The Big Mistake Nobody Admits: When to Sell, When to Hold, and Why Most Investors Get It Wrong

Premieres Monday December 29 at 6:00 a.m ET Why Most Investors Sell at the Worst Possible Time 👇

Most investors believe the hardest part of investing is knowing what to buy, but this interview makes a compelling case that knowing when to sell is where fortunes are actually made or destroyed. Wealthspire Managing Director Justin deTray explains that the biggest threats to long-term returns are behavioral, not analytical—panic selling during market stress, rushing to cash when volatility spikes, or abandoning a well-constructed plan because headlines feel overwhelming. He walks through why investors who sell when markets “feel unsafe” often lock in losses they can never recover from, even if markets later rebound sharply .

The discussion digs deeper into the psychological mistakes that repeatedly sabotage portfolios: loss aversion that keeps investors holding broken positions too long, recency bias that convinces them recent winners will keep winning forever, and overconfidence that peaks after markets have already run. DeTray emphasizes that successful investing is not about predicting the next move, but about building portfolios investors can actually stick with through downturns. The uncomfortable truth, he argues, is that most people don’t underperform because markets are unpredictable, they underperform because they sell at the worst possible times and chase returns when risk is highest, quietly compounding bad decisions over decades .

We break down 👇

🔹 Why behavior matters more than asset allocation

🔹 How investors sabotage returns during market volatility

🔹 The hidden risks in private credit and alternative investments

🔹 Whether AI is actually a bubble — or just misunderstood 🤖

🔹 Why chasing returns after good years usually ends badly

🔹 How smart investors think about corrections, fear, and opportunity