I dropped out of college and built a $3.6B company from scratch

Get Sam and Shaan's hard-won CEO lessons in one guide: https://clickhubspot.com/ktng Episode 838: Sam Parr ( https://x.com/theSamParr ) and Shaan Puri ( https://x.com/ShaanVP ) talk to Aaron Levie ( https://x.com/levie ) talk about building Box, getting rich slowly, why AI might make us work harder. — Show Notes: (0:00) Story of Box (06:30) Enterprise Over Consumer (10:00) Turning Down Huge Acquisition Offers (17:05) Angel Investing, Missed Bets, and Investing in Your P&L (23:00) Aaron’s Contrarian AI Takes: More Jobs, More Work (30:00) Founder Anxiety, Therapy, and Surviving the CEO Grind (38:45) The Business Strategy Books Aaron Swears By (48:00) AI Tools, Software Stocks, and Why SaaS Isn’t Dead — Links: • Box - https://www.box.com/ — Check Out Sam's Stuff: • Hampton (joinhampton.com): My community for founders. Average member does $25m/year. Many of the guests are members. Get after it...apply: http://joinhampton.com/mfm — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Shaan uses Mercury for banking across all of his companies. you can too: http://mercury.com/ Mercury is a fintech company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N. A., and Evolve Bank & Trust, Members FDIC • I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out: beehiiv.com/mfm-challenge My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Sam Parr?

  Do you know what you're getting into here?

• 0:01Speaker 01

  Nope.

• 0:01Shaan Puri?

  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.

• 0:21Shaan Puri?

  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, season three, episode 11, 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. Do you remember when he did that?

• 0:37Speaker 01

  I do, yes.

• 0:38Shaan Puri?

  Were you in support of that?

• 0:40Speaker 01

  Not exactly. So it was, we took a flyer on that one. They actually, well, the weirder story was they asked for both of us to do it. Somehow I had better judgment, so.

• 0:51Shaan Puri?

  Sam, have you seen this episode?

• 0:53Sam Parr?

  Yeah, but so I actually met your co-founder 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. And Box was a client one time. And so I got to hang out with him.

• 1:08Sam Parr?

  And he had told me about being on the show.

• 1:10Shaan Puri?

  Wow, really?

• 1:11Sam Parr?

  And by the way, we were like at this bar at like the end of the scavenger hunt at like 7:00 PM. And he pulled up his laptop and went to the back table and was like working. And he could enjoy the scavenger hunt.

• 1:22Shaan Puri?

  Well, I think that's one of the crazier things about y'all's story. You've been there for 20 years. It's kind of like four friends, you know, started in college type of deal. And are all four still there now 20 years later?

• 1:35Speaker 01

  So 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, people split off to different schools. And then this idea kind of emerged and we all, we all kind of got back together on it. And then dropped out of college and kind of two, two parts in 2005 and, and 2006. And so we've just been working together for, for, I mean, honestly, like almost 30 years. On different things, which is kind of crazy to to think about it at this point. So right now we have Dylan is CFO. He runs a bunch of functions in the company.

• 2:19Speaker 01

  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 we he now is a constant thorn in my side because every every three days, somebody says the CTO of Box left. Box to go to Anthropic, but he actually he actually retired from Box like six years ago. And but it causes like, you know, sort of unending viral fodder on that one.

• 2:55Sam Parr?

  That's pretty incredible that you can found a company, take it public, and then you go and work at Anthropic. Isn't the Instagram founder another founder?

• 3:04Speaker 01

  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 a 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 10 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.

• 3:37Shaan Puri?

  Dude, is it true you so you've been doing this for a long time? And the idea for Box, 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 enterprise and like, you know, kind of the co-founders had to debate it out? Is that is that how that went down?

• 4:01Speaker 01

  Yeah, I mean, it's always sounds way more dramatic, you know, in when we kind of compress it into the in the brief story, but it was a multi-month 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 going to pivot, you don't know if the business model is going to work, you don't know if you're going 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, it should 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, we had this, we had this kind of, you know, very straightforward fork in the road. Consumers wanted to pay as little as possible, and

• 4:46Speaker 01

  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 100 times more features. 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 retrospect, and I can't like, unsee it as they look at other people's strategies over time. These were just like totally different markets, like the enterprise needing to securely manage their most important data as an organization would require a just a completely different set of functionality than what a consumer would need to back up their photos and and access their music from anywhere. And those were just different markets. And there was different business models. One would pay like $5 a month, the other would pay maybe $5 million a year. And like, completely different

• 5:31Speaker 01

  business models, different markets, different teams you'd have to build, different products you'd create. So we did eventually run into, you know, effectively a fork in the road. And after a few months of kind of debating it out and assessing the opportunities and, you know, people, people 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, you know, almost burned every, every boat, other than a couple that that we, we still wanted a freemium model in the enterprise. We wanted you to be able to sign up as a, as a kind of knowledge worker. But we, 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

• 6:15Speaker 01

  think had more conviction. But once we had, once we collectively had conviction, then it was, it was very straightforward.

