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20VC β€” Flexport CEO Ryan Petersen: Two Questions Every Founder Needs to Ask

Episode info Β· 2026-06-22 Β· ~80min Β· Auto-generated captions (English)
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β–Ά 01 πŸ”₯ Motivation β€” Fear of Losing vs Thrill of Winning
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Ryan Petersen β€” Opening

You said remote work is. Can you help me fill in the statement here? Well, I I said I say it's white collar fraud. I have a three-year-old and a 5-year-old. The idea that I could do any work at my house is like a total fantasy. Like, come on. You're kidding.

Our guest today is a longtime friend of mine, Ryan Peterson, founder of Flexport. He's been on many shows before. I don't think he's ever had a conversation as open and honest as this. Where we touched on everything from Chinese open source models, is the CCP a risk, why remote work is like white collar fraud, and so much more. I think the negotiation that we're going to have with Salesforce going to be a lot different than the last one. I think selling SaaS to tech companies is going to be a tough business cuz we can build stuff for ourselves. Revenge and patriotism is a great investment thesis. There's a lot of collusion in VC. Like I have a feeling that most VCs actually collude more with competitors than with their own partners. Ready to go.

Ryan, I cannot wait for this. Dude, we've done this a couple of times remote, but I feel it's much more special in person. We're going to get to remote work, but remote interviews not as good as in person, dude. So, thank you for being here. Yeah, it's great.

Dude, I want to start on what motivates you more. I'm finding this really interesting pattern. It's either the fear of losing or it's the thrill of winning. What which one is it for you? Probably the fear of losing. Why? I don't want to be a loser.

Ryan Petersen

It's like you never win enough, right? Like I've already won and yet I still don't feel like I won. By any standard of what I set out when I started the company, like I've won. My first and only Excel financial model that I made for myself for the business got to one million of revenue, and we did over two billion last year.

I hate Excel models. I'm terrible at it. When I open up Excel, it says sign in or register and I'm just like I'll leave it for someone else. I'm not very organized. So are you not? No. And like I feel like making a good model requires you to like organize your stuff.

So today's rule is we're going to play a game. Now you've done shows before. Um every single question that I ask has to be a question that no one else has asked before. Okay? And if I ask a question that someone has asked before, you have to tell me and I will donate $100 to a charity. Oh wow. All right. So we're Do I get to pick the charity? What are we going to do? Sure. What's your charity? Um, my mom's got MS. I do give it to an MS charity. But that's the deal. Okay. Okay. So, these questions could be weird or interesting. Do I still answer the question? No, I don't answer. I just go $100. No, you just go bang bang. Great. But if you lie, you pay $1,000. So, if it's a hard question, I get out of any question just by paying $1,000.

When when I started as an entrepreneur was kind of like now it's like everybody's becoming an entrepreneur, but I started doing companies like in the early 2000s, late 90s even with my older brother. Uh it was I mean I guess at that time it was less mainstream to start a company and we weren't in Silicon Valley. We didn't call ourselves like tech startup. We didn't raise venture. We were just hustling to make money. And one of my tricks actually was I moved to China when I was 25 years old for this company. And my rent was $120 a month for a two-bedroom apartment in a nice part of a second tier city. And so I knew that actually gave me a lot of permission to be an entrepreneur and to be crazy doing crazy stuff because I knew I could live off of if I could make 500 bucks a month, I could survive. So like I could do a startup. I could take risk cuz worst case like I lived in a nice apartment in a nice town. My total opex was like $250 a month. So it gave me permission to take some risk.

What's your number? What's that mean? What's your number? basically means what's the number that you had in your head of like ah once I have this I'll be happy. So like for me it was always like $20 million with the rationale that you have 5% interest you make a million bucks a year for doing nothing. A million bucks a year is more than enough for anyone who's adjusted not mentally. Money is amazing because the more you have the more you want. You can never satiate the human desire. Of course you want more, but like I only buy trainers. I would much rather have more convenience than more money. I haven't been that motivated by money. I'm more into uh power. I want to do big things.

