How the Smartest Founders Are Quietly Winning with AI

0:00 Now zero to one is very likely an AI. You build an incredible tool that no one else can do. You can do a million in a week or two. I feel like I can rule the world, I know I could be what I want to I put my law in it like my day song. On the road, less travel, never looking back. Okay, so for this episode, what I'm thinking this is about is This is sort of um

0:22 And guys, this is gonna be generous to us, but What is the smart money doing with AI? And you know, in bedding and sports betting in Vegas, you always kinda want to watch what are the sharps doing? They tend to be just, you know, maybe 10 or 15% earlier to tr to to understanding things or to recognizing things. And so similarly Uh, Jason, I wanted you on because you've been doing really interesting stuff with AI, both from investing, you're talking to startups that are using him, you're reading all the reports, but also you yourself built this AI tool. And so I wanna kind of Get your reaction to a few of the of the different things. Can you first

0:54 Explain this AI experiment you did where you basically made a body double of yourself out of AI and like what was the experiment and what'd you learn? Well, yeah, so so Saster has a lot of content, as you guys know. We have twelve years of content. Some of it's out of date, right? For for sure. Sasser being um you're a previous founder who's exited multiple software companies. Now you're like the godfather of like Sass because you have this blog and media company and events business called Saster and you have a huge fun. But probably most interestingly

1:22 For for like seeing the future a little bit. Is I have about 10,000 pieces of content I've written over the years, a lot of it, which is not out of date. And I update it personally. So about 10,000 pieces of content. And then we have several thousand

1:37 interviews like you guys do, but with so many great folks. Early ones with Darmesh, middle ones from Darmesh. Darmesh when when HubSpot had just IPO, Darmesh the other day, Yamani last week, Brian Halligan over the years, and we have all of it. And our AI took everything I've written. Every tweet I've ever done, every LinkedIn post, every Saster video from every speaker for twelve years. Aaron Levy, the week he went IPO for the first astro annual to last week when we were talking about AI, all of it ingested in this AI. And so What I instantly saw was as soon as I would talk to this AI, it was much better than me.

2:11 It was much better than me. Because I forget. How did you get that information in there? You just hook up RSS, right? Um, the feed for blog. It can scrape the web, which is pretty easy. Soon we'll be able to do other things like MCB, but it's just scraping APIs and RSS. It's really just scraping. You just give a URL. But did you use like Delphi or you you built your own tool or what'd you do? I tried a couple things and then I used Delphi and then at first we had so much content it was a little difficult to ingest it. So there is there is a little bit of work. And then I spend about ten minutes a day training it, which we could talk about. So there is a little bit of maintenance involved.

2:47 But It's better than me. And the thing I didn't get until I saw something that was hyper trained, like this is a lot of content, twenty million words, right? Ver few mistakes, very few hallucinations. And the ability to connect things that I can't. I just don't remember. I don't remember what Sam and I said on the hustle on stage years ago.

3:07 versus when we did an M Fm the uh a while versus today, but the AI knows it all. By the way, twenty million words is like two hundred books worth of content. Is you basically gave it tw twenty two hundred books of your own brain. uh and the brands of other guests that have come on your show. Yes. And your goal was to build Was it to build basically an advisor, an AI version of you that could be an advisor to a founder who wants to come and talk to you, ask questions, but you don't have enough time of the day to book calls? Was that the big idea? Well, now I just wanted to learn like you guys did. I just wanted to learn. I didn't think it would be as good as it was because I used other products.

3:44 And I've used other things and it wasn't as good as my a my digital AI was. It was but the use case would would be what? Is it what I said or is it something else? The other interesting thing is the use cases with AI are much broader than you'd expect. Okay. So I didn't expect people to upload their board decks before board meetings and ask for feedback before board meeting. That's in this use case. I didn't expect hundreds and hundreds of founders to use it as their therapist for their company where the growth has slowed.

4:11 I didn't expect that. I didn't expect so many folks to use it to review their um sales scripts, their SDI scripts when there's when there's specific tools to do it, right? I didn't expect It's so good at reviewing V C pitch deck. It's so good at it, better than anything I've seen. Can you get tactical for one second? So you got a Delphi dot AI. Uh-huh. And you just uh uploaded the Sasters RSS feed and it did all the work. You YouTube RSS Twitter. Um

4:42 Blah. But could I go to a health guru or a business guru who I ask uh subscribe to who I love? Yes. Can I say youtube.com slash Alex Ramosi upload That and it automatically does it. Is this Well it's an interesting question. It is prohibited, right? It is prohibited by their website, their terms of use. They prohibit it. But honestly, this is an AI risk. We you could you could do it. Absolutely you could do it. You could redo what I did. It might take you a little while longer, but you could just clone exactly myself yourself. And then you would you could do it just as well as I did. Sam, I've never felt so used and abused when uh J uh Jess Ma came on the podcast and she was like, Yeah, actually uh I have my team training an AI of you so that if I'm brainstorming ideas, I don't have to ever call you. I'll just ask the AI what you know, basically you'll just be in the meeting with us. Yeah. It's just like we yeah, we just took all the podcasts and we're training it on how you think, the questions you would ask, what you would say, reactions you would give. And now you're just there in the meeting. So she basically hired me without ever paying me, right? Because I have this corpus of content out there. I've actually put my brain out there in the public. But how do I do that? Like how it can't can I just upload a YouTube channel and say this YouTube creator has great advice.

5:51 And I could upload eight hundred videos and it will transcribe all of them. I could go to Delphi. It may take a c a day or two to fully ingest all that content, but it will do it just from the URL of your YouTube. Just on Delphi.ai. So I could l I could make a mini shot. I actually I think it is a great product. There are other people That can do it too. That is not there are some I'll tell you what I think is interesting about Delphi, but We're looking at all this cursor and windsurf stuff and lovable and like you don't realize like

6:16 They're just so far ahead of Like B to B and regular people only because they're better people working on them. If we had the quality of people working at Windsurf working on on CRM, okay, or working on marketing tools or podcasting tools, your jaw would drop today. But This is why your jaw is gonna drop over the next twenty four months because

6:35 Just mediocre engineers cannot like the op the the engineers at open AI are so good. They're just so good. And so, but the average engineer working at a struggling CRM, right? It's just not just not that that good, but they'll catch up. But yeah, you can build all of this. And here's the interesting learning. So we could build a digital SAM and and we could do this for next week or whatever. You can do it. The i my learning from I it's okay that it's not you. This is why, for example, you can train your voice. It uses uh level eleven. Is that the product or level I get a little confused level eleven, right? Yeah.

7:07 Eleven labs, yeah. Eleven labs. And eleven labs is epic, right? But you can choose do you want it to be exactly like you, which is what Brian Halligan did. And then I realized that was creepy. I don't want digital Jason to be Me. I want Digital Jason to be a prime version of me. That ninety percent of the time is much better than me, but is distinct.

7:26 I don't want people confused like Brian I get conf like Brian Halligan and so Um, it's okay that it's not Sam. Like it could be a version of Sam that is better than Sam. So okay, let's walk let's walk through these top ten learnings. So you build this AI. Uh it has thirty five thousand conversations with people. You did it as we're like almost fifty now. We have fifty thousand conversations and learning number one, you said users will tell AI things that they won't tell humans.

7:52 Yeah. Um, well, first of all, before we even get there, one obvious like there's no way I could do fifty thousand conversations, is there? Right. I'm not even a people person. I could do like one or two a day and I get tired. Fifty thousand just think about the delta between two a day and fifty thousand. But yeah, this is the thing, like There are some things that are somewhat unique about me that are early. The amount of content, Sean, like your math, right? The amount of books we're talking about here, right? The amount of content I've written just about B to B, just about bus building business software makes it interesting. But the other thing is there's enough people, I'm not like a super influencer like you guys are, but there's enough people that know the digital me that they already know what to ask me. Right. They've already watched me in an event. They've read the content. So like

8:35 They ask me things without thinking it's a prompt or prompt. They just ask things they want to talk about their deepest fears. Like I I've partnered with Sam on this podcast, but I'm not sure he's committed as me. I see him doing other things. He's into this accounting software and this Hamptons thing. I'm worried he'll quit my podcast on me. What do I do? And my AI is really good with talking that through you, right? And so people just think ask me. How do they know all this, Sam? You think it's funny, but like you might have to do it. Jason Jason. How about you shut up? Well, now you but there're there are thousands of these types of conversations. My co founder's not as commit My I don't know if my board's gonna fire me, right? I is is I'm only growing eighteen percent.

