The Ledger, every show

“I think there were some small mistakes made, but they were company-wide. They were under all departments, not just his. Everyone knew about it. They weren't ethical mistakes, and he sort of, you know, took the fall.”

“Yeah, I think we wanted to be somewhat involved with it, and there were a lot of amazing founders building in it, and they're gonna build great things, but they're not gonna get us great VC returns.”

“I fully believe if they're like, hey, Sequoia led our seed, and I'm like, hey, are they doing your A, and they're like, Well, they're doing their pro rata. I'm like, this is not a good company. Like, objectively is not a good company.”

“Don't care about the product, don't care about anything, just go work at the fastest growing company because winning feels great.”

“I don't know if they're fucked up cultures, but I don't think they're incentivized to have the best returns. If you're an associate at a firm, and you're maybe there for five or six years, your job is to get a deal done that's gonna get marked up quickly so yo…”

“I'm clearly gonna Lose the deals that I want to lose, and if I win them, it's probably not the ones that I want.”

“Of the first 40 of them, only one person had two lead checks, and that was Andreessen, and no one else had two, and if you look through the smattering, there are, you know, Green Oaks is in there, a lot of Gill's in there, but there's a lot of other random peo…”

“Like, not to be on the AI hype train, but I do think we are going to have a lot of exits Eight years from now, around the hundred billion dollar mark.”

“And founders don't care if you did a 25 K check or a million dollar check at the seed. They just think that you've invested in the best companies.”

“I was fortunate enough to have data from the earlier funds to say, we've absolutely crushed it, and we're now at like about four X DPI. I think we can get to five or six, and we knocked it out of the park.”

“So I think a lot of the times that I've learned is like, hey, model in the pro rata, but you're only gonna get 70 or 80% of it.”

“I think it's really hard if you get Sequoia to offer you money and be on your cap table and have that amazing brand halo effect to not take it, and I think someone always should.”

“There's now like hundreds of billions of capital chasing slightly more companies. I think the experiment we're going through right now and went through in 2020 is like, hey, if we put 10 times as much capital into the market, there better be 10 times as much g…”

“If you have, like, the naivety to think you're gonna build something that's really close to what OpenAI is building, And they're not going to build it. You're crazy. Like, you know what I mean? So I think we've really stayed away from things that OpenAI will e…”

“Yeah, we have to compete with them, we have to do better than them, there's not room for all of us, and Frankly, I kind of think, Harry, you were younger when you started, so you might have a little more time. I got, like, 15 years of this until I'm really goo…”

“It might not have hurt to sell Gusto. I think Gusto's a great business, but I think, you know, they were valued at ten billion at one point, and I think they're still gonna be a strong business. I don't know if they're gonna have explosive growth from there.”

“Keith Raboy. I mean, whatever people want to say about him, I think he's extremely smart.”

“He's crazy, but he's the best salesperson and the best product person that I've ever met in my life.”

“The founder needs to have intuition of what they want. The customers aren't going to know.”

“So I, you know, I left after doing three funds with some combination of Sam and Jack to build out my own firm just for ego and pride, to be completely honest.”

“It was about nine billion when the lockup ended. That was tough. I think the market cap's about thirty-nine billion now. I think it's pretty public. The fund owned just about seven percent. You can do the math. That's about maybe two billion of gains that coul…”

“Maybe, maybe the worst decision related to tech that this administration has had. Like, first off, why would you not want an amazing engineer immigrating to your country? Just like, straight up, we want all of the best, smartest people going to work in our cou…”

“I don't want to put him in a weird position where he's leaking anything. It just, it doesn't seem like good for OpenAI, and it doesn't feel good. Like, I kind of want, and you might say this is stupid, to like, earn this on my own right.”

“I think it's really challenging to be like a seven hundred million dollar fund. Now I think you're either a really massive, powerful platform like an Andreessen or a GC Or you just have the legacy cachet, like a Sequoia or a Kleiner, or you have to be a boutiq…”

“I think that it is, people say it's this sort of chummy, like, collaborative thing where we're all kumbaya and having fun, and then, like, You know, you get to it, and someone just, like, elbows you out of the way. It's not. It's a competitive market. We're al…”

“There are still some. There are less. I think when I got there in San Francisco in 2013, it looked a little more like a small, smaller town, maybe Austin or St. Louis, where everyone really trusted everybody. And had deep connection, and naturally it's grown. …”

“You know, I think we had about 17 unicorns across the fund, because it's just a small world, and everyone's coming by, so I'm like, oh, these are the founders of Instacart, or Reddit, or Rippling, or Boom, and it's like, this is the bar.”

“It was give money to the best people. You know, we did Reddit at a higher valuation. We did rippling at 25.”

“Yeah, and I do believe that the majority of the best companies are going to be built from San Francisco, but the people need to be a little bit outward looking in what they're building, because Your market better be the entire United States at a minimum to be …”

“Yeah, I believe that, and I think, yeah, moving forward, it's just gonna be call your anchor LPs and say, let's talk through how we want to handle the situation.”

“People do these wonky things where they're like, we raised five from this person, and we have this thing soft-circled, and then you get to your lead, and they're like, there's only room for us to do under half of this deal. We're out. And I'm like, don't do th…”

“Rippling and Reddit. We sold a little bit of rippling on the way up, just because, like, our LPs wanted money and, you know.”

“We look much more like a hedge fund or PE world than we do VC from 10 years ago.”