What it also means is that it’s time for a Summer 2026 market recap: What Actually Happened (and why it’s important)

1. A Narrow Straight Can Have a Wide Effect

Oil dropped into the low $70s in June when a ceasefire looked possible, then rocketed past $100 in July when fighting flared back up near the Strait of Hormuz. By mid-August, the ceasefire had quietly expired with nothing to show for it.

Why it matters: Oil is basically a tax nobody voted for. When it spikes, gas and shipping costs climb, inflation gets stickier, and the Fed gets more nervous about cutting rates. You don’t have to watch oil futures to feel this, it shows up in your grocery bill and in how long “high rates” stick around.

In the portfolios: This is basically the reason Rotational exists. Holdings like SHLD (defense tech) and NLR (uranium and nuclear) are designed to catch exactly this kind of geopolitical shock, so when oil and defense headlines get scary, these are the pieces meant to hold up or even climb while everything else wobbles.

2. The Fed Went From a Singular Voice to a Group Debating Whether a Hot Dog Is a Sandwich or Not

Love him or hate him Jerome Powell saw us through one of the most tumultuous and complicated economic times we’ve ever seen. The stakes may have been higher with Bernanke and the Great Recession, but whatever you want to call these last six years they had Powell juggling political, social and economic pressures simultaneously. And the reality is he did a phenomenal job.

New Chair Kevin Warsh has been running meetings all summer, and the “we’re all on the same page” era is over. Most recently three members dissented in favor of a hike in July, first time that’s happened since 2016, and the minutes suggest this disagreement runs even deeper than that.

Why it matters: The Fed sets the price of borrowing money. A united Fed is predictable; a divided one is not, and markets haaaaate not knowing what’s coming. Practically speaking, don’t hold your breath for cheaper loans anytime soon, the timeline keeps getting pushed back.

In the portfolios: This is part of why something like CAOS (a tail risk fund) sits in our fixed income sleeves. It’s insurance against exactly this kind of “nobody knows what the Fed does next” stretch… you don’t need CAOS to pay off every quarter, just the quarters like this one.

P.S. A hotdog is NOT a sandwich.

3. Inflation Cooled Off, Then Got Cold Feet

May came in hot at 4.2%. June cooled things off nicely, down to 3.5%. Then July’s PCE print (the Fed’s preferred measure) ran back up to 3.7%, partly thanks to the oil spike I mentioned above.

Why it matters: Inflation doesn’t move in a straight line, no matter how badly financial media wants it to. But zoom out from the monthly zigzags and the bigger point is this: prices for the stuff you actually buy, groceries, gas, rent, insurance, keep climbing most years, even in months when the “inflation rate” looks like it’s cooling off. Cooling off just means prices are rising a little slower, not that they’re coming back down. That’s why the same grocery run costs more than it did a couple years ago, even though nothing about your habits changed.

The back and forth actually matters beyond just being confusing to follow. The Fed is watching these same swings to decide whether it’s safe to cut interest rates, and a bumpy, unpredictable inflation picture makes them more hesitant to do that. That hesitation is what’s kept things like mortgage rates, auto loans, and credit card rates elevated for longer than a lot of people expected. So when you see inflation reports jumping around, it’s not just a headline, it’s why borrowing money still feels expensive.

For your day to day, none of this is abstract. It's the difference between rates coming down versus staying elevated for longer. And on the inflation side itself, it's a reminder that cash sitting in a checking account, or even a low-interest savings account, is quietly losing purchasing power every year inflation runs above zero. A dollar today buys less than it did last year, and it'll buy less again next year, regardless of which report you're looking at. That's the whole reason "just save it" isn't a full financial plan for anyone, whether you've got $500 or $500,000. Investing exists to try to grow your money faster than prices are rising, so you're not quietly falling behind just by standing still.

In the portfolios: USCI (a commodity index fund), held inside our fixed income sleeves, is one of the more direct inflation hedges you’ve got. When prices for oil, metals, and other raw materials rise, this piece is built to rise with them rather than get squeezed by them.

4. The Job Market Is Sending More Mixed Signals Than Two People Trying to Figure Out if It's the Handshake, the Hug, or the Combo

Hiring fell short of expectations month after month (57K jobs added in June against a forecast of 115K), and unemployment only looked steady because people were leaving the workforce, not because things were actually getting better. By August, some reports showed payrolls going negative.

Why it matters: A cooling job market cuts both ways. It’s a legitimate warning sign for the economy, but it’s also historically the thing that finally gets the Fed to cut rates, which tends to help both stocks and bonds. The tricky part is that it’s landing at the same time as the inflation picture is bouncing around, cooling in June, then running hot again in July. That’s the kind of mixed signal that makes the Fed’s job murky at best. Normally a weakening job market alone would be a clear green light to cut rates. But with inflation still acting unpredictable, the Fed can’t just focus on jobs, it has to weigh a slowing economy against the risk that cutting rates too soon lets inflation take off again. That’s exactly why you’re seeing a divided Fed instead of a unified one, jobs data is pointing one way and inflation data is pointing another, and there’s no clean answer that satisfies both at once.

That’s the bigger picture worth sitting with: the economy rarely hands you one clear signal to react to, it’s usually two or three conflicting ones at the same time, and figuring out which one matters most is a moving target even for the people setting policy. If you don’t already have somewhere between three and six months of expenses set aside in cash, a wobblier job market is as good a nudge as any to get there, not because a recession is guaranteed, but because having that cushion means you’re not personally forced to guess correctly about how this all shakes out either.

In the portfolios: This is the kind of environment core bond holdings like BND and AGG are built for. When the economy shows cracks, bonds tend to get a bid as investors look for safety, which is the ballast function these funds play.

5. Silicon Valley Bet the Ranch on AI But Wall Street Still Wants to Know “Where’s the Beef”

Amazon, Microsoft, Alphabet, and Meta collectively spent roughly $725 billion in AI infrastructure so far for 2026. Investors cheered it through the spring, then spent July asking, essentially, “okay, but where’s the return?” before recent earnings this month (Microsoft’s Azure crossing $100B in annual revenue) helped to settle some of the collective nerves.

Here’s the part that’s easy to miss: the S&P 500 itself barely moved in July, but that headline was actually hiding a lot. Over 300 of the 500 companies in the index actually finished the month well in the positive territory, and nearly 100 of those companies were up by double digits! The index looked flat though because a handful of massive AI names dragged it down enough to cancel out all that strength underneath.

Why it matters: A small handful of companies now make up an outsized chunk of the S&P 500. That means if you own a plain index fund and think you’re “diversified,” you’re more exposed to “does the AI bet pay off” than you might assume, and you can also miss out on strength happening everywhere else, because a few giant names are big enough to drag the whole average down even when most of the index is doing fine.

In the portfolios: This is exactly the kind of month direct indexing is built for. Instead of just owning “the S&P 500” as one blended number that averages winners and losers together, direct indexing holds the individual stocks separately, so you can actually capture the gains from those 300+ companies that were up, rather than having them washed out by the handful of mega-cap names dragging the average down. It’s the difference between owning the average and owning the pieces that made up the average.

6. Investors Got Tired of Tech and Then Remembered Value Stocks Still Exist

After tech led the charge through the first half of the year, July flipped the script. The Nasdaq fell while the Dow, small caps, energy, and industrials picked up the slack. By August, small caps were setting records of their own.

Why it matters: This is the entire case for diversification in one paragraph. If your money was parked entirely in tech-heavy funds, July stung…. but if you also held some value stocks or small caps, you barely noticed.

In the portfolios: This is exactly why Core Equity sleeve doesn’t just hold QQQ. VTV (value stocks) and VB (small caps) sit right alongside it, so when tech has a rough month, you’re not fully exposed to just one side of the story.

7. Long-Term Bond Yields Hit Levels We Haven’t Seen in Almost 20 Years

^{(Truth be told, it’s George’s dinner time and I couldn’t think of a witty title for this one because he is literally just staring at me)}

The 30-year Treasury spiked on deficit worries, sticky inflation, and heavy government borrowing, dragging bond fund returns down with it.

The yield curve is basically a menu of interest rates for different loan lengths, short-term, medium-term, all the way out to 30 years. Normally, longer loans carry higher rates since lenders want more compensation for locking up money longer. This summer, the long end spiked hardest: the 30-year Treasury hit a 19-year high near 5.28%, while shorter-term bonds barely moved. That’s the bond market saying it’s worried about the next 20-30 years of deficits and borrowing, not next year.

Why it matters: People assume bonds are the “safe” part of the portfolio, and they are, in the sense that you get your money back at maturity. But bond prices absolutely can drop when yields rise, which is exactly what happened this summer. The upside: if you’re buying bonds today, whether it’s a new position, reinvesting a maturing bond, or just contributing to a fund that holds bonds, you’re locking in a higher rate than someone would have two years ago. A bond fund that’s been quietly getting hurt on price also means the yield it pays out going forward is now higher too.

In the portfolios: BLV (long-term bonds) felt this the most directly, since longer-dated bonds are the most sensitive to rising yields. BSV (short-term bonds) barely noticed, which is exactly why both sit in the same sleeve together. It’s also why we actively skew how much sits in short versus long-term bonds (”duration exposure”) depending on what we’re seeing in the bond market and across the yield curve.

8. Like a Jam Band Concert That Just Won't End; Tariffs Came Back for an Uninvited Encore

A proposed 50% tariff on Canadian goods and fresh trade tension with China rattled specific stocks in August, while some retailers (like Target) actually got a tariff refund tailwind.

Why it matters: Tariffs create very specific winners and losers even while the broader market shrugs. There’s no clean “tariff trade” or single investment that protects you from this kind of headline, trade policy shifts too fast and hits too unpredictably for that. What actually helps is everything we’ve already covered working together. Diversification means you’re never fully exposed to one sector or one country’s trade relationship. Rebalancing means if tariffs hammer a specific holding, you’re not stuck overweight in it, the process trims and adds along the way regardless of the reason behind the move. And small, calculated positions inside the Rotational Sleeve, rather than big bets on any single trade story, mean that when a tariff headline does sting a specific name, it’s a minor scrape instead of a real hit to the account. It’s less about predicting the next tariff and more about already being built so no single one of them can do much damage.

9. And at the End of the Day: Markets Still Don’t Care

Despite everything above, the S&P 500 crossed 7,800 for the first time in mid-August, and small caps notched new highs right alongside it:

Why it matters: This is the part people always forget, markets climb the metaphorical walls of worry all the time. Scary headlines and record highs happened in the same week. Waiting for “no bad news” before investing is a losing game; time in the market almost always beats trying to time the market.

In the portfolios: SPY, the largest single holding in Core Equity Sleeve, is your direct line to this. This is where rebalancing and dollar cost averaging quietly do their job in the background too. When tech runs ahead of everything else, like it did for most of the first half of the year, rebalancing trims a little off names like SPY and QQQ and adds it to the pieces that lagged, like VTV (value) and VB (small caps), so you’re not left over exposed to a handful of Mega Cap AI companies. Then when the script flips, like it did in July when value and small caps took the lead and tech cooled off, rebalancing works in the other direction, trimming some of the gains from VTV and VB and adding back into SPY and QQQ. Either way, you’re systematically buying low and selling high across your own holdings instead of chasing whichever one had the better month. And if you’re regularly adding to your retirements accounts (through us, through work, or through wherever), dollar cost averaging means some of that money is being used to buy during July’s wobble as much as August’s record highs, so you’re never betting everything on picking the perfect month to invest.

Both are really the same idea just executed in different forms: you don’t have to correctly guess when to buy or when to trim, the process does it for you, month after month, whether the headlines are good or bad.

So what does all this mean?

Put the nine threads together and you get a summer that gave you real reasons for optimism, strong earnings, record highs, better rates on new bonds, and real reasons for caution, a cooling job market, a divided Fed, an oil shock, tariffs flaring back up, all at the same time. That tension isn’t unique to this summer, markets almost always have some good news and bad news pulling in opposite directions, this season just put it on full display. What is true about summers specifically, is that markets tend to quiet down as institutional investors take time off (believe it or not, fund managers going to the Hamptons does genuinely slow the markets down), which historically means fewer big swings on average, but sharper reactions when news does hit, which is exactly what we saw: calm months on the surface, punctuated by sharp moves on oil, Fed dissents, and tariff headlines.

None of us, including me, can tell you with certainty which of these threads will matter the most now, or in the future, and we’re not going to pretend otherwise. What we can tell you is where we’re focusing our energy, and it’s not on prediction. It’s on the things actually within our control: how diversified your money is across stocks, bonds, sectors, and geographies, how disciplined the rebalancing stays so today’s winners don’t quietly turn into tomorrow’s concentrated risk, and how deliberately those positions are weighted so no single surprise can do outsized damage. That’s not a passive stance, it’s an active one, just aimed at what’s controllable rather than what’s predictable.

If there’s a reason for real optimism heading into the fall, it’s this: earnings are strong, the economy is still growing, and even a messy, uneven summer like this one didn’t stop markets from setting new highs. If there’s a reason for continued caution, it’s that several of these threads, the labor market, the Fed’s next move, geopolitical flashpoints, are genuinely unresolved and could go either way. Both of those things are true at once, and that’s ok. It’s exactly why the plan doesn’t change based on which headline shows up first. We’re watching all of it closely, and we’re managing what needs managing, so you don’t have to carry that uncertainty alone.

Now I seriously need to go feed George.

The big thing to know up front is that the saving matters far more than the account you save in. A child whose family sets money aside early will do well in a Trump Account, a 529, or a plain taxable account. The government keeps rolling out new ways to save for kids, custodial Roth IRAs, 529 plans, and now Trump Accounts, but none of them is one-size-fits-all. What you are trying to provide for your child, and when they will need it, shapes the answer more than the name on the statement. So the real question is not “should I use the new account,” it is “what am I saving for, and which account fits that goal.” Let’s walk through it.

First, what is a Trump Account?

Think of it as a traditional IRA with a twist. You can open and fund it for a child from birth through the year they turn 17. During that window, money goes in but nothing comes out. Starting the year the child turns 18, it behaves like a normal IRA: penalty-free withdrawals at 59½, the usual exceptions for things like a first home or education, and the option to convert to a Roth.

Three features make it unusual. Anyone can contribute, up to a combined $5,000 a year. Employers can chip in up to $2,500 of that. And unlike a regular IRA, the child does not need a job or earned income to have one funded on their behalf.

