellow man, similar to what I did in the dot-com era and the run-up to the real estate hype prior to the Great Recession, I feel it is important to remind everyone that, at the end of the day, the mechanics that drive wealth accumulation through ownership of stock can be broken down into constituent parts. If you expressly identify those parts, it’s much easier to confront your assumptions and test them for reasonableness; to separate speculation from investment.
Let’s begin.
The Two Sources of Potential Profit When You Invest in Stocks
There are two sources of potential profit when you make an investment in stocks. They are:
- Changes in the stock price. You hope to buy at a low price and sell at a higher price.
- The cash dividends you receive during the time you are an owner.
Looking at this from an engineering standpoint, we can break down those components into their simpler forms. What causes those two things? We can build a cause-and-effect tree to boil down the core actions that result in a stock becoming more valuable or less valuable.
We Can Break Both Into Their Underlying Components to Better Identify the Levers
- Change in the Stock Price – This can be driven over time by:
- The Absolute Amount of Diluted Earnings per Share, Which Can Be Approximated As*:
- Book Value per Share x Return on Equity
- Return on Equity can be broken down either into three components, multiplied together, which are …
- Net Profit Margin (Net Income ÷ Revenue)
- Profit Margin is Profit ÷ Revenue.
- Profit is Revenue – Expense.
- There is one way to increase Profit, which is to increase Revenue relative to Expenses in absolute dollar terms so the spread between the two increases.
- Asset Turnover (Revenue ÷ Average Assets for Period)
- Leverage, or Equity Multiplier (Average Assets ÷ Average Shareholders’ Equity)
- Net Profit Margin (Net Income ÷ Revenue)
- … or, alternatively, more granularly refined into five components, multiplied together, which are …
- Tax Burden (Net Income ÷ Pre-Tax Income)
- Interest Burden (Pre-Tax Income ÷ Earnings Before Interest and Taxes)
- Operating Profit Margin (Earnings Before Interest and Taxes ÷ Revenue)
- Asset Turnover (Revenue ÷ Average Assets for Period)
- Leverage, or Equity Multiplier (Average Assets ÷ Average Shareholders’ Equity)
- Book value per share comes from issuance and repurchase of stock, retained earnings, and a handful of other transactions or adjustments, including adjustments for LIFO reserves.
- Return on Equity can be broken down either into three components, multiplied together, which are …
- Book Value per Share x Return on Equity
- The Valuation Multiple Other Investors Are Willing to Pay for Every $1 in Diluted Earnings Per Share
- This is the result of buyers and sellers bidding with each other on the stock exchange or over-the-counter market, sort of like eBay. In the long run, it is influenced heavily by the yield on the risk-free rate, which is considered to be the United States Treasury bill, note, or bond with the closest maturity to the cash flows being measured. Holding all else equal, if the risk-free rate increases, stock prices should be lower to compensate so earnings yields increase (diluted earnings per share divided by the per share price indicating the “coupon” rate one would receive before any dividend taxes assuming no growth and a 100% distribution policy). Likewise, if the risk-free rate decreases, stock prices should rise so that earnings yields decrease. Generally, for a stable blue chip stock with reasonable growth prospects, it can be prudent to demand a normalized earnings yield of at least 2x the risk-free rate, adjusting for cyclical influences on per share profits (acknowledging the strange experience with interest rates in recent decades post-Great Recession has muddied the waters).
- The Absolute Amount of Diluted Earnings per Share, Which Can Be Approximated As*:
- The Cash Dividends You Receive
- Ultimately cash dividends must come from one of a few sources:
- Profit generated from operations, which is the only sustainable source
- Asset liquidations, such as if a company sold a division, subsidiary, or other asset and distributed the proceeds. At some point, you run out of assets so this can be a nice source of cash but is limited by its very nature.
- Changes in the capitalization structure. Some companies borrow money when fixed-rate terms are available and interest rates are low, then distribute the borrowed funds, in whole or part, to stockholders as a dividend. The net effect is a cash dividend, which results in a change in the capitalization structure with a greater proportion of the enterprise value being made up of debt, rather than equity.
- Ultimately cash dividends must come from one of a few sources:
Spin-offs are just the breakup of an existing asset. You are no richer the moment after the spin-off than you were before. Thus, they aren’t a true source of income. One reason certain spin-offs tend to do better than stocks as a whole, at least after a few years, is because a dedicated management team is able to focus on a more streamlined business and must economically live and die by its results. In other words, the stakes are lower for Gillette when it’s part of Procter & Gamble than they are when it is a stand-alone publicly traded company with its own stockholders and dividend.
