The Whale Week Playbook

How to Trade with the Smartest Money on Wall Street

This report is the culmination of a multi-day training series designed to show you how to follow the most powerful trading signals in the market, those generated by hedge funds, institutional investors, and corporate insiders. It’s not about copying trades. It’s about decoding intent, filtering for conviction, and building a repeatable, disciplined approach to trading with smart money.

Whale Week was created to help you develop that edge. The material here is dense by design. But if you use it right, this playbook becomes a long-term resource.

How to Use This Report

Each section can stand independently, but the system works best when you connect the dots. You’ll find strategic breakdowns, real-world trade setups, and clear execution guidelines. For visual examples and case studies, refer to the linked slide decks and replays.

Access the Original Whale Week Content

Below are the direct links to each day’s material:

• Day 1 – [Presentation Link] – [Video Replay]
• Day 2 – [Presentation Link] – [Video Replay]
• Day 3 – [Presentation Link] – [Video Replay]
• Day 4 – [Presentation Link] – [Video Replay]
• Day 5 – [Presentation Link] – [Video Replay]

Featured Trades from Whale Week

These three trade setups were selected during the live sessions as high-conviction examples of applying the smart money framework in real time. Details and technical setups for each trade are expanded later in the report, but here’s your quick-reference snapshot:

Trade Idea #1: LYFT (June 20, 2025 $18 Put)

This is a clean momentum-fade setup on a stock with no real story or support. LYFT popped briefly after Engine Capital ended its activist campaign. Still, with no follow-through and no institutional backing, the stock drifted back into a resistance zone it failed to break multiple times.

Technically, LYFT is stretched. RSI and MFI are both elevated. Last time it touched this range, it rolled over hard, and now the setup is even weaker. This is where momentum fades become tradeable: when retail enthusiasm isn’t backed by real buying power.

• Entry: ~$2.22 (If the entry price is close to this Tuesday, the trade is still good to execute)
• Stop: $1.50
• Target: ~$15
• Why it works: You’ve got a failed catalyst (activist exit), an overbought signal (RSI/MFI), weak fundamentals (no profit, no edge vs. Uber), and no support below. This isn’t a trade against a name. It’s a trade against structure. LYFT is technically vulnerable and institutionally ignored. If momentum rolls, this drops fast.

 

Trade Idea #2: TEAF (Tortoise Essential Assets Income Term Fund)

This is your smart-money, value-insulated, income-backed trade. TEAF is a closed-end fund focused on essential infrastructure, pipelines, renewables, utilities, all assets with pricing power and reliable dividends. It’s trading at a discount to NAV, which means you’re buying the portfolio for less than it’s worth.

Technicals are starting to confirm: it’s nudging above the 20-day moving average, signaling a possible breakout from the base. The fund’s exposure to midstream energy, a sector with strong insider buying and solid free cash flow, adds a macro tailwind.

• Entry: Market Price ($11.71)
• 20-Day SMA: 2% above price
• Stop: $10.92 (2x ATR = $0.76)
• Why it works: It’s rare to find a discounted CEF with this level of quality exposure, especially in income-generating, inflation-insulated assets. With insider accumulation in similar names, improving technical structure, and a dividend-backed cushion, TEAF is a low-volatility opportunity with asymmetric upside. A great hold during market chop.

Trade Idea #3: KTOS (Kratos Defense & Security Solutions)

This is a strategic play on defense sector momentum + insider conviction. Kratos develops tactical unmanned systems and national security tech, and its CEO, Eric DeMarco, has bought twice since March, once after announcing a joint venture with Rafael (Iron Dome developer), and again ahead of the U.S. “Golden Dome” missile defense plan.

The stock has strong momentum, trading ~3.5% above its rising 20-day, and institutional tailwinds behind it. But instead of chasing it higher, we’re positioning below the CEO’s buy point using a put credit spread. This is a stock that offers unique upside if the U.S. does implement the Golden Dome defense system.

 

• Trade Type: July 18, 2025 Put Credit Spread
• Sell: $32.50 Put ($1.14)
• Buy: $30 Put ($0.60)
• Net Credit: $0.54 on $1.96 margin
• Breakeven: $31.96
• Probability of Profit: ~75%
• Return on Risk: ~27% (176% annualized)
• Why it works: This is the classic insider-confirmed sector trade, backed by rising institutional interest, clear technical structure, and a well-timed catalyst. With the CEO buying at $33.59, you’re placing a high-probability bet that the stock stays above $32.50 while capturing a solid risk/reward skew. You’re letting momentum and conviction work while keeping your downside boxed in.