• 6:21Shaan Puri?

  One thing on that, that decision, enterprise versus consumer? Dropbox, obviously, I think, would you say they went the consumer route initially? Or no, because like, you know, can you look back now and say, oh, you know, one's a this billion dollar company? I think Dropbox is like a $6 billion company. You guys are just under four. Like, in retrospect, now that you have the benefit of like seeing it all play out, was that the, you know, was that the right move? Or is that overly simplified?

• 6:46Sam Parr?

  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 in something that's really easy to read and understand. And so if you want to just save yourself 10 years of headache and heartache, then you should check it out. I wish we had this a long time ago, would have 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.

• 7:21Speaker 01

  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 Drive 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 than I would have estimated if, 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

• 8:02Speaker 01

  clear on was, was the only way that we would not go out of business was by being enterprise. Because we just were, we had, 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, you know, fantastically happy with with the decision, but I think it was the only outcome that would have, would have produced really any, any form of success. And then I think over the long term, like, let's just say we had another 10 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 like, you know, where are most dollars going to go for managing data, securing data,

• 8:42Speaker 01

  you know, kind of caring about how it's governed in a, you know, in a, in a workflow, it's going to come from businesses. And so, and there's actually, you know, 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, to build consumer businesses out of this. But by, you know, by and large, where is intelligence valued, it's going to be in the enterprise. So just as where is software valued, it's, it's in the enterprise. And that's where, where most dollars of, of technology go. And other than, you know, three companies that make money on advertising in, in consumer tech.

• 9:19Sam Parr?

  You're fun to talk to because you're only a few years older than Sean and I, um, we're 37 and 38. But I feel like you're so much further, I mean, when, when we were both like, you know, 19 or 21 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 could make it.

• 9:37Speaker 01

  For, for me, it was actually the thing I was obsessed with was when we moved, we dropped out, we moved to Silicon Valley. And like, uh, if you remember, like, you guys would have been just too young, maybe like 17, 18, but like, it was like Sam Altman was with looped was like.

• 9:52Shaan Puri?

  With a double collar?

• 9:53Speaker 01

  Yes, that was, that was the person to be in, in, in the valley. I mean, other than, you know, Zuck and.

• 9:58Sam Parr?

  He looks exactly the same, by the way.

• 10:00Shaan Puri?

  And he's the person to be again, 20 years later.

• 10:04Sam Parr?

  Well, we like grew up a little bit, like watching you is 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 at like, yeah, like I wouldn't have had the poise like in the, like you have had. But how old were you when you start, 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?

• 10:34Shaan Puri?

  Facing like this life-changing amount of money?

• 10:37Speaker 01

  Sure, yeah. Well, when we first started, we dropped out of college. It was four of us, uh, 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 Flickr. So there was this product that was like in the late 90s, early 2000s called Yahoo Briefcase. And it was, it was sort of one of our predecessors. So it was an online storage, you know, kind of product. But it was like, you could store maybe like 50 megabytes of data in Yahoo Briefcase. And for us, you know, we had finally achieved a gigabyte of storage that you could have online.

• 11:19Speaker 01

  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 the biggest moment of our lives. And we were like debating like what acquisition price would be, would we be willing to take? And I think like probably the most we could have ever imagined was like five or $10 million. And we were like, you know, that's our price. We would definitely take 5 million, you know.

• 11:51Shaan Puri?

  Was it like, all right, on three, everybody say a number out loud. One, two, three, 7 million.

• 11:56Speaker 01

  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 this 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 don't know, somewhere around the order of probably two weeks later, we just got like an email saying, it was really nice meeting you guys. Thank you for coming by. And we had done all this buildup in our heads of like, what would the number be that we would sell the company for? And again, any of those numbers, we would have been just ecstatic

• 12:42Speaker 01

  about taking. So 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 taken it off the table. And then, you know, later as we scaled, because 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's definitely, you know, parts of the 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 like your, your, your chemicals in your head are totally different. And you're like, like, oh my gosh,

• 13:27Speaker 01

  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 know, 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 mid twenties, early to mid twenties at the time. And I think this is now like well documented by a bunch of people, but, 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 10 years from now? We basically just processed like, we would probably be doing

• 14:11Speaker 01

  something just to get back to exactly where we are now. Like, there's, it's unlikely that we're going to work at this new company for more than five years each. Like, so, so that's not going 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 going to happen. So then you just look at it, you're 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, that's obviously positive. But, but now we're in this situation. We've already defied all the, all The odds of 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 100 times larger. So it became this very kind of calculated decision, which is what's the amount of

• 14:56Speaker 01

  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 Bezosian regret 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, like,

• 15:40Speaker 01

  what would we have really regretted more, but but that was the decision. It was gut wrenching. Like, we did an offsite with the four of us and

• 15:47Speaker 03

  How old were you guys and how much was the offer?

