YouSaid · the spoken record

Alex Rampell

lines on the record: 68
first: 2026-01-12
most recent: 2026-01-12
sittings or episodes: 1
sources: podcast

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“It ends up eating even more of the world. This is kind of going back to Marx's essay around software eats the world. That largely has happened, as I mentioned, like the five biggest companies on Earth, they're technology companies, which was unthinkable in 2005. Like technology companies were a little service providers to big companies like banks and oil companies, right? I think this momentum of kind of everything becomes a software company. It kind of goes into this like thesis too that I mentioned around software does the job of labor, you're going to have all of these areas where it's like there's going to be like vertical SAS proved this or kind of V1. It's like, oh, how is Toast worth $20 billion? You're going to have a lot of things like this where it's like brand new markets that have grown like crazy. AI is now allowing software and technology to do so many things that it didn't do before. And this is before even things like robotics. Like if robots actually work, wow, like now you've expanded the market like another hundred X. I'm just so bullish on the ability.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“So it probably was one of the first rounds of PLAD, 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 $5 million difference with Zach for the Series B. I wanted to do it at $130. He wanted 135. And I think Goldman was willing to pay $200, but he was willing to work with me because of my fid tech. And it's like, no, no, 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 Camel Harris, of, oh, wow, Yodeli, which had predated Plaid, that went public and had a terminal valuation of $600 million. So, of course, this $130.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“It's all about founder. I mean, you have to, again, it converges on reality at some point in time. Like, there's going to be a public company. You can't, like, tell everybody in the order book of the IPO that's undersubscribed. Like, no, no, no, the founder's really good. Like, yes, of course it has to converge on reality. But I think it's like, it is like materialized labor capital customers. That's kind of it for me with the right motivation, which is the Count of Monte Cristo.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Think it really is find high agency people that know the history of the space that can materialize labor capital and customers that are the catabata crysto and don't second guess anything. Give them money, be their best partner and go versus question the market, question the this. I think it really is. I've just become 100% convinced this is entirely about people. 100% at every round, by the way, it could be a D round, it could be an E round, it could be an A round, it could be a seed round.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Something around credit for a lot of our companies. So, you know, we have equity products, but we don't have debt products. And they have very different return profiles, obviously. But every one of our companies, they need, you know, General Catalyst actually has one of these. They have a credit fund. So either for customer acquisition or if you're fintech and doing lending. So that would be interesting. But in general, we just kind of, we listen. We don't want to be at odds with our entrepreneurs. Like there's a very solid reason why we don't have that, which is like, oh, you didn't pay back the bill. I need to go foreclose. Like that's a venture capital firm, like you can earn a thousand X on a winner. You don't really want to kind of beat up the companies that are struggling. And that's kind of what the credit instrument needs to do. But I think it's a good product.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“I've probably changed my mind. Well, as I mentioned, you have to be able to change. Like, it's more of companies where we didn't do like the early round. And then it's like, I'd rather be rich than right. That's what we often talk about. It's like, all right, I want to be right. So we've probably done a couple deals where it's like we passed, you know, around n minus one, we end up doing right.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Guy or gal. And like the woman that was running wealth, she was like, she stood up in the audience, like, yeah, yeah, yeah. But it's true. It's like if you have a high EQ and you're good at playing golf with people, like you're going to start hiring more people like that because that's how you get more customers. And you kind of sometimes there will be an opportunity. The upskilling is not like, hey, everybody should learn how to code. The upskilling might be like, stop doing tedious work, like answering, you know, like looking at knowledge base and then, you know, typing that back with lots of typos into the email response in Zendesk, but actually start going into like, you know, send customer flowers. Like, do get to know that customer really well. Go visit them at their whatever for the high value customers that you just couldn't do before.