Is the $1,000 really free?

Yes, but here is where people get tangled up. Eligibility and the $1,000 are two different things. Any U.S. citizen child with a Social Security number can have a Trump Account opened for them, at any age under 18. The $1,000 is narrower. The government only seeds accounts for children born between 2025 and 2028. So your older kids can still have an account, they just will not get the free deposit.

The seed itself is simple. It does not count against any contribution limit, and you do not have to match it. You do have to claim it, by filing Form 4547 or signing up at trumpaccounts.gov.

On top of that, some employers and a handful of charities are funding accounts too. If any of that is available to your family, take it. Money that compounds untouched for decades is worth claiming, full stop.

What about putting in my own money?

Here is where the shine comes off a little, and where most of the questions get interesting.

A Trump Account grows entirely tax-deferred, which sounds great until you remember the bill comes due later. Every dollar of growth eventually comes out taxed as ordinary income, at whatever rate your child pays decades from now. Fund one aggressively from birth and you could hand your kid a seven-figure pre-tax account by retirement. That is the same tax knot we spend our days helping older clients untangle from their large IRAs and 401(k)s. A good problem to have, but a problem.

There are two quieter traps worth naming.

The first is basis tracking. The dollars you contribute are after-tax, so they should come back out tax-free someday. But proving that means filing the right form every single year, potentially for 40 years or more, across a handoff from you to your adult child. Miss it, and the IRS treats the entire withdrawal as taxable. People lose track of IRA basis all the time, and this account stretches that risk over a lifetime.

The second is the Roth conversion dream. The popular idea is to convert the account to a tax-free Roth when your child turns 18 and has little income. The catch is the “kiddie tax.” For a dependent child, income above a small threshold gets taxed at the parents’ rate, not the child’s. So a college student with high-earning parents cannot quietly convert a big balance at a 0% rate. They usually have to wait until they are out of school and earning on their own, by which point they are converting at regular rates anyway.

Trump Account vs. 529 vs. custodial account: which one wins?

This is the question we hear most, and the honest answer is that it depends on your family. That is not a dodge, it is the whole point. Two households with the same income and the same age kid can land on completely different accounts, because they want different things for those kids.

If you are saving for college, a 529 is still the better tool. It is built for education, and it can roll up to $35,000 into a Roth IRA completely tax-free, something the Trump Account cannot match.

If you want flexibility, a plain taxable custodial account, a UTMA or UGMA, is hard to beat. Our friends at Kitces ran the full after-tax math on this, and the result surprises people. A taxable account can actually end up worth more than a Trump Account after taxes, because gains can be harvested at a 0% rate while the child is young, and the account gets a step-up in basis if it is ever inherited. It is also far more flexible. The money can be used at any age, for a home, a business, or anything else, instead of being locked up until 59½. The tradeoff is that a custodial account counts as the child’s asset for financial aid, which can reduce need-based aid, so it is not right for every family.

And if your child has earned income, even from a summer job, a custodial Roth IRA is often the most powerful option of all.

So what should you actually do?

For almost everyone, the first move is the same. Grab the free money. Claim the $1,000 if your child qualifies, and accept any employer or charitable contributions on offer. That decision is easy.

The harder decision, putting your own money in, deserves a real conversation rather than a reflex. Sometimes a Trump Account is the right home, especially for families who have already funded college and want another tax-advantaged way to pass wealth to the next generation. Often a 529 or a custodial account fits the goal better.

One human thing sneaks up on people too. A well-funded account becomes your child’s to control at 18. That is a conversation to start early, not a surprise to spring at a graduation party.

The bottom line

Trump Accounts are a real opportunity wrapped in a lot of hype. The free money is genuinely free and worth claiming. Beyond that, the new account is one good tool among several, not an automatic upgrade. The government will probably keep inventing new ones, and that is fine. There is no single right account, only the right account for what you want to give your child and when. What matters most is starting early, in whatever vehicle fits that goal.

If you have a child or grandchild and you are trying to figure out the right move, that is exactly the kind of question we like. If you already work with us, reply and we will fold it into your plan.

I did the math last year for fun (and because I have a problem), and leaving aside inflation adjustments and the time value of money, he left somewhere north of $150,000 on the table. Poof. Gone. Not because he was irresponsible or uninformed. He did what almost everyone does: took the money when the government offered it and figured that was probably fine.

He was wrong. And so is basically everyone who gives you the same advice.

Here’s what nobody explains clearly: when to claim Social Security is not a guessing game about how long you’ll live. It’s not really even a personal finance question. It’s a fixed income allocation decision. And when you look at it that way, the math gets almost embarrassing in how lopsided it is.

The Break Even Nobody Talks About

Most financial advisors, when they explain Social Security timing, reach for something called the “breakeven age.” The idea is simple: if you claim early (as young as 62), you get smaller checks for longer. If you delay (up to age 70), you get bigger checks starting later. At some point the cumulative totals cross over. That crossover is the breakeven.

For most people, the break even age is somewhere in the early-to-mid 80s.

The conversation usually stops there. “If you live past 83, delaying wins. If you die earlier, claiming early wins.” This sounds reasonable. It’s also the wrong frame.

The right question isn’t “when do I break even?” It’s “what would I have to earn on my portfolio to match what I get from delaying?”

Researchers have started calling this the breakeven real rate, the inflation-adjusted return your investments would need to generate, every single year, to produce the same real income as if you had simply waited to claim Social Security.

Here’s where it gets uncomfortable.

For anyone planning to live to 90 (not an unreasonable target if you’re reading this in your 50s or 60s and in reasonable health), the breakeven real rate, the hurdle your portfolio has to clear, is roughly 5% to 7% above inflation.

Current 30-year TIPS yields sit around 2.5%.

In plain English: to make early claiming the smart financial move, your portfolio would need to outperform what the government is essentially guaranteeing you by 2.5 to 4.5 percentage points, every year, for the rest of your life. That’s not a return expectation. That’s a prayer.

The Interest Rate Quirk That Should Make Your Brain Hurt

Here’s the thing about Social Security that is genuinely weird, and I mean this in the nerdiest possible way.

Almost every income-generating asset in the world is priced based on prevailing interest rates. When rates are high, bonds and annuities pay more. When rates are low, you pay more to get the same income stream. Supply, demand, discount rates, the whole apparatus.

Social Security doesn’t work that way.

The step-up you get for delaying (roughly 6-8% more annual income per year you wait) is fixed. It doesn’t move when the Fed cuts or hikes. It doesn’t respond to Treasury yields. The government says “wait one year, get 8% more forever,” and that number is the same whether we’re in a 2% rate environment or a 6% rate environment.

What this means practically: the lower rates go, the better delaying looks relative to every alternative. Because every alternative is offering less. Government bonds are less compelling. Annuities are more expensive to purchase. And Social Security is sitting there with the same fixed 8% step-up, looking increasingly like the best deal in fixed income.

Nobody building an annuity product or a bond ladder can price their offering without knowing where rates are. Social Security doesn’t have to care. And it almost entirely favors the people who wait.

Who Benefits Most (And It’s Probably Not Who You Think)

The break even analysis changes based on who you are, and a few things stand out.

Women benefit more than men. This isn’t complicated. Women live longer on average, so the longevity hedge that comes with a larger Social Security check is worth more. Social Security’s formula ignores this actuarial reality entirely. It charges everyone the same price for delayed benefits. Women are getting a relative bargain.

The higher earner in a married couple benefits most of all. When a spouse dies, the surviving partner inherits the higher of the two Social Security checks. Whichever earner waited longer and built the bigger monthly benefit essentially locks in a larger lifetime income floor for the household, because one of those checks is going to be paid out for a very, very long time.

The first year after full retirement age (FRA) is disproportionately valuable. This is the one most people miss. Social Security’s step-up structure actually makes the jump from FRA to FRA+1 more valuable in percentage terms than later years. The 8% per year figure sounds linear, but it’s 8% of your full retirement benefit amount, which means as a percentage of what you’d actually be collecting each year you wait, the relative gain shrinks slightly over time. Year one after FRA punches above its weight. If you’re on the fence and close to your full retirement age, that year is probably worth the wait.

The Part That Has Nothing to Do With Math

Here’s what breakeven rates and portfolio return assumptions can’t capture: Social Security is the only retirement income stream that simultaneously hedges both inflation and longevity. That combination is genuinely rare. You can build a TIPS ladder that protects against inflation. You can buy an annuity that protects against outliving your money. You cannot easily find something that does both at scale without either enormous expense or meaningful credit risk.

A bigger Social Security check, locked in for life, adjusted for inflation every year, with no counterparty risk, is a different category of asset than anything your brokerage account holds. The question isn’t “do I need the income now?” The question is “how much of my retirement floor do I want protected against the two things that most commonly wreck retirement cash flow plans?”

Every year you delay is essentially buying more of that protection at a price the market could never match.

What To Actually Do With This

None of this means everyone should delay to 70. There are situations where claiming earlier makes sense: known health issues that reduce life expectancy, immediate cash flow needs that can’t be covered otherwise, complex spousal benefit timing that creates a different optimal strategy. This stuff is genuinely situation-specific.

But if you’re sitting here in reasonably good health with a financial plan that doesn’t require Social Security income to survive between 62 and 70, the default bias should be to wait. The math says so. The interest rate environment says so. The longevity hedge says so.

The instinct to grab the money while you can is human. It’s also expensive.

My grandfather took his check the first day he could. He had 29 more years to live with the consequences of that decision. I’m not going to make the same call. And if you’re a client reading this and haven’t run your own Social Security scenario yet, that conversation is overdue.

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Social Security claiming decisions involve complex individual factors including health, income needs, spousal benefits, and tax implications. Iconoclastic Capital Management is an SEC-registered investment adviser. This content is for informational purposes only and does not constitute tax or legal advice. Please consult a qualified advisor regarding your specific situation.

A mid-level engineer in 2021 could quit on a Tuesday and start a better job the following Monday, the way you change lanes on an empty highway. The same engineer in 2026 has a layoffs tracker bookmarked and refreshes it with their morning coffee. Nothing about the engineer changed. Their skills didn’t erode and their reviews didn’t crater. What changed was the deal, and the deal got rewritten while almost nobody was reading the fine print.

For most of the last seventy years, a big company worked like an insurance carrier you didn’t know you were paying. You handed over your loyalty, your nights, your “sure, I’ll take the on-call,” and in exchange the firm absorbed the volatility of your career. Bad quarter? They ate it. Reorg? You got slotted somewhere. The premium was your tenure and the payout was stability.

That policy has been quietly canceled, you are now carrying the risk you used to be insured against, and most people are still paying premiums on coverage that lapsed somewhere around the end of free money.

Two things drove it. First, the pandemic-era hiring binge of 2020 through 2022, when capital was free and every company hoarded engineers like canned goods before a storm, came with the predictable hangover.

Second, a real slice of knowledge work is now something an AI model does instead. If your day is first drafts, summaries, and tidy analysis, you are not insured against that one either.

None of this is personal, and that is exactly why it’s dangerous. The company feels no cruelty about any of it. It is an organism optimizing under new constraints, and it will mark your role to market every single quarter whether you show up to the exercise or not. The mistake smart people make is running on Org-Chart Brain (tenure, relationships, fairness, the story of how hard you work) while the building upstairs runs on Spreadsheet Brain (a number, a function, a line that either clears the hurdle or it doesn’t).

Phase 2: The Vibe Shift

Part 1 was about building the bunker while the checks still cleared. This week is harder. The tactics are simple enough. The hard part is that Phase 2 asks you to act on information your own brain is working overtime to talk you out of.

This is the phase where most people blow it.

You feel the change in the wind. You notice the all-hands got weird, the budget got tight, the new VP keeps saying the word “focus” like it’s a personality trait. You know, somewhere in your gut, that something is off.

And then you do absolutely nothing.

Instead you tell yourself a story. My team is different. My manager loves me. My project is core to the strategy. The new VP really gets it.

Let me save you some time. When a CEO says “we need to do more with less” on an all-hands, your project just became a row in a spreadsheet, and somebody in a glass conference room is hovering a cursor over the delete key while eating a $19 cobb salad. That is the whole movie. You’re just watching it with the sound off and pretending it’s a different film.

The good news is that this Vibe Shift is loud, if you’re willing to hear it.

The canaries

• The “efficiency” pivot. The all-hands stops talking about growth and starts talking about “operational discipline” and “doing the hard work to focus.” That is your cue to start answering the recruiter emails you’ve been archiving unread.

• The org-chart Tetris game. A new VP appears. Your skip-level changes twice in six months. Your team gets “realigned” into a business unit nobody can explain without a diagram. Somebody is redrawing the map, and you are not in the room where it’s happening.

• The hiring freeze with a better name. “We’re being thoughtful about headcount.” Translation: cuts are coming, and they’d prefer you not start interviewing yet.

• AI rollouts that overlap with your function. The actual canary. If your company just signed a big enterprise Claude or Copilot deal and your day is mostly first drafts, summaries, and routine analysis, the calendar is shorter than you think. Nobody is going to send you a memo about it.

• Glassdoor going sideways. The people leaving anonymous reviews are rarely the top performers. By the time they start sounding scared, the top performers already left, quietly, with a new badge.

One signal is noise. Three or more at the same time is a pattern. When you hit three at once, the watching is over and the moving begins. Here is the order of operations, and it starts in an uncomfortable place.

Step 1: Schedule the 1:1 you keep skipping (with yourself).

Before you fire off a single application, you owe yourself the one meeting nobody ever puts on a calendar: an honest conversation with yourself about where you actually stand.

This is the hardest move in the playbook, because your ego has a vested interest in lying to you. Every aging veteran is sure he has three good years left, and almost none of them do; the survivors are the rare few who can sit in a dark room with their own game film and admit the first step is gone. Your ego would rather you believe you’re indispensable than admit you might be the expiring contract the front office is quietly shopping. So scout yourself the way a GM scouts a bloated deal in a cap crunch, and ask the questions you’ve been ducking:

• If I were the one running the numbers, would I cut my own role? What does my job actually produce, and could a competent person with Claude open in the next tab reproduce 80% of it by Thursday?

• Am I paid above market for what I do today? Comp that floated up during the boom is a bright target in a cost-cutting cycle. The spreadsheet sees a big number, not your tenure or your loyalty or the all-nighter you pulled in 2023.

