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James Whelan and Daniel Moss sit down for a candid shop-floor conversation about how they actually run money and make decisions as a team. Two seasoned market practitioners, they cut through the noise to show how collaboration drives better execution, cleaner risk, and calmer heads when it counts. If you’re a trader wondering what really happens behind the screens—how ideas are vetted, positions are sized, and exits are enforced—this interview brings you right into the room.
In this piece, you’ll learn the core of their strategy: following price and momentum across asset classes, balancing discretion with rules, and knowing when to press a winner or stand down. We’ll unpack how James and Daniel think about team-based decision-making, building conviction without ego, using options for income, and staying defensive when conditions demand it. The goal is simple and beginner-friendly: give you a practical playbook you can adapt to your own trading—clear rules, better exits, and a mindset that prioritizes capital preservation and steady growth.
James Whelan Playbook & Strategy: How He Actually Trades
Market Philosophy: Price First, Narrative Second
Here’s the big picture James operates from: price action and trend structure lead, narratives follow. He respects macro context, but won’t fight the tape or hold “clever” views against clear momentum. This keeps him adaptable across equities, ETFs, rates, and commodities when conditions flip.
- Trade what’s moving: only allocate to assets making higher highs/higher lows or breaking bases on expanding volume.
- If the price disagrees with your thesis for two closes, the thesis is wrong—flatten or flip.
- Never average down in downtrends; redeploy into strength only.
- Macro is a filter, not a trigger: the chart must confirm before capital goes in.
- Track relative strength (RS) vs. a broad benchmark and rotate into the top quartile only.
Setup Selection: Clean Trends, Liquid Vehicles
James prioritizes clean, liquid instruments—often ETFs or highly traded single names—so execution is tight and slippage is minimal. The goal is simple: remove idiosyncratic noise and ride the dominant move.
- Longs: buy breakouts above multi-week ranges with rising 20/50-day moving averages and RS in the top quartile.
- Shorts/defense: use failed breakouts, lower-highs under a declining 50-day, or breakdowns from tight bear flags.
- Avoid “messy” charts: overlapping bars, whipsawing MAs, and thin liquidity.
- For sectors/factors, prefer the ETF expressing the theme rather than the noisiest single stock.
- Require at least two of three: price trend up, RS improving, and breadth confirming (advance/decline, % above MA).
Risk Sizing & Position Construction: Small Edges, Big Discipline
Position sizing is where longevity lives. James uses volatility-aware sizing so one trade can’t wreck the book. He thinks in portfolio risk, not just trade risk.
- Risk per trade: 0.25%–0.75% of equity; never exceed 1.0% on a single position.
- Size by ATR: shares = (risk $) ÷ (ATR × k); set k between 1.5 and 2.5 based on regime.
- Cap aggregate correlated risk: max 3% total risk across highly correlated assets.
- Hard stops always live in the system—no mental stops.
- If daily drawdown hits 1.5%–2.0%, stop trading for the day.
Trade Management: Add to Strength, Cut to Rules
Winners deserve more capital; losers deserve the exit. James scales in only when the market proves him right and scales out when momentum stalls.
- First scale-in only after price moves +0.5R in favor and pullback holds prior breakout level.
- Trail with structure: below higher lows for trends; switch to a short EMA/ATR stop once +2R.
- Partial at +1R (25% off) to pay risk; let the rest run to +3R–5R if trend persists.
- No “give-back” over 40% of open profits once above +2R—tighten trailing stop.
- If three trades in a row fail on the same setup, pause that setup for one week and review.
Portfolio Balance & Exposure: Offense When It’s There, Defense When It’s Not
Exposure breathes with the market. The book expands in strong breadth and contracts when internals deteriorate.
- Core exposure bands: 0%–30% (defense), 30%–60% (balanced), 60%–90%+ (offense).
- Use a breadth dashboard (e.g., % of names > 20/50-day MAs, new highs/lows) to shift bands.
- In defense, concentrate on the top 2–3 themes only; avoid shotgun positioning.
- In offense, diversify by theme/timeframe to avoid single-factor shock.
