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In the market update, we covered the macro — nine straight up weeks, record highs across the board, AI leadership intact, oil easing, yields finally giving the market some relief.

This one is different. This is how the two of us — TonyR and TonyB — are actually thinking about the portfolios right now. Two perspectives on the same tape. Where they converge tells you the high-conviction read. Where they diverge tells you the texture worth paying attention to.

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Nine straight weekly gains for the S&P — the longest streak since 2023. The Dow closed above 51,000 and all three majors sit at fresh record highs. Dell blew the doors off on AI server demand, reinforcing that the market will still pay up for anything AI. The two macro pressures that nagged the tape all spring both eased this week: oil fell hard (Brent ~$92, WTI ~$87) on U.S.-Iran de-escalation hopes, and the 10-year yield drifted back to ~4.44%. Volatility is, in TonyB’s words, “dead.” Flows are chasing performance back into stocks. The recipe is bullish — and that is exactly when discipline matters most.

Part I: The Week at a Glance

The S&P 500 added roughly 1.4% on the week, marking its ninth consecutive weekly advance — the longest winning streak since 2023. The Nasdaq tacked on 2.4% and the Dow closed above 51,000, both at fresh record highs. The Russell 2000 continued its quiet outperformance.

What changed this week is that the market got help from the two places it had been fighting all spring: rates and oil both moved in the bulls’ favor. Treasury yields drifted lower (10-year back to ~4.44% from the mid-4.50s), and crude sold off sharply on optimism around a U.S.-Iran ceasefire extension. Lower yields plus lower oil is a direct tailwind for equities — it eases the discount-rate pressure on high-multiple tech and relieves the near-term inflation worry at the same time.

Dell was the marquee earnings event: the stock exploded higher after a strong report, raised guidance, and big AI-server demand commentary. The message to the market was unambiguous — the AI infrastructure build is still accelerating, and capital will keep paying up for exposure to it.

Part II: Five Themes That Defined the Week

Theme 1: The Streak Hits Nine — and the Math Starts to Matter

Nine consecutive up weeks is genuinely rare. The further a streak extends, the more the forward risk/reward skews away from “chase it.” That doesn’t mean a top is in — momentum this strong rarely ends on the first down day — but it does mean the expected value of aggressive new longs is worse here than it was eight weeks ago.

Context that matters: streaks like this historically resolve more often into sideways digestion or a modest pullback than into continued vertical gains. The base rate favors patience.

Actionable:

• Traders: this is a premium-seller’s tape, not a chase-the-breakout tape. Favor theta-positive structures and defined risk over naked directional longs.

• Investors: don’t add maximum equity exposure at a 9-week extreme. If you’ve been waiting to rebalance, extension is your cue — not because the rally is over, but because the asymmetry has shifted.

Theme 2: AI Is Still the Engine — Dell Proves It

Dell’s blowout and guidance raise was the week’s clearest signal that the AI infrastructure cycle isn’t slowing. Capital keeps flowing to semis, servers, and infrastructure names.

Context: the risk in any dominant theme isn’t that the story is wrong — it’s that positioning gets crowded and expectations get stretched, so even good news eventually produces muted reactions. We’re not there yet this week (Dell ripped), but it’s the thing to watch.

Actionable:

• Traders: AI remains the momentum trade, but be selective. On the most extended single names, slightly-OTM call spreads (14–30 DTE) are a lower-cost way to express upside than chasing shares. Avoid buying breakouts on emotion — wait for pullbacks to moving-average support.

• Investors: separate the true AI winners (real revenue, real demand) from names simply riding the hype. Trim where a position has become an outsized chunk of the portfolio; concentration risk is the silent killer in a crowded theme.

Theme 3: Oil Drops — Inflation Pressure Eases

Crude fell sharply (Brent ~$92, WTI ~$87) as markets leaned into optimism around a U.S.-Iran ceasefire extension. Falling oil is a double tailwind: it eases headline inflation pressure and it lowers an input cost for consumers and most of the economy.

Context: energy has been a headline-driven, two-way product all spring. A de-escalation that sticks keeps a lid on inflation expectations and gives the Fed more room; a breakdown in talks would reverse that quickly.

Actionable:

• Traders: energy remains a headline product — size accordingly. Sharp down-moves in the energy complex on de-escalation headlines have repeatedly been short-term mean-reversion setups, not the start of trends. Don’t marry the direction.

• Investors: lower oil is supportive for margins, consumer spending, and risk assets broadly. It’s a quiet positive you don’t need to trade — just understand it’s part of why stocks are getting permission to grind higher.

Theme 4: Yields Finally Blink — the 10-Year Back to ~4.44%

The single most important supportive development this week. After spending the spring backing up toward multi-decade highs, the 10-year eased to around 4.44%, and the long end drifted with it. Lower yields directly support growth and high-multiple names through the discount-rate channel.

Context — and this is the key tension TonyB keeps flagging: the question is whether this is real rate relief or a temporary pause. If yields resume climbing, the rally gets fragile fast, because almost everything else (AI, momentum, earnings) is already a tailwind — the one variable that can flip the tape is the discount rate.

Actionable:

• Traders: watch the 10-year (and /ZB) more than the VIX. The VIX is reactive; yields are leading. A 10-year break back above ~4.65–4.75% would be the first real warning that the rally’s character is changing. Below ~4.30% and the melt-up likely extends.

• Investors: this is the macro variable to monitor in your weekly check-in. Rate relief is the permission slip for the current rally; if it’s withdrawn, high-multiple exposure is where the pain shows up first.

Theme 5: Volatility Is “Dead” — Which Makes Protection Cheap

/VX never mounted a meaningful rally all week despite multiple chances; every flicker of fear was sold. VIX stayed compressed in the mid-teens. That’s a trend-following, low-vol regime — comfortable, but the calm itself is the setup.

Context: compressed volatility is not a reason to be complacent; it’s the reason protection is cheap. The best time to buy insurance is when nobody wants it — after a 9-week run, not after a decline.

Actionable:

• Traders: premium-selling environments thrive in this regime — but don’t size up assuming you’ll collect crash-day credits. And use the cheap vol to buy convexity: OTM put spreads on the index are inexpensive here.

• Investors: this is the textbook moment to add modest tail protection while it’s on sale. A small, continuous allocation to downside hedges (financed by the income side of a portfolio) is cheap insurance against the drawdown everyone keeps anticipating.

Part III: Cross-Asset Status Check

Treasury Bonds (TLT −1.46% YTD). Bonds finally caught a bid this week as yields eased — a relief, but TLT is still negative on the year. The structural pressures (fiscal supply, sticky inflation, a Fed on hold) haven’t vanished; they just took a week off. Watch whether the bid holds through next week’s jobs data.

Gold (GLD +4.73% YTD). Quiet, persistent strength. Gold continues to behave like a structural hedge against the whole macro framework — central-bank buying, deficits, geopolitical premium — rather than a tactical inflation trade. A 5–10% allocation continues to make sense for most long-term investors.

Small caps & breadth (IWM +16.74% YTD). The Russell’s leadership is the healthiest part of this rally — broad participation, not just five mega-caps. For investors overweight the S&P, adding small-cap and international exposure is reasonable rebalancing.

Bitcoin (IBIT −18.28% YTD). Still the clear laggard. Higher-for-longer rates have been a headwind for non-yielding assets and the flows have been choppy. No clear edge; patience.

Credit spreads remain tight — the cleanest “no recession in sight” signal in the entire macro picture. As long as credit is calm, equity pullbacks are more likely to be digestion than regime change.

Part IV: The Regime Status

This is the section that determines how you should be positioning.

• Volatility: Compressed (VIX mid-teens, /VX “dead,” term structure in contango) → premium-selling friendly, long-vol bleeds.

• Momentum: Extended (nine weeks up, records across the board) → respect it, don’t chase it.

• Rates: Eased this week (10-yr ~4.44%) → supportive for now; the swing variable.

• Inflation: Cooling at the margin as oil falls → near-term tailwind.

• Geopolitics: De-escalating (Iran ceasefire hopes) → risk-on, but binary and headline-driven.

• Flows: Risk-on — equity funds seeing renewed inflows led by U.S./tech; bond funds attracting money for an eighth straight week. Performance is forcing money back in.

• Sentiment: Drifting toward greed, not yet euphoric.

