In short
Aaron Levie argues that AI “agent” tools create a short, high-leverage window (about the next 3 years) to build new companies. He claims AI will augment work rather than simply replace it, but humans will still be needed for accountability, guardrails, and “last-mile” decisions. He also addresses layoffs, saying some are AI-related (productivity gains) but many are due to prior overhiring.
Guest backgrounds
Aaron Levie is founder of Box, a $4B company; he says 64% of the Fortune 500 uses Box.
Key claims
AI code generation won’t eliminate software engineering because production, security, integration, and maintenance still require expertise and human accountability. Agents will shift roles toward “agent management” and escalation. Enterprises will need new services/integration work to deploy agents safely. Market windows recur every 10–30 years.
Notable examples
“Death of the software engineer” debate; Financial Times example of lawyers inundated by AI-driven client questions; Harvey for legal; Eli Lilly “lab software automation engineer” role; healthcare radiology analogy (AI may increase imaging demand, not eliminate radiologists).
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Opportunity in AI
1:30 to 3:30
Aaron discusses the significant opportunities for building AI companies now.
“The mainframe, the personal computer, the internet, the cloud slash mobile.”
Skills and Mindset for Success
3:30 to 6:30
Explore how ambition and skills can overcome historical barriers in tech.
“I'm thinking about something where normally I wouldn't be like draw on paper what I'm coming up with.”
The Role of Humans in AI
6:30 to 8:10
Aaron explains the continued necessity of human involvement in AI processes.
“It sort of paid the salaries of these three people.”
Market Changes and Job Dynamics
8:10 to 11:10
Understanding how AI impacts job markets and the creation of new roles.
“It has to go into three meetings and coordinate with some other set of people.”
The Future of Automation
11:10 to 13:10
Discussing the potential for automation to create new workflows and businesses.
“But then you can do a cloud project with instructions.”
Accountability in AI Workflows
14:01 to 16:10
Learn about the importance of accountability in AI-driven workflows and the challenges faced by enterprises.
“And so somebody has to take on accountability for the output of that agent in your workflow at some point.”
AI's Impact on Layoffs
17:09 to 18:51
Explore the relationship between AI and company layoffs, and the factors contributing to this trend.
“But we still hear all the news about layoffs happening due to AI.”
Skills and Hiring in the AI Era
18:52 to 21:21
Understand the evolving skills required for candidates in the AI landscape and the importance of domain expertise.
“What are you looking for in a candidate?”
AI Tools for Productivity
21:22 to 22:38
Learn about top AI tools for productivity and examples of how they can enhance workflows.
“The kind of things that I'll never do again is like I'll never do like market research in a traditional way.”
Automation in Business Processes
22:39 to 24:22
Discuss the potential for automation in business processes and the importance of human oversight.
“Uh, like, did you, cause I hear some people like upload personal constitution, like their principles of work.”
Show all 21 chapters
The Future of AI in Company Operations
24:23 to 27:52
Examine the role of AI in company operations and the balance between automation and human decision-making.
“They're like, I share all my business decisions with my AI.”
Understanding the Three-Year Building Window
28:00 to 29:10
Explore why the next three years are critical for technology innovation.
“Well, I mean, it could be three and a half years.”
Identifying Market Gaps and Opportunities
29:10 to 31:40
Learn about existing gaps in the market and potential startup opportunities in AI.
“In our era, it was Salesforce and Workday and sort of enterprise software companies like Box that sort of were able to capture that moment.”
Strategies for Finding and Validating Startup Ideas
31:40 to 34:24
Discover frameworks for identifying and testing startup ideas in a fast-changing market.
“With a whole new layer of active creatures in the market, which are agents.”
Navigating AI Integration Challenges in Business
34:30 to 37:05
Understand the challenges of integrating AI into existing workflows and businesses.
“Maybe the only thing is like Mark Cuban has had this riff and I fully agree with it.”
The Evolving Role of AI in Various Industries
37:05 to 42:00
Examine how AI impacts different sectors and the new opportunities it creates.
“Should I have some escalation mechanism that like pings me on my cell if like I need to look at something?”
The Best Time to Start a Company
42:00 to 43:15
Exploring whether now is the ideal time to launch a startup and the importance of having a great idea.
“Like when I did, uh, startups before box and I was a solo founder, like, man, I, you had to do 10 things and you're like, you're so tired.”
Excitement and Stress in Entrepreneurship
43:15 to 45:08
Discussing the blend of excitement and stress in the current entrepreneurial landscape.
“competition because basically by lowering the barrier of getting ideas out in the market, what do you get?”
Impact of AI on Job Dynamics
45:08 to 47:59
Analyzing how AI will change job roles and customer support in the next five years.
“I think there's going to be work that gets compressed.”
The Future of College Education
47:59 to 51:47
Debating whether traditional college education will change in the wake of AI advancements.
“kind of contextualized answer because they could decide how much risk I wanted to take on or not take on.”
Advice for Today's Entrepreneurs
51:47 to 53:37
Offering practical advice for new entrepreneurs on leveraging technology and market trends.
“So there's some things that need to change about college, but does the very concept change?”
Transcript
Automatic transcript. May contain errors.0:00Study and play. Come together on a Windows 11 PC. And for a limited time, college students get the best of both worlds. Get the Unreal College Deal. Everything you need to study and play with select Windows 11 PCs. Eligible students get a year of Microsoft 365 Premium and a year of Xbox Game Pass Ultimate with a custom color Xbox wireless controller. Learn more at windows.com slash student offer. While supplies last, ends June 30th. Terms at aka.ms slash college PC. Today we helped a Latte for Sam coffee shop get an insurance quote simply and easily and made sure a floral delivery van was able to make someone's day.
0:41We're the Hartford, with decades of experience insuring millions of unique small businesses. When it comes to your small business insurance Thank you. one size absolutely does not fit all. Get a quote or find an agent today at thehartford.com slash smallbusiness. The more I play with AI agents, I do realize that I need a person at the beginning of the process and the end of the process, so I still end up having more people. Some of it will be different roles, but I'm very optimistic that we're going to use this technology to grow more and do more, as opposed to just replace. This is Aaron Levy, founder of Box.