There was a question that my girlfriend asked me the other day, and she said, "If you lost 90% of your money, how much of your self-worth and self-esteem would you lose in percent?" Oh, maybe you're more adjusted than me. I said, "I'll go down 90%." No, I did. But mine is like my work is directly correlated to the financial outputs that you have. Like candidly, if you are a general in the army, your success in your profession does not correlate to your financial statement. At the end of the day, I'm a venture capitalist. The clue is in the name. If you're good, you make bank. If you're not, you don't. Yeah, but it's, you know, you got to forget the past and the future. The future's not written, so you can go make it.

β–Ά 02 πŸ’Ό VC Herd Behavior & Collusion
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The first one I wanted to ask is when we were chatting before, you said about the nature of VC jobs and why it means that inevitably the way that VC's jobs work is they end up as herd animals. Why did you think that was something interesting we should discuss?

Ryan Petersen β€” Why VCs herd

The nature of the job is simply that it's just such a good job. It pays really well. You basically don't have a boss once you're a partner. You don't have to be anywhere on any given day. And it's very hard to measure if you're good or not on any reasonable time frame. So like you can't get fired.

Not only can you not get fired, but like dude I run a media company, you run a company revenues can go down. They are not certain. Fund fees are legally structured. So if you are a partner that doesn't own the fund you could get fired. So your whole thing has to be how do I avoid getting fired. You can invert the problem and go well how would you get fired as a VC? Like scandal, sure, avoid that. And you can't allow everyone else who works at your firm to think you're dumb or doing bad things, like doing stupid deals. They don't know. It can be bad deals. Like you or they could be great deals. You could be doing great deals, but if people think they're bad deals, you might lose your job. So therefore, okay, I need everyone consensus, right? And if you're you're also going to channel check all your deals. you're going to check with your competitors.

Ryan Petersen β€” The Collusion Thesis

There's a lot of collusion in VC. VCs are constantly talking to each other in part cuz they need to make sure that they don't step out on the edge and do something that their own partners are going to think are dumb. I have a feeling that most VCs actually collude more with competitors than with their own partners because they need to spot check their deal and make sure it's good before bringing it to the other partners to make sure that they're not seen as being dumb. So that's where you get the herd behavior.

I love Keith Rabois who says that actually he likes to sense check his deals with friends and if they don't think that his deal is stupid or crazy, he's not doing his job. Founders Fund and Keith was at Founders Fund for a while β€” there's a few funds that avoid this type of behavior somehow or some people are just born into it with a contrarian bone.

Do you think you can only do stupid or crazy because you have money now? Me personally, I don't have that much money. But you don't need money. No, I have enough. I have enough. Like when you're paying rent and school fees and it's like, oh god, fingers crossed. I think that richer investors make better investors. Like Sequoia are focused on upside maximization. How big could this be? They are not fearful of LPs coming back for their next fund. They're not fearful of deployment speed compressing. They just invest in what they think can be mega companies.

If Flexport would have raised today, what do you think you'd raise at? I don't know. This year we're going to get to basically break even. We're on run rate to do about $450 million of revenue, net revenue. Breaking news here. I haven't shared that, but 450 million of net revenue. What's your growth rate? Last year was 350. So 350%? No, 350 million last year. So what is that? almost 30%. So you're doing 30% at $450? Yeah. And I think we'll do 600. The goal is to keep going 30% every year for 10 years.

Ryan Petersen β€” Two Questions Every Founder Asks (PG)

I got this from Paul Graham where he said there's two questions you need to ask. (1) Are they doing some kind of hack that's unsustainable and going to stop working? (2) Is the market big enough for it to keep going? If the answer is no there's no hack, this is genuine growth, and the market is really big, then the thing will just keep going.

And I think flexport's like that. There's no hacks. It's actually a grind. We've got sales people out there in the field calling on businesses and going around the world. The market's enormous. We're still less than 1%.

The word exit implies that I'm going to stop working. So I don't think of it in that term. IPO would be β€” yeah, we intend to go public. I don't know what the valuation is or should be or will be. If we can just keep growing, you just draw the math out. I'd like to be nicely profitable making a few hundred million of EBIT then we'll go public. It could happen in a couple years. As long as you're generating a lot of cash, if you're really undervalued you just buy your own shares back. People focus so much on this concept of an IPO window. I don't quite understand that dynamic. Just run a good business, make it super profitable, have it grow, and don't compare yourself too much to Anthropic or these AI companies. Envy is one of the seven deadly sins.