Bottom line: a “lean into the trend, but build cheap insurance and watch the bond market” regime — not a crash-imminent setup, but also not a back-up-the-truck moment after nine weeks up. The signals say: participate, protect, and don’t chase.

Part V: Sector Rotation Tracker

Leaders: Technology and semiconductors reclaimed leadership this week on Dell/AI; small caps and broad participation remain constructive; energy gave back ground as oil fell.

Laggards: Rate-sensitive corners (REITs) and defensives lagged a touch as the risk-on, lower-yield mix favored growth. Energy underperformed on the oil drop.

For investors heavily overweight one theme, broad participation (small caps, international, defensives on dips) is the rebalancing opportunity. For traders, the rotation back toward growth is the momentum lane — but it’s the most crowded one, so manage size.

Part VI: What’s on Next Week’s Calendar

A jobs-heavy week — the labor market takes center stage.

• Mon–Wed: Second-tier data and manufacturing surveys; watch overnight headlines on Iran/oil.

• Thursday: Key labor-market reads begin (jobless claims and related data) — can move bonds and overnight futures.

• Friday — the big one: Non-Farm Payrolls + Unemployment Report. This is the week’s defining catalyst. A hot print pressures yields back up (and tests the rally’s rate-relief thesis); a soft print reinforces the “Fed has room” narrative and supports risk. Either way, it’s the number that can move both bonds and stocks.

Actionable: don’t put on aggressive new directional positions into Friday’s jobs number. Let the print clear, then react. Month-/week-end rebalancing flows can also distort price around the data — not a great time to read too much into a single session.

Part VII: Actionable Observations and Trade Ideas

The section you came for. None of this is investment advice — it’s educational framing.

For Active Traders

1. Keep selling premium — with discipline. Compressed VIX + contango + a market overdue for digestion is a favorable backdrop for theta-positive structures. The standard playbook still works: ~30–45 DTE entries, short legs outside the expected-move zone, defined risk over naked, manage at ~21 DTE. Don’t size up assuming you’ll collect crash-day credits — that’s how a calm tape turns a good strategy into a bad week.

2. Express AI upside cheaply, don’t chase it. On extended single names (semis, AI infra), slightly-OTM call spreads (14–30 DTE) capture upside at a fraction of the cost and risk of chasing shares at highs. Wait for pullbacks to support before adding directional longs.

3. Buy convexity while it’s cheap. Index OTM put spreads (5–8% OTM) are inexpensive here and act as portfolio insurance into the jobs catalyst. This is the regime to own a little downside, not just sell it.

4. Trade the bond tell, not the VIX. Watch the 10-year/ /ZB. A yield breakout back above ~4.65–4.75% is your early-warning signal — fade equity strength and tighten risk if it happens. A move below ~4.30% says the melt-up extends; stay constructive.

5. Fade the energy headlines, don’t trend-trade them. Oil’s de-escalation drop has created two-way, mean-reverting moves in the energy complex. Treat sharp XLE selloffs on Iran headlines as short-term setups, not the start of a trend — and keep size modest because the next headline can reverse it.

6. Respect the jobs number. Lighten directional exposure into Friday’s NFP; let it print, then position. The asymmetry of holding a big directional bet into a known binary catalyst is rarely worth it.

For Investors (Longer-Term Positioning)

1. Let extension trigger rebalancing. Nine weeks up is the cue to trim what’s grown outsized — especially concentrated mega-cap tech — and redeploy toward broader participation: small caps (IWM has been leading), international, and “real economy” sectors. You’re not calling a top; you’re managing the geometric-return risk of being maximally long at an extreme.

2. Buy cheap insurance now. Volatility is on sale precisely because nobody feels they need it. A small (1–2%) allocation to downside protection — long-dated OTM index put spreads or tail-risk structures — is far cheaper today than it will be after a decline. Buy the umbrella while the sun is out.

3. Hold gold (and broad metals). The commodity strength is structural, not panic — central-bank demand, deficits, and physical demand. A 5–10% allocation continues to make sense as a hedge against the whole macro framework.

4. Add breadth: small-cap and international. With the Russell leading and participation broadening, investors overweight the S&P 500 can reasonably diversify into small-cap and international exposure as a rebalancing move.

5. Cash still pays ~4.5%. There’s no penalty for keeping 10–15% dry powder for opportunistic deployment. Don’t reach for risk at a regime extreme just because cash feels boring — that optionality is valuable when the next pullback arrives.

What to Watch Going Into Next Week

1. The 10-year yield — does this week’s relief hold, or do yields back up again? This is the single most important variable.

2. Friday’s jobs report — hot vs. soft sets the tone for both bonds and equities.

3. Oil / Iran headlines — does de-escalation stick (inflation stays tame) or break down (oil and yields snap back)?

Risk Range for Next Week

For traders: what the options market is implying for next week’s range, using SPY (~$756.48):

• 5-day Expected Move (1σ): roughly ± $9–11 → range ~$746–767

• 10-day Expected Move: roughly ± $14–16 → range ~$741–772

Stay outside the expected-move zone with your short strikes and the structural odds work in your favor. A weekly close above ~$772 means the rally extended beyond expectations; a close below ~$741 means the character of the move has changed. Either is a regime tell worth acting on.

Part VIII: How to Read This Market

The mental model that keeps working in 2026: respect the price action, position for digestion, and never assume the rally either melts up forever or rolls over instantly.

Right now everything is a tailwind — momentum, AI, falling oil, easing yields, dead volatility, risk-on flows. That’s wonderful, and it’s also precisely the condition under which complacency is most dangerous. When the whole board is green, the one variable that can flip it is usually the one nobody’s watching. This week, that’s the bond market.

So you position so that any outcome is survivable and profitable. You sell premium where the math is favorable. You buy cheap convexity where the insurance is on sale. You rebalance toward breadth as concentration builds. You keep dry powder for the opportunity that always shows up when the regime shifts. And you watch the 10-year and Friday’s jobs print like they matter — because they do.

Nine weeks up is a gift. The discipline is to enjoy it without believing it’s permanent.

This update is the map. Paid members get the territory.

Up above, we said two things: buy protection while volatility is cheap, and rotate idle cash into higher-return structures. That’s the what.

Paid members got the how — in real money, the same day we did it: the exact tail hedges we’re building because vol is this cheap (strike by strike), and the idle cash we just pulled out of T-bills and rotated into a brand-new income structure targeting $300–400 a week. Three real-money portfolios, every trade alert with strikes, sizes and Greeks, daily position updates, and the full 13-module Masterclass on premium selling and tail-risk hedging.

See what we’re actually doing →

The market doesn’t reward the trader who knows the what. It rewards the one who executes the how.

Have a great weekend.

— TonyB & TonyR Grow Your Pile

This is an educational analysis of weekly market activity through Friday, May 29, 2026. Not investment advice. Options and futures involve substantial risk and are not suitable for all investors. Past performance does not guarantee future results.

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Hi GYP Member,

In Part 2 of our Tail Risk Hedging series, we moved beyond simply discussing hedges and began exploring how some of the world’s most successful investors prepare for events that most people believe will never happen.

• The reality is that markets spend most of their time moving gradually higher.

• Then, without warning, something breaks.

• COVID.

• The Volmageddon volatility event.

• The banking crisis.

That is why this session focused on the philosophy and the mechanics of tail-risk hedging — and this time we didn’t just talk about it. We placed the trades live, on screen, in a real Grow Your Pile portfolio, walking through every unit and every dollar.

This One Is for Paid Members

This session was one of the most valuable hours we’ve recorded — so the full walk-through below is for paid GYP members.

Here’s a taste of what’s behind the wall:

• The exact 4-trade “cheap put” ladder we placed live — and the surprisingly small budget that funds it (hint: on a $100K account it’s roughly $100 a month, not $5,000)

• The 3×5 put ratio backspread built into a program that ends with 36 long “crash” puts on essentially for free — the doubling trick that gets you there

• The one rule that decides whether a hedge actually protects you (most traders get the units backwards)

• The harvesting secret — the part that’s harder than putting the hedge on, and where most people give back the entire payoff

• Two bonus structures — including one backtested at +$53,000 on a single unit

If you’ve ever wondered how Universa made a fortune in COVID while everyone else panicked — this is the mechanical playbook.