- Raise cash fast if the major index loses its 50-day on expanding volume and breadth slides.
Macro Overlay: Themes Without the Hero Calls
James respects rates, inflation, and growth cycles—but the overlay refines risk, it doesn’t predict turns. He’ll tilt into themes the tape already confirms.
- Don’t front-run central banks; react to price after events, not before.
- If the two-year yield breaks trend higher, tighten risk on duration-sensitive assets.
- Commodities: only engage when price confirms breakout and term structure isn’t hostile.
- Equity factor tilts (quality, momentum, value) must show RS improvement for two weeks.
- When macro is muddy, trade smaller and shorten holding periods.
Options Overlay: Income, Hedging, and Smoother Equity Curve
Options are tools for shaping payoff lines, not lottery tickets. James uses simple structures to define risk and buffer volatility.
- Covered calls on trending longs once they’re extended: 20–40 DTE, strike near 0.25–0.35 delta.
- Collars into event risk: buy puts 1–2 ATR below, sell OTM calls to finance.
- Cash-secured puts only on names/ETFs he wants to own at the strike; avoid during breadth downtrends.
- Never sell naked options into falling volatility—the premium is mispriced against you.
- Hedge the book, not the ego: index puts when portfolio beta is high and breadth weakens.
Execution & Timing: Let the Market Print the Invite
Entries are invitations, not obligations. James lets price prove readiness and avoids “almost setups.”
- Enter on confirmed breakouts: close above the level, plus volume expansion or strong RS thrust.
- Use stop-limit or staged orders to reduce slippage around obvious levels.
- No new risk in the last 15 minutes if it pushes the daily drawdown to limits.
- Skip trades around thin liquidity windows and major data prints unless hedged.
- If spread + slippage > 15% of planned risk, pass—edge is compromised.
Routine & Preparation: Process Before P&L
Consistency comes from a repeatable daily rhythm. The routine keeps emotions out and execution crisp.
- Pre-market: update RS lists, breadth, top bases, and risk bands; finalize A-setups only.
- During market: alerts at levels, not screen-glued micromanagement; follow checklists.
- Post-market: journal entries with chart snapshots, R multiples, and adherence score.
- Weekly: prune laggards, rotate into top themes, and reset exposure bands.
- Monthly: audit system stats (win rate, avg R, expectancy) and cut any rule that isn’t pulling weight.
Team Communication & Review: Clear Rules, Shared Language
James treats communication as a risk tool. Shared definitions for setups and exits reduce hesitation and second-guessing.
- Use a single taxonomy for setups (e.g., “Base-breakout A,” “Pullback-to-20 A/B”).
- Pre-define exit triggers so anyone can manage the position if needed.
- After action reviews within 24 hours for outsized wins/losses, extract one improvement each time.
- If conviction diverges across the team, default to a smaller size, tighter stops.
- Track “process errors” separately from market losses; only the latter are acceptable.
Drawdown Protocols: Survive First, Thrive Second
The edge is staying in the game. When the environment or execution slips, James shifts to preservation mode.
- At −5% equity drawdown: halve risk per trade and reduce exposure band by one notch.
- At −8%: trade A-setups only; no discretionary adds; tighten trailing stops.
- At −10%: trading halt for 48 hours; deep review of logs, breadth, and rule compliance.
- No “get-back” trades—recover with normal size and process.
- Restore risk only after two consecutive profitable weeks with full rule adherence.
Mistake Proofing: Guardrails Against Yourself
Even pros drift without guardrails. James hard-codes protections so his worst day is survivable and rare.
- Hard platform limits: max daily loss, max number of trades, and cooldown timers.
- Ban list for patterns that historically underperform your stats.
- Use checklists before entry/exit; if two boxes fail, skip the trade.
- Automate alerts for RS deterioration and stop proximity to avoid “forgetting.”
- Celebrate rule-following, not P&L—process is the only lever you truly control.
Daniel Moss Playbook & Strategy: How He Actually Trades
Market Philosophy: Trend Clarity Over Opinion
Daniel keeps his edge by prioritizing objective trend signals over personal narratives. He treats every idea as a hypothesis that must be confirmed by price and breadth before capital is deployed. This philosophy keeps him on the right side of big moves and out of chop.
