YouSaid · the spoken record

Ryan Peterson

lines on the record: 114
first: 2026-06-20
most recent: 2026-06-20
sittings or episodes: 1
sources: podcast

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“We got to hit our numbers. We got to grow like crazy. And then this automation via AI, we've got about probably like 100 core workflows that are costly that we're building AI agents for right now. And like five of them are live and working and saving us money and 95 that are under development. And I need at least like 80% of those to come to life and like actually have the impact. Otherwise, we're just spending money and not getting much back for the AI.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh, I really would love to sponsor this football club in Hamburg called St. Pauli. Why? They're the second team in Hamburg. And the first team, my great-grandfather was a sailor from Hamburg, first of all. So I've got like a personal history there. I don't know if that team was around back then, but the first team is owned by Klaus Michael Kuna, who's the owner of our direct competitor, Kuna Nagle. And I just love the idea that we would take the second team and beat him. And he would be like, oh, those kids, these damn kids, here they come again. So just more of a troll than anything else. And their logo is a pirate. They're like, oh, no, their logo, but they're kind of like, they're like kind of like a leftist communist-oriented club. I think they would kind of hate us if we tried to buy.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“I'm just glad that my board doesn't screw with us. My board has been like very supportive of us, of me in particular. I don't really want a more active board. They're not super active in the business. They're not like telling us what to do. They don't help that much, but they don't ever hurt. And like I would much rather have that than like a really helpful board. I don't think there's a risk of the board firing me. Someone who's really smart and thinks they're smarter than me might fire me.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't think our flex sports board needs anybody. The board is mostly there to represent the interests of the investors and make sure we're doing a good job, not like who's wise.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“For the last decade, I didn't want to compete on price, and I wanted to be the premium provider in logistics and thought it would be bad to compete on price. And now I'm like pretty convinced that we need to be the low-cost leader and just go so hard at lowering our costs. If you're cheaper, you just take all the market. And I think I was maybe lying to myself because it was too hard to automate the work and too hard to become the low cost provider. And we're smaller than some of the big peers. So they buy freight cheaper than us and stuff. And I think I was lying to myself and it's like, no, you need to be the cost leader. And we have to figure out everything we can to be the cost leader. Masa was, well, he was like, just still under your cost. Like, I don't believe in that.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“They should just have kids and then they'll be sold. That would be sold. That problem will be solved instantly. But if you get a lot of purpose from your work, then you can have the opposite problem of like, oh, like you got to be a great dad.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Sure, yeah. But like, I get a lot of meaning from my work truly, like, I just genuinely love what I do. It's a real mission for me. Like my life's work is building flex work. But a lot of people don't have that. And I was always kind of confused because like most people I meet don't have a sense of purpose about their work like I do. And I'm like, how do these people function? Like, I don't know. How do you get through life? You notice as soon as you have kids, like you will get, I get more purpose from that than I could from Flexport. And so that's the vast majority of human beings should get their purpose from their family, from their life.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, you need to have a great wife. He's a great mom so you have a good partnership. The kids will be pretty natural. You've got millions of years of evolution. It'll be great. Great to finally care about someone besides yourself. Dude, I'm super like, it's like a chemical wash of just like true love that is, you can't get it anywhere else.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, exactly. I mean, you could, like, no, you don't know some of them. Mersk is like a famous company. I know. They're big, yeah. They're a lot bigger than us. But I probably think Flexborg gets more, we're more likely to be sighted in the press on a story about supply chain than they are, despite them being much bigger.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I do. As measured by when I tell my sales team I'm going to do less of it, they always push me to go do more press. Like they say that it helps them get deals and close deals and stuff. But it's one of these things. I think it was Steve Martin who said like he went on the tonight show. He went on every late night show that would have him and then he would go around Wes Holly, we'd walk around Hollywood and nobody would recognize him. Like this is in the early days. And then, you know, so it couldn't tell if it was having an impact. And then after like five years of that, he was like the most famous comedian in America. Everybody knew him. He couldn't go anywhere. But he couldn't pinpoint it to like any one thing. So it's been a bit of my, I only learned that recently. That wasn't like driving me to go try to do more press or anything, but generally I think being famous has helped flex sport a lot and we're way more famous than like we should be given that we're like the 10th largest freight company.