20VC

“I look at ours, and our biggest mistake, and I can look at Deal, 11 Labs, I can look at Granola, and Starcloud, Fractile, could have done them all, but would have had one to two percent, and all of them we turned down purely for ownership, and that is hundreds…”

“I do all questions myself. I would never use AI and I'm very concerned about it because you lose the muscle to me.”

“Pretty much only hire immigrants. British people don't work very hard.”

“We've lost two deals in the last year. And listen, we got outbid, I'm, I don't know if we would have won if we'd paid the same price, I hate people that say that. Yeah. But by like two or three X, we bid one 50, and another we got outbid by 300, another we out…”

“I remember calling my mom and telling her I was dropping out of law school to do this podcast. That made no money. Having worked so hard for years to go to law school.”

“I would say nine out of 10 young founders that we meet pitch those three exactly, and you're like, wow, this is very aligned.”

“It's three hours long. Everyone should be able to go to a cinema with their families. But if you were asked a question on what's apps like, You need to respond within three fucking hours. It drives efficiency and urgency.”

“The first money we ever made from the show, we made it because my mom has MS and we couldn't afford treatment for her. And the only way that I could pay for it was by putting adverts in the show.”

“One of our biggest LPs was a six-year cell cycle.”

“My biggest regret with our Series A fund is not being more elastic, disregarding the Series A mandate, and just saying I'm going to leverage the brand and the access that I have, arrogantly, forgive me for that, to get into super hot companies like your 11 Lab…”

“When we did Lovables A, it was like at three million in revenue. By the time the legals were done, it was at 20. And so the multiple had gone from 70 x to 10 x.”

“When we think about our entry price, do we think that we are able to three X that entry price within the next fundraising round?”

“We lost a deal recently to a large mega fund, and we did three on 15, and they did 10 on a hundred with no lick pref pre-anything.”

“If they sell per seat, we're not doing it. We need to replace jobs. Like labor displacement is what we're investing into. And that's the only way that we can actually return the amount of money that we need to now to make funds worth it.”

“When we fundraise, we raise from very rich individuals, we raise from, you know, institutions, and I would, in between sets in the gym, walk around in my two-minute breaks, and I would message individuals, this was, and say, hey, I'm going out to raise the new…”

“I would never have started the media company. If I hadn't been kicked out of boarding school.”

“It took me four years before I got a thousand plays.”

“Well, this is why our venture funds are doing so well right now, which is because everyone has a venture capital fund today, sadly, but not everyone has distribution.”

“My business partner always tells me very correctly, life is like a cooker in a kitchen. There's four hobs, you know, that you turn on. There's family, there's friends, there's work, and there's fitness, ok? Family, friends, work, and fitness. And the trouble i…”

“So I hire, bluntly, Asians or Eastern Europeans, and very young, sub-twenty-three, 24. That is a sweet spot for us.”

“We had a company that went from 400 K to three million Naira, classic enterprise SaaS business, bread and butter enterprise SaaS that would have had five term sheets from five good firms, 120 meetings, one term sheet and it was ten million round on a 40 post.”

“We invested in a company that does, like, rooting away from Apple, just to, like, it's, and it will be a great company.”

“It was 250 K at twenty five million. We're a big fund. It's like one percent, but I should have done it and I would have done it if I'd spent more time on it and I hadn't tried to focus on efficiency and clock speed.”

“For us, I look for people who have either extreme trauma or extreme masochism.”

“Do you know, the funny thing is we have a like Yolo segment of our fund, which is like, yeah, which is a tiny pool of cash, whatever, like two million or three million, whatever. But it's basically, we have amazing access because of the shows and people will g…”

“We just did one in Germany peak when we did it. Two, 200 K when we did it is now at a million, like three weeks, but fucking nuts. The customer adoption that one of the fastest polls that I've seen in terms of consumer demand or customer demand,”

“We are in a company that is similar to superhuman that will be at More than their revenue in nine months for what it took them eight years to go to.”

“We lost to Series A, actually last 10 days, and it was doing five million in ARR and it was, yeah, started at like, two, twenty-five million ended up at 600.”

“We have three companies that have gone from zero to a hundred million there in a year.”

“We have 10 times bigger audience on audio than we do on video.”

“When we did Lovable, I think it trebled its revenue by the time the round had completed, and I was like, I would want to retrade on price. Like, it literally was only a 10 X revenue multiple when we did it.”

