Three disciplines, one coherent system. Investment process, retirement planning, tax strategy. They aren't separate services; they're one plan, viewed from three angles. Scroll the whole thing or jump to a section.
Every week, before any portfolio decision, I run through four layers of market health. Each one gets a score. Those scores combine into a composite that tells me, plainly, how aggressive or defensive client portfolios should be right now.
Think of the process the way a skilled physician approaches a complex case. No single test tells the whole story. Blood work, imaging, patient history, what they see in the exam room. Each one alone might mislead. Put them together, and you start to see what's actually there. Miss one, and you miss the diagnosis.
Price-only analysis is the default reflex in markets. Price up, optimism. Price down, worry. Reacting to a single signal is reaction, not analysis. The four-layer process is built to do something different. It reads more than one part of the picture before any decision gets made.
The four-layer process is the alternative. It's what I've spent 25 years refining. It doesn't make me right every week. What it does is make sure I'm asking the right questions every week. That's the difference between a process and a hunch.
Each layer scores from +2 (strongly positive) to −2 (strongly negative). The four scores combine into a composite, which also falls on a five-point scale. The composite score maps to a specific portfolio posture, from "aggressive" on the high end to "defensive" on the low end. Three cautious layers and a fourth layer that's neutral produce a cautious stance. Three constructive layers and a fourth that's stretched produce a constructive stance with a trim on the edges.
That's the mechanism. The work is in the scoring. Once the scoring is done, the positioning is already written. Which means there's no room for a dangerous thing in investing, which is making it up as you go.
Economic conditions, market internals, valuations, sentiment. Each one reads a different part of the same picture. The answer only becomes clear when you look through all four.
Where the economy actually is, not where the headlines say it is. Manufacturing, rates, the dollar, the yield curve, industrial production. These are the signals that show up in portfolio returns months before anyone notices. When the economy is deteriorating, that usually appears in PMI and industrial data well before it shows up in corporate earnings.
The index can look fine while hundreds of stocks are quietly falling apart. This is the layer that reads the body language of the market. Breadth. Advance/decline. Sector rotation. Percentage of stocks above their 200-day moving average. New highs versus new lows. These tell you if the rally is broad or if it's being carried on the back of five mega-caps.
Price determines return. Every time. CAPE ratio, equity risk premium, forward P/E, price-to-book. Valuations don't predict what happens next week. They shape the next decade. Buy at rich valuations and you get lower-than-average returns for a long time. Buy at cheap valuations and you get the opposite. 150 years of data say the same thing.
The contrarian layer. When the crowd is most euphoric, the setup usually isn't. When the crowd is most fearful, the setup usually is. Extreme readings mean-revert. That's the wager. The AAII bull-bear spread, the VIX term structure, COT positioning, put/call ratios. This layer tells you how the boat is leaning.
Each layer scores from +2 to −2. The composite sits somewhere on a five-point range, and each reading maps to a specific portfolio posture. This is what removes emotion from the decision. The work is in the scoring. Once the scoring is done, the positioning is already written.
The scorecard is the engine behind the portfolio, not a publication. I share my current read with clients directly, in the context of their plan, because a number on a website without a conversation is just content. The process itself is what I'll defend.
A process only matters if you can describe what it does across a full cycle. Anyone can look smart in a bull market. The work of a real advisor shows up in the years nobody remembers fondly. Here's what this framework produces over time.
In early bull markets, economic conditions are improving from a low base, internals are strong, valuations are compressed, and sentiment is fearful. Every layer is firing green. The composite reads aggressive or constructive. Portfolios lean into equity. This is when people who "feel uncomfortable buying" end up regretting their caution for years.
In mid-cycle expansions, economic conditions remain positive but start losing steam, internals are mixed, valuations are stretching, and sentiment swings toward complacency. The composite drifts toward neutral. The right posture is strategic allocation, not heroics. Don't chase what's already run.
In late-cycle periods, economic conditions begin to deteriorate under the surface, internals weaken as leadership narrows, valuations are elevated, and sentiment is euphoric. Three layers are flashing yellow or red. The composite moves cautious. This is when most advisors and most of their clients feel the most confident. That's usually the signal to do the opposite.
In bear markets and recessions, economic conditions are clearly poor, internals have broken, valuations have compressed from stretched toward reasonable, and sentiment has turned from euphoric to genuinely fearful. Now three layers are negative and the fourth, sentiment, has swung contrarian-positive. The composite starts moving back up even as prices continue to fall. This is when the process earns its keep.
