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Flexport CEO: Why Revenge and Patriotism are the Best Founder Traits

Ryan Peterson is the Founder & CEO @ Flexport, the logistics darling of the venture capital world that has raised $900M+ with the last round valuing the company at $8BN. Today, the company does $450M in revenue growing 30% YoY. ----------------------------------------------- Timestamps: 00:00 Intro 01:22 Fear of Losing vs Thrill of Winning 03:26 Why VCs Are Herd Animals 06:49 Living on $250/Month in China 18:23 Is AI Productivity a Myth? The Manual Labor Reality of Logistics 21:17 Codex vs Claude vs Gemini 26:13 Would You Invest in OpenAI or Anthropic? 27:33 Does Open Source AI Threaten the Frontier Labs? 32:57 The Founders Fund Story: Peter Thiel's $3M Bet 41:27 Why You Should Never Hire a Traditional CMO 44:48 "Every Great CEO Hates HR" 46:25 The SaaS Apocalypse: Has Flexport Replaced Salesforce? 50:26 Ryan's Best Angel Bets: Rippling, Bitcoin & Missing Cruise 58:31 Peter Thiel's Zero to One Test: How Flexport Beat the Monopoly Rule 1:00:57 What Founders Get Wrong About the VC Mindset 1:02:06 The VC Rumor Mill: How Associates Trade Gossip on Founders 1:04:19 Why Founders Should Never Share Their Metrics 1:10:49 Pitching Masayoshi Son: $1B in an Hour & Calling Foxconn Live 1:17:23 Quick-Fire Round ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on X: https://twitter.com/HarryStebbings Follow Ryan Petersen on X: https://twitter.com/typesfast Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #founder #entrepreneur

Harry StebbingshostRyan Petersenguest
Jun 20, 20261h 20mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 1:22

    Intro

    1. HS

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

    2. RP

      Uh, well, I got- I, I say, 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.

    3. HS

      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 at risk, why remote work is like white collar fraud, and so much more.

    4. RP

      I think the negotiation that we're gonna have with Salesforce is gonna be a lot different than the last one. I think selling SaaS to tech companies is gonna be a tough business, 'cause we can build the stuff 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 [chuckles] than with their own partners.

    5. HS

      Ready to go? [upbeat music] Ryan, I cannot wait for this. Dude, we've done this a couple of times remote, but I feel that it's much more special in person. We're gonna get to remote work, but remote interviews are not as good as in person, dude, so thank you for being here.

    6. RP

      Yeah, it's great.

    7. HS

      Dude, I wanna 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.

  2. 1:22 – 3:26

    Fear of Losing vs Thrill of Winning

    1. RP

      Hmm.

    2. HS

      Which one is it for you?

    3. RP

      Probably the fear of losing.

    4. HS

      Hmm. Why?

    5. RP

      I don't wanna be a loser.

    6. HS

      [laughs]

    7. RP

      Well, it's like the wi- you never win enough, right? [laughs] Like, you- I've already won, and yet I still am like, I don't feel like I won. Uh, but by any standard, if I- what I- by any standard-

    8. HS

      [laughs]

    9. RP

      ... of what I set out when I started the company, like, I've won. My, my first Excel f- uh, I've- my first and only financial model that I made for myself for the business got to one million of revenue [laughs] right? And like, we d- did over two billion last year, so.

    10. HS

      I hate Excel models. I am terrible at it. When I open up Excel it says sign in or register, and I'm just like, "I'll leave someone else to do it."

    11. RP

      I'm not very organized, so.

    12. HS

      Are you not?

    13. RP

      No, and like, I feel like making a good model requires you to, like, organize your, organize your stuff.

    14. HS

      So today's rule is we're gonna 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.

    15. RP

      Okay.

    16. HS

      And if I ask a question that someone has asked before, you have to tell me, and I will donate $100 to a charity.

    17. RP

      Oh, wow.

    18. HS

      [laughs] I told you.

    19. RP

      Oh, great. All right.

    20. HS

      I'm very, uh-

    21. RP

      So we're gonna... Do I get to pick the charity? What are we gonna do?

    22. HS

      Sure, you can-

    23. RP

      And what's your charity?

    24. HS

      Um, uh, my mom's got MS. I would-

    25. RP

      Oh, that's great

    26. HS

      ... uh, like to give it to-

    27. RP

      Okay, we'll do that charity

    28. HS

      ... an MS charity.

    29. RP

      God bless her.

    30. HS

      But that's the deal, okay?

  3. 3:26 – 6:49

    Why VCs Are Herd Animals

    1. HS

      interesting we should discuss?

    2. RP

      Um, well, if that i- you know, VC, y- your, your show is called 20 Minute VC, so what's a hot take on venture capital?

    3. HS

      Yeah.

    4. RP

      Um, the, the nature of the job is simply that it's just such a good job. Uh, it pays really well. Like, if you were listing, if you were listing, like, okay, what... If someone who likes to have a job, what, what would be the attributes? Like, pays really well. You basically don't have a boss. You're, once you're, like, a partner or, like, at some, some level of seniority, you have no boss. Pays well. You don't have to be anywhere on any given day. There's, like, kind of not a fixed schedule, and it's very hard to measure if you're good or not on any reasonable timeframe. So, like, you can't get fired. Pretty, these are pretty good attributes of a job. So, like, therefore-

    5. HS

      And security.

    6. RP

      Yeah, that's what I mean. You can't get fired.

    7. HS

      You know, fund fees f- for 10 years.

    8. RP

      Right.

    9. HS

      And not only can you not get fired, but, like, uh, dude, I run a media company, you run a, a company. Uh, revenues can go down. They are not certain. You know, fund fees are, are, are legally, you know, structured.

    10. RP

      Mm. Yeah. Yeah, so, so you have to, if you're in a m- if you are a partner... Now, if you run the fund, that's one thing, but if you're, like, in, a partner that's doesn't own the fund, you could get fired. So you don't have infinite job security. So your whole thing has to be, "How do I avoid getting fired?" Like, so, uh, you know, you can do this in reverse or invert the p- invert the problem and you go, "Well, how would you get fired as a VC?" Okay, like scandal [laughs] 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, yeah, or they could be great deals. Uh, they, you, 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 cons- you're gonna get consensus, right? And if you're, you're also gonna channel check all your deal- you're gonna, like, check with your competitors. There's a lot of collusion in VC. Like-

    11. HS

      Yeah

    12. RP

      ... VCs are constantly talking to each other, in part 'cause they need to make sure that they don't step out on the edge and do something that their own partners are gonna think are dumb. Like, I have a feeling that most VCs actually collude more with competitors [chuckles] than with their own partners, 'cause they don't want their... They, they need to m- spot check their deal and make sure it's good before bringing it to the other partners [chuckles] to make sure that they're not seen as being dumb. So that's where you get the herd be- behavior.