• Are my skills current, or have I spent three years coasting on a system I built in 2022 that mostly runs itself?

• Who actually picks up the phone if I call them for a job tomorrow? If that list is short, that is the real emergency, bigger than the cash one.

The point is to see the board clearly while you still have moves to make. Beating yourself up is optional and useless. Clarity is the entire game.

A lot of you have let the company badge quietly become a personality. Park it. Evaluate the job like an asset on a balance sheet, because that is exactly how the company is evaluating you. Zuckerberg didn’t brand 2023 his “Year of Efficiency” for the poetry. Efficiency is the corporate word for your salary, specifically.

Self-awareness is the cheapest insurance you’ll ever buy, and the most uncomfortable to pay for.

Step 2: Start interviewing now, even with zero intention of leaving.

The best leverage you will ever have is a real offer in hand while you are still employed.

Worst case, you turn it down and walk away with a fresh, honest read on what you’re worth. Best case, you step onto the next roof before this one catches fire and skip the six-to-nine-month unemployment gauntlet entirely.

An outside offer is the closest thing corporate America has to a restricted free agent’s offer sheet. It is the one piece of paper that forces the incumbent to either match or let you walk, and either way you finally learn what you’re worth to them. “I love it here, but I just got an offer for $X plus a sign-on” produces a counter, a retention grant, or at minimum a much clearer picture of how the company really values you. None of those outcomes are bad. Use it.

A quieter truth: interviewing is a skill that atrophies. If your last loop was four years ago, you are the guy who hasn’t taken a meaningful shot since the last contract cycle, and you will feel it the second the lights come on. Better to knock the rust off now, on someone else’s clock, than when your mortgage depends on it.

Step 3: Pull forward everything you can.

This is garbage-time money: unglamorous, easy to wave off, and it all counts exactly the same when the final whistle blows. Collect every dollar that is already yours before the buzzer.

• RSUs vesting in 60 days and the rumor mill is loud? Do not quit a week early to start somewhere new. Stay. Let them vest. The new employer will wait, because start dates are far more negotiable than people think. Nobody is going to respect you more for walking away from a guaranteed vest.

• ESPP purchase coming up? Let it go through and sell at the lookback. You already earned that discount, so don’t leave it on the table out of politeness.

• Unused FSA dollars? Spend them. “Use it or lose it” has never been more literal.

Step 4: Fix your concentration problem.

We covered the why in Part 1: a pile of your employer’s stock is a leveraged bet on your own continued employment. You are already all-in on this franchise. Your paycheck, your bonus, your health insurance, your Tuesday, all of it rides on this one team not collapsing. Stacking your net worth on the same logo is the financial version of a die-hard betting his mortgage on the team he already bleeds for. When it goes bad, it goes bad everywhere at once.

Phase 2 is about the when, and the when is now, while you still have income, options, and a cool head.

Here is the pattern I see constantly with newly laid-off tech wealth: “I should have diversified two years ago, and now this severance window is my only chance to do it without a tax bill stacked on top of the job loss.”

A 23.8% federal long-term gains rate plus state tax stings, but a round trip back to zero stings a great deal more. One of those you can plan for. The other one just happens to you, usually in a single quarter.

If your employer’s stock is north of 25% of your liquid net worth, the next few weeks are your window to move. Waiting it out is the expensive option.

The Bigger Picture

Phase 1 was about money. Phase 2 is about ego, the harder account to manage.

Every move in this post runs into the same wall: your gut will call it disloyalty, or paranoia, or quitting. So smart, capable people sit still and watch the signals stack up, because moving first means admitting the thing they don’t want to admit. Your gut is wrong, and your gut also does not pay your mortgage. Knowing where the exits are is basic professional literacy, and the time to find them is before the all-hands invite hits your calendar with no agenda attached.

You don’t have to become a cynic about it. You just have to be early. The people who come through a layoff in good shape are almost always the ones who read the room early, kept their dignity, and lined up the next thing while everyone around them was still insisting the new VP “really gets it man.”

Part 3 soon: the badge stopped working anyway. What now?

Something at the front of my mind lately has been the amount of clients we have been talking through layoffs through the lens of their financial plan.

I was still in college in 2008, and while the current environment feels nowhere close to that, this is the first time in my fifteen years in the business that layoffs feel like a trend rather than an event.

We have worked with 7 families through layoffs in 2026 and they are mostly higher earners like engineers, PMs, designers, and ad-sales people.

However, the most disturbing part is this new genre of laying people off. Call it what it is: the performative white-collar execution.

Layoffs as content. Termination as personal branding for leadership so the CEO can beg the audience to clap for his fucking vulnerability.

I think it’s one of the ugliest things happening in American business right now, and it’s been so normalized we’ve stopped noticing how bizarre it is. Forty years ago, executives doing layoffs at least had the decency to look ashamed. Now they’re posting about it like a personal growth arc.

Spoiler: the machine has slowed down. Actually, the machine is starting to make a weird grinding noise, and the guy who owns the machine is, as previously discussed, doing a brand-new mindfulness plunge cooldown routine on his social media.

The question is always some version of: how worried should I be, and what should I actually do if this happens to me?

So I put together a playbook for what I feel are the 3 phases of the current layoff environment.

1. Today’s Post: How to build your bunker while the paychecks are still hitting

2. Next Week’s: How to embrace your self-awareness and read the writing on the wall.

3. Part 3 Soon After: You’re already fucked. What now?

Phase 1: Build the Bunker

This phase requires you to take action while everything is fine, which can feel like the financial-planning equivalent of buying flood insurance in Phoenix.

The best time to prepare for a layoff is when your performance review is full of words like “trajectory” and “high-potential.” Because by the time those words become “headwinds” and “right-sizing,” you’re already down 30 with five minutes left and the coach is pulling the starters.

How big should your cash reserve actually be?

The 3-6 month1 emergency fund rule can be misleading. That math came from an economy where people found new jobs in eight weeks because there were fewer of them, less AI, and a corporate desperation to hire normal people.

Also, it shouldn’t be a catch-all - everyone’s life is different and their needs should adjust accordingly.

Here are variables we consider when recommending emergency fund amounts.

Baseline

Start with 6 months then +- months based on your situation.

Core adjustments

1. Children: +1 month each

2. Occupational volatility: + 1-3 months (commission, equity, or contract pay)

3. Health Concerns or expensive prescriptions: +1-3 months

4. Spouse/partner’s income: -1 to -3 months (zero discount if you’re both in the same industry)

Housing

1. Mortgage, as % of monthly expenses2

   1. 25-40% = +1 month

   2. over 40% = +2-3 months

2. Rent, as % of monthly expenses

   1. 25-40% = +0-1 month

   2. Over 40% = +1-2 months

The math on a real Brooklyn household

Meet “Jenna”. She’s 34, an L5 software engineer at Google making about $400K all-in (base plus a stack of RSUs). Her husband “Mike”, 35, teaches at a charter school and pulls $80K. One kid, “Theo:, age 2, who has asthma (maintenance inhaler, a pulmonologist twice a year).

They rent a 2-bedroom in Prospect Heights for $5,800 a month and have no plans to leave Brooklyn before Theo starts kindergarten.

So, Jenna and Mike need to have $135,000 in an established emergency fund in this example.

Park this money in a high-yield savings account paying 3.5% APY3. NOT in your brokerage sweep or checking account, which is earning you roughly a quarter of a percent.

Stop letting your employer be your only bank.

Your paycheck, your RSUs, your ESPP, your 401(k) match, and probably your equity-heavy brokerage account are all denominated in the same currency: your employer’s continued affection for you.

When the layoff hits, it hits all of those at once. The stock drops (because the layoff signals weakness), your unvested RSUs evaporate into the ether (those were a promise, not an asset, and the promise is now void), your ESPP loses its discount, your 401(k) match stops, and you’re trying to job hunt while watching your net worth get its teeth kicked in over the course of a single calendar quarter.

Concentrated single-stock exposure above 15-20% of your liquid net worth is a leveraged bet on your continued employment. Diversify before you need to.

The actual tools for doing this realistically include:

• Just effing sell when they vest! Set a reminder and do it.

• 10b5-1 plans4 (a preset selling schedule that pre-empts insider-trading concerns)

• Exchange funds (swap your concentrated stock into a diversified pool without triggering the gain) like Cache5

• Direct indexing with tax-loss harvesting

This is a long conversation. We have it with clients constantly and it takes a while to build the full strategy, so don’t be discouraged.

Map your benefits like you’re planning a bank job

Sit down with your benefits portal one weekend, pour yourself something brown, and actually understand the following:

• When do your next RSU tranches vest? If layoffs are rumored, this is the single most important piece of information in your entire financial life.

• What does COBRA actually cost? Get a real quote. The number is going to make you laugh, then cry.

• Check for a Mega Backdoor Roth (the after-tax 401(k) contribution that converts to Roth). This is the single best retirement tool most people don’t know they have

  • Do you have access to one, and have you been using it?

  • If layoffs are looming, max it before the badge goes dark. That window closes the second you’re out.

• HSA balance: have you actually been investing those dollars, or letting them sit in the cash sweep earning enough to maybe buy an Uncrustable?

• What does severance look like at your tenure level? Glassdoor, Levels.fyi, Blind. Real data is out there, so use it for your benefit.

Take the medical stuff seriously

While you have your good, cheap employer health insurance, use the hell out of it. Every doctor’s appointment you’ve been putting off. Every dental procedure your hygienist has been hinting about. New glasses, backup glasses. Refill every prescription to the max.

If you’ve been thinking about therapy, start now. Finding a new therapist while unemployed and stressed and trying to figure out whether your COBRA covers them is its own special hell, and the wait times in major cities are bordering on absurd.

COBRA can run you $2-3K a month for a family. Every uncovered medical thing you push into the post-layoff window is money straight out of the bunker.

The number of phone calls I’ve made to insurance companies in the last few months would make a 1970s switchboard operator weep.

The Bigger Picture

For about fifteen years (roughly 2010 to 2025) there was an implicit handshake inside the new economy. You worked hard, you delivered, maybe you even got equity, the equity went up because the sector was in the middle of one of the great asset bubbles of human history, and the company “took care of you.”

The trade was loyalty for opportunity, and both sides held up their end mostly because the music never stopped.

The music is stopping babe, so build your bunker. Take care of your own goddamn self. Nobody is coming to save you. And you don’t need them to.

Part 2 next week: how to read the writing on the wall

As I think forward to the months ahead, I’m excited to unplug and see what has happened upon my return to the real world.

Like what will Rudy Giuliani get arrested for next? Or will we have solved the AI water supply issue by feeding them1 Gatorade instead?

In This Issue

• Firm Updates + our new mission

• People moves

• By The Numbers

• Resources for You

• Portfolio Updates

🏛 Firm Updates

If you don’t know it by now, I should explain that we approach the financial planner to client relationship a little different than most.

Contrary to others, I believe we are in the hospitality business just as much as we are in the financial services business. A life of serving is a noble one, not one to be looked down upon.

With that in mind, I feel it’s important that you, as our shareholders, get to share in our wins too.

If you stop and think about how much you genuinely want your financial planning team to make, the honest answer lands somewhere between "I hope they stay in business" and "I hope they're not buying a yacht with my money." We're aiming for that exact middle.

We are wrapping up our 6th year as a firm and I want to walk you through a few milestones I haven’t shared before.

🎢 Enjoy The Ride

We sat down to define our core mission statement recently and, if you’ve ever had to do this, it sucks. How dare you try to define everything we stand for and our complex existence as humans into a short phrase? Shakespeare could never.2

After many arguments, there is no better mission statement for Icono Capital than “Enjoy the Ride”.

One of the reasons our approach is different than most is that we are actively growing our organization and willingly taking less profit per person. Why? Because building something meaningful that outlives our careers together is more valuable than extra income.

That sounds like a lot of lip service, but the truth is I need this framing so you understand how we think about the future.

What is the point of building a hyper efficient, high stress firm with 1-2 people just to make a shitload of money and burn out early with nobody to share it with? I’d rather enjoy the ride baby, and that ethos shines through to our approach to financial conversations with our clients too.

People

With our core mission in mind, I had to take a hard look at how we were currently operating to find opportunities to improve. Here is what changed:

Gene Thompson, CFP® promoted to Lead Financial Planner

As the founder of our company, I was kind of the presumed defacto lead planner despite Gene’s knowledge base always being ahead of mine. Making the title official gives you the signal of trust we’ve always had in him to deliver the best we can offer.

Matthew Scott promoted to Chief Operating Officer

Matt is the reason the trains run on time around here. We often joke that we never had an adult in the room until Matt showed up and bestowed upon us all of his corporate jargon experience.

We couldn’t be more excited for him to help shepherd Icono into its new chapter of growth. I’m not much of a religious or cosmic person, but I do believe Matt found us at the right time for a reason.

Snider hired as Cryptocurrency and Analytics Consultant

Have you ever met somebody who just seems to know a lot about everything? That's Matt. I met him on a cryptocurrency panel we did in Chicago last year, and since then he's quietly become one of the most valuable resources our team has. So we made it official. We've partnered with his firm, Block 3 Strategy, to bring Matt on as a part-time consultant, available directly to you for the complex cryptocurrency and financial-analytics work most planners politely pretend doesn't exist. Cold storage, on-chain yield, tax lots scattered across a dozen wallets, the stuff that makes a normal CPA's eye twitch. If it lives on a blockchain or needs a sharper analytical brain than the rest of us can offer, Matt's your guy. If you want to know more about him, subscribe to his substack below.

BitFinance with Matthew Snider

Where traditional investment discipline meets digital assets. Written for the curious, the skeptical, and the quietly building.

📊 By The Numbers

So, how is Icono Capital doing as a whole? I think it’s important to be transparent about our situation given how trusting our clients have to be with their livelihood in exchange.

Below are 3 numbers measuring across different areas of our business you should find helpful.

155 - Total Client Households

We get asked constantly: how many clients do you have? We count it in households (one for a family, one for a single individual).

Back in 2020 we worked with roughly 600 households at Northwestern Mutual and brought 45 of them with us to start fresh at Icono.

• 2020 (year end): 46

• 2021: 57

• 2022: 72

• 2023: 88

• 2024: 112

• 2025: 140

• 2026: 155 (through May)

We're now spread across 18 regions now. 77% of you are in New York (89 households upstate, 31 in the city), with the other 35 scattered everywhere from California to Florida to Dorothy’s House (Kansas).

