Softbank CEO Masayoshi Son says he feels 'so stupid' for passing up early opportunities to invest in Tesla and Amazon

• Softbank CEO Masayoshi Son spoke at The New York Times' DealBook Conference on Tuesday.
• Softbank has invested in tech giants including Google, Amazon, and Microsoft.
• Son said he regrets previous chances to invest in Amazon and Tesla early on.

Softbank CEO Masayoshi Son is a big proponent of owning up to mistakes, and he acknowledged two of his biggest while speaking at The New York Times DealBook conference on Tuesday morning.

"I'm so stupid, don't embarrass me," Son said, putting his hand to his head after host Andrew Ross Sorkin mentioned that Son had a chance to invest with Jeff Bezos years ago. Without saying exactly when, Son said that years ago, before Amazon's IPO, he and Bezos talked one-on-one in a hotel for a few hours, and that they almost agreed on a deal. Son wanted to invest $100 million for 30% of the company, but he says Bezos disagreed and said Amazon was a $350 million company, not a $300 million company. The deal never went through, and Amazon is now valued at over $1.5 trillion. He might have learned from this mistake, though — Softbank has $102 million invested in Chinese e-commerce giant Alibaba.

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Son expressed similar regret over the missed opportunity to invest in Tesla.

"I bang my head" when thinking about it now, he told Sorkin. "If I had enough money and guts," he said,"if I were smart enough" he would have invested. Softbank does now have investments in Amazon and Tesla, along with other tech giants including Alphabet and Microsoft.

Masayoshi Son is the founder and CEO of Softbank and worth over $23 billion, according to Bloomberg's Billionaire Index.

Son admires the leaders of these tech firms, he told Sorkin. He mentioned respect for Jeff Bezos, Mark Zuckerberg, Elon Musk, Satya Nadella, and "all the other founders and CEOs," who he called "amazing leaders" of innovation.