Software and Agentic Workflows

Do you know what you're getting into here? Nope. Let me give you the simplest explanation. You know how on Twitter, you're funnier than the smart guys and then smarter than the actual funny guys? We did that in the business podcasting space. I feel like I can rule the world, I know I could be what I want to. I put my all in it like a days on the road Let's by the way I was supposed to be prepping for this podcast. And in the last hour, actually all I did was watch Millionaire Matchmaker seeason three episode eleven, which Aaron, if you remember, is when your co founder went on Millionaire Matchmaker And so I don't have a whole lot of prep, but that was a great episode. Where do you remember when he did that I do. Yes. Were you in support of that? Not exactly. though it was we took a flyer on that one. They actually, well the weirdder story was they asked for both of us to do it. Somehow I had better judgment. So Sam have you seen this episode? Yeah, but so I actually met your cofounder, Dylan. when I was starting my first company in San Francisco, I didn't have a lot of money and we weren't making any money. And I did part time work at a scavenger hunt company Box was a client one time. and so I got to hang out with him And he had told me about being on the show. Wow, really? And By the way, we were like at this bar at like the end of the scavenger haunt at like seven PM and he pulled up his laptop and went to the back table and was like working And he couldn enjoy the scavenger home. Well, I think that's One of the crazier things about Y'all's story. You've been there for twenty years It's kind of like four friends, you know, started in college type of deal. and are all four still there now twenty years later So u, Three of us went to middle school and high school together, then four of us went to high school together. and we had tried lots of different ideas throughout middle school and high school. And then finally, as we went to college, kind of people split off to different schools And then this idea kind of emerged and we all kind of got back together on it and then dropped out of college and kind of two parts in two thousand five and two thousand six. And so we've just been working together for, I mean, honestly, like almost thirty years on different things, which is kind of crazy to think about at this point. So right now we have Dylan is, CFO he runs a bunch of functions in the company He was famous for millionaire matchmaker, apparently, definitely his main claim to fame at this point And then Jeff and Sam, Jeff has a bit of a farm. he's kind of getting into the farm world and then Sam is at Anthropic and on Claude Claude Code. and he now is a constant thorn on my side because every every three days, somebody says the CTO of Bx left Bx to anthropic, but he actually he actually retired from Box like six years ago. but it causes like you know, sort of unending viral fodder on that one That's pretty incredible that you can found a company, take it public and then you go and work at anthropic.'t Isn't the Instagram founder, another founder Instagram? I mean, they have to their credit, they've done obviously an insane job on recruiting. So I think it might literally be a requirement to have been a CTO of like a public company to work there at this point, But like they have like this like like there's like a list of like ten of these people. You know, Mike's over there, obviously now with Andre, you know Sam on our end built, you know some of the most important software and infrastructure that we run on to this day. so he's, you know, he's obviously a huge asset for them. but, you know, they've done an incredible job at recruiting Dude, is it true So you've been doing this for a long time. And the idea for Bx, I think was pretty simple. It's like, hey, you should be able to access your files wherever you are, not just on one computer. I think you guys started consumer and then is it true? there was sort of this like fork in the road moment where you guys went entnerprise and like, you know, kind of the co foundounders had to debate it out? that is that how that went down Yeah, I mean, it its always sounds way more dramatic, you know, in when we kind of compress it into the end the Brve story, but it was a multi mononth period of of kind of like your classic wandering period that all startups kind of deal with, where you don't know if you're gonna to pivot, you don't know if the business models gonna to work, you don't know if you're gonna to get your next round of funding. like some things are clicking and working, some things aren't And we had started I would say not even as a consumer or enterprise, we kind of started as agnostic to who the user would be. We just said, hey, you know be there should be a secure way to access your files from anywhere. like it was an obvious idea to us. And then what happened was it started growing, but consumers had this kind of know very straightforward fork in the road. Consumers wanted to pay as little as possible And they wanted a certain set of features that you'd have to go and build. Enterprises wanted to pay a lot more, but they would need like a hundred times more features And And as we kind of like thought about like, well, who do you focus on, we did eventually kind of conclude, you know, something really obvious in retrospective. and I can't like unsee it as they look at other people's strategies over time These were just like totally different markets. the enterprise needing to securely manage their most important data as an organization would require just a completely different set of functionality than what a consumer would need to back up their photos and access their music from anywhere. And those were just different markets. And there was different business models. One would pay like five dollars a month, the other would pay maybe five million dollars a year. And like completely different business models, different markets, different teams you'd have to build, different products you'd create So we did eventually run into effectively a fork in the road and after a few months of kind of debating it out and assessing the opportunities peopleople peopleople kind of having you know pretty different views on what to do, we eventually pivoted, you know kind of very forcefully into the enterprise We know almost burned every boat other than a couple that we still wanted a freemium model in the enterprise. We wanted you to be able to sign up as a kind of knowledge worker, but we very firmly wanted to make it an enterprise only business model. And I was actually the most reluctant and the last one to be convinced to pivot. So kind of credit to the other founders and some early employees that I think had more conviction. but once we had once we collectively had conviction then it it was very straightforward. One one thing on that decision, enterprise versus consumer Dropbox, obviously, I think Do they would you say they went the consumer route initially or no because like, you know, Can you look back now say, o, you, one's this billion dollar company? I think Dropbx iss like a six billion dollar company. You guys are just under four? in retrospect Now that you have the benefit of like seeing all play out, was you know was that the right move? or is that overly simplified Hey everyone, really quick. If you're enjoying this episode on CEO stuff. so delegating, having hard conversations with your team, hiring Then I've got something for you. So the team at HubSpot, they actually went and put together a bunch of best practices that Sean and I use in our own companies And they put it together and something that's really easy to read and understand. And so if you want to just save yourself ten years of headache heartache, then you should