22 - Project Engagements (Since 2025)

Quick housekeeping note for the long-timers: the way we package our ongoing work has changed. We now run two relationship tiers, GWM Essentials and GWM Premier, and you can see the full breakdown at iconocapital.com/services. None of it changes your engagement.

The one I actually want to talk about is newer: Project-Based Planning.

Not everyone needs (or wants) an ongoing relationship. Plenty of people are perfectly capable of running their own plan and just want a sharp second set of eyes, a roadmap, or help with one big decision: a 401(k) rollover, a retirement-income projection, a Roth conversion analysis, an equity comp divest. So we built a one-time, scoped engagement for exactly that. We work together for 3-6 months and off you go.

Since we added it in 2025 we’ve done 22 of these! Every one of them for someone we otherwise would have had to turn away. Twenty-two households who didn’t fit the old all-in-or-nothing mold and now have a real plan, because there was finally a door their size.

Which brings me to my one ask. You almost certainly know somebody who’s sharp with money, allergic to the phrase “hiring an advisor,” and sitting on one gnarly decision they keep kicking down the road. That person is the perfect project client. Send them our way. It’s the lowest-commitment, highest-value introduction you can make.

38% - Six-Year Revenue CAGR

This is the one I’m proudest of, and the one I have to be very careful with how I present it.

There are thousands of reasons Icono shouldn’t be in business still. I’m not being hyperbolic, the three of us had barely enough money to live on when we took this leap. Living that reality has kept our focus clear and gives us the ability to not give a shit about passing up an opportunity that would compromise what we stand for.

Since we opened the doors, our revenue has compounded at 38% a year, six years running. The typical advisory firm doesn’t grow anywhere close to that. We’ve been expanding at more than four times the industry’s pace.

I’m telling you because that growth is exactly what funds the promise from a few sections up. We take less profit per person on purpose, then pour the room that growth creates back into the firm: hiring ahead of where we are, better tools, and a deeper bench than a shop our size has any right to have. Grow the pie, and everyone at the table eats better. Especially because we know what it’s like to live on crumbs.

Resources for You

A few tools we’ve put real money and time behind that you may not be aware of!

📱 Text Us

Easiest one first. You can text us at (585) 504-1616. It goes to a central platform we can all see!

Income Lab

Most people in retirement obsess over whether they have enough. The harder question is how much you can actually spend without blowing it, and Income Lab answers that one in real time. Dynamic guardrails tell you when there's room to spend more and when it's time to ease off.

For anyone that is interested in testing their retirement plan through a different lens, reach out! We can set up Income Lab for you.

Monarch Money

Listen, budgeting tech is inherently lame. But this is the least lame of them all and we will pay for it!

Bonus mention: it now has enabled features for business owners. It is perfect for solo or small company setups that hate Quickbooks as much as I do.

Hazel

This one’s my favorite and the newest. Hazel is tax projection and planning software that our Custodian, Altruist launched this year. It’s so effing good that we were able to cancel three other subscriptions saving us thousands per year in tech.

In one sample review it dug up north of $30,000 in refunds and amendments that were missed. Your old CPA isn’t going back to re-read your 2021 return. Hazel does.

Portfolio Updates by

With Chris heading out on paternity and me not having sent anything out recently, this felt like the right time to cover a few things.

First, I’d like to send out something like this more frequently, covering some of the broader topics happening economically, financially and most importantly NOT politically. But if there are things you’d like to see or topics covered shoot me an email, because chances are you’re not the only one, and I’ll try to bake it into the newsletter.

Next I’d like to cover what’s been going on inside the sleeves that make up your portfolios:

Overall we’ve seen a ton of volatility to start the year; new fed chairs, old wars becoming new, and new wars potentially coming to a cease fire. These have dominated the headlines, and been the driving factor in returns so far this year. BUT volatility can be a good thing too, it can even be an opportunity for us to harvest losses in taxable accounts, get better entry and exit points inside our equity comp plans, and even time Roth conversions too. Meaning there’s always something positive we’re able to do, even when everything else is negative. That being said, lets dive in:

• Core equity: This is where the bulk of your assets are invested and it has been incredibly consistent already up over 14% YTD, compared to the S&P 500 which is up “only” a little over 10%.

• Rotational: The rotational has been another bright spot for our clients up roughly ~16% YTD and showing no signs of slowing, with the primary thesis of AI related hardware, rare earth elements, digital infrastructure, and the energy needed to power all that leading the returns.

• Fixed income: The fixed income sleeve has been steady Eddy, but the bond market still remains pretty chaotic, returning only 1.37% but compare that to the your average total bond ETF that’s up less than ~0.15%. The reason being interest rate and inflation concerns, which has led to a lot of volatility and chop in the bond market specifically.

Inflation and Economy:

First-quarter GDP accelerated to 2.0%, which says the underlying economy is resilient. But consumer sentiment in April fell 6.7% to its lowest level since 1952. Add in that Powell’s term expires in May 2026, with Kevin Warsh (a known proponent of lower rates) expected to be confirmed as the next Fed chair, and you’ve got uncertainty everywhere.

On inflation: it’s running around 3.58%, up from 2.4% before the Iran war. What gives? Energy. Tariffs tied to the Strait of Hormuz and the war in general have pushed broader energy prices up 12.5%, gas up 18.9%, and crude up 44.2%. All of which feed straight into CPI.

Despite all of it, markets have largely looked past the turmoil. The Iran war still dominates headlines and dictates intraday moves, but a ceasefire helped steady things even as energy prices surged. The takeaway: investors are willing to look past oil-price risk in the short term. The AI trade and strong earnings were powerful enough to drown out the geopolitical noise, at least for a month.

Software vs Hardware and “The Great Tech Bifurcation:

• Stage 1 Models & Research (~2020–2023) (proof of concept)

• Stage 2 Hardware & Infrastructure (~2023–present) (this is the rotational thesis)

• Stage 3 Applications & Software (just beginning) (where AI translates into real-world business value through software)

The AI narrative has matured. In early 2026, new LLM releases showed how easily AI tools could replace legacy software companies, and now the question investors are wrestling with is: will SaaS companies be the beneficiaries of AI, or the victims of it? The answer is yes. And no. (I didn’t say that just to sound mysterious.) Some companies will pivot, some won’t, and right now it’s too early to tell. The frame I’d use: whose products are being rewritten by AI, and whose products are being used to write the next generation of it?

For now, investors are aggressively rotating capital out of software-heavy “Stage 3” names and into the “Stage 2” hardware and infrastructure backbone. The logic is simple: hardware demand is tangible and backlogged, while software’s AI payoff is still unproven. Our focus inside the rotational stays on the hardware.

🏁 That’s a Wrap

That’s the everything-update. Be good to the team while I’m out, they’re better at this than I am anyway. As always, subscribe so these land in your inbox the second they post.

Subscribe now

Enjoy the ride,

Chris

Two straight years of monthly client newsletters was not a streak I intended on breaking once I got momentum.

Turns out, planning for your first baby and your grandpa passing away fill up most of the creative brain space you had in the past.

However, like Michael Jordan with a fax machine, I do have a comeback planned. More on that below!

In This Issue

• Chris’s Parental Leave Plan

• Quick Portfolio Rankings

• Chris’s Cool Corner

Smell Ya Later! (June 1 – September 1)

I have so many cool updates to share about what is going on at our firm and things we are working on. However, that can wait a week.

For the first time in 15 years and my entire career, I’m taking some extended time off.

For a good reason!! Baby Haigh (gender unknown) is due in 3 weeks.

What this means for you

• Nothing changes. There’s a reason we are growing such a large and capable team. Life happens and we never want the quality of our work to live and die by one person being available.

• If you are used to emailing me, simply email stephanie@iconocapital.com or team@iconocapital.com and your burning questions shall be answered (probably faster than you’re used to).

• Our advisory team is down one person for 3 months, so give Jack, Gene, and Matt a little extra grace during their time of need.

I’ll be back in mid-September with a much higher tolerance for sleep deprivation.

⚖️ YTD Winners & Losers: The Portfolio Power Rankings

📉 Index Recap & Client Portfolios

🏆 Winners

💔 Losers

🧠 Chris’s Cool Corner

📖 Laziness Does Not Exist (Devon Price)

I loved this essay written by a social psychologist suggesting that situational constraints are almost always the answer when someone is perceived as “lazy”, especially children.

When is the last time you responded to a person’s ineffective behavior with curiosity rather than judgment?

⚡ The Heatmap x MIT Electricity Price Hub

If you’ve been wondering why your RGE or ConEd bill looks the way it does, check out this new tool from Heatmap News and MIT that lets you look up residential electricity prices by state, utility, congressional district, county, or zip code. You can also track how they’ve changed over the last 1, 2, 3, 4, or 5 years.

Try it here.

💳 The Ridge Wallet Tracker

My wife loses her wallet and keys 3-5x per year. Keys were an easy fix, throw an Airtag on those things. But the wallet was harder, until I discovered Ridge makes a credit card sized tracker that works with the Apple Find My app.

Buy it here.

🪏 Stuff I’m Diggin’

📲 Follow Us

Come hang with me:

• Instagram

• LinkedIn

• Facebook

🏁 That’s a Wrap

Stay tuned for 2 more newsletters the rest of the month where I will update you on all of the amazing things we are working on for you.

If you have any questions or concerns about me being out of the office for three months, I’m here for you. Except I’m not, leave me alone.

XoXo
Chris

Let me tell you a story that will make you irrationally angry about financial services.

A client of mine left a job in February. Good job, decent 401(k), total non-event.

We do things a little differently at Iconoclastic Capital. When a client has a rollover, we don’t hand them a pamphlet and wish them luck. We get on the phone together, three-way call with the old plan administrator, and we don’t hang up until the transfer is initiated directly to our custodian. White glove, start to finish. No guessing, no “did you call them yet?”, no mystery.

And even with all of that? We still spent two weeks chasing a check that should have moved in two days.

Meanwhile, four actual human beings just flew 695,000 miles around the moon and splashed down in the Pacific Ocean in ten days.

Ten. Days.

NASA threaded a needle from a quarter million miles away and hit a patch of ocean the size of a parking lot. Your old brokerage needed a month to address an envelope.

Sit with that for a second.

What “Processing” Actually Costs You (And Why No One Talks About It)

Here’s the thing nobody explains when you’re standing at the HR offboarding meeting, nodding along while someone hands you a folder about COBRA that you will never open.

Every single day your rollover money sits in transit, it is not invested. It is doing the financial equivalent of sitting in the middle seat on a Spirit Airlines flight. Not earning. Not growing. Just existing in a miserable liminal space, waiting.

The S&P 500 has historically returned around 10% per year, which works out to roughly 0.83% per month. On a $200,000 rollover sitting idle for three weeks, you’re looking at close to $1,200 in missed market exposure. On a $500,000 account, nearly $3,000.

Not from a bad investment decision. Not from a market crash. From waiting for a check to clear.

The Technology Excuse Is the Biggest Con in Financial Services

This is where I need you to stay with me, because this is the part that should make you genuinely angry.

The same institution that needed three weeks to move your retirement savings can approve a new credit card in 60 seconds. They post charges to your account in real time at midnight on a Saturday. They flagged your debit card when you bought gas in New Jersey on your way to see your “college roommate”, which, fine, that WAS suspicious.

The technology exists. They are just not using it for this.

Some institutions have started allowing mobile deposit for rollover checks. I want you to appreciate how insane that sentence is. Their solution to the problem of “moving large sums of retirement money between institutions” is “photograph the check with your phone and hope the app accepts it.” Not a wire. Not a direct electronic transfer between two institutions that both have routing numbers. A photo. Of a check. Like it is 2009 and your grandmother sent you twenty bucks for your birthday.

SWIFT moves trillions of dollars internationally every single day. ACH transfers happen constantly. There is no real technical barrier to same-day retirement rollovers. There is institutional inertia, and there is the fact that your cash sitting idle for a few weeks is not only your problem. That float is worth something to someone.

Just not to you.

The 60-Day Rule: The Part Where This Gets Actually Scary

If you take a direct distribution from a retirement account, the IRS gives you 60 days to deposit it into a new account before it becomes taxable income. Under 59 and a half? Add a 10% early withdrawal penalty on top of that.

Sixty days sounds fine until your old custodian uses 40 of them to process the paperwork and find a stamp.

But here’s the part that really stings. When your old institution cuts that check, they don’t send you the full amount. They withhold 20% upfront for federal taxes. So on a $200,000 rollover, you get a check for $160,000. Now, if you want to roll over the full $200,000 and avoid the tax hit, you have to come out of pocket for that missing $40,000 within the 60-day window, deposit the full amount, and then wait to get the withholding back as a refund when you file.

Most people don’t have an extra $40,000 sitting around waiting to plug a gap created entirely by their old brokerage’s paperwork speed.

So what starts as a simple job transition turns into a cash flow puzzle, a tax filing headache, and potentially a five-figure bill nobody warned you about. And then Dave is calling me again, except this time it is not about hold music.

What You Can Actually Do

Push for a direct rollover, institution to institution, where the money never touches your hands. This eliminates the 60-day clock entirely and typically moves faster than an indirect rollover. Have your new custodian initiate the transfer on their end rather than waiting for the old institution to get moving. Get every date in writing. Follow up relentlessly.

If you are working with a financial advisor, this is exactly what we are here for. A good advisor has navigated this process enough times to know where to apply pressure and when to escalate from “polite follow-up call” to “increasingly impatient follow-up call.”

The bottom line is simple.

Four astronauts launched April 1st, looped within 4,070 miles of the lunar surface, and splashed down off San Diego ten days later. Nearly 695,000 miles, round trip.

Your rollover check has not arrived yet.

One of those is a technical limitation. The other is a choice. And the financial industry has been making that choice for decades, because the cost of waiting falls entirely on you, and the benefit of your money sitting idle for a few weeks falls entirely on them.

NASA figured out orbital mechanics. Your old brokerage can figure out a wire transfer. They just need a reason to try.

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Congress created “Trump Accounts” as part of the One Big Beautiful Bill Act. They’re a type of traditional IRA established for a child’s benefit. The basic idea is a long runway: money goes in during childhood, grows under specific rules, and converts to a standard IRA when the child turns 18.

Here’s what makes the next few years worth watching.

