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Eric Glyman

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2025-10-13
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2025-10-13
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  1. Wednesday. I love Steve Jervison. That's my guy. What an investor board member of Tesla, SpaceX investor. I mean, you want to talk about a mensch and a visionary investor? Steve Jervison, the J in DFJ. And now he's got his own venture firm. We'll see you on Wednesday, everybody. Bye-bye.

    2025-10-13 · This Week in Startups · What Ramp's data tells us about AI, unemployment and more with CEO Eric Glyman | E2192 · IDENTIFIED FROM THE TRANSCRIPT · source

  2. A little magnanimous when you're at the top, right? Because you sometimes forget how much power you have. I don't anymore. I know that if I mention somebody on the podcast, it's going to carry a little bit of weight. I'm not overendexing on it, but it could negatively impact them. So I've been more thoughtful in how I'll say things. I used to be a little more Howard Stern, a little more shoot from the hip.

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  3. Power, which y combinator is the height of power, and you have this impact on people Best advice. Do what I did. Do a little personal self discovery, you know, whatever it takes, just reflect. You can never go wrong by being helpful and being a mench. And you can go wrong by being critical of people, especially publicly like this, especially for a nascent founder, because some people will frame it as bullying. Not framing as bullying, but obviously that's the reaction online here. So this is the thing about the power imbalance that YC maybe needs to, and this is something Gary has inherently in his DNA, I believe. He's a very competitive person. He's a full contact person, as you can see with his opinions on math and San Francisco. All good character crates. But he should probably... Into the YC Culture being magnanimous.

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  4. I notice you taking those notes in the docket. Well done. If you want to tune in live, go to this week in startups.com slash YouTube and it will automatically send you to YouTube and subscribe you to the show. All you have to do after you subscribe is it gives you a little pop-up on YouTube. Hey, would you confirm you like to subscribe? You confirm you want to subscribe, but you hit the alert in the bell there. And then if you could do JCAL and Alex a favor, write us a review on iTunes. I hate to beg for reviews on Apple Podcasts, but it is a big part of the show getting surfaced to new people. If you write a great review, we're going to shout you at the end of the show, which we're about to do at the end of the show here. We'll read one of the great reviews. And if you email me your review at Jason at allin.com or Jason at Calicanus.com, we'll go to the same place. I'll write you back and say thank you. And you get to say hi to me because I'm a real person. It's true. I'm a mensch every day in my life. I am a real human on planet Earth. And if you get to a position of...

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  5. They'd say, where's Goldie? Because we want to have a mench at this lunch. Literally, he's a mench's mench. That's what I aspire to be in my life. I aspire to be Goldie and be a mench. Another amazing episode of this week in startups, I'm going to get emotional, so I'm going to leave it there. Unless you have anything else we need to add or any housekeeping we need to do here

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  6. He ran survey monkey. He ran launch.com in a way. I did launch.co as a tribute to him because I always loved the brand launch.com, which was his music startup. He gave me time when I was coming up in my career that he didn't need to give me. And if you ask anybody who met Goldie, he gave everybody an hour or two. He didn't need to. He was rich already. He was living the life. He could get any meeting. He could hang out with any powerful person he wanted. Died too young, but when he was alive, what did he do? He was, if you met 10 menses and there was a mench lunch.

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  7. The top rungs of the ladder, where I've been lucky enough after a 30-year brutally hard career, fought my way in here. I get it. I had to go punk rock. I launched a zine. It's this punk rock as it fucking gets. Like I couldn't get published, so I started my own magazine and photocopied it. You know, people didn't respect me. I started my own tech conference because I couldn't get into other ones. Period, full stop, right? I started my own podcast. It's okay to be punk rock. But then when you do win, you got to flip Alex. And this takes personal development work. And it starts from the top and the leadership. The leadership has to say, hey, we've won. We're going to be relentlessly magnanimous. If I could put a post-it, you know, here on my teleprompter, it would be a mensch, like my guy, Dave Goldberg, rest in peace. He was the mensiest guy ever. I modeled my career after Dave Goldberg, Goldie, rest in peace.