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Center. You should love your customer and make them love you. There's the story that he would tell around there's somebody who had something really bad happen and was on the phone with a customer support person. I think her husband died something bad that had nothing to do with the shoe order. Zappo sends that guy or that woman flowers. Doing things like that, making your customer love you is something that you can now focus on once you take away the cost center element of something like this. Or if I'm a law firm, again, I agree with you. Like you probably don't need people doing this tedious work and the number of people doing the tedious work will fall off a cliff. No disagreement. But I would not be surprised to see smart companies start reallocating them. Like I actually gave a, I gave a talk to the exec team at JP Morgan about this, right? They're like, what part of our business is going to be least touched by AI? And I said, you know what? Wealth management. Because what is wealth management? It's, yeah, yeah. It's like hopefully like getting good returns for the dollars that you have with us. But it's really like that relationship.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't disagree with that. I'm saying it's not like that's why I kind of gave the example of the three types of SAS, right? It's like you're going to have some totally impervious. And I'm talking about SAS, not people. If you flip that to people, it's like, all right, the users of Zendesk are probably going to go away. Therefore, that labor market might get decimated. 100% agreed. On the other hand, it's like, if I'm United Airlines and now I don't need as many customer support people because now every answer kind of auto answers itself with AI, well, you know what? I should probably take care of my best travelers better and give them like a personal human that will be really nice to them and remember their birthday and then they're going to buy more first class tickets for me. I might reallocate some of that labor to other things because I'm making more money and I no longer have this cost. I mean Tony Shea, who sadly departed who ran Zappos, you know, he had this whole thing, which I think is actually correct, which is I'm going to turn. Most people think of customer support as a cost center. They should think about it as a revenue.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Get hit harder than others. But what technology has always done is people shift into other jobs or maybe some people will be a hundred times more efficient. I think you'll have some cases where labor, like now that take the Eve example that I gave you. Wow, now I can do a hundred times as many cases or five times as many cases as I did before, I'm going to hire three more people. Or I can now be in business by myself because the software helps me do X, Y, and Z. I think a lot of that stuff is going to start happening.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“I'm not sure about that. I think in certain areas for sure. I mean, in general, I could even click up a notch, which is if you think about SAS. Broadly speaking, I think there are kind of three types of SAS companies right now. There are the ones that are almost impervious to everything that's happening with AI. And if anything, it's a huge tailwind because they're going to start being, they have the distribution, they're going to start adding features. And that's things like workday and NetSuite and these things where it's like they have the hostages never going anywhere. On the other side, you have things like Zendesk, right? where it's like how many licenses per seat do you need of zendesk if now every customer support ticket can be answered automatically you need zero license like their revenue could go down 100 these are very very different and then you have things in the middle like adobe where it's like ooh maybe i now whenever i want a logo i just go to chat gpt i don't go to like the graphics team so maybe you'll need fewer graphics designers maybe you'll need you know zendesk you'll need fewer customer support people that probably is true right like there are going to be certain areas the way”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Unix terms, right? It's like you should have a little cron job where it's like 5% of your time as CEO should just be like getting to know people at the three or four companies that might buy you. You never go say like, please buy my company. That's DOA. You don't want to spend time with the Corp Dev people because most people like, oh, corp dev buys companies. No, they don't. They execute transactions. If Salesforce buys your company, you're not working for the head of Corp Dev. You're working for like this SVP who needs, who has some hole on their personnel or needs revenue growth in order to get their bonus. There are all sorts of internal mechanics that are going on there. So it's just this highly choreographed dance of just like making sure that you get to the right people in the company, hopefully doing it years in advance, not just going to them when you need to sell your company because there are two independent variables here. It's like when your company is doing, like the best time to sell, by the way.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so I'd say a couple things. This is a very highly choreographed dance, so you can't just say, oh, I should raise. So if you're raising money, you're like, oh, I should raise money. I have the best metrics ever. I'm going to talk to five firms and they're going to compete to the death over winning my deal. Like that was my experience with my series B at trial pay. So it's like, oh, so it's like, and kind of Corp Dev is like, I'm either raising money or selling my company. It's the same thing, right? No, it's completely different. If you're selling your company, you have to spend, in many cases, years getting to know people at the potential acquirer. It's never the CEO unless you're like, you know, what Yan Kumit, WhatsApp. Like, let's just say that you have a company, you do something amazing, somebody at Salesforce should buy it, you would rather go public, but you're like, ooh, you kind of see the writing on the wall. I'm going to hit a wall in a year and a half. What you should start doing then is I kind of call it a background process. If you know what Cron is in.