Your Brain Is Costing You Money | with Dan Pascone and Justin Detray | EP #51

Justin Detray's path into wealth management runs through a proprietary trading desk, not a financial planning classroom. He studied astrophysics in graduate school in New York City, then took time off from a PhD program in 1998 to become a proprietary trader on Wall Street. He traded professionally for 14 years, running his own prop shop, before moving to California and switching into wealth management about 13 years ago.

That background shapes how he works today. As a managing director at Wealthspire Advisors with around 130 clients, Justin still does his own market research and trades for himself, not because long-term investors need to watch the market daily, but because it keeps him close to what's actually driving client anxiety when they pick up the phone.

The first bias Justin flags is recency bias: the instinct to assume that whatever the market has done recently is what it's going to keep doing. Three good years in a row feels like evidence of a trend, not a coincidence, and that assumption can push investors toward overconfidence near a peak and panic near a bottom. Our piece on fear versus greed and how to stop sabotaging your own investments goes deeper on this exact pattern.

The second bias is anchoring, and Justin's example makes it concrete: a stock was at $35, it's now at $10, so surely it has to go back to $35. It doesn't. The market has no memory of where a stock used to trade and no obligation to return there. A cleaner question than "will it get back to my old price" is simply, "knowing what I know today, would I buy this at today's price and today's risk?" The Motley Fool's breakdown of anchoring bias covers the same mechanism in more detail.

Justin's take on the information age cuts against the common assumption that more data leads to better decisions. In his view, more information mostly leads to more decisions, fast, reactive, type-one thinking rather than the slower, deliberate type-two thinking that good investing actually requires. Twenty years ago, acting on a bad impulse meant calling a broker who might talk you off the ledge. Today it means tapping a phone and liquidating a portfolio in seconds, with no friction and no one to talk you down.

Justin's coaching process starts before the phone even rings. He keeps a general sense of what's dominating the news cycle so he isn't caught flat-footed, but he's deliberate about not assuming what's actually bothering a specific client. He asks, and he listens, without jargon, and without inserting his own bias into what he thinks the concern should be. The goal is to take whatever's worrying a client today and connect it explicitly to their actual long-term plan, since most headline-driven fears don't change a 10, 20, or 30-year time horizon even when they feel urgent in the moment.

Here's the pattern Justin sees most often in his most successful clients: the same instincts that built their careers work against them as investors. Running a business rewards decisive, controlling action. But reacting to news with a portfolio change usually means reacting to something the market has already priced in, and the odds are stacked against you outguessing it. Our control-first playbook for reducing financial stress covers a related idea: the control that actually helps is control over your process and plan, not control over the market's next move.

Justin's own investing history is the clearest illustration of what he's describing. He read Jeremy Siegel's Stocks for the Long Run around 2000 or 2001, early in his trading career, and it reshaped how he thought about markets. He and his wife have stayed invested in equities the entire time since, roughly 26 to 27 years now. They've never gone to cash and never panicked, through multiple bubbles and multiple crashes. As Justin puts it, compounding growth really does work, but it takes time and discipline, and it requires controlling the behavioral impulses that can derail you in both directions.

One of Justin's more surprising observations cuts the other way: many of his successful, high-net-worth clients don't intuitively grasp what compounding growth actually does over decades. As a result, some of them underspend today and end up, in his words, with more money at the end of their life than they ever meant to have. His question to clients is direct: if you're 92 years old with that amount of money, is that really what you meant to have? His advice is to do the gifting and charitable giving now, while you're alive to see the impact, instead of waiting until the end. Our piece on financial minimalism for high-complexity wealth looks at a similar idea: more isn't automatically the goal once your plan is actually funded.

This episode is for high-earning professionals and executives who are used to controlling outcomes at work and are tempted to manage their portfolio the same way, especially when markets get volatile and the headlines get loud. If you've ever caught yourself about to make a portfolio move because of something you read that morning, this conversation is built to slow that impulse down.

If you've ever caught yourself about to make a portfolio move because of a headline, a hot streak, or a stock that just won't go back to its old price, that's exactly the kind of decision a Free Wealth Strategy Call is built to pressure-test. We'll walk through your actual plan together, so the next time markets get loud, you already know what to do instead of guessing under pressure. You can also find more conversations like this one on our Making Sense of Your Money hub.