check it out. I wish we had this a long time ago. It would helped me a lot, but there should be a QR code on your screen that you can scan or a link in the description. so check it out. It's totally free and totally awesome. Well, it was definitely the right move for us and where we were. You know the way we kind of did the math was Google had to own the consumer. You know, we saw the G dririve kind of writing on the wall. They would want to bundle it with Gmail. and most consumers would sort of be satisfied with that. And then iCloud I'd add it on top of that and then OneDrive. And so like the consumer really looked like a total kind of death pit. And dropbox, I would say, performed far better than I would have estimated if from just a pure like economic standpoint, I would have thought that the commoditization would have been much more impactful. So huge kudos to them on their execution and just, you know, obviously building a world class product On that front, what we were very clear on was the only way that we would not go out of business was by being enterpriseed because we just we were too convinced that over enough time that the consumer space would just be too competitive and too commoditized So not only are we fantastically happy with the decision, but I think it was the only outcome that would have produced really any form of success And then I think over the long term, like let's just say we add another ten years to the timeline, I think the only way to build a very large business as an independent company in this category is by being enterprise focused Just because where most dollars gonna go for managing data, securing data, you know kind of caring about how it's governed in a workflow, it's gonna come from businesses. so and there's actually I think relevant lessons as we look at the AI space is I think most dollars in AI will eventually be enterprise dollars There'll be some you know there'll be fantastic outcomes in consumer, no question because there's, you know, some ways to build consumer businesses out of this. But by you by and large, where's intelligence valued it's going to be in the enterprise. So just as where is software valued, it's the enterprise. And that's where most dollars of technology go and other than, you know, three companies that make money on advertising in consumer tech You're fun to talk to because you're only a few years older than Sean and I. We're thirty seven and thirty eight. But I feel like you're so much further. I mean, when we were both like, you know nineteen or twenty one years old, you were on the cover of magazines and you were like the poster child. It was like you and Kevin Rose was like You know, you can make it For me, it was actually the thing I was obsessed with was When we moved to we dropped out, we moved to Silicon Valley and like If you remember like You guys would have been just too young, maybe like seventeen, eighteen, but like it was like Sam Altman was with loop was like top Cer. Yes. that was that was the person to be in the valley. I mean, other than, you know Zuck and it looks exactly the same by the way. I think it's the person to be again. twenty years later. grew up a little bit like watching it. It was really it's been always really fun But I heard some crazy stories about how you got offered all this money at a very young age to sell the company. And I always put myself in that position where I'm like, what would I do? And of course, like The reason you are you and I am me is because I probably would have taken it like yeah, like I wouldn't have had the poise like in the like you have had But how old were you when you first started getting acquisition offers and like, Can you tell some of the stories of what's that like to be such a young person and like facing like like this life changing amount of money U sure, yeah. well, When we first started, we dropped out of college. It was four of us living and working in Berkeley, and we got a call from Yahoo Um And it was the Corp dev team at Yahoo that had basically the team that had more or less just been responsible for buying a flicker So there was this product that was like in the late nineties, early two thousands, it's called Yahoo Briefcase. And it was sort of one of our predecessors. So it was an online storage kind of product But it was like you could store maybe like fifty megabytes of data in Yahoo Briefcase. And for us, you know, we had finally achieved a gigabyte of storage that you could have online And we were like the modern, simpler, faster, easier, you know kind of more up to date version of Yahoo Briefcase. So we got called in by the corp Dev team. and for us We were like, holy, you know, shit, this is biggest moment of our lives, and we were like debating like what acquisition price would would we be willing to take? And I think like Probably the most we could have ever imagined was like five or ten million dollars. And we were like, you know, that's our price We would definitely take five million, you know, What was it like? all right on three? everyverybody' say the number out loud. one, two, three, seven million. I think I think we didn't even have enough we probably felt we would jinx it if we even did that. So it was more like a very serious discussion. So we drove down to Yahoo corporate headquarters in a Nissan minivan that was like totally breaking, you know, falling apart And we did a serious meeting, we presented our whole strategy and, you know, we went through the product And I don't know. I don't remember it's very hazy, but like I dont somewhere on the order probably two weeks later we just got like an email saying, it was really nice meeting, you guys, Thank you for coming by And and we had done all this build upp in our heads of like what What would the number be that we would sell the company for? And again, any of those numbers, we would have been the just ecstatic. about taking. So it's it's one of these things where it's like, you know, we have turned down offers, but we've also been in situations where we totally would have taken, you know That very early offer and just taking it off the table And then, you know, later as we scaled we've had we've had every problem thrown at us. We've had rounds that didn't happen and just like totally busted rounds. We've had to be bridge loaned by our investors twice. So there are definitely, you know, there' definitely, you know, parts of of the journey where we would have, you know, if anybody had shown up with with any offer, we would have we would have accepted it probably And then it's, you know, as these things go, like when people do actually show up for offers, you get you're like your chemicals in your head are totally different. And you're like like, oh my gosh, like we've just got to keep doing this. And so probably the most classic one that we faced was a very kind of serious interaction where where we would have, you, been, I think quite happy about the outcome on any kind of financial measure, but we looked at the situation and we were maybe our midies early to mid twenties at the time, And I think this is now like well documented by a bunch of people, but I think it kind of just happens probably pretty uniformly, which is like you just you like, if you really deeply process it and like in a very intellectual sense And you're like, okay, this much money, like this is super interesting, you know, et cetera. And then you like start to play out like, what am I going to do in two years from now or five years from now or ten years from now We basically just processed like we would probably be doing something just to get back to exactly where we are now. It's unlikely that we're going to work at this new company for more than five years each. so that's not gonna to happen because everybody, every one