• 15:49Speaker 01

  We were in our mid 20s, so probably two of us were like 20, like 25, 24, 23. And we don't really talk specifically about the offer, but but, you know, call it like in the half a billion range.

• 16:02Shaan Puri?

  Wow. And that's and were you guys taking secondary along the way to kind of at least have have some some of that regret minimization, if it all blew up, that like, at least we we got, you know, a safety net here or no safety net?

• 16:15Speaker 01

  Not safety net levels of secondary. So this was a very different time period in the valley. So this was, you know, very early 2010s and secondary was not neither 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, we're like, good on the decision.

• 16:39Speaker 03

  You were like the Tito Ortiz of tech, like tech, you know, like, you know, the early UFC guys, they got paid like $1,000 to show up and $500 if they won. And like, they like, made it popular.

• 16:51Sam Parr?

  Now you're like

• 16:53Shaan Puri?

  Except there, they're like being honored in the Hall of Fame, but they like can't see or talk out of the left side of their face anymore.

• 17:01Speaker 01

  Uh, I honestly, if there's like any analogy that works for my entrepreneurial life, it would be that. So, uh, but, um, we, we, we have had to grind through every, every worst practice that, that you could, that you could imagine. And, uh, and I mean, we've lived to, to tell the tale. So.

• 17:19Shaan Puri?

  You, you have a pretty insane, uh, investment portfolio too. Let me see, uh, Stripe, Figma, Robinhood, Airtable, Instacart, Plaid. Like that's a, a pretty baller portfolio.

• 17:32Speaker 01

  There might be some hallucination on two of those.

• 17:34Shaan Puri?

  Maybe Chad G T lied to me.

• 17:36Speaker 01

  I, I think, uh, I, I, there's some good embedding space clustering of some of those brands. Um, unfortunately, so I met Dylan Field in the seed round and, um, what a lovely, what a lovely character and kid. Um, uh,

• 17:48Sam Parr?

  Did you send him a nice to meet you email? Like you Yahoo'd him?

• 17:51Speaker 01

  I Yahoo'd him. Uh, I, I, I think I was, I, I hope I was like 3% better, uh, at the follow ups, but, um, I met him, uh, 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. Like we, we, we kind of make images fine. So I was like very like, I was a huge alumni on the, on the pitch. Um, and definitely to my detriment, but unfortunately that would be, that would be a hallucination. So I didn't, I didn't get on, uh, Figma early enough, but, uh, but a few of those, yes.

• 18:28Shaan Puri?

  Has the, what's worked out better? The box equity or the, the angel portfolio equity? Are we getting close or? Cause like, for example, we have a, the podcast got bought by HubSpot and Dharmesh from HubSpot comes on a bunch and he made a huge bet into OpenAI and we were like, dude, you're going to make more off of that than you did in this like 30-year odyssey of HubSpot. And he's like, yeah, probably.

• 18:53Speaker 01

  Unfortunately, at least for other factors, box is still ahead. But the big thing I should have done is hedged on all of our underlying suppliers. We're like one of the biggest customers of like Seagate and Western Digital. And so like we could see the stack that you would need for all of this. And it's, I don't know if you guys have watched like the SanDisk stock, but like this is the just the most insane, you know, just set of runs for these guys.

• 19:23Sam Parr?

  I don't know what you guys are talking about. What is SanDisk is like an old-

• 19:26Shaan Puri?

  All the memory stocks have gone bananas, right?

• 19:28Sam Parr?

  Is it SanDisk like a 80s or 70s software?

• 19:32Speaker 01

  SanDisk is up about, what, 3,000% maybe in the past two years.

• 19:37Sam Parr?

  I remember they made like floppies, right?

• 19:40Speaker 01

  They made everything and they, I mean, we probably wouldn't exist without SanDisk. So USB thumb drives were like one of the catalyst for, okay, we should just like move that to the cloud. So if you just bought SanDisk stock, like on, just because you were really into USB thumb drives, you would be doing fantastically well right now.

• 19:59Sam Parr?

  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 customers. What else did you see early on because they were customers?

• 20:12Speaker 01

  I mean, way more than I've invested in. But, but, you know, I think if you just looked at probably even our own tech stack over 20 years and you just, you just bought the stocks of what our tech stack represented, like that portfolio alone would be, you know, you would have, you would have outperformed every index. Exactly. And that's actually, I mean, that's sort of generally a phenomenon 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, I would say within 90% accuracy, it's, it's going to get you like most of the investment advice you need.

• 20:50Shaan Puri?