 

Know the Players and Their Strategies

To follow smart money, you need to understand who you’re following. A 13F from Carl Icahn doesn’t mean the same as one from Renaissance Technologies. One is launching a campaign to shake up the boardroom. The other may have already exited before the filing hit the site. The fund’s strategy determines how you interpret their activity and whether their moves are actionable.

Who Files 13Fs?

Any institutional manager with over $100 million in AUM is required to file a Form 13F quarterly. That includes:

• Hedge funds
• Mutual funds
• Family offices
• Pension funds
• Sovereign wealth funds
• Insurance companies

These filings disclose U.S. equity holdings only. They exclude shorts, foreign stocks, and cash positions, which means context matters. Time your follow-up using technicals and insider activity.

Fund Types and Their Strategies

Traders Worth Following

We’ve grouped the most influential investors by style. These names showed up frequently in the Whale Week training sessions.

Long-Term Value & Macro

• Warren Buffett – Berkshire Hathaway
• Michael Burry – Scion Asset Management
• Ray Dalio – Bridgewater Associates
• Jeffrey Ubben – ValueAct Capital
• Mario Gabelli – GAMCO Investors

Activist Hedge Funds

• Bill Ackman – Pershing Square
• Jeff Smith – Starboard Value
• Dan Loeb – Third Point
• Nelson Peltz – Trian Partners
• Keith Meister – Corvex
• Barry Rosenstein – JANA Partners

Closed-End Fund Arbitrage

• Boaz Weinstein – Saba Capital
• Phil Goldstein – Bulldog Investors

Quantitative & Short-Term

• Renaissance Technologies
• Two Sigma / DE Shaw

Passive Giants

• BlackRock, Vanguard, and State Street dominate 13F ownership due to index fund exposure. Not conviction trades, but their weight creates momentum and technical pressure.

Pro Tip: Filter by manager type. If multiple value or activist funds are in a name, it’s a signal. It may just be passive flow if it’s just Vanguard and BlackRock.

 

Understanding the Filings

Each SEC filing tells you something different. One shows what they bought. Another shows why they bought it. Some filings are legally delayed, others are nearly real-time. Knowing which is which, along with how to read between the lines, is where the edge begins.

Form 13F – The Hedge Fund Portfolio Snapshot

What it shows: Long U.S. equity positions for institutions with over $100M AUM
When it’s filed: 45 days after each calendar quarter
What’s included: Common stock, ETFs, options
What’s excluded: Shorts, cash, foreign equities

How to use it:

• Focus on new positions, doubled stakes, and top 5 holdings by size
• Cross-check for sector rotation and macro trends
• Use price action, insider buying, and volume to confirm intent

Example: In Q1 2025, Scion Asset Management (Michael Burry) filed massive put positions on NVDA. The 13F alone didn’t say “short,” but the options structure implied a bet against the stock. That was a trade to confirm with RSI and volume before chasing.

Form 13D – Activist Intent

What it shows: A new stake of 5%+ with intent to influence management
When it’s filed: Within 10 days of acquiring the stake
What to look for: Letters to the board, proxy fights, board nominations

Why it matters:

• 13D filings often lead to a 5–10% short-term pop, followed by months of strategic pressure
• Activists may push for asset sales, spin-offs, buybacks, or leadership changes

Example: Bill Ackman’s 13D on ADP started a public campaign and helped push the stock over 30% higher during his activist campaign.

Another classic example: Starboard Value’s activist campaign against Darden Restaurants (parent of Olive Garden) led to major leadership changes and operational reforms that drove the stock significantly higher over the following year.

Starboard’s 13D on Darden Restaurants and the resulting activist-led turnaround.

Not every 13D is about replacing the board. Carl Icahn’s 2013 campaign targeting Apple focused entirely on increasing shareholder value through aggressive buybacks. The pressure didn’t lead to a proxy fight, but Apple began returning capital at a historic scale, and the stock re-rated for years afterward.

Carl Icahn’s 13D on Apple (2013) sparked a multi-year rally driven by capital return, not corporate restructuring.

Form 13G – Passive Accumulation

What it shows: A 5%+ stake by a passive investor
When it’s filed: Within 10 days for qualified institutions, or 45 days after year-end for everyone else
Common filers: BlackRock, Vanguard, State Street

Why it matters:

• Often signals long-term accumulation
• May front-run ETF additions, index weighting changes, or sector flows

A 13G may not mean short-term action, but repeated 13G filings by large managers can create tailwinds for a stock, especially if the stock enters an ETF or becomes more heavily weighted in an index.