of our friends that had gotten acquired had already left their acquired company. So like that was probably not gonna happen So then you just look at it youre like, okay, well You're probably trying to do everything you can just to get back to this exact situation. But of course you have more cash. that's obviously positive. But now we're in this situation. We've already defied all the odds of getting here in the first place And all the things that kind of got in our way, like, why don't we just continue to double down on this given that we still believe the market is still one hundred times larger So it became this very kind of calculated decision, which is What's the amount of kind of, you know, how big is this market still ahead of us? We thought very large Do we like our kind of compounding kind of you know approach where we think we're getting better every day every week, every month at our product and our strategy We know that there's going to be a lot of headwinds and a lot of severe competitive pressure that we're going to face. So it's not going to be easy. And then it basically just came down to like, You know, the kind of Bzosian regret min minimization framework of like of like, what thing are we going to regret more or less And we at least we convinced ourselves that we would more regret not continuing and just seeing the next set of cards and keeping on scaling more than we would regret, you know, sort of turning down this offer and having to start over I don't know if it's actually true, L what would we have really regretted more, but that was the decision. It was gut wrenching. Like we did an offsite with the four of us and how old were you guys and how much was the offer We were in our mid twenties, so probably two of us were like twenty twenty five, twenty four, twenty three. And we don't really talk specifically about the offer, but you know all like in the half a billion range G think. And that's Were you guys taking secondary along the way to kind of at least have some Some of that regret minimization, if it all blew up, that like at least we got know a safety net here or no safety net. Not safetyet levels of secondary. So this was a very different time period in the valley. So this was, you know, very early twenty tenens and secondary was not neeither in fashion as much as it is now nor were the amounts of capital the same level. So So I think it was like You know, people could, you know, feel better about the apartment they were renting, as opposed to like were like good on the decision. You were like the Teto orrtes of tech like tech, you know, like, you know, the early UFC guys, they got paid like one thousand dollars to show up at five hundred dollars if they won and like they like made it popular at the docept you're there They're like being honored in the haall of Fame, but they like can't see or talk on the left side of their face anymore All right honestly, if there's like any analogy that works for my entrepreneurial life, it would be that. But we have had to grind through every every worst practice that you could that you could imagine. And I mean, we've lived to tell the talesough You you have a pretty insane investment portfolio too. Let me see Stripe Figma, Robinhood, airtable, Instacart, Plaid That's a pretty baller port. might there might be some hallucination on two of those. Okay. Maybe Chad he lied to me? I think there's some good embedding space clustering of some of those brands. Unfortunately, so I met Dylan Field in the seed round and what a lovely what a lovely character and kid Did you send him a nice to meet you email? like you Yahooed him ah. I think I was I hope I was like three percent better at the follow ups, but I met him and I didn't have the creative imagination for what he was talking about. And I obviously should have because I believe in cloud based software for everything And he was like, designers are going to do real time collaboration on stuff. And I was like, I don't know, man. L we kind of make images fine. So I was like very like I was a huge lot on the on the pitch U And definitely to my detriment, but unfortunately that would be that would be a hallucination. So I didn't I didn't get on figma early enough, but but a few of those, yes has the what's worked out better? The box equity or the Angel portfolio equity. Are we getting close or ' like for example, we have the podcast got bought by Hubspot and Darmesh from Hubspot comes on a bunch He made a huge bet into open AI. and we're like, Dude, you're gonna make more off of that. than you did in this like thirty year Odyssey of Hubspot Hes like,, probably. Fortunately, at least for for other factors bo box is still ahead. But the big thing I should have done is hedged on all of our underlying suppliers U We're like one of the biggest customers of like Seaagate and Western Digital and and so like we could see the stack that you would need for all of this And and it's, I don't know if you guys have watched like the Sandisk stock, but like this is the the just the most insane you know,' just set of memory stocks for these guys. I don't know what you guys are talking about. What Sand disisk is like an all the memory stocks have gone bananas, right? Is it Sandisk like a like a eighties or seventies The sand is up about what three thousand percent maybe in the past two years. I remember sand they made like floppies, right they they b everything and they I mean, we probably wouldn't exist without Sandest. So USB thumb drives were like one of the One of the catalysts for, okay, we should just like move that to the cloud. So if you just bought Sanda Stock like on just because you were really into the USB thumb drives. You would be doing fantastically well right now. Have you seen Any cool So you're talking about like the companies that have gotten big because you've been in the ecosystem where they've been customers? or you've been com customers? What else did you see early on? becausecause they were they were customers I mean, way more than I've invested in, But you know, I think if you just looked at probably even our own tech stack over twenty years and you just bought the stocks of what our tech stack represented, like that portfolio alone would be, you know you would have outwm by every index. Exactly. And that's actually I mean that that's sort of generally a phenomena right now in the valley, which is you can kind of just see like, you can generally see like what What are the engineers using And that tells you quite a bit about the future. Now there could be some misreads in the signal there, but I would say within ninety percent accuracy, it's going to get you like most of the investment advice you need It's a pretty underrated strategy. I call investing in your PNL because you just go look at the expense items. And like I learned this when we were doing a tech company. same thing I was like, oh, paager duty and an elastic search and all these compass sllack. You know, we were one of the first hundred teams on Slack or something And you know, our shitty startup idea didn't work, but like we sure did identify a bunch of really great underlying tools whose ideas did work I own an e commerce business and e commom iss a pretty brutal industry, like pretty low margin type of business But I just funneled all the profits into Shopify and the underlying e commerce stack. and I've done great. know I made more money there than I did in the actual business itself. But like I also wouldn't have understood that ecosystem and like who you couldn't pay me to switch off of had I not like gone through the pain of being there Yeah, it's interesting. the funny thing is like this data is basically out there for every investor. and I do think that the it's probably not kind of leveraged enough. But yeah, I mean, most