Gregory Kennedy // Vibe Marketer

Dave: "Masa Son, welcome to the show. What's going on?"

Masa: "Dave, I sold my entire NVIDIA position."

Dave: "How much?"

Masa: "All 32.1 million shares. $5.8 billion."

Dave: "And why did you do that?"

Masa: "To go all-in on AI."

Dave: "You sold your NVIDIA stock... to invest in AI."

Masa: "Yes."

Dave: "NVIDIA makes the chips that run AI."

Masa: "Correct."

Dave: "So you sold the shovels to buy lottery tickets."

Masa: "I prefer to call them 'high-conviction bets.'"

Dave: "Got it. And this is your second time selling NVIDIA completely."

Masa: "That's right."

Dave: "In 2019, you sold $4 billion worth."

Masa: "Yes."

Dave: "Which would be worth $150 billion today."

Masa: "I'm aware."

Dave: "So you already missed out on $146 billion from the first sale."

Masa: "When you say it like that—"

Dave: "And now you're doing it again. To put $30 billion into OpenAI."

Masa: "And a $1 trillion AI manufacturing hub in Arizona."

Dave: "Right. Because WeWork worked out so well."

Masa: "That was a stain on my life, Dave."

Dave: "Cost you $11.5 billion in equity losses. Plus another $2.2 billion in debt."

Masa: "Adam and I fell in love."

Dave: "You fell in love with a guy who wanted to trademark the word 'We.'"

Masa: "He had vision."

Dave: "And before that, you lost $70 billion in the dot-com crash. The largest personal loss in history."

Masa: "But then I made it back with Alibaba."

Dave: "After a six-minute meeting."

Masa: "Jack Ma is very persuasive."

Dave: "So your entire investment strategy is falling in love during short meetings and then losing generational wealth."

Masa: "I believe in the singularity."

Dave: "Right. So just to recap: you've lost $70 billion, missed out on another $146 billion, burned $13.7 billion on WeWork, and now you're selling NVIDIA at what might be the worst possible time to bet it all on Sam Altman."

Masa: "Sometimes you have to push all your chips to the center of the table."

Dave: "You've done that four times and lost three of them."

Masa: "But that one Alibaba win though."

Dave: "Okay. Thanks for calling in."

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