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

2 Jul 2026 · 58 min · 20 chapters

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In short

Aaron Levie (Box co-founder) discusses dropping out of college, building Box into a $3.6B company, choosing enterprise over consumer, early acquisition offers, investing by tracking the tech stack, and how AI affects work and job forecasts.

Guests (backgrounds)

Sam Altman? (not a guest; mentioned). Guests are Sam and Jeff (Box co-founders/execs in the conversation) plus Dylan (Box co-founder; CFO, known for Millionaire Matchmaker). Sam is at Anthropic working on Claude Code. Jeff is involved in farming. Dylan is described as running functions as CFO.

Key claims

Box pivoted from consumer-agnostic file access to enterprise-only after a “fork in the road” because consumer features/pricing conflicted with enterprise needs. Google/Apple/Microsoft made consumer “a death pit,” so enterprise was the only viable path. AI won’t eliminate jobs; humans will stay in the loop and create new work. Therapy helps by naming “catastrophization.”

Notable examples

Yahoo Briefcase predecessor; early Yahoo call with a hoped-for $5–10M outcome; later “half a billion range” offer turned down; investing by buying suppliers/stack (e.g., Sandisk/USB-to-cloud); “Levy’s paradox” (easier work increases work).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Recollections of Millionaire Matchmaker

0:46 to 1:48

Discussion about a memorable episode of Millionaire Matchmaker and its connection to the guest's co-founder.

“Yeah, but so I actually met your co-founder, Dylan, when I was starting my first company in San Francisco.”

Founder's Journey Together

1:49 to 2:10

Exploration of the founding team's background and their long-lasting partnership.

“kind of people split off to different schools.”

Transitioning from College to Business

2:11 to 3:15

The story of how the founders dropped out of college to pursue their business idea.

“which is kind of crazy to think about at this point.”

Fork in the Road: Consumer vs. Enterprise

3:16 to 6:12

In-depth discussion on the pivotal decision to focus on enterprise solutions over consumer offerings.

“like there's like a list of like 10 of these people, You know, Mike's over there, obviously, now with Andre.”

Evaluating the Right Business Move

7:18 to 9:07

Analysis of the decision to pivot towards enterprise and its long-term implications.

“Well, it was definitely the right move for us and where we were.”

The Challenge of Acquisition Offers

9:08 to 11:24

The emotional and strategic complexities of receiving acquisition offers at a young age.

“And that's where most dollars of technology go.”

Facing Acquisition Offers

11:25 to 14:00

Detailed narrative of the experience of dealing with early acquisition offers from major companies.

“We probably felt we would jinx it if we even did that.”

Reflections on Career Decisions

14:00 to 23:25

Explore the decision-making process behind career risks and opportunities.

“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?”

The Future of Work and AI

23:31 to 28:03

Discussion on job markets, AI implications, and human creativity.

“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?”

The Illusion of Free Time in White-Collar Jobs

28:03 to 30:12

Discover how white-collar workers are busier than ever despite advancements in technology.

“And there's this huge burst of white-collar jobs.”
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Navigating Stress and Anxiety in Entrepreneurship

30:12 to 34:19

Learn about the stress of entrepreneurship and strategies for managing it, including therapy.

“We need Levy's paradox as 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.”

Understanding Catastrophization and Its Impacts

34:19 to 36:49

Explore the concept of catastrophization and its effects on decision-making and anxiety.

“And then the rest has just been like, is the company going to work?”

The Value of Personality Tests in Business

38:15 to 42:04

Examine the role of personality tests in personal and professional development.

“Are you a believer in these personality tests the way Dahlia?”

Recommended Reads for Entrepreneurs

42:04 to 44:39

Learn about essential books for predicting technology trends and market movements.

“You want to read, you know, it's a little bit more on the fun side, but Blue Ocean Strategy.”

Predicting AI Market Dynamics

44:40 to 46:31

Explore the challenges of predicting outcomes in the fast-evolving AI landscape.