1:17Welcome! Four billion dollar company. 64 % of the Fortune 500 uses his platform. He says we have three years to build the next generation of AI companies. These market windows happen every 10, 20, 30 years in technology. The mainframe, the personal computer, the internet, the cloud slash mobile. If you were starting today, what would you do to find the right idea, to test it and to make first money? My first thing would be... Five days ago, you know, said this. We're at a unique moment in history where anyone with high level of ambition and core skills in any area can overcome a lot of historical experience requirements for your role.
1:55Can you talk more about that? So it's this interesting dynamic where a younger group, not necessarily in age, but maybe in skill or time in that domain. So an earlier group in that domain can have as much leverage and in many cases even more because of their mindset differences than somebody that is like super experienced in a field. Now, interestingly, the advice can go in all directions because you can, you know, you could have somebody maybe too early in that field and then use AI in the wrong way and get the wrong outcomes. You could have somebody extremely experienced that decides to adopt the technology, and then they have a total superpower because they understand all of the contours of whatever they're working on, whether it's writing code or doing healthcare or doing biotech.
2:39And they will be actually even more capable of leveraging these tools if they have the kind of right mindset wiring to be able to leverage them. leverage them so i think the core idea is that we're just in this amazing moment where if you're super ambitious you want to go deep into technology ideally you're technical or or becoming technical so you can kind of really know your way around these tools you can make up for again lots and lots of years of of skills that that you would have otherwise had to go and develop and i think that's an incredible thing for democratizing um you know knowledge and skill sets and expertise uh i often am and building things or designing things or coming up with things that i have you know, in any other in any other version of the world, I would never been able to go do.
3:19But now I know just enough to be dangerous in those areas. And it helps me prototype. It helps me generate new ideas. It helps me kind of work with call ins faster because I can kind of like highlight the way I'm thinking about something where normally I wouldn't be like draw on paper what I'm coming up with. But that I just say, OK, this is the rendering that we're looking to do. And so, again, I think that's an incredible technology that's available to everybody for those that want to adopt it and lean in right now. What would you say to someone who's watching this, but they've also heard a lot of news about layoffs, about college graduates not getting enough jobs because they're being replaced by AI?
3:56What would you say to those people? Yeah, I think there is. I think we're at a moment right now where, and these happen in history every couple decades or every 50 or 100 years where there's a major technology disruption or transformation. And there's a lot of questions around, okay, where does that show up? Who are the people that get enabled by that and they can do even more? Who are the people that may get displaced by that and what do they do next? So we're in one of those periods where it's a serious topic and a real conversation. I do think that some of the negative kind of commentary and messaging out of, you know, the industry or even, you know, kind of political, you know, institutions probably is overweighting the negative side and underweighting the positive side.
4:41For instance, I'll give you one example. So there's the sort of death of the software engineer topic that comes up. And that comes up because these AI models are really, really good at code generation. So they're really good at writing code. And like you look at them and you're like, oh my God, that's incredible how much code it just wrote. And it wrote that code as well as another engineer would have. And that's all totally true. But to get that code into production, to make sure that it's secure, to have it maintain an application on an ongoing basis that doesn't get hacked, to make sure it's integrated across all your other data systems and database and infrastructure, that still requires a tremendous amount of knowledge and expertise in the field broadly of coding and in software development.
5:19And so the people that are going to be able to best leverage the technology are actually going to be software engineers using code agents to be able to generate vastly more code output than they would have been able to before. But that's today. Do you ever think about like in five years, AI is going to be able to do that? I don't know. Look at the market, strategize around some problem that that the market is not solving yet. Build a company, develop software, and that's it. There's a lot of data signal that isn't digitized in a format that the agent can go with. And there's a lot of ways the agent can get confused by accessing the wrong information or doing the wrong thing that you didn't intend.
5:55And so for all of these reasons, it leaves humans in some kind of supervisory capacity for what these agents need to go do. And so does it need the same number of humans as we have today for the exact same workflow? No, not usually. But are there a lot new workflows that businesses will now do because they have access to those agents? That's the sort of bet that I have. And so the way I kind of think about it is, is if you think about that five-year-out scenario, let me paint a slightly different one. I'm a small business. Pre-AI, I was three people. We were selling something online. It was a good business.
6:30It sort of paid the salaries of these three people. But let's pretend I had even more ambition and I wanted to go after a bigger market. What do I do if I'm those three people? It's like, I have to hire a sales team. I have to hire a marketing team. And a lot of people are just like, that's a really high barrier to entry to grow my business, you know, meaningfully. Now enter agents. And you're like, oh, I want an agent to go and generate this marketing campaign. Or I want this agent to go and build a better website that delivers a better experience for my customers. Well, what happens next? If it works, now you have more customers.
7:00Now you have more supply chain issues. Now you have more customer kind of interaction challenges. You have new features they want you to build. then all of a sudden because you had agents go and get you some of the way to getting some of the work automated my hunch is that same three-person business becomes five people or becomes ten people because they now have automation that's augmenting the prior constraints and limitations that they had i think that's going to happen as much if not more than the scenarios where you have a company that is sort of saying okay i have 2 000 engineers today i'm going to have 1500 in the future i think it'll be a much more diffuse set of growth that happens through the economy.
7:35Some of it will be different roles, but I'm very optimistic that we're going to use this technology to grow more and do more as opposed to just replace. And because we're doing more, we're basically consuming more, right? And solving more problems. So we're becoming a more abundant world. More abundant. And you can't escape some ultimate constraint. There's always some constraint in the system. There's a new bottleneck that emerges. I have lots of things that I've tried to automate where at the end of the automation, the very next thing you have to do is a human has to do some work. It has to follow up with the customer because I just can't fully automate that entire process.
