My First Million - I dropped out of college and built a $3.6B company from scratch

Episode Date: July 2, 2026

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 /

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 no days off.

On a road, let's travel. 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 3, 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? I do, yes. Were you in support of that?

Not exactly. So it was, we took a flyer on that one. They actually, well, the weird 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 co-founder, Dylan. When I was starting my first company in San Francisco, I didn't have a lot of 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. And he had told me about being on the show. Wow, really? By the way, we were like at this bar at like the end of the scavenger hunt at like 7 p.m. And he pulled up his laptop and went to the back table and was like working. And he couldn't enjoy the scavenger hunt. 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? So three of us went to middle school and high school together. And 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 in kind of two parts in 2005 and 2006. And so we've just been working together for, I mean, honestly, like almost 30 years on different things, which is kind of crazy to think about it at this point. So right now we have Dylan is, you know, 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 on Claude, Claude. And he now is a constant thorn on my side because every three days somebody says, the CTO of Box left Box to go to Anthropic. But 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 a public and then you go and work at Anthropic.

Isn't the Instagram founder, another founder who... 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 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. Sam on our end built some of the most important software and infrastructure that we run on to this day. So he's obviously a huge asset for them. But 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 Box, I think, was pretty simple. 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 how that went down? Yeah, I mean, it's always sounds way more dramatic, you know, when we kind of compress it into the, in the brief story, but it

was a multi-month period 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, 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 kind of, you 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. go and build. Enterprises wanted to pay a lot more, but they would need like a hundred 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 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. Like 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 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 $5 a month.

The other would pay maybe $5 million 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, 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 kind of having pretty different views on what to do, we have a few months. eventually pivoted, you know, kind of very forcefully into the enterprise. We, you know, almost burned every, every boat other than a couple 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 think, had more conviction. But once we had, Once we collectively had conviction, then it was very straightforward. One thing on 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, say, oh, you know, one's 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 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 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.

It 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. Well, it was definitely the right move for us and where we were. The way we kind of did the math was Google had to own the consumer. We saw the GDrive 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 added on top of that and then OneDrive. And so 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 enterprise. Because we just were, we were too convinced that over enough time that the consumer space would just, be too competitive and too commoditize. So not only are we, you know, 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 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 most dollars going to go for managing data, securing data, you know, kind of caring about how it's governed 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 build consumer businesses out of this.

But by, you know, by and large, where's intelligence valued it's going to be in the enterprise? So just as where is software valued, it's in the enterprise. And that's where most dollars of technology go. And other than 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 37 and 38. But I feel like you're so much further. I mean, when we were both like 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. 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 17, 18. But like, it was like Sam Altman was with looped was like, the double collar. Yes, 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.

And it's the person to be again 20 years later. Well, we like grew up a little bit. watching you. It's 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've 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. Uh, 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, 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 the in in Yahoo briefcase and for us you know we we had

finally achieved a gigabyte of storage that you could have on online and we were like the modern simpler faster easier you know kind of more up-to-date version of Yahoo briefcase we got called in by 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, we, 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. Was it like, all right, on three, everybody say a number out loud. One, two, three, seven million.

I think, I think we, we didn't even have enough. We probably felt we would, 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 on 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 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 a situation 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, because we've had every problem thrown in. at us. We've had rounds that didn't happen and just like totally busted rounds. We've had to be bridged 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 has 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, you're like, your,

your chemicals in your head are totally different. And you're like, oh my gosh, like, we're just got to keep doing this. And so probably the most classic one that we faced was a very kind of serious interaction 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-20s, early to mid-20s 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

like what am i going to do in two years for now or five years from now or 10 years from now we basically just processed like we would probably be doing 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 obviously positive. But now we're in this situation. We've already defied all the,

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 a hundred times larger? So it became this very kind of. 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 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 unscaling 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, what would we have really regretted more? But that was the decision. It was gut-wrenching. Like, we did an off-site with the four of us. How old were you guys? And how much was the offer? We were in our mid-20, so probably two of us were like 25, 24, 23.