9:16 I have eleven months of runway. Were you Zuckerberging here? How did you know what they were saying? Was there some privacy here? How do you know what's what's being said? It is interesting. And on this app, you can set how much privacy you want. You can anonymize everything. No, you can. No, because there's different use cases. If you're using it as a support tool, think about it using it as a support tool. You don't want an anonymity for support. How can you follow up with someone? Right. Right. Then there's like a therapy level where you would want true anonymity. And then there's like a sl everything's a slider in AI, in in a sense, right? Everything's a slider. You said the therapy thing as if it's like, Can you believe that? Yeah. I'm like Dude, I use

9:50 Yeah. Well everyone does. Like the majority of I'm like This email pissed me off. How do I reply in a graceful way? Or like I argued with my wife, or I'm upset about that I'm not doing this. Like like D the other day on Sunday I saw someone who had a super fancy home and I was like How do I get over envy?

10:13 You know what I mean? Like it like that's all I use it for. It is. And this is the same thing, it's just because it's got the twenty million words. For Business to business content, sales content, scaling revenue. It's at it turns out this and this was a surprise to me. I didn't believe this. It's better much better than chat GPT. It's much better.

10:32 And you you you said something like you trained it afterwards. Can you just well what do you what do you mean by that? Well, how did you train it afterwards? Well listen, I'm gonna embarrass myself technically, okay, but basically those twenty thousand words. It you basically rag it, okay. You vector twenty million words of my content. You turn it into a a a a a very s uh a a database, a set of and and you just add that to chat GPT. Or Claude or Deep Sync. And the way you add it and the relative weights of my content versus the generic content radically changes the output. Like ChatGPT never asked my permission. It's already slurped up all my content, hasn't it? Every single YouTube is in ChatGPT.

11:09 Everything I've written. I haven't been paid a nickel. So what's interesting is that content's already there. But by weight by heavily weighting it toward my content. For my type of knowledge, it's much it's not a little bit better than ChatGPT. It's like much better. Right. How do I do how do I create a sales comp plan? I have four SDRs and five AEs.

11:29 Uh our a our average deal size is two K a year and we wanna go from two million to six million next year and and My team won't really do outbound. ChatGB is going to give you a very mediocre answer, but my AI is going to give you insanely good answers, even though overall we're pulling from the same content. Right. And so you you had to do that manually, was that the training or did you do more? Did you do more training than just that? Well, first of all, it auto updates every day.

11:54 Which is better than chat GPT or Cloud. It auto updates every day. It slurps up everything on My blog, on my social media, on my YouTube every single day. It does it essentially almost in real time. Okay. And then yeah, you it does it itself. It auto updates. Now what I do do, here's what I do do. is and uh it I'll tell you my learnings and like hallucinations. Okay. I audit a few of them, I read some

12:15 And I see if they're wrong, right? I see if the ones that are that are not anonymous, if they're wrong. And when I see something that's wrong and I'll tell you what I learned if you're interested Then I there's a section where I just train it, right? And I say, No, um, Sam and I first met in two thousand and four sixteen. after I wrote a quorum post and he had me do a a meetup at the hustle, okay, because it got it wrong and made something up, okay. So I do I do that for about ten or fifteen minutes a day and it turns out it doesn't get very many things wrong.

12:43 And the things it does, it consistently gets wrong, and I'll tell you why, and then I just fix it and the next day it's right. The ne if you do nothing and you don't train it and you put no content in Yeah, uh this b this this average V V P of sales is gonna say, uh, it doesn't work. You know, I I w I logged into chat GPT a year ago and it hallucinated. I'm like you're gonna lose your job. But the hard the hard part here is like so I'm so committed to chat GPT, so it it it it it knows so much of my information because we've had so many conversations. It does.

13:11 Are we all gonna have like files, you know, like our health record where it's like uh, you know, my the background because it sounds like I get nervous to switch to any other model because I'm like oh ChatGPT I've already asked so many questions, it already knows everything. It's an interesting question. Here's what I've learned. First of all, memory is a big deal, right? ChatGP could already remember questions, but now it's remembering everything. Okay. So so it's a moat. From The top folks I've worked with on this, there's on the one hand, it's a it's a moat just like being in the Google ecosystem is a moat, just like back being back in the day, being in the Yahoo ecosystem was a moat. Okay. But the mode is not as deep as we think. Our ability to get up to get trained and up to speed does not require twenty million words.

13:49 So yes, it is a moat, but if you decided Claude was much better for you and you s the point is and you spent a month Just including your day, each day. You you're probably there. You're not a hundred percent. It's enough. It does. Somebody had a good startup idea. I think it was Aaron Levy or some somebody was tweeting this. They they were talking about Plaid for AI tools. So basically you'd be able to just like the way Plaid lets you connect your bank safely to any financial service. To be able to take your kind of

14:15 memory and context what what chat GPT knows about you, but port that. To some new app that you're trying. Without without handing over everything, but allow it to pull from that. And I I was like, Oh, that's a that's actually a very interesting idea. If apps will even exist in the future. Well w what will exist instead of apps?

14:32 Why we're going through a transition phase, right? We're going through now we're chatting once again. We've been chatting since the ICQ days, okay, since AOL. We've been chatting at our keyboards with people. Now with AI, we're chatting again, okay? Uh, but we're starting to not even know where we're chatting with, right? Right now already uh like M C P is new, but already today OpenAI and Claude can pull from other apps like HubSpot and others and and Notion and just pull the data out. And I don't have to go to Notion or even Google Calendar or HubSpot anymore, right? Right. As we live in this a and then, you know, people think this Johnny I thing for six billion's crazy. It's a great bet. Because we're gonna go from twenty minutes a day, twenty two minutes a day in chat GPT, to twenty four hours a day in chat GPT.

15:13 And when we're in chat GPD twenty four hours a day, we're not gonna like pull up a CRM. We're not gonna use the interfaces like these interfaces are all Already dying. You can see it, Sam, and the amount of time you spend in GPT. Like then go to like a B2B app, you're pulling your hair out. It's so dated, isn't it? Yeah it's so dated already. It's only twenty twenty five and it's already dated to go to any B to B app. They're all gonna die. How does the excitement in

15:39 rate of change right now compared to I don't remember if you were involved in ninety nine in the year two thousand. But you're you were Mm. Close, right? Yeah, I was a kid. It was my first job back then. So how how's the 'Cause everyone talks about the dot com boom and I um

15:55 I never got to I mean I never experienced it, but how's this how's this today compare to then? Those days were the first were the first time until AI where people feel like they could just do something out of nothing. Like it was miraculous. It was miraculous. And that is what AI is like today. People are just doing miraculous things and it's exciting, but man, it's super scary for incumbents. It's super scary for incumbents. Do you think that everybody who is maybe a content creator at least, um, is gonna have this sort of like The stunt double, this this intellectual stunt double the way that you created here. Do you see it once you've did this experiment, are you like this is the future or this was novel, but no, I don't think it's gonna last. Like you know, where's where's your where did you land after the experiment?

16:35 I well, first of all what I think I'm not a consumer content creator. I don't think anyone is gonna create content without AI going forward. And the tools are gonna change. Um, like for example, just for for our last big Saster event, like I did all the speaker promos in Higgsfield. Have you ever used Higgsfield?

16:52 No. It's incredible. How do you spell that? Pigsfield. It's the X head of AI from Snap. It's one of the coolest apps on planet Earth. Everyone's talking about this new Google video thing, right? But they were already doing it. Hicksfield.ai. All you have to do to Hicksfield.ai. Is I can take a screenshot of us right now. I'll put it in Higgsfield and it will create a movie out of it. Okay. And it will and you can and there's a lot of different ways, but there's a really simple way you can do it. You can take a an initial photo and an end photo, and it will just connect them with the narrative.

17:19 So I had like I would take like a picture of Yamini just off her head shot off hub spot. And then take a picture of like a stage at Saster and it would just make a video of of Yamani waving to the crowd and running on stage on Saster and being excited. And so a year ago, all the all the digital promos were a static, you know, a classic static head shot with Some chrome around it. Today everyone got a video a really cool video. Right, next year. It will be me and Yamani talking for ten minutes about AI, and neither of us will have had the conversation.

17:47 It doesn't mean I won't exist, but of course that's already come th we could already almost do that. But I did all these things. Now I did instead of waiting for our designer two months to do a static uh thing and upload it to Dropbox and me forget where it was and lose the URL and have to do it. Now I just did it myself in Hicksfield in like ten seconds. So looking at Higgsfield. This is This is insane. It's beyond cool. It's so good. So good. This is the

18:11 This is why AI is exciting because the really badass people can do crazy stuff now. It used to take a badass person Like Six months to do a prototype and then two years to get a good. Now someone epic like the ex head of AI and Snap can like what you can do at Hicksfield will Blow your mind, right? Dude, I can even tell just why the way you're talking. I feel like if we did the same podcast, you know, five years ago. Yeah.

18:31 Your rate of talking would have been like ten beats per minute lower. Even twelve months ago. There's like a baseline level of excitement that has just risen. Like our new blood pressure is here. Well, as long as I've known Jason. You were borderline grumpy. Like you were pissed you were pissed off all the time. Like I Yeah, yeah, yeah, yeah. You were like look, like I remember you you weren't tired, but you were you were tired of people asking you dumb shit because you always had this you had this energy of you where you were like Talking to someone and you're like, you're making a mistake. Stop this. You're making a mistake. You had like this like almost anger in you. Now it's the exact opposite. Now you're you're optimistic. Yeah.