  It's a pretty underrated strategy. I call it investing in your P and L because you just go look at the expense items and like I learned this when we were doing a tech company, same thing was like, oh, PagerDuty and Elastic Search and all these companies, Slack, you know, we were one of- First hundred teams on Slack or something. And you know, our shitty startup idea didn't work, but like we, we sure did identify a bunch of really great underlying tools whose ideas did work. I own an e-commerce business and e-comm is a pretty brutal industry, like pretty low margin type of business. But I just funneled all the profits into Shopify and the underlying like e-commerce stack. And I've done great. You know, I've made more money there than I did in the, 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.

• 21:35Speaker 01

  Yeah, it's interesting. The, the funny thing is like this data is basically out there for every investor and, um, and I, I do think that the, it's probably not kind of leveraged enough. But yeah, I mean, most, most of the best practices are just well-known by engineers very quickly.

• 21:50Sam Parr?

  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 that's probably 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, well, it'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 at in SpaceX when it was worth, uh, 80 billion dollars. And you're like, this is insane. No way.

• 22:19Shaan Puri?

  Did you see there was a slide deck recently? Like, uh, I think Co2 put it out or they did this analysis, which was, that going from, oh, do you, do you remember the exact, it was like one to 10 billion.

• 22:29Speaker 01

  Go from a hundred billion to a trillion than 10 billion to a hundred billion, I think.

• 22:32Shaan Puri?

  Yeah. You're like more likely and you get there faster. It's like, oh.

• 22:36Speaker 01

  I, you know, I, I, some of these things though are a little bit tough simply because we are in a, you know, we're, we're in a, 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, and is that like a sustainable investment strategy versus right now? We're, we're in a moment where that is, is kind of working when you look at it backwards. But yeah, that, that was, that was, uh, definitely a counterintuitive when I saw it.

• 23:03Shaan Puri?

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• 23:31Shaan Puri?

  You have a couple other kind of contrarian, you know, you have a good answer to the Peter Thiel 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, here comes the four day weekend, every weekend or something. You're like, no, we're going to be working more. And that software companies, like the SaaS companies are going to do well. So, you know, jobs, work, hard work and, and software companies, three 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?

• 24:12Speaker 01

  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, of effectively your short, just human creativity and ingenuity and, and the idea that there's sort of, we don't have an assailable appetite for more and new things. And I've just seen very limited evidence that suggests that we don't want to go and discover the next cure for the next, you know, you know, niche problem that, that people have, or the next new form of entertainment people want to experience, or the, the next new consumer product that, that people want to go and sell, or the next, you know, new, new podcast that, 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,

• 24:56Speaker 01

  that, 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, you know, 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, like it's not obvious that my, my view is particularly like utopian. Like I think to some extent Elon's, Elon's vision, to his credit, is actually a far more utopian one than the doomers. It's actually funny like they, because they believe in the same underlying technology trend. So they basically both believe in, in if you extrapolate out to AGI, then the

• 25:40Speaker 01

  DUMERS believe that destroys us and Elon believes that 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, all kind of support and fulfill. It's just like a very long list of things that that the world is still going to effectively value. Like, the world is gonna still value in-person education for children. They're gonna value childcare. They're gonna value going to a restaurant and having, you know, human interaction. They're gonna value going to a show.

• 26:23Speaker 01

  They're gonna value like talking to a financial advisor that that appears to sort of, you know, have some sense of the market and your set of needs. And also has 10 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 just can be just shut off. And so that's, you're not really sure what 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 everybody to do. I would say then the four hour, the four day work week thing also kind of supposes something different, which is, you, you basically have to believe that, that assuming that anybody in your, in your sector

• 27:07Speaker 01

  decides not to do a four day work, work week, then that company, you know, with, with the power of AI will get 20% more or 25% more output than you will. And so which market is gonna basically have some kind of like collective agreement that says, no, our category, everybody in our industry is only gonna work four days a week. So it's just like, it requires such a collective sort of like agreement on, on the part of everybody that, that you wouldn't then just like have some actor in the system decide, no, I'm just gonna like, I will just ship more software, I will sell to more customers than you do, which then gets everything back to, to five days a week. So that's why it's like just very implausible for that outcome to, to really exist.

• 27:48Sam Parr?

  So check this out. There's this book, Sean, you'll like the name of this title. It's called How to Live on 24 Hours a Day. And it's a book written in 1908. 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 collar 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?

• 28:31Sam Parr?

  And the whole book is how to make sense of like, how to like, make your 24 hour day, how to get everything you can out of it. And it's a little bit of like a productivity book.

• 28:41Speaker 01

  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 than we were when, you know, before AI. And the reason for that is because AI, it's sort of like this deceptive technology. Cause 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, you think that like, I'm just going to deploy all these agents. And then I'm going to like, go to the bar or go hang out. But like, when the agents are then done, somebody still has 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? Like, all of that becomes human work again.