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Don't think so. No, I think it might be harder for a certain set of people that are maniacally focused on like growth over everything else. But like what really matters is growth and stickiness. And the triple, if you're a triple, triple, double, double with terrible retention data, that's going to be very hard. But if you actually have, you know, again, system of record or in that case, it sounds like vertical operating system, that should not be hard. I would do, I love those things, right? Like I would much rather have a slower growing permanent system of record that will never get ripped out than the fastest growing thing on the planet that has 9,000 competitors that are all built in lovable by 17 year olds. I think there's no comparison. I mean, there are plenty of people that would be attracted to both, would be my answer. I'm surprised that it was as challenging as you portray it.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Of systems or record. Number two, and this goes to the fastest growing companies in the world that you're talking about is like software that does the job of labor. These are new, this is, I'll give you an example, like we have a company called Eve. They sell into plaintiff attorneys. What is the”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“If you want to know the three investment theses that I have for our fund, I mean, this is exactly what I told LPs, and we'll answer your question in a second. I think we have three. We have one, which is we invest in system, like I call it Greenfield Bingo. And most of the green, like these are existing software companies, but selling to new companies as opposed to selling to the hostages that will never leave. They tend to be systems of record or vertical operating system. So like the reason why Rill it, I love that company so much. That's never going to grow like zero to 100 in like a month, but it is very, very sticky revenue. Like once you're on like Net Suite has hostages, not customers, they're not going to leave. If Rillet can sell into every new company, like they're going to do great, the revenue growth will be slower, but it will be so sticky and they have infinite option value on adding like, hey, do you want to have a collections AI agent that runs on top of overdue invoices, blah, blah, blah. And that's like optionality on top of your sticky system of records. So number one is Greenfield.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Labor capital and customers, but it's not working yet, right? So, like, I have to have high ownership in order to take to correspond with that level of risk. And those are the two types of deals to do. The danger is you say, you can say, oh, well, this has a million dollars of ARR and they're ahead of the number two player that has 900K of ARR. Therefore, it's absolutely working. Now, you have to have a high bar on the absolutely right. Like, this is crush it. This is the fastest growing company we've ever seen. It probably comes around once every decade. Throw away the entire rulebook and you should be fine owning 5% of that company because it's an absolute winner.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“I know, but the problem is it's kind of garbage in, garbage out. It's like you can always say that for something because otherwise you're like, oh, wow, I underestimated the size of the black car market. It's hard. I mean, the way that I do it just kind of to be pithy about it is like we either want to buy any percent, any percent of something that is absolutely working or high ownership of something that could work. If you really kind of draw a line of like that you have to bifurcate the market. It's like Facebook, if you look at that round, I think Greylock put 25 million into Facebook. Actually, I think the round was maybe 25 million at 500. I think that was the B round for Facebook, split between Meritech and Greylock. But that was absolutely working, right? So it's like, are they getting 10%? No. Are they getting 5%? No, like, but it's like the market winner and things can go wrong. But like, holy shit, it's absolutely working. And like, I don't see that many things that look like that. But when you do, you throw away all the rules. Or it's like this is not working, but this person looks like a super genius. They have high agency. They can get material.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“But I think, you know, where do you, it's like Zeno's paradox, you know what that is, right? It's like you will never get to the destination if you go halfway each time. Is it 9%? Well, why not just do it at 9%? Why not do it at 8%? Like, where do you draw the line on that?”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, this is actually one of the things that we looked at because I kind of feel like my job here is kind of quasi portfolio manager. So I run our apps fund, seven different funds. And my job is to make sure that that fund is as successful as possible. And we're winning the right deals, that we, if we just say, hey, everybody win every single deal. Just win every deal. It doesn't matter. That's all I'm going to optimize for. And we end up with 5% checks in every Series A. Like, you know, that's not going to work, right? We can win every deal that way. What is the front? How far on this curve can you go? And it's the, again, it's the exact inverse conversation that an entrepreneur is having where it's like, I want a tier one investor. I want, you know, an amazing specialist. I want whatever I want this person I want on my board. What is the least amount that I can give up to get an amazing person? And they would love to get 5% ARAN deals done, but they're like, oh, wait a minute, like, that's not going to work. And like that, that's the tension between the two. I agree with you.