of the best practices are just well known by engineers very quickly. That's a really challenging thing to think about, Sean. when you're like, well, I have this business, that's like a small business probablyably going to grow quickly But then you think like I could somehow make more investing in this already big business and in your head, you're like, what's it's incredibly matured. Like it can't like grow more. Like everyone has that story now. originally it was Uber, now it's SpaceX. We all could have invested in SpaceX when it was worth eighty billion dollars and you're like this is insane. No way Did you see there was a slide deck recently like I think Cot two put it out or or they did this analysis which was Yeah going from do remember the exact was like one bill go hundred billion to a trillion then ten billion to one hundred billion, I think? Yeah, you're like more likely and you get there faster. It's like, oh You know, I some of these things though are a little bit tough simply because we are in a You know, we're in a pretty kind of feverish environment. so it's always hard to like, how do you normalize for the particular multiples that we're seeing? and is that like a sustainable investment strategy versus right now we're in a moment where that is kind of working when you look at it backwards? But yeah, that was that was definitely counterintuitive when I saw it. Hey, let's take a quick break. You know that feeling when strategy is done, the brief is written, everyveryone's aligned and you realize someone still has to sit down and actually create all the content That someone is usually you,. and it's due tomorrow Well, the Breeze assistant from HubSpot can help It works right inside HubSpot. You can draft a campaign copy, blog posts, emails, all in your brand voice, all using your actual customer data So you don't create just content, you create content that converts. Check out hubspot. com, the Aentic customer platform for growing businesses you have a couple other kind of Prairian You know, you have a good answer to the Peter Thial question of like, what do you believe that few others would agree with you on? I'll read you a couple of them. You know you're basically like bullish on the job market. I think most people think with AI, all our jobs are gone. You're like, no bullish on the job market. Other people think with AI, we're all going to be working less. I think Elon has said this and a few others like, you know, you know, hey here comes a four day weekend every weekend or something. You're like, no, we're going to be working more. And that software companies like these SaS companies are going to do well. So, you know, jobs work hard work and and software companies, Th things that most people, I think feel pretty bearish on You have a different opinion. You want to give us your take on each one of those you know, so much of the idea that jobs go away or that we do less you know, has to come from a place of effectively your short just human creativity and ingenuity and the idea that there's sort of we don't have an insatiable appetite for more and new things. And I've just seen very limited evidence suggest that we don't want to go and discover the next cure for the next, you know, you know, niche problem that people have or the next new form of entertainment people want to experience or the next new consumer product that people want to go and sell or the next you know, new podcast that wants to be created. And so like, if you don't believe that that's going to happen then sure, then you would basically believe we have that abundance sort of comes at the at the expense of jobs and of us, you know, doing things. And so so that that theory has to be that basically, you know, the agents are going to do all of the all of effectively the useful work which then frees us up so much that there's really not much else left. And I just think we will find a way to create a ton more work for ourselves for better or worse. It's not obvious that my view is particularly like utopian. Like I think to some extent, Elon's vision To his credit is actually a far more utopian one than the Doomers. It's actually funny like because they believe in the same underlying technology trend So they basically both believe and if you extrapolate out to AGI then the doomers believe that destroys us and Elons believes that we get this utopia where everything is just done for us And I kind of am more just until proven otherwise I'm just in a third camp, which is like it's like the same progress of maybe both of those two, but with more of a pragmatic outcome, which is like we use that technology to just then create a new set of needs that we have to go in all kind of support and fulfill. It's like a very long list of things that the world is still going to effectively value. still value in person education for children. They're gonna to value childcare. They're gonna value going to a restaurant and having, you know human interaction. They're going to value going to a show. They're going to value talking to a financial advisor that appears to sort of, you have some sense of the market and your set of needs and also has ten other clients that they can kind of like triangulate with or you know a tax professional that you can just like, you know is like accountable for if they get the thing wrong, like their job's on the line versus like an agent that can be just shut off and so thus you're not really sure what accountability they have. So like for all these reasons, like humans just stay in the loop. And so I just think we end up having still a lot more work for everybodyer to do I would say then theour the four day work week thing also kind of supposes something different, which is you basically have to believe that assuming that anybody in in your sector decides not to do a four day work week, then that company, you know with the power of AI will get twenty percent more or twenty five percent more output than you will. And so which market is going to basically have some kind of like collective agreement that says, no, our category, everybody in our industry is only going to work four days a week. So it's just like it requires such a collective sort of like agreement on the part of everybody that you wouldn't then just like have some actor in the system decide, no, I'm just going to like, I will just ship more software. I will sell to more customers than you do, which then gets everything back to five days a week. So that's why it's just very implausible for that outcome to really exist. So check this out. There's this book, Sean, You'll like the name of this title. It's called How to Live on twenty four hours a day And it's a book written in nineteen oh eight. You guys should read it. It's really cool. I just got it And it's all about what happened after the Industrial Revolution. And there's this huge burst of white collar jobs. And there's now millions of Americans as well as Europeans who now are not in a factory anymore and they're doing these white collar jobs. And then there's all these like housewives, this is in the book. and they like they're like, well, now I don't launder our clothing with my hands, I use a machine and I have all this time. And the white collor workers are like, you know, we have extra time. and they're all asking themselves, well, if we have all this extra time now, why do we feel busier than ever? And the whole book is how to make sense of like how to like Bum. makeake your twenty four hour day, how to get everything you can out of it. And it's a little bit of like a productivity book On the busier than everything, I mean, it's every startup founder you've ever met right now absolutely is busier than ever. Like they're way busier than we were when, you know before AI. And the reason for that