Form 4 – Real-Time Insider Activity

What it shows: Trades by executives, directors, and 10%+ owners
When it’s filed: Within 2 business days of the transaction

What to watch for:

• Code “P” = Purchase (open market buy)
• Clusters (multiple execs buying at once)
• The CEO and CFO buy (highest conviction signals)

How to read it:

• Ignore awards, gifts, and option exercises unless they’re followed by open market purchases
• Look for buying near support or technical levels

Example: In March 2022, Occidental Petroleum had a 13D filing from Warren Buffett, followed weeks later by CEO Vicki Hollub’s Form 4. Together, they signaled strong insider conviction and triggered a multi-month rally.

OXY rallied after Buffett’s 13D and was later reinforced by CEO Vicki Hollub’s insider buying.

 

Insiders You Might Overlook: Politicians

Politicians aren’t subject to the same insider trading rules as corporate executives. Their trades are filed through the STOCK Act, often weeks after the fact, but they still provide a signal.

• Watch for trades by lawmakers on committees related to the companies they buy
• Tools like QuiverQuant track this activity

Example: Senator Markwayne Mullin bought shares of Badger Meter, a water infrastructure company, shortly before the EPA mandated a tech upgrade to water systems, something his committee oversaw. The stock surged over 40%.

Timing and Context Are Everything

Each form gives you a piece of the puzzle:

• 13F shows what they own
• 13D shows why they’re buying
• 13G shows who’s quietly building a stake
• Form 4 shows what insiders believe

Used alone, these filings can mislead you. Combined with technical filters and macro context, they become powerful tools.

 

Filtering for Tradeable Signals

Understanding how to read the filings is just the start. The real work comes in identifying which ones matter. Most trades disclosed in a 13F or Form 4 are irrelevant.

Leftovers from passive flows, stale positions, or token insider gestures. But the ones that do matter tend to follow a pattern. They’re sized aggressively. They cluster. They show up right before a breakout. And when they do, volume tends to spike and price moves with intent.

The key is filtering for conviction. Finding the trades that come with real weight behind them. That means evaluating:

• Who’s buying – Is it a respected activist? A long-term value fund? A cluster of insiders?
• How much they’re buying – Are they building a top-five position? Doubling their stake?
• Whether price action confirms intent – Is the stock breaking out on volume, or just drifting sideways? When those pieces start to align, you’re no longer guessing. You’re tracking a move with institutional force behind it.

How to Spot Conviction in a 13F Filing

Not all positions in a 13F carry the same weight. Focus on the following:

• New positions: Fresh entries this quarter signal active conviction
• Top 5 holdings: These often represent a fund’s strongest ideas
• Position size: Use this formula: Position Value ÷ Total Portfolio Value. Anything over 5% is meaningful
• Doubled positions: A 2x or greater increase in share count shows building confidence
• Cross-fund overlap: If multiple unrelated funds buy the same name in the same quarter, pay attention

Insider Cluster Buying: The Real Tell

When multiple insiders, especially a CEO, CFO, and director, buy in the same window, that’s one of the strongest signals you’ll find. Prioritize:

• The CEO buys (strategic insight)
• CFO buys (balance sheet visibility)
• Multiple executives within the same window
• Look for transaction code P = open market purchase

Insider buying clustered near the 20-day moving average often precedes a breakout.

Stacking Signals for High-Probability Setups

The best trades stack multiple signals. This is where smart money trading moves from idea to strategy.

When two or more of these align, conviction is high. When they all line up, it’s time to move.

This is how you go from watching whales to swimming with them.

Macro Filters to Layer On

Context matters. A great setup in the wrong environment will struggle. Here are the filters that can make or break a trade:

• Insider Buy/Sell Ratio: Tracked in dollar terms. When the ratio spikes in favor of buying, sentiment is turning
• Breakouts vs. Breakdowns: Look at breadth. Are more names breaking out than breaking down?
• Liquidity Expansion: Follow central banks and global credit. When liquidity rises, risk assets gain support.

Insider buying tends to spike when liquidity tightens, often signaling market bottoms. Source: Whale Index.

 

Use these macro overlays to time entries and exits. Smart money is early, but not reckless.