- Trade only in the direction of the prevailing trend on the daily timeframe, confirmed by the weekly.
- Require alignment: price above the 50-day and 200-day for longs; below both for shorts/defense.
- If price closes against the thesis two sessions in a row, exit—opinions don’t get a third day.
- Stand aside in low-clarity regimes (declining breadth, overlapping ranges, whipsawing MAs).
- Let relative strength decide where to play; rotate into leaders, not laggards, with potential.”
Setup Selection: Clean Structures, High Liquidity
He focuses on liquid ETFs and large-caps, so fills are clean and slippage doesn’t eat the edge. Structures must be obvious enough that risk can be defined and managed without second-guessing.
- Long setup: base breakout with rising 20/50-day MAs, RS in top quartile, and expanding range/volume.
- Add-on setup: first pullback to the rising 20-day that holds the prior breakout level.
- Avoid overlapping bars, wide wicks, and news-dependent rockets that collapse just as fast.
- Prefer theme exposure via ETFs when single-name risk is unnecessary.
- Decline any setup where the stop distance exceeds 1.2× your standard ATR risk budget.
Risk Sizing & Position Construction: Volatility-Aware by Default
Sizing is the fail-safe. Daniel sizes by volatility so every trade carries comparable dollar risk, and he caps correlation so clusters of similar positions can’t sink the book.
- Risk 0.25%–0.75% of equity per trade; hard cap 1.0% on A+ only.
- Position size = (risk $) ÷ (ATR × 2.0); widen to 2.5 in higher-vol regimes.
- Max 3% aggregate risk across correlated assets/themes.
- Pre-load stop orders at entry; no “mental” stops.
- If daily P&L hits −1.75%, stop initiating new risk for the day.
Trade Management: Pay Yourself, Protect the Core
He scales responsibly—adding only when the market proves him right and trimming when momentum stalls. The aim is to keep winners “safe” while giving them room to trend.
- Take 25% off at +1R to bank risk; move stop to breakeven on the remainder.
- Add only after a constructive pullback holds the breakout level and momentum re-accelerates.
- Use structure for trailing: under swing lows for trends; switch to ATR trail after +2R.
- Cap gives back at 40% of open profit once above +2R.
- Three consecutive failures on the same setup = temporary moratorium and review.
Portfolio Exposure & Balance: Adaptive Offense and Defense
Exposure breathes with the tape. Daniel expands in healthy breadth and contracts fast when internals deteriorate, keeping drawdowns shallow and recoveries faster.
- Exposure bands: 0–25% (defense), 25–60% (neutral), 60–95% (offense).
- Raise exposure after two consecutive breadth thrusts and a major index reclaim of the 50-day with volume.
- Cut exposure if % of names above 50-day drops below 45% for two days.
- Concentrate on the top 2–3 themes during defense; diversify across factors/timeframes in offense.
- Keep at least 10% cash buffer at all times for opportunity or hedging.
Macro Overlay: Use the Map, Drive by the Road
Macro guides risk tilt, not entries. Daniel lets rates, currency moves, and commodity trends inform where to lean—but only after price has already validated the theme.
- No pre-event gambles: reduce size into central bank days; redeploy post-print if trend confirms.
- Rising 2-year yield + weakening breadth = tighten stops and shorten holding periods.
- Favor commodity and value tilts only when their RS ranks have improved for two consecutive weeks.
- When macro is noisy, lower position size by one notch and focus on shorter swing cycles.
- If cross-asset signals conflict, default to less exposure, wider patience, and quicker profit-taking.
Hedge & Options Overlay: Smooth the Ride, Define the Risk
Options are tools for shaping payoff, not speculation. Daniel uses simple structures to protect the equity curve and harvest income when trends are extended.
- Index puts are used as portfolio hedges when beta is high and breadth rolls over.
- Covered calls on stretched longs: 20–35 DTE, 0.25–0.35 delta to ease mean reversion.
- Cash-secured puts only on ETFs/stocks he’s happy to own at strike during healthy breadth.