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  8. I think they're just a little too cutthroat, I'll be honest. It's a bad look because they don't need to be. When you're winning, you should be magnanimous. I've had to learn this in my life. All of us have to learn this. Chamatz talked about learning this. When you win, especially in when you get to the top of the

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  9. And if you don't get into YC, I don't think you should just apply to YC. I think you should apply to our program found in university if you're pre-revenue, you know, like year zero or apply to the launch accelerator. We have a common app, launch.co slash apply. I also think you should apply to Andreason Harowitz's speed run. Does a pair VC, a MAR does a great program over there with Pegemon? These are great investors, great founder-friendly folks, rule off in the team, Stephanie and everybody, they do the ARC program. And we'll put those links in the show notes today. I am not a zero-sum person. You should, I think the Y combinator folks have a little bit of like circle the wagons. They're not.

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  10. So Daniel did deleted his tweets. Anyway, I'd like to have Daniel on. Maybe there's a good investment for me. And if you get rejected from Y Combinator, don't wait six months, email your boy. That's very simple. Jason at calicanis.com for life, or you can email me if you love the all-in program, Jason at allin.com, or if you want to get a meeting with the 11 people on our investment team, forward your YC application that got rejected to yc at launch.co. yc at launch.co and you will get a meeting with my team within 24 or 48 hours, including a little bit of weekend time because my team works a couple hours on the weekend to meet with founders. We will meet with you quickly. We'll do a 20 minute first call with you. You pitch us your product or service 10, 15 minutes. We ask you one or two questions. You ask us one or two questions. Then at the end of 20 minutes, we end the call and then we will talk to you and have a follow-up and see if it makes sense for us to go to a second call. We do this because it's founder friendly. It's good to save you time.

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  11. I think I'm going to give Michael the win here that I think actually he gave them a firm crisp set of decisions. You might say like pick one or two is my best suggestion. Hey, listen, if you guys want to have chaos, that's fine. That's not what YC is about. We need harmony because we've got two, like I mentioned earlier, like there's 200 other, there's 199 or 299 other people in your cohort. Like, please, but stay in your lane and just be productive for 12 weeks at the end. So anyway, long story short, YC's amazing. Gary's great. Michael's great. And this kid's great who's being a little punk rock. You can't optimize for punk rock and then be upset if somebody's punk rock with you. The end full stop, everybody. And for the YC people, did they delete their tweets when they were dunking on the kid? I saw there's a bunch of deleted tweets in that thread. I don't know whose tweets got deleted or if we know.

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  12. If you do due diligence, and it turns out like your customers don't match or whatever, or it doesn't feel like particularly defensible technology, you have the right to back out here. I think, I don't know, I might be on Michael's side here that he gave them some great options

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  13. Everybody just tries to help the ecosystem. I'm kind of making a joke here because people do get competitive. And I can understand if it's Michael Seibold or if it's Mary Susan, whoever, you want to have a clean separation if there's going to be driver. I don't think that emails too aggressive, except for maybe the last line, like pick one or two. But sometimes you've got to be firm with a group of people who are causing chaos and be like, listen, one, two, three. I have had similar situations happen where something comes out during due diligence. We haven't signed the deal yet, but maybe we're between handshaking due diligence. And you can say a thousand times to a founder. Pending due diligence, and they will not hear that. That is like a frequency. That they're not capable of hearing.

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  14. Which is worth, I don't know, close to $100 billion. My two unicorns are worth more than that, but I didn't know it's not.

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  15. All right, listen, it's business. Things can get a little chippy sometimes. It can be very annoying if a founding group like this, you fund them and then they start creating chaos. Because what you don't want to do is have a distraction in the incubator for the other companies. That's not fair to the other companies. Just like if you got accepted to Columbia or MYU and you start causing drama everywhere and we've got you on a scholarship and you're going to be on the basketball team or the hockey team and you're just running amok. And it's like, well, maybe this isn't the right opportunity for you. We take our scholarship back. In this case, it's 125 bucks, 125K. In this case, if I was YC with billions of dollars under management and dozens of unicorns, including their most successful ever, I think it's Airbnb.