is because AI it's sort of like this deceptive technology because it like It lets you get started on so many things so easily, but then you still have to complete all the things you started And so you know, you think that like I'm just gonna to deploy all these agents and then I'm gonna like go to the bar or go hang out. But like when the agents are then done, somebody stills to be responsible for like, what do I do next with that information? What do I do next with that piece of software? What do I do next with that video clip that got created? All of that becomes human work again So, so like I think every every single person that is like the most AI pilled right now is just they like we're just drowning. in work because we're like kicking off way more work for ourselves and we can't ever get off that treadmill because of how easy it has become to just create this work.ike I don't know, like an hour before this call, I kicked off two you know kind of processes that now I didn't even need to start, but I started them. And now I'm going to absolutely add another hour to my day because I'm going to go and like do whatever, whatever the agent produced, I'm going to go and follow up with all of that work. And I didn't even have to. But it was so easy to kick it off that now I've created more work for myself So we're just going to do that for everything Here's the one thing you're missing You didn't name it. This is your Jevin's paradox. This is your chance to live on for the next hundred years. We need Levy's paradox' basically the easier it is to do work, the more work you'll do and the more tired you'll be at the end of every day. Yeah, I mean, if we want to run with that, we can Levy's law, dog. Come on We we might as well get some alliteration in there. I make it a law. Are so you're working your ass off right now I am Yeah, it's insane We had Um Repts CEO on recently And he was amazing and he told he told the story and Seaan's like, that's the realest thing anyone has ever said. It was kind of funny. But he told the story about how before they kind of took off, they're kind of in no man's land or even failing for like a handful of years and everyone knows this slack message or this text message where from an employee that says, Hey, can we talk And he was like, I got like one a day. And so everyone was quitting. and like myv nervousism was just crashed Yes.. And we all go through cycles of that, but how has your nervous system like up doing this for twenty years because you've had some crazy shit happen. I think that you had like a hostile takeover attempt You said you've had all like these bridge rounds happen. I mean, you've like been through so so much shit and I would assume, you don't need to be doing this anymore How has your body handled this? Well, I don't know that my body has handled it, but but I'd say my from a brain standpoint, it's very, very stressful. I see a therapist just like to help me like calm myself down from an anxiety standpoint. You know, to Amjads, you know, kind of example, like those are like the worst slack messages. There's like if you just ranked like all of the all the stressful things because you're just like Like, you know, there's like forty implications when when a heat person leaves that you then have to like like instantly kind of cycle through. Probably the reason I keep doing it is because the upside still exceeds the anxiety and the stress the stress and kind of time cost. But what's your upside? It's not money at this point. I would have to imagine. What is it? The upside is the You know, for lack of any better explanation it iss just like the intellectual curiosity and excitement of building something and then having that thing be used in the real world and knowing that like, you know, you get to just move that forward another another step. And then right now I'd say it's even amplified because mostost of the technology that is being built by everybody else ends up being something we can also build on top of. So it's like there's an unending amount of things that we get to go and kind of play with and be a part of. So you know, if we were doing exactly the same thing every single day and it was totally a grind over like I could probably pull that off for maybe five years. I don't know that I'd be able to do like a decade of that, but like I could probably put in five years or just like total grind This is, you know, a grind plus It's just sheer adrenaline Because boom, new model drops. What's the implication? What can it do? You know, how does it touch know Well for us, we love it because it all needs unstructured data and the information that we get to store and manage And so whether it's, you know, the new models, new agent work You know, what's happening in the landscape There's just an unlimited amount of things that you can kind of bite into. And that makes it very exciting. So Have you almost quit? time When was the time you were closest to bailing I would never like personally bail. So the bails that could exist would be like you kind of sell the company orr you like get fired, but you don't fight it. You never thought about resigning as CEO There was a moment like nineteen years ago, where eighteen years ago where, you know, am I like a CEO or am I like a product person? And then do you have to get in a CEO And and then we just solved that by getting a COO. and then that was like, oh, God this is like there's some like God God created a role for people like me where like somebody who like wants to do operational stuff gets to do that And then I get to still do product stuff, but also be CEO. I was like, holy crap, whoever came up with this idea like is brilliant. And so that from that point forward, that sort of solved any kind of like likeike, you know, self doubt I had around like my operational skills. And then the rest has just been like, you know, is the company going to work And then do we need to veer the company in a different direction or not You said you go to therapy sometimes and it's been helpful. What's been an unlock, you know, either maybe a A realization or is there a win that you could share Early on in therapy I kind of we just like identified, I don't even know if it's like a word that everybody uses or only because like I've been going to therapy before like ChatT, so I didn't like research everything that you were ever told, but like choose this term catastroization or catastrophes. And so like maybe that's like a well known term. I have no idea. But the theory being that like I catastrophize things. like you, I get one piece of news and then I instantly extrapolate out to like the worst possible outcomes. L this one person leaves, which means the entire company's out of business U because like, you know, they leave and then they're going to miss this one thing and that's going to stop working and then that's going to break and then and then, you know, doom. And by the way, I think actually like most people, most AI doomers should probably see a therapist because it all it's all just catastrophization. So for me, like what I basically just just started to once I could like kind of like maybe like understand it and and like name it as something You can then feel when it's happening and then you're like, you know what I know this is I've seen this twenty other times or fifty other times in this category and guess what? It doesn't mean the end of the world. The thing doesn't end up blowing up and doesn't break everything. You do recover And so that sort of shortens the cycles of the like anxiety pangs because like previously it would be like kind of like You might be like knocked out for like three days because you're just like, oh my gosh This is the end. This is the end of the whole thing. and then you go through it enough times