The $1,000 Head Start

For children born between 2025 and 2028, the U.S. Treasury is offering a one-time $1,000 pilot program contribution. Free money into your child’s investment account at birth. The catch is that you have to elect to receive it. It doesn’t happen automatically.

To qualify, your child needs to be born in 2025, 2026, 2027, or 2028, be a U.S. citizen with a valid Social Security Number, and not have had a prior pilot program election made on their behalf. The parent or guardian making the election needs to expect the child will be their qualifying dependent for that tax year.

One thing that stands out: expecting parents can file the election before the child is born. That appears to be intentional.

No contributions can be made before July 4, 2026, and Treasury won’t deposit the $1,000 until the account is open and confirmed. This is a process you start now to be ready when the window opens.

How the Account Works

The IRS calls the period from account opening through December 31 of the year before the child turns 18 the “growth period.” During that time, Trump Accounts work a bit differently than standard IRAs.

Investments are limited to mutual funds or ETFs that track indexes of primarily U.S. companies. That language comes directly from the IRS, and the full regulatory definition hasn’t been finalized, so the eligible investment universe may shift as guidance comes out. Annual contributions from most sources are capped at $5,000, with cost-of-living adjustments starting in 2027. Employer contributions under Section 128 are capped at $2,500 and count toward that same limit. Early withdrawals during the growth period are essentially off the table.

Once the child turns 18, standard traditional IRA rules apply, including the potential 10% early withdrawal penalty before age 59½. Exceptions exist for education expenses and first-home purchases, among others.

How to Open One

The election is made on Form 4547, either by paper or e-filing with your tax return. The IRS expects online elections to be available at trumpaccounts.gov sometime in mid-2026. After you file, Treasury will send activation instructions starting in May 2026. There’s an authentication step before the account is officially open.

What This Means for Planning

$1,000 doesn’t sound like much. But invested at birth, with consistent contributions over 18 years in a low-cost index fund, the compounding math tells a different story. These accounts are built specifically around long time horizons, which is the main thing working in their favor.

We’re watching a few things as guidance develops: how the IRS defines the eligible investment universe, how Section 128 employer contributions get used in practice, and whether the $5,000 annual limit gets revisited down the road.

The big thing is this: if your child was born in 2025, the pilot program window is already open. It’s worth acting before the 2025 tax return deadline to capture the $1,000 contribution.

Reach out if you’d like to talk through whether this fits your family’s plan.

The social awkwardness nobody’s talking about and advisors with the data hygiene of a toddler eating sand

The microwave vs. chef problem

A term I’m coining that the industry deserves

The four things we’ll never hand to a machine

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We have been using our AI meeting notetaker, IconoBot 🤖, for almost two years now. It has given us thousands of hours back previously spent on data entry that we can now give to our clients.

However, a recent trend I’m noticing is when we speak with a new client there is an increasing level of disdain for the technology if we don’t warn them properly ahead of time.

I can see it on their faces, an uncomfortable shift towards discomfort they have to contend with in real time.

It’s a strange new world we’re all trying to dance around together. The technology itself a tectonic shift, sure. But I would argue that navigating the social complexities of it being thrust into our relationships is even bigger.

Listen, I get it, the pressure to say something about AI right now is enormous. But so much of the conversation around it is, to put it politely, theater.

To put it even more politely, it’s so fucking annoying.

So I’d like to take the opposite approach of everyone else in the world and talk about fun ways we’re NOT using AI right now.

Most of what I’m seeing right now in financial services is concerning:

• Advisors sneaking onto the free version of ChatGPT on their lunch break, typing client scenarios into a consumer chatbot with the data hygiene of a toddler eating sand.

• No enterprise agreement. No compliance review. No archiving. Just vibes.

• Advisors at major firms pasting client tax situations into a tool that OpenAI is absolutely using to train its next model, and their compliance departments would have a collective stroke if they found out.

The reason we adopted AI has nothing to do with AI. We've always been borderline neurotic about being unreasonably prepared for every client interaction.

The Microwave vs. The Chef Problem

I want you to picture two kitchens.

In kitchen number one, there’s a guy reheating leftover Olive Garden in a microwave. He hits the popcorn button because he can’t be bothered to figure out the actual cook time. The plate comes out scorching on the edges and frozen in the middle. He posts on Instagram Stories: “Cooking Italian tonight 🧑🏻‍🍳 .” Technically not a lie.

In kitchen number two, there’s someone who spent years learning knife skills, who understands why you deglaze a pan, who can taste a sauce and know what’s missing. They’re using the same basic technology as the microwave guy (heat + food = dinner) but the intent, the skill, the outcome? Completely different universes.

That’s AI adoption in financial services right now. There are chefs, and there are people pressing the popcorn button.

I know advisors at big box firms who think they’re on the cutting edge because their meeting notetaker generates a summary after client calls. And they talk about it at like they just split the atom. “It even creates action items!” Yeah man, so does a legal pad.

And here’s the part that makes me want to flip a table: according to recent industry data, only about 5% of investment adviser firms are using AI for anything client-facing, while roughly 40% have adopted it for internal use. For most of those firms, “internal use” means Microsoft Copilot. That’s it. That’s the whole menu.

Not because Copilot is the best tool for the job. Because it’s the only one their compliance department will approve.

The Dirty Secret

I want to coin a term here, because I think we need one: AI Cosplay.

AI Cosplay is when a firm or person dresses up in the costume of technological sophistication without actually changing anything.

They’re either lying about AI agents making them $100,000 in a month, thus not changing their identity as a loser who lies for clicks.

Or, they’re creating efficiencies for efficiency’s sake, without any purpose toward why they need more free time.

The firms getting real value from AI aren't the ones with the biggest voices. They just asked themselves a boring question: where are we wasting time that should be going to our clients?"

That’s it. That’s the whole framework.

Every hour we used to spend on data entry, report formatting, or hunting through tax code was an hour we weren’t spending on the thing you actually pay us for. Which is judgment. Experience. The ability to look at your full financial picture and say 'here's what I'd do, and here's why.' Not just spit back the textbook answer, but know which answer actually matters for your life.

AI gave us those hours back. What we do with them is on us.

Things We Refuse to Use AI For

We don’t use AI to make financial planning recommendations.

When the market drops 15% in a week and you call us, you’re not looking for a chatbot to recite the likelihood of a recovery in 18 months. You’re looking for someone who knows that your daughter starts college in two years, that you just refinanced, and that the last time this happened you almost panic-sold your entire portfolio at the bottom.

AI can model the breakeven age on your Social Security decision. What it can’t do is sit across from you and watch your face change when we talk about what retirement actually looks like versus what you think it looks like.

It doesn’t know whether you actually like your job or you’re white-knuckling it to some finish line you set in your head ten years ago.

Claude could probably pass the CFP exam with a perfect score right now. That should tell you more about the limitations of standardized testing than it does about whether software should manage your money.

The job was never knowing the answers. It's knowing which answers matter for you.

We will never use AI to fake scale.

Some firms are using AI to manage more clients with fewer humans and calling it “efficiency.” If your big efficiency gain means a client talks to a chatbot instead of their advisor, you haven’t gotten more efficient. You’ve gotten worse.

That’s like a restaurant replacing the chef with a vending machine and bragging about their improved margins. You might be saving money, but nobody’s coming back for seconds.

We'd rather serve fewer families well than more families poorly. We use AI to go deeper with the people who trust us. Not wider.

We will never use it to write from the heart.

Yes, there are blogs I will write or social media posts I make that are mostly AI generated. As a business owner, I have a responsibility to my team and clients to use the available tools in front of me to grow our firm as best I can. Nobody benefits from us going out of business from being stubborn.

But if I’m writing something like this post, or any sort of communication that requires empathy I’m doing it the ol’ fashioned way. When we send you something that matters, a human who gives a shit wrote it.

There’s also a version of every client email that AI can draft. It’ll be clear, professional, grammatically perfect, and feel gross when you read it.

The hard part of telling a client their plan needs to change isn’t finding the right words. It’s knowing whether this person needs the blunt version or the gentle version. Whether they want to be told what to do or need to arrive at the conclusion themselves.

We will never use it to put your information at risk.

Remember those advisors I mentioned pasting client tax returns into the free version of ChatGPT? That’s not a hypothetical. It’s happening right now across the industry. The SEC considers AI-generated communications to be business records, which means firms are responsible for capturing, retaining, and supervising every interaction. Nearly half of compliance departments haven’t even set up formal testing for AI outputs yet.

We use enterprise-grade tools with proper data guardrails. Your information doesn’t train a public model. It doesn’t get stored on a server we don’t control. This shouldn’t be a differentiator. It should be table stakes. But right now, it’s not, and that’s a problem the rest of the industry needs to figure out fast.

So Where Does That Leave Us?

AI is a massive fork in the road. You can use it to cosplay innovation while cutting corners. You can resist it and fall behind. Or you can use it the way we do, which is as a tool to fuel an obsession with being great for the people who trust us.

We want to be better for you. That's it. Not faster. Not cheaper. Not more 'innovative.' Just better.

AI helps us do that, so we use it. The day it stops, we stop. Pretty simple.

Schedule a conversation with our team

Iconoclastic Capital Management LLC is a SEC Registered fee-only RIA firm. This content is provided for informational purposes only and should not be relied upon as professional advice.

Somewhere between “which stroller folds with one hand” and “do we really need a wipe warmer”, I fell down a rabbit hole on a piece of legislation that, I swear on everything I own, will hand my unborn child a thousand dollars before they’ve taken a single breath outside the womb.

A thousand bucks. For being born. In America. Between 2025 and 2028.

The One Big Beautiful Bill Act. That is the actual name. Congress passed the most significant tax overhaul since the Reagan era, named it like it was a fragrance by Donald Trump, and signed it into law on the Fourth of July because of course they did.

(I should note: I am not here to litigate the politics. I’m here because I read the whole thing, all of it, and 95% of the people who will be affected by this law have not. Including, probably, the people who voted for it.)

Here’s what you need to know. Six moves. The ones that will actually change your financial life in 2026. Think of this as the cheat sheet your accountant hasn’t built yet.

Let’s go.

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1. The SALT Cap Just Quadrupled (But There’s a Trap Door)

If you live in New York, New Jersey, or Connecticut, the SALT cap has been your nemesis since 2017. You could only deduct $10,000 of state and local taxes on your federal return. For anyone paying NYC income tax plus property taxes, you blew past that number before Valentine’s Day.

The new cap is $40,000.

Which sounds incredible until you read the fine print. And you should always read the fine print.

If your household income exceeds $500,000, the $40,000 cap starts shrinking. By $606,000, you’re back to the old $10,000 limit.

So for a dual-income professional household in Brooklyn or Westchester pulling north of $500K, the relief is real but less dramatic than the headline suggests. For households in the $200K to $500K range? This is a straightforward, meaningful tax cut. Real money.

The move for business owners: If you operate through an S-corp or LLC, the Pass-Through Entity Tax (PTET) election still lets you bypass the SALT cap entirely. Your business pays the state tax at the entity level, deducts it before the income flows to you, and the cap never touches it. Congress explicitly preserved this workaround. They could have killed it. They didn’t. Take the hint.

Wtf is PTET? Let's Talk

2. Trump Accounts: A $1,000 Gift From Uncle Sam to Your Newborn

On July 4, 2026, roughly three weeks after my kid is supposed to arrive, a brand new type of tax-advantaged savings account goes live. Every U.S. citizen born between 2025 and 2028 gets a $1,000 federal deposit. You can then contribute up to $5,000 per year. The money grows tax-free. At age 18, it converts into an IRA.

I’ll save you the political commentary. Here’s what matters: the math is stupid good.

$5,000/year from birth to age 18 at a 7% return ≈ $190,000. Tax-free growth. Then it rolls into an IRA and compounds for another 40+ years.

We’re talking about potentially setting up a million-dollar retirement account for your child before they’ve picked a college major. Before they’ve had their first job. Before they’ve ever Googled “what is a Roth IRA” at midnight like the rest of us did.

The even savvier play: employers can contribute up to $2,500 per year to an employee’s child’s Trump Account on a tax-favored basis. If you run a business, this is one of the stickiest retention benefits you can offer. You’re not just paying someone. You’re investing in their kid’s future. Good luck poaching that employee.

For our clients with newborns or kids on the way, we’ll be setting these up the day they go live. Consider the paperwork already in the queue.

3. No Tax on Overtime (Kinda)

This one sounds like a campaign bumper sticker that would never actually become law.

It did.

Starting in 2026, the premium portion of your overtime pay (the “half” in time-and-a-half) is deductible up to $12,500 for individuals or $25,000 for joint filers. If you’re a nurse pulling doubles, an engineer logging 55-hour weeks, or anyone earning FLSA-mandated overtime, this is found money.

The catch (there is always a catch): your employer has to separately report qualified overtime compensation on your W-2. If their payroll system can’t distinguish between FLSA overtime and other types of premium pay, you can’t claim the deduction.

The law is there. The infrastructure isn’t always.

If you’re an employer reading this: getting your payroll system right on this isn’t just compliance. It’s a recruiting tool. “Your overtime is worth more here” is a hell of a pitch in a tight labor market.

4. 100% Bonus Depreciation Is Permanent 🏗️

For the business owners in the room. This is the headliner.

Under the old rules, bonus depreciation was on life support. Scheduled to drop to 20% in 2026 and flatline entirely in 2027. The new law brought it back to 100% and made it permanent. Every dollar you spend on qualifying equipment or technology can be written off immediately. Not over five years. Not over seven. Now.

Let me make this tangible. Say you run a growing practice or a small firm and you need to upgrade your team’s laptops, buy new office furniture, invest in better software infrastructure, or lease a vehicle for the business. Under the old phase-out, you’d only write off 20% of those costs this year and depreciate the rest over time. Under the new rules, 100% of it hits your return in the year you buy it.

That $8,000 MacBook Pro setup for your new hire? Full write-off. The $30,000 office buildout you’ve been putting off because the timing never felt right? Done. Year one.

Savvy hack: $1 Macbook Leases. Spread the payments over 36 months, but write off the full cost immediately.

And that’s the part nobody’s talking about. The permanence changes how you think, not just how you file. You can time purchases around when your business actually needs them instead of when the tax code forces your hand. Need new equipment in March? Buy it in March. The deduction will be there whenever you’re ready.