Where it gets tricky is that the figure you are actually using for valuation is not truly diluted EPS. Rather, it should be something called “owner earnings”, which is the amount of money a business owner could extract for redeployment or consumption without changing unit volume or harming the competitiveness of the enterprise. As I’ve shared on the site many, many years in the past, I make a few modifications for my own personality and the sake of conservatism, but the basic formula is this (see the Additional Notes section for further information):
Reported Net Income
+ Depreciation and Amortization
+/- LIFO Inventory Reserve Adjustments
+/- Accounting Adjustments That Obfuscate Reality
– Additional Working Capital Required to Maintain Current Unit Output and Competitive Position
– Maintenance Capital Expenditures Required to Maintain Current Unit Output and Competitive Position
+/- Adjustment Factor for Overfunded or Underfunded Pension
+/- Adjustment Factor for Other Non-Avoidable Contingent Cash Inflows or Outflows
= Stable Cash Extraction Value for an Owner Opting for a 100% Dividend Policy of Any Earnings Not Required to Maintain Current Competitive Position in the Industry
Then I compare that value, if I could own the entire enterprise, lock, stock, and barrel, to the net capital required to be invested in the business, both equity and total, as a mechanism for determining the quality of the firm’s existing operations, factoring in things like durable consumer brands that would be almost impossible to displace or physical advantages that competitors can’t replicate (e.g., possession of a key oil field, a cement company being mostly local, etc.), or a hidden asset that makes the numbers somewhat inconsequential (e.g., if you were buying a farm on top of a natural gas well that no one knew existed, it would be somewhat foolish to value solely the cash flows from the corn and wheat, without expressly contemplating what you might get from the energy asset that you can monetize) which is the art part of it. I also discount all streams of owner earnings at the same rate rather than attempting to apply varying discount rates to compensate for perceived risk as the former methodology is a pass-fail test. That is, if I am not comfortable enough to feel certain of the owner earnings range, I should confront that fact directly rather than attempt to convince myself it can be mitigated by tweaking the formula.
Knowing Individual Businesses Helps in the Calculation of Owner Earnings
Over years and decades, as you study specific enterprises, it becomes much easier to spot changes not only in their operations, but across industries. For example, an investor who owned a blue chip cash machine like Clorox should know that it is almost entirely a domestic business compared to other large consumer staples (something like 84% of sales are within the United States) and management targets free cash flow in the 11% to 13% of revenue range. Meanwhile, marketing and advertising expense has long run in the 9% to 11% of revenue range broadly and approximately speaking. If the former were to start skyrocketing, but the latter were cut down by a few percentage points, it would be a major red flag that a short-sighted executive team was mortgaging the future to juice profits today. The bill would come due at some point and the headline cash flow numbers wouldn’t be a true indication of sustainable profitability. (This is not happening at the moment with Clorox, I simply used it since nearly everyone in the United States is familiar with one or more of their products.)
Portfolio Construction Is a Different Discipline Constructed from the Building Blocks of Individual Assets
Portfolio construction is itself an entirely different discipline. I’ve said forever that people always ask me about valuation of individual enterprises, when half of my career and time is spent thinking about how those pieces fit together in a given portfolio. Hardly anyone asks about the latter, yet it matters enormously. I think about weightings a great deal. All the time. I’m looking through to the underlying cash flows and viewing the portfolio as one holding company then asking myself what I think it looks like in 5 years, 10 years, or 20+ years. (Sometimes these weightings are influenced by how a company is returning cash. Maybe one day I’ll write about the mechanics of one of the largest trades I ever placed for Kennon-Green & Co. and how it would have differed if the underlying enterprises weren’t paying such large dividends.) The ideal portfolio differs for different people at different times in life, too.
As importantly, knowing the nature of each business, which we discussed a moment ago, helps in constructing a portfolio. Being aware of the forces that drive changes in revenue, or cost structure, can help you manage correlated risk across a collection of businesses. The example I used to give was to think of an oil town in Texas in the 1980s. You might have shares in the local bank, own the local pizza parlor, have some apartment buildings, and collect dividends from shares in the oil major, but if an energy bust happens, a good portion of the ultimate cash flows in that town, which appeared to come from diversified sources, suddenly dries up at once because the thing funding it was wages from the petroleum industry. It was a mirage.
