Dharmesh Shah missed early Dropbox investment due to mutual friendship hesitations
Dharmesh Shah · HubSpot Founder Dharmesh Shah: The Ultimate Guide to Company Culture | E896 · 20VC with Harry Stebbings · Jun 13, 2022 · at 1:14:55
Dharmesh Shah, co-founder and CTO of HubSpot, shares his biggest angel investing miss, revealing why he did not participate in Dropbox's initial funding round despite knowing Drew Houston before Dropbox started.
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“Dropbox was one, and it was a weird story. And it was a miss because Drew and I were already friends. I knew him before he started Dropbox. Talked to him out of the prior startup he was going to do. We would meet regularly. He's another MIT guy. And it was a miss because He thought me too much of a friend to ask and I thought him too much of a friend to offer. And so I never, and then I was much years later. That's like, wow, that was stupid. Can I invest? I was like and so I did. And a couple of investments that got acquired by Dropbox. So I ended up having you know, pre IPO shares, but I was not in that first round.”
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