8:09It has to update data in some system. It has to go into three meetings and coordinate with some other set of people. It has to go to the customer site and do some implementation. There's always constraints in the system. We just haven't identified all of the new ones that happen when agents arise. There was a funny article about a week ago in the Financial Times where lawyers are now being inundated with questions from their clients because their clients are going to AI agents and asking questions about legal issues and they're drafting documents or whatever. But guess what? Like if you were to go draft a contract right now, the very next thing I predict you would do is you'd go and send it to a lawyer and say, can you just make sure this is like going to like, you know, hold up in court because in the 3 % chance it's not, which is basically maybe the hit rate of like, like what an agent will get right or wrong, that's not worth the risk of saving$500 of talking to that lawyer.
9:05Yeah. Same with like financial advisors, right? You still want to run something through a hearing. I am like not that interested in automating my tax, my personal tax process. Like I am totally fine with, with, you know, the, the one-time fee to just make sure that that is just like a clean process from, from somebody that has like done this for 10 years or 20 years or 30 years. And, And there are just some parts of the economy, which is naturally already where, you know, dollars tend to flow, where you're like, I just want this done well. I want my doctor to be really good. I want my lawyer to be really good.
9:39I want my tax advisor to be really good. I want them using AI because if they could somehow like review more of my data or look at more of my patient history or look at more of my legal history, that would only be a net positive. But I want that person ultimately to have some degree of accountability that's on the line. These agents have no accountability. They're not on the line. They're not on the line for anything. They're going to disappear in two seconds later. And you're going to blame Claude or Ovenay. I can't blame Claude. I can't blame Claude's weights. I can't sue Anthropic. Like all of those things, we have rules.
10:12We have laws. We have accountability for the rest of the economy. You don't in agents. And so somebody eventually needs to take on that accountability. And this is more of like the more like legal related issues. But there's still lots of things where you're like, You want to look at your contractor in the eye and say, can you deliver this thing for me? Not in a, I'm going to sue you, but just like, I want to make sure that you can deliver on that brand campaign and it's going to go super well. Yeah, it's one of the human brain. Yes. Human brain behind it. I even feel it with social media, right?
10:38I could totally generate a lot of posts with AI, but I just don't want to post AI generated posts. I want a person who knows my taste and my tone of voice to look at them. Yes, maybe generate ideas with AI. There's another funny thing. This is like totally random and not. And this is probably more tractable in software over time. But there's another funny thing, which is I do think people will kind of get like, they'll probably get prompt fatigued at some point, which is like, man, I have to always prompt this agent the same way every single time just to make sure that it like works or whatever.
11:10Like humans don't require that. But then you can do a cloud project with instructions. Yeah, sure, sure, sure. And some people will get really, really optimized on that. But the nuance is there are some parts of your business where you just want the person to be able to have that context. And you just want like there's a lot of things I could probably automate if I like put my mind to it really, really hard. But like now I am basically doing the work of like five people. And it's just now I have to hold all of that context in my head as opposed to previously that context was in the head of of of those teammates.
11:40And I at some point like my brain is going to explode. I'd rather those people hold on to that context. and it's sort of worth it. The value of the thing being done well is worth it and worth paying for. And so, again, I want that person to use agents, but I don't want to have to keep track of all their contacts either because I run into a limit. So you're responsible for the process and it's in your brain. I don't want to be responsible for our company's legal review process. I don't want to be responsible for the invoice process. I don't want to be responsible for the brand creation process.
12:08But actually, that's maybe a kind of a really key point though that you just said, which is the more agents you deploy, for yourself, you take on the role of the equivalent manager in another kind of organization, the human manager. You basically have to be responsible for whatever the output is. And so the more horizontal you go in what you're giving agents, the more functions you now have to - The more your brain explodes. Yeah, exactly. Literally. And you see this in the Valley. People are totally tired. I have never met a founder right now or somebody working on a startup that's like, I'm getting great sleep.
12:43Oh yeah, my 50 agents are running my startup and I'm just sleeping. Nobody's doing that. It's the exact opposite. They are managing the 50 agents and they are stressed out of their minds. I was talking to a lot of scientists and they're the ones who tend to be most worried. I talked to godfather of AI, somebody who has been studying AI for 15 years and they're the ones painting the picture. Was it Hinton or who? Yoshua Benjiro. Oh, Yoshua, yeah, yeah. Yoshua, he's like, we have two years. Like, what are they not getting? He's been saying we've had two years though for probably 10 years. That's true.
13:13But what are they not getting? Listen, I have deep respect, obviously. These are the best minds in AI, and we are riding on their work. So obviously, a tremendous amount of respect for what all of this kind of category people have contributed and their ideas. I don't know if you've interviewed like Jan LeCun. No, yeah. Okay, well, it'll come. And I kind of, you know, more Mignon's camp, which is there's still just a fundamental limit to these systems. They have to be, the work has to be reviewed. Any error rate above like 2%, you know, you still then need some accountability in the process. And everybody kind of says, well, humans are already doing that.
13:58It's like, yes, but back to the point, I can fire the human. And so there's some accountability at scale in the structure that exists where the agent just doesn't have any of that. And so somebody has to take on accountability for the output of that agent in your workflow at some point. Because what you're not going to do is be fine when Bank of America says, ah, we lost your money because the agent kind of made the wrong investment decision. And you're like, okay, but that's not why I hired you. Exactly. And so that part exists very broadly throughout our organizations and throughout the economy.
14:31And so I think what some people in the AI ecosystem that lean more to the sort of rapid takeoff, you know, kind of quick takeoff scenario is that they're thinking that because the agent can do lots of stuff really well, that that sort of diffuses across the economy in a way that is sort of this destructive scenario. And I have, I don't know if it's a benefit, but it's certainly a reality. Like I have the fun, pragmatic reality of like, I work with enterprises day in and day out. And these are enterprises outside of Silicon Valley. They're in the real world. They're the manufacturers of our products.