People generally fall into two different categories: top-down investors, who decide on broad areas of the economy first and then narrow their choices, or bottom-up investors, who are looking out across the world for anything intelligent to do within their circles of competence, valuing those assets, and then having their portfolios come to reflect individual opportunities over time. Most value investors, myself included, tend to prefer the latter.
Additional Notes
This is a general academic overview meant to give you the big picture with enough granular detail to understand what is happening under the hood, so to speak. In actual real-world practice, the accounting board has lost its mind since the mid-2010s in ways that require further adjustments to the intrinsic value formula. For example, when I mention diluted EPS or net income, if a company has equity investments on the books that have readily determinable fair values (other than those reported under the equity method or consolidated method), changes in fair value are now run through the income statement. It is absolute nonsense. The old adjustment to the balance sheet for nearly all enterprises was a vastly superior methodology. The change was not modernization, but rather a result of people simply trying to do something to justify their position. It destroyed the utility of reported figures for companies such as Berkshire Hathaway and created heavy incentives to either ignore GAAP (a dangerous precedent) or for managements to pass on otherwise intelligent capital allocation opportunities because of how it may cause their reported numbers to fluctuate, weakening the business over time. In any event, as a result, when calculating intrinsic value, I find it necessary to adjust the above formula further to strip out the contribution from unrealized gains or losses arising from market fluctuations as they tell you nothing of the quality of the underlying cash flows for the actual entity you are purchasing in nearly every case.
Footnotes
* I say “approximated as” because it’s not precisely on point to state diluted EPS is the result of ordinary book value per share × ROE unless earnings, equity, and share-count measures are defined consistently. This arises as a result of timing differences and/or differences between basic and diluted share counts used across calculations. ROE ordinarily uses average equity for the measurement period, while reported diluted EPS uses weighted-average diluted shares. Book value is an end-period measurement figure. This technicality can mean a great deal in situations where, say, a company is buying back a huge percentage of the outstanding shares.
Reader Comments (4)
Comments are presented chronologically, with replies indented beneath the comments to which they respond.


BidAskDividends
September 6, 2026
Although likely considered basic and foundational for seasoned investors, it is mandatory reading; full stop.
clobber
September 21, 2026
"I’ve said forever that people always ask me about valuation of individual enterprises, when half of my career and time is spent thinking about how those pieces fit together in a given portfolio. Hardly anyone asks about the latter, yet it matters enormously. I think about weightings a great deal."
I guess I keep asking the wrong people because hardly anyone will give me a full/thorough answer. Either they don't know, or this is the secret sauce that they are unwilling to part with. How exactly should someone determine appropriate portfolio parameters and then implement investments to match the parameters? To get a bit more technical, how would someone determine their risk tolerance and capacity (Are these "feelings?" Are they numbers? Can they be calculated?). Related to that, how can they determine maximum tolerable drawdown, tolerable standard deviation, etc. What is the full set of parameters that should be considered? Once those parameters are determined, how to you select a portfolio that aligns? I do understand the basics of modern portfolio theory and the efficient frontier, but how do you actually implement that - or whatever framework you use - in practice?
Thanks!
Joshua Kennon
September 24, 2026
Replying to clobber
So, keeping this academic and high-level educational (like all things on my personal blog, none of this is investment advice), it might help to think of it like this ... and please forgive any typos or de minimis errors because I am trying to bang this out over a cup of coffee while Aaron takes the kids to school before we head to the office. I'm typing it in real-time and won't re-read it before I submit it. Think of it like us having a conversation; spoken word.
First, you have to take a step back. Foundational. Every pool of capital, or portfolio, has a job to do. Many successful families have multiple portfolios. You start by clearly defining the goal of that portfolio.
To provide a few illustrations:
At the investment firm I own, we have several different types of clients.
One group consists of highly successful individuals, some of whom even work in finance, and aggressively compound their money. They shift a portion of their capital to a portfolio under our management, typically in the seven or eight figures, and have us manage it on a Global Value basis. This is inherently more conservative than their main activity, or portfolio, that they manage which can consist of taking over entire businesses, acquiring or developing real estate, launching technology startups, or working on Wall Street. The capital we handle for them is designed as a sort of "permanent capital" with the view that if it fails, civilization has fallen for all intents and purposes. Some dump in a large lump sum and plan on letting it ride for decades, others regularly add five or six figures with the goal of expanding it over time and re-arming us with dry powder for opportunities, but the point is, if God forbid they died, the complex, riskier operations they oversaw gets sold by their estate and the bulk of the rest of the money ends up at the Firm alongside their existing holdings, allowing the surviving spouse or children to maintain a high standard of living.
