Most people would be popping champagne after turning a $62 million investment into a slice of a $20.6 billion acquisition. Chamath Palihapitiya felt depressed instead.

The Paradox of Winning Big

Palihapitiya, best known for his SPAC investments in recent years, has been backing private companies for decades. One of his earliest bets was on Groq, an AI chip company that caught his attention in 2017. He invested $10 million that year, then another $52.3 million in 2018. Those investments gave him a major ownership position and a board seat.

When Nvidia Corp. (NVDA) announced it was buying Groq for $20.6 billion earlier this year, the math worked out beautifully for Palihapitiya. The deal validated everything he'd believed about the company. But his emotional response surprised even him.

"Felt incredibly down," Palihapitiya admitted during an appearance on "The Katie Miller Podcast." He told his wife, Nathalie Dompe, that he thought he might actually be depressed.

Her response? "You gotta just take the win here."

Always Looking at What Went Wrong

Here's the thing about Palihapitiya: while the internet was busy calculating his payday and celebrating the Groq acquisition, he was mentally cataloging everything that could have gone better. It's a pattern he's noticed throughout his career.

"I have felt the happiest before something great has happened," Palihapitiya explained on the podcast.

He recalled being an early investor in Facebook and feeling genuine happiness before the IPO. After it went public? The joy faded. Same story with the Golden State Warriors, where he's a minority owner. The anticipation before they won an NBA Championship felt better than the actual victory celebration.

The pattern repeats: Palihapitiya consistently feels worse after major wins than before them. It's the opposite of what you'd expect from someone who's built a career on spotting winners early.

This mindset might explain his relentless investment style. Instead of basking in victories, he's already thinking about the next opportunity or analyzing what didn't go perfectly. It's exhausting to think about, but it might be exactly what makes certain investors so successful at identifying the next big thing while others are still celebrating yesterday's wins.