Tools to Help You Filter

You don’t need to build all this from scratch. Here’s the core toolkit that will get you there:

• WhaleWisdom – Screen funds, track conviction, analyze overlap
• BAMSEC – Summarize filings, get alerts, study positions by date
• QuiverQuant – See insider clusters and Congressional trades
• FinViz Elite / TradingView – Apply technical screens and overlays
• gov / Form4.com – Dive into raw filing data and footnotes

Combine these tools. A QuiverQuant insider cluster flagged on a BAMSEC 13F, confirmed by technical strength on TradingView? That’s your trade.

 

Trade Setups and Execution

Signals are only as good as your ability to act on them. Knowing that a whale bought a stock doesn’t help unless you understand how to build a trade around it. That means knowing what kind of setup you’re looking at, how to enter, and where to manage your risk.

Some trades are short-lived. Others take months. A clear event drives some. Others are slow builds. Below are five proven setup types based on years of watching how smart money behaves.

Catalyst Buy

A catalyst buy comes when a major event triggers immediate interest, like a fresh 13D or insider spike. You’re catching a wave of re-rating or institutional momentum.

• Timeframe: 2–10 days
• Entry: Breakout above short-term resistance on volume
• Risk Control: Stop under breakout level or recent support

Swing Trade

This setup leans on technicals and conviction positioning. It’s about catching a clean trend over a short window.

• Timeframe: 1–3 weeks
• Entry: Bounce off the 20- or 50-day moving average with confirmation
• Risk Control: Stop under the moving average or recent low

Campaign Hold

You’re in for the long haul. These work best when an activist outlines a full agenda, buybacks, board seats, and spin-offs.

• Timeframe: 3–12 months
• Entry: Anywhere inside the base, timing isn’t the key here; conviction is
• Risk Control: Give these more room; use wide stops or portfolio allocation limits

Breakout Entry

Momentum setup. The stock has built a base and is ready to break. You’re playing the breakout and a possible retest.

• Timeframe: 1–2 weeks
• Entry: Break above the range high with confirmation
• Risk Control: Stop just below prior resistance

Event Trade

These revolve around scheduled catalysts, earnings, proxy votes, deal announcements. Get in with a clearly defined exit.

• Timeframe: 1–5 days
• Entry: Ahead of or in reaction to the event
• Risk Control: Tight, predefined stop based on expected move

Entry Filters That Matter

Before entering, confirm:

• Price has cleared the 20- or 50-day SMA
• RSI is between 55–70 (strong but not overbought)
• The MACD crossover has occurred
• MFI is trending up from neutral
• Volume spike is 1.5–2x average

You don’t need all of them. But two or three should line up.

Examples of Timeless Smart Money Execution

Occidental Petroleum (OXY)

This trade combined conviction, timing, and technical clarity:

• 13D from Warren Buffett
• Insider Form 4 from CEO Vicki Hollub
• Entry came after the consolidation
• Breakout followed

This setup took months to play out.

The move was over 100%. It’s a reminder that good trades often look boring at first.

Structuring the Trade

Common Shares – Best for illiquid names or long-hold positions. Use stop-losses under support.

Directional Options (Calls/Puts) – Great when options are liquid. Stick to 30–60 DTE. Risk 1–2% max.

Spreads (Verticals) – Use when volatility is high. Lower cost, defined risk. Match your strike with support/resistance.

Scaling & Exits – Scale out in thirds:

• 1st: On breakout or initial move
• 2nd: On continuation or strength
• 3rd: Let ride with a trailing stop

Pre-Trade Checklist

Before you click “buy,” ask:

☐ Is this a new or growing position?

☐ Is the buyer someone reputable?

☐ Is price clearing resistance or a key moving average?

☐ Is volume confirming?

☐ Are technicals and macro aligned?

☐ Do I have a clear stop and exit plan?

The setup is live if the answer is yes to 5 or more. If not, wait.

Risk Management and Process

Even the cleanest setup can fall apart without proper structure. Risk management isn’t a safety net, it’s the framework that keeps you consistent, rational, and long-term profitable. Every smart money trade you take needs to be built with downside protection and process discipline baked in.

This section walks through how to size trades, where to place stops, how to scale out of winners, and what routines keep you focused.

Position Sizing

Discipline starts with size. Most losing streaks come from one mistake: betting too big.

• General rule: Risk no more than 1–2% of your total capital per trade.
• Options: Go smaller. Use a portion that reflects the total premium at risk, not the notional size.
• Spreads: Stick to defined risk. Your max loss is your bet.

Don’t get seduced by conviction. The strongest idea in the world can turn sour on one bad headline. Sizing is your first line of defense.