- Avoid short premiums into collapsing volatility; sell premiums when IV is elevated vs. realized.
- Hedge the book, not individual egos—one index hedge often beats multiple messy micro-hedges.
Execution & Timing: Let Price Confirm the Invite
Entries happen at confirmation, not anticipation. Daniel uses alerts and staged orders to reduce slippage and avoid chasing emotional candles.
- Enter on confirmed close above/below the level; if intraday, require volume/range expansion.
- Use stop-limit or staged entries around obvious levels to avoid bad fills.
- Don’t add risk in the last 15 minutes if doing so breaches daily loss limits.
- Skip the first minutes after major data drops unless the plan includes a predefined hedge.
- If spread + expected slippage > 15% of defined risk, pass on the trade.
Routine & Preparation: Template Before Tactics
Process is the performance enhancer. Daniel runs a tight daily/weekly loop, so decisions are faster and cleaner under stress.
- Pre-market: refresh RS ranks, breadth stats, A/B setups, and exposure band plan.
- Midday: run a quick adherence check—if two checklist boxes fail, halt new entries.
- Post-close: journal entries with chart snapshots, R multiple, reason for exit, and emotion tag.
- Weekly: rotate into new RS leaders, prune chronic underperformers, and recalibrate risk bands.
- Monthly: compute expectancy, drawdown depth/duration, and rule compliance score.
Team Communication & Playbook Clarity: One Language, Zero Doubt
He treats shared language as a risk control. When everyone knows the exact triggers and exits, execution speeds up and hesitation drops.
- Maintain a standardized setup taxonomy with screenshots of A, B, and “avoid” examples.
- Predefine exit triggers for each setup so any team member can manage if needed.
- Conduct 24-hour post-mortems on outsized wins/losses; extract one actionable change.
- If team conviction diverges, default to a smaller size and tighter stop until evidence resolves.
- Track process errors separately from market variance; only market losses are acceptable.
Drawdown Protocols: Automatic Brakes, Faster Recovery
The fastest way back to new highs is through smaller losses. Daniel uses tiered rules that auto-tighten risk when the account or strategy starts slipping.
- At −4% equity: cut risk per trade by 50% and limit to A setups only.
- At −7%: reduce exposure band by one notch, pause all ads, and shorten hold times.
- At −10%: 48-hour trading halt, full playbook review, and revalidation of RS and breadth models.
- No doubling down after a loss; recover with normal size and standard rules.
- Restore full risk only after two profitable weeks with 90%+ rule adherence.
Mistake-Proofing: Guardrails You Can’t Ignore
Humans slip; systems catch. Daniel bakes guardrails into the platform and workflow so the worst days remain survivable outliers.
- Platform hard limits: max daily loss, max number of trades, and enforced cooldowns.
- Pre-trade checklist—if two items fail (trend, RS, liquidity, stop distance), skip.
- Auto-alerts for RS deterioration and stop proximity to prevent “forgetting.”
- Maintain a “do-not-trade” list of historically negative-expectancy patterns.
- Reward rule-following in reviews, not raw P&L; process is the lever you can actually pull.
Size risk first: volatility-based positions that survive ugly markets
James Whelan doesn’t start with a ticker—he starts with the dollar risk he’s willing to lose and the current volatility of the instrument. Daniel Moss does the same, translating “how wrong can I be before I’m out?” into share size using ATR or similar range measures. When volatility expands, they automatically size down so one stop-out doesn’t nuke the day. When it contracts, they cautiously size up, but never beyond a fixed max risk per trade.
This keeps both James Whelan and Daniel Moss playing offense without forgetting defense, even when markets turn chaotic. They treat sizing as the first line of survival, not an afterthought, so drawdowns stay shallow and recoveries are faster. The result is a smoother equity curve, because position size breathes with the tape. With risk predefined and volatility respected, mistakes sting less, and good trades have room to run.
Trade the tape, not the story: mechanics over prediction every time
James Whelan treats narratives as background noise until price confirms the idea. He waits for actual triggers—breaks, retests, momentum thrusts—then acts, instead of guessing what a headline might do. If the chart contradicts the story twice in a row, he’s out and moves to the next high-probability opportunity. That discipline keeps him aligned with the market that exists, not the market he wishes for.