And we don't really talk specifically about the offer, but, you know, call like in the half a billion range. Wow. And that's, and 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, you know,

a safety net here or no safety net? 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, were, like, good on the decision. 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.

And then now you're like, you're there 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. 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 tale. as though. You have a pretty insane investment portfolio, too. Let me see. Stripe, Figma, Robin Hood, Airt, Instacart, Plaid.

Like, that's a pretty baller portfolio. There might be some hallucination on two of those. Okay. Maybe Chad, you see 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 character and kid. Did you send him a nice to meet you email?

Like you yahooed him? I, I think I was, I hope it was like 3% 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, like, we kind of make images fine. So I was a huge lot on the pitch, and definitely to my detriment.

But unfortunately, that would be a hallucination. So I didn't get on Figma early enough, 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? Because, like, for example, we have the podcast got bought by HubSpot

and Darmesh from Hubstock comes on a bunch. and he made a huge bet into Open AI, and we're 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. Fortunately, at least for other factors, boxes 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, it's just set of runs for these guys. I don't know what you guys are talking about. Sandisk is like an old memory stocks have gone bananas, right? Is it Sandisk like a, like a 80s or 70s? Sandisk is up about, what, 3,000 percent maybe in the past the two years. I remember Sandus, they made like floppies, right? They, they, they, they, they, I, they, I, They made everything. And they, I mean, we probably wouldn't exist without Sandus.

So USB thumb drives were like one of the, one of the catalyst for, okay, we should just, like, move that to the cloud. So if you just bought Sandus stock, like, on, just because you were really into 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 customers, what else did you see early on? because 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 20 years and 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, you would have. You're a Warren Buffett. 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 are the engineers

is 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 90% accuracy, it's going to get you like most of the investment advice you need. It's a pretty underrated strategy. I call it investing in your P&L because you just go look at the expense items. And like, I learned this when we were doing a tech company. Same thing. It was like, oh, pageer duty and Elasticsearch and all these compass Slack. You know, we were one of the first 100 teams on Slack or something. And, you know, our shitty startup idea it 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-coms are 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. 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, 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. 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 in SpaceX when it was worth $80 billion. And you're like, this is insane. No way. Did you see there was a slide deck recently? Like I think Kutu put it out or they did this analysis, which was that going from, oh, do you remember the exact was like one to 10 billion? It's easier to go for 100 billion to a trillion than 10 billion to 100 billion, I think. Yeah, you're like more likely and you get there faster. It's like, oh. You know, I, you know,

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 definitely a counterintuitive when I thought. Hey, let's take a quick break. You know that feeling when strategy is done, the brief is.

written, everyone'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 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 agenic customer platform for growing businesses. You have a couple other kind of contrarian. You know, you have a good answer to the Peter teal 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, 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, hard work and software. 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? 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 a short, just human creativity and ingenuity and the idea that there's sort of, we don't have an satiable 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 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 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 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 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 Dumers. It's actually funny because they believe in the same underlying technology trend. So they basically both believe in if you extrapolate out to AGI, then the DOOMers believe that destroys us. And Elon 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 just like a very long list of things that the world is still going to effectively value. Like the world is going to still value in-person education for children. They're going to value child care. They're going to 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 like talking to a, financial advisor 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 jobs on the line versus like an agent that 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-day work week thing also kind of supposed something different, which is you basically have to believe that assuming that anybody in your, in your sector decides not to do a four-day work week, then that company, you know, with the power of AI,

will get 20% more or 25% 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 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'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? 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.

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 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 are you next with that video clip that got created?

Like all of that becomes human work again. So, like, I think every, every single person that is like the most AI pilled right now is just, 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 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 do whatever the agent produced. I'm going to go and follow up with all 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. 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. Yeah. I mean, if we want to wrong with that, we can, we can, we can leave his law, dog. Come on. Fumbled that one. We might as well get some alliteration in there. We're making a law. Are you, are you, so you're working your ass off right now?

I am. Yeah, it's insane. We had, um, uh, uh, Replitt's, um, CEO on recently. And, uh, he was amazing. And he told, he told the story. And 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 were kind of a no man's, like. 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 my nervous system, nervous system was just crashed. Yes.