    13. HS

      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.

    14. RP

      Oh, yeah. Okay, good. Yes, he's, he... See, I think Founders Fund, and Keith was at Founders Fund for a while. Either there's a few funds that avoid this type of behavior somehow, or some people are just born into it With that contrarian bone in their, you know, butt

    15. HS

      Do you think you can only do stupid or crazy shit because you have money now?

    16. RP

      Me personally?

    17. HS

      Mm.

    18. RP

      I don't have that much money. [laughs]

    19. HS

      [laughs]

    20. RP

      So, um-

    21. HS

      But you don't need money. I don't, you know

    22. RP

      No, I have enough, I have enough

    23. HS

      Yeah

    24. RP

      Yeah, yeah

    25. HS

      Like, when you're paying rent and school fees and it's like, "Oh, God, fingers crossed." Like, I think that richer investors make better investors.

    26. RP

      Mm.

    27. HS

      And you're like, "Mm, what?" Like, Sequoia are focused on upside maximization. How big could this be? They are not fearful of LPs coming back for their next fund.

    28. RP

      Mm.

    29. HS

      They're not fearful of deployment speed compressing, so you know, they, they elongate it. They just invest in what they think can be mega

  4. 6:49 – 18:23

    Living on $250/Month in China

    1. HS

      fucking companies.

    2. RP

      When, when I, um, 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 weren't, 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, uh, apartment in a nice part of a second-tier city, but it was, like, a nice... And so I knew, like, that actually gave me a lot of permission to be an entrepreneur, uh, and to, which was kind of being crazy, doing crazy stuff, because I knew I could live off of... If I could make 500 bucks a month, I could survive. Uh, and I knew I could always make 500 bucks a month. So, like, I could do a startup. I could do, I could take risks 'cause I'm like, worst case, like, I lived in a nice apartment in a nice town. I had a good quality of life. My total OPEX was, like, $250 a month, like, so it gave me permission, yeah, to take some risk. But it's the opposite. I'd have to be, I was relatively rich, right? Or, like, relatively secure.

    3. HS

      What's your, what's your number?

    4. RP

      What's that mean?

    5. HS

      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."

    6. RP

      Oh.

    7. HS

      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 [laughs] you know, mentally.

    8. RP

      Well, this is how you know money is amazing, because, uh, the more you have, the more you want. You can never satiate the human desire. It's infinite.

    9. HS

      Do you find that? 'Cause I don't.

    10. RP

      No?

    11. HS

      Uh, no. Like, of course you want more, but, like, I only buy trainers. Like, I would much rather have more convenience than more money.

    12. RP

      Yeah. I mean, I, I haven't been that motivated by money. I, I, I'm more into, like, uh, power. [laughs]

    13. HS

      [laughs]

    14. RP

      I wanna do big things.

    15. HS

      That's really interesting. You know, there's, uh, 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?" Uh, maybe you're more adjusted than me. I said I'd go down 90%. [laughs]

    16. RP

      [laughs]

    17. HS

      No, I do, but m- mine is, like, my work is directly correlated to the financial outputs that you have, like, candidly.

    18. RP

      Mm.

    19. HS

      If you are a general in the army, your success in your profession does not correlate to your financial s- statement at the end of the day. I'm a venture capitalist.

    20. RP

      Yeah.

    21. HS

      The clue is in the name. If you're good, you make bank. If you're not, you don't.

    22. RP

      Yeah, but it's, you know, you gotta forget the, [laughs] forget the past and the future and, like, the future, y- y- the future's not written, so you can go make it.

    23. HS

      If Flexport were to raise today, what do you think you'd raise at?

    24. RP

      I don't know. I really don't know. Uh, I think this year we're gonna get to basically break even. We're on run rate to do about f- $450 million of revenue, net revenue. Sh- breaking news here, I haven't shared that, but $450 million of net revenue.

    25. HS

      What's your growth rate?

    26. RP

      Last year was 350, so...

    27. HS

      350%?

    28. RP

      No, $350 million last year. So what is that?

    29. HS

      Okay, so-

    30. RP

      100, about almost 30%.

  5. 18:23 – 21:17

    Is AI Productivity a Myth? The Manual Labor Reality of Logistics

    1. HS

      Do you not think actually though you're extrapolating it a bit far given the fact that I can't even do fucking clips on AI right now? Like [laughs] th- this is my point, like-

    2. RP

      Not yet.

    3. HS

      No.

    4. RP

      They can't do your-

    5. HS

      And you know, you're seeing Uber and Microsoft come out saying, "Yeah, the productivity gains are kinda questionable."

    6. RP

      Yeah. I, I think that's probably true in, in b- like those, 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, 'cause it's like people passing PDFs around and moving data between enterprise systems. And there's just like a hu- a huge amount of human labor. And I think that most of the economy looks like that, not like Uber, which a highly automated built business. Although, I don't know why they have like tens of thous- 30,000 more employees because it's pretty automated, right? Like, I don't quite get that.

    7. HS

      You said the team is 2,000?

    8. RP

      Almost.

    9. HS

      Almost 2,000.

    10. RP

      Yeah.

    11. HS

      2030, four years' time, how big is the team then?

    12. RP

      It'll, 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 gonna see like a shift from people that today do operations, kind of manual work that I was describing earlier, into, okay, you've gotta... The work style is gonna change. And, and if the people are not able to make that shift, then we're gonna have to rebalance. But like, into much more customer facing, account management, sales, kinda like, all right, how do you... Because I think that, that's the future is just like people-

    13. HS

      Do you not think the future is super contributors? And I don't see people talking about this enough. Zab from ClickUp said this in his post, which-

    14. RP

      Mm

    15. HS

      ... uh, we, we chatted about before. [laughs] Um, but he ba- essentially said he was cutting people so he could pay the super contributors 10X more. You don't need more, eh, salespeople. You need more fucking amazing salespeople who leverage AI, outbound AI tools, inbound AI tools, pipeline tools, forecasting tools to be the next great sales leader that leverages AI.