“I did three on 15. Handshake was the founder. It was pre-product, pre-revenue, pre-everything, but amazing founder. And he called me up and said, I would never walk out on a handshake. But I got offered eight on a hundred, and it's uncapped.”

“We've lost two deals in 24 months where literally they trebled the price and went to common stock.”

“Our new fund is a 125 for seed, so ballpark.”

“We don't do follow-ons at all”

“We just raised four hundred million dollars for a new fund.”

“But I should have, when we started 10 years ago, if I'd just done YouTube, way better. That's a big regret for me.”

“The worst performing segment of our seed portfolio on our farm one was five on 25, because they had too much money too soon, there was a lack of focus, a lack of urgency, and actually they struggled to raise their next round because it was already at too high …”

“I guarantee at the end of this, I'm going to listen to this interview no less than four times making notes of different tacks I could have taken or different points I should have made or different arguments I could have gone down.”

“The British firm, firm, 20 VC pulls in four hundred million dollars to invest in early stage tech startups.”

“He's pulling down eighty million of management fees on that fund.”

“The reason that I'm bullish overall on, I'm not bullish on the European focus. . I mean, I guess that if he's gonna invest the whole, if he's gonna invest the full four hundred million in Europe, that's concerning.”

“Harry Stebbings just raised a four hundred million dollar fund. That's amazing. That's incredible, by the way. Harry is gonna make eighty million dollars guaranteed in fees. Just fees. He could be the worst investor in the world.”

“We remove signaling so we don't ever do follow-on.”

“When you actually look at the data, and we have probably the most data across, I think almost anyone, we have 2700 GP track records, and when you look across that data set, 78% of the time reserves are misallocated.”

“And then there are the really dangerous investors who think they know everything but actually know nothing and want to do a lot. Big cross. Worst of the worst. Europe has a lot of them, sadly.”

“I would just say that build your cap table like you do a sports team. Everyone has a very specific position. A left back, a right back. Have someone for PR and marketing. Have one for engineering and recruiting. Have one for fundraising. Have one for pre-produ…”

“I always want to roll off the board. As you said, you shouldn't have five investors on the board who generally don't have that much of a different perspective. If at the Series B, not that much use for me to be there, really. If the founder wants it, fine. Abs…”

“So if you come to a venture market with a 10% dilution round, you're not gonna get the best venture investors in the world to partner with you, because you're gonna be giving it max eight percent away, because there's gonna be two percent for angels, maybe eve…”

“I've done a 170 investments in 10 years. And we analyzed performance across them, according to actually how much they raised at the seed. And consistently the worst performing companies raised five million or more at the seed round.”

“We saw the creator economy hype of like the easy wins that you get from having big famous people on the show. And it's like very easy to get big numbers and be very famous, but actually that's not who we are. We are incredible shows with the best entrepreneurs…”

“Well, I, my mother got MS, and I, we didn't make any money from the show, and I said, I'll pay for the show, and we used the podcast to pay for all of her treatment, hundreds of thousands of dollars.”

“We have a cheat with the content business because actually we're able to sustain momentum without doing deals where our competitors have to do deals to sustain momentum.”

“My worst performing companies are the five on 25 or bigger.”

“We got a tiny check offered to us at like a hundred million price. And I was like, what's the point in doing?”

“I'm very demanding. And do you know what it's led to? Honestly, ARA has created a culture of fear. People are like genuinely scared, which I don't want.”

“The biggest strategic mistake that I made was I waited six years to go to video. I thought that actually people felt much less comfortable on video. I felt that they would close up more and we didn't do YouTube for six years as a result.”

“I did a couple of these like round tables with Harry Stebbins on 20 VC and I did 50,000 with him and then 10,000 with a couple other top, top investors that we would have an IPO a week in the second half of the second half of this year.”

“I was laughing with our CFO this morning, because we've got a company where we did the first round for when it was a SaaS company, pivoted to a foundation model, and now it's worth three billion. You can't get fucking liquidity on it, Jason. So like, we own tw…”

“I always think, actually in most roles, it's about a week, which is why I try and pay people to take a week off their job beforehand. I say, hey Matt, it's a big decision for you. Let's pay you for a week, join for a week in, in kind of quiet, and we'll see if…”