• 29:22Speaker 01

  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, we can't ever get off that treadmill because of how easy it has, has become to just create this work. Like, 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, like do whatever, whatever the agent produced, I'm going to go and follow up with all of that work. Like, and I didn't even have to, but, 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.

• 30:05Shaan Puri?

  Here's the one thing you're missing. You didn't name it. This is your Jevons paradox. This is your chance to live on for the next hundred years. We need Levy's paradox. It's 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.

• 30:20Speaker 01

  Uh, yeah, I, I mean, if we want to run with that, we can, we can, we can.

• 30:25Sam Parr?

  Levy's Law, dog. Come on.

• 30:28Shaan Puri?

  Fumbled that one.

• 30:29Speaker 01

  We might as well get some alliteration in there.

• 30:31Sam Parr?

  Make it a law. Are you, uh, are you, so you're working your ass off right now?

• 30:35Speaker 01

  I am. Yeah, it's insane. We had, um, um, uh, Replets, um, CEO on recently and, uh, he was amazing. And he told, he told the story. Sean'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, uh, a handful of years. And everyone knows this Slack message or this text message where from, 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 my nervous system, nervous system was just crashed.

• 31:07Shaan Puri?

  Yes.

• 31:08Sam Parr?

  Uh, and I, we all go through cycles of that, but how has your nervous system like kept up doing this for 20 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, uh, body handled this?

• 31:30Speaker 01

  Well, I don't know that my body has handled it, but, um, but I'd say my, from a brain standpoint, um, it's very, very stressful. Uh, I see a therapist, um, just like to help me like calm myself down from an anxiety standpoint, you know, to Amjad's, you know, kind of example, like those are like the worst Slack messages. There's like, if you just ranked all, like all of the, all of the stressful things, because you're just like, like, you know, there's like 40 implications when a, when a key person leaves, um, uh, that you then have to like, like instantly kind of cycle through. The, probably the reason I keep doing it is because the upside still exceeds the, the anxiety and the stress, the stress and, and kind of time cost and.

• 32:09Sam Parr?

  But what's your upside? It's not money at this point, I would have to imagine. What, what is it?

• 32:13Speaker 01

  The upside is, is the. You know, for lack of any better explanation, it's 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 most 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 in 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, it was totally a grind over like, you know, I could probably pull that off for maybe five years.

• 32:55Speaker 01

  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 of just like total grind. But this is, you know, a grind plus just sheer adrenaline. Because boom, new model drops. What's, what's the implication? What can it do? You know, how does it touch? You know, well, for us, we love it because it all needs unstructured data and the, the information that we get to store and manage. And so whether it's, uh, you know, the new models, new agent work, you know, what's happening in the landscape? There's just an unlimited amount of, of things that you can kind of bite into. Uh, and that makes it very exciting. So.

• 33:31Sam Parr?

  Have you almost quit? When was the time, when was the time you were closest to bailing?

• 33:35Speaker 01

  I would, I would never like personally bail. So the bails that could exist would be like, you know, you kind of sell the company or you like get fired, but you don't fight it.

• 33:46Sam Parr?

  You never thought about resigning as CEO?

• 33:48Speaker 01

  There was a moment like 19 years ago where, 18 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 as CEO? And, and then we just solved that by getting a COO. And then I 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, and so that, from that point forward, that sort of solved any kind of like, like, 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?

• 34:33Shaan Puri?

  You said you go to therapy sometimes and it's been helpful. What's been an unlock, you know, either maybe a realization or is there a win that you could share?

• 34:44Speaker 01

  Early on in therapy, I kind of was, we just like identified, I don't even know if there's like a word that everybody uses or only because like, I've been going to therapy before like chat GPT, so I didn't like research everything that you were ever told. But like she used this term catastrophization or catastrophize. And so like, maybe that's like a well-known term. I have no idea. But the theory being that like I catastrophize things. So like, like, you know, I get one piece of news and then I instantly extrapolate out to like the worst possible outcomes. Like this one person leaves, which means the entire company is out of business. Because like, you know, they leave and then they were 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.

• 35:23Speaker 01

  And by the way, I think actually like most people, most AI doomers should probably see a therapist because it's 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 what this is. I've seen this 20 other times or 50 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.

• 36:06Speaker 01

  Because you're just like, oh my gosh, this is the end. This is the end of the whole thing. And, and then you, 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 downplay then when something bad happens because, because I just, I, because I, 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 to be totally fine. This is not a big deal. And it's just because again, I've like, I've, I've sort of 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, I've, I've been able to have.

• 36:49Sam Parr?

  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 shticks. I'm like a 99 out of 100 on being neurotic.

• 36:59Shaan Puri?

  And it bothers you, you're not 100?

• 37:01Sam Parr?

  Yeah, I stand up all night. I'm like, what questions do I miss?

