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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“Yeah, I've done really well as an angel investor. I used to do a ton of it early days of Flexport. So I started this company called ImportGenius.com that throws off a lot of cash. It's a nicely profitable business. So I actually started as an angel investor while I was in Y Combinator because I realized I had inside access. I was kind of like a”
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, constantly paranoid. Almost all of our competitors have had major hacks in logistics. Like it's been a major target area for cyber and there's been a lot of like ransoms.”
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
“That's why I don't want to have to do it for a lot. In some cases, it might be a bluff. I couldn't do it for all of them. And I don't want to dedicate that much of our engineering resources to replacing SaaS. Like I want to replace work, like expensive labor, and I want to build our product and make it way better. So I want to like focus on our core business with our engineering talent and like not.”
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
“Definitely want to be in big markets too, but I think we're coming back to our earlier thing about SaaS. I think there's going to be a lot of categories where you say, for example, there's one or two pieces of software that we fully replace and killed it and more every few weeks. But there's going to be a big category where you take, like one of the things I'm having our procurement team doing is make the PowerPoint case study of the one of the SaaS that we did replace and how we did it and how long it took. And then just go down the list of all the other SaaS vendors that we have and say, hey, look, this is what we did because the vendor didn't reduce our rates. So I need you to reduce your contract rates or else I'm just going to have to vibe, you know, replace you guys.”
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, wow So I suspect that we'll be replacing a lot of these things. And I think a lot of what will happen is you'll just shake them down. I don't know about Salesforce. Salesforce Slack is also going to be a great, turned out to be a great acquisition because like that's pretty sticky. Nobody wants to replace, build their own Slack. I could see a situation where you go, hey, we're cutting Salesforce and they just raise their rates on Slack.”
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
“Some not those names in particular, but yeah, some, and I think the negotiation that we're going to have with Salesforce is going to be a lot different than the last one. Because I think selling SaaS to tech companies is going to be a tough business because we can build stuff ourselves. And Salesforce is great, although most of our people don't like Salesforce.”
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
“You probably go through these phases, right? I mean, I think the thing that you cannot have is them being like union representatives of your employees. They're not. They're to represent the company and therefore the CEO. And so if you don't have that as a CEO, like a trusted HR leader and you feel like the HR leader is more on the side of the employees than on the side of the company, then there's a problem. There have been periods in my company's history and like the industry in general where you're like didn't have the right HR leadership that wasn't focused on the business outcome. But the employees are the company. And the company is the employee everything else is a fiction. We're just like just a fake brand name here with a bunch of people that are building the company or serving the customer. So the word HR is kind of wrong because they're not humans are not a resource that you can mine and take out of the earth. Like you have to give back to the employees and have a two-way relationship.”
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, for sure. Events works all day. And by the way, you don't have to be that crazy to do events. B2B marketing is events marketing to some extent. And like, that's like plain vanilla. But by the way, you don't need to go hire a CMO to run events. Conferences are kind of hard to pull off, but like normal events like hey, host a dinner, you don't need marketing at all. You just have your sales guy call the people and give him a budget for 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
“No, I mean, a million dollars sure. We do like a conference that costs maybe a little bit more than that, customer conference.”
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
“Yes, and like as an employee, as it's so hard to take that risk because you're like, I don't know if I do something crazy and it like blows up, I get fired. Like, why take the risk? So it's very, very hard to find like a marketer that's not part of the founding team or like somehow you have to give as a founder if you're not the one coming up with these crazy ideas and trying things like you have to protect the team and let them, you know, the leaders there and let them know like I want you to experiment because it if it's not crazy, it won't work or it has to be very expensive. And startups can't afford that. So it's the big benefit that like a big brand has is they can just do really expensive stuff. It's expensive as a feature in enterprise marketing because it's like you wouldn't spend a lot of money on something promoting something if it wasn't good, so it must be good.”
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
“Different reasons. Marketing and enterprise marketing, the moment something works, it stops working because the competitors will copy it. And so it's like it's all about creativity and originality. And like, how do you get creativity and originality and B2B enterprise marketing? And if you are creative, like you probably kind of become a founder if you can do good storytelling and creative ideation in the marketing storytelling angle. So you find a good marketer in B2B. We really want to lock them in. And so it's been a hard one to hire for. And also to do that, to do like successful B2B marketing and stand out. Like it's one thing I just make good sales decks for the team and like, okay, fine. Like that's some baseline stuff, but you're not going to differentiate or move that bend the curve on a company's success. You have to be doing kind of crazy stuff. Most crazy ideas are bad ideas. So it's like being an investor. Like you want to do crazy things that happen to also be good ideas.”