👉 Become a paid Grow Your Pile member to watch the full session + read the complete breakdown

The market doesn’t reward the trader who knows that hedges exist. It rewards the one who knows how to build them, finance them, and harvest them.

Watch the Full Session:

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Trade Card:

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Instead of one trade, we placed six different BSH structures today — one of each “flavor” we’ll cover in the session. Each one is a live demonstration of a different way to build crash insurance into a portfolio.

The format below is also different. Instead of a full Trade Card per structure (which would make this email a mile long), each BSH variant is a short summary block — name, structure, cost, and a one-line “why this exists.” For the full deep-dive on each, join Session 2 live tonight (link in your inbox if you’re a paid member).

The Six BSH Variants — Quick Comparison

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We’re now leading every trade alert with a Trade Card at the top — a single visual block summarizing the trade in 30 seconds. If you only want to see what we did and why, the Trade Card is all you need. Read it, you’re done.

If you want the full context — the regime read, the decision framework, the Greeks impact, the lessons — keep scrolling. The long-form commentary below is for subscribers who want to learn how to think about trades like this, not just what we placed.

The card is color-coded:

• 🟢 Green = closed winner

• 🔴 Red = closed loser

• 🔵 Blue = new opening trade

• 🟡 Yellow = roll / adjustment

Today’s card is yellow — a roll.

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Tomorrow 5PM ET — Black Swan Office Hours Session 2 (Paid Members) Preheader: $600,000 from 10 hedge units in August 2015. $233K-$290K in Feb 2018. Universa-style returns in March 2020. Tomorrow we build the retail version live.

🗓 Friday, May 29, 2026 · Session 2 of 3 🕔 5:00 PM Eastern · 4:00 PM Central · 2:00 PM Pacific

🔒 Paid GYP members only.

Session 1 Recap

Last Friday in Session 1, we covered why to hedge — the math (a 50% loss requires a 100% gain to recover), the structural mispricing of tail options (the Tail Premium that institutions like Universa systematically harvest), and exactly what Universa Investments did to generate documented returns of 3,612% on the month in March 2020.

We introduced the convex structure family: long puts, put spreads, and the 1/2 ratio backspread that forms the foundation of any serious tail hedge.

Session 2 is the build-out. Now we go from “I understand why this works” to “I have a self-funding hedge program running in my account.”

What Session 2 Is About

Most retail traders who try to build a hedge program quit within 6-12 months. The drag adds up. The hedges expire worthless month after month. The market keeps grinding higher. The temptation to “save the premium” wins. And then, eventually, the crash hits — and the unhedged trader gets destroyed.

The traders who survive don’t have better timing. They have a better system — one where the hedge program funds itself after the initial seed period.

This is the BSH Factory. Tony has been running this model for years. After 6-12 months of operation, the harvested short-put premium pays for the ongoing BSH purchases — meaning the hedge program costs you nothing net of operations for the life of the account.

That’s what Session 2 builds, live, end to end.

🔒 The Series is For Paid Members Only

The detailed agenda, the StreamYard meeting link, and every Session 2 / Session 3 / white paper resource is reserved for paid GYP subscribers.

If you’re a paid member, scroll down for the meeting link.

If you’re not yet a paid member, become one here. You’ll get full access to:

• Tomorrow’s Session 2 + the recording afterward

• Session 3 (mid-June) — Mastering the Hedge / Valley of Death

• The GYP Tail Risk Hedging White Paper — 13-section deep reference

• The full 12-module Options Selling Masterclass

• Every daily trade alert and the live members dashboard

👉 Paid Members — Register here to join Tomorrow

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Market Regime Read

• Vol: VIX 16-17 area, /VX still anchored below 20. Continued compression. SPY Expected Move today ±$2.05 (0.27%).

• Momentum: 9th up-week in a row developing. Every dip bought within hours. Sellers can’t get traction.

• Catalyst: Quiet calendar this week. Holiday-shortened week. AI narrative still dominant. Bond yields stable but elevated.

• SPY position: $750.95 — within 5 points of recent ATH. Front-of-book P1 short puts (the ones still working) sit ~50-100 points below current, comfortably OTM.

The defining feature of this regime, as TonyR notes: the market won’t pull back enough to let us re-enter at fair-margin strikes. Every short-put we built during the brief April/early-May dips has run deep into profit faster than the original DTE expected. The /MES 7325P closed today is the cleanest example — 9 days from entry to 63% decay, with /ES never threatening the strike.

TonyR Commentary

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Market Regime Read

• Vol: VIX 16-17 area, /VX still anchored below 19. Compression continuing. SPY EM today ±$2.05 (0.27%) — tight holiday-shortened opening, then quiet drift.

• Momentum: 8+ weeks of upside. Today’s open continued the pattern — buyers leaning in despite no fresh catalyst.

• Catalyst: No major economic prints today. NVDA digestion ongoing. Yields still elevated but stable.

• SPY position: $749.87 — ~5 points below ATH zone. Front-of-book shorts (Jun 716×2, Jun 718×1, now Jul 710×2, Jul 715×2) remain comfortably OTM.

TonyB Commentary

Another strong market opening this morning accompanied by continued volatility contraction.

In environments like this, the mechanics of rolling short puts become extremely important. When rolling positions around the 21-day window and keeping the same strike selection, the adjustment naturally creates a slightly positive long delta shift. Because of that, I’m intentionally starting with my furthest out-of-the-money short puts first, since those provide the smallest increase in long delta exposure.

Had the market opened weaker or sold off early, I would have approached the adjustments very differently. In that scenario, I likely would have started with my closest-to-the-money short puts, which would create a larger positive delta increase and allow the portfolio to lean more aggressively into weakness.

This is a good example of how trade management should adapt to market conditions rather than follow a rigid formula.

Additionally, I rolled the same strikes out to July, extending duration while maintaining similar positioning. Rolling the two long puts out to July also reduced the buying power requirement by approximately 50% compared to the prior adjustment involving the 710 puts. That is a meaningful improvement in capital efficiency while still maintaining similar portfolio protection and directional exposure.

At this point, I’m more than likely done rolling for the day.

The plan remains flexible:

• If we get a downtick or some weakness in the market, I will likely continue rolling additional puts higher to maintain long delta exposure.

• If markets continue grinding sideways-to-higher with volatility compressed, I’m perfectly comfortable sitting tighter and allowing the faster theta decay of the June options to continue working in our favor.

That’s the balancing act in this type of market: maintaining enough long delta to participate while also maximizing theta decay and preserving buying power flexibility.

Strong trends require constant small adjustments — not oversized reactions.

— TonyB

The Trades:

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Why We Closed Instead Of Waiting For The Rest

The full max profit on this trade was $1,075 if /ES expired below 7560 tomorrow. We took $550 — about half of that — and walked away. Here’s the math behind the decision:

1. We already had 50% of max. Our standard rule across the systematic book is to take profits at 50% on short premium. Even though this trade was a rule-breaker on the way in, the exit discipline still applies. Once you’re at 50%, you’ve already captured the part of the trade where the risk/reward was working in your favor. The remaining 50% requires holding through an overnight session in a thin holiday market, on a naked call, with unlimited tail risk above the strike.

2. Risk/reward flipped against us. At open, we were collecting $1,075 with maybe $4,000-5,000 of realistic downside risk if /ES gapped 50-80 points overnight. After 9 hours of decay, we were now risking that remaining $525 of profit against the same unlimited upside tail. The math gets worse as decay extracts the easy premium.

3. It was a rule-break to begin with. Holding a rule-breaking trade overnight would be compounding the rule-break. Closing it intra-day, even at a partial win, restores discipline.

50% in 9 hours on a 1-DTE trade is a great outcome. Annualize that and the math is silly. Take it.

The Honest Truth

We got lucky.

Let’s not dress this up. /ES traded sideways-to-slightly-down for most of the holiday session. The market gave us almost no real test. The trade worked because nothing happened — not because the analysis was clever.

Had /ES gapped 30 points higher at any point, we would have been sitting on a $1,500-2,000 paper loss, watching naked call delta accelerate against us, with cash markets closed and limited ability to manage cleanly. The fact that didn’t happen is not a vindication of the strategy. It’s a reminder that unlimited-risk strategies can pay you 60 times in a row and then take it all back on trade #61.