Others have unique twists in the mandate, such as tech executives earning millions of dollars a year who request we build a portfolio using the same philosophy but avoid all technology companies regardless of what that may do to performance because the job of the pool of capital is to provide a ballast of sorts for human capital + equity rewards that are entirely concentrated in a single industry that, at some point, will likely experience another horrific winter like the 2000-2003 period.
Still others are retired, or experienced a liquidity event, and want to live off their money as a source of private income now.
An insurance company might have a book of annuities that it needs to fund, which involves an asset / liability matching component.
A deeply religious investor might want to earn money but not worry about holding certain types of companies.
A pension fund manager for a small business may need to think about trying to control returns within a statistical band (as strange as it seems, for something like a Cash Balance Plan or similar, if it isn't designed in a specific way, having performance that is too high can cause some horrendous problems so you want to target a 5% to 7% range long-term return; way beyond the scope of this discussion but it gets into end date ultimate benefits versus the potential for confiscatory excise taxes).
All different jobs.
So, again, before you look at construction, and the weightings that arise from that, you first have to be clear about the job. Most small investors without a lot of capital think the goal is to compound money at the highest rate possible, timing, taxes, cash flow, and risk be damned. Once you have any real money, that is not at all how your life operates; college funds that need to be there at a specific time even if we are going through a 2009; purposely taking losses on positions you otherwise want to hold to maximize the tax-vs-time-value-of-money calculation with the intention or hope of repurchasing in the future (esp. for high earnings in states like New York, New Jersey, or California); strategic liquidity reserves that should be available within six to twelve months at all times to support a portfolio of privately controlled businesses, etc.
Once you identify the job, you then start to work backwards through a series of checklists. First, is there an asset/liability matching component. That is probably the most important thing to settle from the beginning. For example, if someone shows up at the Firm with, say, a $2,000,000 portfolio and wants to retire in the near future, taking a distribution of, say, $6,000 per month, that money has to be non-negotiable to extent possible in the capital markets even if we hit a 1929-1933 tomorrow, which was the worst economic event in 600 years. That is a clearly-defined asset/liability matching problem. To survive a collapse like that, you need anywhere from 36 to 60 months of reserves held in the highest quality asset possible consistent with doing that job, which for U.S. investors certainly is a U.S. Treasury backed by the taxing and military power of the United States, compelled to be paid by the U.S. Constitution, and exempt from state (but not Federal) taxation. We treat the $500,000 or $2,000,000 client the same way a family office would treat a $70,000,000 client (because that is precisely how I expect my own capital to be treated and my name is on the building) in that I will literally build out something like a 60-rung or greater maturity ladder of U.S. Treasurys the client owns themselves, in a segregated portfolio. It's far more powerful than, say, a 5-year ETF where the maturity is constantly rolling because you have specific contractual cash flows guaranteed by the government on specific days with clearly defined coupons, yields-to-maturity, and risks. So in the case of our hypothetical $2,000,000 investor, you're, by definition, talking about $6,000 x 36 = $216,000 (10.8% of capital) or, much more likely at the start, $6,000 x 60 = $360,000 (18.0% of capital) for what I call the "firewall" component. I use firewall because if the world is burning down, this is the thing that has given the client time. If stocks are down 90%, unemployment is 25%, there is another Dust Bowl, etc. those distributions should continue as long as the United States Government has not fallen. (If it has, so too has the global economy given its size and the interconnected nature; no one of note or scale escaped.) Importantly, those Treasurys are the same type of asset that companies like Berkshire Hathaway hold when you hear about their legendary "cash" reserves. It's largely not cash, it's directly identifiable Treasury securities.
The point is, that by defining the withdrawal rate (e.g., $6,000 per month), and applying a 60-month reserve based on the 1929-1933 experience (which would likely last longer because the typical person is going to severely reduce their spending in the event of such an economic cataclysm) has set the first group component weighting (firewall at 18.0% of $2,000,000 capital, each rung at $6,000), but if the withdrawal rate were the same and the portfolio had started at $5,000,000, the same "job" took only 7.20% of capital. You start with the job. You achieve the job. It definitionally absorbs some of the capital.