    16. RP

      Certainly want as many of those people as you can get.

    17. HS

      Yeah. [laughs]

    18. RP

      Um, there's just like a lot of mass that you want out there in the field. I mean, our... 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 ha- can have. And I think you can probably use those t- 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, it's a relationships game at the end of the day, sales. And so I'm, I'm somewhat skeptical. Yeah. It is an interesting question though. Like Yelp has 3,600 salespeople, um, calling on restaurants. It's actually a pretty good business. I think, uh, they're, they haven't grown that much, but they print cash. And like 3,600 salespeople, if Yelp can have 3,600 salespeople, like

  6. 21:17 – 26:13

    Codex vs Claude vs Gemini

    1. RP

      I feel like we should have-

    2. HS

      I interviewed the founder of Invisible, which is another data provider.

    3. RP

      Mm.

    4. HS

      Um, and he said that you can't do enterprise without a fully fledged FDE model. Do you think that's true working with some of the biggest companies?

    5. RP

      No, it's not true. You can do it without that, but you, your business is better, but I, I, if you can get that level of integration. You know, the freight, freight industry was the original FDEs. Uh, they just weren't engineers. They were just d- but I met, uh... I mean, one of the big tech companies that runs like a hyperscaler, let's call it, um, has, one of our direct competitors has 130 full-time employees that work at that company, that have badges, that show up to work every day, that run their logistics for them. And we cannot crack the door at that place. I won't say their name, but we cannot get our foot in the door because all the decision-making is done by our competitor. I think it's an insane, what an insanely great competitive advantage and positioning to have that, so I'm jealous. And I don't know where you find... But they're not software engineers. These are just like logistics people. Um, if you can get that same thing and just deeply embed yourself into the process workflow of a company, it's so valuable. It's not easy to do. And like, it's not easy to find in the FDE model to find good FDEs who will like, uh, uh, know what to do. Like show up and do a good job every day and like stay in the job and not have the turnover and-

    6. HS

      You also have like a question of like do truly great engineers wanna be FDEs? It's not-

    7. RP

      Yeah

    8. HS

      ... often as close to the pure art of solving engineering problems that they want or great engineers want. It's challenging.

    9. RP

      Yeah. The actually, speaking of the, um... So a different-- It's quite common in our industry where you have these like forward deployed, they're not engineers like I said, they're like forward depl- 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, um, I was like, "Wow, this is great." But I had heard that our competitor makes their, has one of these forward deployed logisticians, like, and runs their RFP, runs their process for choosing a freight forwarder, and they always choose themself.

    10. HS

      [laughs]

    11. RP

      Which I'd heard about and was like, "Wow, this is idiotic." Like, "Why do they do this?"

    12. HS

      It's a great business. [laughs]

    13. RP

      Totally.

    14. HS

      Like today I'm gonna choose me. [laughs]

    15. RP

      Yes. And we won, and I was like, "Wow, what happened?" And then I found out-

    16. HS

      You dogged. [laughs]

    17. RP

      ... the competitor had been acquired by their, 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 sh- chose us to get back at them. So-

    18. HS

      Wow

    19. RP

      ... never, uh, underestimate kinda corporate incompetence and-

    20. HS

      What's your largest customer? Like n- not name, but like size.

    21. RP

      Uh, spend about 150 million a year. The biggest one.

    22. HS

      100-

    23. RP

      We don't have too many like that, but we have probably a dozen that spend over 50, and then a long tail.

    24. HS

      Wow.

    25. RP

      Yeah. Logistics is expensive. It's 11% of GDP. So people spend com- and these aren't, they don't have to be that big of company. I think that- that's the thing that I will often have to educate investors on, is like The logistics have much bigger market than software. If you, for example, like a typical, like a medium-sized company will spend, call it 5% of their revenue. P- companies spend about five-- If they're physical goods companies, they'll spend like 5% of their revenue on logistics. They're not spending 5% on any software. You know, maybe like at scale, like we, we... Our, our price point is similar to what you would spend on Oracle or something for a comparably sized comp- but actually less like-

    26. HS

      But then you would say that we're not-

    27. RP

      Oracle would be less

    28. HS

      But then 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.

    29. RP

      You see costs come down at least. Um, yeah, I don't know that you're gonna see 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 there's data center, all this physical... The data centers have to be built.

    30. HS

      The data center economy is fucking wild.

  7. 26:13 – 27:33

    Would You Invest in OpenAI or Anthropic?

    1. HS

      You're able to invest in OpenAI or Anthropic. OpenAI is whatever, 900, and Anthropic's a trillion. So there's slight difference on price.

    2. RP

      Yeah.

    3. HS

      But you can only invest in one. Which one do you invest in?

    4. RP

      Oh, I can only invest in one? Why?

    5. HS

      Yeah.

    6. RP

      Why can't I invest in both?

    7. HS

      Because I'm forcing you to choose.

    8. RP

      Oh.

    9. HS

      It'd be easy if you could choose both. [chuckles]

    10. RP

      At the same price? Let's do same price.

    11. HS

      Yeah, same price.

    12. RP

      I think I'm going Anthropic. No offense, 'cause Sam's a friend of mine, but...

    13. HS

      Just 'cause the enterprise business?

    14. RP

      Yeah, 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, and OpenAI's 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 in like founders that love each other and no one quits and-

    15. HS

      I totally get that

    16. RP

      ... the talent density, et cetera. So...

    17. HS

      Do you worry about-

    18. RP

      OpenAI has like people sleep on. I would invest in both, right? Like, and I have, uh, I would do as much as I could into either of them.

    19. HS

      You invest in Anthropic?

    20. RP

      Yeah.

    21. HS

      Well done.

    22. RP

      No, but not like early. I'm not like, uh, I-

    23. HS

      What price did you do it at?

    24. RP

      No, it's like, I forget. 600 or something. It was already, it was already, it already ran away, so I'm not gonna make much money off that.

    25. HS

      Doing it at 600 is not bad.

    26. RP

      Well, like two months later, I got my... It wasn't very long ago. I just recently-

    27. HS

      How much did you do?