15:08They're the banks that we, you know, kind of bank with. They're the life sciences companies that develop drugs. And what these really amazing researchers and thinkers don't do is they don't talk to those people who are actually implementing these systems. And so they see this incredible capability take off, but they don't realize the diffusion of that AI across our organizations is ultimately constrained by and bound by 30 other things that doesn't really relate to the super intelligence that's in that model. It relates to how do I implement this thing in a safe way with the right safeguard so it doesn't blow up my data structure?
15:42I just think that the timescales are wrong. The way that people imagine the AI being implemented in society is generally wrong. Now, there's one real risk that I agree with, which is there is cybersecurity risks. There are risks of mis - or disinformation challenges. Those are very real. We need to work through those. But I'm much less inclined to believe this thing takes off, it replaces all white-collar work, and then we're in some really bad scenario on that. When you need to build up your team to handle the growing chaos at work, use Indeed Sponsored Jobs. It gives your job post the boost it needs to be seen and helps reach people with the right skills, certifications and more.
16:22Spend less time searching and more time actually interviewing candidates who check all your boxes. Listeners of this show will get a$75 sponsored job credit at Indeed.com slash podcast. That's Indeed.com slash podcast. Terms and conditions apply. Need a hiring hero? This is a job for Indeed sponsored jobs. Pool days call for cookouts and lots of laundry. This Memorial Day at Lowe's, save$80 on a Charbroil Performance Series 4-Burner Gas Grill. Now just$199. Plus, get up to 45 % off select major appliances to keep dishes, clothes, and food fresh. Having fun in the sun is easy with us in your corner.
17:01Our best lineup is here at Lowe's. Valid through 527. While supplies last, selection varies by location. See associate or lowes.com for details. But we still hear all the news about layoffs happening due to AI. Do you think it's due to AI? Some of it is definitely not due to AI. It's overhiring during the kind of zero interest rate era, the COVID era. So there's some phenomenon that kind of relates to that. I would say that some of it, it definitely could be related to AI. Like there are some organizations that they're like, listen, I had 3000 people working in engineering before. My product roadmap is sort of not doesn't need to triple in sort of scale.
17:40It needs to grow by 50%. And so I think that if each engineer can be 2x more productive and my roadmap only scales 50%, then I think that there's some sort of savings there as a result of that. And then they might do a layoff in that scenario. So I think that is real. It's not something that I can sort of gloss over. But what I see from customers, and you can go online right now, and I guarantee if you took five random companies in the Fortune 500, just as an example, take five random companies. I guarantee that every one of those five companies is hiring software engineers right now. Yeah. And so where are they hiring their software engineers?
18:19They're hiring them. There's an interesting posting right now on Eli Lilly's career website, which is a lab software automation engineer. This is a role to use AI to help sort of automate and increase review of lab results and automate the lab process in life sciences discovery. The kind of general idea of like AI is going to destroy software jobs, that is not playing out empirically. And I predict it will not play out ultimately. Interesting. So you think we're going to get more jobs in the next few years. When you're hiring now, how is it different from hiring five years ago? What are you looking for in a candidate?
18:55it. So I think right now is a great time to be going deeper technically. It doesn't mean you have to be vibe coding all the time and building entire products, but you should try and really understand what is the agent doing? How does it work? How does MCP work? How do CLIs work? How do skills work? And getting really well versed in that. The people that are doing that will have a huge leg up in the next kind of three to five years because all of these companies will be hiring for people that can do that within their workflows. So we're definitely looking for people whose technical acumen is growing, whose AI sort of savviness and fluency is growing.
19:28You want to be using these tools in your free time as much as possible so you, again, understand kind of how they're working and what's going on. At the same time, I don't think a lot of the... I think it actually still matters that you have some degree of domain expertise. You're really good at marketing. You understand what customers want. You're really good at selling. you're good at product management and interviewing customers and assessing markets. Those are these timeless skills that transcend any kind of technology revolution. And so AI is just a way of augmenting those domain skills. So in some respects, any role that we're hiring for, marketing, sales, finance, engineering, et cetera, we need all of those domain skills, but also we need you to now be increasingly kind of AI fluent or a little bit more technical.
20:19Can you recommend top three apps that people should be using? You know, I mean, it probably won't be much of a surprise. I would download Codex. I would download Cloud. Even for non-technical people? Yeah, 100%. Well, partly it's because Codex is becoming more inclined toward knowledge work use cases. And what should they be doing with it? Like automate a process within their... Automate a process. Give it just a crazy problems and see what happens. Like go do this research in this market. you know wire up multiple mcp servers to data sources you have um so you understand how does it work like how is it queering that that other system how does it how is it accessing my email like yeah like oh scary oh no actually i understand it now like like get get a sense of how that all kind of is working together so i think just any one of the top ai tools for productivity maybe for coding uh is a good way to get started and it'll already get you like 90 of the way there So Codex?
21:14Probably Claude Cowork, Perplexity. These are some just easy ones to just get started with. And you'll have a good sense of kind of what the market looks like. Do you have any examples of workflows that you've automated for yourself and you'll never go back to manual? The kind of things that I'll never do again is like I'll never do like market research in a traditional way. So I'm often asking an agent to like go and analyze, you know, a hundred different companies worth of trends or information. I'll just never do that again. Like I'll never go to Google and type each company in and do the research.
21:46Like I'm going to have an agent go in and fan out, do all that. And then maybe I'll click like all the underlying sources and verify something or double check something. So lots of market analysis. I'll never open up code editor and like, you know, type code again. And I wasn't for the past many years anyway, but like the reverse is true, which is now I can actually like get prototypes built when I couldn't have before. so anything coding related even design is like you just go to chat to poutine you're like hey i need this idea done could you just like make it like this and then it gets you like image the new image rendering model gets you like 75 of the way there you hand that off to a real designer and then they kind of do the the full thing so there's a lot in the ideation the creative process the market analysis customer research all of those domains that that i am heavily using ai for is there a certain way you structured memory?
22:40Uh, like, did you, cause I hear some people like upload personal constitution, like their principles of work. Is there anything like that that you've done? Um, I'm less fancy on that front. Um, and partly because I don't even know what I would write down, um, because I'm all over the place. So, uh, so I am, I don't have a lot of things yet that I would, I would know how to really document. It's more process specific, in which case, in which case back to this sort of reprompting issue, I'm more just on the fly, just giving it pretty clear instructions of exactly what to go do. So like, I feel like I'm a pretty good prompter.