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 gets a little crazy, right? That's a lot. We need to have an office in every country on earth. And then that's only one person at a time.”
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 bad. It's bad. Like, it's the nature of our business. So I do want more of our talent to come back to SF. Google has this new product. I haven't used it yet. They built this, I think HP is marketing it for them called the Dimension”
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 just got to do what you want to do. I mean, I think all the bad things that have happened at FlexSport were when I didn't do what I wanted to do and was trying to wash. It's the exact same with every meeting that you have. I struggle. We struggle because we're still, even if we're in office, we're distributed. We have 40 offices. We need to be in every country. So I struggle personally and my team all knows this. I struggle with paying attention in like video meetings.”
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 say it's white collar fraud. I have a three year old and a five year old. The idea that I could do any work at my house is like a total fantasy. Like, come on. You're kidding. And like, I have a bigger house than most employees do. Like, I actually do have a private office. I can close the door on. It doesn't matter. Like, there's no work getting done at that house when the children are around. And the kids come home, when to school and 3 p.m. Like your work day needs to keep going. So I think I'm highly against it. But we're five day a week in office as the baseline assumption at our company. And I made the mistake during COVID of like going remote and letting it stay remote for way too long. And so like I think our culture suffered as a result. Was it difficult?”
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 our customers aren't there. So I don't need a big sales team in San Francisco. You know, we need to be everywhere, not just in San Francisco. So I think we maybe overdid it, though. Like six years ago, five years ago, I had 800 people in San Francisco. And right now we're down to about 75. And actually, I'm like looking around being like, my leadership team is too distributed. I want more talent in San Francisco. So I'm probably going to start pushing more of our employees. Like I used to come move back to San Francisco. I just got our CFO to move to San Francisco. It's made the business much better.”
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 we basically moved away from San Francisco as a result. Like our team in San Francisco is maybe 4% of the companies based in San Francisco, even though that's where we're founded and where I'm based.”
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, that's the next I was going to say. It's like, with that caveat, you probably will get a bet. Like, the fact that we're a founders fund company has made so many other investors want to invest in FlexPort and like.”
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
“Don't ever that I disagree with. It could be quite uncorrelated, like the best brand name investor could pay more than the second best sometimes. That's very hard to give generic fundraising advice. I think it's very dangerous. If a founder asked me for advice, I'm like, you know your situation much better than I do. So it's like you have to be careful on 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
“Man, he's sort of an enigma, just amazing how far in the future he's able to look and be right the number of predictions that he's made well out there just kind of blow your mind. That's not unique insight for me, but that's one of the things that amazes me. Actually, one of the things I love personally about Peter is that I feel like most people I talk to talk too slow. And Peter does not. And if you accelerate your speech with him, at least when Peter and I talk to each other, I think we talk like two times faster than when we talk to other people. There's never a moment where he doesn't understand what I'm trying to say.”
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 have to go look at the latest cap table, probably like almost 15% or something, maybe 12%. There's been some dilution.”
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 like, here's how I screwed this up. Best offer I got was $275, but the firm wants board control. So if you'll just do it without taking the control of the board, you guys can have it. And Peter just offered 37275, which wasn't as good as my 500, but he didn't need to do that. I told him he could have it at 275, and he offered 300.”
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
“Being preempted, so I had no data room or deck or anything that you would need to do a fundraise. And I think the word must have got back to this investor because he coached me. I basically never talked to him again. He definitely didn't show up with an actual term sheet. And then now I'm in the midst of a fundraise where I've set this artificially high price and I wasn't fundraising, but you can't like turn off the fundraising. I don't know. We were going to need to, we didn't need money then, but we were going to need it within a year. And so it was just like this very awkward position. And no and founders fund was our investor at that time. They'd led the series A. So first mistake, I should have just called Founders Fund day one and said, hey, will you do this round? But like, I thought I was hot and like, yeah, eventually I did call Founders Fund and told him, yo, here's what I screwed up. Like, I tried to raise money, failed. I did have an offer, but the best offer I got from my process that I ran post was like a $275 million valuation instead of 500. And I went to Foundry Fund, I just told him every.”