    28. RP

      That it's, it's... My finances are private, but not that much. I don't have

  8. 27:33 – 32:57

    Does Open Source AI Threaten the Frontier Labs?

    1. RP

      that much money.

    2. HS

      Um, do you worry about open source? And when I said worry about-

    3. RP

      Uh, worry about it as a threat to Anthropic?

    4. HS

      Yeah, well, no, I-

    5. RP

      I don't care. Uh, that'd be great

    6. HS

      ... no, I say I... I don't know, dude. If you think about what you just said earlier, actually, which is a lot of the usage from frontier models can be moved over time for more mundane tasks to open source models. Yeah? Which we-

    7. RP

      Yeah

    8. HS

      ... both agree on. That massively maims the market for the core providers.

    9. RP

      Yeah.

    10. HS

      If we only use them for the most frontier advanced tasks-

    11. RP

      Yeah

    12. HS

      ... and everything else we can just push to open source or older models-

    13. RP

      Yeah

    14. HS

      ... their core business is much smaller than you think.

    15. RP

      No, but your question was do I worry about that? I don't care. I mean, Anthropic go to zero, I don't care. It's, I didn't put ano- an amount of money that matters for-

    16. HS

      Okay

    17. RP

      ... for me. So on my personal basis. And if, and AI and intelligence becomes really cheap, that's like much better for the world and for me.

    18. HS

      Do you, do you worry given the majority of open source models are Chinese?

    19. RP

      Um, not really. I, I don't know how they work, like how they can stay competitive on some level. Um, but if they're open source, they're open source. Like who cares where they're from? Like we can use them.

    20. HS

      Well, 'cause you, you're essentially feeding data back to the CCP would be the fear-

    21. RP

      Mm

    22. HS

      ... from Keith Rabois and others, and that actually 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.

    23. RP

      Yeah. It's pretty interesting. I don't, I don't personally spend a lot... I don't lose sleep over it.

    24. HS

      Do you lose sleep over China?

    25. RP

      Not really. I mean, I think... I, I've lived in, I lived in China for a few years.

    26. HS

      Yeah.

    27. RP

      I and I speak Chinese passively, and not, not, not really well, but I could, uh, have a conversation. A- and so I, I feel like I know China better than most, most, uh, it's not a high bar.

    28. HS

      For sure. Yeah.

    29. RP

      On some level, I think that these, that China and the US, there's like a huge amount of mutual dependence there that is underplayed, and I think that there's a lot... The, the interests align, are much more aligned than people give credit, and all this, these, uh, the, th- there's so much, um, saber-rattling and so many people like trying to sound... I don't know if they're trying to sound smart or tough or something, but they're casually throwing around like war between China and the United States without realizing that like such a thing would be a nuclear war, and you'd all be dead. And, and I, so I don't... I, I think that the odds of that happening are like pretty low. I don't, I don't really believe that these countries are gonna suddenly start s- shooting nukes at each other, and yet if you, if you have war between these two powers, like that's what it would be. So...

    30. HS

      I loved it when Trump landed in China, and they played "Y.M.C.A."

  9. 32:57 – 41:27

    The Founders Fund Story: Peter Thiel's $3M Bet

    1. RP

      this round?" But like I thought I was hot sh- hot and like... Yeah, eventually I did call Founders Fund and told them, "Yo, here's [laughs] where I screwed up. Like, I tried to raise money, failed."

    2. HS

      What did they say?

    3. RP

      Best offer, 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 Founders Fund, I just 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. So if you'll just do it without taking the control of the board, you guys can have it." And, uh, 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.

    4. HS

      What has been your biggest lesson from working with Peter? They've invested several times in you.

    5. RP

      Yeah, they have. Uh, Founders Fund led our A, our B, participated in the C or D, and led our E, so.

    6. HS

      How much, how much of the company do they have?

    7. RP

      They probably, I'd have to go look at the latest cap table, but probably like almost about 15% or something, maybe 12. There's been some dilution, so.

    8. HS

      Okay. But any big lessons from Peter?

    9. RP

      Just amazing, uh, how far in the future he's able to look and like be right. The number of predictions that he's made, like well out there, just kind of blow your mind. That, that's not unique insight from me, but that's one of the things that amazes me. Actually, one of the things I love personally about Peter is that, uh, I feel like most people I talk to talk too slow. [laughs]

    10. HS

      [laughs]

    11. RP

      And Peter does not. Like, and if you accelerate your speech with him, at least when I, when, when Peter and I talk to each other, I, I think we talk like two times faster than when we talk to other people, and there's never a moment where he's like, doesn't understand what I'm trying to say.

    12. HS

      I care a lot about word to value ratio.

    13. RP

      Yeah.

    14. HS

      You know the people who take a very long time to say quite a simple message, and you're like, "For fuck's sake, just-"

    15. RP

      Yeah

    16. HS

      ... just say the fucking thing."

    17. RP

      Drives me crazy.

    18. HS

      Yeah. I'm with you. Should you always take the highest price?

    19. RP

      When fundraising?

    20. HS

      Yeah.

    21. RP

      No. Um, maybe. It depends. Uh... [laughs]

    22. HS

      [laughs] That was the worst. I hate fluff by people who don't get to it. Should you? No. Maybe. It depends.

    23. RP

      Maybe. I, oh, I'm trying to think, like over the years I kind of would always just take the highest price [laughs] and then like if I'm-

    24. HS

      Yeah. But then Brian, Brian Chesky says, "Don't ever take the highest price."

    25. RP

      Don't ever? Mm.

    26. HS

      Yeah.

    27. RP

      That I disagree with. Uh, it could be quite uncorrelated, like the best brand name investor could pay more than the second best sometimes. Like, it's hard to advise. Uh, uh, it's very hard to give generic fundraising advice. I think it's very dangerous. Like each, if a founder asks 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. Um, but I-

    28. HS

      No, I, I disagree totally.

    29. RP

      Yeah.

    30. HS

      Actually, and with the greatest of respect, I actually think there is generic advice which you should listen to.

  10. 41:27 – 44:48

    Why You Should Never Hire a Traditional CMO

    1. HS

      Was it?

    2. RP

      Most startup fou- yes.

    3. HS

      Yeah. And like I just consistently see, I was with the other day with this founder and he just, it's one of the, a really fast growing company, and they hired this CMO from one of these big logoed companies.