(Now, in actual practice, I may build in inflation increases for some clients under some conditions, and I will also accept "brokered" FDIC-backed certificates of deposit provided the client's aggregate exposure to any one institution is below the insured limits because many will have special features such as a spousal "Survivor's Put" so that if one spouse dies, we have the option to demand full par back as an emergency, which could be powerful under a set of horrible circumstances you hope never happens. Again, I'm simplifying this to high level principles.)
Beyond that, if the person is living off the capital presently, and they hold no other outside investments, I'd typically want the sum of [cash + the firewall + general fixed income] be no less than 25%, and no more than 75%, of the portfolio in question (and remember many successful families run multiple portfolios, some at a single institution, often at many institutions) given my objective is to have them survive both a 1929-1933 scenario and a 1970s-style inflation run. There are no guarantees, of course, but mathematically / probabilistically, it's what lets me sleep at night. This allows you to adjust for valuation levels; e.g., if it's the late 1990s and Coca-Cola is trading at 50x earnings while U.S. Treasurys are yielding 6%, you obviously don't want a lot of stock, whereas if it is 2009 and everything is on sale, especially as a value investor, you probably want to be buying businesses left and right. Again, we definitionally know that the withdrawal rate is what set the absolute weighting of the firewall component, so you look at age, life expectancy, other plans (you may have sub-portfolios within this set of components to fund specific things like construction of a vacation house, etc.) The general fixed-income component can consist of anything subject to ordinary risk, valuation, etc. There has been a brief moment in recent weeks where, using an asset placement strategy, I've been able to build up fixed-income components in tax-sheltered retirement accounts locking in roughly 5.5% to 6% yields-to-maturity and yields-to-call holding investment grade positions in solid underlying companies. Other times, I've bought plain-vanilla mortgage backed securities with great underlying characteristics so you see the principal and interest come in each month. Some involve tax-advantaged municipal bonds. It's a combination of what is attractive, where the risks in the economy are, what the yield curve looks like; etc. Individually, I think a lot about overall weighted duration, sector/industry exposure; you get the idea.
After you've solved these issues, you're left with equity weight (or if there were no fixed-income component, you start here in the case of a 100% equity allocation). Importantly, you think about not just absolute weight of a specific component, but relative to other components. For example, a great investment, weighted at 5%-at-cost or, in some cases, 6.5%-at-cost, can really move the needle over a decade or two. Importantly, if you have another non-correlated holding weighted at the same thing, it can overcome a lot of disaster through what I used to call "The Home Depot effect" ... e.g. if you buy one at 5% and it returns a 500% profit, it mathematically swamps a second component that goes down 50% and is sold at a loss. Consider a $1,000,000 equity allocation with $50,000-at-cost put in Holding 1 and $50,000-at-cost put in Holding 2. If, seven or ten years later, Holding 1 is $250,000, it doesn't matter much if Holding 2 is at $25,000. In an ideal world you want to pattern-match, for lack of a better term, so that Holding 1 and Holding 2 are not the same. Ideally, you want to do this on an industry or sector basis, too, but what really counts are individual holdings at specific prices. For example, I'm not going to wake up and say, "I need to put [x%] into utilities or banks", I wake up and say, "Let me study everything going on in the world and see what is interesting on a risk-adjusted basis where I think the probabilities over the next decade or two are strongly in our favor even if things go down 50% the day after I buy them."
Sometimes the nature of how the cash flows are delivered can change things dramatically. For example, I responded to another comment last night using a real-world example of something that happened early on in the decade. I won't repeat the entire thing here ( it is on the Lessons from Ray Kroc's Paper Cup Years post ), but the portion relevant to this conversation read:
"Sometimes the nature of how the cash flows are delivered can change things dramatically. For example, I responded to another comment last night using a real-world example of something that happened early on in the decade.
A perfect historical example, which I'm fine sharing since the headline numbers are part of public filings and it is further in the past: Back in 2017 or 2018 if someone would come on board with a stake in Altria Group or similar, the shares were not nearly as attractive priced as other opportunities we saw. I distinctly remember selling some to what I imagine was shock. A few years later, Covid hits, interest rates basically go back down to a near zero-rate environment, and regulators had somehow allowed four or five tobacco companies (which were transforming into nicotine companies; an important distinction) to consolidate so that by purchasing them, in specific weightings and as a group, you could essentially get a significant majority override on all nicotine consumed on planet Earth each year outside of China. (The Chinese government basically has a monopoly on the industry within its borders so it isn't useful to include it in any analysis.)