23:12So every time it's a long, long prompt, right? Every time it's a long, long prompt. And I'll store those off in various places. You know, by virtue of Box, like we're like, we store lots of data. So I have lots of documents that have information in them that I'm using, you know, constantly. But it's not as awesome as like a sole file or a personal constitution. So it's not like we're talking right now and 50 agents are replying to emails. At the moment, if you get an email from me, that's a huge mistake in our system. So I am not emailing you right now via an agent. Got it. Got it. Okay. So another thing.
23:50Now, five years from now, could that be a process that gets automated somewhere? For sure. Like just as we've always had automated email systems for sales reps or whatever. But it probably won't be that it would be like, oh, hey, Aaron, I have a question about this thing. and then I'm going to have like an agent go do that. Partly because like, that's actually just like the kind of context that informs me of what's going well, what's not working well. If I, if I automated all of that, we wouldn't know the next thing in the business to go fix. So you don't have an agent that's running your business basically.
24:21Is there like, cause I talked to someone for no reason. They're like, I share all my business decisions with my AI. And then it looks at all the conversations I've had with my team and it gives me strategies. Um, I think, um, first of all, I think that's really cool. That use case. I think more startups are doing that. I think if we were at a brand new company and it was like five employees, there's a very real chance I'd be doing more of those types of things because I would be like, okay, I probably need to like build out our first marketing engine and I need to build out our sales engine. And so I would be kind of, I would be documenting way more of that at our scale.
Read the full transcript
24:55You know, the really interesting, important work is being done across the organization. so so that type of of work is more knowledge that like our head of brand design or our head of product design or our best brand design you know designer needs to know or our product managers in each of the individual domains um the stuff that that i do is is sort of look across those areas and try and add you know extra nudges in the right direction and kind of course correct and um and you know an agent could certainly help you know give me advice for how to do that but But I'm still at the point in my life where I'm like, I'm going to see if my brain can do it.
25:33It's also the founder energy, right? When you're talking to your team, you don't want your agent to be talking to your team. I think there'll be some spectacularly hilarious examples like that that probably over time sort of subside. We're already seeing them, like company data being deleted. Yeah, you're going to do that kind of stuff. And I like, you know, these agents are like, I could be proven wrong about this and maybe five years I'll be like, yeah, I was totally wrong. And this is where Jan LeCun, I think, would agree. And some other, you have a really interesting divide in the industry, which is are these like probabilistic pattern recognition machines or are they truly able to kind of go off on their own and think for themselves?
26:20and depending on kind of where you land on that continuum, then you have some big judgments that get made. So I kind of think about it as there's lots of business decisions I have to make or that lots of people have to make where just it's a brand new, net new event that happens. And I couldn't have documented what to do in that situation. And maybe I could have if I spent like a year writing down every single thing, but it's just a new thing that happened. And so if I try and imagine an agent running around, everybody's asking the agent questions, it's only going to be able to answer the thing that previously I have in my sort of repertoire of answers.
26:59Many of the things I'm working on are the brand new, net new things in the organization. So me being an agent across the company would kind of be useless because it would only have, you know, help with the things we already know. Yeah. Previous strategies. That makes sense. Now, just to share the opposite it for one second. There's a lot of stuff. I'd say 80 % of our corporate information is to be reused purposefully. Like you don't need people like making up a new answer to an HR policy. You don't need people making up a new answer to what is Box's security functionality and how should I position it to a customer.
27:32So in those cases, actually all of your enterprise information, which is what we do, you know, as a business is like that enterprise information becomes valuable for agents because they can look at the documentation. They can look at the sales pitch. They can look at the meeting that was recorded. That actually becomes very useful information for that kind of run rate 80 % of your company's work. Yeah, but it's for specific work, so like a founder strategy. Yeah. And you said some next great companies are going to be founded in the next three years. And you gave a very specific timeline. Why three years?
28:07Well, I mean, it could be three and a half years. Which is like not 10. It looks like we have a very limited gap in the market where you can build something great because then it's going to be another like boring 10 years. Basic theory is like, you know, these market windows happen every 10, 20, 30 years in technology. The mainframe, the personal computer, the internet, the cloud slash mobile. So there's already been kind of four of these eras. And if you look at the biggest companies, you know, in tech, they generally correspond with when these windows open. There's a couple of examples that don't.
28:44Facebook didn't correspond with any particular window. It was more of a social change that occurred as opposed to a technological change. But most other things, Google, Amazon, Microsoft, Apple, the real turbocharging of IBM in that era and Intel and so on, they correspond to a new technology at the foundation level emerges. and then you have this opening where a bunch of new companies kind of respond to that. In our era, it was Salesforce and Workday and sort of enterprise software companies like Box that sort of were able to capture that moment. And then in mobile, it was like Uber and DoorDash and another set of companies.
29:28So we're in a window right now that has all of the makings of that, which is AI is now emerging. Companies are going to want to apply this intelligence in various areas. And so there are going to be a lot of applied AI companies that bring that intelligence to businesses, to society, to consumers in these applied use cases. And the only reason it's not like 10 years is because there's a lot of network effects remotes that get built. So if you build one of these companies and you're capturing data from the customer and you're improving the feedback loop of the agent, that'll just make your technology better and better over time.
30:04whereby at least on paper that that product should become more uh sort of uh strengthened in its competitive advantage over time so that's why it's like yeah it's not like an infinitely long window yeah because you know it's very hard to disrupt walmart today because customers have been using it for decades yeah um and uh and so you kind of want to be in one of those spots as these markets are are emerging are you seeing any gaps in the market where a startup should be working on right now? Still, I mean, tons. But I think there's still like, I think, you know, everyone sort of knows the example of like Harvey right now for legal.