Our s flexport series B round we were like a hot company. A VC came in and tried to preempt our round and offered us what for our scale were great terms. I think it was at that time like 50 on a 500 million valuation. This was in 2015 or 2016. So they were good terms. And yet the VC wasn't that famous or well known. I decided I could get the same or better terms from a better known investor. So this was on a Thursday, and I spent Friday and the weekend hustling, trying to pitch a whole bunch of investors. But 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 cuz he basically never talked to me again.

Founders Fund was our investor at that time. They led the series A. So I should have gone first mistake β€” I should have just called Founders Fund day one and said hey I want to raise, will you do this round? But I thought I was hot. Eventually, I did call Founders Fund and told them yo here's what I screwed up. Best offer I got from my process post was like a 275 million valuation instead of 500. I went to founders. I told them everything. It's like, here's how I screwed this up. Best offer I got was 275, but the firm wants board control. If you'll just do it without taking the control of the board, you guys can have it. And Peter just offered 300 instead of 275, 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.

Ryan Petersen β€” VC Rumor Mill

I was pitching this investor and I told the guy I've decided to go in a different direction, this isn't going to work out. Within an hour I got phone calls from like three other funds. Well, I hadn't picked a different investor. The amount of rumor mill and collusion that happens in VC founders have no idea. The associate WhatsApp groups are so pernicious β€” they exchange currency. I'm putting you in my weekly update where I said, "Ryan, only at a million, not growing that fast, not a compelling sales round." And these are cross firm.

It's crazy that they're sharing that externally. The associates are more in business with that class than they are that firm. And they're trying to get ahead within the firm. My competition is not the other associate at X firm, it's the other associates in my firm. So if I can get out ahead. Founders should basically never share their metrics. Once you've shared a metric, you're now committed to that being the metric. Maybe you couldn't make that one go up hockey stick style, but now you're committed.

β–Ά 03 πŸ“ˆ Flexport Growth & IPO Plans
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When you extrapolate that out, you said 450 to 600 and then you can be 750. Do you worry about the constraining exit landscape? When you look at IPOs today, unless you're mega scale, you don't want to go out. With the greatest of respect, strategic buyers are less present than ever before. And then you've got buyout firms which are running for the hills because the Medallias and the Coopers and the Anaplans of the world are all bluntly looking pretty precarious right now. Do you think that's a concern that should be felt?

I don't think about it at all for flexport. The word exit implies that I'm going to stop working. So I don't think of it in that term. Do you want to take the company public? Yeah. Yeah, we intend to go public. I don't know what the valuation is or should be or will be. If we can just keep growing, you just draw the math out. When do you think you should go public then? I'd like to be a nicely profitable making a few hundred million of EBIT then we'll go public. So, it could happen in a couple years. It should β€” the way that things are going right now. We should be able to get there.

Do you think you should underprice on IPO day so you have the pop or you should price to perfection? People focus so much on this. I don't understand it. There's this concept of like an IPO window that investment bankers and founders talk about. "Oh, the window's closed. You can't go public." But what if you went public and then your price went down? Is that better? It's the same thing, isn't it?

Do you worry about the concentration of value to a few companies when you look at eight companies making up 85% of year-to-date gains in the stock markets and then you look at Anthropic and OpenAI? As long as I'm allowed to use OpenAI and Anthropic, then I don't mind at all. They deserve it. These things are just incredible, miraculous products. What I worry about is that they cut us off and then we can't use it anymore. If I can't use OpenAI, we're all going to go back to being just idiots we were two years ago. We're so dependent on it both personally and we've put it into so many of our processes.

We're an enterprise logistics company. We help businesses manage their cargo shipping around the world. And every business is unique and has their own process. Some companies want to be notified 10 days in advance of their container arriving at their warehouse and 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. 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. And RPA couldn't do that before β€” agents can go all the way. We think we can automate the full end-to-end.