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“I get nervous when I have to give a talk publicly and it's very time bound because I'm like kind of long-winded. I can't memorize anything. So I don't prepare like I usually will just go speak off the cuff and I'm a good public speaker, basically a good public speaker, but I can't like memorize. So like actually the most nervous I ever was was the Y combinator pitch because I only had two minutes.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, he had this guy next to him call, and like WhatsApp, I forgot. I think it was a weirdest thing, like, due diligence.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, well, they led the round of a billion. Yeah. And he was like, whatever the price of freight is, you just be 10% cheaper than everybody. And then if someone matches you, you just be 10% cheaper than that, which is like a terrible strategy. I did not do that. We would have burned so much money. But he was very aggressive. He just wanted to push you to go big. I like the mental.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“It's risky. I'll just leave it after he invested. I was going to send him that as a gift. He's very bold. You know, he wanted me, he pushed us to go, hey, be cheaper than everybody because we raised a billion dollars from them.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Probably, like, actually, I'm pretty sure maybe an hour or so, considering the size of the check, I thought it was surprisingly short meeting. He has this painting of Napoleon behind him. And I wanted, I didn't end up finding one. I was trying to buy a painting of the Duke of Wellington to send it to him, right? Who of course defeated Napoleon as a troll, but I never found a good one that it was worthy of the prank”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“First time I met him would have been at his house in Woodside, California, which is like, it's very nice, let's say. You can look up the Z estimate. You're like, oh, this is going to be fun, the Zillow estimate.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Great advice. So I married her. And then she had to quit, in part because of me, because she got a sign to cover Softbank, who's my investor. And I was like, no, can't do it. Sorry. And she knew that it was not a good fit”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“It was. It was a bit. In fact, someone, one of my investors at Founders Fund told me, dude, you need to either marry this woman or break up with her, but you cannot be dating her.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh, well, it's a picking game, I guess, and you only get one bet, right? So make sure you get the right one. My wife, when I met her, she was a journalist actually at Bloomberg. And I still could have killed that Bloomberg story, even though these were her peers that she worked with for years. I mean, it was crazy even then.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, yeah. Some of them are like this and some are. I find it somewhat uncorrelated. Like, certainly they were like that on the way up. Some people get to the top and then stop being curious. And then probably their returns or their impact after that'll slow down is my theory. But you beat some people on the absolute top who don't care.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Depends, you know, also, you want to meet people who are like at your level or see you as a peer and want to actually engage in a dialogue with you. If you're meeting somebody and they're like unhappy to be at dinner with you and they don't care about you and don't ask you questions or learn more.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“And actually, it's an interesting story that we use DoorDash for logistics. People don't think about that. But if you, DoorDash has a bit of a problem there because DoorDash's quality is better than others or it's as good as like a FedEx or UPS. But when you use FedEx and the package doesn't get delivered, people are like, it happens, it's FedEx. But when you use DoorDash and it doesn't get delivered, they're like, why did you use DoorDash? Like, what's wrong with you, company? Like DoorDash is for food delivery. Why did you something they have to overcome because their quality is actually fine?”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“And it was a newspaper. I mean, Bloomberg's not a print, but it was the front lead of the story that Flexport, we use DoorDash to do the delivery. One parcel. By the way, the story did not mention we delivered 40 million parcels successfully, but we lost one and we gave her a full refund before the story ever came out. And that became a scandal of sorts. Nobody would care. Nobody would read it except we have competitors. And the competitors will take your bad news and send it to your customers and stuff. So it actually can hurt in enterprise it can hurt your business negative news stories, even though it's not the story itself. It's like your competitors are kind of low life looking for dirt.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“It's different, a little bit different in enterprise because you have competitors. So like in our case, if we have a negative news story, like literally no one will read it. And we don't scandals. It's like, oh, such and such. Like I once had a Bloomberg article about us where we lost a package for a customer. One single parcel.