“So he didn't know whether China would win in open weights models.”

The Innovator's Dilemma Explained

46:32 to 47:29

Understand how the Innovator's Dilemma framework helps assess startup viability against incumbents.

“model as like, there's nothing about having an AI answer from the Google experience that would be bad for monetization.”

Strategies for Competing with Incumbents

47:30 to 49:44

Discover strategies startups can use to compete with established companies in various markets.

“with not that different of response mechanisms from the incumbents that you would also again kind of expect.”

The Future of Software and AI

49:45 to 54:35

Discuss the implications of AI on software systems and enterprise operations.

“If you were free, young, hungry to do something now, what do you think you would want to go build?”

Balancing Software and AI Integration

54:36 to 56:00

Learn about the integration of AI within existing software frameworks for improved enterprise functionality.

“what software will get used more because of agents, which is what software gets used less in the future because of that.”

Exploring the Future of Software and Intelligence

56:00 to 57:20

Discover how the integration of AI and deterministic software is evolving.

“It's because it accesses your software systems that you can give it access to data.”
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Transcript

Automatic transcript. May contain errors.

0:00Sam Parr: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.

0:20By 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 weirder story was they asked for both of us to do it. Somehow I had better judgment, so. 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. ago, 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 and he had told me about being on the show. Wow, really? And by the way, we were like at this bar at like the end of the scavenger 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.

1:27It'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 at this point.

2:13So 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 Code. And he now is a constant thorn in 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.

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? Instagram, I mean, they have, to their credit, they've done obviously an insane job on recruiting. So I think it might literally be a requirement to have been a CTO of like a public company to work there at this point. But like they have like this, like 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.

3:29So he's, you know, he's obviously a huge asset for them. But, you know, they've done an incredible job at recruiting. Dude, is it true, you, 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 compressed it into the brief story.

4:07but 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.

4:37And 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 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 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.

5:08Like the enterprise needing to securely manage their most important data as an organization would require just a completely different set of functionality than what a consumer would need to back up their photos and access their music from anywhere. And those were just different markets. And there was different business models. One would pay like$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.

5:40And 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 eventually pivoted, you know, kind of very forcefully into the enterprise. We almost burned every boat other than a couple that we still wanted a freemium model in the enterprise. We wanted you to be able to sign up as a kind of knowledge worker. But we very firmly wanted to make it an enterprise-only business model. And I was actually the most reluctant and the last one to be convinced to pivot. So kind of credit to the other founders and some early employees that I think had more conviction.

6:17But 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? Can you look back now, say, oh, one's this billion dollar company. I think Dropbox is like a six billion dollar company. You guys are just under four. In retrospect, now that you have the benefit of seeing it all play out, was that the right move or is that overly simplified? Hey, everyone.

6:46Sam Parr: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.

7:16Sam Parr:So check it out. It's totally free and totally awesome. Well, it was definitely the right move for us and where we were. You know, the way we kind of did the math was Google had to own the consumer. You know, we saw the G 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 had added on top of that and then OneDrive. And so like the consumer really looked like a total kind of death pit. And Dropbox, I would say, performed far better than I would have estimated if from just a pure like economic standpoint, I would have thought that the commoditization would have been much more impactful.

7:56So 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 were too convinced that over enough time that the consumer space would just be too competitive and too commoditized. So not only are we fantastically happy with the decision, but I think it was the only outcome that would have produced really any form of success. And then I think over the long term, 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.

8:35just because where are most dollars going to go for managing data, securing data, kind of caring about how it's governed in a workflow, it's going to come from businesses. And there's actually, I think, relevant lessons as we look at the AI space is I think most dollars in AI will eventually be enterprise dollars. There'll be fantastic outcomes in consumer, no question, because there's some ways to build consumer businesses out of this. But 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.

9:14And other than, you know, three companies that make money on advertising in consumer tech.

9:19Sam Parr: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, 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. 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, 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 Luke was like a double collar.