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  16. Pick up artist stuff. Yeah, that's what I couldn't find. The nag is like, oh, wow, you know, one of your earlobes, Alex, is longer than the other. That's kind of weird. And Alex is like, will you date me? I'm already dating you, the co-host. Okay, let's read this.

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  17. So there also was another comment. There's just a count called spec that is obsessed with Gary Tan. I love Gary Tan. I've known Gary Tan. I think he's a great human being and I think he's a great founder and great investor. I know he had a bad breakup with Alexis O'Hanian, who I also have a lot of respect for, so I don't know. Sometimes founders can break up. But I think Gary's great But this account speck, which is openCV with underscores on either side on Twitter. Keep CC seeing me in this because I guess they want me in on the drum, or they CC a lot of people But they had an interesting tweet.

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  18. If I tell you anything, it's in your best interest. I'm only doing it to help you and be a good participant in the ecosystem. Like literally, that's 100% of my motivation. So please don't give two seats to somebody. Please don't give two different investors or three different investors three different terms and side deals and just keep it standard. And if you're going to sell the company, let's have a process. Don't just sell it to your friend and then not do the process. Don't give yourself shares without telling the board members you want to give yourself a new equity grant. Like there's a process here. And let's not get you in trouble or cause reputation damage. But here, I think Daniel Young is punk rock, and I'd like to have him on the show on Wednesday.

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  19. Well, no, you could then have to go back and reverse it, or they sign a deal without telling us, or then we're like, well, no, but did you talk to your lawyer first? Or like, no, no, I got this great deal. I signed it. And you're like, oh, okay, just you're supposed to do that. So I always tell founders now, like, before you do any deal or you give somebody three board seats like a founder did recently, gave them two or three board seats. I'm like, please call me first. Please call me first because I've already made my money. I'm already micro famous as everybody knows and I'm slim now. Like everything I want in life. I got a great family. I'm Schweld again. I made my money and I'm micro celebrity. And a micro celebrity. Let me tell you, it's a pretty fantastic place to be. I got a lot of great invites. I can go to F1. I can go to all this stuff and hang out in the pits. I don't have to buy a ticket. It's fantastic.

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  20. That's the right response. I've had founders do like multiple times. This has happened with like 10 founders. I've had 10 founders do a round of funding and not tell me. When we have rights in that round, when information your program

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  21. I think you'll have a better experience. And I think that's what Y Combinator is feeling is like they have competition now. And also there seems to be something with young founders. And I don't know why this is, but there seems to be some pent up, and maybe it's just the nature of being number one in the space and having such a great reputation. So it's actually in some ways a complement that dropping out of YC is the equivalent of dropping out of Harvard. If I was Tyler who says, imagine breaking a handshake agreement and bragging about on social media for likes, That's a terrible tweet. But they should have said was we appreciate the founder. We think they're amazing. We wish them great luck. We wish they would have come to Y Combinator. We hope that when they raise their next round, maybe we could participate. We wish them all the best. If the program's not for them, we want them to do what's best for them.

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  22. Arc by Sequoia Pear has their summer program. We have launch accelerator and founding university for a long time. We're not a new entrant. TechSars is coming back. Antler, all of these programs are better for founders in my mind than going to YC. Not that YC is bad. YC's as good, but I think these other programs are better because they give better terms and you're not one of 500 founders or 250 founders. They're more bespoke. So if you go to speedrun, if you go to Sequoi Arc, if you go to Pear, if you come to our program and I'm talking my own book here, obviously, it's less of a factory-like Y combinator. And you're not going to get lost and give a one minute presentation on demo day, right? Other programs like ours, two or three minutes, you know, you get a little more time and ours, you're one of 12 companies, not one of 200 or in ARC. I think they take a dozen. They're more bespoke. If you can get into one of the bespoke programs.

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  23. You know, is it Rude? Is it unethical, immoral? All right, whatever. Yes. Yes and no. But the deal's not signed until the deal's signed. You have the right to back out of it. You can say like, okay, I want to do that. But if like on the way to your car, somebody's like, I'll just put a million dollars into your company directly at a $10 million valuation. You don't have to give 10% to YC for 200K. Well, okay should be happy for them. The reason why C is overreacting here is, well, one, they're super dramatic. Everything they do has to have this drama. But this is anti-founder, you know, and they're like really concerned that this is going to become a trend. I think they've been very threatened by some of the new speed run from A16Z.

