Investment Philosophy

Bootpack (noun) /BOOT•pak/: “A steep, demanding path requiring preparation, skill and grit that leads to unparalleled views, abundant terrain and epic trails beyond.”

 
 

Bootpack’s core investment principles are built upon our nearly two decades of managing institutional capital.

 

Our hands-on experience navigating multiple economic cycles imparted invaluable lessons on the investment strategies and philosophies that stand the test of time.

These principles are the compass that guides us through the complexities of the market as we steward our client’s wealth.

 

We believe:

Taxes are the single largest expense most investors never fully account for. Investment returns get the headlines; tax drag quietly erodes them. A disciplined focus on tax efficiency — through asset location, tax-loss harvesting, direct indexing, and structuring — can add more to long-term wealth than chasing an extra percent of return.

The best investment strategy is the one you'll stick with through up and down markets. Understanding what you own, why you own it, and the realistic range of drawdowns you may face is what keeps you from selling at exactly the wrong time. Markets will decline. The investors who benefit most are the ones who are prepared for it in advance.

Asset allocation — how your portfolio is divided across stocks, bonds, cash, and alternative assets — is the most important decision in long-term investing. Country, sector, and manager selection matter, but they are secondary. The discipline to stay invested across full market cycles is what drives outcomes over time.

Global diversification is one of the few genuine free lunches in investing. Markets around the world consistently rotate in leadership with little predictability. Holding a broadly diversified global portfolio reduces dependence on any single economy or market cycle — and captures growth wherever it emerges.

Attempting to consistently beat “The Market” though fundamental stock-picking is a extremely challenging. This applies to both amateurs and professionals. The vast majority of active managers (“stock-pickers”) underperform their benchmark, particularly in a taxable accounts (see Source #1).

For patient investors, systematic exposure to certain return factors — such as value, quality, and low volatility — has historically provided a reasonable edge over market-cap-weighted indexes over long horizons. This is not a guarantee, but it is a disciplined approach grounded in evidence rather than narrative. (see Source #2).

Market timing is a losing game. Missing just a handful of the best trading days in any given year — often clustered right after sharp declines — can devastate long-term returns. The cost of trying to sidestep short-term volatility is almost always higher than the volatility itself. To earn the highest return, you must remain invested through good times and bad (See Source #3).

Equities remain one of the most reliable vehicles for growing real wealth (after inflation) over time. For investors with long time horizons and confidence in long-term economic growth and human ingenuity, a meaningful allocation to global equities belongs at the core of most portfolios.

Alternative investments — private equity, hedge funds, venture capital, and other strategies — can meaningfully improve a portfolio's risk-adjusted returns when selected rigorously. Most alternative managers do not clear that bar. The ones that do are often difficult to access. Manager selection and due diligence are not incidental to this process — they are the entire job.

Financial media is engineered to create anxiety. Fear drives engagement. A steady stream of urgent headlines is not investment advice — it is a business model. Tune it out. Your portfolio's long-term trajectory is built on structure and discipline, not reactions to the news cycle.

Compounding your money is akin to bootpacking - simple in theory, very challenging in practice. Long-term wealth creation is achieved through careful planning, disciplined management, and above all else, steadfast patience throughout the journey.

 

Sources:

(1) https://www.spglobal.com/spdji/en/research-insights/spiva/

(2) https://www.dimensional.com/us-en/insights/when-its-value-versus-growth-history-is-on-values-side

(3) https://www.dimensional.com/us-en/insights/what-happens-when-you-fail-at-market-timing

  • "Investing should be more like watching paint dry or watching grass grow. If you want excitement, take $800 and go to Las Vegas."

    Paul Samuelson (Nobel Laurate, Economist, Presidential Advisor)

  • “Compounding doesn’t rely on earning big returns. Merely good returns sustained uninterrupted for the longest period of time – especially in times of chaos and havoc – will always win.”

    Morgan Housel (Author)

  • “The function of economic forecasting is to make astrology look respectable.”

    John Kenneth Galbraith (Economist, Advisor to JFK)

  • “People often complain that the stock market is a rigged game. And so it is. It's rigged against the impatient – and in favor of those who can let their winners run. The longer you can let them run, the more rigged a game you get to play.”

    Jason Zweig, (WSJ Columnist)

  • “The idea that a bell rings to signal when to get into or out of the stock market is simply not credible. After nearly fifty years in this business, I don’t know anybody who has done it successfully and consistently. I don’t even know anybody who knows anybody who has.”

    Jack Bogle (Founder of the Vanguard Group)

  • “Ultimately, nothing should be more important to investors than the ability to sleep soundly at night.”

    Seth Klarman (Legendary Investor)

  • “Your personal experiences with money make up maybe 0.00000001% of what’s happened in the world, but maybe 80% of how you think the world works.”

    Morgan Housel (Author)