For a small business owner doing $500K to $2M in revenue, the difference between expensing a purchase immediately and depreciating it over five years is real cash flow. It’s the difference between reinvesting in growth this quarter and waiting until next year.

5. The S-Corp Is Still The Cool Kid (For Now)

The question isn’t “S-corp or C-corp?” anymore. It’s “What are you building, and what does the exit look like?”

If your answer is “I’m running a profitable services business and I want to minimize current-year taxes,” the S-corp with QBI is still your friend. If your answer is “I’m building something I plan to sell for a multiple of revenue in three to seven years,” the C-corp with QSBS should be on your radar immediately.

The 20% QBI deduction phase-in thresholds just expanded significantly. In 2025, joint filers started losing the deduction at $394,600 of income. In 2026, that number jumps to $403,500, and the phase-in window widens from $100,000 to $150,000. Translation: more doctors, lawyers, and consultants get to keep at least a partial deduction as their income grows.

This is the kind of decision that costs people six or seven figures when they get it wrong. And most people don’t think about entity selection until it’s too late to change it cleanly.

Something interesting to note: the OBBBA just made C-corporations the most interesting entity choice for high-growth businesses in a way that hasn’t been true in decades. The reason has a name: Section 1202. Qualified Small Business Stock. QSBS.

If you start or invest in a qualifying C-corp and hold the stock long enough, you can exclude a massive chunk of your capital gains when you eventually sell. We’re talking up to the greater of $15 million or 10x your cost basis.

6. The Charitable Giving Shakeup Nobody’s Talking About

Here’s a weird one that might matter more than you think.

Starting in 2026, if you take the standard deduction, you can deduct up to $1,000 ($2,000 for couples) in cash charitable contributions above the line. That’s new. That’s good for a lot of people.

But if you itemize? There’s a new floor. Only contributions exceeding 0.5% of your AGI are deductible. So if your adjusted gross income is $400,000, your first $2,000 in charitable giving doesn’t count for tax purposes.

This creates a massive incentive for what we call “bunching”: concentrate two or three years of giving into a single year to clear the floor and maximize the deduction, then take the standard deduction in off years.

The cleanest vehicle for this? A Donor-Advised Fund (DAF). You make a large contribution to the DAF in year one, take the full deduction, and then distribute the money to your favorite charities over the next several years at your own pace. The tax benefit hits immediately. The giving happens on your schedule.

If you’re already charitably inclined and haven’t set up a DAF, 2026 is the year. This isn’t aggressive tax planning. It’s just math.

So What Does All of This Actually Mean?

Here’s where I’m supposed to tie it all together with some sweeping statement about the future of American tax policy. I’m not going to do that. Partly because nobody actually knows how this plays out over ten years. Partly because I think the more honest thing to say is this:

Most people will sleepwalk through the biggest tax overhaul of their adult lives.

They’ll hear “Trump Accounts” at a barbecue, nod, and never open one. They’ll keep filing the same way they’ve always filed because changing something feels risky even when not changing is the actual risk. They’ll leave the PTET election on the table because nobody explained it in plain English. They’ll bunch nothing. They’ll optimize nothing. And they’ll pay more in taxes than they needed to, every single year, for the rest of the decade.

That doesn’t have to be you.

I keep thinking about my kid. (I think about my kid a lot these days, which I’m told is only going to intensify.) They’ll be born into a world where their parents already have a plan for the account that launches three weeks later. Where dad’s business is structured to capture every deduction the new code offers. Where the SALT strategy and the charitable bunching and the entity election have already been modeled and optimized.

I don’t know if this kid will care about any of this stuff someday. I don’t know if they’ll be into finance or sports cards or something I can’t even imagine yet. Maybe they’ll be a poet or a carpenter or one of those people who lives in a van and is somehow happier than everyone I know. Whatever. I can’t control that.

What I can control is whether someone was paying attention to the details while they were too young to do it themselves.

That’s the job. That’s always been the job.

And right now, in 2026, with this much changing this fast? It’s never mattered more.

Iconoclastic Capital Management is an SEC-registered investment adviser. This content is for informational purposes only and does not constitute tax advice. Please consult a qualified tax professional regarding your specific situation.

Finding tax documents on financial institution websites is such a pain in the ass.

Altruist is a way better experience, but I’m still going to show you where to look!

Here’s the step-by-step, with a bonus video walkthrough. We try to get these to you first, but we know some of you are just too. antsy.

📄 What You’re Looking For

There are three forms that might show up in your Altruist account as of this post:

1099 Interest

Interest earned in your high yield cash account.

1099 Consolidated

Dividends, interest, capital gains from taxable accounts. Usually 4–10 pages depending on your activity. The cover page will say “1099 Consolidated” in big letters, you can’t miss it.

1099-R

IRA distributions, rollovers, withdrawals (more on this next week).

⚡ The 60-Second Version

Log into your Altruist Account

Head to Documents in your Altruist Client Portal or Mobile App.

Tip: set the filter to Tax Documents to see only your tax forms.

Download and send to Jordan via his sharefile or however your dusty accountant prefers you deliver it to them.

🎬 The “I Need More Detail” Version

For those of you who want to see it done before you try it yourself, I recorded a quick walkthrough in one of my own accounts.

❓ FAQ

What if I see multiple 1099s?

Altruist transitioned the trustee of record from Equity Trust Company (ETC) to themselves (Altruist) in 2025, you may receive two sets of tax documents for the same account.

1. From Equity Trust Company: Covers reportable activity from January 1 through October 31, 2025, when ETC served as trustee of record.

2. From Altruist: Covers reportable activity from November 1 through December 31, 2025 when Altruist served as the trustee of record.

What if I rolled money over in 2025?

You’ll likely receive a 1099-R from your old custodian (Fidelity, Vanguard, etc.)

We’ll explain what that means in next week’s post (spoiler: in most rollover situations, it doesn’t mean you owe taxes). For now, just know it’s coming and don’t panic when you see a big number in Box 1.

Long time no blog! Sorry, I’ll make it up to you, I promise.

Every February, the same ritual plays out:

• You email us asking “where the f&%! is my tax stuff?!”

• You ignore this blog post and email us on April 14 with URGENCY.

We’re not doing that this year (please?).

🎯 What Is the Tax War Room?

This is the 2025 Tax War Room; an Icono mini-series designed to make sure you don’t overpay, miss a deadline, or waste a single hour figuring out what your accountant actually needs from you.

All will be written like you’re a smart person who doesn’t need to be talked down to, but also doesn’t have a CPA license framed on your wall.

What we won’t do: We don’t file your taxes. That’s Jordan of Redwood Tax job.

But we will make sure you’re not leaving money on the table before handing you off to him, because you never learned how tax law works in High School. Instead you learned how to make tiramisu in Home Ec.

📅 The Schedule

🚨Important Note🚨 Do NOT file your taxes yet (Feb 3). There is a 99% chance you are missing a 1099 document and will have to amend your return.

Key: 💰 (IRS, NYS or external deadline) | 👨🏻‍💻 (Icono specific deliverable)

💰 January 31: Employer W2 documents available. Upload them to your RightCapital Vault ASAP!

💰 February 2: 1099 Interest Documents (for Altruist Cash) and 1099-R Documents (for those that took withdrawals from IRAs or Roth conversions) available on Altruist.

👨🏻‍💻 Friday Feb 6: Video Walkthrough: How to pull your 1099s from Altruist and what the different boxes mean.

👨🏻‍💻 Monday Feb 9: The One Big Beautiful Bill Act changes, NYS credits, and other landmines you didn’t know existed.

💰 Monday Feb 16: Most Altruist 1099 tax documents should be available.

👨🏻‍💻 Tuesday Mar 3: Comprehensive and Guided Wealth Management clients can expect to receive their customized tax letter by now to send to their accountant.

💰Monday Mar 16: Last batch of Altruist 1099 documents released.

💰Monday Mar 16: LLC, Partnership, and S Corporation business tax returns due.

🔺 The Tax Triangle

Think of your financial life as three corners of a triangle:

1. You: the person making decisions and living your life

2. Us: the people building and monitoring your financial plan

3. Jordan: the person making sure the IRS doesn't send you a love letter in 2027

This series is the connective tissue between those corners. It's how we make sure everyone's working from the same playbook, so you're not the middleman explaining things you shouldn't have to explain.

🤝 How the Icono-Redwood Partnership Actually Works

When you’re an Iconoclastic client, we already know about 90% of your tax situation. We know about the Roth conversion you did in October because we were the ones who suggested it.

We know about the RSUs that vested. We know about the rental property, the HSA contributions, the 529 plan, and the capital gains from that rebalance in Q3. We’ve been tracking it all year.

So when we hand things off to Jordan, we’re not just forwarding documents and hoping he figures it out. We’re passing along a full briefing: here’s what happened, here’s what to watch for, here’s what might look weird but is actually fine. Jordan gets context that most CPAs would never have, because most CPAs aren’t embedded in their clients’ financial plans the way we are.

The bonus: If you work with Jordan through our new Guided Wealth Management Service Model, you’ll receive a $275 credit towards your tax preparation. It’s our way of making the handoff as seamless as possible, and making sure cost isn’t a barrier to getting your return done right.

✅ Your Homework

1. If you're an Iconoclastic client, you should have your introduction to Jordan Stealey facilitated by now. If you haven’t, or want to, then email us (team@iconocapital.com) and CC him (Jstealey@redwoodtaxconsultants.com) to let us know!

2. Upload any and all tax related docs to your RightCapital Vault

3. If you want some help with crypto taxes and have a crypto wallet with more than $10,000 in it, sign up for Cointracker and click “Add a Tax Pro” to invite chris@iconocapital.com

Let's do this!!!

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But there’s another savvy tool that almost nobody talks about: the mortgage recast.

A mortgage recast is one of those rare personal finance strategies that checks every box: simple, cheap, and high impact.

Which usually means one thing: it doesn’t make banks much money.

What is a Mortgage Recast?

(Note: this only applies to those who have made extra payments on their mortgage)

A mortgage recast is when your lender re-calculates your monthly payment based on a lower principal balance, while keeping:

• the same interest rate

• the same loan term

• and the same final payoff date

So unlike refinancing…

• Refinance: replaces your mortgage with a new one (new rate, new term, closing costs)

• Recast: keeps your mortgage the same, but lowers the payment because you owe less

If refinancing is “rebuilding the loan,” recasting is just redoing the math.

The Case Study: A Recast in the Wild

1. The Starting Point (February 2018)

Here’s our homeowner in early 2018:

• Home Price: $500,000

• Down Payment: 10% ($50,000)

• Loan Amount: $450,000

• Interest Rate: 4.75% (Fixed 30-Year)

• Monthly Payment (P&I): ~$2,347

• Total Monthly Payment (Estimated): ~$2,722 (including taxes/insurance)

Nothing exotic. Just a normal mortgage from the “pre-2020” world.

The Strategy: Bi-Weekly Payments (the quiet cheat code)

Instead of paying $2,722 once per month, the owner pays $1,361 every two weeks.

That creates the sneaky benefit:

• 26 half-payments per year = 13 full payments

• That “extra” full payment goes straight to principal

  • Which reduces the balance faster

  • Which reduces interest faster

  • Which compounds into meaningful progress

2. The Milestone (January 2026)

By January 2026, the homeowner has been doing this for nearly 8 years.

Here’s what the math looks like:

That’s roughly $37,000 ahead of schedule.

So why recast now?

Here’s the emotional reality:

Being ahead on your mortgage is great…
…but you don’t “feel” it.

A recast is how you convert progress on paper into lower monthly payments.

3. The Comparison: The “Ah-Ha” Moment

When the bank recasts, it takes the same remaining term and the same rate, but recalculates the monthly payment based on the lower $348,000 balance.

So the homeowner goes from:

• $2,347/month → $2,120/month

• without refinancing

• without changing rates

• without resetting the clock

That’s $227/month freed up immediately.

Why this matters (beyond $227/month)

A recast is powerful because it increases your financial flexibility.

That’s the entire goal of good planning: make the math serve the life.

Lower payments give you options:

• build cash reserves faster

• invest more consistently

• handle childcare / tuition / job changes

• breathe

And if you still want to pay extra? You can.

The recast doesn’t stop you from paying more.
It just lowers your mandatory payment.

Optional Advanced Move: Infinite Money Glitch

Once you understand the recast, the next mental model is this:

What if I want to take these good habits and spin them off into another property?

That’s where “wealth loop” thinking comes in.

The 2030 Snapshot

Here’s what this looks like using the same homeowner, but now its 2030 and their house has grown in value:

• home value around $850,000

• chooses to pull $400k out (cash-out refi)

• buys a rental property

• rental income offsets or exceeds the new mortgage payment

Infinite ROI

Since you pulled equity (the bank’s money) to buy the asset, your personal cash investment is $0. This creates infinite return on investment.

Double Appreciation

You now own $1.25M in real estate ($850k home + $400k rental). Both assets go up in value while your debt stays fixed.

Tax Efficiency

The rental income is often offset by depreciation, while the interest on your primary mortgage may remain tax-deductible.

Summary: Why a Mortgage Recast is So Underrated

A recast is one of the simplest ways to improve your monthly cash flow without blowing up your mortgage.

✅ Lower Payments

Your required monthly payment drops immediately.

✅ Keep Your Rate

If you like your interest rate, you keep it.

✅ Flexibility

You can still pay extra, but your baseline obligation is lower.

✅ Low Cost

Usually a small fee (often a few hundred dollars) instead of thousands in closing costs.

Final Thought: Who Should Consider a Recast?

A mortgage recast is most useful when:

• you’ve paid down principal aggressively

• you received a windfall (bonus, inheritance, sale of asset)

• you have a good mortgage rate you don’t want to lose

• you want lower required payments without refinancing

FIND OUT FOR YOURSELF HERE!

Part 1 was the warm-up: the nostalgia, the gut laughs, the “oh my god I forgot about that” moments.

View Part 1 Here

Part 2 is the stuff that did something bigger. Not always “important” in a Nobel Prize way. More like: it quietly changed how we move, how we talk, how we work, how we trust, how we remember, and how we waste time.

Which, if you’re tracking, is basically the whole human experience.

Ground rules stay the same:

• “Best” is not “most important.”

• No tragedies. No political side taking.

• We’re grading on joy, ubiquity, shock value, and legacy.

• The two tiebreakers remain The “I Remember Where I Was When…” Factor and The Holy Shit! Factor.