The same instrument that told you to get cautious in 2021 and 2022 told you to get aggressive in 2009. That's what a process does. It removes the emotional whiplash that destroys most investors.
I use AI two to three hours a day. Not as a gimmick. As a real part of how I work. I use it to score thousands of data points that would take me weeks to process manually. I use it to stress-test my conclusions against prior cycles. I use it to find relationships I might have missed.
AI doesn't change the framework. It accelerates the thinking. Think of it the way a pilot uses a modern cockpit. The plane still depends on the pilot's judgment. But nobody wants a pilot flying without the instruments. Same here. The judgment still has to come from somewhere, and that somewhere is 25 years of watching cycles.
It will not call exact tops and bottoms. Nobody can. Anyone who tells you otherwise is either lying or will be wrong soon. What the process does is keep portfolios positioned appropriately for the risk environment that's actually present. That's worth more than occasional brilliance. That's worth a portfolio that doesn't lose 50% when it easily could have lost 20.
It will not eliminate losses. Markets fall. That's part of the deal. What the process does is make sure the losses are sized correctly for what the environment warranted.
It will not make you rich quickly. Wealth gets built through concentration in one thing done well. Once it's built, it gets kept through the opposite discipline. This process is about the keeping, not the making. If you want the making, you should be running a business, not reading an advisor's website.
Six principles that shape every plan I build. The short version of a long career.
Retirement planning is a discipline that barely existed a generation ago. For most of modern history, people worked until they physically couldn't and then they died, usually fairly close together. Pension plans handled the rest for the people who had them. The idea that an individual should spend decades saving during one phase of life, then spend decades drawing down those savings during another phase, with a plan that accounts for inflation, taxation, sequence risk, healthcare, longevity, and estate transfer, that's maybe 40 years old.
Which means almost nobody your age grew up watching their parents do it properly. There's no cultural muscle memory. The advice industry backfilled that gap with rules of thumb that work sometimes and fail catastrophically the rest of the time. The 4% rule. "You can take Social Security at 62." "Target-date funds will handle it." These are not bad starting points. They are terrible ending points.
Real planning, done well, looks different. It's specific. It's personal. It accounts for the things that general advice can't. And it's built on principles that hold up across the full range of outcomes, not just the average one. Here are mine.
The order of your returns matters more than the average. Two retirees with identical 7% average returns can end up in completely different places depending on when those returns arrive. A bad first decade of retirement can end a plan that would have worked fine with the same average distributed differently. This is the math nobody teaches you.
Buy stocks at a CAPE of 10 and you get a good decade. Buy them at 35 and you get a decade of treading water. That isn't opinion. That's 150 years of data saying the same thing. Starting valuation is the single best predictor of 10-year returns, better than any forecaster, any guru, any fund manager.
The seven years between retirement and RMDs are often the lowest-income window of a lifetime. The tax rates during that window are usually the lowest they'll ever be for the rest of the plan. Missing that window costs hundreds of thousands of dollars in lifetime taxes. Most people miss it because it feels optional. It isn't.
Most wealth gets built through concentration in one thing done well. A business. A career. A property. Keeping wealth, though, requires the opposite discipline. The same concentration that made you rich will unmake you if you don't rotate out of it. The distinction matters more the closer you get to drawing on it.
Married filing jointly has wider brackets than single. When the first spouse passes, the survivor keeps most of the income and loses half the brackets. This is the "widow's tax trap," and it's one of the most under-planned events in retirement. Plan the conversions and the basis work before that day comes, not after.
Everybody's a genius in a bull market. The work of a real advisor shows up in the years nobody remembers fondly. A process is what keeps you from confusing a long bull run with actual skill. It's also what keeps you invested when everything in your body wants to sell at the bottom.
A real plan is not a binder. It's a dynamic set of decisions that changes as your life does. Here's what goes into one.
Every account. Every document. Every goal. Not just the investment accounts. Tax returns, estate documents, insurance, beneficiary designations, employee benefits, real estate, business interests. You can't build a plan around half the picture.
I model the accumulation side if you're still working, and the distribution side for every year of retirement through the survivor's death. Not a single line through a spreadsheet. A stochastic projection across thousands of return paths, including bad ones, to see where the plan is fragile.