30:44I think there's still lots of job functions, industries that will have their Harvey. Like, I don't think we've heard the end of the Harvey for X. I think there's going to be new infrastructure that gets built out because these agents are going to need new kinds of tools beneath them. There's all this new interesting stuff around when agents are doing work within software, they need more headless technology that they have access to. They might need payments. And so Stripe and this new company Tempo is providing payments for agents. Well, now if an agent can pay money, then you can start to think through like, well, what would the agent pay money for?
31:22And there might be new businesses that emerge that the agent is now going to transact with. They're going to need data, probably. They're going to need infrastructure. They're going to need to do tasks for you in the economy. There's lots of things that you can start to imagine that will become these new business models because of what happens with agents doing this work. With a whole new layer of active creatures in the market, which are agents. Yeah, 100%. If you were starting today, can you walk me through a plan? What would you do to find the right idea, to test it, and to make first money?
31:54My first thing would be some mix of like, you know, assume that we've got the most intelligent sort of system on the planet. So we have this incredible AI intelligence and just imagine that emerges. Then the question is where in the economy would that add the most amount of value? And then try and think through like, like are there spots where like an incumbent isn't effectively responding to that? So that'd be like one framework. Another framework would be like, where in the economy is it hard to deploy agents because there's a lot of other kind of systems that that those agents need access to and that's usually where like there's lots of work to be done to get the agent to work within the environment i'm pretty excited by a lot of these new kind of professional services it integration consulting firms that are emerging because when you go to the real world and you're like oh would you like to automate your work with you know co-work or or codex or any of these systems they're like yeah that'd be awesome And then they show you their environment.
32:50And it's like, ooh, it's going to be a lot harder than you think. What markets? Anything. Anything. Everybody. Healthcare, law, life sciences, bank, just every industry. Because if your company is more than five years old, pre-AI, your data is all over the place. You've got 30 different systems you're working with. Your workflows aren't documented to the prior point. So that's a lot of change management you need to go do to implement agents. So what does that spell? that spells opportunity for new services startups. That spells opportunity for the existing Accentures and Deloits of the world. It's kind of like a little bit of an up-for-grab market at the moment because of how much work there's going to be.
33:28When you finally find your thing, you want the whole world to know about that thing. So you use a thing called Canva to make it an even bigger and better thing. Whether you want to create flyers for that thing, make presentations for that thing, or design merch for that thing, you can do anything. so people can see your thing, feel your thing, love your thing. The next thing you know, it's a thing. Canva, the thing that makes anything a thing. You can't reason with the sun. Trust us, we've tried. This summer, it's time to put that angry ball of fire on mute. Columbia's OmniShade technology is engineered to protect you from the sun's harsh rays that can burn and damage your skin.
34:12The sun is relentless, but so is our gear. Level up your summer at Columbia.com to spend more time outside and less time slathering on aloe lotion. You're welcome. Columbia. Engineered for whatever.
34:28How do you decide between like building versus? Maybe the only thing is like Mark Cuban has had this riff and I fully agree with it. There's going to be like a lot of opportunity both for companies, but even just these will be roles that if you're like graduating right now, you might want to think about is like, who's the person that shows up at the 10-person consulting firm in Minneapolis, just to pick a non-value location? Who's the person that shows up that helps them take advantage of AI? Because they don't have a big IT department. They don't have a way to wire up their agentic workflows very easily.
35:02There's going to be tens of billions of dollars, hundreds of billions of dollars to get made between jobs and services firms in just that over the next decade. Also, as an entrepreneur, when I'm thinking about that, but what if Claude just makes the process really easy? I don't know. You just deploy an agent. They build a specific agent who goes into your email, whatever you have, your box, and creates the whole ecosystem for you. How do you think about that? Because these companies are getting more and more powerful, right? If I took your exact scenario and I'm like, okay, an agent's going to read through my entire email inbox in that, in that scenario.
35:36And then it's going to access Salesforce. And then it's going to have some kind of like workflow that participates in like even me as a, I've been building software for 25 years and I use every single tool that has ever been produced in AI. Obviously not literally, but, but like pretty much I don't feel comfortable implementing that workflow right now. So the idea that that 10 person company is going to go and set that up. And just because Claude became super powerful, I am skeptical that we ever get to that point. Because the reason why I'm not comfortable with that is like, I don't, I have to think through the guardrails of like, what happens if somebody emails me and then says, Hey, Aaron, I, you know, you, I need you to pull up this Salesforce record for me that you told me you would, you would look at and you can send me that information.
36:31Well, if my agent has access to my email in my Salesforce, then the agent should, by design, answer that email question and go pull in the Salesforce record and then send it out. That's like a non-starter. You can't just take any untrusted email coming in and then have the agent... And distribute information. And distribute information that your tool has access to. So even me trying to think through how to implement whatever your scenario was just now, I would have a hard time thinking through, how do I set the right guardrails? How do I have the right alert mechanisms to me? How do I have the right sort of human in the loop of like, should I review all of the emails before they go out and have an interface to do that?
37:07Should I have some escalation mechanism that like pings me on my cell if like I need to look at something? How does the person on the other end of that email inbox, not how do they, how do they get to me as the real person and like get, you know, how do they escape the agentic loop that they're in? There's like 30 questions that I even have thinking through whatever that workflow is. So it's not a matter of Claude is so powerful. It's a matter of like how the systems talk to each other, the safety mechanisms of those systems. How do you define the, how do you define the actual workflow? So it gets done in a kind of safe and reliable way, that's the work that a technical person generally needs to go do.
37:46Okay. So, but that's like a big shift from, you know, being manual to getting automated as a company. What about niches where like we see Figma stock go down when Claude releases the design feature, right? And if somebody is working on that type of feature and they're afraid, you know, with the next Claude upgrade, it's going to be gone. Well, that's a different issue. So, so, So that's a different category altogether, which is, you know, how much will Claude or these AI models eat into the business models of different industries or different providers? I think that's more of something where you just have to be very thoughtful right now to not just build anything.