And 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 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 I'd say my, from a brain standpoint, it's very, very stressful. I see a therapist

just, like, to help me, like, call 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, 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 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 and kind of time costs. And what's your upside? It's not money at this point, I would have to imagine. What is it? The upside is, is the, you know, for lack of any better explanation, is 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 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 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, you know, 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 of just, like, total grind. But this is, you know, a grind plus just sheer

adrenaline, because boom, new model drops. What's the implication? What can it do? You know, how does it touch? 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, 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. Have you almost quit? 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 know, you kind of sell the company or you, like, get fired, but you don't fight it. You never thought about resigning a CEO. 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 a CEO? And then we just solved that by getting a C-O-O. And then I was like, oh, God, this is, like, there's somebody, like God and 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, 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? 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? 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 chbtee so I didn't

research everything that you were ever told but like she uses this term catastrophization or catastrophies 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 companies 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, you know, doom. And by the way, I think actually like most people, most AI Dumer's should probably see a therapist because it's all just catastrophization. So for me, like what I basically 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. 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 downplay then when something bad happens because I just 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, I've, 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 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 kind of schicks. I'm like a 99 out of 100 on being neurotic. And it bothers you, you're not 100? Yeah, I stayed up all night. I'm like, what questions are

I'm a neurotic enough. 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, 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 our website and I, and I just like, like, it got stuck in my head. 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 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.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 Dali, we've had actually a bunch of

really impressive, successful people come on and very much swear by the kind of personality that stuff, which I had always just thought is horoscope, like, that's cute. Do you want a crystal too? Like, you know, I didn't really believe. And now I'm like, I think enough smart people have told me this where I'm like,

okay, I should probably reassess my jokes here. Who else is into him besides Ray? We had, who was the other person? Monish was on. He's, you know, an investor I think is very, very smart. He was, he described how his life changed from, you know, an assessment 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 when he switched to investing, he, like, thrived because that's exactly the type of game that rewards. Yeah, do you believe in them? I probably veer more on Sean's end prior to his Ray interaction.

I think it's, like, fun as like a, it's usually like always like a good icebreaker at a corporate off site. I've rarely left being able to do anything actionable about it. Like, yeah, we know you're red. Like, we know you're going to be aggressive. What are we going to do?

do about that information. We know you're collaborative. Like, it's very obvious you're collaborative. Well, some people use it for hiring. 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... Yeah. Dude, Strengths Finders does like 100 million a year on their... Yeah. So, like, I end up somewhere just in this, like, I'm fine with it. I'm also, like, I don't run the business on it. Like how I talk about people who are religious. If you want to have your religion, we're good.

Seems like it helps. Different question, kind of in the same vein of kind of know thyself. From what I understand, you're a pretty big, like, business strategy nerd. I've heard that you read books until late at night, and you've been do this for a long time. I heard that you read books. You're one of those guys. You know, when Amjad came on, he's twice he's referenced like the, what's it called, like seven powers or five powers or however many powers there are of defensibility?

There's only seven. All right, seven, yeah. Are 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 Aaron's kind of like, the frameworks he really pulls a lot or tries to like get people to adopt? What are some of those that you could help teach us? 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, it's like one of the rare things. I'm overconfident about. If founders only read seven powers, just do seven powers. That's obviously good. But if you add to it,

you read positioning. You know this one? Yes, I love positioning. Nobody reads positioning, and then they fuck 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 solution, it's like this great tandem. Yeah, they only do give you the problem. They don't, I've never realized. Yeah, I didn't even know there's an innovator solution. I mean, he knows how to sell the, you know, sequels. So, so.

Innovator strikes back. This is the 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 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, 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 will be able to predict 100% of things that happen in technology, like without fail. You'll know every competitive move

that people are going to make. You'll know why markets do the things that they do. You'll understand so much more than just trying to 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 you don't think people should? Yeah, well, there are some kind of like your kind of classics in like leadership books that I have not found myself getting as into. But I do appreciate why people will get into them. it doesn't like trigger my same sort of visceral, you know, kind of reaction I think that they're intending.