19:08 I am I am y you're right. I I I'd like to think of it. differently, but you're probably right. You the way you perceive me is is important. Um it it is. I am very optimistic about it. But the difference is I used to think all these products were durable. That they were durable. Now I don't think any of them are durable. So what's that mean? When I first started doing this Saster content, I made up this expression, which I stole from the mayor of Tel Aviv and people have used it ever since. Zero to one million in revenue impossible. We don't need another product.

19:35 Okay. One to ten million of revenue unlikely. Like there's so much competition. Ten to a hundred million, inevitable. From impossible to inevitable. We had a book that sold a couple hundred thousand copies. That was his theme. So you go this stage because What I learned as a B to B founder is you're saying get getting from zero to a million is really, really hard. Getting from one to ten feels impossible. But once you're at ten, unlikely. Yeah. Unlikely. But once you get to ten

19:59 It's inevitable to get to a hundred. If you had good founders, it was a punch card. Now it's disrupted. Now zero to one is very likely an AI. Like it's like you build an incredible tool that no one else can do. You can do a million in a week or two, but like now everyone beyond a hundred million is getting disrupted. There's so many software companies at a hundred to two hundred to three hundred million in revenue that aren't growing anymore. It never used to happen four or five years ago. Like you hit your punch card. You had Hundred and twenty percent revenue retention and you had a brand. All you need was a brand and revenue retention and products changing about every five years.

20:33 Right. If the product changed every five years and you had a brand and tens of millions of revenue, that means you had meant you had product market fit. Right. High revenue like n high NRR meant it kept going as an engine and this this one hundred and twenty hundred and thirty percent revenue retention engine just kept going. It took you from twenty to thirty to fifty to a hundred and it was like And that's why you know in in in you know this crazy in twenty twenty one twenty twenty one, the average public SaaS company traded at seventy X ARR.

21:01 Public. In twenty twenty one. It's it's almost imag unimaginable today when it's at five, right? Right. But it's because it worked then. Like everything just worked and now. You know, I I you know, Okta growing 10%, Salesforce growing seven percent, like the they're they're good companies, but it's not durable the way it once was. So are those companies I m my premise or what I thought and what Morgan Stanley I I thought because Morgan Stanley had this report Which

21:25 Who the gives a shit about Morgan Stanley, but they said that the majority of uh value creation in terms of market cap for uh AI is going to be the big companies using AI to get better versus Yeah, new AI companies. Do you disagree with that? I think that Right now today as we record this

21:46 There's a hint of truth to it and and um but Salesforce is not accelerating. Okay. Octa is not accelerating. Lots of folks are not accelerating. ServiceNow has a lot of AI. But it already had workflows that were automation. So People say that and there's there's there's there's some there's qualitative proof of it, but we haven't seen it

22:05 in the numbers. Okay. So there's a window for the big guys to leverage this because The the interface that we talked about is dying. People are not gonna wanna use these dated interfaces anymore. So Even if it is benefiting the big guys today. Um What is the value of a CRM if I don't you log into the app anymore? If I just talk to to chat GPT and I say, give me the 10 deals I have to work on this week.

22:32 Like how valuable is one CRM over another, or will I even know I have a CRM? Like it just becomes plumbing in a database. Here's one problem. Let's step out and I'll t one problem with AI, one problem with AI is there's been too much nerdy nomenclature the last year. Too many oh oh four's minis, O three Maxis, L Lude it's so complicated. Yeah. It's like knowing the difference between an iPhone thirteen and an iPhone fourteen. It's all that's all going away this year. It's all that complexity made sense.

23:01 As crazy as these numbers are, Anthropic went from one to three billion in revenue in five months, they just announced. One to three billion in revenue in five months, okay. And that is basically all infrastructure plumbing revenue. Okay. So when the inf when the in the area of infrastructure, you need to know the difference between the models and R one and this. We're just starting the application age. And in the application age, we don't we won't care what models HubSpot uses. We don't even HubSpot already has a lot of AI. Do you know what models it use? You don't care. Right, you don't care.

23:29 So so these nerdy terms are gonna fall away, but what M think of MCP as the next generation API. And what MCP does. Is it lets any AI or others talk to applications. Without having to w write inside of the AI. So right now if you go to now this it's just rolling out, but if you go to

23:48 Uh and you set it up properly and it's still a little nerdy, okay? But right now from Chat GPD, you can change your Google calendar. You can work with Notion. Tell me how. You connect it with M C you just it well, I could I can't quite do it with you on online. Maybe in two months it's literally when you O off in, it will do it automatically, but I can show you offline. You just connect it. to your Google Calendar. And then there the the it's still a little bit of a headache around authentication and security. Like them there's a little bit of magic to go.

24:15 But not much. And then you can just talk to your calendar and chat. And HubSpot has announced this. So Dharmash but what are you using to connect the two? So MCP is a protocol, right? So it's like a language. Imagine this, right? Like Um

24:28 W you know, we have English, we have Spanish. Then when the internet browser came out, it was like, hey, there's a new language. We're gonna call it HTML. Yes. And you gotta learn that language if you wanna tell the browser what to do, how to show a web page, right? So now MCP is a new language that came out that was basically saying Hey, if you're one AI app and you want to talk to another Application. How are they supposed to talk to each other? MCP became a protocol that now any app who wants to be like, yo If like HubSpot, for example, they want all the AI tools to be using to be integrating in with HubSpot, but they don't want to one by one.

24:59 Go work out a deal and do a technical integration with each one. So they say, Oh, cool. We'll we'll also speak MCP. We we we understand that language. We know how to do that. Sc right basically like how APIs work for for most websites, but MCP is like the AI specific version of that. But right now to integrate with and I haven't ever used HubSpot's API, but I I I'm sure it's a great one. But but that is bespoke. Like each one is different. HubSpot's API is different than Salesforce and Notion and Linear. You have to learn it. You have to get a key, you have to code to it, you have to understand its nuances. It's a lot of work, right? Like you you may know startups, you've done it like why don't you have a HubSpot integration? Well, because it's work, right? Right. With MCP, it's early, but it's just starting. It won't be any work. You just tell MCP to go talk to HubSpot or go talk to Notion, and it will just do it, and all that work goes away.

25:46 So if your AI can talk to any app you, take all the data out. And let you talk as a human. For ninety nine percent of the world, we won't use HubSpot like the way we use it today. There's no reason to log into this app, figure it out. Like how does the UI work? What are these tabs? How do I configure a tab?

26:04 And And the kids these days will never know this, like this generation coming up. They will never use software like we use it. They will never use it. What are the what's the office of OpenAI like right now? Because you're saying like Well it sucks right now.

26:19 But in sixty days it's gonna be the best. Which um is insane. So how many people work at OpenAI right now? And actually, Sean, for you as well. Have you guys been to the office? What's it like there at the end of the day? What's it like at that office right now if they're able to do all these things so fast? Uh I think it looks like they have about Forty five hundred employees.

26:37 I'll tell you what's super interesting. They only have about sixty percent employee retention over two years. Because what, everyone's going and doing their own thing? Probably but It's just trait like if open AI only has sixty percent. Team retention, what's your hope to keep your your A I D You better treat'em really well.

26:53 Yeah. So I have a friend who told me about the early days of Twitter. And he basically he had built a company He was like scraping Twitter and he was like, Oh, this is cool. If pay based on what people are saying I could figure out what's actually trending in the world. And the way he did it was he was like, You know If people people always talk about New York. So if it's if I hear New York a thousand times, that doesn't actually mean New York is trending, it just means New York's already big.

27:16 But if suddenly everybody's talking about Tallahassee. Well, Tallahassee doesn't normally get talked about that much, but it's being talked about as much as New York. That means it's trending. And so he had a separate site. That was like trying to figure out what are the trends on Twitter. Now this they ended up getting bought by Twitter and that's Now what if you go on Twitter, Twitter has trending, right?

27:34 So my friend Abdur was desc I was like, What was it like in those days? And he was like I thought I knew what a startup was. I thought and and I this I related to this so much. He's like basically I thought a startup was I wake up every day and I gotta go try to get some growth and I'm pushing, I'm pushing, I'm pushing the product forward, I'm pushing the marketing forward, I'm pushing my product out into the market, push, push, push. He goes Then imagine like, you know, you think you're pushing and then suddenly you're pushing a boulder up a mountain and you look up and there's a giant avalanche coming at you. It's pulling towards you, right? It's coming straight at you.

28:06 And so he goes, My first six months at Twitter he goes I woke up And I had the criti keyboard like imprinted on my forehead. Like I would just fall asleep at my desk. And I'd wake up and I'm back at work. Right. These like basically that's how I lived for like six straight months because And he's like everybody's making fun of us because the Twitter had the fail whale. He's like, but you j there's nobody had ever scaled a service like this this fast. And so we just couldn't keep it up. And we're like, we were, trust me, we were trying. Everyone thought we were being lazy or stupid. He's like, We are the smartest people. We're trying our absolute hardest. And it was just so so difficult.