Daniel Moss works the same way: rules first, opinions last. He defines entries with specific levels, sets the stop where the setup is proven wrong, and trails winners only when structure supports it. If momentum fades or breadth deteriorates, he scales back regardless of how “good” the story sounds. Together, James Whelan and Daniel Moss show that consistent mechanics beat clever predictions, because rules execute while opinions hesitate.
Diversify by theme, instrument, and timeframe to blunt correlation shock.s
James Whelan spreads exposure across themes—like momentum, value tilt, or commodities—so a single narrative shift can’t hit every position at once. He prefers using ETFs alongside selected single names to separate stock-specific noise from macro trend risk. By mixing swing trades with slightly longer position holds, he avoids having all entries hinge on the same intraday rhythm. When cross-asset correlations spike, he pares back overlapping bets and keeps only the clearest leaders.
Daniel Moss applies the same logic with simple rules that force variety into the book. He won’t stack three trades that all live or die on the same factor, and he staggers entries so stops and targets don’t cluster. If a theme dominates performance for a week, he trims and rotates to prevent portfolio monoculture. Together, James Whelan and Daniel Moss prove that diversification isn’t owning “more”—it’s owning different, so one shock doesn’t become a portfolio-wide problem.
Define exits before entry: rules for adds, trims, and trailing sto.ps
James Whelan plans the exit before touching the buy button. He sets an invalidation level where the setup is proven wrong, not where it merely feels uncomfortable. Initial stop sits just beyothe nd structure or about 1–2 ATR, and he sizes so a hit is pre-budgeted. Profit-taking is staged: first payout at +1R, then let the rest run under a trailing structure stop.
Daniel Moss mirrors the approach with explicit rules for adds, trims, and trails that remove hesitation. He only adds after price moves in his favor and a pullback holds the breakout level, never into weakness. Trims happen on momentum stall or into obvious resistance, while the trailing stop tightens once open profit exceeds +2R. Both James Whelan and Daniel Moss cap give-back at roughly 40% of open gains and use time stops when a trade meanders. If three exits in a row come from rule violations, they pause that setup, audit the process, and lower the size until execution is clean.
Know your risk buckets: defined, undefined, and when to hedge
James Whelan separates trades into defined-risk and undefined-risk from the jump, so he knows exactly what can go wrong. If the payoff is undefined—like a naked directional equity position—he either shrinks size, sets a hard stop, or overlays protection. When he runs defined risk—collars, verticals, or tight structural stops—he’s comfortable pressing because the downside is boxed in. The point is clarity: every position gets labeled before it’s funded, so hedging isn’t guesswork under stress.
Daniel Moss uses the same buckets to decide whether to hedge the position or the portfolio. When correlation rises and the book skews one way, he prefers index puts to tidy up total beta rather than micro-hedging each line. If an individual’s name is stretched, he’ll write covered calls or roll stops tighter to defend gains. Both James Whelan and Daniel Moss keep a simple rule in play: when volatility lifts and edges compress, reduce undefined risk first, hedge second, and only then look for new defined-risk opportunities.
In the end, James Whelan and Daniel Moss keep the edge simple: protect capital first, let price confirm, and let process do the heavy lifting. When their momentum models say risk is rising, they’re comfortable stepping back and going defensive—holding cash, USD, or gold rather than forcing entries—because survival beats bravado during sloppy tape. They’ve spent years iterating on their systematic tools, but those signals are paired with human judgment; you don’t override the program without a rock-solid reason. It’s mechanics over prediction, with rules for when to lean in and when to get out of the way.
They also treat fit and communication as part of risk management. Mandates match the person—time horizon, tolerance, and objectives—formalized through questionnaires and a managed discretionary framework, then re-validated face-to-face so clients know the “why” behind positioning and drawdown handling. Finally, they strip out noise—literally removing distractions—so execution stays clean and the process gets the respect it deserves: get out of your own way, focus on what helps clients, and let the right decision emerge.