We're using OpenAI, 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. Did you see that article the other day? It's like we spent half a billion dollars β€” kidding me. We do not have a budget on our contract. And yet last Thursday I woke up and they said your organization has reached your limit for the month, which is not true β€” something went wrong on their side. But I had this shock moment of like oh man what if they just decide one day to cut us off. I actually think this is a realistic scenario where they decide the compute that they have is more valuable for training super intelligence 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.

How much is it? I think we're spending like probably like 5 million a year or something. Ramping pretty fast though. It's doubled in the last few months. We released a show with Brandon at McKay and he said he spends more on Anthropic or OpenAI. He spends more on models and compute than he does on salaries by far. 20 million a year on Anthropic in 5 years? Yeah, probably. I mean I don't know about Anthropic but on LLMs. But it's possible that price comes way down deflation and there's it's also possible that we move a lot of workflows onto open sources because if it's good enough for our coding agents and for actually developing product we probably always want the frontier model. But if you're just automating a workflow, if the open source one is basically free and automated then there's diminishing returns to Frontier Labs.

What's your largest customer? Like not name, size. Uh 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. Logistics is expensive. It's 11% of GDP. People spend and these aren't they don't have to be that big of a company. Logistics is a much bigger market than software. A typical medium-sized company will spend about 5% of their revenue on logistics if they're physical goods companies. They're not spending 5% on any software. Maybe at scale like we are, our price point is similar to what you would spend on Oracle for a comparably sized company but actually less.

But you would say that we are not seeing the productivity gains in logistics that we are seeing in software creation because if we were you'd be seeing revenue scaling in logistics like you have done for a cognition or a cursor. You see cost come down at least. I don't know that you're going to see a huge revenue scaling. By the way, our competitors and others that are scaling that are serving data center companies β€” that part of the business is growing like crazy because there's data center all this physical the data centers have to be built. The data center economy is wild.

β–Ά 04 πŸ€– AI, Open Source & China β€” CCP Risk
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When we go back to the teams themselves I am intrigued you said about the use of Anthropic. Have you always used Anthropic or has that been a switch? We switch back and forth. We're using Codex too. In fact, Codex won us over. They stole β€” Sam stole 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. The engineers can choose both. They're still more habit formed on Claude, but they use Codex. 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 really nice how baked in it is and notebook LM and these things, but all of our employees have Claude access as well.

You're able to invest in OpenAI or Anthropic. OpenAI is whatever 900 and Anthropic is a trillion. So, slight difference on price. But you can only invest in one. Which one do you invest in? Oh, I can only invest in one. Why? Why can't I invest in both? Because I'm forcing you to choose. It'd be easy if you could choose both at the same price. Let's do same price. Yeah, same price.

Ryan Petersen β€” Anthropic vs OpenAI

I think I'm going Anthropic. No offense cuz Sam's a friend of mine, but just cuz the enterprise business. The enterprise business seems great. And the team, I think there's a lot of value of like this cohesive team that's been together forever. OpenAI's had ups and downs and people have left and it's been hard to keep the whole team in place. There's just so much value in boundaries that love each other and no one quits.

You invest in Anthropic? Yeah. Well done. But not like early. What price did you do it at? No, it's like I forget 600 or something. It was already It had already run away. So, I'm not going to make much money off that. Doing it at 600 is not bad. Well, like 2 months later, I got my β€” it wasn't very long ago. How much did you do? It's my finances are private, but not that much. I don't have that much money.

Do you worry about open source as a threat to Anthropic? Yeah. I don't know, dude. If you think about what you just said earlier, which is a lot of the usage from frontier models can be moved over time for more mundane tasks to open source models. Which we both agreed on that massively names the market for the core providers. If we only use them for the most frontier advanced tasks and everything else we can just push to open source or older models. The core business is much smaller than you think. No, but your question was do I worry about that? I don't care. I mean Anthropic goal to zero. I don't care. I didn't put an amount of money that matters for me. On a personal basis and if AI and intelligence becomes really cheap that's like much better for the world.

The majority of open source models are Chinese. 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 β€” like who cares where they're from like we can use them. Well because you're essentially feeding data back to the CCP would be the fear from Keith Rabois and others β€” that CCP funded open source models are powering the majority of early stage Silicon Valley companies and that essentially is giving a window into Silicon Valley for China.