    4. RP

      Mm-hmm.

    5. HS

      And I go to the CMO's Twitter. They don't have Twitter. CMO doesn't have Twitter.

    6. RP

      Yeah. Yeah. It's a miss.

    7. HS

      And it's like the most enterprise CMO ever. And I'm just like, "Ugh."

    8. RP

      Marketing is the hardest thing to hire for too. Marketing and HR. Um-

    9. HS

      Well, pause. Why is marketing and HR the hardest to hire for?

    10. RP

      In 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 in B2B enterprise marketing? Like, and it's, and if you are creative, like you probably kind of become a founder if you can g- do good storytelling and creative idea- ideation in, in the marketing storytelling angle. So it's, it's... If you find a good marketer in B2B, you really wanna lock them in and, uh, and get it great. So it's been, it's been a, that's a hard one to hire for. Um, and also To do that, to do like successful B2B marketing and stand out. Like, it's one thing, oh, I just make good sales decks for the team-

    11. HS

      [laughs]

    12. RP

      ... and like, okay, fine, like that's some baseline stuff, but you're not gonna differentiate or move, bend the curve on a star- on a company's success. You have to be doing kinda crazy stuff. Most crazy ideas are bad ideas, so y- you're... It's like being an investor. Like, you wanna do th- crazy things that happen to also be good ideas. Like, it's that narrow intersection.

    13. HS

      Which also don't denigrate enterprise brand-

    14. RP

      Yes

    15. HS

      ... which is even harder.

    16. RP

      Yes. And like as an employee, as a... It's so hard to take that risk-

    17. HS

      Mm

    18. RP

      ... because you're like, "I, 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 m- marketer th- 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, um, expensive, and most 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. And it's, uh, expensive is a feature in enterprise marketing, 'cause 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.

    19. HS

      What's the most expensive thing you've done marketing-wise?

    20. RP

      Well, we d- we don't have money to sp- to waste, uh, on marketing, so

    21. HS

      But you've never spent like a million dollars on big logos, big brand?

    22. RP

      No. I mean, w- a million dollars, sure. We, we, we do, like, a, a conference that costs maybe a, a little bit more than that, um, customer conference. So that's-

    23. HS

      Do you find them effective?

    24. RP

      Yeah, yeah, yeah, for sure. Events like... 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, that's like plain vanilla. But b- by the way, you don't need an exec- you don't need to go hire a CMO to run events. Like-

    25. HS

      [laughs]

    26. RP

      ... conferences are kinda hard to pull off, but, like, normal events like, "Hey, host a dinner," like you don't need marketing at all. Like-

    27. HS

      Yeah, yeah, yeah

    28. RP

      ... just have your sales guy call the people and give him a budget for it.

  11. 44:48 – 46:25

    "Every Great CEO Hates HR"

    1. HS

      Uh, so I basically was doing... I was prepping for a show with Adam from AppLovin, and he's like, "Oh, I fucking hate HR, and every great CEO hates HR." And like a complete dick that I am, I thought I'd front-run his show and take every great CEO hates HR, HR, and I'd tweet it myself. Oh my God, I got killed by everyone for this tweet, which was essentially Adam's words, which I agree with, and I think he's right, and credit to Adam. He's amazing. Do you agree every great CEO hates HR?

    2. RP

      They, 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 there to represent the company and therefore the CEO. And so if there's, 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, like, didn't have the right HR leadership that wasn't focused on the business outcome. Um, and but the employees are the company, and the company is the employee. Uh, 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, the customer. So the, 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.

    3. HS

      They're not, but agents are resources [laughs] -

    4. RP

      Sure. [laughs]

    5. HS

      ... that you mine, and agents will in large part replace humans. And so, like, the, the really interesting job function that could be created is, like, agent resources.

  12. 46:25 – 50:26

    The SaaS Apocalypse: Has Flexport Replaced Salesforce?

    1. HS

      Uh-

    2. RP

      That is a good idea

    3. HS

      ... I, honestly, yeah. Um, it's like 996 is being replaced by 007, which is, you know, midnight to midday, seven days a week-

    4. RP

      Oh, I get it

    5. HS

      ... which is your new agent timeline. Um, do you buy the SaaS Apocalypse? And what I mean by that is you said earlier that you've built, uh, agents for a lot of workflows.

    6. RP

      Mm.

    7. HS

      Have you ripped and replaced Salesforce, Coupa, you name it, and built your own SaaS tools?

    8. RP

      Some. Not those names in particular, but yeah, some. And, and those are, those are, uh... I think the negotiation that we're gonna have with Salesforce is gonna be a lot different than the last one, 'cause we are, I think selling SaaS to tech companies is gonna be a tough business 'cause we can build stuff ourselves. And Salesforce, Salesforce is great, like, although most of our people don't like Salesforce.

    9. HS

      How much do you spend on Salesforce a year?

    10. RP

      A few million.

    11. HS

      A few million?

    12. RP

      Yeah. It's expensive, yeah. So it's on the, it's on the list of candidates for-

    13. HS

      And then it's... 'Cause I just did a show with Fred at Curative. I don't know if you know this guy. Fascinating guy. Loved him. Built a business, a health insurance business in San Francisco. A fucking wild story. Don't know if you know this business.

    14. RP

      Mm-hmm.

    15. HS

      Sold $5 billion of COVID test kits, uh, during COVID.

    16. RP

      Oh, wow.

    17. HS

      Uh, and then obviously COVID, yeah, no longer such a problem. Uh, and now he's pivoted into a health insurance business that does north of a billion in revenue. Like amazing, amazing guy. Uh, and they spent 600K a year on Salesforce, and he replaced it with an inbuilt tool that took three weeks.

    18. RP

      Yeah, yeah, yeah. Um, so I suspect that we'll re- be replacing a lot of these things. And, and I think a lot of what'll happen is you'll just shake them down. I don't know about Salesforce. Salesforce, Slack is also gonna be a great, turn out to be a great acquisition 'cause, like, that's pretty sticky. Nobody wants to replace, build their own Slack. Um, and I could see a situation where you go, "Hey, we're cutting Salesforce," and they just raise their rates on Slack.

    19. HS

      I don't know. So I, we actually incubated a company which is-

    20. RP

      A Slack competitor?

