The Best Trade I Ever Made Was the One I Walked Away From

The following is adapted from Money and Meaning by Christopher F. Poch.

For several years, I served on Citigroup’s Global Capital Commitment Committee—the group that determined which securities the firm would underwrite and release to the public. The stakes were high. If a deal went wrong, the firm’s reputation and finances were both on the line.

My job often had less to do with celebrating opportunities and more to do with identifying risks. One of my mentors, a lawyer who began his career in the “reorganization department,” taught me the value of spotting what wasn’t obvious. He looked for the proverbial dog who should have barked—the signals that others missed.

That mindset helped me and a colleague prevent two particularly toxic products—collateralized mortgage obligations (CMOs) and collateralized loan obligations (CLOs)—from being sold to individual investors at Citigroup Smith Barney. When the financial crisis hit in 2008, those securities inflicted massive losses on major institutions. But because we refused to approve them, our private clients were spared.

In the investment business, there is a saying: “The best trade you ever did was the one you never did.” In this case, it rang true. Saying no meant pushing back against the head of the Fixed Income Department—one of the most powerful executives at Citi. It carried career risk, but with the support of a strong boss providing “air cover,” I survived the inevitable criticism. More importantly, the decision saved clients from financial disaster.

Always Invert

When wealthy families lose their fortunes, it isn’t always due to extravagant spending. Often, the decline comes from repeated poor investment choices—risky businesses, speculative land deals, trophy projects like movies or Broadway plays, or ill-advised loans to relatives. Each mistake chips away at balance sheets until the damage becomes irreversible.

The lesson is simple: wealth isn’t just about what you invest in—it’s about what you avoid.

The Power of Patience

In my experience, many deals I initially passed on resurfaced later—at better prices and under more favorable terms. Waiting not only preserved capital but improved outcomes.

Ultimately, the key to staying wealthy isn’t chasing every opportunity. It’s having the clarity and discipline to walk away.

Sometimes the best advice can be summed up in three words: Just Say No.

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For more insights on disciplined investing and making smarter financial decisions, you can find Money and Meaning on Amazon.

Christopher F. Poch is the founder and CEO of Promethium Advisors, a wealth management firm serving family offices and high-net-worth individuals. As founder and head of Citi Private Wealth Management at Citigroup Smith Barney, Chris is recognized as a global leader in advising ultra-high-net-worth families. He has held senior positions at Bessemer Trust, the Private Bank, and Citibank’s International Private Bank. Over his four-decade career, he has received numerous industry awards and has been widely quoted in Barron’s and The Wall Street Journal. Chris is an avid basketball fan and involved in philanthropic activities with organizations that include Villanova University, the Society of the Sacred Heart, and the Order of Malta.