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  24. You know, like that's what they're optimizing for. They're optimizing for punk rock. And then they want Daniel, the Daniel Young on Twitter, they want him to be well behaved and stay in his lane. I mean, F off. This kid's punk rock. He can say, hey, you know, I did the handshake, but I didn't sign the safe. I'm out. In fact, he can sign the safe and say, you know what, I don't like this give. I want you to let me out of the safe. Now, they don't have to let him out of the safe, but he can be punk rock. That's like the whole reason founders win is because they're willing to be a little punk rock. And if I'm YC, the proper response from the YC people with this, I see Pete Kuman, who I guess it looks like from his Y Comedy logo, actually this triggered them. Wow.

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  25. Boo Hoo, Y combinator complaining about this and using the YC brand to say it's a YC dropout. Harvard doesn't complain when Zuckerberg does it. And in fact, Y Combinator is known for asking that question. Tell us when you broke some rules. I don't have the exact question, but they ask people and they sort for people like Sam Altman, who are rule breakers, who do crazy things like take a nonprofit for open source, you know LLMs and make it a for-profit. Yeah.

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  26. Okay, great. Yeah, yeah. I was just showing people the docket, by the way. If you're looking at the YouTube video, you can see our docket here. That's why I encourage everybody to go to the docket this week in startups.com slash docket. You see the notes that we're actually reading from and our research team did and producer Claude did. But yes, you share and I'll talk. So here's what I want to say.

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  27. We're in our docket. If you want to follow the docket, you can watch us build the docket starting the night before this week in startups.com slash docket. And then as we're doing the show, you can see me in real time looking at the docket and I do strike through when we've covered something. And I really want to cover this story about the broken handshake deal with YC and God, it seems like every day is another YC drama. Let's go to the drama. Tell me about the drama. This week in YC Drama.

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  28. No, no, no. I mean, part of the reason you're here is that you have such great industry knowledge having been at TechCrunch as a high schooler.

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  29. You guys, pal. What a great guest, huh, Alex. I love a guest who just was like, yes, I'll answer that question. Not the question my PR department asked me to filibuster in and shoehorn into the discussion.

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  30. Yeah, you know that Elon invited me there on a Saturday parking lot full, ordered in steaks, hung out with the top people. It was very impressive to see their commitment. And they were working on that humanities last test. Is that what it's called? Humanities Last Test? And they were like walking me through the problems that are like the hardest things in the world to solve. And they didn't want it to like have known the answer just from like, you know, I got, I stole the teachers, you know, quiz book and I got the answers. They wanted to know how to actually do it. So they introduced a demonic AI agent into the group of agents solving the problem. And they said the goal of this demon is to try to give the wrong answer. And then these five agents have to explain to it why it's wrong. And it was really, really interesting. What are you showing here, Alex?

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  31. Was able to take so you got to be on top of this. Your tech team's got to be on top of this because it's a major expense and it's a major opportunity. After OpenAI, which obviously you had a major partnership with, who's most impressive to your tech team?

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  32. Together, yeah. So take me through how you think about load balancing and or comparison shopping and negotiating for tokens versus I'm going to just stand up one of these open source models. Have you tried standing up an open source model and just saying I'll just do it myself?

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  33. Quite a bit. So, if not tens of millions, you're certainly spending millions on AI with open AI. Just as a founder, Open AI came out first, but are you looking at the other models and low balancing beside them and actually thinking like people did in year five, six, and seven of their cloud spend years one through five, you're like, this is amazing. I don't have to stand up my servers. They get to year six or seven. You're like, wait a second. I wonder if, you know, Google Cloud is going to be at Azure or if Azure is going to be at WS or Oracle's cloud. I feel like we're now in that moment where people are going to start price comparison. And then there's always deep seek open source. And there's another open source competitor in America now that's doing pretty well. So how much do you spend? Which one was it?