    21. HS

      Yeah, it's a direct Slack competitor built for the AI age.

    22. RP

      Okay, yeah.

    23. HS

      And it's kind of actually predicated on, uh, a kind of idea of Alex Rampell from Andreessen, who says you wanna be in markets which is greenfield bingo, which essentially are markets where there's a huge amount of net new customers created every single year. In other words, you don't want to exist in markets where there's static Market entrance

    24. RP

      Mm-hmm

    25. HS

      And actually, our market is every new startup that's ever created. If you're creating a company, do you wanna go onto, like, Slack and Salesforce, or do you wanna have an amazing-

    26. RP

      What's the best new thing?

    27. HS

      ... AI first messenger

    28. RP

      That makes sense

    29. HS

      Which I thought was interesting

    30. RP

      Yeah. Definitely wanna be in big markets too, but the... I, I mean, I think, like, how did... We're coming back to our earlier thing about SaaS. I think there's gonna be a, a lot of categories where you say, for example, there's one or two pieces of software that we fully replaced and killed it, and, and more every few weeks. But there's gonna 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

  13. 50:26 – 58:31

    Ryan's Best Angel Bets: Rippling, Bitcoin & Missing Cruise

    1. HS

      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, like, what have been some of the best angel checks?

    2. RP

      Yeah, I've done really well as an angel investor. I, I used to do a ton of it.

    3. HS

      Yeah.

    4. RP

      Um, early days of Flexport. So I, 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, uh, because I realized I, I had inside access. I was kind of like a-

    5. HS

      Was it really obvious who was great, and did your beliefs on who was great turn out to be correct?

    6. RP

      It wasn't obvious who was great. It was obvious who was terrible, though. And I think if you can eliminate the bottom half, like, you're doing pretty well inside of a YC batch.

    7. HS

      What were the bottom half doing that the top half weren't?

    8. RP

      You just talk to the people and be like, "Oh, this guy-

    9. HS

      You knew

    10. RP

      ... the person, nah." And they didn't see me as an investor, so I, you know, I'm their peer, so I could get, like, the real story. Um, so I invested inside my own batch. I invested in, like, 13 of the 50 companies or something like that. And there, there was a few good outcomes there. Algolia, I was an investor in that. But I missed Cruise. Cruise was in my batch.

    11. HS

      Did you get out of Algolia?

    12. RP

      Yeah, I did. I sold my shares in Algolia a while ago.

    13. HS

      Well done. Fantastic.

    14. RP

      So I made money on that one. Um, but, uh-

    15. HS

      You missed Cruise?

    16. RP

      Yeah.

    17. HS

      Why?

    18. RP

      And I'm friends with Kyle. I don't know. It's just like it was too crazy. Like, he was just, like, throwing this camera s- set up on the roof of his Honda Civic or no, his A... I forget what car he had, Acura or something. I was like, "This is not, uh, legit."

    19. HS

      It's not a thing.

    20. RP

      It's not legit. Um...

    21. HS

      You know, the crazier the thing, the more I'm like, "I need to do that."

    22. RP

      Yeah.

    23. HS

      Because if I don't get it, I'm probably missing something.

    24. RP

      Maybe, yeah. So, uh, what are my best angel investments? Um, I was... Well, actually Bitcoin, I... Early Bitcoin. Sold that. Don't, don't kidnap me. I don't have any Bitcoin anymore. But, uh, uh, I made money on Bitcoin. Um, the... I was the first investor in Rippling. Uh, put a big check into that. Did really well.

    25. HS

      Are you revengeful?

    26. RP

      Yeah. Uh, no, I'm personally not, but I think that investing in founders who are, have a, who are pissed at somebody and, like, wanna get back at them, like Rippling. Dario I'd never met before, but yeah. Uh, I don't know if he was wronged.

    27. HS

      Rippling?

    28. RP

      Yeah.

    29. HS

      Parker?

    30. RP

      Parker Xenophons.

  14. 58:31 – 1:00:57

    Peter Thiel's Zero to One Test: How Flexport Beat the Monopoly Rule

    1. RP

      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, um, "Is it a small market?" 'Cause he, his whole thesis was like, "You should have a market that's small enough that you can be a monopolist." And when I went to whiteboard with him and hang out with him, I'm like, "Well, look, it's, I wanna know, like, should I be, should I make myself like I can make this a small market?" I'd be like, "Oh, we're gonna dominate like logistics for s- hardware companies in Silicon Valley or something." But like it's kinda fake. Like the market's actually really big. And he like stopped me and he's like, "Look, it's, don't be too dogmatic. It's okay to have a big market," [laughs] you know. Uh, and then a few weeks later, he emailed asking if he could invest, so.

    2. HS

      So my biggest mistake is when I focused on market at all. I, all of my biggest mistakes investing have been actually not really like in, um, losing money. It's been turning down great companies.

    3. RP

      Mm.

    4. HS

      But because I thought that I was smarter than the market. Oh, this market's shit. Oh, this market's shit.

    5. RP

      Oh, man.

    6. HS

      How many angel investments have you done?

    7. RP

      I, oh, I did so many, so like the vast majority didn't do well.

    8. HS

      Like 200?

    9. RP

      Yeah, something like that.

    10. HS

      Wow.

    11. RP

      And, and like-

    12. HS

      Do you track them?

    13. RP

      I have a Google sheet. Yeah, I track them.

    14. HS

      Do you? I, no, I've just made one.

    15. RP

      Well, I didn't for a long time, but at some point I had to clean it up when I was getting married and, uh, going through that exercise.

    16. HS

      What of doing like a will and... I just need one for a will.

    17. RP

      Yeah, exactly. Well, eventually you wanna clean this up. Uh, much better if you track it from the beginning. Um, the, I would say probably it's, it's super power law world. And actually this is an interesting thing for founders to understand, is w- once you see the world from the perspective of the angel investor, you realize that we really don't care. Even a 3X, like if you take my spreadsheet and this investment made three times the money, like the founder's 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 1,000X or 500X, so they comp- 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, and that way I don't worry if it fails.

    18. HS

      What do you think founders don't know about the VC mindset that they should do? I think that's really valuable 'cause I, I also see, and this actually does pay me, which is like a really noble founder mindset, which is I'm gonna give five to 10 more years of my life to grind out a one

  15. 1:00:57 – 1:02:06

    What Founders Get Wrong About the VC Mindset

    1. HS

      and a half X.