Let’s finish the list.

10. Dave Chappelle (2003-2025)

You could argue Chappelle’s Show was the moment comedy became a national language. From Charlie Murphy to Rick James to Wayne Brady, everybody knew what you were quoting.

Why it matters

Chappelle didn’t just tell jokes, he shaped culture, and in turn used that ripple effect on social commentary into becoming one of the most influential thought leaders challenging conventions today. A true iconoclast if you ask me.

9. MySpace (2003)

MySpace was the last major social platform that felt like it belonged to its users rather than its shareholders. It was messy and customizable and deeply personal.

Why it mattered

MySpace taught a whole generation how to build an identity online. It was the internet before it got sanitized and optimized. You could actually customize something. You could be weird. You could be cringe. You could be you. And then we traded all of that for platforms that look identical and make everyone anxious.

8. 2012–2014

Every generation has a small window where the world feels briefly calibrated to human life. For millennials, 2012–2014 is that window. Streaming was exploding, phones were useful without being fully parasitic, social media still felt social, and culture still had a monoculture. We were all watching the same shows, hearing the same songs, sending the same memes. The internet was huge, but it didn’t yet feel like gravity.

Why it mattered

This era matters because it was the last moment when digital life mostly felt additive.

7. The 2008 Summer Olympics

#2 on our list in the “I Remember Where I Was When…” Ranking… when Michael Phelps and Team USA achieved the impossible against France in the 4x100 relay and has since been considered one of the greatest comebacks in sports history.

Why it matters

It was peak “global shared experience”. Sports still had the ability to stop time. Now everything is fragmented, and attention is basically a controlled substance in 30 second hits.

6. Artificial Intelligence (2022)

AI arrived like most “overnight revolutions” do: slowly, then all at once. One year it was a novelty that wrote awkward poems and blatantly made shit up. The next year it was inside everything, doing real work, reshaping workflows, and making people argue about the definition of creativity with the confidence of someone who has never created anything.

Why it matters

AI is not just a tool. It’s a new baseline. It changes what it means to be fast, what it means to be competent, what it means to be original, and what it means to be employed. And unlike most technological shifts, it did this without needing a new device. It just needed words.

The only reason I don’t rank it higher is because of how much of its future in our lives still scares the hell out of me.

5. Josh Allen Drafted by Buffalo (2018)

I truly hope nobody else gets to experience life of a Buffalo Bills fan born in 1991. My first vivid memory of this team was losing from the Music City Miracle, followed by 20 straight years of kicks to the stomach.

Why it matters

Allen changed the trajectory of a franchise, a city’s mood, and a whole generation of Bills fans who were raised on spiritual punishment. Not every “best thing” needs to be universal. Some of them are just pure joy for the right people.

Most Importantly, he’s an amazing person! In a region desperate to find someone to just stick all of their desperate undying love to, you can’t find an athlete who has handled it with more grace. To all the Gen Z out there that don’t understand-he healed our generational trauma.

4. The Bin Laden Situation Room Photo (2011)

A single image that instantly became history. You don’t even need context to feel it: tension, gravity, consequence, the adults in the room trying to hold the world steady.

Why it mattered

This photo is the definition of ubiquity. It became a cultural landmark and marks the last time 300+ million people in this country have all felt united.

3. Uber + Airbnb (2008–2010)

Fun Fact: The founders of Airbnb funded their company by selling Obama-and-McCain-themed cereal boxes during the 2008 election.1

Why it matters

They rewired the physical world. Cities changed. Travel changed. Hospitality changed. Transportation changed. And maybe most importantly, our expectations changed.

The modern person now expects to press a button and have reality arrive in five minutes. That’s a radical psychological shift, even if it feels normal now.

2. Google Maps (2005)

My first job was in a pizzeria from age 15-20. I occasionally went on a few deliveries if it was needed and would often have to reference a gigantic physical map of Batavia, NY to find the street I was looking for.

Can any parents of high schoolers imagine doing that now? Actually, can the parent do it either??

Why it matters

This is one of the most universally life-altering inventions of the century. It changed how we travel, how we meet, how we plan, how we deliver, how we explore, how we choose restaurants, and how we decide where to live.

It didn’t just map roads. It mapped our behavior. And the funniest part is we now treat it like oxygen, you only notice its true power when it’s gone.

1. Cryptocurrency (2008)

C’mon now, you should’ve known. It’s almost so iconoclastic it hurts!

Crypto is equal parts technology, money, ideology, and internet culture. It created a parallel financial universe and introduced digital scarcity to normal people and the previously unbanked.

Why it matters

Crypto didn’t just invent a thing. It challenged the rules of what money is, how ownership works, and who gets to participate.

Even if you hate it, you can’t ignore the impact. The “holy shit” factor remains undefeated.

Closing thoughts

If this list made you laugh, roll your eyes, or feel personally attacked: forward it to one friend and tell them to give us a follow.

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Apologies for the radio silence the last two months, a lot of good stuff has kept me away from writing, but I’ll make it up to y’all with a 4 part Newsletter over the next few days:

1. Part 1: #25 - #11 Best Things of the Quarter Century

2. Part 2: #10 - #1 Best Things of the Quarter Century

3. Part 3: 2025 Wrapped Client Newsletter

4. Part 4: 2026 Looking Ahead Client Newsletter

Introducing the list

I get so many year end recap emails come December 31, but I find them all to be the same tired takes. So I thought I would try something different.

As we bid farewell to the first quarter of the 21st century, there’s no time better than now to celebrate the people, moments, inventions, art and other nouns that made this era truly chaotic and beautiful.

A few ground rules before we jump in:

• “Best” does not necessarily mean “most important”.

• This is purely joy, silliness and the good stuff of life. No tragedies, political events or anything else we get bombarded with the other 9130 days of 2001-20251

• The “I Remember Where I Was When …” Factor2 and The Holy Shit! Factor3 are used for tiebreakers.

• Technically this is for 2001-2025, so the first winner or Who Wants to Be a Millionaire? and Survivor just missed the cut.

Lastly, keep in mind that if I omitted something, I probably didn’t do it on purpose. I came up with this list while driving for 4 hours this morning.

Let’s get to it!

25. MTV Summer Lineup (2003-2004)

Every millennial remembers where they were when CT carried Johnny Bananas like a backpack in The Challenge, but long before that was two straight summers of the most epic TV ever made:

• Real World (San Diego and Philly) & Road Rules

• Debut seasons of Punk’d, Newlyweds (with Jessica Simpson and Nick Lachey), Viva La Bam and Laguna Beach

• Cribs, The Osbournes, and Jackass

Why it matters

This was the absolute peak of reality tv. It has gone tragically downhill since Bravo unseated MTV as the purveyor of the finest slop this country has to offer.

24. Songs About Jane (2002)

Maroon 5 is arguably one of the worst bands of the last 20 years, but have you listened to their debut album recently? Its so. fucking. good.

Why it Matters

You could argue that Songs About Jane helped launch the 2000s wave of pop‑rock..

23. The Chipotle Burrito / Rise of Fast Casual (early to mid 2000s)

The meal that taught America it could spend $13 and still feel responsible.

Chipotle technically opened in 1993, but the early 2000s were when its model went mainstream. The assembly‑line burrito joint made “fast casual” part of the vocabulary.

Why it Matters

Chipotle’s success proved that diners would pay a premium for perceived freshness and customization. The fast‑casual boom forced an increase of quality across the board, until the slowly started making it worse again.

22. Vine (2012)

Six Seconds. The format birthed an entire generation of creators who learned timing and editing on the fly. When Vine shut down in 2017, it left behind a meme graveyard in my heart that is still painful to discuss today.

Why it Matters

Many of today’s internet stars cut their teeth on Vine before graduating to YouTube or TikTok.

21. TIE: Texas vs. USC (Rose Bowl 2006) and Boise State vs. OU (2007 Fiesta Bowl)

I don’t even need to describe these games. They are the first things that popped into my mind when I thought of most iconic sports moments and I could barely think of anything bigger.

20. Tiger Woods at the Masters (2008 and 2019)

Love him or hate him, Tiger Woods is the greatest athlete since… probably ever.

Why it mattered

Sports are the purest art form there is. Tiger’s unbelievable win in 2008 on 1 ACL followed by all of the personal drama ended his career a dozen times. Then to come back to win it all again in 2019… sports, man.

19. Interstellar (2014)

Christopher Nolan, Hans Zimmers, McConaughey… alright alright alright.

Why it mattered

Interstellar sparked renewed interest in relativity, black holes and Matthew Mcconaughey’s career. It also is my favorite movie of all time.

Also Considered

No Country for Old Men, There Will Be Blood, The Dark Knight

18. Landon Donovan’s Goal vs. Algeria (2010)

In stoppage time of a must‑win World Cup group game, the U.S. men’s national team looked doomed to be sent home without making it out of the group stage. Then Landon Donovan pounced on a rebound, slid the ball home and ripped off toward the corner flag as an entire country lost its mind.

Why it matters

Soccer has yet to have its moment in the American sun, but I believe this was the turning point that helped the explosive growth the sport has seen nationally over the last 15 years.

17. Best TV of the era

A list within a list! Here are the undisputed 5 best episodes or seasons of TV from 2001-2025:

• Season 1 of Band of Brothers (2001)

• “Made in America”, The Sopranos Finale (2007)

• Mad Men’s “The Suitcase” (2010)

• “The Rains of Castamere” aka the Red Wedding episode in Game of Thrones S3E9 (2013)

• True Detective’s debut season (2014) - spoiler alert, this is not the last McConaughey related item in my rankings.

16. Podcasts (2003)

On October 3 2014, Serial debuted and quickly became appointment listening. Suddenly everyone had opinions about cell tower pings and pay phones.

Why it mattered

Podcasting democratized broadcasting. Today it feels like everyone either hosts a podcast or that podcasting equipment needs to be purchased with a background check.

15. Pokémon Go (2016)

Crowds gathered at parks, strangers helped each other find rare spawns, and for a brief moment, it proved that nerds were still willing to go outside if you made “outside” a game.

Why it mattered

Arguably the last time the world felt unified. All it took was a shared scavenger hunt.

14. CarPlay (2014)

I delivered pizza in 2008-2009 and had to reference a giant town map before going out on my orders. If I could have seen into the future to how navigation looks today I would have never believed you.

Why it mattered

I love technology that you don’t notice until you are without it and then it feels like you’re driving a rental car made by Henry Ford himself.

13. The Jeter Flip (2001)

During Game 3 of the 2001 ALDS, Yankees shortstop Derek Jeter sprinted across the infield, grabbed an errant relay throw and flipped it backhanded to catcher Jorge Posada, who tagged out Oakland’s Jeremy Giambi at the plate. It literally defied physics and baseball.

Why it mattered

Like Sully landing the plane in the Hudson, you could give every baseball player 100 tries and they’d never pull this off. It’s the moment that most clearly define Jeter’s aura.

12. Philip Seymour Hoffman as Sandy Lyle in Along Came Polly (2004)

Fairport, NY native Phillip Seymour Hoffman’s is a master class in scene‑stealing. Think of Capote, Almost Famous, The Talented Mr. Ripley, Punch-Drunk Love… my god he was a tour de force.

Why it matters

Arguably one of the all-time greatest actors gave us one of the most random and funniest performances of all time before he left this earth way too young.

11. Zero‑Commission Trading (2013ish)

I had to finish with something finance related. When obinhood launched in 2013 and rolled out its app in 2014, they did something unthinkable— offered stock trading for no cost.

Why it mattered

Commission‑free platforms democratized investing and ushered in a new wave of retail traders – and, with them, many ripple effects. They lowered barriers to entry but also gamified the market, encouraging impulse trades and exposing millions to volatility.

Honorable mentions

Massachusetts legalizing same-sex marriage (May 17 2004) – It’s strange to list civil rights as a footnote, but like I mentioned - no laws or politics.

Besides, it seemed wrong to debate whether human rights should place higher or lower than a burrito. MA bravely planted a flag that set off the domino effect that culminated in federal legalization 11 long years later.

mRNA vaccines (2020) – The rare modern miracle that saved us from months or years more of lockdowns. Regardless of your stance on vaccines (sigh) you can’t help but respect those who pulled this off.

Closing thoughts

What matters to me is recognizing how these events and inventions shaped our shared experience, but more importantly, opening up discussion about how I’m right and you can’t prove otherwise.

Happy New Year!

Thanks so much Kathy Hochul, that’ll really lighten the fuckin’ load.

Because you already know we do things differently around here than other personal finance blogs, here are some truly unhinged ways to make it rain with your refund check.

1. A Cameo from Chad Michael Murray — $400

You could buy groceries, or you could pay a former teen heartthrob to mispronounce your name while recording from the driver’s seat of a Toyota Highlander.

The real reason this is #1 aside from being the most expensive? The Rizzler only charges $350 for his.

2. A Swarovski Good Luck Troll — $240

This almost didn’t make the list because it’s on sale from $300. According to Swarovski, “Display this troll anywhere in your home to celebrate individuality and optimism.”

If I bought this the only thing I would be optimistic about are my odds of sleeping on the couch that night.

3. The Hermès “Wouf” Flying Disc — $265

I can appreciate Hermes’s branding genius here. Renaming a frisbee to “flying disc” and then upcharging $250*. Don’t hate the player, hate the game.

Also, I understand the irony of posting this while owning a French Bulldog. He routinely costs us $265 and that comes with ruining half of our day at the vet because his teeth smell like death.

*Do frisbees even cost $15? Am I having one of those carton-of-milk-cost out of touch moments?

4. The Issey Miyake iPhone Pocket — $230

I’m shocked that Apple hasn’t co branded a product with GOOP or BLOOSH yet.

owns every Apple product ever made and if he ever buys this one I promise I will post it to the next newsletter posthaste.

5. The Echo Flask Hydrogen Water Bottle — $299

“Turns ordinary water into something extraordinary”

Tech bros can’t be stopped, they figured out how to scam water now too. This seems like something I would buy to improve my energy and continue to drink 2 coffees after 3pm, wondering why this stupid thing doesn’t work.

Subscribe for our Upcoming Holiday Shopping Guide!

Our next newsletter is dropping soon and will be jam packed with the most interesting items we’ve come across in 2025, just in time for you to take home this year’s White Elephant crown.

Subscribe now

Time and time again we’re all left holding a steaming bag of shit trying to decide between throwing it in our neighbors yard or stomping on it in our own.