28:37 And I think what's happening with a lot of these AI companies is that You know, Sam, you and I I think we probably only really experience push. for the m for most of our startup career. Yeah. It's never felt like I was holding on. It felt like I was Pushing and it got a little easier sometimes, but it was always resisting. Like I have this company now. We haven't announced this. And I just were like, We have this.

28:57 uh AI bot that will come and tell us our qu new contracts and our new revenue. Last week we closed a million dollars in new contracts. In a week. And I was like I have never felt this level of pull. Ever.

29:10 In any business I've ever done, and it we're not working ten times harder. It's just that like the market wants this type of product at a different level. I'm sure that the folks like you know, OpenAI and all these the AI startups are going They're experiencing a start up experience that is not Yeah. We g w it was not anything like what what you and I experienced, Sam. I think it was zero to eight hundred million users in seven months. Is that what Mary Meeker said?

29:33 Yeah, I think so. I just wrote it up on Twitter we could look or axe, but yeah. Ten percent of the world. Ten percent of the world in eight months. Or something like that. So that's why the rate of change is so high that everyone that's like A Luddite or a Debbie Downer is missing the point.

29:48 Right. And before it looked like it was a bunch of looky loss like people were going and testing the product, but there wasn't really high retention. And then they've showed that like the the action it's not just the users that have doubled, but the usage per user has also doubled. Right. So you have like a a a a double of a double. Um and that's

30:07 It's pretty obvious to me now that I'm kind of an idiot for not investing in this company, even at really any price point. Like this is This is basically the Facebook of this generation, right? Like Yeah, I don't think we w realized that open that chat GBT would have eighty five percent market share at the prosumer consumer level. That that would that's what that what all that meant surprise if we if we know because ironically, chat GBT was an experiment. It was a proof of concept. It wasn't really meant to be the product that the the the center of open AI, but like do you beat yourself about this too? Like the way I do, because I'm I I just look back, I'm like how much how many hours have I spent thinking about AI? I'm supposed to be an investor You know, like you're a SaaS investor. This is the greatest SaaS, you know, fastest SaaS bus growing business ever. Are you an investor in this? Did and did any of you have the opportunity to invest in it? I did. But you can hunt it down. You know, that that's on that's on. You could. Yeah. For me, I wanna

30:56 Life is short. I want to own ten percent or more of a startup. And have fun. So hunting something down just is not my vibe, but but it's the way to make the most money, don't get me wrong. Nothing wrong with hunting it down. And and someone's never heard of shot or my first million and just getting some money in. Like that's the smart way to do it. But um I bet you um I bet you Darme so I think on the pod Darmesh, I don't know if he explicitly said fifteen million, but he sort of winked at it when we when we said so. He owned chat.com, which he sold to OpenAI for the what he paid for it, which I think was around fifteen million. And he uh got AI uh Chad GPT stock, yeah. There's a world where that becomes worth like

31:32 In the ballpark of his hub spot stock, I think. You know, that that does it probably, right? I I'm none of my business. But I remember thinking with Aaron Levy was one of my favorites, you know, he was early in stripe, early in Gusta like. J back in the day, Aaron had a window before Box went public where everyone went to him and he had a little time. Like he wasn't it w and he just did all of them. And I'm like Man, if this guy did stripe in the seed and get all like how

32:00 That's gotta be it's none of my business. It's gotta be worth even more than his box stock, doesn't it? Four percent of box, I think, when it went public. And he's been grinding box for like twenty years. I love him for it. Yeah. Wait, so he heard it. There was a window, listen, it's none of my business, but there was a window I've been doing this long enough, right? Where before box IPO'd. He had time, right? And then you just get b you just can't do this stuff when you're public, right? Maybe Mark Bennyov can. And so everyone he was the guru, right? He was the one guy he was and everyone wanted Aaron. And so He would write these checks that you know, t but I know I I we could look'em, but I know he did stripe and gusto and the seed round and a bunch of others, and it's none of my business, but I'm like That's um there are these moments in time that could be worth more than all of his his box shares. And uh so it just gives me even more respect to keep going'cause so many founders, these they have a different relationship to money and investment than a few years back. And a lot of founders would quit today if their investments were worth more than their founder stock. A lot of them do quit. A lot of them do quit now.

33:00 You know what this reminds me of so It took me At the hustle, I think it took me three years to get to a million subscrib a million users. And that was like life changing for me to get as fast as some of these guys are growing. It's like literally like that per hour. And it's sort of like when you see a billionaire who's worth like four billion Like four point

33:20 Two billion billion. And you're like And that point two Divided by ten. Would be awesome for me. Do you know what I mean? Like it's so it's like hard to grasp how big and how fast it how how big these things are and how big they're uh and how fast they're getting that big.

33:37 Well, look, it's slightly under discussed and it's a crass topic. You might have discussed it, Sam Otherwise, but like It's a crass top thing like it's right up here. Okay, today it's worth like forty billion. But now like Open I will be worth a trillion. So my point is that the rich are so much richer. Right. The the like the regular person's like a little bit richer in tech and it's great, right?

34:08 But because the big wins are a hundred or a thousand times bigger than just ten years ago. Just ten years ago. The amount of billionaires I wrote up on Saster the amount of billionaires just in SaaS and cloud. I could find this post, but your jaw will drop how many billionaires are in it just because the mark the the numbers and markets are so much bigger, right? There's already a hundred billionaires in B to B software I wrote up. A hundred billionaires. For the people listening, what

34:34 What personality types Are like who Who's poised like what twenty two what does the twenty two year old today look like who can pounce on this. Um

34:45 Like what's the What's the profile type? Or the personality type of of these people that are just excelling like crazy. I think it's just two things. Um And um the it really probably hasn't changed since

34:57 Bill Gates days, right? Starting Microsoft. Um, but one is um You have to be able to ship insanely good software. Um, which maybe in some business software wasn't true for a while insanely good. Like Pigs feel that you're trying, chat GBD. This is not trivial stuff. Okay. This is like insanely good software.

35:15 And then the second one is you have to like be relentless to owning a market. There was a while in twenty twenty, twenty one, where like being third or fourth was great. Hooray. Like things were so good that like you'd be like well If I'm number four in the market, but I don't have to sell a lot of stock and it's commer and I could sell my company for four hundred million, that's better than IPO and like

35:39 The now the the best founders day are relentless to being absolutely number one in destroying and owning the market. Right. And because the markets are bigger. It compounds to something crazy, right? I mean, again, just one example, but but Samuel I are both investors and owner. And like You know, Adam was what whatever, you know, high school dropout starting this company. I mean, he's gonna disrupt the entire restaurant industry. He's already on the way there.

36:01 Not be number four. And he has an incredible technical co founder, now an incredible engineering team. And that product owner, here's an interesting thing, because I invested in the seed round in twenty twenty one. Adam hates it when I say this, but the product was not very good. Dean was very good, the CTO. It did a lot, the product, but it was not very good. The reason it killed all its direct competitors not

36:21 indirect, it hasn't killed the big ones, is just'cause the software's so much better and that just compounds every quarter. And AI is accelerating that even faster. So you have to build epic software. Uh, but if you destroy these markets, that that's the path. But I just don't think this is a good time to be number four. I c I could be wrong. I could be wrong, but it had its age. It had its time. I I actually disagree with you. I th I I I I think I understand your sentiment, which I agree with, but I disagree with how you're phrasing it of Uh there is it's not great to be fourth or fifth place, whatever. We've had a bunch of people on this podcast that have built apps that were really fast money grabs where they got really big really quickly with tiny teams. And what I would tell them

37:01 Which who what the hell do I know, but I would tell them I'm like this doesn't seem durable. But so keep your team small and ride the wave and take all the money and like do do something else eventually. But It's a little bit different than it used to be because you don't need to build these huge infrastructures. You can have one hit wonders Yeah.

37:17 Crush it. You know what I'm saying? Uh yeah. I think one hit one is the wrong Phrasing but I know what you mean, which is that

37:24 You can yeah, a base hit now can provide you enough cash flow to A, change your life and B set you up with like five more doors, whether it's investing or it's reinvesting into another company you start and it d you don't have to build one twenty twenty year durable company in order to to be a winner anymore. So I think I think I just I would say like Back when we were in San Francisco early on, like the small lifestyle business. Would get you the equivalent of a job. Now we get to the equivalent.

37:49 You know, like you would make a couple hundred thousand dollars if you had a lifestyle business, you know, that was like It was working, but it was small and it was solo and it was bootstrap. Now those same solo bootstrappers have like eight million ARR. So it's just a different scale. That I can't I remember. But do you know what the difference is though? That that is I think that term is you have to be thought about it. In the age of AI, when there's so much competition, you can build a two or three person company that's small, but the lifestyle businesses are being slaughtered.