Stop Placement

Stops need to live where the trade breaks, not where your emotions want to go.

• ATR-based stop: Use 1.5x the average true range below your entry.
• Structural stop: Below support or a key moving average.
• Event-based stop: Just outside the implied move for earnings or news-driven trades.

Avoid arbitrary levels. Every stop should have a reason.

Scaling and Exits

Good trades move in waves. You want to reduce risk as it works in your favor.

• Scale out in thirds:
  • Take the first third off after a breakout.
  • Trim the second on a strong move or follow-through.
  • Let the final third ride with a trailing stop or moving average break.

This lets you book gains without losing your position and avoid giving it all back.

Weekly Trading Routine

Smart money trading thrives on rhythm. Build a flow that makes review and execution automatic.

Routine creates clarity. Without it, the week becomes noise.

Journaling and Trade Review

If you’re not reviewing, you’re not improving. Build a log that tracks not just outcomes but also thought processes.

• Why did I take this trade?
• What was the signal?
• What was my entry/exit/stop?
• What worked? What didn’t?
• Would I take this again?

Review every Friday. Look for setups that consistently produce. Track mistakes and tighten them.

What to Avoid

Some of the most common failures in this process involve abandoning the structure you spent the time building.

• Chasing every 13F or Form 4 without confirmation
• Oversizing based on name recognition alone
• Ignoring technicals and market context
• Holding losers just because a whale is still in
• Skipping your review process

Don’t let someone else’s conviction override your discipline. The goal isn’t to follow blindly, it’s to trade professionally with better data.

 

Pitfalls, Patterns, and Final Thoughts

Smart money trading can be incredibly powerful, but only if you know where the traps are.

Many traders chase the wrong signals, overreact to headlines, or abandon structure as soon as a name gets hot.

What separates professionals from amateurs is restraint, pattern recognition, patience, and an ability to stay focused on the process over hype.

Common Pitfalls

These are the mistakes I’ve seen, and made, too many times:

• Blindly following 13Fs without context or technical confirmation.
• Mistaking passive flows (BlackRock, Vanguard) for conviction trades.
• Ignoring timing, most 13F positions were entered weeks ago.
• Chasing Form 4s when the stock is already extended.
• Overestimating activist success (not every campaign ends in a buyback or board seat)
• Overweighting trades just because a big name is attached

Example: Bill Ackman took a large position in Nike in late 2023, expecting a turnaround. But the stock continued to slide, and he exited with a loss. Not every activist campaign leads to outperformance, and not every whale trade plays out the way it’s planned.

If you’re following a whale, ask yourself: “Do I understand the strategy behind the position?” If not, don’t trade it.

Patterns That Repeat

When filings align with technicals and liquidity, the edge is real. Here are the patterns that show up again and again in successful smart money trades:

• Cluster buys by multiple insiders just above a key support level
• Whale accumulation followed by a breakout above the 20-day or 50-day SMA
• Activist 13D + insider buy within weeks of each other
• Insider buy + low float leading to momentum spike.
• Closed-end fund trades where activist enters near a 15–20% NAV discount
• Macro pivot + insider buying = early sign of sector rotation

You don’t need to trade every setup. You only need to learn the ones that fit your style and repeat.

Final Thoughts

There’s no shortage of noise in the market. Every day, you’re hit with charts, opinions, earnings headlines, and talking heads. What you rarely get is clarity. A way to cut through all of it and follow real money with real conviction.

That’s what Whale Week is about.

This isn’t a newsletter strategy. It’s not based on opinion or narrative. It’s based on legal disclosures filed by the most sophisticated investors in the world. And those disclosures tell a story, who’s buying, how much they’re risking, and what they’re betting on.

But edge doesn’t come from copying trades. It comes from understanding why the trade happened, when the signal matters, and how to structure your own entry with risk in mind. You’ve learned how to do that here.

You now have a repeatable framework:

• How to track the right funds
• How to interpret 13Fs, 13Ds, 13Gs, and Form 4s
• How to filter for conviction
• How to time your entries with technicals
• How to stack signals
• How to manage risk like a professional

There’s no secret to this. Just process, repetition, and discipline. You’ll miss trades. You’ll stop out of good setups. You’ll get late entries. That’s normal. The edge is in sticking to the system and knowing you’re not chasing noise, you’re following capital.

This playbook doesn’t end here. Revisit it often. Build your own tracker, create your own watchlist, journal your trades, and adjust your filters.

This is how you stay a step ahead, not by guessing what’s next, but by following the people who already know.