The Yin and Yang of Successful Investing

Balancing Aggression and Defensive Caution

A successful investor has to be a person who can be aggressive and defensive.

You have to be able to bet.

But you also have to have enough fear to have the caution.

But you can't let fear control you.

- Ray Dalio, Bridgewater Associates

The great paradox of investing is that to be successful, you need two contrasting qualities that can seem at odds with each other - an aggressive mindset to go after compelling opportunities, but also a defensive mentality of prudent caution.

This delicate balance between aggression and defense is what separates the great investors from the merely good ones.

It's a yin and yang of sort - the aggressive "yang" energy to make bold moves when opportunities arise, combined with the defensive "yin" energy of safeguarding your capital through diligent risk management.

Master this balance, and you put yourself in the best position for consistent long-term success as a do-it-yourself investor.

The Aggressive Mindset: Making Your Bets

The first part of the Ray Dalio quote rightly states that you "have to be able to bet" as an investor.

The very nature of investing involves putting capital at risk in pursuit of future returns that can grow your wealth over time.

You can't just blindly play defense - you have to go on the offensive and make well-researched bets where you have an edge.

This aggressive mindset means actively seeking out investment opportunities where you have analyzed the prospects and determined the reward potential outweighs the risk involved.

  • It could be spotting an undervalued stock in a great growing industry.

  • Or forecasting that a sector like clean energy is going to boom and positioning your portfolio accordingly.

  • Or taking advantage of the next emerging investment trends such as weight loss drugs before they go fully mainstream.

The key point is that you can't just sit on the sidelines in fear.

Successful investors like Ray Dalio make their fortunes by being aggressive capitalists - studying trends and markets deeply, developing differentiated insights, and putting a lot of capital behind their highest-conviction ideas when the expected value seems highly skewed in their favor.

As a DIY investor, you'll need to adopt this mindset of continually looking for compelling investments where you have an edge based on your research and analysis.

Tune out the noise and stay rationally aggressive in making allocations that you deem attractive based on your own due diligence.

The Defensive Caution: Protecting Your Capital

Of course, that aggressiveness has to be balanced with defensive caution and prudent risk management.

This is the "fear" component mentioned in the Ray Dalio quote - the mindful respect of the ever-present risks in investing.

Successful investors must have this healthy fear of losing money that keeps their aggression in check.

After all, the greatest risk to growing your wealth over the long run isn't missing out on some great investment. It's suffering a permanent impairment of capital that leaves you with a lot less money to compound going forward.

That's why the best investors protect their capital base through diligent risk controls and careful position-sizing.

In practical terms, the defensive side of the equation means:

  • Doing thorough due diligence on any investment you make, always considering what could go wrong and what's being priced in.

  • Keeping cash on hand and diversifying your portfolio to limit concentration risks.

  • Implement stop-losses and hedging strategies to protect your capital from catastrophic losses should your investment thesis break down.

  • Relying on “margin of safety” principles when making investments - only putting capital at risk when the discount to conservative intrinsic value estimates seems compelling.

  • Limiting your overall portfolio risk capital to levels you can stomach without panicking and abandoning your strategy.

The best DIY investors maintain this defensive mindset discipline regardless of how high their conviction level is on a given investment.

They know there's no such thing as a "sure thing" and that hubris often leads to ruin. So they balance their aggressive mindset with ample caution, risk controls, and respect for the uncertainties inherent in investing.

Putting It Into Practice

The ultimate key is integrating these yin and yang forces into a cohesive investing mindset and process.

  • You can't just be aggressive and bet wildly without regard for risk.

  • And you can't be so defensive and paralyzed that you never put capital at risk to generate returns.

Rather, the most successful investors deftly fuse these two energies together into a unified flow.

They develop differentiated insights that give them the conviction to make focused bets in areas where they have an edge.

They put ample capital at risk to maximize their expected value.

But they also implement prudent risk controls, always considering what could go wrong, and never betting so big that a worst-case scenario could derail their overall portfolio or change their ability to continue playing the game.

Caution, not fear, guides their decisions on how aggressively to size each position.

From personal experience managing money for over three decades, the investors I've seen be the most successful tend to get this balance right through:

  • Developing either a rules-based investment process or deep fundamental analysis that incorporates checkpoints for analytical rigor but also disciplines around risk management and bet-sizing.