Not to get all victory lap-y on you, but I absolutely nailed this prediction back in January.

Good news though, the cracks are forming, but they haven’t fixed jack shit! The government is on Day 41 of a shutdown and nearing a deal to push the vote on healthcare subsidies into December.

What subsidies am I referring to and what does all this mean for you? Let me break it down a bit for those (understandably) not paying attention to this circus.

Q: “I keep hearing something about health insurance subsidies ending next year. What’s going on?”

A: This is one of those government things that was supposed to be temporary but has lasted long enough for everyone to forget it was temporary.

During COVID, the government beefed up financial help for people buying their own health insurance, making it a lot cheaper for millions of families. Those savings (called “subsidies”) were extended a few times but are scheduled to end after 2025 unless Congress renews them.

If they don’t, the price people actually pay for insurance could skyrocket starting January 2026.

What’s changing in plain English

When you buy health insurance through Healthcare.gov or the New York State Marketplace, the government looks at your income and says, “We’ll cover part of the cost so you can actually afford it.”

Right now, that help is generous, even middle-income households get it.
But starting January 1, 2026, the rules flip back to the old system:

• If your household income goes above about $62,600 for one person or $84,600 for a couple, you lose that help entirely.

• Everyone else will see smaller discounts too.

So you could make one extra dollar next year and owe thousands more in premiums. That’s why we call it the “subsidy cliff.”

Why your premium will “spike” even if your plan doesn’t change

Insurance companies aren’t suddenly charging triple… what’s really happening is that the discount disappears.

Right now, the government is quietly paying part of your monthly premium behind the scenes. When that help ends, your bill jumps to the full price. It’ll feel like the plan exploded overnight, but the reality is simpler: the assistance vanished.

Who’s most likely to feel it

• Early retirees who aren’t on Medicare yet

• Self-employed professionals or small-business owners

• Anyone buying their own plan instead of getting insurance through work

If that sounds like you, you’ll be right in the blast radius of the 2026 changes.

What this means for people with employer coverage

Even if you get health insurance through your job, this shift can still hit indirectly.

When marketplace coverage becomes more expensive, fewer healthy people stay in that pool.

That can raise everyone’s base rates, including employer plans. And more people will decide to join their company plan, pushing up costs there too.

So, it’s not just about “the marketplace.” It’s a ripple that spreads through the whole system.

Take Rochester Regional Healthcare for example. Open Enrollment started last week and were hit with ‘demoralizing’ health insurance premiums upon renewing their plans.

So What Can Ya Do?

A couple ways we are helping people navigate this:

1. If you have insurance through work and you’re single, there’s not much you can do.

2. If you have insurance through work and you have a spouse, run the numbers on doing two individual plans, 1 family plan & 1 single plan, 1 couples plan on one employer vs. another… etc. Just don’t blindly renew right now based on 2025.

3. If you pay out of pocket for insurance right now as a pre-65 retiree, self-employed person, or for any other reasons— there are ways we can plan ahead by making your 2025 income looking favorable. Reach out to team@iconocapital.com and we’ll build a gameplan!

Wrapping Up

All in all, this sucks. You’re not supposed to be keeping track of government subsidies that are artificially making your insurance cheaper.

We’re all to busy trying to navigate every other corner of life, but time and time again we’re all left holding a steaming bag of shit trying to decide between throwing it in our neighbors yard or stomping on it in our own.

I assumed the government shutdown got me out of writing the newsletter this month, but it turns out I’m expected to keep delivering. Just like your local postman, you can always rely on me (sometimes, and probably behind schedule).

In This Issue

Calendar + firm updates (SEC Reg ✅, RightCapital, Open Enrollment, Crypto 201)

Chris’s Cool Corner (iPods are back?!)

Feature Story: Brilliant Land Scam and how to keep an eye out

Month in the Life Preview (what I actually did with my money)

Portfolio Power Rankings

Client Calendar + Firm Updates

🏛 SEC Registration

Last month we officially slipped into our adult diapers as we are now directly registered as a firm with the SEC instead of New York State. Once a firm passes a certain revenue and asset management threshold they are required to upgrade registration.

I’m coming up on my 14th year of my career in financial services, which started when I was 20 as a senior in college.

For that entire time I have felt like I was chasing after some level of success I could never quite grasp.

This new registration status is one of many things in 2025 that has allowed me, for the first time in 14 years, to feel a truly prideful sense of accomplishment.

As someone with severe ADHD the goalposts always seem to move in a direction that says “you’re not good enough”. That is a heavy burden to carry, and I’m sure some of you may deal with it too.

All I can say is that without the help of , , Stephanie, and I would have never been able to get to this point. They don’t get enough credit and I wouldn’t want to share this journey with anybody else.

🔄 RightCapital Transition (Goodbye eMoney?)

When it comes to our financial planning software, our clients fall into 3 camps:

1. “I don’t care what we use, as long as it makes sense and is easy to navigate.”

2. “What is eMoney? I thought we used Altruist?”

3. “You will only be able to pry eMoney out of my cold, dead fingers.”

So for the first two, we’re moving your planning hub to RightCapital. Why you’ll like it better:

More intuitive interface

Easy to use mobile app

Customizable client dashboard to track plan progress

Task management to keep everything (and everyone) on track

Sign up for Right Capital HERE

After signing up, you can update your information and connect your accounts (banking, investments, loans, etc.). If you have accounts through Altruist, we will link those for you.

📒Open Enrollment Game Plan

The University of Rochester released information about their 2026 Health Insurance plans for employees this week. The cost for PPO plans are increasing a modest 5-7% while the High Deductible/HSA plan is increasing a whopping 75% in cost.

Why do I bring this up? Every fall, your employer drops a benefits booklet thicker than a J.R.R. Tolkien novel with no guidance beyond “good luck”. By the time you reach the back section (where the actual money stuff lives), you’re emotionally unavailable for anything beyond “Sure, keep my same plan.”

Upload your benefits booklet to your RightCapital Vault, and we’ll sort through it for you. We’ll help make sure each choice fits cleanly within your financial plan, so your open enrollment decisions actually move you forward, instead of just off your desk.

Login to RightCaptial

Fun Fact: UofR employs the most Icono Capital clients (13) and the 7th most employees in all of New York State (32,000).

₿ Crypto 201 (Feat. Matthew Snider of Digital Wealth Partners)

Next week I am interviewing Matthew Snider, who owns a firm that invests 100% in private crypto funds and is one of the smartest people in the space I’ve met.

He is going to give ya’ll his insider tips and tricks to dip your foot into the world of cryptocurrency while not going overboard.

🧠 Chris’s Cool Corner

PCGS Grading Results Are In

A few months ago I shared some details on old coins my dad showed me that I decided to send to PCGS for grading/authentication. Here are the results and what they mean in case you have valuable coins of your own!

🪏 Stuff I’m Diggin’

1. 📲 Best iOS 26 Features = custom snooze times, live call screening and battery charge estimates are just a few of many new features Apple dropped in one of its best iOS updates in recent memory.

2. ⏱️ The Comeback: iPods + Watches
   With the new school cell phone bans, Gen Alpha-Z are buying iPods and analog watches on eBay to get through the school day the old fashioned way, by texting their girlfriend on a t9 flip-phone burner.

3. This year’s fall TV & Movie lineup has been incredible. Some of my favorites

   TV

   1. Black Rabbit (Netflix)

   2. Slow Horses Season 5 (AppleTV)

   3. Chad Powers (Hulu) - very dumb but unexpectedly hilarious.

   4. Task (HBO)

   MOVIES

   1. One Battle After Another

   2. Roofman - where did this even come from? It was so. good.

Land Scammers

A close friend of ours owns a piece of land in Victor, NY, which he purchased back in 2019 with plans to eventually build his dream home.

So imagine his surprise when he learned his land was listed for sale… by someone who didn’t own it.

The only reason he caught it was because the Town of Victor sent him a letter about an upcoming planning meeting to discuss the sale of his property. If that letter hadn’t arrived, the scammers might’ve walked off with hundreds of thousands in cash from an unsuspecting buyer.

Here’s how these scams typically play out

Criminals target vacant or unmonitored parcels, especially land owned outright with no mortgage. They impersonate the owner using fake IDs, doctored deeds, or forged notary seals.

Then they list the property for sale (often below market value) to attract quick, all-cash buyers. Once the “sale” closes, they vanish before anyone realizes the deed transfer was fraudulent.

In our friend’s case, the new buyers had already spent nearly $10,000 on inspections and surveys before the scam unraveled.

If you own land you don’t visit regularly, here’s how to protect it:

1. Register for County Alerts
Many county clerks offer free “property fraud alerts.” You’ll get an email or text if any new document, like a deed or mortgage is filed under your name.

2. Use a Title Monitoring or Freeze Service
Some jurisdictions allow you to “lock” your title records, meaning no changes can be filed without extra verification. If yours doesn’t, companies like Home Title Lock or your title insurance provider may offer monitoring options.

3. Mark It Clearly with “Not for Sale” or “No Trespassing” Signs
Scammers rely on buyers and agents never meeting the real owner. If your property looks abandoned or unclaimed, it becomes an easy mark.

The weird financial stuff I did this month

Every month, I’m writing down every odd little financial decision I make. What worked, what didn’t, and what I’d never admit to on CNBC.

Like selling a childhood Pokemon card on eBay for $500 and reinvesting the proceeds into Solana (crypto), then staking that Solana on a platform called Sanctum, in hopes of earning a stable yield of 9-10% APY.

Consider it a peek behind the curtain of a financial planner’s brain—equal parts disciplined and deeply unhinged.

The Good Stuff

Icono Core Value #5

⚖️ September Winners & Losers: The Portfolio Power Rankings

If the September market were a person, you would be nervous to invite them to meet your close friends. On the outside they seem like a great time, but something feels…. iffy.

If you’re often curious how we navigate making portfolio decisions for almost $100 Million of client assets, will be publishing a “State of the Portfolio” for all clients towards the end of this year.

Above you can see how Jack is more or less put on trial every month for 2 hours during his team portfolio review, where we get to Monday Morning Quarterback every decision he made with the luxury of hindsight.

📉 Index Recap:

• (September + 4.01%)

• (September + 0.81%)

Client Portfolios:

🏆 Winners:

• (September +24.56%)

• (September +15.89%)

💔 Losers:

• (September - 9.55%)

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🏁 That’s a Wrap

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In classic icono fashion, lets flip that script and find $300 (or more) with moves so easy it’s embarrassing. Call it the lazy person’s financial-aid package.

(All of these can be utilized if you’re not in the “back to school” mode of life - it is just a good hook for social media).

1) Bank Bonuses: Chase or Citi (Pick One)

Bank bonuses are the biggest layup in personal finance. The model is always the same:

• A bank wants new customers.

• They offer a cash bonus ($200–$500) if you open an account and move your paycheck there.

• You meet the requirements, wait 60–90 days, and the bonus lands in your account.

Right now, the best sign-up deals are:

• 🔗Chase Total Checking® — $300 bonus after depositing $500 within 90 days

• 🔗Citi Regular Checking — $325 bonus after $3000 direct deposits in 90 days.

For those of you still banking with KeyBank, M&T, or Wells Fargo (of which there are many) this is your escape hatch.

Switch, grab your $300–$325, and move on. You can even rinse and repeat every few years when new offers pop up.

2) Student Discounts: Spotify, Adobe, Prime

Companies know students are broke, so they give away ridiculous discounts hoping for loyalty later. The only catch? You need a .edu email or to pass a quick student verification check.

• 🔗Spotify + Hulu Student $5.99/month for both, saves $191.88/year

• 🔗Adobe Creative Cloud (For Students AND Teachers!): saves ~$480 in year one

• 🔗Amazon Prime Student six months free, then half-price with 5% back on Amazon purchases

And here’s the wink: if you’re not a student anymore, borrow the college email from someone in your life. It’s not fraud, it’s efficiency.

These discounts function like permanent coupon codes as long as the student status checks out. Stack two or three together and you’re saving $600+ annually without breaking a sweat.

3) Card-Linked “Gimme” Credits

These were the original inspiration for this post, which in overall theme is to find savings in areas you are already spending.

These are in my specific account portals and should show up in yours too if you have one of these cards.

Chase Freedom/Sapphire

AMEX

4) Capital One × DoorDash (Stack It for 20×)

Capital One’s Offers portal is showing up to 16× miles on DoorDash, but the fine print means you can actually stack it up to 20X!

• Order #1 (New + Non-Restaurant): You trigger the 16× “first non-restaurant” bonus and the 4× “new customer non-restaurant” bonus. That’s 20× total. Think groceries, convenience store, or CVS order.

• Order #2 (First Restaurant Order): Now you’re no longer “new,” but you still get 16× miles on your first restaurant run.

• After that: The 4× “new customer” multipliers fall off.

Translation: front-load your first order with something non-restaurant, then hit your first food delivery second. That’s a 20× + 16× one-two punch, have mercy.

5) Midnight Crypto Airdrop — Free $100

An airdrop is when a crypto project just… hands you money. It’s like if Nike randomly showed up and said, “Congrats on owning sneakers last year, here’s a $100 gift card.”

The deal

• If you held $100+ in ADA, BTC, ETH, SOL, or other eligible tokens in July 2024, you qualify for the 🔗 Midnight Airdrop

• Current value: about $100.

• Important: you must have held the coins in your own wallet (keys you control). No exchanges, no ETFs, no Robinhood.

Bonus Round: Shopping Referral Codes

These require you to spend on something you already aren’t, so don’t buy shit just to feel somethin’, but if you were planning to purchase one of these soon then that’s what we call a happy accident.

🔗 Rakuten: Join via that referral link by Sept. 30 and spend at least $50 at eligible retailers within 90 days. You can then start referring your friends and family to earn more $50 bonuses.

🔗ClassPass: Free trial + 20 bonus credits if you sign up through a friend’s referral. That’s basically a few spin classes or yoga sessions on the house.

Quick Disclosures 🧾

• Bank bonuses and merchant credits can be taxable (often as interest or miscellaneous income). Keep an eye out for 1099s and report accordingly.

• Offers change. Dates and amounts above are current as of September 11, 2025; always confirm terms on the official pages before you pull the trigger.

• Sometimes the links we use give us referral rewards. We pool those rewards and donate to a Rochester charity every year.