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“humans do not have the capability to admit that they were wrong like they just want to like say I'm right I'm say I'm right I say if you're an investor you're just going to lose money all the time the most valuable insight that you can have as as an investor is the self-reflection to say I'm an idiot and if I'm if I'm a hedge fund guy it's like I get to sell it's like oh I thought I was a genius you know buying herbal life blah blah blah like oh wow this company's not good i'm gonna sell everything versus no i want to prove to the world that i'm right well i'm going to lose all my money So it's the same thing here, but for upside, we can't sell. But we can say like, this is the winner I want to be in the B at a lower ownership because like this is the fucking winner.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“How do you know to test this hypothesis? And if you win a hundred percent of the deals, that's a very, very good sign. You should try to win 100% of the deals that you want to do. But if you're winning them with very low ownership, you're probably not testing like this kind of efficient frontier of like how far you can go. And you want to have more ownership, right? That's our objective. Like the founder wants less dilution. The investor wants more ownership. The two are like kind of perfect complements of each other. Eventually, you realize, like, I don't want to be a fucking idiot. Like this is the answer to your question. It's like, all right, I wanted 20% in an A round for a company that doesn't have that much traction because, you know, I'm at Andreessen Horowitz and I've got this big fund and everything else. And then it's like, no, no, they're going to do a 15% round or whatever. It's like, oh, fuck that. I don't want to do that deal. And then it's like, holy shit, they've run away with the market. This is the market leader. I'm not going to be stupid, right? I'm not going to just say this is why actually, by the way, I love talking to investors because investors, like most.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, I mean, there are a lot of deals that we lose because we're not willing to kind of go the distance on price. That is a common thing where it's like, did we really lose? Like this has happened to us a number of times. It's like, all right, we want to do the deal. Again, like consensus and non-consensus, a lot of times the difference is just on price or ownership.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“But they realized, oh, wow, there actually is a good point around my whole team now says we have $100 million in the bank. They're going to be wasteful. That culture is something that I don't want. Yeah, I guess I would want the option of maybe selling the company for a billion dollars and having Salesforce come in and say, what would it take to buy the company? What was your last round price? Because I will tell you 100% of the time in every M&A conversation, in every fundraising conversation, the number one question. The first question is, what was your last round price? And if it's like insane, they're like, ooh, that's not good. And then as an entrepreneur, you're like, oh, no, no, but I would take a discount because my company sucks. You can't say that. It just destroys the entire conversation. It just game over.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“The reason why you shouldn't raise your Series A, like there was a deal that I guess we should have done candidly because this company just raised it like a billion dollar plus valuation, but we turned it down. Company had like less than a million dollars in revenue and they wanted like a $200 million whatever post money series. It was just so crazy. I was like, look, you guys haven't started the company before. I have not to like pull the old bald guy card, but like your series B, like even if you have $20 million in revenue, you're fucked. Like you have to be able to walk into a room. The number one question you're going to get is what was your last round price? And people should be wanting to compete to pay three times that price. Like they have to be like, oh my God, what will it take to do this deal? And if you say like, hey, my lab, my series A was raised at a billion and I have a million dollars in revenue, you have ended the conversation. Nobody want the psychology of that round is all wrong. So I give this speech and it just doesn't work. Unfortunately. But I think the smart entrepreneurs, they kind of have this risk balancing thing. It's like they're irrationally exuberant. That's why they put their job and started the company.