1. Size discipline saved us. One contract on a $1M+ P1 portfolio is roughly 0.1% notional. If we’d been wrong, the loss would have been annoying — not a portfolio event. If you take nothing else from this trade, take this: the size you use to break a rule has to be the size you can afford to lose entirely. That’s the only honest way to “break a rule.”

2. Speed of profit ≠ quality of decision. Making $550 in 9 hours feels great. But the speed of the win doesn’t validate the entry. The entry was emotional. The exit was disciplined. That asymmetry — emotional in, disciplined out — is how you stay in the game over decades.

Where We Are Now

• Position: flat on the /ES naked call leg.

• P1 portfolio: back to its pre-Memorial-Day Greeks profile, plus +$550 cash.

• We’ll re-engage with the systematic book on Tuesday’s open. Real setups only.

Real-Life Footnote — The Padres, A Lobster-Dog, And $160 Worth Of Memorial Day

For full transparency: this trade actually became a winner while I was sitting at a San Diego Padres game. That was the Memorial Day plan all along — futures order in the morning, ballpark in the afternoon, watch theta do its job from the stands.

I also tried something new at the park: a Hot Dog + Lobster Roll combination. A “Lobster-Dog,” if you will. And honestly? Amazing. I’m a believer.

The problem: one Lobster-Dog and a beer for two people, with tip, came out to $160 plus. Which means a single round of ballpark food and drinks ate up almost half of today’s $550 profit.

So if you want the real picture: nine hours of holding unlimited tail risk on a naked /ES call netted me $550, and the Padres took $160 of it back in roughly twelve minutes at the concession stand.

Was it worth it? The Lobster-Dog was excellent. The trade worked. The Padres did their thing. I’d call that a successful Memorial Day.

Teaching Takeaway

You don’t have to win the whole hand to win the trade.

The temptation when something is working is to hold for more. The temptation when something is dangerous is to hold and hope. Both temptations lose money over time. Discipline lives in the moments when you’ve already won — and you’re choosing to lock it in rather than press it.

Tomorrow morning, that 7560 call may expire worthless and we’ll “leave $525 on the table.” Or /ES gaps up 40 handles and the contract trades to $50 — and the trader who held would be down $1,500-2,000. We don’t know which. We don’t need to know. The 50% rule eliminates the question.

That’s the whole point of having rules.

— TonyR & TonyB Grow Your Pile

Disclaimer

This trade alert documents the exit of a previously-disclosed trade that violated our published rules on naked short calls. The $550 profit is not a recommendation to replicate the structure. The same trade could just as easily have produced a $2,000+ loss had the market moved against us during the holiday session.

We took the position in size we could afford to lose entirely. We exited at the standard 50% profit target. Neither of those mechanics turns a rule-breaking trade into a strategy you should adopt.

Grow Your Pile is educational content only. Nothing in this alert constitutes investment advice or a recommendation to buy, sell, or hold any security or derivative. Options and futures trading involve substantial risk and are not suitable for all investors. Past performance does not guarantee future results. Trade your own portfolio at your own risk and within your own risk tolerance.

Closing alert published Memorial Day evening, May 25, 2026. Entry: this morning at 9:50 AM. Exit: 6:31 PM. Round-trip: 9 hours. Net: +$550 (51% of max profit). Position flat.

Memorial Day — A Pause Before the Trade

Today is Memorial Day. A day to be grateful to all the men and women who sacrificed so we can live and enjoy the freedoms we have.

Some of the most meaningful things behind Memorial Day:

• Honor — recognizing courage and service.

• Sacrifice — acknowledging those who gave their lives for others.

• Gratitude — appreciating freedoms that are often taken for granted.

• Reflection — remembering the personal stories behind the names.

• Unity — a moment where politics and differences are meant to pause in respect.

Before we get to the trade, take a minute to remember why we have the freedom to even sit at a screen and do this for a living.

Market Context — The Strongest Bull Run In Years

This weekend brought another “peace agreement.” We’ve had so many at this point I’ve lost count.

What’s interesting — and what tells you everything about the current regime — is this: every rumor sends the market screaming higher, and when the rumor turns out to be untrue, the market doesn’t go down. That asymmetry is the cleanest tell I know of for a strong bull tape. Buyers show up on good news and refuse to sell on bad news.

This is the strongest bull run I have seen in many years.

The cash market is closed today for the holiday. But the futures market is not.

The Trade — And Why I’m Telling You Not To Copy It

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There’s a number that should have made every premium-seller’s head turn this week — and almost nobody noticed it.

That’s exactly the moment Mark Spitznagel’s Universa built itself around. That’s exactly the moment our 3-part Black Swan Hedge series was designed for. And Friday night, we kicked the series off with a 90-minute live session breaking down exactly what to do.

If you missed Session 1, this is what was covered.

The Setup

Tony B opened the session with a stat most traders missed: the average three-month put-to-call skew on the S&P 500 has dropped from 1.30 (during the April pullback) to 0.80 today. That’s a complete crash in demand for downside protection. The market is positioned so heavily long, and so unworried about a drawdown, that the OPTIONS market is no longer pricing in any meaningful risk of one.

Which means two things:

1. If you sell premium for a living, the math just got more dangerous. Premium selling works because implied vol consistently exceeds realized vol — that’s the structural edge. But when implied vol is COMPRESSED to historic lows, the cushion for unexpected moves is thinner. Tony R’s exact words: “In order for premium selling to work, there has to be some tail risk that can really bite your ass.”

2. If you want to hedge, this is the cheapest window of the last two decades. Insurance is cheap when nobody wants it. Tony R: “Yeah, it’s the time to think about it when nobody’s thinking about it.”

That’s why Session 1 spent the entire hour walking through hedge structures from the most plain-vanilla to the most surgically-applied — so you can choose the right tool for YOUR portfolio while the windows still open.

What’s Inside Session 1

We covered four hedge structures in detail, walked through live option chains on SPY, NVDA, and AAPL, debated trade-offs in real time, and addressed several subscriber questions. Here’s what was on the menu:

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In the market update, we covered the macro — eight straight up weeks, yields at 2007 highs, NVDA’s monster quarter, the regime status, what’s on next week’s calendar.

TonyR Commentary

All selling once again got reversed almost immediately.

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This is the full deep-dive — what happened, what it means, what’s on next week’s calendar, and what we’re watching tactically going into Monday. Designed for traders AND investors. No portfolio specifics here — just the market.

Part I: The Week at a Glance

The S&P 500 closed up roughly 0.9%, marking its eighth consecutive weekly advance — the longest winning streak since late 2023. The Dow added 2.1% (third up week of last four) and set a fresh all-time closing high. The Nasdaq added 0.5% (its seventh up week of last eight). Russell 2000 quietly outperformed at +14.61% YTD.

The character of the week is what’s worth understanding. Stocks traded LOWER Monday and Tuesday as Treasury yields hit multi-decade highs. The bond market dominated until Wednesday, when sentiment shifted on two converging events: NVDA’s blowout earnings, and reports of potential progress in U.S.-Iran negotiations. Oil pulled back from above $110 toward $100, yields eased, and equities resumed the climb. By Friday, all three majors sat at or near fresh ATHs.

NVDA delivered exactly the print bulls wanted:

• Revenue ~$81.6 billion, up ~85% year-over-year

• Strong earnings beat across the board

• $80 billion stock buyback announced

Despite that, NVDA initially SOLD OFF on the news Wednesday before recovering into Friday. The muted reaction tells you something important about positioning extremes — we’ll come back to it.

Year-to-Date Standings

Part II: Five Themes That Defined the Week

Theme 1: A Historic Winning Streak — and What History Says About What’s Next

Eight consecutive weekly gains is rare. Looking at historical analogues since 2000, the market has managed similar streaks roughly 12-15 times. Post-streak behavior breaks roughly into three buckets:

• ~40% of the time: streak extends 1-2 more weeks before a meaningful pullback (5-10%)

• ~35% of the time: streak ends abruptly with a 5-15% correction within 4-8 weeks

• ~25% of the time: streak rolls into sideways consolidation lasting 1-3 months

The actionable takeaway: statistically, the path of least resistance for the next 4-8 weeks is NOT continued melt-up at this pace. The expected-value distribution shifts toward sideways chop or correction. Aggressive chase-the-rally trades have worse risk/reward here than they did 8 weeks ago when the rally was just starting.