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  34. What you learned in college is so superficial and light compared to the depth of AI if you just spent one year using AI tools exclusively, you would be so much further ahead than trying to remember that, you know, top 10% of the knowledge. Interestingly, to spend a, if you've spent over a trillion, I'm just looking at Claude AI explaining to me what that costs looks like you're spending tens of millions of dollars on AI spend to do this ballpark correct with OpenAI?

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  35. Before you go into this thing, what about the rant? What are you using tokens for at ramp? Are you using to identify spend and categorize it?

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  36. Oh, this is such a great insight. Because that information is on the open web because these are careers and people are searching out career information. So content producers, universities, they put all this stuff online. So therefore, the LLMs get, what a great insight. Wow.

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  37. Adjusted three months rolling average 22 to 27 years old by education type non-college, which I'll call generation tool belt. That's what we call it here on the program versus college grads, in some cases getting like weird degrees, the college grads spike up. Nobody needs them. Now for women, the gap is not as bad, I think there's more women in college, but for men, it does seem like maybe men are not as necessary in the business workforce with their college degrees or maybe they get in the wrong ones. And here's from the Bureau of Labor Statistics 2019, recent college graduates were at 3.25 second sell down in the second column. 2025 average, same time period, January to January to July versus January to December, but 4.9%. It's up 1.34.

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  38. And Salesforce and HubSpot, they'll come rescue you to get your payment for the next year. They will find you. There's no way for them not to find you because they want that renewal so bad. And so I would just turn these cards off and everything would be ding, ding, ding, ding. We'd make phone calls. They call everybody. They get on LinkedIn. They would DM everybody, email everybody to find out what's going on. How do we get this thing renewed? And man, that really works well. That's my favorite use case for what you do, Eric, is to just ramp the cards down to $1 a month and just watch people lose their mind because of these dark patterns. I wanted to share two things that I just think would be interesting for our discussion while we're here, you know, this crack team I have here doing live research to just go back to our discussion. Young male college grads are now jobless at the same rate as non-grads. So just take a minute, Eric, to think about this. If you look at the college grads on the left, the men there.

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  39. I had my own, I rolled my own ramp experience in this way when I would have like two cards created under my card, one for like media subscriptions, New York Times, whatever, and then one for SaaS subscriptions. And they would just say, cancel them. I would literally cancel them in September because I know all these things are coming. Trust me, if you're lost on an island, like literally Wilson, what was the Tom Hanks movie? Castaway with the hand prints of that Wilson You're literally with that soccer ball

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  40. At 92, 93, everybody was trying to figure out not how to get the cheapest flight in a hotel, but trying to figure out how to get the most points so they could take their summer vacation. The company just kind of turned a blind eye to it because it's like, yeah, whatever, we're making billions of dollars. But I think that's probably correct. And then you have new entrants like Robin Hood. I have that. I was an early investor in Robin Hood. They sent me one of the first gold cards and they pay you back money like 3%. So I do think there's this trend towards that. I was going to tell you a ramp lounge that when you go to the ramp lounge, you buzz in with your ramp card. And it's like, yeah, here's a bottle of water. Get the fuck out. It's like that's not why we're here. We're not here to get too long.

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  41. They have screwed them up. This is like become a literal thing that the velvet ropes, they just, they're not building enough velvet ropes behind the velvet ropes, in my experience. So that makes sense. I always felt, Alex, that like this was a bit of a grift because I remember when I had my last job working for somebody, which was Sony.

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  42. Paper OS has helped over 10,000 funds, founders, and investors, including me, automate their workflows. Their tools will help take you through every stage of the process, from handling the operational details I don't want to worry about because I'm busy meeting founders and looking for great companies. For example, Paper OS has made the onboarding process so seamless for limited partners, their investor intake forms, automated subscriptions. It just takes all the busy work out of managing our syndicate and it automates capital calls, investor accreditation, tax filings. This is tedious and important. These are the chores of running a fund or a syndicate, and they have saved me and my team hundreds. Actually now it's probably thousands of hours, which means we can focus on founders. Our friends at Paper OS want to give you a complimentary $10,000 credit. To claim it, just go to paper OS.