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“I think it's the same math, but it's dangerous on both sides, right? It's like I always had this speech that works maybe one time out of 100 that I give it, which is kind of like the Spider-Man speech of like with great capital comes great responsibility. And if you raise it too high of a price, you're fucked because I live this, let me tell you my story. I raised it this price for my series C. Then I had like Google that wanted to buy me, but it was like at the same price. So therefore, it tanked the thing. And then my next round, everybody asked me, what was the price of my last round? And nobody wants to invest. I go tell this story. I can introduce the founder to 10 other founders that have lived the exact same thing. It's like, I wish I hadn't raised my round at such a high price. But who starts a company? Let's just think about this for a second. The people that start a company are irrationally exuberant. Like if they thought that the company was going to fail, if they thought they had a 0% chance of raising a series B, they wouldn't start the fucking company, right? So that's why the speech doesn't work. Because I always tell people like, hey,”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Of money. And I know you're still going to make decisions very, very quickly. I know it isn't going to distract you. And really, it's just benefiting me. I hate to say it selfishly, but it's benefiting me is in that now I'm on the cap table. I own part of this amazing company and it's not going to fuck up the company. The moral hazard it is the number one thing. It's like now it's going to fuck up the company either with too many too much primary or it's like, oh, I know. I won't mess with the primary. I'll just buy secondary. It's like that also has existential risk, as I mentioned, for a certain class of person. There are other CEOs that like, you know, one of my CEOs did a very, very big secondary in 2021. And the company is hit on some tough times, but he is stuck it out and he's doing a phenomenal job.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“You run into these very, very challenging scenarios and it's like option A is bad, option B is bad. You have two of two choices. You're at a fork on the road. And there's a funny expression by Yogi Barra, this famous baseball player in the US. When you come to a fork in the road, take it. It's like, what does that mean? He said all these things that make no sense. But what a lot of entrepreneurs don't realize is that the worst option, you think you have two options, but there's a third option, which is making no choice at all. That's the worst option. You're better off just choosing something, and both of them are bad. This option is very bad. So therefore, I don't want to make any choice at all, but you're better off making a choice and committing to something. And if you have infinite capital, you could just kind of continue this. I'm not going to make any choices. I'm just going to sit here and just like, all right, well, I have more money. My ARR is more driven from the interest on my giant $100 million cash reserve. If you, if you, sorry for rambling on this, but like this kind of goes to like founder capital fit, there's a certain type of person where it's like, I give you a lot.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, but this is where I think the motivation of the founder is very, very important. So going back to, like, I mean, Nick, who's the CEO of Rilla, I mean, I think he does have a bit of the Count of Monta Cristio and him. Like, and it's like, he doesn't want to go take this money and go spend it on extravagant things. So I think you have to make sure that there's kind of like founder capital fit. Nobody ever talks about that. It's like, okay, if I give you a billion dollars, what will you do with it? And 99 times out of 100, the answer is going to be bad news. And not even bad news around waste, but just bad news in terms of mindset. Like it's another form of moral hazard where it's like, I'm never forced into making hard decisions because I have infinite capital. And you kind of want to force people into making hard decisions. And like I live this, I mean, I've tweeted about some of these things during my painful existence at trial day where, you know, I think we had a layoff 70% of the company and then we eventually turned it around and sold it to Visa and there were all sorts of tough times therein.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, I did one of them, right? Like, I'm on the board of Rillet. I did the series B, and it was 60 days after the Series A, and that's unfortunate. I would have rather done the Series A or rather done the C, of course. But if you find the winner, it's also very expensive not to do that deal.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Revenue is really scaling, and these numbers are insane. And those were Series A's. And I get very excited about those. But I think your mileage.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Million dollars of ARR when I invest in it. So it's just all over the place. So I think it's just hard to kind of cast a generality. There are certainly ones where, like I used to call this the Series B trap, but again, I think the nomenclature has shifted. Like I would have agreed with your team if you called it the Series B, because at that time there was a seed, there was a Series A, and the only difference between Series A and Series B is that you increased your burn and built infrastructure and kind of scaffolding. So it's like, I have a company. I have customers. I have signs of product market fit. I know now I should hire an HR team and a marketing team and all this other kind of shit that doesn't actually have any kind of impact on the metrics of the company. And that was the Series B, right? And then it's like, why would I invest in a Series B? Because I get half as much ownership and nothing has changed vis- ⁇-vis the Series A. So yes, there's a class of Series A's that look like that. But I would say of the Series A's that I personally did in the last year, like most of them have been like, holy shit.