To The Moon

$S&P 500(.SPX)$

A Deep Dive into Building a Strategy That Aligns With Your Goals, Psychology, and Market Philosophy

In the world of investing, everyone starts off looking for “the best strategy.” We read the classics: The Intelligent Investor, Common Stocks and Uncommon Profits, One Up on Wall Street. We consume Buffett’s annual letters, study Ray Dalio’s frameworks, and tinker with spreadsheets, backtests, and screeners. We chase momentum, then pivot to value. We buy the dip, only to sell in panic. We follow Reddit, CNBC, and Substack. And eventually, through trial, error, and reflection, we arrive at a simple but powerful realization:

You need a strategy that fits you — not someone else.

Your investment playbook must align with your temperament, your time horizon, your view of risk, and how you process uncertainty. It must not only make sense on paper, but feel right — giving you the confidence to act in chaos and the discipline to sit still in noise.

So after a decade of studying markets, testing strategies, watching booms and busts unfold, and managing money in both calm and crisis — I’ve built an investment playbook that reflects my core beliefs. It’s not perfect, and it continues to evolve. But it has helped me stay grounded, make rational decisions, and steadily build wealth.

Let me walk you through what this playbook looks like in detail — from the philosophical foundation to the tactical execution, including real-world applications and key lessons learned.

Core Philosophy: Quality, Durability, and Discipline

At the heart of my approach lies a commitment to owning high-quality businesses for the long term, while maintaining enough macro awareness and valuation sensitivity to avoid being blindsided by economic shifts or excessive optimism.

I’m not a pure value investor in the Graham sense — hunting net-nets or low P/B stocks with crumbling businesses. Nor am I a pure growth investor chasing the next hot software IPO or biotech moonshot. I’m somewhere in the middle — what I’d call a QARP investor: Quality At a Reasonable Price.

This means I look for businesses that:

• Have moats — durable competitive advantages, whether brand, scale, IP, or network effects

• Generate consistent free cash flow across cycles

• Are led by competent, aligned management teams with a history of capital discipline

• Possess clean balance sheets, low financial leverage, and flexibility in downturns

• Are reasonably valued, ideally below intrinsic value but never at absurd premiums

I’m looking to buy and hold these companies for 5 to 10 years, letting compounding do the heavy lifting. These are the “forever” stocks — the kind of companies you can tuck away and revisit after a decade with minimal regret.

Examples:

• ASML, due to its monopoly-like position in EUV lithography

• Visa/Mastercard, thanks to their global payment rails and network effect

• Thermo Fisher, for its entrenched position in life sciences and research

• Nvidia, especially when it wasn’t fully appreciated as the AI infrastructure layer

Tactical Layer: Contrarian Cyclicals and Deep Value

While quality compounders form my core, I dedicate about 20%–30% of my portfolio to opportunistic or cyclical bets. These are sectors or stocks that are:

• Deeply out of favor due to macro trends

• Trading at distressed valuations despite stable fundamentals

• Oversold due to sentiment, liquidity crunches, or temporary industry headwinds

These opportunities emerge during moments of fear and pessimism — where the crowd is panicking, and the fundamentals are misunderstood. I use this sleeve of my playbook to deploy capital into:

• Energy (e.g., oil majors in 2020)

• Real estate and REITs (e.g., late 2023)

• Defense and industrials, when overlooked

• Financials, during credit panics or yield curve inversions

The goal here is not to marry these names forever, but to extract value over 1–3 year periods where reversion to mean or macro shifts can drive strong returns.

I use screeners based on:

• EV/EBITDA < 6x

• P/B < 1x (with improving ROE)

• High FCF yields

• Insider buying and/or activist involvement

These are the stocks I buy when CNBC is telling you to sell. And they often deliver the highest short-term returns, especially when paired with patience.

Macro Awareness: The Invisible Hand Behind Market Moves

One of the biggest edges in today’s market — especially in the post-2020 world — is recognizing the primacy of liquidity. While valuation, fundamentals, and sentiment matter, global liquidity flows and interest rate regimes often dictate market direction in the short and medium term.