Yeah, it's pretty interesting. I don't personally spend a lot β€” I don't lose sleep over it. Do you sleep over China? Not really. I lived in China for a few years so and I speak Chinese passably and not really well but I could have a conversation. So I feel like I know China better than most. It's not high bar.

Ryan Petersen β€” On US-China

I think China and the US there's a huge amount of mutual dependence there that is underplayed. The interests are much more aligned than people give credit. There's so much saber rattling and so many people casually throwing around like war between China and the United States without realizing that such a thing would be a nuclear war and you'd all be dead. So I don't really believe that these countries are going to suddenly start shooting nukes at each other.

I loved it when Trump landed in China and they played YMCA. They did. And there's this video of Trump and you can see he's kind of like a little child at a party desperate to dance but not allowed to. Bad protocol. Why MCA playing in the background? Remember when Obama went there, they didn't even open the β€” they didn't roll out the red carpet. They didn't bring up the stairs to Air Force One. You had to climb out the bottom of it.

And when I think about China, I sadly these days think about a mutual friend of ours, Keith Rabois, given his very open concerns around China. Going back to venture and fundraising β€” how you screwed up two funding rounds, very humble of you, and how Founders Fund bailed you out of them. They're both my fault. Well, at least the first one was definitely my fault. (The story above with FF and Peter.)

What's been your biggest lesson from working with Peter? They've invested several times in you. Founders Fund led our A or B, participated in the C or D and led our E. They probably have almost 15% or something maybe 12. There's been some dilution.

Ryan Petersen on Peter Thiel

Just amazing how far in the future he's able to look and like be right. The number of predictions that he's made out there just blow your mind. 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. If you accelerate your speech with him, I think we talk like two times faster than when we talk to other people. And there's never a moment where he doesn't understand what I'm trying to say.

I care a lot about word to value ratio. The people who take a very long time to say quite a simple message and you're like, just say the thing. Drives me crazy.

β–Ά 05 🏒 Remote Work, HR, CMO & SaaS Apocalypse
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Do you find that hard? The hopping that seems so prevalent today more than ever. So, it seems like there's a lack of loyalty. For sure. We basically moved away from San Francisco as a result. Our team in San Francisco is maybe 4% of the company's based in San Francisco even though that's where we were founded and where I'm based. I sort of I think maybe we overdid it because of cost. Loyalty retention of good people has always been really hard. And acquisition and respectfully you're fighting against OpenAI Anthropic and some of the hottest companies on the planet β€” as great a business as you are, you're not as sexy. Our customers aren't there so I don't need a big sales team in San Francisco. We need to be everywhere. So, I think we maybe overdid it. Six years ago, I had 100 people in San Francisco. And right now, we're down to about 75. Actually I'm pushing more of our employees, "Hey, you should come move back to San Francisco." I just got our CFO to move to San Francisco. It's made the business much better.

You said remote work is what? Dot dot dot. Can you help me fill in the statement here?

Ryan Petersen β€” Remote Work

I say it's white collar fraud. I have a three-year-old and a 5-year-old. The idea that I could do any work at my house is like a total fantasy. Like, come on. You're kidding. I have a bigger house than most employees do. I actually do have a private office I can close the door on. It doesn't matter. There's no work getting done at that house when the children are around. The kids come home at 3 pm β€” your workday needs to keep going. I'm highly against it. We're 5 day a week in office as the baseline assumption at our company. I made the mistake during COVID of going remote and letting it stay remote for way too long.

Was it difficult to bring it back in? Difficult for the people who don't work here anymore. But a lot of founders are sitting in the seat today going, "Man, I want to bring it back. I want in person. I know the value of in person, but I don't want a revolt." You just got to do what you want to do. I think all the bad things that have happened at Flexport were when I didn't do what I wanted to do. You don't want to ever be afraid of your employees first of all β€” the employees don't want that either. They want a leader who's going to go in the direction that they believe in. Even if they disagree, they want to follow a good leader. And if they opt out, that's fine.

The idea that work from home is going to benefit highly paid employees is sort of a total fantasy. Work from home done correctly, you should be hiring the world's greatest geniuses. There should be a labor arbitrage where you're finding really really smart people who make a lot less money because of the way that our economy is structured where some countries just have a lower purchasing power. My brother has an assistant who has like off the charts IQ in the Philippines and makes like 500 bucks a month. That's who's going to benefit from a work from home environment. It's not the guy who's making 250k a year and lives in Jackson Hole and wants to go skiing for 4 hours a day.