9:53Yes, that was that was the person to be in the Valley. I mean, other than, you know, Zuck. It looks exactly the same, by the way. And he's the person to be again 20 years later.

10:04Sam Parr:Well, we grew up a little bit watching you. 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, the reason you are you and I am me is because I probably would have taken it. Yeah, I wouldn't have had the poise like you have had. But how old were you when you first started getting acquisition offers? And like, can you tell us some of the stories of what's that like to be such a young person and like facing like this life changing amount of money?

10:37Sure. 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. 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 that 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 yahoo briefcase and for us you know we we had finally achieved a gigabyte of storage uh 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 of yahoo briefcase so 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 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'll we would definitely take five million you know was it like all right on three everybody say a number out loud.

11:54One, two, three, 7 million. I think we didn't even have enough. We probably felt we would jinx it if we even did that. So it was more like a very serious discussion. So we drove down to Yahoo corporate headquarters in a Nissan minivan that was like totally breaking, you know, falling apart. And we did a serious meeting. We presented our whole strategy. And, you know, we went through the product. And I don't know, I don't remember. It's very hazy, but like, I 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.

12:31And 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 situations where we totally would have taken, you know, that very early offer. and just taken it off the table. And then later as we scaled, because 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.

13:08So there are definitely parts of the journey where we would have, if anybody had shown up with any offer, we would have accepted it probably. And then as these things go, like when people do actually show up for offers, You're like your chemicals in your head are totally different. And you're like, like, oh, my gosh, like, we 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.

13:46And 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, OK, 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 process like we would probably be doing something just to get back to exactly where we are now. Like, it's unlikely that we're going to work at this new company for more than five years each.

14:19Like, 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 and 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 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 100 times larger.

14:52So it became this very kind of calculated decision, which is, what's the amount of kind of, you know, how big is this market still ahead of us, we thought very large. Do we like our kind of compounding kind of, you know, approach where we think we're getting better every day, every week, every month at our product and our strategy? We know that there's going to be a lot of headwinds and a lot of severe competitive pressure that we're going to face. So it's not going to be easy. And then it basically just came down to like, you know, the kind of Bezosian regret minimization framework of like, what thing are we going to regret more or less?

15:24And 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 what would we have really regretted more? but that was the decision. It was gut-wrenching. We did an off-site with the four of us. How old were you guys

15:48Sam Parr:and how much was the offer? We were in our mid-20s, so probably two of us were 25, 24, 23. And we don't really talk specifically about the offer, but call it in the half a billion range. That's pretty sick. And were you guys taking secondary along the way to kind of at least have some of that regret minimization if it all blew up? that at least we got 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 very early 2010s and secondary was neither in fashion as much as it is now, nor were the amounts of capital the same level.

16:31So I think it was like, people could feel better about the apartment they were renting as opposed to like, we're like good on the decision.

16:39Sam Parr:You were like the Tito Ortiz of tech. You know, the early UFC guys, they got paid like$1 ,000 to show up and$500 if they won. And they made it popular. And then now you're like, you're the Chuck LaVille. Except there, they're being honored in the Hall of Fame, but they can't see or talk out of the left side of their face anymore. Honestly, if there's any analogy that works for my entrepreneurial life, it would be that. So, but we have had to grind through every worst practice that you could imagine. And I mean, we've lived to tell the tale. You have a pretty insane investment portfolio too. Let me see.

17:24Stripe, Figma, Robinhood, Airtable, Instacart, Plaid. Like that's a pretty baller portfolio. There might be some hallucination on two of those. Okay. Maybe Chad, you 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?

17:50Sam Parr:Like you Yahoo'd him? I Yahoo'd him. I think I was, I hope I was like 3 % better at the follow-ups. But I met him and I did not 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, we kind of make images fine. So I was a huge Luddite 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 the angel portfolio equity are we getting close or because like for example we have a 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 gonna make more off of that than you did in this like 30-year odyssey of hubspot he's like yeah probably uh i fortunately at least for um for other other factors box box is still ahead but um the big thing i should have done is hedged on all of our underlying suppliers um we're like one of the biggest customers of like seagate and western digital and uh and so like we could see the stack that you would need for all of this and uh and it's i don't know if you guys have watched like the sandisk uh stock but like this is the the just the most insane um you know it's just set memory stocks for these guys.