    2. RP

      Mm.

    3. HS

      And I'm just like, "Don't." I, I, and I don't mean that callously or flippantly.

    4. RP

      Yeah

    5. HS

      ... I'm not being flippant with VC LP money, but just your time and my time.

    6. RP

      Yeah, yeah. I didn't even want the investor updates.

    7. HS

      It's, it, it, yeah

    8. RP

      ... it's fine, dude.

    9. HS

      Yeah, like it's okay.

    10. RP

      Yeah.

    11. HS

      Like return 0.6 X is better.

    12. RP

      Yeah. I mean, if it's your life's mission and your calling, then like great, never give up, never quit.

    13. HS

      No, but also the ability to like-

    14. RP

      Um

    15. HS

      ... investors.

    16. RP

      You know, um, the, there's that. There's what I was saying earlier of like how much they're a circular rumor mill. You know, like when I was doing, uh, 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, I, I never had this attitude that like you shouldn't ever talk to the junior people, mostly 'cause I'm not a dick, but also I just assume that those people someday will become like partners-

    17. HS

      Senior, yeah

    18. RP

      ... and they'll remember that I was cool. I don't know. I, I, I, uh, and um, 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

  16. 1:02:06 – 1:04:19

    The VC Rumor Mill: How Associates Trade Gossip on Founders

    1. RP

      here. Like we're not, this isn't gonna work out and I'm gonna raise..." You know. And they, 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. Uh, and within an hour I got the, all the funds that I was still talking to called me like, "Hey, what happened? I, you w- I heard you picked a lead." And like the amount of rumor mill and collusion that happens in VC, founders have no idea. It's like this cra- And you can use it to your adva- It can work against you or can u- use it to your advantage. Like it, you're looking for an outlier who will value you more than everybody else. So like you don't, that collusion does not work to your advantage unless they're all hyping you up and saying, "Dude, this is the best company ever."

    2. HS

      This is so not in my interest at all. But that's why I always say to founders, "Don't, like test the market. Don't like dip your toe in with one or two meetings," because the associate WhatsApp groups are so pernicious.

    3. RP

      Mm.

    4. HS

      Where if you meet me and I don't think you're great, I promise you they put you in the weekly roundup, which they send out 'cause they're exchanging currency.

    5. RP

      Oh, yeah.

    6. HS

      They need to give to get.

    7. RP

      Yeah, exactly.

    8. HS

      And so I'm putting you in my weekly update where I say, "Ryan-"

    9. RP

      Oh, wow

    10. HS

      "... only at a million ARR, not growing that fast. Not a compelling sales rep."

    11. RP

      And these are within a firm or these are cross firm?

    12. HS

      They're cross firm.

    13. RP

      It's crazy. Yeah, exactly.

    14. HS

      Exactly.

    15. RP

      That's what I was getting at before. It's like-

    16. HS

      'Cause again, we're all associates-

    17. RP

      Yeah

    18. HS

      ... and we're all in the I need to bring deals to the firm business.

    19. RP

      Mm.

    20. HS

      And so they all send weekly roundups of who they've met and seen.

    21. RP

      That's crazy that they're sharing that externally.

    22. HS

      Oh, shit. Yeah.

    23. RP

      Do their, do their, their firms probably don't know, right?

    24. HS

      No, no, no, no, no, no.

    25. RP

      Yeah, you'd get fired for that. Yeah.

    26. HS

      But remember, they're more in b- this is almost a good article, actually, but the associates are more in business with that class-

    27. RP

      Yeah

    28. HS

      ... than they are their firm.

    29. RP

      Well, and they're trying to get ahead within the firm and by showing that-

    30. HS

      That's it

  17. 1:04:19 – 1:10:49

    Why Founders Should Never Share Their Metrics

    1. RP

      metrics until-

    2. HS

      No offense, dude, we're kind of past that age. [laughs]

    3. RP

      Yes, I don't need to raise any money ever again. Um, uh, but the, uh, you should never share your metrics because what you wanna do when you pitch a VC is take, you wanna cherry pick whatever metric looks the best and pitch that as the important metric for your firm. But once you've shared a metric, you're now committed to that being the metric, and who knows, maybe you couldn't make that one go up, uh, hockey stick style, but now you c- you're, you're committed.

    4. HS

      I, I remember Colleen Matild, I think it was Colleen. I think it was. Uh, from do you know Colleen? Um, a front, French founder, YC partner now, I believe. A awesome woman. Um, and, uh, she always told me that you wanna raise when you're really confident just 'cause like confidence emanates.

    5. RP

      Oh, yeah.

    6. HS

      When were you least confident raising? [laughs]

    7. RP

      Least? [laughs] Oh, God, when you're losing a lot of money. Uh, Flexport's had... Y- we, we've been on the hero's journey, right? Y- y- you're, uh, if everyth- anything that's straight up and to the right, by the way, is pretty boring. Not, as an investment, great, it's wonderful, but like as a human story, that's-

    8. HS

      It's pretty hard to see any company. I, I've tried and think, to think about this before. Snap was pretty up and to the right continuously. I mean, post-IPO it's been a-

    9. RP

      Right

    10. HS

      ... up and down, but it was pretty continuously linear up and to the right. Not many others have been.

    11. RP

      Yeah. But I don't even mean as an investor. As, as an investment, of course, you want things to just go up and to the right and never come down. But as a story of like what's compelling to the human, like Snap's 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, "Wow, what happened here?" Like that, the human brain loves the story-

    12. HS

      Sure

    13. RP

      ... the hero's journey where you gotta go to hell and come back. Like if it's just always good, like that's not fun. So we-

    14. HS

      Dude, social media posts, the absolute bangers are zero to hero. I started in my bedroom with no dollars and now I'm, you know, sitting here with Ryan Peterson.

    15. RP

      Yeah, but even, even zero to hero is not good enough. You wanna go zero to hero and then take a fall and come back. So we need to cancel you and then the comeback. 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 our s- we don't scandals, it's just 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.

    16. HS

      I remember this.

    17. RP

      It was one parcel.

    18. HS

      It was quite a scandal.