  • Knowing their own temperament well - how much volatility and drawdown they can truly stomach without deviating from their process. The best investors tune their strategy controls to their particular risk tolerance.

  • Maintaining the humility and self-awareness to know that the future is inherently unpredictable. No investment decision is ever made with 100% conviction or certainty. There's always a chance of being wrong or blindsided that needs to be accounted for.

  • Focusing more on capital preservation through diligent risk controls and defensive liquidity management rather than shooting for the maximum possible returns and risking a permanent impairment of capital.

  • Seeking out compelling asymmetric opportunities where the potential reward dwarfs the risk capital being put at risk if things go right. But sizing those bets prudently and managing the overall portfolio risk holistically.

  • Continuously stress-testing their own investing thesis and challenging their own assumptions and potential blind spots. Defensive caution means always questioning your own views and conclusions.

Juicy Bits

Successfully growing your wealth requires embodying what seems like a paradox on the surface.

  • You have to be boldly aggressive in making high-conviction bets in areas where you have an analytical edge and see compelling expected value.

  • But you also have to maintain a defensive mindset of caution, humility, and respect for risk.

Those who can integrate those two mindsets cohesively give themselves the best chance of compounding their capital relentlessly over decades.

It's a delicate dance of opposing forces that is imperative to master.

Because to succeed as an investor, quoting from the great words of Ray Dalio, "You have to be able to bet. But you also have to have enough fear to have caution. But you can't let fear control you."

Getting this balance right is the key to long-term investment success.

Asset Allocation Performance Review

Source: iShares, 5/28/2024

High-Level Observations:

  • All asset allocation portfolios we monitor are up year-to-date with higher-risk portfolios exhibiting commensurate higher returns.

  • Conservative portfolios with a heavier allocation to bonds are still recovering from the rise in interest rates starting in 2022.

  • Over the last three years, the GF Low-Risk strategy is only up 1.0% on an annualized basis (before fees and transaction costs). Going back 5 years the annualized performance improves to 4.9%.

  • Equity-heavy allocations have outperformed more conservative allocations thanks largely to the performance of US large-cap equities.

  • The GF High-Risk strategy is up 3.0% on an annualized pre-cost basis over the last three years. Over the last 5 years, the strategy is up a respectable 8.4%.

  • Year to date, commodities have provided a nice boost. A big reason is higher oil prices. Most recently, precious metal prices have joined the party providing a further boost.

  • Over the last week, Commodities and Cash have been the only asset classes with positive returns. The worst is Real Estate.

  • The investment environment remains in the Exuberant Zone.

Source: iShares, 5/28/2024

Weekly Performance Attribution

Subtracted Value

  • Real Estate (-3.5%)

  • US Small Cap (-1.7%)

Added Value

  • Commodities (0.4%)

Long-Term Asset Allocation Portfolio Characteristics

Expected Returns: Expect slightly lower than normal equity and bond market returns given valuation conditions

Source: Global Focus Capital LLC

Risk: Diversify with alternative assets, market volatility has been significantly below historical measures

Source: Global Focus Capital LLC

Equity Risk: Asset allocation portfolios are dominated by equity market risk, no different from the past.

Source: Global Focus Capital LLC

A Bit of Wisdom Never Hurts

Goals determine what you’re going to be.

- Julius Erving

Disclaimer: This newsletter is not trading or investment advice but for general informational purposes only. This newsletter represents my personal opinions which I am sharing publicly as my blog. Futures, stocks, and bonds trading of any kind involve a lot of risk. No guarantee of any profit whatsoever is made. You may lose everything you have. We guarantee no profit whatsoever, You assume the entire cost and risk of any trading or investing activities you choose to undertake. You are solely responsible for making your own investment decisions. Owners/authors of this newsletter, its representatives, its principals, its moderators, and its members, are NOT registered as securities broker-dealers or investment advisors either with the U.S. Securities and Exchange Commission, CFTC, or with any other securities/regulatory authority. Consult with a registered investment advisor, broker-dealer, and/or financial advisor. By reading and using this newsletter or any of my publications, you are agreeing to these terms. Any screenshots used here are the courtesy of Global Focus Capital and Retirement With Possibilities. The data, quotes, and information used in this blog are from publicly available sources and could be outdated or outright wrong - I do not guarantee the accuracy of this information.

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