• 37:04Speaker 01

  I have a neurotic enough.

• 37:07Speaker 01

  But I, I think it's like, I'm, it's probably jagged what I'm actually neurotic about. I think there's only like five things. I have some like, like, you know, my, the most common slack is usually just like this, something's three pixels off and I was just like going to our website and I, and I just like, like it got stuck in my head.

• 37:25Shaan Puri?

  Today's podcast is brought to 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 banking account. So I have my personal account there. I moved off of Wells Fargo and 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. Very easy to spin up virtual cards. One click and I get savings yield. It's 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 fist fight anybody who disagrees with me on that. Go to mercury.com slash personal and learn more. Mercury is a fintech, not an FDIC insured bank.

• 38:10Shaan Puri?

  Banking services are provided through Choice Financial Group and Callum N A. Members FDIC.

• 38:15Shaan Puri?

  Are you a believer in these personality tests? The way Dalio, we've had actually a bunch of really impressive, successful people come on and almost, and very much swear by the kind of personality test stuff, which I had always just thought is horoscope. Like that's cute. You want a crystal too? Like, I didn't, I didn't really believe. And now I'm like, I think enough smart people have, have, have told me this where I'm like, okay, I should probably reassess my, my, my jokes here.

• 38:39Sam Parr?

  Who else is into them besides Ray?

• 38:41Shaan Puri?

  We had, uh, who was the other, uh, Monish was on. He, he's, you know, an investor, I think is, is very, very smart. He was, he's, he described how his life changed from a, you know, an assessment that, that told him like, hey, 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.

• 39:10Sam Parr?

  Yeah. Do you, do you believe in him?

• 39:11Speaker 01

  I probably veer more on Sean's end prior to, to his Ray interaction. Um, I think, I think it's like fun as like a, it's usually like always like a good icebreaker at a, at a corporate op site. Um, I've, I've rarely left being able to do anything actionable about it. Like, yeah, we know you're red. Like we, we, we know you're going to be aggressive. What, what are we going to do about that information? Um, we know you're collaborative. Like it's very obvious you're collaborative.

• 39:36Sam Parr?

  Well, some people use it for hiring. They, they make you do like, there's a whole company called Culture Amp, I think it's called, where you, where you enter, you enter the job that you need to hire for, and it tells you what personality type, and then you have your-

• 39:51Shaan Puri?

  Strengths finders does like a hundred million a year on their, their-

• 39:54Speaker 01

  Yeah. So, but like, I, so I, I end up somewhere just in this like, I'm to, I'm fine with it. I'm also like, I, I don't run the business on it.

• 40:02Shaan Puri?

  Like how I talk about people who are religious.

• 40:05Speaker 01

  If you want to have your religion, like, we're good. Yeah.

• 40:07Shaan Puri?

  Seems like it helps. Um, different question, uh, kind of in the, in the same vein of kind of know thyself. From what I understand, you're a pretty big like business strategy nerd. I've seen, I've heard that you read books until late at night and you've, you've been doing this for a long time.

• 40:21Speaker 01

  Heard that you read books.

• 40:24Shaan Puri?

  You're one of those guys. You know, when Amjad came on, he's, he twice, he's referenced like the, what's it called? Like seven powers or five powers, or however, however many powers there are of defensibility.

• 40:32Speaker 01

  There's only seven.

• 40:33Shaan Puri?

  All right. Seven. Yeah. Um, are you, if, 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 Aaron's kind of like the frameworks he really like pulls a lot or tries to like get people to adopt? What, what are some of those that, that you could help teach us?

• 40:48Speaker 01

  Yeah, I've read every book. Um, so I, I have a pretty good, uh, I have a pretty good, um, I, I believe I have the best set of books, uh, at this point. Um, this is something that I'm, it's like one of the rare things I'm like overconfident about. If founders only read.

• 41:07Speaker 01

  Seven Powers, just do Seven Powers, that's like obviously good. But if you add to it, you read Positioning. Have you, you know this one?

• 41:16Shaan Puri?

  Yes, I love Positioning.

• 41:18Speaker 01

  Nobody reads Positioning and then they [bleep] up their whole market positioning strategy. So what Seven Powers does is that 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 Innovator's Dilemma and this other book Innovator's Solution, it's like this great tandem.

• 41:39Sam Parr?

  Yeah, they only do give you the problem. They don't, I've never realized.

• 41:42Speaker 01

  Yeah, I didn't even know there's an Innovator's Solution. I mean, he knows how to sell the, you know, sequels, so.

• 41:49Speaker 01

  Innovator Strikes Back, this trilogy. Well, everybody, everybody gives up. They never read the solution because they're already like 300 pages into the dilemma and they're like, oh my God. So you, you want to read both the dilemma and the solution in tandem, like back to back. You want to read Seven 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, if you had the time and you could be like locked in a, a, a room and read like six books, if you, if you read that, you will be able to predict 100% of things that happen in technology. Like without fail, like you'll know every competitive move that people are going to make.