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. The first time, but they're both my fault. Well, at least the first one was definitely my fault. So our Flexboard Series B round, and we were like a hot company. We were getting a VC came in and tried to preempt our round and offered us for our scale and where we were, what were great terms. I think it was at that time it was like 50 on a 500 million valuation or something. But like this was in 2015, I want to say 2016. It was pretty early in our journey. We were founded in 2013. So it was like, they were good terms. And I was very happy with the terms. And yet the VC wasn't that famous or well known. They're a good firm. I'm not going to say their name, but they don't need to be starting fights. But I decided, and this is where I screwed up, I decided I could get the same or better terms from a better known investor. And so this was like on a Thursday. And I spent Friday and the weekend hustling trying like pitching a whole bunch of investors. But I had no, I was.”
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, they did. Well, I remember when Obama went there, they didn't even open the rule out the red carpet. They didn't bring up the stairs to the Air Force One. You had to like, Air Force One has its own stairs, but it's like they're not very good. They're sort of awkward.”
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
“On some level, I think that China and the US, there's a huge amount of mutual dependence there that is underplayed. And I think that there's a lot of the interests are much more aligned than people give credit and all this. There's so much saber rattling and so many people trying to sound, I don't know if they're trying to sound smart or tough or something, but they're casually throwing around war between China and the United States without realizing that such a thing would be a nuclear war and you'd all be dead. And so I think that the odds of that happening are pretty low. I don't, I don't really believe that these countries are going to suddenly start shooting nukes at each other. And yet if you have war between these two powers, that's what it would be.”
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
“Not really. I mean, I think I lived in China for a few years and I speak Chinese passively, not really well, but I could have a conversation. And so I feel like I know China better than most, it's not high bar.”
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
“Not really. I don't know how they work, like how they can stay competitive on some level, but if they're open source, they're open source. Like, who cares where they're from? We can use 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
“No, but your question was do I worry about that? I don't care. I mean, anthropic go to zero. I don't care. I didn't put an amount of money that matters for me. So on my personal basis, and if AI and intelligence becomes really cheap, that's like much better for the world and for 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
“But not like early. I'm not like. It's like 600 or something. It already ran away. So I'm not going to make much money off 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
“Yeah, the enterprise business seems great. And the team, I think there's a lot of value of this cohesive team that's been together forever and open AI has had ups and downs and people have left and it's been hard to keep the whole team in place. And there's just so much value and like founders that love each other and no one quits and the talent density, et cetera. But OBI has like people that sleep on it. I would invest in both, right? And I have, I would do as much as I could into either of 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
“I think they're still more habit formed on Claude, but they use Kodaks. We're cursor users. We use everything. As an enterprise, we've been more Gemini because we're Google Docs centric. And so it's like a really nice how baked in it is. Notebook LM and these things. But all of our employees have clawed access as 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
“We switched back and forth. We're using Codex too. In fact, yeah, Codex won us over. They stole Sam solemn my heart two months ago when he said you can have two months free. That was like 30 days ago, so we switched everything to Codex.”
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
“You see costs come down at least. Yeah, I don't know that you're going to see a huge revenue scaling of this. I mean, by the way, our competitors, like us and others that are scaling, that are serving data center companies, that part of the business is growing like crazy because the data centers have to be built.”
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
“Spend about $150 million a year. The biggest one. We don't have too many like that, but we have probably a dozen that spend over 50 and then a long tail. Wow. Yeah. Logistics expensive. It's 11% of GDP. So people spend, and these aren't, they don't have to be that big of company. That's the thing that I will often have to educate investors on is like logistics have much bigger market than software. So for example, like a typical, like a medium-sized company will spend, call it five percent of their revenue companies spend about five if their physical goods companies will spend like five percent of their revenue on logistics. They're not spending five percent on any software. You know, maybe like at scale like our price point is similar to what you would spend on Oracle or something for a comparably sized company less like.”