and you're like, okay, this is like totally survivable. And then sometimes I almost like and now I'm probably like a little bit bipolar on it because like half the time I will just downpl then when something bad happens because because I just I because I don't have like a hundred percent intuition on like when to like what level to toggle it. So then for other people, I'll just be like, this is totally fine. We're going tot fine, thiss not a big deal And it's just because again, I've like, I've pre mitigated the catastrophe. and then other times, you know I then still let it loose a little bit. But that's probably one of the best tools I've been able to have We got to do a thing with Ray Dalio last week and he had us do like these personality tests because that's one of his his kind of shicks I'm like a ninety nine out of a hundred on being neurotic. And it bothers you, you're not a hundred. Yeah I stay up all night, like what questions are? I neurotic But I think it's like it's probably jagged what I'm actually neurotic about. I think there's only like five things. I have some like You know my the most common slack is usually just like this Something's three pixels off, and I was just like going through a website and I just like like it got stuck in my head Today'sodcast is brought you by my friends at Mercury. They make the world's best banking product. I think you know this already. I use Mercury for all of my businesses. I think I have like maybe seven or eight businesses. We use Mercury as our business banking across all of them And now they actually just launched a personal bank account. So I have my personal account there. I moved off of Wells Fargo in Chase. I'm just all in on Mercury. Why I like products that are easy to use I like products that get me and the problems that I have, so like very easy to make a joint account with my wife, veryer easy to spin up virtual cards One click and I get savings yield. It just has all the stuff that I need in one place So if you're looking for the best banking product on the market, it's definitely Mercury. I will fistfight anybody who disagrees with me on that. Go to mercury dot com slash personal and learn more. Mercury is a Fintech, not an FDIC insured bank. Banking services are provided through Choice Financial Group and column N A, members FDIC Are you a believer in these personality tests the way Dahia? We've had actually a bunch of really impressive, successful people come on and alm and very much swear by personality justuff, which I always just thought is horoscope like that's cute. You you want a crystal too? Like I didn' I didn't really believe. And now I'm like I think enough Sart people have have told me this where I'm like, o, I should probably reassess my jokes here. Who else is into them besides Ray We had who was the other was Monish was on. He's, you know, an investor, I think is very, very smart. He was he described how his life changed from a, you know, an assessment that told him like, He the reason you feel the way you feel is because you're playing a game of managing clients and people, but you actually thrive in solo player numbers based competitive games. And you know, he when he switched to investing, he like thrived because that's exactly the type of game that that rewards. D you believe in them? I probably you're more on Seaan's end prior to his Ray interaction. I think it's like fun as like it's usually like always like a good ice brereaker at a corporate opbsite. I've rarely left being able to do anything actionable about it, likeike, yeah, we know you're red. like we know you're going to be aggressive. What are we going to do about that information? We know you're collaborative. Like it's very obvious, you're collaborative Well, some people use itper hiring. They make you do like, there's a whole company called culture app, I think it's called, where you where you ent you enter the job that you need to hire for and it tells you what personality type and then you have your Fencefinders does like a hundred million a year on their their Yeah. so I end up somewhere just in this like I'm to I'm fine with it. I'm also like I don't run the business on it That's how I talk about people who are religious.. You want to have your religion we're good.. Se seems like it helps Um It's a different question kind of in the same vein of kind of know thyself From what I understand, you're pretty big like Biness strategy nerd. I've I've heard that you read books until late at night and you've been do this for a long time. you read books.. You're one of those guys You know, when Ajad came on, he's twice he's referenced like the what's it called like seven powers or five powers or how many powers there are of defensibility only seven All right, seevven. Yeahah. A you if I was to ask people who kind of either founders you advise or people you've worked with, if I was like, Yo what are Earon's kind of like the frameworks he really like pulls a lot or tries to like get people to adopt. what are some of those that you could help Yeah, I've read every book. So I have a pretty good I have a pretty good I believe I have the best set of books at this point. This is something that I'm's like one of the rare things I'm like over confident about Founders only read Seven powers, justust do seven powers. that's like obviously good But if you add to it, you read positioning Have you know this one? Is that love positioning? Nobody reads positioning and then they p up their whole market positioning strategy. So what Seven Powers does is it He's abstracted basically Seven other books in a very compelling way and everybody should read Seven Powers. But if you don't deeply understand innovat's dilemma and this other book innovator solution It's like this great tandem. Yeah, they only do give you the problem. They don't I've never real Yeah I didn't even know there's an innovor solution. I mean he knows how to sell, you know, sequels. so so Innovator strikes back the trilogy. Well everybody, everybody gives up. they never read the solution because they're already like three hundred pages into the dilemma and they're like, o my God. so you want to read It's both the dilema and the solution in tandem, like back to back You want to read some powers, you want to read positioning, you want to read, you know, for it's a little bit more on the fun side, but blue Ocean strategy. It's good kind of like mostly academic plus a little bit infotainment. And then You know, maybe like crossing the chasm or inside the tornado. So if you had the time and you could be like locked in a room and read like six books If you read that, you willll be able to predict one hundred percent of things that happen in technology like without fail. L you'll know every competitive move that people are going to make, you'll know why markets do, the ways the things that they do. You'll understand so much more than just trying to like like wing it and guess what's going to happen next. Do you have like an anti read list where you think these are popular and people read them, but they're You you don't think people should? Yeah Well, there are some kind of your kind of like classics in like leadership books that I have not found myself getting as into, but I do appreciate why people get into them It doesn't like trigger my same sort of visceral uh, you know, kind of, um reaction I think that that they're intending.'re notre you're not a leaderss eat lass or a startarched d type of guy. Make your bed. Yeah. I'm not going I, you know, because I respect the trade. I don't want to I'm not going to call on anything specifically. mayaybe offline. I'll mention a couple. But there are a few where like I'm like fifty pages in and I'm like, I think this is kind of like a little bit too trite. Well let's use this because