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“But I don't even mean as an investor. Of course, you want things to just go up into the right and never come down. But as a story of what's compelling to the human, like snap story will be infinitely more compelling if they figure it out and start growing and going like hockey stick again than it would be if it never stopped and it was hockey stick. You'd be like, well, what happened here? Like that, the human brain loves the story, the hero's journey where you got to go to hell and come back. Like if it's just always good, like, that's not fun.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Okay, when you're losing a lot of money, like sports happening, we've been on the hero's journey, right? If anything is straight up into the right, by the way, is pretty boring. Not as an investment, great. It's wonderful. But like as a human story.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“I also think founders should basically never share their metrics, which I've done on the show, so I don't care anymore. But you should never share your metrics.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“And they're trying to get ahead within the firm by showing that they don't bring dumb deals because they've referenced it.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“I heard you picked a lead. And like the amount of rumor mill and collusion that happens in VC, Pounders have no idea. It's like this crazy. And you can use it to your advantage. It can work against you or it can use it to your advantage. You're looking for an outlier who will value you more than everybody else. So like that collusion does not work to your advantage unless they're all hyping you up and saying, dude, this is the best company ever.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I mean, if it's your life's mission and you're calling, then, like, great, never give up and never come up. There's that. There's what I was saying earlier of how much they're a circular rumor mill. You know, like when I was doing one of the rounds of funding we were doing and I was pitching this investor and I think I was on like the third meeting. I'm not one of these people who like, oh, you never talk to associates. Maybe I should be, but I think it's kind of a loser way to live your life. I never had this attitude that like you shouldn't ever talk to the junior people, mostly because I'm not a dick, but also I just assume that those people someday will become like partners and they'll remember that I was cool. I don't know, but I was like on the third meeting with this fund and I was still talking to the not the junior person, but I wasn't at the final decision maker yet. And so I told the guy, I was like, hey, I've decided to go in a different direction here. This isn't going to work out and I'm going to raise, you know, and within an hour, I got phone calls from like three other funds who I hadn't picked a different investor. I just was like trying to let this guy off the hook. And within an hour, I got all the funds that I was still talking to called me like, hey, what happened?”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“3x. Like, if you take my spreadsheet and this investment made three times the money, like the founder is very proud, like, hey, I made you three times your money. But if I remove that and make it a zero, it has zero impact on the bottom line of the fund, like zero relative impact on the IRR because I have a couple that are 1,000 X or 500X. So they strictly, completely dominate everything else. So you don't care like about the ones that failed. And when I write a check as an angel investor, I would just mark it to zero. I don't care. I just assume that it's a zero. And then that way I don't worry if it fails.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, exactly. Eventually, you want to clean this up. Much better if you track it from the beginning. I would say probably it's super power law world. And actually, this is an interesting thing for founders to understand is once you see the world from the perspective of the Angel investor, you realize that we really don't care.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, I didn't for a long time, but at some point I had to clean it up when I was getting married and going through that exercise.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Companies in Silicon Valley, or something, but like it's kind of fake. Like, the market's actually really big. And he stopped me and he's like, look, don't be too dogmatic. It's okay to have a big market, you know? And then a few weeks later, he emailed asking if he could invest.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Maybe. Yeah, they mostly bet on me. They had never invested in this market before, that's for sure. Peter, you know, I met Peter. Sam Altman introduced me to Peter. Sam was one of our earliest investors. And he invested me to Peter to get advice. It was a classic thing because everyone loves his book, right? It'd be zero to one is such a great book. And so Sam introduced me and that book has six or seven, I can't remember. I think there's like six questions to decide if you'll change the world or if like this is like an incredible startup that you should ask. And on five of the six questions, I felt like Flexport knocked it out of the park, best possible answer. But then one of them was one of them is, is it a small market? Because his whole thesis was like, you should have a market that's small enough that you can be a monopolist. When I went to whiteboard with him and hang out with him, I'm like, well, look, I want to know like, should I be, should I make myself like I can make this a small market? I'd be like, oh, we're going to dominate like logistics for hardware.