19:23Sam Parr:I don't know what you guys are talking about. All the memory stocks have gone bananas, right? Isn't Sandisk like an 80s or 70s software? Sandisk is up about 3 ,000 % maybe in the past two years. I remember Sandisk, they made like floppies, right? They made everything. And we probably wouldn't exist without Sandisk. So USB thumb drives were like one of the catalysts for, okay, we should just move that to the cloud. So if you just bought Sandus stock, 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 the companies that have gotten big because you've been in the ecosystem, or they've been customers, or you've been customers.

20:08Sam Parr:What else did you see early on because they were customers? I mean, way more than I've invested in. But I think if you just looked at probably even our own tech stack over 20 years, and you just bought the stock, of what our tech stack represented, like that portfolio alone would be, you know, you would have, you would have, 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 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.

20:50It's a pretty underrated strategy. I call it investing in your P &L because you just go look at the expense items. And I learned this when we were doing a tech company, same thing. It was like, oh, PagerDuty and Elasticsearch and all these companies, Slack. We were one of the first 100 teams on Slack or something. And our shitty startup idea didn't work, but we sure did identify a bunch of really great underlying tools whose ideas did work. I own an e-commerce business, and e-com's a pretty brutal industry, like pretty low margin type of business. But I just funneled all the profits into Shopify and the underlying e-commerce stack.

21:22And I've done great. I've made more money there than I did in the actual business itself. But I also wouldn't have understood that ecosystem and who you couldn't pay me to switch off of had I not gone through the pain of being there. Yeah, it's interesting. The funny thing is this data is basically out there for every investor. And I do think that it's probably not leveraged enough. But yeah, 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 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 Code 2 put it out.

22:22They did this analysis, which was going from, do you remember the exact, it was like 1 to 10 billion. It's easier to go from 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, 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?

22:57But yeah, that was definitely counterintuitive when I saw it. Hey, let's take a quick break. You know that feeling when strategy is done, the brief is written, 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 a campaign copy, blog posts, emails, all in your brand voice, all using your actual customer data. So you don't create just content. You create content that converts. Check out HubSpot.com, the agentic customer platform for growing businesses.

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23:31You 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, 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.

24:02So, you know, jobs, hard work, 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? 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 insatiable 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, 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.

24:51And 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 that theory has to be that basically, you know, the agents are going to do all of effectively the useful work, which then frees us up so much that there's really not much else left. And I just think we will find a way to create a ton more work for ourselves, for better or worse. It's not obvious that my view is particularly utopian. I think, to some extent, Elon's vision, to his credit, is actually a far more utopian one than the Doomers.

25:31It's actually funny, because they believe in the same underlying technology trend. So they basically both believe and if you extrapolate out to AGI, then the doomers believe that destroys us and 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.

26:12Like 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.

26:48And so that's, you're not really sure what accountability they have. So like for all these reasons, like humans just stay in the loop. And so I just think we end up having still a lot more work for everybody to do. I would say then the four hour, the four day work week thing also kind of supposed something different, which is you basically have to believe that, that assuming that anybody in your, in your sector decides not to do a four day 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 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.

27:26So 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.

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 and the whole book is how to make sense of like how to like um make your 24-hour day how to get everything you can out of it.

28:39Sam Parr: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, 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, you think that like, I'm just going to deploy all these agents and then I'm 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?

29:15What 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. So, so like, I think every, every single person that is like the most AI pilled right now is just, they like, we're just drowning in work because we're like kicking off way more work for ourselves. And we can't ever get off that treadmill because of how easy it has become to just create this work. 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.

29:48And 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 that work. Like, 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 Jevons paradox. This is your chance to live on for the next hundred years. We need Levy's paradox as 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.