Roth conversion schedule. Capital gains plan. Required minimum distribution projection. Bracket management for each year. Survivor bracket planning. Charitable strategies if applicable. This is often where the largest dollar-value planning decisions get made.
The portfolio is built backwards from the plan, not forwards from a model. Your cash flow needs, your tax situation, your risk tolerance, and the current market environment (via the four-layer process) all inform the allocation. Not a generic pie chart.
Your will doesn't control your retirement accounts. The beneficiary form does. We walk through every asset and every designation, and we coordinate with your estate attorney to make sure the documents actually accomplish what you want them to accomplish.
Plans don't sit on a shelf. We review quarterly at minimum, more often if markets or your life warrant it. Tax strategy revisits every November. Beneficiary and estate updates whenever life events happen. The plan is a living document, not a printed one.
A real plan spends as much time on what not to do as on what to do. These are the mistakes I see most often, in rough order of how much damage they cause.
Sequence risk hits hardest in the first few years of retirement. Retiring into a bad market and drawing down on depleted assets is the single most dangerous situation in retirement planning. If you're within two years of retirement and the market is at peak valuations, the planning work is less about what to buy and more about how much cash to hold so you aren't forced to sell at exactly the wrong moment.
For most retirees, the seven years between their last paycheck and their first RMD represent the lowest-income stretch of their adult life. The tax rates that apply during that window are often the lowest they'll ever be. Every dollar converted from traditional to Roth during those years is a dollar that will never be taxed again. People routinely leave six figures of lifetime tax savings on the table here because nobody walked them through the math.
Married couples plan together. When one passes, the survivor moves to single filing, with half the bracket width and generally similar required distributions. That's a stealth tax increase of tens of thousands of dollars per year, often for decades. The planning for this has to happen while both spouses are alive.
Most people who built real wealth did it through concentration. Company stock. A business. A single property. Once that wealth is built, not rotating out of the concentration is how a lot of that wealth gets lost. The S&P 500 has had multiple 40%+ drawdowns in living memory. Any single stock can go to zero, and some have.
I've seen more inheritance chaos caused by stale beneficiary designations than by any other estate planning error. Your will doesn't control retirement accounts. The beneficiary form does. A form naming your ex-spouse from a decade ago overrides a current will every single time.
Most of the highest-leverage planning moves have to happen years before the event they solve for. Pre-sale planning for a business has to start 18 to 24 months before the closing date to work properly. Estate restructuring has to happen while you're healthy enough for it to be considered done with intent. Roth conversions need the low-income years. The window for each of these closes, often quietly, and by the time people notice, the best opportunities are already gone.
The tax code is a set of instructions Congress wrote to shape behavior. Aligning your life with those instructions is not aggressive planning. It's the planning.
The tax code is a set of instructions. Most people read the first page and stop. The savings are on pages thirty-four through seventy-eight.
Here's the thing most people miss: the tax code is the single most overlooked wealth-building tool available to anyone earning real money in this country. Not because the information is hidden. Because it's buried in a document almost nobody reads past the first few pages.
Congress writes the tax code to shape behavior. Save for retirement, and they reduce the tax rate on what you save. Hire employees, and they give you credits. Build something, invest in something, give something, hold something for a long time, and the tax treatment changes dramatically. The tax bill is not handed down like weather. It's constructed by the choices you make during the year.
Most CPAs, good ones included, are primarily compliance professionals. They tell you what you owe after the year is done. They're not designed to tell you what to do during the year to change that outcome. That's where the planning work lives, and that's where the largest dollar-value wins usually happen.
Not every strategy is right for every client. These are the ones that most often produce outsized, measurable tax savings for the types of households I work with.
The window between retirement and required minimum distributions at 73 is often the lowest-income stretch of a lifetime. Tax rates during that window are usually the lowest they'll ever be in the plan. Converting the right amount in each of those years, to the top of a deliberately chosen bracket, can produce six figures in lifetime tax savings. Ignored, it's the most expensive oversight in retirement planning.
Learn moreWhen to claim. Whether to claim early, at full retirement age, or delay to 70. Spousal benefits. Survivor benefits. Divorced-spouse benefits, which most people don't know they qualify for. The difference between a poorly-timed claim and a well-timed one is often six figures over a 30-year retirement. The decision is irreversible for most people, so getting it right the first time matters.