38:17 Because when these three kids come to S F working in the mission and they're working eight days a week And they've taken your little idea but made it much better, your lifestyle is gonna be unemployment. So this term I think needs to die. It it made some sense, I think, a few years back. It's okay. I just worry people are gonna take the wrong lessons from it. You have to work starting this conversation. You can do more with fewer people, but you better work harder if there's comp you or find a space with no competition, right? But the weird thing about AI is

38:45 is there's competition in spaces that two years ago had very little competition. Like what's an example that comes to mind? I'll give you an example. I in when I started investing, I did a couple of investments in legal. I knew a little bit about legal, okay? And no one wanted to invest in legal. They're like, uh it's takes forever. Lawyers don't buy anything, it takes forever, it's boring, it's a slow market. Now there's a five hundred AI legal startups. And there's reasons for that.

39:09 But you could not Be at that sleepy pace. Um, same thing. I've done some of the best investment I've done has been in support in post sales. Okay no one wanted to do this type of startup, boring resolve tickets, pick up the phone, right? Now there's thousands of voice startups. There's thousands of these. And so if you think you can run a lifestyle uh customer support startup. Good luck. Right. Good good luck, because Delphi out of the box is probably better than you. You you own a uh a media company. You own you own basically if we uh a trade show.

39:41 That's incredibly successful. So let's just categorize that as a boring company that is not a technology company. For sure. Which is what which is what I do as well. And uh Sean has done something like that uh in the past as well, I believe. For the people like Like that. How are you using AI in like a bull in a in a in a not tech company? Are your employees now becoming significantly more efficient?

40:01 I mean we only have two people now. I take it back. We have five people. And we do five million per person now. Did you have more people before? We had much more people before. We had people in twenty, twenty running I didn't even we have four designers. Now we have a a little bit of a designer in AI tools.

40:17 We used to have five people on this content team reviewing sessions. Now we have zero. Now we just have AI. So we got we have none of the designers, none of the content people. Uh all the ghostwriters are gone. They're the worst. Right. Well, I write my own content, but let me drop you off at the airport. Let me go in verse order. Like, okay, nine months ago, Yamini would come to a Saster event, she's done it three times, okay, and she would speak And three months later, a ghostwriter would write up a terrible summary of her thing. Just terrible. And I would cry and we'd ask them to fix it,'cause I can't do everything, right?

40:49 And then about nine months ago they got better. They actually they got they weren't great, but they got better. And I hadn't actually used Claude. And then I went into Claude and I'm like This she just put it in Claude and they store charging us five thousand dollars a month for this. So like we can do this for twenty bucks in an hour instead of five thousand dollars and waiting two weeks with our clients, right? So we didn't need the ghostwriters we got rid of first, right? Th then we had five people, then we had an agency we worked with for years and for a while it was great and they would review all these speakers. It's a lot of work to work with speakers. You've done it, Sam. And when you have hundreds and hundreds of speakers, it's impossible to do it all, right? But they decided to be a little bit more than that.

41:22 they just didn't want to work that hard anymore. So they own they wanted to charge us two to three times more and only do half the work. So it just didn't help us, right? So then we're like we're we're SOL now. We're five months before Saster annual and we just said, Well let's have our AI do it and it It reviewed three hundred sessions, three hundred slide decks, three hundred presentations. Do you have to chase those three hundred people down to give you the Yeah, we still have to like it doesn't get rid of everything, but it does ninety percent of the work. And it better and it does ninety percent of the work three times better. Ninety percent of the work three times better. Was that you, the business owner, who had to architect and come up with all these solutions?

41:56 Between Amelia who runs Faster this media business and events and me, yeah, we came up. No one else was like motivated to do it. Of course. Uh makes sense. And uh and then like we have a time you know, we have a little bit of the sales team, but then RAI just started to do all the screening and initial sales conversations for us. That helped a lot. Even for it's uh this It's a very niche.

42:19 business, a trade show business. Exactly. To say you do twenty five million in revenue with five employees is pretty breathtaking because I would have thought That would be on the lower end Your business would be on the lower end of like, Well, I still need people, but you have just proven that not to be true. And so It could do better with more people. It could do better with more people.

42:39 It's not on the life gets your life gets worse. No on the honest I don't mean to get off target. The real problem is I just can't it and Sam, this is why you think I'm grouchy because of early conversations we had. I've just struggled to find enough A tier talent that wants to do this non-sexy stuff, okay? I would love to have twenty people on the team tomorrow. I have budget for it, or at least fifteen. Uh but but I don't need someone that shows up to a meeting with a sponsor and doesn't know what we do. Okay. I don't need a a designer that doesn't finish the design until after the event, which I had once in the past. Like sent us a big bill but didn't finish the assets until after the event. I just don't need that, right? Um, you know, I just don't I don't need I don't need someone managing

43:20 10,000 people in in our in our Saster annual that forgets to do catering. Like I just don't need I'd rather have the AI come up with the catering the AI did our catering schedule this year. Could you talk about the start of Saster real quick? So when you started this thing, you had Soldier Company. Yeah. Right was it was it after you sold Ec Echo Sign or a long time ago, twenty twelve, but yes. So twenty twelve, you sell your company.

43:41 Great exit. I as I understand it, you're like I've I've retired twice I got in shape. I picked up a hobby and realized, you know, like I still love building. So so you sell your company, do you retire right away, basically? You take a break. Well b after Uh uh there's probably a little bit of parallel to Sam here. Uh both times after I sold my startups

44:01 Ice. sort of didn't work for the better part of a year and just got restless for different reasons, right? And I just got restless, and in fact Both times after about a hundred days, 120 days, I got a little depressed. Maybe depressed is too strong word, uh lost, lost, right? Definitely lost. I remember

44:18 Uh, you know, my second startup, Emergence Capital, which is a very successful B2B venture firm, had a CO every year I had a big CO meetup, right where they would come. And in my the in my class, my group, I had David Sachs. Um, and Aaron Levy and Peter Gasner from Viva and Renee is hurt. And then after I got acquired, I got to go to one more and they said you can't come back anymore. You're not you're not part of the uh I'm part of the the COs anymore. I didn't I got I I was off the team and um You know, Ben Chestnut did an interview just a couple weeks ago with Kleiner Perkins. And said the biggest issue when he sold Mailchimp for twelve billion or whatever it was, is was he knew he would be instantly irrelevant.

44:55 He knew he would be instantly irrelevant. He said, I am now. I'm irrelevant now. Mail chimps of the past. He's like you wouldn't even build a tool like an Ill Chimp today in the age of AI. Mm.

45:04 Right. Maybe that wasn't quite the point. So yeah, so so that was it and then But then what was fun for me, and this is is a long time ago, but what was fun for me is because I was the first of those COs like the Erins and the David Sachs that had an exit. I didn't have to pretend anymore. So I just maybe Sam thought I was grumpy, but I just shared every mistake I made, how I screwed up my first VP of sales, how I screwed up Um, meeting customers in person, how I screwed up marketing, and there wasn't much content back. It's a little different than today. There wasn't much content. So everyone just started to read this.

45:31 Were you being strategic? You're like, Oh, I'm gonna start doing content marketing and that's gonna lead to this to lead to this, or you're just like, I've got time on my hands, I Got stuff to say, I wanna start blogging. I did what now people give advice to, but I didn't there was no one to give the advice. I just wrote one blog post a day on a mistake I made. That was my my paradigm, right? A mistake I made as a B2B founder that got to tens of millions. And back when Cora was a platform and people listening to this won't even know what it is, but Sam will, I answered one question.

45:59 I answered one question. So peop this was a way for people to ask me questions. And they those were great because they were very Tactical, right? They were very specific. So I would do one a day. Every day. And it it does, you know. I would It's a little different in AI, but generally speaking, if you do that, it compounds, right? It doesn't compound the same way revenue does.

46:17 But if you do my first million every week and you just keep working at it and you it does seem to compound, doesn't it? Just not in not quite as linearly as we might hope but It does compound. But I didn't know one there was no advice back then. I just did one one and one a day. You're also one of the first people to do Twitter. You're one of the first to like uh tech people To like you know, for a lot of tech people, Twitter didn't boom until Covid.

46:40 Um, but you were doing it very early, you know, it was like you and Gary Vanderchuck. Twitter started with technical. What do you mean? I don't think it was taken seriously. I think that uh I think Jason looked at it as a craft where he was like I'm gonna grow a hub huge audience here. I I think Sean that For a long time. Twitter was an afterthought to a bunch of different social media platforms. Now I think it's bumping.