• 42:34Speaker 01

  You'll know why markets do the ways, the, 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.

• 42:43Sam Parr?

  Do you have like an anti-read list where you think these are popular and people read them, but they're, you don't think people should?

• 42:48Speaker 01

  Yeah, well, there are some kind of like your, your kind of classics in like leadership books that I, I have not found myself getting as into, but I, I do appreciate why people get into them. It doesn't like trigger my same sort of visceral, you know, kind of reaction I think that they're intending.

• 43:08Sam Parr?

  You're not, you're not a Leaders Eat Last or a Start with Dwight type of guy?

• 43:11Speaker 01

  Make your bed. I'm not gonna, you know, because I respect the trade, I don't wanna, I'm not gonna call out anything specifically. Maybe offline, I'll mention a couple, but there are a few where I'm like 50 pages in, and I'm like, I think this is kind of like a little bit too trite.

• 43:26Shaan Puri?

  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 15 years ago, 20 years ago. And you can sort of, Malcolm Gladwell, like revisionist history your way into like any conclusion you want.

• 43:40Speaker 01

  Those are the fun ones of, you know, the ones that were written in like, you know, 93, 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.

• 43:53Shaan Puri?

  But right now, there's this fog of war with AI, and it's, there'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 happy, 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?

• 44:14Speaker 01

  I'm glad you asked, because it does, I should, 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.

• 44:25Speaker 03

  Just for the record, I think you said, if you read these books, you can predict anything with a 100% hit rate all the time.

• 44:31Shaan Puri?

  Go ahead.

• 44:33Speaker 03

  Now, you just said, I don't know.

• 44:35Speaker 01

  No idea who's gonna win.

• 44:39Speaker 01

  Well, partly because there's other factors here that Altrite 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's an X factor, so, no idea on all these things, more what these books are good at is like, it'll be, if you're an entrepreneur, it'll tell you if your idea is gonna be remotely, you know, gonna work or not, and so it works better in kind of like, early stage, like, like, will this company find a category that it can like wedge into, or will the incumbent more likely take the category?

• 45:19Speaker 01

  Like, so I use, like, innovative dilemma and innovative solution as an example, will basically tell you 75% of the time whether you have a shot as a new startup.

• 45:31Shaan Puri?

  Can you make, can you give an example, make it a little more obvious?

• 45:34Speaker 01

  Yeah, I mean, like, like, like, the whole point of Innovator's Dilemma was, everybody kind of thinks it's like a tech disruption book. It's like, oh, this, oh, they got disrupted by a tech or something. But, but that's like, that's, it's too simplistic. The, the key is what Innovator's Dilemma 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, like, does the incumbent, is the, is the incumbent gonna find that business model unattractive or not? And if it's unattractive, they won't pursue it. And if it is, then you very much, you know, need to assume that that incumbent is going to try and compete with you. Then you have to decide, is that a technology that, that for whatever reason,

• 46:16Speaker 01

  is like a sustaining technology that the incumbent is gonna 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 gonna obviously get really good at AI. And they're gonna like, not like, they're not gonna like, let the consumer, you know, 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 was like, it's very obvious that like, 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.

• 46:59Speaker 01

  Because if they moved it to the cloud, instead of having like 10,000 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 gonna be under pressure as the cloud grew. So I just use these frameworks as, because they, they kind of help you predict again, like, how is an incumbent gonna respond? Are they gonna respond in like a way that is, is sort of like closed? Is, is, are they gonna respond with the right set of, you know, kind of mechanisms? Um, uh, and that, that just happens all the time. AI, you know, generally is, is, you know, kind of playing out with, with not that different of response mechanisms, um, uh, from the incumbents that, that you would also again, kind of expect. Like, who's gonna go and, and kind of enter each, each market?

• 47:44Speaker 01

  Who's gonna, how are they gonna compete, et cetera? Are you only interested in that?

• 47:48Sam Parr?

  In this business strategy stuff like whenever I read like Blue Ocean Strategy, a lot of times I think, dude, this is for like a business that is, this is like Box. This is like a, you know, 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 a SMB lens. Like for example, where I live in New York City, we have this thing called pop-up bagels. And like, it's like a kind of an interesting take on a bagel. I think they've actually just raised VC, but like.

• 48:20Speaker 01

  Instantly disproving your question.

• 48:22Sam Parr?

  But like, do you ever think about, do you ever like nerd out on like, you know, we were talking about, um, I forget the guy's name, Nat Friedman, who bought, you know, the baseball card company.

• 48:32Shaan Puri?

  Nat Turner.

• 48:33Sam Parr?

  Nat Turner, sorry. Do you ever think of it from that perspective?