You're not a leaders eat last or a start-to-wise type of guy. Make your bed? I'm not going to, you know, because I respect the trade, I don't want to, I'm not going to call out anything specifically. Maybe offline I'll mention a couple. But there are a few where I'm like, I'm like 50 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 15 years ago, 20 years ago. And you can sort of, Malcolm Gladwell, like, revisionist history your way into like any conclusion you want. 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 is like, it died two years later. Right. But right now there's this fog of war with AI. And it's basically Game of Thrones.

You've got Elon, the king of the north, he's coming down, he's trying to make it happy. You've got the anthropics. I guess how do you see this playing out? Once you think about 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. Just in the record, I think you said if you read these books, you can predict. You'll know everything.

Anything with a 100% a hit rate all the time. Go ahead. Now you just said, I don't know. No idea who's going to win. 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 Openweight's 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 it. things. More what these books are good at is like it will it'll be if you're an entrepreneur, it'll tell you if your idea is going to be remotely, you know, going to 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. So I use like innovators Delana and Innovative solution as an example. will basically tell you 75% of the time

whether you have a shot as a new startup. Can you me give an example, make it a little more obvious? Yeah, I mean, 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, they got disrupted by a tech or something. But that's like, it's too simplistic. The key is what Innovators' 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 incumbent going to 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, 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 like not like, they're not going to like let the consumer, you know, market just disappear because it's actually an attractive business model. 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 Google wants to go do this one kind of, you know, fully.

Conversely, there's a lot of business models where, like over the year, 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 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 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 incumbent going to respond? Are they going to respond in, like, a way that 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? Like, whenever I read, like, Blue Ocean Strategy, a lot of times I think, dude, this is for, like a business that is a, 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 dollars company over the next decade, not as much like from an 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 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 it? Do you ever like nerd out on like, you know, we were talking about, I forget the guys named Nat Friedman who bought, you know, the baseball card company. Nat Turner. Matt 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 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 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 so there was a lot of like, you know, classic incumbent dilemmas. I think 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 a software business, you know, with VC run into. If you were rewind the clock, 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. Just because of my tolerance for pain, I would probably end up somewhere

right in the center of the AI craziness, just because I'd have to give it a shot. You're probably doing what we're all doing, which is at like 9 to 10 p.m. you're like toying around on Reddit or whatever and like looking at all the nerdy cool stuff. What is catching your eye in the past couple weeks? Bright, I think has changed sadly in the past couple 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, Claude, Figma. Like, I have everything. And I'm 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. 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? Because that's interesting 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 to your book. You know, is software right now in a generational buy spot or, you know, make the case? You can talk about it yourself or other companies. Well, I'm very nervous about any investment advice on this topic, simply because you're at the mercy of many other factors of like, is it chip trade week, 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, you know, tweeting things like system of record, you know, nine months ago or whatever, like, and, but like, 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, 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 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 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 necessarily equate too old than 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 you know enterprise that 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 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 ensuring that, you know, the agent just doesn't go off the rails and completely change out, you know, fundamental parts of your ERP data or your CRM data or, you know, kind of a core workflow. So they need deterministic software that they are kind of participating in that have the right, you know, 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. And I think you're going to see, you know, mostly, it's mostly to be like a consumption-oriented model. It'll be on this more this headless approach. But I think there's going to be a ton of usage of software as a result

of the agent, you know, kind of adoption piece. But again, hard does that and 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 work a lot with HubSpot, and we are friends with Darmash 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 Missouri is going to make their own CRM.

Yeah, yeah. I think 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 So Anthropics, 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. Well, guess what system they launched it 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 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's sort of being like, well, Claude wins, so SaaS loses, you actually can be like, oh, no, actually this is this intelligent 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 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 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. Dude, you're awesome. You're smart as shit. We'd love talking about.

I mean, you only talked 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. Exactly. Like, wow, no, so much on enterprise software. Well, 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. I put my all in it like no days off. On a road, let's travel, never looking back. 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, another podcast you should check out. It's called Success Story. If you like hearing about different success stories and hearing Q&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 podcast.