47:00 I just think I approached it as a micro blog, which is what Twitter in the old days called it. So I would put valuable content on Twitter. Instead of being grouchy or just just just you know, be pee and so I was early to putting valuable content, I think, on Twitter, right? Um, I think if I benefited anything in content, I think it was just being ear. You were early? You've been

47:19 Dude, you are an output machine. And the stuff that you write about Is lyrical. Like you write about thing SAS is a stupid, boring thing. You write about stuff where I'm like, I don't even own a software company, but I wanna I love reading what he's saying. You know, it's kind of like die workwear with clothing. It's like you don't have to know about clothing, but when he talks about ties, for some reason it's kind of exciting. Well, that's a good insight. My actual real goal of doing it was to make it more fun. Building boring business software, make it more fun. Not not not in jokey way.

47:47 But to celebrate the fun part the exciting parts of it, right? That that that was my version of what Sam said. Did you think, okay, then I'm gonna be investing, this will help with deal flow, and like where did the conference come in? Because that's a k pretty gangbusters business. I can't imagine you thought at the beginning we're gonna be doing five million dollars per employee. We're gonna do twenty five million dollars a year in this business where we have kind of like a little Like our monopoly. We're the big fish in this small pond of Of of Basically like thought leadership for SaaS businesses.

48:16 Well, the pawn there's more thought leaders today, but if you if I mean it's a while ago, but if you are curious I just wrote this just Because I was a blue uh and and with something to do, something to share, something to add value to the world, right? No goals. No goals.

48:31 Um, I certainly wouldn't start off with a blog today if I started off today, right? Is as archaic it is. There still is SEO, but What what would you do? Even it's not me, right? But of course I would do video. I do video, but I'm not you got like it's not my natural I'm a good writer. I'm not like uh Ern Ernest Hummyway, but like Sam said, I have something special. I'm able to convey ideas in a way that helps people in writing and I still think today that's a rare skill, right? Dude, I hate video. Sean's pretty good at it. Sean can talk to a camera by himself and and succeed. I hate it. I hate video. I think that like I think there's a generational gap. You need to put a like a supercut of Sam's ad reads. Oh my God. They suck, dude. It sucks, man. I I it's not I I'm incredibly uncomfortable doing it. I think but I think that like the

49:18 twenty five year olds today, just like the fact that FaceTime has existed, they're so much better at it. Uh, so there's like a huge there's a generational gap that I'm like Four years too old to have caught. But if it's of interest, uh i i it might not be. The investing was an accident too. It was an accident. I actually For about

49:36 Little less than Two years I worked at a V C firm That had invested in me. So they they recruited me to help them. I had no real interest in investing And I showed up and I like I don't know what the hell like this is not me. I don't know what to do here. But luckily I'd started this blog and founders started to come by the office. So

49:55 First the founders of Pipe Drive came by the week I started, and that was my first investment. That sold for a billion and a half, right? Then other founders started, then founder of Talk Test came by. That one was worth 10 billion in this last round. Then the founders of Algolia came by, that's worth two and a half billion. Um, then the founder of Sales Off came by. We sold that for two point three billion cash in twenty twenty one and they kept coming by and I'd be like, Well, let's just invest in these ones because these are the best ideas I got. Like I'm not the outpound guy, like finding Sam Hallman. So I just invested in the five best guys that came by the office the first year, but they're all worth ended up being worth a billion dollars. So

50:28 So that's I I only so the weird thing about me for investing, and then I could tell you about events real quick, but I don't spend all the time. I only I've I'm different than ninety nine point nine percent investors. I only do Saster super fans. that are high intent inbound. I don't take favor meetings. I don't do warm intro. Uh, if you tell me, Sean, there's a startup that you want me to meet to invest in or Sam did, I would ask, is this do they desperately want me?

50:53 And they'd be like, No, they haven't heard of Saster, I'm out, right? But if they really want me, they probably just email me. So I don't even want a warm intro. I don't even want a damn warm intro. That sounds like such a leak in your game, by the way. That sounds like an unnecessary bar, right? Like not only if I get a warm intro. That they say this person's kick ass and they'd love you know, but it's like

51:13 Are they a huge fan? If they're not a huge fan, I'm out. That that just seems like the thing is like unnecessary. Investing so much harder than it looks The odds that any start like seed startup's gonna truly be worth billions of dollars is much lower than it looks in the media. It's really hard. And if you don't have like if you're not incredibly intense, if you're not incredibly if you don't want this more than life You're not you're gonna you're just gonna sell your lifestyle business, which is very logical.

51:37 Oh, so you're basically saying If they're not like Basically Digging my content. they're not taking as seriously as they should is that is that the implication basically that

51:47 If somebody is seriously trying to build a generational company, they should be loving our content and therefore they should want me on the cap tape. I want them sending me a cold email that is so good. that you would invest off the cold email. This is how I invest. I want a cold email that is so good. That is so good that you don't even need you almost don't even need to meet them. The only point of the meeting is confirming That you want to invest. Like every investment I've done that's good. I've wanted to invest before the meeting.

52:11 Every good outcome I've had that's a good idea. That's how I invest in the in uh owner. I'm a little bit after you guys, but I got an intro that was like this guy's One of the best founders I've ever met. And ever invested in and this this company's growing incredibly fast. Yeah. And then he sent a cold email basically right after that, which is like, Hey, here's why I want you on board. And here's my last three investor updates. And in that, one of the things that he shared was

52:33 They had done like a hack week. So there was like some loom videos of the team sharing their Hack Week projects and I actually just watched those. Yeah. And it just show like the the c calibre of the team was Really incredible. Like you can see the calibre of team in a Hack Week project, right? Cause almost by definition it's Here's just like one or an engineer and a designer. They come up with their own idea. They have a very short timeline to ship it, and then they have to pitch it and present it. So you get to see like.

52:57 The the quality of idea, the quality of speed of execution, and the quality of salesmanship. All in one from like Without w abstracting away the founder. It's like that's the team uh itself. And uh I emailed him back with you know, I was like we don't need to meet, I'm in. Yeah, you that's it's not the only way to invest, but what I can tell you is if the m email's mediocre, they're not gonna make it.

53:19 There are exceptions, okay. I know there's exceptions, but man, to dude, so we just um W uh uh Hampton we're hiring a bunch and I'm putting together like values to look for when hiring. Yeah. And I only made it um Uh I think I'm only gonna keep it at like two or three values, but ability to write an email and communicate is the is one of the three.

53:40 And I will tell you of the re one of the reasons we only have the five people is I have lowered the bar At Saster in a way I never would as a software founder. I've lowered the bar again and again. I've hired folks for the email, wasn't that great? I've hired folks where they put an E in Saster. I've hired folks that didn't do the research before they started. Hundred percent failure rate. Hundred like we already know this, right?

54:01 But I've I've lowered the bar'cause I've been like, Well, this isn't as cool cool enough. Well, I gotta take who I can get, right? Always always a neg uh n worth less than zero. Right, total, total zero. Yeah, you have this great tweet. You said you think startups are about a great idea, but in the end they're about great recruiting. That's what you're talking about. They they Yeah. And

54:21 If you talk about owner, not to use one, but it's a mutual point, I will say there there actually l are lots of risks with owner and I invested very early. You didn't see the two times we almost ran out of money. Now we have infinite capital, a lot of other things, but I actually do not know a more relentless recruiter than Adam. I don't know a more relentless recruiter than Adam, and that That is a rare skill. We all learn it as as COs, like we get bet we always get better at recruiting, right?

54:46 What does relentless look like? Like what does that mean? Literally reach out to the two hundred best people in the job. Talk to all of them. Set up means cold, warm, lukewarm, direct, LinkedIn. Who are the two hundred like talk to everyone well. Who are the t two hundred best CMOs that I could possibly hire? Don't pretend to talk to two hundred. Don't actually only do five interviews and pretend you're doing them. Do two hundred.

55:07 That's what the S tier recruiters do. The asked your I had an old co founder and I wish we'd gotten along better. But he was one of the one of the best I ever knew. And I'd roll into work every day at at eight o'clock. And he'd already handed me two candidates to talk to that were really good every day.

55:22 Every day. I've never s Adam has that, but I've never seen that magic, right? And I don't have that skill to every day he'd found a way, hey, I've got this marketing this sales guy wants you to meet. to can you talk to them today two more, but then they'd always be great. They they're not they won't always be a fit, right? And that's that's how you only way you can scale as an executive unless you have a three person startup. You have a few more of these really great, like how to be a great CEO. Concepts. So one is to be a great great CEO, you have to enjoy telling the same stories again and again and again hundreds of times. Yeah.

55:54 Yeah, even Sam Altman does that, doesn't he? It's pretty much the same story, right? It it it it is that That one the what I like that Sam does I can comment he tells you the future like Elon Musk if you're listening. What do you mean by that? Well

56:09 You know, he does this you can make fun of this goofy video he did with Johnny Ive. I don't know if you saw it when they did it. Like perfectly lit and having coffee in North Beach. My favorite rom com of the year, I Yeah, you think oh this is silly, right? But but listen to what he's saying. He's telling that In the not too distant future, you will be on chat GPT twenty four hours a day. And I'm making the bet that Johnny Ive is the guy to do it. I'm not betting that he's gonna build a rabbit pendant. It's not that. I'm making a big bet that he knows UI and UX so well for the next generation that he will solve this problem where we are on. And Sam's already on Chat GPT more than the average today, right?