Suddenly, you had this basket of companies - four if you focused only on Altria Group, Philip Morris International, British American Tobacco, and Imperial Brands, five if you included Japan Tobacco in Tokyo, though it was really a conglomerate with a packaged food division - offering enormous yields at a time when money was basically non-productive if parked. I'd have to check the specifics but over that period, I think we deployed something like $22.5 or $25 million or thereabouts buying up what I called a "structural tobacco trade" at weighted average dividends yields which I believe were in the 7% to 9% on the basket itself. I did a series of calculations that even if the dividend growth rate collapsed to far below its historical average, each year we took so much money off the table, it dramatically reduced our risk and funded other positions. By year 10, the probability of getting the near totality of our outlay back was enormous by my estimations. Assuming even exceedingly conservative dividend yields at the end of that period would indicate market prices about twice as high as the then-market values. Very little needed to go right for it to be satisfactory. It was a totally different risk calculation. I mean, imagine if in year five someone invented a drug that cured nicotine addiction and the stocks all went to zero. We'd have still taken so much cash off the table, combined with the tax deduction from the loss, the damage would have been modest in the big picture of things.
That one big decision has been an important one, serving as a major source of internal funding especially because the cash dividends were hiked in the aggregate quite notably from those already absurd base values (I mean, Philip Morris just raised its dividend another 8.8% over last year, which is on top of the 8.9% rise we got the year before that. Altria just raised it's dividend by 4.7% ... it's nuts). You look at the holdings in Meta or Alphabet we picked up when investors thought they were doomed to oblivion a few years ago, it's accurate to say for a lot of folks, the tobacco holdings helped cover the cost. I had no interest in buying Meta but then it basically got down to a price so low that I figured it had to be in the single-digit p/e on cost in the not-too-distant future.
The big question around the tobacco operation was the ethics, but it came down to the fact that essentially every investor owns it in one form or another through ETFs and funds, plus, holding all else equal, every bit of scientific evidence I could find indicated that the harm reduction of vaping and smokeless heated tobacco over traditional combustible cigarettes was dramatic. Furthermore, prohibition doesn't work, rather leading to a rise in funding organized crime and tax evasion, so it's better for the industry to be heavily regulated by authorities. There is also the question of proximity. Shareholders of Berkshire Hathaway presumably make an awful lot of money from McLane, which provides cigarettes to a massive amount of gas stations and convenience stores, it simply doesn't get noticed because it is reported with a gargantuan pool of earnings from other subsidiaries including insurance, regulated utilities, and homebuilders. Regardless, at the end of the day, I approved any opt-outs for those who were not comfortable holding the position. I get it ... the idea of holding a stake in a for-profit prison is anathema to me because I can't get to the difference between it and a form of slavery, though if I ever found one that was inexpensive I feel it is my obligation as a fiduciary to notify clients so they can take advantage of it if they wanted to do so.
That's not to say every apparently obvious situation works out. There have been a handful of disappointments, but the thing about compounding is the math works out wonderfully if you think about portfolio structure."
In some cases, especially for wealthy folks in their 20s-50s with all equity portfolios and who were regularly contributing new deposits, I built out the group operation at about 1/3rd of the equity capital split among those components; one structural trade representing a third of money with some individual components going to I believe it was 8.5% but I'd have to check. The point is, I never would have done that if the companies had a 100% retention policy rather than sending most of the cash out the door in the form of dividends. Buying at such high yields-on-cost when the payouts weren't in question - these businesses were not distressed by any stretch of the imagination - the relative risk dropped with each passing quarter as we were drowned in cash flow. Like clockwork, another 90-some days pass and a wave of deposits hit across the accounts, fueling acquisitions in other non-tobacco holdings. The stocks went nowhere for something like 3 years - investors simply did not want them - until suddenly they did. It didn't matter. We were holding them to extract the cash, like an oil well that you know might eventually run out of oil but the initial outlay was so attractive it wouldn't matter if it did. If, in 20 years, those stakes all went to zero, the overall wealth creation was still meaningful, especially relative to alternatives, risk, and taxes. So, point being, if they had been zero-dividend paying companies with similar profiles, rather than going to 1/3rd of capital at the time, I might have limited it to 1/5th or something to account for the fact I couldn't take money off the table without selling shares or writing covered calls.