For traders: premium-selling structures (which benefit from sideways action or modest pullbacks) become structurally more attractive than directional long bets. For investors: this is the moment to think about rebalancing — not because the rally is “over,” but because being maximally long at this point exposes you to the geometric-return punishment of a sharp drawdown more than it rewards you with marginal upside.

Specific levels:

• S&P consolidates 7,250-7,400 next 1-2 weeks → healthy digestion

• Breaks above 7,500 with vertical price action → exhaustion behavior, often precedes 5-10% pullbacks

• Breaks below 7,200 on heavy volume → rally character has changed; defensive positioning makes sense

Theme 2: AI and Semiconductors Are the Most Crowded Trade on Wall Street

Bank of America’s monthly Global Fund Manager Survey released this week confirmed it: long Magnificent 7 / semiconductors is now the single most crowded trade on Wall Street. That extreme matters for two reasons.

First, NVDA’s earnings reaction is the textbook crowded-trade behavior. The company delivered ~$81.6B in revenue (+85% YoY), beat on virtually every metric, and announced an $80B buyback. By any rational measure, that’s a blowout. And yet the stock initially sold off. When expectations are sky-high and positioning is one-sided, even great results trigger profit-taking from the marginal seller.

Second, the lesson of every crowded trade in history is that when positioning is at an extreme, the next significant move is usually AGAINST the consensus. That doesn’t mean AI is going to crash — structural compute demand is real. It means the next 5-15% move on NVDA, AMD, INTC and the broader semi complex is more likely DOWN than UP from current levels.

Actionable: if you’ve been heavily overweight AI/semis, this is the moment to scale back to neutral. Hold a core position, sell some upside premium if you trade options, keep cash ready to redeploy on the inevitable pullback. For traders specifically: short-dated call spreads on NVDA/AMD/QQQ at slight OTM strikes (14-21 DTE) have been working as low-cost tactical fades.

Theme 3: Oil, Iran, and the Geopolitical Wild Card

This week was a microcosm of how geopolitics is now driving cross-asset action.

Monday/Tuesday: Oil traded above $110 briefly on escalating concerns about a prolonged U.S.-Iran conflict and Strait of Hormuz disruption (through which ~20% of global oil flows). Yields surged in response.

Wednesday/Thursday: Reports of negotiation progress pushed oil back below $100. Yields eased. Equities rallied.

Friday close: WTI ~$96, Brent ~$104. Oil is down 3-4% on the week despite the path — but still ~50% above pre-war levels. Not a fully resolved situation. A “managed but tense” equilibrium.

Why this matters for everyone: Oil at $100+ adds roughly 0.2-0.3% to CPI within 4-6 months for every sustained $10 move. Oil at $110 vs $80 implies 0.6-0.9% more annual CPI than the Fed was expecting earlier this year. Which means more pressure on yields. Which means more pressure on tech valuations. Which means the entire risk-asset complex.

The Iran situation is the single biggest swing factor for the next 4-8 weeks. If negotiations break down and oil sustains above $110: yields push higher (10Y above 4.75%), defensive rotation accelerates, VIX expands to 22-28, tech underperforms, gold pushes toward $4,250-4,300/oz. If negotiations advance and oil settles toward $80: yields drift lower, continued equity grind higher, VIX compression toward 14-15, tech retakes leadership.

Actionable: this is binary risk. Don’t try to predict it — position for both. Hold some long-equity exposure for the “negotiations work” scenario, hold modest tail-risk hedges for the “negotiations fail” scenario.

Theme 4: Treasury Yields at 2007 Highs — The Quiet Crisis

The most under-discussed story of the week. The 30-year Treasury yield touched its highest level since 2007 mid-week. The 10-year touched its highest level in over a year.

Current levels:

• 10-year: ~4.56%

• 30-year: ~5.06%

• 30-year fixed mortgage: ~6.51-6.65%

Three dynamics are pushing yields higher:

1. Inflation expectations creeping back up — oil, geopolitical risk, AI-driven economic activity keeping nominal demand strong

2. Fed rate cut expectations evaporating — a growing number of FOMC members now expect ZERO cuts in 2026. The narrative shifted from “the Fed will help us” to “the Fed is stuck.”

3. Massive Treasury issuance — fiscal deficit running at multi-decade highs. Every auction tests whether bond markets will absorb supply at current yields.

Why this matters for equity markets: Higher long-end yields compress equity valuations through the discount-rate channel. Every 50bp of 10-year yield translates to roughly 7-10% downward pressure on multi-year-out equity valuations. That doesn’t mean the market has to fall — earnings growth can offset multiple compression — but the structural tailwind of low rates is gone.

Specific levels:

• 10-year above 4.75% → material stress for high-multiple tech

• 10-year above 5.00% → material stress for broader market; defensive rotation accelerates sharply

• 30-year above 5.25% → pressure on mortgage-sensitive sectors and very long-duration assets

Actionable: watch the 10-year more than the VIX right now. VIX is reactive — it spikes when stress arrives. The 10-year is leading — it tells you where stress is building. The next 5-10% move in equities will likely be triggered by a yield breakout (either to new highs or back below 4.30%).

Theme 5: Friday’s First Real Pullback Was Healthy

After eight weeks of upside, Friday delivered the first meaningful intraday pullback. The selling didn’t look panic-driven — it looked like profit-taking and exhaustion. The kind of action that creates better entries and improved premium-selling opportunities rather than a regime change.

For premium sellers, this is genuinely useful. IV ticked modestly higher, strike levels reset slightly more attractive, and the post-pullback environment offers fresh opportunities at slightly better entry levels.

Whether Friday was the START of something bigger or a normal mid-rally pause is the central question for next week.

• Next week opens flat-to-up, S&P consolidates 7,350-7,400 → digesting; continued slow grind likely

• Next week opens red and S&P breaks 7,200 → character has changed; defensive positioning makes sense

• Next week rallies back to new highs → melt-up continues; late-cycle exhaustion risk rises

Part III: Cross-Asset Status Check

Treasury Bonds — The Underperformers

TLT is down 2.35% YTD despite ostensibly being in a rate-cutting cycle that should have been bullish for bonds. The bond market has consistently outperformed the rate-cut bulls in the wrong direction.

Why bonds keep struggling: inflation hasn’t fully cooled, fiscal supply is overwhelming, the Fed is on hold, and geopolitical inflation risk via oil keeps surprising to the upside.

What would change the picture: a genuine growth slowdown in employment data, Iran negotiations completing with oil sustainably below $80, or material Fed-communication easing. Until one of these, the path of least resistance for long-end yields stays slightly higher or sideways at uncomfortable levels.

Gold — Quiet Strength at Historic Levels

Gold spot is trading around $4,138/oz (GLD at $413.82, which tracks roughly 1/10th of spot). Up roughly 3.9% YTD — a quiet but persistent uptrend reflecting continued central bank buying, geopolitical risk premium, and currency debasement fears as fiscal deficits balloon.

Gold is increasingly behaving like a structural hedge against the entire macro framework rather than a tactical inflation hedge. For investors: a 5-10% portfolio allocation continues to make sense. Silver, copper, palladium have all outperformed gold YTD — SLV +39%, CPER +25%, PALL +7%. The breadth confirms this is a real industrial-and-monetary story, not just panic narrative.

Dollar, Bitcoin, Credit

The dollar (DXY) is quietly grinding higher — pressure on emerging markets, drag on multinational earnings, tailwind for goods inflation. Not a runaway, but a real factor for any international exposure.

Bitcoin is down 15.67% YTD — higher yields negative for non-yielding assets, post-halving bump didn’t materialize, institutional flows choppier. No clear edge; patience makes sense.

Credit spreads remain tight — high yield is performing well; no stress signal there yet. That’s the cleanest “no recession in sight” data point in the entire macro picture.

Part IV: The Regime Status

This is the section that determines how you should be positioning.

VIX Tells You Almost Everything

Current VIX: 16-18 range (closed Friday ~17)

For context:

• VIX < 14: complacency / extreme low vol

• VIX 14-20: normal regime

• VIX 20-28: elevated / cautious

• VIX > 28: stress / pause new positions

• VIX > 35: crisis / harvest hedges aggressively

We’re in the upper end of the “normal” zone, but closer to the bottom of the historical range than the top. A calm-but-not-complacent regime.