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, I think the problem is that there's the nomenclature, which kind of varies company to company. So when I started trial pay, we raised, our Series A was $3.1 million on 9.5 million pre. And that was expensive. I remember arguing with the partner at Battery. It's like, this is the most expensive deal we've done. This was 2006. At SiteEvisor, I think we raised 2.7 on 2.7 pre, so even lower. Hence, he was right. So now you have a pre-C to seed, a seed extension, a seed extension to like, what is a series A? There's not like this, like normally a series A would be like the first institutional round of money. Now there's so much variance because like, oh, there's the series A where it's like five superstars out of open AI and they need tons of money for compute. No moral hazard on that. You're not going to go spend money on people. You're going to spend money on GPUs. That's one form of Series A. Another form of Series A is like I just did a Series A where the company had like 10.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“You're going to come up with more creative ways of actually solving the problem. You're going to solve it with technology. Whereas if you have, if you just say, I'm going to solve it on the input layer, I'm going to like address my constituents by saying I'm going to just allocate more money to this thing. You're going to get a worse outcome versus I allocate less money with great people. This is the key. You can't just say like I'm going to allocate less money and give you the worst people on earth. And then no. But it's like take tax fraud. I would rather have two people at the IRS than 80,000 people, but have those two people be the Noam Shazir, some other super genius. Because if Jeff Dean and Noam Shazir are running the IRS, like, oh my God, like that would be so much more efficient. But the input cost would be like 100 as much. And there's always that disconnect.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Moral hazard, that's the economic framing, right? It's moral hazard on both primary and secondary, to your point. Necessity is the mother of invention. So if you have $100 billion in the bank, when you really should only have $10 million in the bank, you're like, ah, I'll do 50 things. I'll have multiple layers of people that I don't need. And it's interesting. I find that a lot of people, when I think about the difference between conservatives and liberals or people that believe in big government, small government, a lot of it comes down to the disconnect between more input is better output. Like a lot of people just believe this. It's like, okay, you know, the IRS, the internal revenue service, like, oh, you know, there's a lot of tax fraud. We need to hire more people. And if we have more people, we're going to do a better job of catching tax fraud. Or like, oh, the military, we should have more people in the military because that way we're going to do a better job. Whereas actually, as you know, it's like sometimes there's addition by subtraction. Like if I have a smaller team, there's less communication necessary.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Monte Cristo and they want to go for it, like, okay, that can make sense to me. And if you offer that to all employees and all investors and everything else, I don't love the idea of it's like people are looking at this as spreadsheets. There was a fund in 2021 that did like a massive secondary into one of my companies. And I was really against it, which made me super popular with the founder, you can imagine. They were like, oh, well, we own 4% of the company. We want to own 8% of the company because 8% is more than 4%. I'm like, dude, I totally agree with you. 8% is more than 4%, but you have now introduced moral hazard into the equation. Because if you give somebody generational wealth, you can hope that they're going to kind of maybe, like the upside would be like they're going to swing for the fences and go for it because otherwise I would be happy selling for a billion dollars now. It's like fucking I'm going to go for a hundred billion. Okay, that's great now we're all aligned. But the other option is now they don't care about getting liquidity for investors. They don't care about getting liquidity for employees. They're quite comfortable like you don't want to have that.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“I think this is a big challenge. I mean, if you look at all the unicorns and how many conform to rule of 40, it's pretty small. Many of them are shrinking. So probably of the unicorn class, I would bet that maybe 5% will ever be able to go public, which is kind of shocking, right? And then because so much money has gone into venture capital, you have this problem of, I mean, I will say on the record, I hate massive secondaries because it kind of turns you from the Count of Monte Cristo to like the whatever the opposite of that would be. Like the, I'm now going to go vacation in the Cote d'Izour or something. Like, that's going to now say I am now at a fundamental disconnect from my employees and my investors because I'm rich and they aren't. That's not a good setup. You kind of want everybody to be in the same boat. The reason why I mentioned that is like you have some companies where it's like, you know, founders taken a $50, $100 million secondary. That's fine if they just turned down a $10 billion acquisition from Google and they're the count.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Company is hopefully have something that I hate to say it, but it's like you want to have hostages. You want to have all of the data in your company. You want to have all of the data of your customer in your product and then just make sure that this is, I think, the thing that we talked about. What do you do? You go boring, you build the most boring thing possible. Nobody really cares about it. Nobody's that interested. I mean, that's why I love Vlad at Ask Leo is like, who cares about procurement? It seems kind of stupid. It's not attracting 9,000 competitors, but hopefully you get all of the data in there. And then you can build these interesting things on top. And you're not going to attract that much competition. And even once you do, it's just kind of hard to switch. So I don't know if that answers your question.