56:46 The average person's on like twenty two minutes. You said you're on it more, aren't you? I'm on it all day. Yeah, so Johnny Ive is gonna figure out a way that it's in your ring. And it's in your phone and it's in your glasses like Ray Band. And he's gonna figure out stuff we haven't figured out. And it's in our it's in Sean and I's headset. And we are just like what if it was in this headset?

57:01 Like this is totally passive, right? I mean, I don't know if you guys have used granola or the newest notion. It records everything you do all the time in the background without permissions or visibility. Do you know why granola is so successful? For note taking versus I don't know if the one you said is b does this, Sean, but uh you know, granola just records everything at the hardware level. Like I could be recording us to granola right now. And you uh we had we had we had a chief customer office officer summit, three two hundred of the best chief customer officers at Saster this year, and the guy that put it on that day wrote up the whole summary of every single session. That day. Like very, very good. I even I couldn't do it. It's like oh yeah I just granola just listened to everything and it wrote it for me and it was done that day.

57:40 Do you feel this way, Sean, where I hear this and I'm like, This is so exciting. And then but the other side of me is says, um This is so intense. I have to like I hopefully I can invest in something and and make a profit. Otherwise I need to take my winnings and go home and hopefully they compound compound by themselves because there's an intense future that you're painting here. Like I I don't know how I feel. I I sometimes I'm like, This is so exciting. I want to get in this is this is amazing. But then other times I'm like But if my life depends on this, I don't want to play this game. So this seems so intense. I know exactly what you mean. I've I've now experienced basically like I graduated 2010. Right. So when I graduated

58:14 I Basically, like that's when the light bulb turned on. I don't I don't I don't even remember life really before that. You know, I d I didn't even know the great financial crisis was happening. I was sitting at a Chick fil A somewhere in oh eight, you know I I just was oblivious to to the whole to the whole world, right? But when I came out twenty ten, uh basically three things have happened since then that were of note. There was mobile. So right when I moved to San Francisco, I remember we join uh you know, I joined Birch's startup studio. And there was a single mobile developer, and he would the my very first day, he was giving a tutorial to the other twelve engineers who were like,

58:45 You know, super seasoned Silicon Valley engineers, but they're just never built an IOS app before. Yeah. And I'll and like that ratio of like one mobile developer to, you know, fi twelve, fifteen Non mobile developers. Within twelve months it flipped. It was like if you're not doing mobile, what are you even doing? Why would you do a startup if it's not a mobile startup? It was like a a a a dumb idea in by the time you're, you know, a year later into the job.

59:08 And so I saw mobile come and mobile was one of those where I would say it was obviously going to happen, but it was a fog of war. You didn't know where the opportunities were. And actually the opportunities were Very different than the previous wave. So like Michael, who had made a billion dollars And Web One Point O or two Pointer, whatever, like you know, the Facebook era.

59:27 He didn't realize, even Facebook didn't realize Zuck didn't build mobile apps, right? He was like No, it'll be mobile web responsive. That'll work. And You know, w the fact that basically Uber was like the big Uber was like the biggest winner basically during that like That era when we when we launched.

59:42 And Uber was like physical world interaction. You push a button, but a car has to show up, and you have to manage these drivers and That looked nothing like the winners before. So there was like we all knew Oval was big, but we didn't understand The the fog of war prevented us from seeing the path to victory. Yeah. Then the next one was crypto. Crypto had a different flavor, which was

1:00:01 It it was a not consensus that this was gonna be big. In fact, it was very fringe and you looked a little crazy for saying this was gonna be big. And so most of us missed it for that reason. Um, and now this is the really the third one. I I'll like take Covid out, uh,'cause that was that was a little bit of a different thing. Uh this is the third one where again

1:00:19 Everybody agrees this is gonna be huge. This is gonna be the biggest of all of'em. This is the biggest opportunity ever, right? So everybody agrees on that, but there's complete fog of war because like you're saying Even the apps that are working get disrupted. There's like so much creative destruction there. One moment you think it's the models that are gonna get all the money. Then you think it's NVIDIA that's gonna get all the money. Then you think it's the applications that are gonna get all the money. Nobody knows how to win. Uh, even on the investment side, like the VCs also you're sitting there and you have this w really weird feeling because you know this is the time when all the money's gonna get made. The generational money's gonna get made now. You still have no idea where to put it. And people are trying to figure that out in the fog of war. It's like that Warren Buffett phrase where they where he says, um Uh every you see who's swimming naked when the tide comes in or goes out. You know I'm saying? Uh where the the idea being like uh you know, when there's turmoil, that's when you get greedy. But the hard part is A, the courage, and B to know when the turmoil is actually happening. You know, are you in that period? Now we all know it's happening.

1:01:17 Uh this is the time But Do you or I have the want, desire, courage to actually get after it? And half the time I think Hell yeah, this is amazing. The other half of time, I think This is this is scary. I love and read a book. Yeah, I want nothing to do with this. You don't do you guys. Someone on Twitter had a good tweet.

1:01:35 that resonated with me on this point. He's like, Well, the the smartest way if you can possibly pull it off today is to go make five or ten million, cash out, and just chill. Because you can't predict where it's gonna go. Like this is the world's gonna like whatever you could do to m to liquidate your assets now, they may be worthless down the road. So liquidate them right now and chill if you don't if you don't see the future, because this is the time, right? I d I do think And I also think you know, I used to It it wasn't until we ran our own AI again, I used to think Vinode Coastal I mean, obviously off the charts smart, right? But when he used to talk about how AI was gonna bring mass unemployment in tech, I used to think he was just being crazy, right? But now I can see it.

1:02:10 It's also coming. I can see all the uh maybe Kinsey just laid ten percent of their their team off, but it's just a start because They put in all of their learnings, all of their data into their own AI like Saster. And now they just ask the AI. They don't need the kid anymore, right? Half of our sales and marketing teams are gonna be gone in two years. There will be no B DRs in a year. And so this mass change and it it is hard to make bets. So what's happening in Venture for what it's worth, there's really two things happening right now in Venture. Seventy percent of the money is going into growth. And right now it's a great play. You do Claude at a billion and then it goes to three billion and the valuation goes five X. You put in two hundred million, that two hundred million goes to six hundred million, right?

1:02:48 You take home twenty percent of the profits, you make eighty million dollars in a year, right? That's where venture's going. All growth. It's all growth. And then it's doing seed early stuff. But implicitly People are assuming a very high loss rate and they're paying very high prices. Sixty million, hundred million dollar valuations at seed.

1:03:06 And they're hoping it's worth billions, but they understand like There will be uh uniquely high loss rates, too. They're not saying it, but they know it, right? They know it. Yeah. And that seems hard to make money, right? Those two that combination of high valuations and high loss rate. Doesn't that be a good thing.

1:03:23 If you get one per fund at all that that's the bet they're making that there'll be one hundred billion dollar outcome. for each venture fund, right? But back when Hubs again when HubSot IPO the bet was you'd have a billion dollar outcome per fund. One. Now it's hundred billion per fund. So if you believe you'll do that.

1:03:40 You can do some you can do a little analysis or waterfall and you can just have Claude do it for you. You don't even have to do the analysis yourself anymore. I did this over the weekend. You just gotta find one of them and they all the rest can crash and burn, right? So so what is your game plan? I have decided that Whatever brand I still have and my excitement and my ability actually to know more than because I've done my AI actually know more than most people that aren't that aren't on the like Programming tool side.

1:04:05 I've decided that I'll get one at least one ten billion dollar deal done in the next three years, two years. One. No matter w I'll I'm only in it for one. Whether that means I have to do twenty investments or one more, it doesn't matter. Um I I I'm in it for one, right? At the seeds at the early stage.

1:04:24 I want to try to get one deal where I own ten percent or close that's worth ten billion. I've sort of done it once on paper. I've done a couple of billion dollar ones and I'm just and I've missed a lot. What would that be worth to you if you own ten percent at seed of a company that's uh outcomes at ten billion. Well, multiply if it's just ten if it's just only ten billion, that's it.

1:04:44 But multiply it by ten percent. So that's a billion, right? And then you keep twenty or twenty five percent of that. But there's gonna be so much dilution along the way too. That's what I'm asking. You don't account for dilution? No, I'm simplifying my goal. You could own more. Like you'll own more, and then there'll be investments that are highly diluted. So at a at a ten billion dollar outcome At a seed stage, you are looking to make two hundred million dollars. Yeah, that would help. Okay, that'd be cool.