Term Structure: Robust Contango (Calm Confirmed)

VIX futures term structure is in robust contango across the entire curve — futures trading higher than spot at every expiration. The normal state of affairs, occurring roughly 80% of the time historically.

The remaining 20% — backwardation — is when the curve inverts and spot trades higher than futures. Backwardation has preceded 21 of 22 S&P 500 drawdowns greater than 5% over the 2004-2025 period. That single statistic is one of the most useful regime tells in markets. As of right now, firmly in contango. No stress signal.

Translation: the regime says “lean into normal strategies.” Premium-selling environments thrive in contango. Theta-positive structures work. Long-volatility strategies bleed value steadily.

Putting It All Together

• Volatility: Normal-to-compressed (VIX 16-18, contango)

• Momentum: Extended (8 weeks up, indices at or near ATHs)

• Yields: Elevated and pressuring valuations

• Inflation: Sticky with upside risk from oil

• Fed: Hawkish hold (zero cuts now likely in 2026)

• Geopolitics: Tense (Iran), not yet escalating

• Sentiment: Moving toward greed, not yet extreme

Bottom line: this is a “ripe for digestion or correction” regime, not a “crash imminent” regime, but also not a “back up the truck” regime.

The right posture: maintain reasonable long exposure, keep modest hedges in place, be ready to add risk on any 5-7% pullback (which becomes statistically more likely with each additional week of extended upside). Don’t chase. Don’t panic. Run the program.

Part V: Sector Rotation Tracker

The “real economy vs. AI hype” theme keeps strengthening.

Leaders (YTD and recent weeks):

• Industrials (XLI): “real economy” rotation, defense spending, reshoring

• Consumer Defensive (XLP): late-cycle rotation in motion

• Energy (XLE): elevated oil supports the bid

• Utilities (XLU): AI infrastructure → real power demand stories

• Healthcare (XLV): outperforming after sustained underperformance

Laggards:

• Technology (XLK): still positive YTD but underperforming over past 4-6 weeks

• Communication Services (XLC): mixed

• Consumer Cyclicals (XLY): weakening on consumer concerns

• Financials (XLF): mixed

• REITs (XLRE): clearest losers in higher-rates regime

Rotations of this type historically last 6-18 months. We’re 3-4 months in. Expect continued underperformance from rate-sensitive sectors and continued outperformance from defensive/real economy sectors.

For investors heavily overweight tech, this is a structural moment to consider rebalancing. Not abandoning tech — but reducing concentration. For traders, pair trades (long industrials / short tech, long defensives / short cyclicals) have been working well.

Part VI: What’s on Next Week’s Calendar

A heavy data week.

Monday May 26 — Memorial Day (Markets CLOSED). No price discovery. Geopolitical news over the long weekend won’t price in until Tuesday.

Tuesday May 27 — Consumer Confidence Day

• 10:00 AM ET — Consumer Confidence Index

• 10:00 AM ET — Richmond Fed Survey, New Home Sales

Consumer Confidence has been deteriorating gradually. A miss to the downside could be the first hint of real consumer weakness.

Wednesday May 28 — The Big Day

• 8:30 AM ET — PCE Price Index (Fed’s preferred inflation measure)

• 8:30 AM ET — GDP 2nd Estimate

• 8:30 AM ET — Personal Income and Spending

• 8:30 AM ET — Advance Durable Goods

• 8:30 AM ET — Initial Jobless Claims

PCE is the single biggest data point of the week. If core PCE comes in hot (above 2.8% YoY), yields push back to recent highs and equities come under pressure. If PCE shows continued moderation (below 2.6% YoY), it relieves pressure on the Fed and provides tailwind for risk assets.

Thursday May 29: Multivariate Core Trend Inflation (10 AM), NY Fed Staff Nowcast (12:45 PM). Second-tier but can move overnight futures.

Friday May 30: Month-end rebalancing flows. Not a great day to take aggressive new positions.

Part VII: Actionable Observations and Trade Ideas

The section you came for. None of this is investment advice — it’s educational framing.

1. Premium-selling environments continue to work — but with discipline. Compressed VIX + contango + market overdue for digestion creates a favorable backdrop for theta-positive structures. 45-DTE entries with 25-35 delta short legs continue to be the sweet spot. Manage at 21 DTE per the standard playbook. Defined-risk structures (spreads, iron condors) over naked positions — especially with positioning extremes in tech building. Don’t size up assuming you’ll collect crash-day credits.

2. Watch defensive sector setups. Healthcare, Staples, Utilities, Industrials are in strong uptrends. Any 3-5% pullback in XLV, XLP, or XLU back to the 20-day MA has been an attractive level for adding long exposure or selling short puts at ~30 delta strikes.

3. Be cautious adding new long-tech exposure. Crowded-trade dynamics in NVDA/AMD/INTC are real. Even great earnings produced muted reactions this week. Better tactical approaches: sell call spreads at slightly OTM strikes on NVDA/AMD/QQQ for 14-30 DTE; buy QQQ put spreads at 5-8% OTM as portfolio insurance (cheap because VIX is compressed); avoid chasing breakouts in single-name tech — wait for pullbacks.

4. The yield curve trade. Long the 30-year (TLT) into any continued yield spike above 5.10% on the 30-year (or 4.75% on the 10-year) has been a contrarian trade that pays off over 2-4 week windows. Not a screaming buy at current levels — but a tactical setup if next week’s PCE comes in soft and yields drop. Conversely: short bonds (or long TBT) if PCE comes in hot and the 10-year breaks 4.70%+ with conviction.

5. Oil/energy tactical setups. XLE has been bid on geopolitical risk and structural energy demand. Pullbacks in the energy complex (XLE down 2-3% intraday on Iran de-escalation news) have been short-term buy opportunities.

1. Rebalance toward defensive and “real economy” sectors. If your portfolio has been heavily concentrated in mega-cap tech, this is the moment to consider trimming and redeploying. The rotation into industrials, defensives, energy, healthcare has multi-quarter staying power. Adding 5-10% exposure at current levels makes sense for most investors.

2. Build modest tail protection. VIX is compressed. Tail risk hedging is cheap. Even a 1-2% portfolio allocation to defensive structures (long-dated OTM put spreads on SPY, or tail-risk ETFs like TAIL or CAOS) provides meaningful protection in a 10%+ drawdown scenario. This is exactly the regime the Spitznagel/Universa methodology was built for — buy insurance when nobody wants it.

3. Hold gold (and silver, copper). The commodity rally has been broad — gold, silver, copper, palladium all up significantly YTD. This isn’t a panic trade. It’s a structural shift driven by central bank buying, geopolitical risk premium, currency debasement concerns, and physical demand from data center / industrial buildout. A 5-10% portfolio allocation to precious and industrial metals continues to make sense.

4. Consider international and small-cap exposure. Russell 2000 (+14.61% YTD) and Emerging Markets (EEM +11.53% YTD) have been quietly outperforming. After years of mega-cap US dominance, the breadth is extending. If you’ve been overweight S&P 500, adding small-cap and international exposure now is reasonable rebalancing.

5. Cash is still earning ~4.5%. Maintaining 10-15% cash for opportunistic deployment makes sense. Don’t reach for yield by being fully invested at this regime extreme.

What to Watch Going Into Tuesday

Tuesday’s setup (post-Memorial Day open):

1. How does Asia close Sunday night / Monday? Watch for any overnight developments in Iran negotiations, Asian inflation prints, China data.

2. Where do U.S. equity futures open Tuesday morning?

   • Above 7,400 SPX → momentum continues

   • In the 7,300-7,400 zone → consolidation, neutral

   • Below 7,250 → defensive day, watch 7,200 closely

3. Where does the 10-year yield open Tuesday morning?

   • Below 4.50% → bond rally, equity-positive

   • 4.50-4.65% → neutral, range-bound

   • Above 4.65% → yield pressure resumes, defensive rotation extends

Risk Range for Next Week

For traders specifically: what the options market is implying about next week’s range.