I have to go ... this is a huge, huge topic. There is no way I could ever condense it to a single comment or even a series of blog posts. It's is as expansive as things I've written about on valuation, case studies, etc. over the years. Again, none of this is investment advice, I'm trying to explain it like I would if I were a professor going over the 100,000-foot view of an area of study. To that extent, I hope at least something in it was helpful or educational.
Joshua Kennon
September 24, 2026
Replying to clobber
P.S. I really do have to run but, in summary, to answer your first question, weightings at the first level are determined by asset/liability matching. That's principle one. The other questions, again, are each their own 3+ hour conversation. I mean there are two or three models you can use for maximum draw-down; a fixed-percentage will be informed by time-sequence risks with equities, which the firewall component I mentioned as part of asset/liability matching mitigates to a large degree, in my opinion, typically no more than 4% but there is a lot of potential adjustment in that number, life expectancy, etc. Usually, if people want to travel, you want to have them do it before they are 70 because at that point, no matter what the intention is, most people become more stationary and stay at home for one reason or another. Not everyone, but enough the presumption should be factored into the math I'd argue; better to take 6% for 5 years then maybe 3% down the road thereafter if it means you get so see Italy, France, Greece, Japan, or whatever your particular list may be.
You just go through these massive mental checklists and then, when all is said and done, I stand back and sit with a portfolio for hours, thinking about the person, what they've shared about their life, the specific cash flows at the underlying components, the weightings in relations to each other, and mentally run through horrific scenarios; 1929-1933, the stock market closing for a year like in World War I, another 9/11 event, etc. I basically ask the question, "If this were my portfolio, and I have the same facts, preferences, and consideration as this client but with all of my knowledge and experience, would I sleep at night?" The answer has to be yes or everything gets shut down until I get it to a place where I feel that comfort.
So there is a tremendous amount of math baked into it but by the time I'm doing the work, and adjusting weightings, it's second nature. I also then look at the equity weightings and compare it apples-to-apples with different lists like the S&P 500. Right now, for example, the S&P is essentially one major concentrated bet in one major industry, the ultimate cash flows of which look really iffy. It's certainly the most concentrated and speculative it's been in my lifetime, or at least since the dot-com era, while other businesses are really, really attractive at present prices. Hence, our capital looks very different than the headline market number with entirely different weightings; e.g., the tobacco structural trade is a double-digit holding to this day for most folks because even though portfolios have grown, they have expanded, too, and are far above the initial cost basis. Yes, there is some overlap - e.g., we have several major tech positions, Meta and Alphabet plus a third unnamed one that is now becoming quite large, bought during brief moments of collapse in the shares because investors thought the companies were doomed and we believed strongly otherwise - but there may be periods where the S&P significantly outperforms us, or we significantly outperform it, I simply do not care to the extent that some of the things happening in the index right now are insane. I would be terrified if my entire net worth consisted of, say, a pile of index funds in a taxable brokerage account. I've seen this movie.
It reminds me of something Charlie Munger once said, you go around trying to make intelligent decisions and you deviate wildly from society or the market, and sometimes you can be out of favor for quite some time but then, and my own life experience has mimicked this, something happens, and all at once you're in the right place, with the right holdings, having avoided the nonsense that infected others. I said it elsewhere in recent days, but my goodness, I'd be terrified if I worked at OpenAI or Anthropic, counting down the days to an IPO because I'd want to take the liquidity as quickly as possible. No matter how many times I run the numbers, I cannot get to any other conclusion that LLMs are mostly going to end up being locally run on company-owned or consumer-owned hardware with little to no moat in the frontier models. The benefit should accrue to the Alphabets and Apples and Microsofts of the world who, over time, just bake it into existing platforms. Other than specialty product (e.g., a company like Thomson Reuters creating a legal LLM model that it provides to law firms and couples with a specific indemnification guarantee), I think paying for tokens with some of these companies is going to be akin to how internet browsers used to function. No one has bought an internet browser, largely, since Microsoft made Internet Explorer free and bundled with Windows, destroying Netscape's business.
And the thing is, all those early internet folks were absolutely right. Their predictions came true. More so, even. They simply lost most if not all of their money in the end and existing, large businesses integrated the improvements; e.g., the internet did not destroy Walmart, it has now made it even more unstoppable. (Valuation on Walmart these days is another question, we're talking about underlying cash flow growth and operational stability.)