• 48:37Speaker 01

  I do, I definitely do nerd out, but only if it like crosses my universe. So 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. We, 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.

• 49:21Speaker 01

  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 software business, you know, with VC run into.

• 49:41Shaan Puri?

  If you were rewinding the clock, you're, you're a college student, you know, when you started Box, 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?

• 49:53Speaker 01

  Just because of, of my tolerance for pain, I would probably end up somewhere right in the, in the center of the AI craziness. Just because I'd have to, I'd have to give it a shot.

• 50:05Sam Parr?

  You're probably doing what we're all doing, which is at like nine to 10 PM. You're like toying around on Reddit or whatever and like looking at all the nerdy cool stuff. What, what is catching your eye in the last past couple of weeks?

• 50:16Speaker 01

  Um, Brian, nothing has changed sadly in the past couple of weeks, but my stack is not surprising. It's, it's like, uh, like every tab is, is one of, uh, or every app icon is one of Codex, Cursor, Perplexity, Claude, Figma, like I have everything and I'm like, like, like perplexity is like, if you want like cloud-based computer use, that's going to like really go to the website and read each line of text, like I'll click off to perplexity computer. If you, you know, if you're just doing basic research, you have, you know, a number of options. Um, if you're building a prototype website, you know, I play with, uh, you know, a few different tools. So nothing surprising on that front.

• 50:57Sam Parr?

  What do you think about what's going on with the public markets in terms of software? Cause that interests us right now. Like I think Sean was, was, he had written down here. What did you say, Sean? You think this is a generational buy?

• 51:09Shaan Puri?

  I said, yeah, like, you know, permission to talk your book, uh, you know, is, is software right now in a, in a generational buy spot or, you know, uh, make the case. You can talk about it yourself or other companies.

• 51:20Speaker 01

  Well, it's, I'm very nervous about, uh, about any investment advice, uh, on this topic, simply because you're at the mercy of many other factors of like, is it, you know, chip trade week, uh, which just means software goes down no matter what. And so like, you know, I say, I'll make, you know, separate investment advice, cause 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, you know, tweeting things like system of record, you know, nine months ago or whatever, like, and, and, but like, but if you, if you kind of take out any of the, the temporary zeitgeist nature of any of that, and you just like go back to the core of, of like literally system of record software, these systems are used as like the authoritative

• 52:03Speaker 01

  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. Um, and I just want, because I want to go and, you know, save a few hundred thousand dollars or a million dollars. Like these systems are in the In the 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 necessarily equate to, well, then 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

• 52:44Speaker 01

  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 that's like why a lot of software won't go away 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 the agent is sort of participating in and ensuring that the agent doesn't go off the rails and completely change out fundamental parts of your ERP data or your CRM data or kind of a core workflow.

• 53:27Speaker 01

  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.

• 54:08Speaker 01

  So then it really just becomes a question of like, how do some of these incumbent software companies monetize that agentic upside? And I think you're going to see, it's mostly be like a consumption oriented model. It'll be on this 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. But again, hard to 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.

• 54:47Sam Parr?

  Yeah, we were, you know, we work a lot with HubSpot and we are friends with Dharmesh and Brian and those guys. It's kind of insane. The market cap is like two and a half times the revenue and the revenue is growing 30% 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 a plumber in Missouri is going to make their own CRM.

• 55:10Speaker 01

  Yeah, yeah. I think the, for good reason, like we tend to have a, you know, kind of a simplistic binary approach. But like you look at vibe coding and you say, well, vibe coding must then replace the, you know, 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 their workflow even further, but on a data stack that they trust is reliable and you're going to work, you know, very effectively. It's kind of interesting, the signal that you see. So Anthropic's biggest announcement, other than Fable, in like the past month is this thing called Claude Tag, where you work with a Claude, you know, kind of colleague in a shared way.

• 55:51Speaker 01

  Well, guess what system they launched in Slack? Why do they do that? Because the users are 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 what, why is Claude Tag 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 sort of being like, well, Claude wins, so SaaS 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 know, kind of create value.

• 56:30Speaker 01

  So, 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 like have some software that is always there that is reliable and deterministic. And then 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.

• 56:53Sam Parr?

  Dude, you're awesome. You're smart as shit. We'd love to talk to you.

• 56:57Speaker 01

  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.

• 57:07Shaan Puri?

  Enterprise CEO has take on enterprise.

• 57:10Speaker 01

  Like, wow, no, so much about enterprise software.

• 57:13Shaan Puri?

  Well, dude, thanks for coming on, man. We've, uh, we've enjoyed following you for a long time. It's, uh, it's been fun getting to hang out with you here for a little bit. That's it. That's the pod.

• 57:31Shaan Puri?

  All right, let's take a quick break to talk about a podcast because if you're listening 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, this is a great podcast for you. So check it out wherever you get your podcasts.