Using SPY (current $745.64):

• 5-day Expected Move (1σ): roughly ± $9-11 → range ~$735-757

• 10-day Expected Move: roughly ± $14-16 → range ~$730-762

If SPY closes above $762 next Friday, the rally has extended beyond expectations. If SPY closes below $730, the character of the move has changed materially. Either is a regime-tell worth acting on.

For premium sellers, the Expected Move tells you where to anchor short strikes. Stay outside the EM zone with your shorts, and the structural odds work in your favor.

Part VIII: How to Read This Market

The one mental model that has worked consistently in 2026: respect the price action, position for digestion, never assume the rally either continues straight up or rolls over instantly.

After eight weeks of upside, the path of least resistance is sideways-to-slightly-down for the next 4-8 weeks. Statistically, that’s the most likely outcome. But “most likely” is not “certain” — there’s a real possibility (25-30%) that the rally extends another 3-5% before any meaningful pullback. And an equally real possibility (~25-30%) that we get a fast 5-10% correction in the next 2-3 weeks.

How do you position when the distribution is that uncertain?

You position so that ANY of the outcomes is survivable AND profitable. You don’t go all-in on one direction. You collect premium where the math is favorable. You hold modest tail protection where the math is unfavorable but the convexity is high. You rebalance toward sectors that work in multiple scenarios. You keep cash for the opportunistic deployment that almost always comes when the next regime change arrives.

The market doesn’t reward conviction. It rewards adaptability.

Eight weeks of upside, yields at 2007 highs, NVDA beating expectations, oil swinging $20 in a week, the dollar quietly strong, gold quietly stronger, sectors rotating, AI crowded, bonds underperforming — this is not a simple market. The temptation in a simple-feeling market like this is to think you have it figured out. You don’t. We don’t. Nobody does.

But running the program works. Selling premium when premium is being paid for. Hedging when insurance is cheap. Rebalancing when concentration is building. Trimming when extension is statistical. Adding when fear is real. The signals are there if you read them — and the signals this week are: digest, defend, deploy modestly, and watch next week’s PCE.

Have a great weekend.

— TonyB & TonyR Grow Your Pile

This is an educational analysis of weekly market activity through Friday, May 22, 2026. Not investment advice. Options and futures involve substantial risk and are not suitable for all investors. Past performance does not guarantee future results.

Want the daily portfolio context, trade alerts, and our complete 13-module Masterclass on premium selling and tail risk hedging? Become a paid Grow Your Pile member for the full picture.

📢 REMINDER — TONIGHT: GYP Black Swan Hedge Office Hours · Session 1 of 3 · FREE for GYP members ONLY !

The first session of our 3-part Black Swan Hedge Series starts tonight on StreamYard. Why hedge (the math), the full Universa methodology breakdown, and an intro to the convex structures we use. Open to paid subscribers —. Sessions 2 and 3 build the BSH Factory and cover Valley of Death management.

🆕 NEW: GLD Is Now Live in the Put Selector

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Regime Read — Where We Are Right Now

• Volatility: VIX continues compressed in the 16-18 range (opened around 17.58, ranged 16.60-17.87). Vol is now making fresh local lows even as the rally extends. Implied premium remains expensive to buy and cheap to sell — exactly the regime where premium-selling theta engines thrive.

• Momentum: Eight consecutive weeks of upside. SPY at $747.24 today is up roughly $7+ from yesterday’s $739.53. The Dow set a fresh record. Nasdaq lagging (NVDA digestion). The rally character has shifted from “earnings-driven” to “relief-driven.”

• Catalyst: US-Iran negotiations progress is the headline catalyst today — geopolitical relief is driving the bid. Treasury yields easing. NVDA post-earnings (Wed evening) had a mixed reception (beat EPS, sold off on supply/geo concerns) but didn’t disrupt the broader tape.

• Internal rotation: Industrials, Consumer Defensive, and Energy leading. Tech, Communications, and Cyclicals lagging. The “real economy vs AI hype” rotation is intensifying, not fading.

What this means for YOUR book: This is continued roll-up territory, not new-structure territory. Vol is too compressed to be selling fresh tail-rich premium; the program runs by lifting existing positions higher as the market grinds up. The Jade Lizard restructure today is a regime-specific decision: when vol compresses and the rally extends, the call-side of a Lizard becomes a short-delta drag faster than expected. Manage it accordingly.

TonyB Commentary

I placed five trades today, and four of them were simply rolling up existing puts — not necessarily because I wanted to aggressively add exposure, but more out of necessity.

After nearly eight consecutive weeks of market strength, with SPY rallying another four dollars today while volatility continued making new lows, our short puts have performed extremely well. The challenge, however, is that as the market continues grinding higher, those positions naturally lose long delta exposure and become less effective at participating in additional upside.

Ideally, I prefer rolling puts during periods of weakness and expanding volatility, when premiums are richer and adjustments are more efficient. But this market has not been giving us many of those opportunities. The trend remains relentless, volatility remains compressed, and waiting too long to adjust can leave the portfolio underexposed to continued upside momentum.

The most interesting trade this week, however, was the Jade Lizard structure we initiated.

We originally sold the Jade Lizard at $10.94 on the 18th, and just four trading days later it was trading near $9.15, even briefly closing around $8.75. What’s fascinating is how dramatically the Greeks evolved over such a short period of time.

On entry, the trade carried approximately +7 to +10 long deltas. But after the continued market rally and volatility contraction, the position effectively flipped from long delta to slightly short delta — roughly negative 2 to 3 deltas by today.

That created a very important portfolio management decision:

Close the call spread portion — or — Roll up the naked put to regain long delta exposure

I elected to close the call spread because I had already rolled up several existing puts elsewhere in the portfolio, which already restored much of the long delta exposure I wanted.

Had this Jade Lizard been a standalone position without the broader portfolio context, I likely would have chosen the other route — rolling up the short put to regain the original +5 to +10 long deltas the structure initially provided.

This is another important reminder that trades should never be evaluated in isolation.

A structure that may be perfect as a standalone trade may need to be managed differently when viewed through the lens of the entire portfolio. Sometimes portfolio-level Greeks, buying power usage, and overall directional exposure matter more than maximizing the outcome of any single position.

For now, we continue adapting to what the market is giving us:

• Rolling up selectively

• Maintaining disciplined sizing

• Respecting the strength of the trend

• And staying flexible as volatility remains historically compressed

— TonyB

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• Volatility: VIX continues compressed in the mid-teens. NVDA earnings cleared last night without disrupting the broader tape — the binary-event overhang is now removed. Implieds remain stable; the rally is grinding without expanding fear or greed.

• Momentum: Second consecutive quiet up day. SPY at $739.53 vs $737.54 yesterday. Slow grind higher continues, but breadth and conviction remain modest. This is “rally inertia” more than “rally reignition.”

• Catalyst: NVDA cleared. Earnings season largely behind us. Rates remain the macro variable to watch — yields stabilizing for now, but the May 19 pullback memo still applies (stocks + bonds can fall together in rates-driven regimes).

What this means for YOUR book: This is the regime where premium selling shines and directional bets struggle. Vol compression rewards theta-driven structures (short puts, ratio spreads, jade lizards) and punishes structures that need directional follow-through (diagonals, ratio backspreads needing a move). Today’s portfolio action — exiting the directional diagonals, doubling down on the theta engine — fits the regime exactly.

TonyB Commentary

Watching that diagonal spread on a daily basis since entry turned into a very interesting real-time volatility and structure experiment.

As the trade developed, the spread consistently contracted and moved against us at times by more than $1 per contract, despite the market not making a major directional move lower. That price action told us a lot about how the volatility relationship inside the structure was behaving.

If you remember, on entry July implied volatility was approximately one point higher than June volatility, and that relationship largely remained intact throughout the life of the trade. The problem was that June volatility started lower from the beginning, which never really created the ideal setup for front-month volatility contraction that we would normally like to see in a traditional diagonal spread.

At the same time, the long delta component of the trade never truly got the upside expansion we were looking for. The market simply did not provide the type of directional follow-through necessary for the structure to fully perform.

Today we elected to close the trade essentially for a scratch to a small winner.

More importantly, we used the opportunity to roll up puts and continue selling June volatility — which has been consistently profitable for us — while also replacing the long delta exposure we lost from exiting the diagonal spread.

That’s an important lesson in portfolio management: sometimes the original thesis simply does not play out the way we expected, even if the trade structure itself was logical on entry.