30:20Yeah. I mean, if we want to run with that, we can name it. Levy's law, dog.

30:26Sam Parr:Come on. Oh, fumbled that one. We might as well get some alliteration in there. Make it a law. Are you, so you're working your ass off right now? I am. Yeah, it's insane. We had Replitz CEO on recently, and he was amazing. And he told this 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're kind of in no man's land or even failing for like a handful of years. And everyone knows this Slack message or this text message from an employee that says, hey, can we talk? And he was like, I got like one a day.

31:02Sam Parr:And so everyone was quitting and my nervous system was just crashed. Yes. And we all go through cycles of that. But how has your nervous system 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 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 from a brain standpoint, it's very, very stressful. I see a therapist just to help me calm myself down from an anxiety standpoint.

31:43To Amjad's kind of example, those are the worst Slack messages. If you just ranked all of the stressful things, because you're just like, there's like 40 implications when a key person leaves that you then have to like instantly kind of cycle through. Probably the reason I keep doing it is because the upside still exceeds the anxiety and the stress and kind of time costs.

32:09Sam Parr:But what's your upside? It's not money at this point, I would have to imagine. What is it? The upside is the, you know, for lack of any better explanation, it'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 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.

32:46So 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? You know, well, for us, we love it because it all needs unstructured data and the information that we get to store and manage. And so whether it's new models, new agent work, what's happening in the landscape, there's just an unlimited amount of things that you can kind of bite into.

33:29And that makes it very exciting.

33:30Sam Parr:Have you almost quit? When was the time you were closest to bailing? I would never personally bail. So the bails that could exist would be like, you kind of sell the company or you get fired, but you don't fight it. You never thought about resigning as 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 COO. And then I was like, oh, God, this isn't like, there's some 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.

34:12And then I get to still do product stuff, but also be CEO. I was like, holy crap, whoever came up with this idea is brilliant. And so from that point forward, that sort of solved any kind of self-doubt I had around my operational skills. And then the rest has just been like, 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? Either maybe a realization or is there a win that you could share? Early on in therapy, I kind of, we just like identified, I don't even know if it's like a word that everybody uses or only because like I've been going to therapy before like Chachaputee, so I didn't like research everything that you were ever told.

34:56But 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, 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's out of business because like, you know, they leave and they're 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 doomers should probably see a therapist because it's all just catastrophization.

35:30catastrophization. So for me, like what I basically just started to, once I could like, kind of like, maybe like understand it 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. It 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 and then you you go through it enough times and you're like okay this is like totally survivable and then sometimes I I almost like I 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 don't have like 100 % intuition on like when to like what level to toggle it.

36:32So 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 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 been able to have.

36:48Sam 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 kind of schticks. 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 missed? 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, you know, 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 just like, it got stuck in my head.

37:25Today'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.

37:55It 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. Banking services are provided through Choice Financial Group and column NA members FDIC. Are you a believer in these personality tests the way Dahlia? We've had actually a bunch of really impressive, successful people come on and very much swear by the kind of personality stuff, which I had always just thought is horoscope.

38:27Like, that's cute. Do you want a crystal too? Like, 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.

38:39Sam Parr:Who else is into him besides Ray? We had, who was the other person? Monish was on. He's an investor I think is very, very smart. He described how his life changed from an assessment that told him, 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 thrived because that's exactly the type of game that rewards. Yeah, do you believe in him? 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 offsite.

39:24I'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 about that information? We know you're collaborative. Like it's very obvious you're collaborative.

39:36Sam Parr: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 enter the job that you need to hire for, and it tells you what personality type, and then you have your— Dude, StrengthsFinders does like$100 million a year on their— Yeah, so 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. Yeah. Seems like it helps. Different question, kind of in the same vein of kind of know thyself.

40:14From 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. I've heard that you read books. Yeah. 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 many, however many powers there are of defensibility. There's only seven. All right. Seven. Yeah. But 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 like pulls a lot or tries to like get people to adopt?