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. Actually, speaking of the, so it's quite common in our industry where you have these like forward deployed, they're not engineers, like I said, they're forward deployed logisticians or something. Like they're on site. And we had this recent, we just had this huge customer win, one of our biggest ever. And I was like, wow, this is great. But I had heard that our competitor has one of these four deployed logisticians and runs their RFP, runs their process for choosing a freight forwarder. And they always choose themselves, which I'd heard about was like, wow, this is idiotic. Like, why do they do this? It's a great business. I'm going to choose me. And we won. And I was like, wow, what happened? And I found out the competitor had been acquired by another one of our competitors. And they did a huge layoff and they fired the person. And she got hired by the company. And then they chose us to get back at 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
“No, it's not true. You can do it without that, but your business is better. But if you can get that level of integration, you know, the freight industry was the original FDEs. They just weren't engineers. But one of the big tech companies that runs like hyperscaler, let's call it, has one of our direct competitors has 130 full-time employees that work at that 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
“Actually, a pretty good business. I think they haven't grown that much, but they print cash in like 3,600 salespeople. If Yelp can have 3,600 salespeople, like, I feel like we should have more than 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
“Certainly want as many of those people as you can get. There's just like a lot of mass that you want out there in the field. I mean, think about our business. We're global trade platform for global trade. There's every business on the planet that needs to ship something anywhere. There's a lot of boots on the ground that you want to just to interface with those companies out there. And like there's a limit to how many relationships a human can have. And I think you can probably use AI and use other techniques to like double that ratio or something. But like there's some limit to how many relationships you can maintain. And it's a relationships game at the end of the day, sales. And so I'm somewhat skeptical. There's an interesting question, though. Like Yelp has 3,600 salespeople calling out restaurants”
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
“Might be about the same. We're hiring a lot of salespeople and we're expanding a lot in New Markets. But I think you're going to see like a shift from people that today do operations kind of manual work that I was describing earlier into, okay, you've got to, the work style is going to change. And if the people are not able to make that shift, then we're going to have to rebalance into much more customer facing account management, sales, kind of like, all right, how do you, because I think that's the future is just like people.”
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 true in those businesses. Our business has just tons of manual operations with humans like forwarding email. We call it freight forwarding. I often say it should be called freight email forwarding. It's like people passing PDFs around and moving data between enterprise systems. And there's just like a huge amount of human labor. And I think that most of the economy looks like that, not like Uber, which is a highly automated business. Although I don't know why they have like tens of thousands, 30,000 more employees because pretty automated, right? Like I don't quite get 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
“Oh, there's a realistic scenario that they decide that the compute that they have is more valuable for training superintelligence than it is for letting customers use it. And they stop, you know, just cut us off. And we all just come back to being idiots.”
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, I don't know about Anthropic, but on LLMs. But it's possible that the price comes way down, deflation, and it's also possible that we move a lot of workflows onto open source just because if it's good enough, for our coding agents and like for actually developing product, we probably always want the frontier model. But if you're just automating a workflow, if the open source one that's basically free and automate it, then I don't, there's diminishing returns to frontier LLMs. And there's diminishing returns also to doing it. Like once I've automated all the work, I don't want to keep spending the money. Like I had the agents work. Like, I should probably stop. Now I'll keep spending money on code and things that improve our product and our surface area that our customers interact with. But, you know, we're pretty manual. We have a lot of manual processes. Once they're automated, like I should stop spending the money on Anthropic.”
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. We do see ourselves automating a ton of the work and taking it away. You have to, right? I mean, even at five, like, I better save five million a year in labor cost or make my product way better, which we are finding ways to make the product way better.”
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
“We're not even close to that, but there's a world where that becomes. I mean, it has to at some point, it's very interesting”
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
“We're spending like probably like five million a year or something ramping pretty fast though. Like it's doubled in the last few months.”
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 thought that was opaque, but we don't have a budget on our contract. And yet last Thursday, I woke up. I don't know when we're going to air this, but it was like a few days before the end of the month. And it said your organization has reached your limit for the month, which it's not true. Like something went wrong in their side. But I had this like this moment of like, oh man, what if they just decide one day to like cut us off and say, no? And I actually think this is a realistic scenario where 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
“We're using OpenAI, we're using Anthropic. We're going to increasingly use open source models to save money, but also because we don't today have a budget constraint on our anthropic contract.”
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 does a lot, and we've gone a long ways with that, but ages can go the way. Like, we think we can automate the full end-to-end.”
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 a ton of business logic, like a lot of rules, because every, and we serve, we're an enterprise logistics company. We help businesses manage their cargo shipping around the world. Every business is unique and has their own process and their own, oh, we need this data and this format moved into this ERP system. Like, we want you to notify us. Some companies want to be notified 10 days in advance of their container arriving at their warehouse in some seven. And like they really care about that and they spend so much money that you have to do what they say. So a lot of our tech is like this big rules engine and you get all these if-then type statements of, and it becomes very unwieldy, and at the end of the day, it can't really keep up and you end up with people managing some of this business logic. Well, the agents can just do 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