38:23You have to build things that like, what are you building where even as AI agent progress continues, no matter what, no matter how much it continues, it could be infinitely powerful. There's still some other thing that that agent is going to need to do. It's going to need to put its data somewhere. It's going to need to incorporate into a workflow. It's going to need a human to take the information and put it into the real world. Over time, more and more value will start to look like things where, again, like it's a well-governed process that has lots of security or compliance needs. You have to trust the underlying system.
38:58You know, probably just like quick personal productivity tools maybe will be less relevant. At the same time, like in the Figma example, I think Claude design is actually very, very cool, very powerful. I play with it a bunch and it like, you know, generates, you know, amazing designs. But at the same time, I still want our design team kind of going and doing the last mile of work. And right now they're doing that last mile still in Figma. Even these things are not as binary as I think maybe the Wall Street, for instance, would suggest. So that's why it's still kind of a, you know, we're in a pretty dynamic period right now.
39:32Yeah, and it's also because I feel like the stock reflects what we're thinking about the next two years. And because this is evolving so, so fast, sometimes as an entrepreneur, I'm like asking myself, okay, I'm building these apps. Why don't a language learner just go into ChatGPT and like build the Apple Vibe code and that for themselves? I mean, I think it's a question that every entrepreneur should have a very big whiteboard that like thinks through various game theory events that could happen. and where will your value get compressed and where will it not? And it's hard to, you know, in any kind of generic way, have a perfect answer because it is a very busy, complicated time.
40:11But again, kind of ironically, in like the more macro sense, I think the more that AI is sort of doing in these kind of automated things, you're just going to see new constraints begin to emerge. Like, you know, a lot of people like healthcare classically as this example. And I think Jeff Hinton, you know, had, I don't have the perfect quote, but I think, you know, he felt like radiology would reduce as an example because, you know, AI will get really good at looking through radiology images and self-driving cars. And now we still have radiologists driving to work every day. Oh, sure. Yeah. I think it was that.
40:45Oh, yeah. So what also happens is these other things that occur, right? So like, we might have like AI that gets the radiologist 90 % of the way there to like look at the right thing or get some suggestions, at the exact same time, what that's meaning is we're doing vastly more imaging. We're doing vastly more scanning. Way more people now can go do it. More accessible. It's more accessible. And so actually now the demands on that role end up increasing as a result of that. So there's a lot of parts of the market where actually AI facilitates lowering the barrier to doing that work. And by lowering the barrier to doing that work, more people participate in it.
41:21And as more people participate in it, a new constraint gets kind of backed up that now real people need to go and kind of, you know, get involved in or go and work on. Yeah. I feel like the more I play with AI agents, I do realize that I need a person at the beginning of the process and the end of the process. So I still end up having more people. Yeah. And again, it's just like a question of like, how many roles do you want to play within your company or your team? Like, do you want to play designer, developer, marketer, strategist, sales rep? No, you're just like, ah, at some point. So yeah, the solo entrepreneur is already used to that because it was, you know, we or they have been doing that forever.
42:01Like when I did, uh, startups before box and I was a solo founder, like, man, I, you had to do 10 things and you're like, you're so tired. And if I could have ever hired somebody to go do half of those things, I would have. So could AI allow us to get these companies to a little bit more scale to the point where then you can hire that next person? That's more of where I think this would go. And do you think it's the best time to start a company now? I'm kind of a stickler for this one key point, which is it's only the best time to start a company if you've got a great idea. I think that great ideas can exist in any kind of period of time, but I'm not in the camp of just like everybody should start companies because it's I mean, you know, it's like really hard work.
42:46It's extremely stressful. You're working like mad. I don't think that people should feel pressured into starting something because it's one of these windows. When I say it's one of these windows, it's just to reinforce the point that like this is the moment where the best ideas probably will get built. That doesn't mean that you should start one. It doesn't mean you have to rush yourself to starting that. Yeah, because if you rush yourself to starting a bad idea with one of these moments, you're no better off. So I would say it's a good moment. You have an incredible amount of leverage. That also comes with more competition because basically by lowering the barrier of getting ideas out in the market, what do you get?
43:25You get more competing ideas. If you get more competing ideas, that's more noise that customers have to deal with. So interestingly, and back to the job thing again, interestingly, it's not so much like now the idea, getting the idea out there that's going to matter it's going to be like man do you have like do you have somebody talking to customers do you have are you doing sales are you doing marketing and so there's a new constraint which is like the constraint isn't code generation the code this constraint is is are you in front of customers enough and and are you marketing marketing which is a new set of dollars yeah uh if you could become 19 again today and start over would you exchange that uh to what you've currently built like to start over again would you do that am i starting in 2026 or back in 2005 No, 2026 is a 19-year-old.
44:09Would you do that or would you just stay put with what you've done? Oh, I see. I see. Well, I'm the most excited we've ever been on what we're doing now. So I would certainly pursue what we're currently doing because part of it is historical, which is, you know, we've earned the trust of 120 ,000 customers, which is a good launch pad for the next set of things we want to go do. um so and then i i just love the the kind of things that we get to do with customers we get to work with every industry and every size company and we get to help uh you know space launches and medical discoveries and blockbuster films get produced so like i'm very excited by what what our platform does with agents um at the same time i have lots of friends that are doing you know companies and i'm like oh that's a really cool idea right now and it looks very exciting and And and and so I'm just in a period of like I'm impressed and excited by lots of stuff while also being, again, incredibly stressed constantly.
45:07Any jobs that are going to disappear in the next five years? I think there's going to be work that gets compressed. And and then and I think you're going to take those people and often repurpose for for, again, more of the agent manager escalation path or proactive versions of that work. A very kind of clearly obvious one is, and this is something that companies always, you know, tried to sort of automate to some degree. Like if you're emailing a company and you're saying, like, I need you to reset my password, that is probably not going to be a person. Like customer support, right? But even that, customer support is this funny one, which is like, we think about it as a monolithic thing because we call it customer support.