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“I know, 100%. And it was like the third pitch, and I thought we were going to like move to term sheet. And instead, they had brought their own report that showed how the market size was only for Flexport was only $6 billion. And I was just like, actually my partner had the best line. He was like, oh, so it's smaller than the market for USB cables. And it became obvious to me that these, and I said, I don't think in BCG reports. Like I wasn't me that got the BCG report. Someone else did. I was like, just look at every object for the rest of your day. I want you to like look around at everything that you see and just ask yourself, how did it get here? And like, that's our market size. Like, I don't think in.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Market size was too small and it was like the third pitch. And like after this first two, I thought we'd overcome this like we presented some, we found some BCG market sizing report and like shared it with them. And it was like and they.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“The worst one, I've walked out of one investor meeting, not like in a huff. I left my partner there, my co-founder, or like the president of Flexport. He stayed behind. And I said I had to take a phone call and I just never came back”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Did I do? It was like seven or eight years ago. The guy just fell asleep. We ended up winning them over. It was a sales pitch that they weren't a customer yet as a prospect.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“The way my overall experience with VCs have been incredibly positive, including those who've passed and become friends and like people that I hang out with and there's no ill will at all. But I have way more negative experiences than positive. Not to say there weren't positive experiences, but like I think you said earlier you enjoy pitching investors. And I like pitching, but I don't like hearing no or getting ghosted or whatever.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I wonder how many founders out there like actually secretly hate you because you tell them something that they didn't want to hear. It's probably non zero.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“It's good. Do you mind Yeah, fair. Which is always the case, right? PG, his advice to Founders was always you should hear the no but ignore the why because the odds of them telling the truth multiplied by the odds of them being correct are so low that you're just like very little signal in what investors tell you about no you definitely hear the no though they pass so”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“No, I've never had one of those. Really? I had like a lot that seemed like they went well, and then they never invested. The number of investors who ghosted me, by the way, after the pitch, the vast majority, I would say, where I pitched them, it seemed great. And then it just like never hear from them again. That would be the majority of investors I ever met.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Really There's a few people who I should be way more who have wronged me, but I like totally blocked them out and don't care. I don't know why. It might be better for what a single single”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“I think actually it's a great, I have a great thesis around founders who have been wrong, second time founders who feel like they were wronged the first time around would be like great investment thesis. Revenge and patriotism is a great investment thesis.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“No, I'm personally not, but I think that investing in founders who are pissed at somebody and like want to get back at them, like same with Rippling, Dario, I never met before, but yeah, I don't know if he was wrong. Parker's benefits A16Z, they fired him”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Maybe, yeah. So, one of my best angel investments. I was, well, actually, Bitcoin, early Bitcoin, sold that. Don't kidnap me. I don't have any Bitcoin anymore, but I made money on Bitcoin. I was the first investor in Rippling. Put a big check into that. Did really well.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, and I'm friends with Kyle. Why? I don't know. It's just like it was too crazy. Like he was just like throwing this camera set up on the roof of his Honda Civic or no, I forgot what car he had Akura or something. I was like, this is not a thing. It's not legit.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Talk to the people and be like, this is a good person. And they didn't see me as an investor, so I'm their peer, so I could get like the real story. So I invested inside my own batch. I invested in like 13 of the 50 companies or something like that. There was a few good outcomes there. Algolia was an investor in that. But I missed Cruz. Cruise was in my batch.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source
“Wasn't obvious who was great. It was obvious he was terrible, though. And I think if you could eliminate the bottom half, like you're doing pretty well inside of a YC badge.”
2026-06-20 · The Twenty Minute VC · 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport · IDENTIFIED FROM THE TRANSCRIPT · source