Learn moreLow-basis stock from decades of holding. Inherited assets where step-up basis planning matters. RSU grants that stack up faster than they can be diversified. The capital gains bill on these positions can be compressed with planning: installment structures, charitable strategies, timing to gain-harvesting windows, coordination with Roth conversion years. The menu of what works depends on when we start and what the position is.
Learn moreYou transfer appreciated assets into the trust. The trust sells them tax-free. It pays you income for life. A charity you care about gets what's left. You get a partial deduction on the way in, income on the way through, and legacy on the way out. For the right situation, particularly a low-basis concentrated position and a client with philanthropic intent, it's one of the most elegant structures in the tax code.
Read the white paperYour will doesn't control your retirement accounts. Your life insurance. Your annuities. Your bank transfer-on-death accounts. The beneficiary form does. A stale designation overrides an up-to-date estate plan every single time. This sounds administrative. It's not. This is the single most common source of inheritance chaos and unnecessary tax I've seen in 25 years.
Read the white paperOnce you're past the obvious contribution limits, the advanced strategies take over. Backdoor Roth. Mega backdoor Roth through 401(k)s that allow it. HSA stacking as a secondary retirement account. Real estate depreciation. These aren't gimmicks. They're written into the code intentionally. Your CPA may not bring them up because they're planning moves, not compliance moves. That doesn't mean they aren't available.
Learn moreTax strategy is overwhelmingly a timing game. The right move in the wrong year is the wrong move. Here's when each of the core strategies matters most.
The highest-leverage window is the retirement-to-RMD stretch, typically ages 63 to 72 depending on your situation. Secondary windows include any year with a large business loss, a sabbatical, a bridge year between jobs, or a year with major deductions (like a big charitable gift) that would otherwise go partially unused. The worst years to convert are peak earning years.
The decision window opens at 62 and closes at 70. The right claiming age depends on health, marriage status, other income, and survivor considerations. Most people claim earlier than they should because nobody ran the actual math against their specific situation. The math is almost always worth running.
Start 18 to 24 months before any planned sale of a concentrated position. Appreciated stock, investment real estate, inherited assets with step-up planning implications. The menu of strategies that work is almost entirely dependent on setting them up before the trigger.
Donor-advised funds for flexibility. Charitable remainder trusts for low-basis assets paired with income needs. Charitable lead trusts for significant estate transfer. Qualified charitable distributions once you're 70½ and subject to RMDs. The right vehicle depends on the assets you're donating and the outcome you're trying to produce.
At least every three years. Always after any life event: marriage, divorce, birth, death, remarriage. Also after retirement, after significant wealth events, and after any major change in the estate plan. It's a fifteen-minute task that repeatedly produces six- and seven-figure outcomes.
Implement every year you qualify. These are the simplest large-impact strategies for high earners. Most people who qualify and aren't using them aren't using them because nobody told them they could.
There's a line between smart planning and the kind of aggressive structures that the IRS eventually unwinds with interest and penalties. I stay well behind that line. What I won't do:
I won't recommend captive insurance structures to clients who don't have the legitimate business need for them. Yes, they produce tax savings. Yes, the IRS has made it clear they're scrutinizing them hard. I've watched other advisors steer clients into these and then watched the clients spend years untangling the consequences.
I won't recommend conservation easements of the "syndicated" variety. Real conservation easements serve a legitimate purpose. The tax-shelter versions that got marketed heavily a few years ago have produced a wave of IRS challenges that are still working through the courts. I don't want clients anywhere near that.
I won't recommend overly aggressive Section 831(b) micro-captive arrangements, complicated offshore structures, or anything sold primarily as a "tax shelter" rather than a legitimate business or financial structure that happens to produce favorable tax treatment. The test I use is simple: if this structure would need to be defended in a hostile audit, would I want to be the person defending it? If the answer isn't yes, I don't recommend it.
The strategies that actually work, and that have worked for decades, are the ones I've listed above. They're in the code because Congress put them there. They'll still be there in ten years. That's the kind of tax planning worth building a wealth plan around.
A PUBLIC VERSION OF THE WORK
The retirement calculator at plan.johnkoyle.com lets you stress-test your own numbers against sequence risk, tax impact, Social Security timing, and market valuations. Use it before the first conversation, or instead of one.
Open the calculator →A 30-minute call. No pressure, no pitch. We'll talk about your situation and whether this framework is a fit.