After more than 30 years on Wall Street, you’d expect someone managing billions of dollars to be exceptionally good at being right.

But perhaps the more valuable skill is knowing how to be wrong.

Every trader gets things wrong.

Your analysis can be excellent. Your research can be extensive. Your conviction can be strong.

And the market can still move against you.

So what happens next?

How do you know whether you’re early – or simply wrong?

When does conviction become stubbornness?

And when the evidence changes, how quickly should you be prepared to change your mind?

In this episode of Talking Trading, Louise Bedford sits down with Jay Hatfield, Founder, CEO and Portfolio Manager of Infrastructure Capital Advisors, to explore what decades at the highest levels of Wall Street have taught him about uncertainty, risk and getting things wrong.

Jay brings more than 30 years of investment experience, including roles at Morgan Stanley, CIBC/Oppenheimer, Zimmer Lucas Partners and SAC Capital, now Point72. Today, Infrastructure Capital manages more than $4 billion in assets.

But this isn’t a conversation about predicting where the market goes next.

It’s about what happens when your prediction doesn’t work.

Louise asks Jay about the most expensive mistakes of his career, how professional money managers respond after a series of poor decisions, and what changes psychologically when you’re responsible for billions of dollars rather than your own portfolio.

They also tackle one of the most seductive ideas in trading:

Conviction.

We’re constantly told that successful investors need conviction.

But conviction can keep you committed to a sound idea – or keep you trapped in a bad one long after the evidence has changed.

So how much conviction is useful?

And how much becomes dangerous?

After decades spent forecasting markets and the economy, Jay also reveals what investors spend far too much time paying attention to – and the investing belief he held 30 years ago that he would challenge today.

Because longevity in the markets isn’t about being right all the time.

It’s about knowing what to do when you’re not.

Questions for the Interview

1. Jay, you’ve spent more than 30 years on Wall Street. Are you better at being right now – or better at being wrong?
2. When you strongly believe in an investment, and the market keeps moving against you, how do you know whether you’re early, or simply wrong?
3. What’s the most expensive investing mistake you’ve made – and what did it change about the way you manage money?
4. When you have strong conviction in a position, and the market moves hard against you, what stops conviction from turning into stubbornness?
5. Retail traders are constantly told to have conviction. How much conviction is actually dangerous?
6. You’ve worked inside hedge funds and institutional markets. What do retail traders misunderstand about how professional money managers actually make decisions?
7. When you’re managing billions rather than your own portfolio, how does that change your relationship with risk?
8. What does a professional portfolio manager do after a run of poor decisions? Do you reduce risk, change the process, or keep executing?
9. You’ve spent decades forecasting markets and the economy. What do investors give far too much attention to that has surprisingly little value?
10. What is one investing belief you held 30 years ago that you would argue against today?

About Jay D Hatfield

Jay Hatfield is the Founder, CEO and Portfolio Manager of Infrastructure Capital Advisors, an investment management firm based in New York.

Jay has more than 30 years of experience across investment banking, hedge funds, research and portfolio management. His career has included Morgan Stanley, CIBC/Oppenheimer, Zimmer Lucas Partners and SAC Capital, now Point72. At SAC, he managed a $500 million infrastructure portfolio focused on credit instruments and infrastructure-related equities.

He also co-founded what became NYSE-listed NGL Energy Partners and today manages multiple ETFs and private funds through Infrastructure Capital Advisors. As of September 2026, Infrastructure Capital reported more than $4 billion in assets under management.

Jay holds an MBA from the Wharton School at the University of Pennsylvania and began his career as a CPA. He has appeared in or been quoted by financial media including Barron’s, The Wall Street Journal, Yahoo Finance and Bloomberg.

Stay in Touch with Jay

Infrastructure Capital Advisors: https://www.infracapfunds.com/
LinkedIn: linkedin.com/in/jay-hatfield-a189a314

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