right now It's easy in hindsight when you read the books because they're like giving you a case study from fifteen years ago, twenty years ago. And you can sort of Malcolm Gladwell, like revisionous history your way into like any conclusion want Those are the fun ones of, you know, the ones that were written in like, you know, ninety three and it was like you know Digital equipment corporation will be the largest company on the planet based on, you know, and it's like it died two years later. right. But right now there's this fog of war with AI and it's's basically game of Thrones. You've got like Elon, the King of the North, he's coming down. He's trying to make it happeny. You' got the anthropics. I guess how do you see this playing out once you think about like seven powers positioning when you think about Some of the frameworks you have, do you have any predictions for us that you can look really smart on or dumb on in next seven years? I'm glad you asked because it does I should based on my confidence on the power of those six books, I should be able to tell you the answer They did not anticipate the AI market. in the record. I think you said, if you read these books, you could you go anything with one hundred percent a hit rate all the time. goo ahead.. Now you just said, I don't know. No idea. who's. Well, partly because there's other factors here that Al Trite didn't write about. So he didn't know whether China would win in open weights models No, I mean, there are literally other factors because we have government like government is such an X factor in this. China is an X factor. So no idea on all of these things. More what these books are good at is like it be, if you're an entrepreneur, it'll tell you if your idea is gonna to be remotely, you know gonna to work or not. So it works better and kind of like early stage like Will this company find a category that it can like wedge into or will the incumbent more likely take the category? Like so I use like innovators dilemma and innvative solution as an example will basically tell you seventy five percent of the time whether you have a shot. as a new startup. Can you can canan you give an example? makeake it makeake it a little more obvious Yeah, I mean, like like like the whole point of Innovators's Dmma was everybody kind of thinks it's like a tech disruption bookcause like, oh this, they got disrupted by a tech or something. that's it's too simplistic. The key is what Innovator's Dmma tells you is if the business model is not something that the incumbent wants to pursue. because the business model is unattractive to the incumbent So if you look at it through that lens, it will very quickly tell you like if you have a new startup Do the incumbent is the incumbent going to find that business model unattractive or not? And if it's unattactive, they won't pursue it. And if it is, then you very much need to assume that that incumbent is going to try and compete with you. Then you have to decide, is that a technology that for whatever reason is like a sustaining technology that the incumbent is going to be classically good at or is it like so hard for them to figure out that they're not And then that tells you things like Google is going to obviously get really good at AI. and they're going to not like they're not going like let the consumer market just disappear because it's actually an attractive business model. as like there's nothing about having an AI answer from the Google experience that would be bad for monetization. And so like everybody that wrote Google off three years ago It was like it's very obvious that like Google wants to go do this one kind of you know, fully Conversely, there's a lot of business models where like over the years, we saw like there were a lot of incumbents that didn't want to move infrastructure to the cloud Because if they moved to the cloud, instead of having like ten thousand customers, they would only have like three or four customers. And that was a totally different business model for certain software providers or certain infrastructure providers. And so you could kind of see who is going to be under pressure as the cloud grew. So I just use these frameworks because they kind of help you predict again, like how is an incument going to respond? Are they going to respond in like a way that is is sort of like closed are they going to respond with the right set of, you know, kind of mechanisms? And that just happens all the time. AI, you know generally is, you know, kind of playing out with not that different of response mechanisms from the incumbents that you would also again, kind of expect. like who's going to go and kind of enter each market, who's going to how are they going to compete, et cetera Are you only interested in that in this business strategy stuff. likeike whenever I read like Blue Ocean strategy, a lot of times I think this is for like a business that is this is like box. This is like a, multi billion dollar company who can swing up and become a tens of billions or hundreds of billions of dollar company over the next decade, not as much like from SMB u lens. Like for example, where I live in New York City, we have this thing called pop up bagels And like it's like kind of an interesting take on a bagel play I think they've actually just raised VC, but like instantly disproving your question. But like, do you ever think about do you ever like nerd out on like, you know we were talking about,, I forget the guy' n nameed Nat Friedman who bought U, you know, the baseball card company. not Turner. N Turner, sorry. Do you ever think of it from that perspective I do I definitely do nerd out, but only if it like crosses my uni I had a friend actually that had an online balloon website and he got he was selling kind of balloons to some wholesale, some consumer And that was really fun because because we could go and brainstorm like, how would you do a consumer or wholesale kind of like party supplies business at scale. And so yeah, I mean, it's like I don't find myself being able to as much, but like it is always fun to get your arms around what we were always brainstorming is like, how do you compete with Party City? Like, okay. So like they've got this one complex thing because they have, you know, physical infrastructure, which means they have a high retail, you know, kind of cost So so it's hard for them to go as full kind of digital. And And so there was a lot of like, you know, classic incumbent dilemmas. I think every every you know, two person startups that are selling physical things in the real world run into the exact same you know, market factors that that a a software business, you know, with VC run into If you were rewind the clock, you're college student. you know, when you started Bx The internet enabled ideas like that If you were free, young, hungry to do something now, what do you think you would want to go build? Just because of my tolerance for pain, I would probably end up somewhere right in in the center of the AI craziness. just becaused have to I'd have to give it a shot. You're probably doing what we're all doing, which is at like nine to ten PM, you're like toying around on Reddit or whatever and like looking at all the nerdy cool stuff. What has catching your eye in the past couple of weeks Brrightbr, nothing has changed sadly in the past couple of weeks, but my stack is not surprising. It's like every tab is one of or every app icon is one of Codex cursor perplexity Claud, figma, like I have everything and I'm like like like perplexity is like if you want like cloud based computer use that's gonna like really go to the website and read each line of text. like I'll click off to Pplexity compomuter If you, you know, if you're just doing basic research, you have, you know, a number