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“To almost zero, this would normally take a long time. In 2025, this can take weeks, which is bonkers, right? Because all of these layers of past innovation have kind of like almost like a Russian nesting doll kind of concentrically grown against each other. So because you have cloud and because you have mobile, everybody in the world has a smartphone in their pocket. All of those smartphones are connected to like, you know, infinite computing in the cloud or near infinite computing with like a dearth of energy in the cloud. And now I build something marginally better. I can get into the hands of a billion people overnight. And that's just so, so different. But I think on the hostages point, if you build a system of record, right, like it's just so hard to switch, that has not changed. But now I can go compete. I can build a software product in like two weeks that would have taken me two years. So that's going to massively increase the pressure on the application layer. So the best thing that you can do if you're an application layer.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Anthropic, I imagine, has gotten very good at coding, but it's kind of the application layer tends to be a little bit stickier, but the problem is you might have 9,000 competing companies at the application layer, in which case you'd rather be the infrastructure layer. But the infrastructure layer is pretty hotly competed as well right now. So I don't know. I mean, the more relevant question for me is in 2025, the ability to go create a software product is so easy. I published this chart with the help of my friend ChatGPT of how long it took Visikal, which was the first spreadsheet that came out in 1979 to lose to Lotus 123. And then how long it took Lotus 123 to lose to Microsoft. And it took about five years from Visical to go from 100% market share because they were 100% market share because they were the only one in the first to 50% market share. It took about 15 years after that for Lotus, which had 70% market share in 1986 or something.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“It's a really good question. I mean, this is where behind every technology revolution and kind of go back to like silicon, then the personal computer, then the internet, then kind of intranet 2.0 where you could write to the internet, things like things like Facebook and YouTube, then mobile, then cloud. There's always been infrastructure layer in an application layer. So you go back, like the infrastructure layer for PCs was, I don't know, like Microsoft and Apple, like the operating system players, the infrastructure player for the internet was like Cisco and Alkamai. The infrastructure player for everything AI are all of these back-end model providers. And then there's the application layer on top. So if I do something, we were talking about Ask Leo, right? Like that's an application layer company. If I were Vlad, I would love to be promiscuous with all the backend models because I should be. And then the infrastructure players are like, oh shit, you know, all of our customers are being promiscuous. Let's figure out how we specialize in a particular area. I imagine that like that's.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“It doesn't mean that there's not value in kind of creating big companies that sell big, you know, startups that sell big software products to big companies. You can do that. It's a much, much harder thing culturally for Silicon Valley, I think.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Or maybe they don't, right? It's like who cares if they switch or not? Like, it's like they'll hopefully die because they're using shitty software. The fact that they won't switch is actually indicative of their mantra on everything. They want to use old technology or their hostage to old technology. Let's just sell into the future. And betting on the future is more fun. I mean, like one of the things that's very, very challenging is you go start a company, you recruit 10 hotshot people from Meta, Google, whatever, and then they're bored to death. Why are they bored to death? Because they can't do anything. It's like they were used to making little tweaks that a billion people experienced every minute, every hour. And now they're at a startup. And the startup, it's been one and a half years and they've made one sale. That's quite typical. And then like you end up losing your talent because it's boring. Like you can't actually do anything. So, you know, it's nice to have these markets that can ramp quite quickly and you kind of want the market to be a tailwind for you.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Better EHR, like electronic health records company, it's just not going to work because the rate of new hospital creation is too slow, right? It's like you can't just sell to the new companies. But you can do that for payment processing, right? You can do that for ERP. You can do it for a bunch of other categories.