Look your podcast is better if we're in person. I'm way better. It's the exact same with every meeting. I struggle and we struggle because we're still distributed. We have 40 offices. We need to be in every country. So I struggle personally with paying attention in video meetings. I don't really do Zooms anymore because the quality of interaction is so low and I'm so disengaged. I do want more of our talent to come back to SF.

I want to ask going back to β€” you should never hire execs. Most startup founders. I just consistently see I saw this the other day with this founder of a really fast growing company and they hired the CMO from one of these big logoed companies and I go to the CMO's Twitter. They don't have Twitter. CMO doesn't have Twitter. And it's like the most enterprise CMO ever. Marketing is the hardest thing to hire for too. Marketing and HR.

Why is marketing and HR the hardest to hire for? In enterprise marketing, the moment something works, it stops working because your competitors will copy it. It's all about creativity and originality. How do you get creativity and originality in B2B enterprise marketing? If you are creative you probably kind of become a founder if you can get do good storytelling and creative idea ideation in the marketing storytelling angle. You have to be doing kind of crazy stuff. Most crazy ideas are bad ideas. So you want to do crazy things that happen to also be good ideas. It's that narrow intersection. As an employee it's so hard to take that risk because you're like I don't know if I do something crazy and it blows up I get fired. Why take the risk? The big benefit that a big brand has is they can just do really expensive stuff. Expensive is a feature in enterprise marketing because you wouldn't spend a lot of money on something promoting something if it wasn't good. So, it must be good.

Ryan Petersen on HR

The thing that you cannot have is them being like union representatives of your employees. They're to represent the company and therefore the CEO. If you don't have that as a CEO, 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. The employees are the company and the company is the employee. Everything else is a fiction. Humans are not a resource that you can mine and take out of the earth β€” you have to give back to the employees.

They're not. But agents are resources. True. That you mine and agents will in large part replace humans. The really interesting job function that could be created is like agent resources. That is a good idea honestly. 996 is being replaced by 007 which is midnight to midday 7 days a week which is your new agent timeline.

Do you buy the SaaS apocalypse? You said earlier that you've built agents for a lot of workflows. Have you ripped and replaced Salesforce, Cooper, and built your own SaaS tools? Some. Not those names in particular, but yeah.

Ryan Petersen β€” SaaS Apocalypse

I think the negotiation that we're going to have with Salesforce is going to be a lot different than the last one. I think selling SaaS to tech companies is going to be a tough business because we can build stuff ourselves. Salesforce is great. Although most of our people don't like Salesforce. How much do you spend on Salesforce a year? A few million. It's on the list of candidates. I suspect we'll be replacing a lot of these things and a lot of what'll happen is you'll just shake them down.

I don't know about Salesforce. Salesforce Slack is also going to be a great turn out to be a great acquisition because 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 raised the rates on Slack. We actually incubated a company which is a Slack competitor. A direct Slack competitor built for the AI. Predicated on Alex Rampell from Andreessen β€” green field bingo, markets where there's a huge amount of net new customers created every single year. Our market is every new startup that's ever created. If you're creating a company, do you want to go on to like Slack and Salesforce or do you want to have an amazing AI first messenger? That makes sense.

One of the things I'm having our procurement team do is make the PowerPoint case study of one of the SaaS that we did replace and how we did it and how long it took. Then 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 replace you guys." What is that reduction? I think you get like 20% out of almost everybody. Do you worry about maintenance? Yeah, that's why I don't want to have to do it for a lot. Some cases it might be a bluff. I couldn't do it for all of them. I don't want to dedicate that much of our engineering resources to replacing SaaS. I want to focus on our core business with our engineering talent. You worry about security? Constantly paranoid. Almost all of our competitors have had major hacks in logistics. It's been a major target area for cyber and there's been a lot of ransoms.