That’s why my playbook includes a strong macro overlay. I’m not timing markets, but I’m highly attentive to:

• Federal Reserve policy, particularly the rate of change in interest rates and balance sheet activity

• Real interest rates, which impact equity valuations

• Credit conditions, including yield curves, junk bond spreads, and bank lending standards

• Fiscal policy, government deficits, and geopolitical cycles

• Global dollar liquidity, which affects emerging markets and commodity cycles

For example:

• I reduced growth exposure in late 2021 as the Fed pivoted hawkish

• I built up cash in 2022 as QT began and the 10Y-2Y curve inverted

• I leaned into REITs and small caps in Q4 2023 as disinflation took hold and rate cuts became priced in

Macro is not a trading signal — it’s context. It helps me determine how much risk I’m taking and where I’m deploying capital.

Valuation Frameworks: Flexible, But Focused

No investment playbook is complete without a valuation compass. But I don’t believe in rigid models. Each asset type requires a different lens.

Here’s how I approach it:

More important than the model is the margin of safety. I don’t buy “cheap” companies with deteriorating businesses. I buy good companies at fair or undervalued prices, ideally when the crowd is distracted.

I also pay attention to capital allocation metrics:

• ROIC and ROE vs WACC

• Buyback efficiency (repurchasing at good prices)

• Dividend coverage and sustainability

• Historical vs forward valuation multiples

The Behavioral Layer: Protecting Against Yourself

Even the best strategies fail if the investor can’t execute. So I’ve added a behavioral safeguard layer to my playbook.

Here’s what I do to stay disciplined:

• Maintain a “watchlist with price alerts” instead of chasing

• Pre-write “buy the fear” scripts to combat hesitation in market crashes

• Use position sizing limits to avoid overexposure

• Set trimming rules when positions exceed a certain % of portfolio

• Keep journals of past mistakes and misjudgments

• Hold 10–15% cash as optionality when markets are euphoric

Investing is as much about temperament as intelligence. In fact, as Charlie Munger once said:

“The big money is not in the buying or the selling, but in the waiting.”

Real-World Applications: My Playbook in Action

Here’s how this investment strategy has played out in recent market cycles:

🔹 2020: COVID Crash and Recovery

• Loaded up on energy stocks (Chevron, Devon), REITs (SPG, WPC), and airlines (DAL) in March–April

• Rode the V-shaped recovery with high-conviction holds

🔹 2021: Peak Euphoria

• Sold overvalued tech names and SPACs, avoided NFTs and meme stocks

• Rotated into value, defense, and financials

🔹 2022: Bear Market

• Added to cash, avoided most tech carnage

• Bought high-dividend industrials and defense stocks

• Prepared for rate cuts and disinflation

🔹 2023: Bottom Fishing and Rotation

• Focused on REITs, utilities, and small caps (trading below book)

• Opened gold miners as inflation hedge

• Trimmed winners in December rally

🔹 2025: AI Boom and Selective Profit-Taking

• Trimmed Nvidia and other AI leaders at elevated valuations

• Watching for second-order beneficiaries of AI infrastructure (data centers, cooling, semicap)

• Monitoring Fed liquidity, inflation reacceleration, and commodities

Final Thoughts: Choose Your Own Adventure

At the end of the day, my investment playbook is tailored to my worldview, goals, and temperament. It’s not meant to be a universal blueprint — but a structured process that lets me make decisions calmly, consistently, and rationally.

Your playbook may look different. Maybe you’re a dividend investor. Maybe you love high-growth SaaS. Maybe you swing trade technical setups. All are valid — if they suit you.

What matters is that you:

• Build a system you understand and believe in

• Stay flexible, but never emotional

• Invest in alignment with your goals and risk profile

Because in the end, markets will fluctuate. Strategies will evolve. But your discipline — and your ability to stick to a well-designed playbook — will determine your long-term success.

Disclaimer: I want to make it clear that I am not a financial advisor, and nothing I say is intended to be a recommendation to buy or sell any financial instrument. Additionally, it's important to remember that there are no guarantees or certainties in trading or investing, and you should never invest money that you can't afford to lose.

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