Rather than stubbornly holding and hoping, we adapted.

The takeaway here is not that diagonal spreads “don’t work,” but rather that volatility relationships matter tremendously. When the front-month volatility structure does not cooperate and directional momentum stalls, the trade can struggle to expand even if price action is not outright bearish.

Lesson learned.

As always, the market gives feedback every day, and part of becoming a better trader is learning how different structures behave under different volatility environments.

— TonyB

The Trades:

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How a Famous Hedge-Fund Made 3,612% in 30 Days.

We’ll Build the Retail Version Live This Friday.

🗓 Friday, May 22 · Session 1 of 3

🕕 5:00 PM Eastern · 4:00 PM Central · 2:00 PM Pacific

Announcing the GYP Black Swan Hedge Series

Black Swan hedging is too big a topic for a single Office Hours session. Most traders walk away from a one-hour explanation with a vague sense that “yes, hedging is important” but no actual ability to build a hedge that works.

So we’re not doing that.

We’re spending three full Office Hours sessions breaking down exactly how the world’s best tail-risk funds (Universa, Ambrus Capital, Spitznagel-style operators) structure their crash insurance — and how to build the retail-accessible version yourself.

Why We’re Spending Three Sessions on This

In March 2020, while the S&P 500 lost 30% in twenty-three trading days, Mark Spitznagel’s Universa Investments turned in a 3,612% return on their flagship Black Swan Protection Protocol.

Not 36%. Not 361%. Three thousand six hundred and twelve percent.

So what were they actually doing?

Universa’s protocol is built on deep out-of-the-money put options on the S&P 500 — convex tail-risk structures that cost very little in calm markets but explode in value during crashes. They size the position as a small percentage of the portfolio (single-digit percent), buy continuously, accept the slow drag in calm years as the cost of insurance, and harvest aggressively in the 1-2 day window when implied volatility peaks during a crash.

That’s it. No black box. No quantitative magic. Just deep-OTM puts, sized smartly, held continuously, and harvested at the right moment.

When SPX crashed 30% and VIX hit 80+ in March 2020, those deep-OTM put structures gained thousands of percent — hence the 3,612%. They didn’t predict March 2020. They were positioned for it. That’s the difference between traders who survive a crash and traders who don’t.

The same structural foundation Universa uses is exactly what we teach in our BSH program — just scaled to institutional size with their proprietary refinements. Spitznagel literally wrote a book about the principle (Safe Haven: Investing for Financial Storms). Nassim Taleb is the advisor. The math is public. The structures are public. The discipline is public.

So why doesn’t every premium seller run one?

Two reasons:

1. Most premium sellers think hedging is “wasted money” — until the day it isn’t.

2. Even the ones who want to hedge don’t know how to structure the trade so it actually pays off when it matters.

That’s what the three-part series fixes — in depth, with the time to actually teach it.

Session 1 — What You’re Going to Learn This Friday

This first session is the foundation. We answer why hedging works mathematically, why even the best premium sellers in the world spend 2-4% of their portfolio every year on insurance they hope they never use, and how the institutional benchmark (Universa) actually does it.

✔️ The math you can’t argue with — why a 50% drawdown requires a 100% gain to recover, the recovery-time table at every common drawdown level, and the difference between arithmetic and geometric returns that determines whether you compound wealth or compound losses.

✔️ The two structural mispricings on the volatility surface — the Volatility Risk Premium (what we harvest selling premium) AND the Tail Premium (what Universa harvests buying tail protection). Both are real. Both can be combined. Most traders only know about one.

✔️ The Universa deep dive — exactly what Mark Spitznagel and his team actually do. The delta zones they target (−0.02 to −0.10), the DTE windows they use (90-180 days primary, up to 2 years on some legs), the rolling cadence (monthly, mechanical, no market timing), and the portfolio allocation framework (3.33% of portfolio, 2-4% annual cost budget).

✔️ The convex structure family — introduction to long puts, put spreads, and the 1/2 ratio backspread that forms the foundation of every convex tail hedge. We’ll walk through the payoff geometry, why convexity matters more than expected value, and how to think about “shape” instead of “average return.”

✔️ The deep-OTM trap most retail hedgers fall into — buying tail puts so far out of the money they wouldn’t pay off even in a real crash. We’ll cover the actual delta zones that protect you vs the lottery-ticket strikes that just expire worthless.

✔️ Why now matters — the May 19 rates-driven pullback was a regime warning. Stocks down + bonds down = a different kind of stress than 2008 or 2020. We’ll cover why your existing hedges might not be doing what you think they’re doing.

What’s Coming in Sessions 2 & 3

Session 2 — The BSH Factory (early June)

Now that you understand why hedging works, Session 2 is how to build a self-funding hedge program at retail scale. The 1/2 and 3/5 BSH structures in deep detail. The Factory Model — how harvested short-put premium funds ongoing hedge purchases until the program pays for itself within 6-12 months. Sizing rules per portfolio size. Regime-based deployment (when to buy, hold, harvest). Real crash payoff numbers from Aug 2015 ($600K), Feb 2018 ($233-290K), and March 2020.

Session 3 — Mastering the Hedge (mid-June)

The hardest part of running a hedge program isn’t building it — it’s NOT cutting it at the worst possible moment. Session 3 covers the Valley of Death (the price zone where shorts hurt but longs aren’t yet convex, where most hedge programs die from trader psychology, not bad math). The three conditions you need to see before adjusting mid-crisis. The five exit rules. Delta speed triggers for mechanical hedge sizing. The common mistakes — including the deep-OTM trap, rolling in the valley, and selling hedges right before they pay off. Plus multi-asset complements: VIX call spreads, tail ETFs (TAIL, CAOS, SWAN, BTAL), defensive sector rotation, and the regimes where bonds STOP working as a hedge.

We’ll close the series with live Q&A integrating everything from sessions 1, 2, and 3.

After Each Session — The White Paper

Within 24 hours of Session 3 (the final session in the series), every attendee — and every GYP subscriber, free or paid — will receive the GYP Tail Risk Hedging White Paper.

This is the deepest, most thorough reference document we’ve ever put together. Thirteen full sections covering every option-based, ETF-based, and multi-asset tail hedge currently available to retail traders, plus the framework for choosing among them, plus the full Universa methodology breakdown.

It’s deeper than anything in our 12-module Masterclass. It’s the document we want every paid GYP member to have on file as a permanent reference.

You don’t want to miss it.

Submit Your Questions Ahead of Time

This is a deep series. The more specific your questions, the better the answers.

📩 tonyr@squaredtcapital.com

For Session 1 specifically, send questions about:

• The math of hedging vs the cost of hedging

• How Universa-style strategies actually work mechanically

• Whether tail protection makes sense for your account size

• Why your current hedges (if any) might not be doing what you think

• The difference between insurance, lottery tickets, and convex structures

For Sessions 2 and 3 — questions about BSH mechanics, Factory Model implementation, and Valley of Death management — we’ll collect throughout the series.

Why This Session Matters Even More Right Now

The last six weeks have been one of the most powerful momentum rallies in recent memory. SPX broke out, the FOMO chase began, and most traders forgot that markets actually pull back.

This week we got the first real two-day pullback. Stocks down, bonds down, rotation into defensives, small caps leading lower. Yesterday I wrote about why this is a rates problem not a recession scare — and why the textbook 60/40 hedge isn’t working when both halves sell off together.

That’s the kind of market that demands an answer.

If you’ve been running premium sales naked or with under-built hedge protection, now is the moment to learn this — not after the next 10% drawdown. Markets don’t ring a bell at the top. They gap down on a Sunday night.

Why You Should Be There — All Three Sessions

The Volatility Risk Premium is real. It’s how we make money week in and week out selling premium.

But there’s a second structural premium most traders never even hear about — the Tail Premium. Investors systematically underpay for far-out-of-the-money protection. That mispricing is what Universa harvests in crashes. And it’s exactly what we want our subscribers to know how to harvest too.

The hedge isn’t the opposite of premium selling. It’s the complement. They feed off opposite sides of the volatility surface. Both edges are real. Both can be harvested. The traders who combine them are the ones who survive over decades — not just months.

Over three sessions, we put the whole picture together. Session 1 starts Friday.

👉 Session 1 is free for paid subscribers Only.

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