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Rampell: Haggled over $5M on Plaid's Series B, later invested at $2.4B

Alex Rampell · Alex Rampell: The Best Founders Materialise Capital, Customers & Labour | The Future of Venture · 20VC with Harry Stebbings · Jan 12, 2026 · at 1:12:23

Alex Rampell, General Partner at Andreessen Horowitz, recounts his biggest investment mistake when negotiating with Plaid founder Zach Perret.

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“It probably was one of the first rounds of Plaid, which I subsequently corrected myself for by doing the Series C of Plaid. So I think we invested at 2.4 billion for the Series C, and I was debating a five million dollar difference with Zach for the Series B. I think I wanted to do it at one 30, he wanted one 35, and I think Goldman was willing to pay 200, but he was willing to work with me because of You know, my FinTech, and it's like, no, no, no, fine. Like, that was just so stupid, right? And luckily, I was willing to admit that I was stupid and did the next round, but you can see the difference on this is why it's so important to do two things, to correct yourself if you're wrong and not be proud about it, but also if you really believe that this can be a huge company, and I was burdened by what has been, to quote the great Kamala Harris, of you know, oh, wow, Yodaly, which had predated Plaid, that, Went public and had a terminal valuation of six hundred million dollars. So like, of course, this like one 30 versus one 35 or whatever the hell we were talking about was very material, but it was so stupid.”

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