    2025-10-13 · This Week in Startups · What Ramp's data tells us about AI, unemployment and more with CEO Eric Glyman | E2192 · IDENTIFIED FROM THE TRANSCRIPT · source

  43. But when we have big spending, I'm like, get me those United Points, get me my platinum, get me my centurion lounge, because we'll use those. So I guess first question, where do you stand in terms of like benefits and competing against the American wonderful, the platinum card is absurd. Not that I'm optimizing for these things, but man, the United flight points is a really incredible program. So how do you think about Amix points this incredible United? And then we were doing Bonvoy for a while and getting, I mean, I didn't pay for a hotel for a couple years there. So tell me how you think about your value prop versus theirs. Obviously, the world's greatest moderator and the world's greatest angel investor needs the world.

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  44. Let me hit you with an idea. Let me hit you with a couple ideas because this is what seasoned board members like myself do. We send you on side quests just based on our own personal experience. That has nothing to do with reality. No, in some cases, it's based on some reality. But I assume that, you know, many people like our company, the executives have an American Express platinum or Centurion. They got a united business and then they got a ramp card. So when I am out and about in the world doing stuff, I'm like, my rank and file employees, go ahead and use the ramp because you're not spending a lot.

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  45. Congrats. What do your investors think about that? Like, I guess pre IPO, that's a good thing because it sets you up, but aren't they also some board member saying, hey, listen, I got in the seed round. I got in the Series A, why don't we acquire more customers here, Eric? Like, what are you doing with this free cash flow? We don't need free cash flow. We're not here for a dividend. How do you manage that?

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  46. If I try to find something to do with their time, because they'll be frustrated, which is what we did when I was a kid, we graduated school in the early 90s. There were no jobs, this huge recession. I think we were probably at like amongst young people mid-teens. I think in that time period it was mid-teens. So, you know, most of your friends had jobs, but probably one in five didn't. One in six didn't. What happened then was people started zines or they started bans or they became freelance photographers and they joined what was called in Wired magazine Freelance Nation. It was really interesting, this concept that you didn't have to have a full-time job and stay somewhere. Let's go to the next piece, which is you are a SaaS-based business and it's got a per employee component to it because each employee gets a ramp card. So some amount of your revenue is based on headcount. So how does this impact you if you're the land and expand concept?

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  47. Yeah, and this is the 50 year low for our lifetime. And if you look at recent college graduates, however, they're having a heck of a time getting jobs, which I attribute to entry-level jobs are being taken by AI because they're easy to automate. Now, Eric, you make such a great point. Whenever a complex system has some unique variable introduced to it, things can get weird and you have reactions. And then you have second order effects. So if you look up the broad concept of cognitive biases and systems thinking, you can jump into a rabbit hole where a bunch of Malcolm Gladwell type people spend and Bill Gurley spend a lot of time thinking about thinking. But the truth is, if there's no jobs for graduates and they're smart, then what three or four of them will do is apply to Y Combinator or Launch Accelerator, Foundation.

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  48. You probably know when team sizes change because they would issue more ramp cards. So, what is the data saying there? Are companies hiring or not? And then what does that say about the impact of AI? Because you're seeing a lot more AI spend. So we got really two interesting points here. Let's just go with the first. What are you seeing in terms of the size of companies that are already large? Are they staying the same, getting bigger?

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  49. And it'll build stronger relationships with your vendors. So find out why over 43,000 businesses, including a number of my own port codes, Have future proof their operations with NetSweep by Oracle. Plus, our friends at NetSuite want to give you a free gift. Download the CFO's guide to AI and machine learning for free. At netsuite.com slash twist. That's netsuite.com slash twist But you also know how the economy is going, I think, Eric. So there's been a lot of discussion, and we came up with a term here for it. What's our term for static team size? So we was talking, Alex and I about this trend for the past four years, Uber, Airbnb, Google, Meta, Microsoft, all having the same number of employees this year as they likely did four years ago or modestly up or modestly down. So static team size. The team size does not change.

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    2025-10-13 · This Week in Startups · What Ramp's data tells us about AI, unemployment and more with CEO Eric Glyman | E2192 · IDENTIFIED FROM THE TRANSCRIPT · source