40:46What 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 like overconfident about. if founders only read Seven Powers, just do Seven Powers. That's like 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 f*** 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.

41:31But if you don't deeply understand Innovator's Dilemma and this other book, Innovator's Solution, it's like this great tandem. Yeah, they only do give you the problem. I've never realized. Yeah, I didn't even know there was an Innovator's Solution. I mean, he knows how to sell sequels. Innovator Strikes Back, the trilogy. Well, 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.

42:06You 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 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 wing it and guess what's going to happen next.

42:43Sam Parr:Do you have an anti-read list where you think these are popular and people read them, but you don't think people should? 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 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 starts with why type of guy? Make your bed. I'm not gonna because I respect the trade I don't want to 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.

43:26Well 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's 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 like Elon, the King of the North, he's coming down, he's trying to make it happen.

44:02You've 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 the 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.

44:25Sam Parr: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. 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 open weights models. No, I mean, there are literally other factors because we have government. Like government is such an X factor in this. China is an X factor. So no idea on all these things. More what these books are good at is like it will 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.

45:06And so it works better in kind of like early stage, like, will this company find a category that it can like wedge into or will the incumbent more likely take the category? Like, so I use like 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. Can you give an example, make it a little more obvious? Yeah. I mean, 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 it's too simplistic. 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.

45:54So 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 as like, there's nothing about having an AI answer from the Google experience that would be bad for monetization.

46:42And 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. 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.

47:14So 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 kind of mechanisms? And that just happens all the time. AI generally is 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? How are they going to compete, etc.?

47:46Sam Parr: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 this is like box this is like a you know multi-billion dollar company who um it can 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 an smb uh 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. Instantly disproving your question.

48:22Sam Parr:Do you ever nerd out on like, you know, we were talking about, I forget the guy's name, Nat Friedman, who bought the baseball card company. Nat Turner. Nat Turner, sorry. Do you ever think of it from that perspective? I do. I definitely do nerd out, but only if it 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.

49:09We, 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 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, 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.

49:48If 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.

50:05Sam Parr: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? BrightBright, nothing 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 as 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.

50:43Like 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.

50:57Sam Parr:What do you think about what's going on with the public markets in terms of software? Because that's something that interests us right now. I think Sean, he had written down here. What did you say, Sean? Do you think this is a generational buy? I said, yeah, permission to talk your book. Is software right now in a generational buy spot? Or 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.

51:36And so I say I'll separate investment advice because I don't know what the right kind of multiples are at any given moment for this stuff. I would just say people probably for the first time ever started tweeting things like system of record, you know, nine months ago or whatever. But if you kind of take out any of the temporary zeitgeist nature of any of that and you just go back to the core of literally system of record software, these systems are used as the authoritative place where your accounting data goes or your customer data goes or in our case, your contracts and financial documents go.

52:11So 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 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 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 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.

52:54So 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 just 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.

53:27So they need deterministic software that they are kind of participating in that have the 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.

54:00And 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 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, you know, kind of adoption piece. But again, hard to then say like, okay, so what should you buy or sell based on that?

54:35You 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.

54:46Sam Parr:Yeah, we were, you know, 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 a plumber in Missouri is going to make their own CRM. Yeah. Yeah. I think for good reason, we tend to have a simplistic binary approach, but you look at Vibe Coding and you say, well, Vibe Coding must then replace 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.

55:29And 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 going to work very effectively. It's kind of interesting, the signal that you see. So Anthropic's biggest announcement other than Fable in the past month is this thing called Claude Tag, where you work with a Claude kind of colleague in a shared way. Well, guess what system they launched in Slack? Why do they do that? Because the user's 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.

56:03And 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 SAS 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. 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.

56:53Dude, you're awesome. You're smart as shit. We'd love talking about it. 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.

57:07Enterprise CEO has take on enterprise. wow no software 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 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 the 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. And let me tell you another podcast you should check out.

57:39It'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.

From the publisher

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 /

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