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“They're not going to go, like Workday has hostages. They don't have customers. They're not going to go be able to sell GE and say, oh, wow, I love you to YC kids. Like, I'm totally switching my HRIS from shitty workday to amazing, you know, AI, whatever YC Silicon Valley HRIS, never going to happen. But if the rate of new company creation is high enough, those new companies will pick the best product. And they're like, oh, wow, I could use workday, but I'm not a hostage, so I'm free. I'm going to pick this other thing. Like I was the first investor in Mercury, the SMB bank. And like until SVB failed, they never stole a customer from SVB. But if you're a brand, as long as the rate of new company creation is high enough, you can play this game that I called Greenfield bingo, where it's just like you pick every software category, you build a better version of that, and then you've got a shot. And that's what Stripeless. I mean, like, that's why it worked. If the rate of company creation is very low, like if I build a...”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“I think this is a great question, and this is the number one thing that so I do a couple things. Number one, if it's like an ad tech company, I know a lot about ad tech, I know a lot about payments, I will force somebody else to join me for the pitch that is like a beginner's mindset mind. So I think that's one is just like have a sparring partner internally that has that, you know, what if it works? You always have to be like, what if it works? So that's number one. Number two is I like to ask the entrepreneurs like, what is different? And the thing that's different, like the reason why Patrick and John made Stripe work partially is it's like they just believed that a great number of new companies will be created and they're going to pick the best product and they're going to have the best product. And actually, this informs a big part of my investment thesis now. I mean, I call it Greenfield, but there's a saying that I use a lot, which is the best companies have hostages, not customers, right? It's like, you'll appreciate this if you're an enterprise SaaS guy, right? It's like the best companies have hostages, not customers. So if there's a company that has something marginally better than workday.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“tons of money. Doesn't give a shit. He starts a competitor called Upgrade. No, no accident that the company is called upgrade. It's like an upgrade over UMFers, right? Starts upgrade. Upgrade has a multiple of the market cap. It's probably like worth 10 times more than Lending Club now. So that's a very, very classic commonality.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Because going back to fund size, if somebody offers you $100 million and you're an 18 year old kit, that is transformative. You'd have to be an idiot to turn that down, or you have to want revenge or redemption, revenge, redemption, kind of same thing. And I find a lot of the best entrepreneurs, they have that going. Like they want to prove they're better than everybody else. They had some childhood chip on their shoulder or they were wronged at their last company, like Dave Duffield has this hostile takeover of PeopleSoft. Of course he starts work day and he's like, fuck you, Larry Ellison. Like, there's always that kind of energy. So the Catamon Cristo thing, I don't know how to describe it, but like the motivation has to be beyond how I want to make $50 million because if that's the motivation, like it's not going to work for our fun size. I love seeing that fire. And again, like a lot of the most successful companies that I've seen, they always have that. Like Renault Laplanche starts Landing Club, fired from his own company.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh, what was trial pay? Or, oh, I'd never heard of this. And it's like, come on, man. Like, how are you? You're going to spend 10 years of your life building this thing. And you really should study history. Brian Cheskit, Airbnb, studied everything about bed and breakfast and hotel industry in the 1800s. Like, this is a very, very classic trade. So let me just finish with this. So again, labor capital customers, study history. And then my favorite book of all time is The Count of Monte Cristo because it's a story of revenge. And the reason why this is so important, if you know the book, it's by Alexander Dumas. Edmund Dantes is wronged. He sent to prison for bogus reasons for supposedly being a Napoleon supporter for like 17, 18 years, eventually gets out, becomes the richest person in the world, but doesn't give a fuck if I can use that language, just does not care. He wants revenge. Like he wants to destroy his enemies and just like conquer the world or just really destroy his enemies. And you need that kind of motivation.”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source
“Time. I was not in the Drewson Horwitz, so don't hold it against me. It didn't hurt our DPI. And luckily, the firm invested in them. But two things, I asked Patrick, you know, where are your customers going to come from? Because everybody uses chase payments. It's like, oh, my customers don't exist yet. It's like the stupidest answer I've ever heard. But obviously it was genius. But number two, what really did impress me is that he knew everything about the history of the payment systems. I think he actually went out to go meet Deehawk, the founder of Visa. John Collison gave me a book on like, you know, one of those Springer yellow academic textbooks on the origins of the payment system. They had studied history so much. Same thing for Vlad Robinhood, studied history so much, same thing for a Perva at Instacart, like, you know, went out to go meet the founders of Webfand. This is a very, very classic trait. On the other side, I will meet people that will start a company almost exactly like trial pay or almost exactly like a firm. And I know a lot about these two companies because I started them, right?”
2026-01-12 · The Twenty Minute VC · 20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital · IDENTIFIED FROM THE TRANSCRIPT · source