of options. If you're building a prototype website, you know I play with you know a few different tools. So nothing surprising on that front What do you think about what's going on with the public markets in terms of software ' that interests us right now. Like I think Sean was he had written down here. What did you say, Sean, do you think this is a generational buy? I said, yeah, like, you know, permission to talk your book. know is software right now in a generational buy spot? or You know, make the case. You can talk about yourself or other companies. Well, I'm very nervous about about any investment advice on this topic simply because you're at the mercy of many other factors of like Is it, you know, chip trade wek, which just means software goes down no matter what? And so like, you know, I say I'll make, you know, separate investment advice because I don't know what the right kind of multiples are at any given moment for this stuff I would just say People probably for the first time ever started tweeting things like system of record, you know, nine months ago or whatever. but like but if you kind of take out any of the temporary zeitgeist nature of any of that, and you just like go back to the core of like literally system of record software, these systems are used as like the authoritative place where your accounting data goes or your you know, your customer data goes, or in our case, your contracts and financial documents go So these are not the things that like are high on the list of I'm going to go and just like try and build a totally alternative different system for. and I want to build it myself And I just because I want to go and save a few hundred thousand dollars or a million dollars. like these systems are in the kind of core guts of these companies So that sort of is why a lot of the software that people say, oh, I vibe coded it in a week that doesn't that doesn't necessarily equate too old. then like like Ford is going to go and replace their ERP system with that vibe coded thing. Like, yes, you were able to stand up a prototype that was functional, but it's just like totally different from like running your enterprise that is held accountable to the SEC and a global supply chain on powering that. So's that's like why a lot of software won't go away in the same in the same way people think But then the upside, which is much more exciting, is what happens when you have agents that are running around and they need to go do all this useful work in your enterprise? Well, the useful work they're going to do is going to require access to data that's inside these systems. And it's going to often require kind of guardrails that those that the agent is sort of participating and ensuring that, you know, the agent just doesn't go off the rails and completely change out, you know, fundamental parts of your EuropeRP data or your CRM data or you kind of a core workflow. So they need deterministic software that they are kind of participating in that have the right walls, the right data access, the right permissions, the right workflow design. That's largely going to come from existing software simply because that's where the workflows have already been built out in most enterprises So there's a lot of actually ways to argue that there's more upside to certain software categories, once agents can participate in those workflows, Because you can just do now way more with that software. So in our case, we actually see an increase in usage because agents are now roaming around accessing all of this data And you want them to access the same data that the user has access to, which means you want something that has like reliable permissions and access controls and whatnot So then it really just becomes a question of like, how do some of these incumbent software companies monetize that agentic upside Um and and I think you're going to see, you know, mostly it's most to be like a consumption oriented model. it'll be on this more more of this headless approach But I think there's going to be a ton of usage of software as a result of the agent, kind of adoption piece Again, hard does then say like, okay, so what should you buy or sell based on that? You have to everybody has to kind of go and do the work. and sort of try and make a judgment call of like what software will get used more because of agents? which is what software gets used less in the future because of that Yeah, we were, you know, we work a lot with Hubspot and we were friends with Darmes and Brian and those guys. kind of insane. The market cap is like two and a half times the revenue and the revenue is growing thirty percent a year or something like that. It's crazy. It's crazy, crazy, crazy. I tend to believe It will go up. I just don't think that like Plumber, Missouri is going to make their own CRM I think the, u for good reason, like we tend to have a, you know, kind of a simplistic u binary approach, but like you look at vibe coding and you say, well, vibe coding must then replace the the software that we already use. and probably the real answer is no, it'll probably just be built on top of the software that we already use And so it'll be the IT person going and customize it their workflow even further, but on a data stack that they trust is reliable and you're going to work you very effectively. It's kind of interesting the signal that you see is so inropics The biggest announcement other than Fable in like the past month is this thing called Claud Tag where you work with a clawed, you know, kind of colleague you know in a shared way. Well, guess what system they launched in Slack Why do they do that? Because the users' already in Slack, and Slack has the right effectively permission boundaries to be able to have a shared collaborative agent that you would work with. And why is CloudTag so powerful? It's because it accesses your software systems that you can give it access to data. So Box is one of those data sources as an example So instead of it's sort of being like, well, Claude wins so Saa loses, you actually can be like, oh, no, actually, this is this intelligence substrate It offers some set of kind of very useful use cases, but then it's probably going to also exist within deterministic software that also has a bunch of use cases that you kind of create values. So I think once you kind of move on from the zero sum nature of like, you know, okay, I'm going to go prompt my way into software every single day to no, I'm going to have some software that is always there that is reliable and deterministic and I'm going to have intelligence kind of get added to that that does more non deterministic things, that's probably like a more logical balance that you'd expect in the future. You're awesome They're smart as shit. Wed love talking to. I mean, you only talk about the things that I know. so if you I can give you lots of topics that I'm not prepared to discuss Enterprise CEO has take on Enterprise. like wow, no Eterprise off. Dude thanks for coming on, man. We've enjoyed following you for a long time. It's been fun getting to hang out with you here for a little bit. That's it. That's the pod. I feel like I can rule the world I know I could be what I want to on the road, let's travel, never looking back Let's take a quick break to talk about a podcast. Beacause if you're listen to this, you like podcasts And what's better than one podcast? Another podcast. And let me tell you, another podcast you should check out. it's called Success Story If you like hearing about different success stories and hearing Q and A sessions with successful business leaders or hearing keynote presentations or just checking out conversations about sales and business and marketing tactics, is a great podcast for you. So check it out wherever you get your podcast