β–Ά 06 🎯 Angel Investing, Masa, Marriage & 2026 KPIs
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I'm not going into personal finances, but I didn't know before we walked in the park about the angel investing. If you're comfortable sharing β€” what have been some of the best angel checks? I've done really well as an angel investor. I used to do a ton of it. Early days of Flexport. I started this company called importgenius.com that throws off a lot of cash. So I actually started as an angel investor while I was in Y Combinator because I realized I had inside access. I invested inside my own batch β€” I invested in like 13 of the 50 companies. There were a few good outcomes. Algolia I was an investor in. I missed Cruz. I sold my shares in Algolia a while ago. I made money on that one.

You missed Cruise? Yeah, I'm friends with Kyle. I don't know β€” he was just throwing this camera setup on the roof of his Honda Civic. I was like this is not legit. The crazier the thing the more I'm like I need to do that. Because if I don't get it I'm probably missing something. What are my best angel investments? Bitcoin β€” early Bitcoin. Sold that. Don't kidnap me. I don't have any Bitcoin anymore. I was the first investor in Rippling. Put a big check into that. Did really well. Are you revengeful? No, I'm personally not. But I think that investing in founders who are pissed at somebody and want to get back at them β€” like Rippling, Parker, A16Z fired him.

Ryan Petersen β€” Investment Thesis

I have a great thesis around founders who have been wronged. Second time founders who feel like they were wronged the first time around would be a great investment thesis. Revenge and patriotism is a great investment thesis.

How many angel investments have you done? I did so many. The vast majority didn't do well. Like 200. Yeah, something like that. I have a Google sheet now. I made one when I was getting married and going through that exercise. It's super power law world. This is an interesting thing for founders to understand β€” once you see the world from the perspective of the angel investor, you realize that we really don't care. Even a 3x β€” like if you take my spreadsheet and this investment made three times the money, the founder is very proud, but if I remove that and make it a zero it has zero impact on the bottom line of the fund. Zero relative impact on the IRR because I have a couple that are a 1000x or 500x. They strictly dominate everything else. So you don't care about the ones that failed. When I write a check as an angel investor I just mark it to zero. That way I don't worry if it fails.

What do you think founders don't know about the VC mindset that they should do? There's the noble founder mindset which is I'm going to give 5 to 10 more years of my life to grind out a 1 and 1/2x. I don't even want the investor updates. It's fine, dude. Return 0.6x, it's better. I mean, if it's your life's mission and your calling, then great. Never give up.

What was the single best investor meeting that you had where they didn't invest? None of them. I've never had one of those. I had like a lot that seemed like they went well and then they never invested. The number of investors who ghosted me, the vast majority. I would say, where I pitched them, it seemed great and then just never hear from them again. I walked out of one investor meeting. Um, not like in a huff. I left my co-founder there. I said I had to take a phone call and I just never came back. Why? They kept telling me that the market size was too small and it was like the third pitch where after the first two I thought we'd overcome this. They brought their own report that showed how the market size was only for Flexport was only $6 billion. My partner had the best line. He was like, "Oh, so it's smaller than the market for USB cables."

I always say to founders, if you need to educate an investor on market, they're not the right investor for you. Peter β€” Sam Altman introduced me to Peter. Sam was one of our earliest investors. He invited me to Peter to get advice. It was a classic thing cuz everyone loves his book, right? 0 to 1 is such a great book. There's six or seven questions to decide if you'll change the world. On five of the six questions I felt like Flexport knocked it out of the park. But then one of them is β€” is it a small market? His whole thesis was you should have a market that's small enough that you can be a monopolist. When I went to whiteboard with him, I'm like, "Well, look, I can make this a small market and be like, oh, we're going to dominate logistics for hardware companies in Silicon Valley, but it's kind of fake. 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." A few weeks later he emailed asking if he could invest.

Final two for you and they they are more personal but I hope it's okay for me to ask β€” but it's general wisdom for me moving forwards when you think about winning at marriage. Any tips on how to continuously have a great marriage? You've been through some rocky patches in terms of the business β€” how to sustain marriage through hard ups and downs. 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 is β€” when I met her, she was a journalist actually at Bloomberg and I still couldn't kill that Bloomberg story even though these were her peers that she worked with for years. It was crazy even then. It was a risky move. I know. I don't talk to journalists. It was a bit β€” in fact 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." He's right. Great advice. So, I married her. And then she had to quit. In part because of me β€” she got assigned to cover SoftBank who's my investor and I was like, "No, can't do it."