1:05:10 Yeah. I think listen, if you really want to know how venture if you really want I I know we're going off talk, there's two ways that I think venture works if you want to simplify a lot of it. One, it's a great job. One it could be a mediocre job, it could be a great job, or you could try to make at least a hundred million dollars. I think anything else is it doesn't exist. The gap there's a gap. It doesn't exist.'Cause you're either in it for the fees and the job. Like initially, like wow, I'm a kid, I'm getting paid two hundred fifty thousand dollars and I just get to take meetings, it seems great. Then you're finally a partner and you make a couple of million bucks a year and that's like much better than like some other job. But there's a pretty big gap between that, like you don't it's really actually unless you're great, it's really hard to make profits in venture or carry.

1:05:48 So the game is to make a fucking lot of it. Okay. And listen, and the thing is, if you're in a big winner, if you're in multiple big winners, just do the math, Sam. Like that's why most VCs make nothing except A good salary. But there are a bunch that have made billions because if you're in like three or four or five of those ten billion dollar outcomes, which is very hard. Then you make a billion bucks. Now the founders hopefully make much more. It it is fair, right?

1:06:11 But you're either playing that game or it's a performative game or it's really just for fees and salary. Like there really isn't there's nothing in between. But you also have the media and events business too. So you also have this cash flow uh I assume that that's a very profitable business. It wasn't before Covid, but it is now. Yeah. So you you have that either way. Yeah, I mean I made enough as a founder. I have a safety net. I mean but I don't I actually view it as a net negative for investing, but it is uh but it's a passion. Uh we we do a good job. But yes. Last question. I I know you have college age kids freshman, sophomore.

1:06:45 Yeah, what are you advising they're gonna do? W when when they're saying, Dad, you know, what should I do for a job, if they if they ask you that, uh, what would you advise them to do now? First I I I don't think a lot of these kids are will ever have a real job. They'll find ways on the internet to make money so so I It is interesting. There does appear to be a a gender difference, which I don't like between boys and girls. Of my son's my son's a sophomore now.

1:07:07 T ten percent of his class didn't even want to go to college at all. And they just decided that they could they all had this vibe, I'm gonna go to Eastern Europe where it's cheap, and I can just make money on the internet. I'm never gonna have a real job. There's no interest in ever having and I don't think my son really wants to ever have a real job. And he's super smart, like he's much smarter than me, math. He's now into he's deep in AI. He can he's deep into cursor and windsurf. He pays for cursor out of his own pocket. He's running assembly language now so he can code to the metal and do everything. But he'll never have a real job.

1:07:34 Okay, he's like worst case I'll work for Air B and B. From Right. So he's never gonna have a normal job ever. Okay. My daughter, it's interesting, she's at Stanford, okay. And the vibe at Stanford, this is if you ask, it's kind of interesting.

1:07:49 This is a shocker to me. They all want to go to grad school now as freshmen. So they're all they're all architecting their classes, their majors. So then go to grad school so they can defer work. Like when I was in college, people cared about grad school. Then I think people made fun of grad like why would you go go to gr like why would you go to grad school? Like go go go go to the internet, right? That was the vibe for for fifteen years. Now they all want to defer reality and I don't I don't know that there'll be any any jobs and I don't know that people want to work. I honestly don't think

1:08:19 And I don't mean this negatively. I don't think a lot of the current they want to be creators Or they wanna do other things. I just whatever made us want to work, the three of us, I don't see it in the next generation. Very rare. The women wanna be educated and the men wanna Move to Eastern Europe and make money on the early. But the men not wanting to work at all, like like coming out of high school and just saying No fear.

1:08:42 Like no fear I I don't know what it was like when you when I w during my life I was worried I wouldn't have a job at different times, right? I was worried during college I wouldn't uh during I was always worried there's no uh When I was a senior in college, I remember thinking Man, I would kill Torhic KPM G and make forty five thousand dollars a year. Like I I I I remember thinking like that would be a home run. If I could quote I'm like KPM G in Nashville, Tennessee, if I could make if I could get fifty G's from Deloitte. That's a home run. But it's so so I think I don't know that they're gonna work and then I think a lot of the twenty twenty one generation isn't going to work again either.

1:09:16 I'll give you an example. So someone I knew a little bit. Um There's a lot so I've I did this exercise. Um I it just like lowering the bar for hiring. I did this exercise. I know I shouldn't do it, but I want to try it anyway. I reached out to folks that had that circle on LinkedIn.

1:09:30 What's the circle on LinkedIn? Out of work. What's it called? Looking for work? Yeah, open to work. I looked open to work. I worked out to folks that I knew a hint of. I hit maybe I met them backstage at a hustle event or something. I I I I'd met them in passing, okay? Enough that I had like a micro connection. that had been out of work for six months and I gave them uh jobs. All of them in the end basically said, I want to make 200K or more only to do meetings or manage teams. None of them were willing to do any work themselves. None of them. The Gen Z folks their expect their their expectations for salary or for comp is so high. Well there's that too. I'm talking about folks that are already been out of the workforce for six months, but yeah, the expectations are they'd rather not work. That's the thing a lot of people would rather not work than get their comp.

1:10:12 Right. I mean, yeah, that sounds good to me too. I don't know how everyone's like, listen, there's obviously an element of privilege in this, right? And for folks that are living in different geographies or others will think this is disgusting, and I think they're right. But I also think Folks who have made a little bit of money in tech or otherwise are happy to live On relatively low amounts of money with with their savings or others rather than just take a job.

1:10:34 No matter what it's what what the i internet says, right? Um Jason, is this a stupid mental model? I do this sometimes. If I if I want to hire somebody. And I'm interested in there. Two hundred thousand dollars a year, let's say. And let's say my business is twenty percent.

1:10:46 Net profit margins. I think to myself, this person has to basically generate a million dollars of extra revenue. Just for me to break even on their salary. Now maybe they're maybe they're doing it in coordination with a team, but like the addition of this person in order for it to be a positive ROI. I have to believe that adding this person yields me a million dollars of extra revenue. And when I do that

1:11:08 I mean ninety percent of the time, I'm like, There's no chance. No, this is like that that wouldn't even make sense here. Um So I don't know if my mental model is broken. Or if I'm actually on to something with that. Is that how d is that is that a really dumb way of thinking about that? That is that is the model for sales reps. Like traditionally a sales executive, whether they sold software or an automobile.

1:11:27 A sales executive in base and bonus would take home 20% of the profits. If you look at how car dealers have low margins, right? But if you look at the margin, Um to a car dealer. Uh the the the guy selling you the the new the new Lexus Net Net would take home twenty percent of the profit to the dealer, right? If the dealer made no profit, they'd make nothing. If they ripped you off and got you to pay Lyft plus the the CD player for a thousand dollars, they'd make a lot, right? Sales is the same way because in uh in in software, the margins are almost a hundred percent. Reps would traditionally take home twenty to twenty five percent of what they closed, right? Sales. For other roles

1:12:01 Um it it's really just about leverage and you're often just hoping to break even. But even to break even, let's say it's a two hundred thousand dollar employer. To break even, you need a million dollars of incremental revenue to break even on that. Yes, but one way this is what I learned. For example, one way that law firms traditionally were structured, this is slightly interesting. And it may be different today, but traditionally law firms actually most law firms, not the big the not the litigators But like your corporate law firm that helps you on stuff, they never made money on the associates. Okay.

1:12:27 Wha so why would you have associates? I didn't know this until I asked a partner that I work with. He's like,'Cause I just don't want to do that work anymore. I don't want to write the certificate of incorporation for Sam. I don't want to do the NDA. Like I don't we don't make any money net net w met net of training and offboarding and churn and the and the desk and the computer. We don't make any but I just don't want to do the work. So For your organization, you'll also it's like just to not have to do the work, right? But the problem with AI is it lets us do more of the work. That's the weird dislocation. So instead of paying that person Like you can't even find the two hundred thousand person dollar person. At some point you'll just do the work yourself with AI, right? That's the cognitive load. Um

1:13:02 But that's why it's the mix. I don't think everyone can be profitable. Some folks just have to reduce the load on everybody else, but AI is going to do more of it. Yeah. Right. You're full of information. I um You know, I think Theo Vaughn described one of his guests as a blind Russell Terrier or Jack Terrier. Or uh no, sorry, a jet uh a deaf

1:13:20 What was it a deaf uh fucking ruin this joke, but uh anyway. A deaf Jack Russell Terrier where he like gets out of the of the car and he like goes crazy to can't quit stop him from yapping. Uh that's kinda like what you are, where it's like we just like Hit record. And we just like you just roll and we just are on on board and listen to you and uh you're the man. You um You're just full of I think really good comments that are done and like Strong taste and

1:13:53 Jason, uh don't get confused. When he calls you a a blind deaf dog, that's it. He's trying to give you a compliment. That's just he does it a little bit differently. Yeah. Yeah, and grumpy. Yeah, and he goes to Grumpy. So you're welcome. And welcome to the show. There's a goodie bag for you on the way out. Thanks, man. You're the best. Um that's it. That's the pod. I feel like I could rule the world. I know I could be what I want to. I put my law in it like my day's off On the road less travel never looking back

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