    19. RP

      And it was a newspaper, I mean, Bloomberg's not a p- print, but it was an, it was front Lead of the story that Flexport, we used DoorDash to do the delivery. One parcel. By the way, they did-- 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. Like, 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 lowlife, uh, looking for dirt

    20. HS

      One in 40 million

    21. RP

      So I mean, we probably lost more than one, but the story was about one.

    22. HS

      You dick.

    23. RP

      And, and actually it's a 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, um, it, 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, "Yeah, 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..." It, it's something they have to overcome, um, because their quality is actually fine.

    24. HS

      Well, it's, uh, I think Tony Robbins said this once, but it's like how fast appreciation turns into expectation is extraordinary. And it's like, you know, before you're like, "Hey, we didn't expect to have Wi-Fi on the flight, but now we've got Starlink"

    25. RP

      I need Starlink.

    26. HS

      And you're like, "Wow, that's amazing."

    27. RP

      Yeah.

    28. HS

      And then you get expectant of Starlink, and then the down is so bad.

    29. RP

      Yeah.

    30. HS

      What did be a massive appreciation, now you're like, "I fucking expect this."

  18. 1:10:49 – 1:17:23

    Pitching Masayoshi Son: $1B in an Hour & Calling Foxconn Live

    1. RP

      uh... I love Masa.

    2. HS

      But like do they-- How-- Did you pitch Masa?

    3. RP

      Yeah, yeah, of course.

    4. HS

      How was it?

    5. RP

      Uh, I love him. Uh, he's just like a big, larger than life-

    6. HS

      Was it in person?

    7. RP

      Yeah, yeah. Uh, I think, uh, definitely in person. I'm pr- trying to remember if I also met him first on video. No, it was in person at-

    8. HS

      But can you just take me to this? I love Masa. I love gambling. Masa's like-

    9. RP

      I just love the guy

    10. HS

      ... how was this? Where was this?

    11. RP

      I mean, I, I don't, I can't say I like love him that much interpersonally. We're not friends or anything.

    12. HS

      No.

    13. RP

      But like I'm just like a big fan of Masa the, the figure-

    14. HS

      Sure. So tell me how, like where did you meet? How did it go?

    15. RP

      I met at-- First time I met him would've been at his house in Woodside, California, which is like, it's very nice, let's say. [laughs] It's-- You can look up the Z estimate. You're like, "Oh, this is gonna be fun." The Zillow estimate.

    16. HS

      How long was the meeting?

    17. RP

      Probably like, actually pretty short. Maybe an hour or so.

    18. HS

      Okay.

    19. RP

      Um, considering the size of the check, I thought it was surprisingly short meeting. He has this, uh, painting of Napoleon behind him. [laughs] Um, and I wanted-- I didn't end up finding one. I was trying to f-buy a painting of the, um, the Duke of We-Wellington to send it to him, right? Uh, who of course defeated Napoleon, but-

    20. HS

      Sure

    21. RP

      ... as a troll, but I never found a good one that it was worthy of the, of the prank.

    22. HS

      It's a, it's a bold move as well.

    23. RP

      Uh, yeah. [laughs]

    24. HS

      It's risky. I would just leave it.

    25. RP

      Long after he invested, I was gonna send him that as a gift. Um, he, he's very bold. You know, I, I don't, I... He wanted me-- He pushed us to go, "Hey, you know, drop your... Be cheaper than everybody." 'Cause we raised a billion dollars from them, so it's like-

    26. HS

      You raised a billion from them?

    27. RP

      Yeah. Well, they led the round of a billion, yeah. Uh, and he was like, "You-- 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've burned so much money. But he was very aggressive. He just wanted to push you to go bigger-

    28. HS

      I like the mental elasticity though

    29. RP

      I mean, he-

    30. HS

      It's different to most investors.

  19. 1:17:23 – 1:20:48

    Quick-Fire Round

    1. HS

      months?

    2. RP

      For the last decade, I wanted to be... I didn't wanna compete on price, and I wanted to be the premium value, 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 that... Ex- if you're cheaper, you just take all the market. Uh, 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 our- 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.

    3. HS

      Uh, who do you not have on your board that you'd most like to have on your board? Magic wand.

    4. RP

      I, I don't, I, I don't think our Flexport's board n- needs anybody. Uh, the board is, like, mostly there to represent the interests of our inve- the investors and make sure we're doing a good job, not, like-

    5. HS

      Okay

    6. RP

      ... driving the company.

    7. HS

      But whose wise counsel would you like to have?

    8. RP

      You wanna join the board? Is that what you're angling?

    9. HS

      I, I mean, listen, I, I think I'd add a lot to the board personally-

    10. RP

      [laughs]

    11. HS

      ... but I, it needs to be your decision ultimately.

    12. RP

      I'm just glad that my board doesn't screw with us. Like, I am... 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 h- 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.

    13. HS

      Penultimate one, what sports team do you not sponsor that you would most like to sponsor?

    14. RP

      Oh, uh, I really would love to sponsor, uh, this football club in, uh, Hamburg called St. Pauli.

    15. HS

      Why?

    16. RP

      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 he, I don't know if that team was around back then, but, uh, his, uh, the first team is owned, uh, by, um, Klaus-Michael Kühne, who's the owner of our direct competitor, Kühne + Nagel. And I just love the idea that we would take the second team [chuckles] and beat him, and he would be like, "Ah, those kids, these damn kids, here they come again." Uh, so just more of a troll than anything else. And their logo is a pirate. They're like, kind of like a leftist, um, communist-oriented club. I think they would kinda hate us if we tried to buy it. [laughing]

    17. HS

      [laughing] Yeah, maybe, maybe. I didn't know that. Um, 'cause they wouldn't be that expensive. But if-- Yeah, and totally. Uh, also sports is a tough business to make money in.

    18. RP

      Yeah, yeah. I don't wanna own any teams.

    19. HS

      Uh, final one. What has to happen in 2026 for you to consider it a successful year?

    20. RP

      We gotta hit our numbers. We gotta grow like crazy, and then this automation via AI, like we, we, we've got about, well, probably like 100 core workflows that are costly that we have AI-- 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, 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.

    21. HS

      Dude, it's been so great to have you in person. Thank you so much today, and also on a Sunday, uh, of all times. So I really appreciate it, dude, and it's really special to meet you in person properly.

    22. RP

      Yeah. It's great to be here.

Episode duration: 1:20:58

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