What has it been like having SoftBank there? I love Masa. How did you pitch Masa? I love him. He's just like a big larger than life. Where was it? First time I met him would have been at his house in Woodside, California. You can look up the Zillow estimate. How long was the meeting? Probably actually pretty short. 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. I was trying to buy a painting of the Duke of Wellington to send it to him β€” who of course defeated Napoleon, but as a troll. But I never found a good one. He's very bold. He wanted me β€” he pushed us to go, hey, drop your prices, be cheaper than everybody because we raised a billion dollars from them. 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 β€” 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. He's very connected, too. He was able during the meeting to call Foxconn, get him on the phone, be like, "Hey, what do you think of this thing?" Live. His guy next to him called or WhatsApp.

When have you been most nervous in the Flexport time? I get nervous when I have to give a talk publicly and it's very time bound cuz I'm kind of long-winded. I can't memorize anything. So I usually just go speak off the cuff. The most nervous I ever was was the Y Combinator pitch cuz I only had 2 minutes. I find TV most nerve-racking because they don't want to help you out. Do you think founder brand matters? 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 do more press. They say that it helps them get deals and close deals. Steve Martin said he went on the Tonight Show, every late night show that would have him, and then he would walk around Hollywood and nobody would recognize him. He couldn't tell if it was having an impact. And then after five years of that, he was like the most famous comedian in America. Generally I think being famous has helped Flexport a lot. We're way more famous than we should be given that we're like the 10th largest freight company.

Final one, then we'll do a quick fire. You mentioned two kids, five and a three year old. Any big lessons on parenting? I love kids. It's really important I'm a good dad. Well, you need to have a great wife who's a great mom. If you have a good partnership, the kids will be pretty natural. You've had millions of years of evolution. It'll be great to finally care about someone besides yourself. It's like a chemical wash of just like true love. You can't get it anywhere else. Does it change perspectives? For sure. I get a lot of meaning from my work β€” I genuinely love what I do. It's a real mission for me. My life's work is building Flexport. But a lot of people don't have that. I was always kind of confused cuz most people I meet don't have a sense of purpose about their work like I do. As soon as you have kids you will get more purpose from that than I could from Flexport. So the vast majority of human beings should get their purpose from their family.

What have you changed your mind on most in the last 12 months? For the last decade, I wanted to be the premium value provider in logistics and thought it would be bad to compete on price. Now I'm pretty convinced that we need to be the low-cost leader and just go so hard at lowering our costs that if you're cheaper, you just take all the market. 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. 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.

Who do you not have on your board that you'd most like to have? I don't think our Flexport board needs anybody. The board is mostly there to represent the interests of the investors and make sure we're doing a good job. I'm just glad that my board doesn't screw with us. My board has been very supportive of me in particular. I don't really want a more active board. They're not telling us what to do. They don't help that much, but they don't ever hurt. 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.

Penultimate one. What sports team do you not sponsor that you would most like to sponsor? Oh. I really would love to sponsor this football club in Hamburg called St. Pauli. Why? They're the second team in Hamburg. My great-grandfather was a sailor from Hamburg. The first team is owned by Klaus-Michael Kuhne, who's the owner of our direct competitor, Kuehne+Nagel. I just love the idea that we would take the second team and beat him and he would be like, "Ah, those damn kids, here they come again." Just more of a troll than anything else. Their logo is a pirate. They're like a leftist communist-oriented club. I think they would kind of hate us if we tried to buy them. Sports is a tough business. I don't want to own any teams.

Ryan Petersen β€” 2026 Success Criteria

We got to hit our numbers. We got to grow like crazy. And then this automation via AI β€” we've got probably like a hundred core workflows that are costly that we have AI agents for right now. Five of them are live and working and saving us money and 95 that are under development. I need at least 80% of those to come to life and actually have the impact. Otherwise, we're just spending money and not getting much back for the AI.

Dude, it's been so great to have you in person. Thank you so much for doing also on a Sunday of all time. So, I really appreciate it, dude. And it's really special to meet you in person properly. Yeah, it's great to be here.