45:49There's tiers of customer support. there's like the first line of customer support that we will most certainly automate which is change password change password and i don't mean to like you know over minimize that thing but like there's a lot of tasks like that which is like i need to download this thing i can't log in i have this issue whatever that we're going to fully automate but there's a lot of customer support which is like i need you to get on this call with me and look at my my specific problem in my computer and why this thing isn't working and we just have no way to automate that yeah like maybe will automate like the next line of the of the set of questions but you can't you can't get to the the final thing i had i had a friend have a problem with box two weeks ago he just sent me some screenshots and there's a 0.0 chance that he would be able to have asked the question with an agent so it had to be you well in this case it actually it had to be a senior product manager i had to get the senior product manager to the person but he couldn't have talked to a chat bot and answered the question.
46:50But what about like bookkeepers? I had an issue with my Mac last week. I spent 10, 20, 30 minutes on AI trying to diagnose it. Never worked. Had to call IT. They had to come and diagnose it. Couldn't replace that. Oh, okay. What about jobs like bookkeepers or? You know, some of these jobs, like again, they've been on the path already to how do you already automate as much of that away as possible. And so agents kind of are just another sort of layer in that. But again, you know, sort of the same answer. There's still always an escalation path because there's always the exception. There's always the weird anomaly that occurred.
47:30And you can't have, like the thing that you can't do is I can't moonlight as a bookkeeper. I can't moonlight as a lawyer. So at some point there still is this final path in the escalation, which is I may have been able to automate 90%, but you still have that one part. I had this legal question two months ago, and I asked every AI agent the same legal question. And every single one basically gave me the same answer. And then I called a lawyer, and they basically gave me a much more kind of contextualized answer because they could decide how much risk I wanted to take on or not take on. Knowing your personal situation, right?
48:11No, they know my personal situation. they also know the fact pattern of like, like, how does the industry tend to think about this one thing? And all the AI agents were giving the sort of mean answer of that particular topic, which is in this case, it's like, it's the more conservative answer. It's the thing that it should be trained against because it can't give you the, it's not going to give you the more liberal, risky answer. But when you talk to a lawyer, they're like, well, actually, yeah, this situation won't actually occur because of X, Y, Z fact patterns. And so those are the kind of things where like you then are like, I want somebody that has seen 20 years of this stuff.
48:46I don't want a model that was just like looking at Reddit and deciding, you know, how to use that information. Okay, my two last questions. You have a six-year-old, right? Almost seven, but yes. Okay. And four and seven and a half months. Oh, congratulations. Okay, are they going to go to college? Shoot, maybe I shouldn't have leaned in so much to the question. um uh i okay i am here's the one problem with me um as a b2b enterprise software person i am like boringly pragmatic and so i just think change happens more slowly and and it's funny because i have this like weird duality which is like i adopt every tool like i was i was wearing google glass like like in week two i buy every vr headset like i i lean into every one of these tools because I'm just like, I'm excited as a personal user.
49:40I love technology breakthroughs. It's amazing. And then I'm like, and then I go in the real world and I'm just like, man, that whole system over 300, 500 years that we've built up is like, is that really going to change because of this one variable? So on the college thing, I struggle because I'm like, on one hand, from first principles, it doesn't have to exist. My seven-year-old, almost seven-year-old is already way smarter than I was because he can, every question that comes to his mind, we're like looking up the answer right away. Whereas like, I don't have like a perfect memory of being seven, but like, like I didn't have like an instant resource for like every question, but like he wants to know like how fast a paragon Falcon can fly.
50:25We get the answer. He wants to know like how big the, the Atlantic ocean is. We get the answer. Like, like, and so he's just like a sponge for like unlimited information. On one hand, you're like, wow, that could probably replace like a lot of the traditional sort of, you know, ways that we think about these institutions. But then you're on their hand, you're like, well, you know, what is college other than another four years of high school, but with a little bit more vocational kind of orientation, a network of people that you want to be with and learn with and make connections with, a kind of transition period into the real world because, you know, you're still kind of young at 18.
51:03so like so that then i'm like a pragmatist i'm like does that really change in in this like super intelligence world or is the curriculum just changing and the format maybe changes um but like does everybody want to just be at home with their parents talking to an ai bot um like no so so it's like i have these other like you know kind of sort of counter pressures now things that should and must change like at a at a socio like societal level is like man can we have college cost a fifth of what it does because it's insane. Like, like, should you really go into debt for 20 years because you went to medical school or you went to, you know, get X degree?
51:39Like that's, that's incredibly insane. So like, should we use abundance to, to bring the cost down and try and do that as much as possible? Absolutely. So there's some things that need to change about college, but does the very concept change? I, I, I always, I always struggle with that one. Yeah. Same, same here. I feel like as a society, we're really slow to just change dramatically when it comes to foundations when college is one of them. Okay. Last question. Advice for entrepreneurs who are starting today. I would say just like back to the earlier point, lean into the tools, like learn the technology, see what's, what's, what's possible with it.
52:12Um, make sure you're riding the tailwind of, of what's happening in technology. Uh, you don't want to be, you know, kind of hitting a headwind, uh, where you're kind of going against the grain of the AI. You want to be like riding the AI wave out, um, which can mean a number of things. It might mean do things that actually in a world of AI become more important because people don't want AI to do that thing. So it's like, it's like this counterintuitive, like riding the AI wave might mean do a live events business. Like that's what other people are doing. Yeah. Like, like, like, do something where we will appreciate this other thing in the economy because AI is sort of so abundant or, or, um, uh, AI makes getting healthcare questions answered so quickly.
52:53So you should probably be doing hospitals because now more people are going to be actually needing real - Wellness clinics. Wellness clinics. So sometimes it's a technology thing that you do. Sometimes it's a thing that the technology is related to an underlying broader societal trend that will become more important as well. Build one of these consulting businesses that helps deploy the AI. I just think there's going to be like build a child care service because we're all sort of our brains are exploding and we need help with kids. There's all this kind of stuff that is going to need to exist.
53:29Thank you so much. I like your positivity, especially after talking to some scientists. Thank you. Thanks a lot.
From the publisher
Aaron Levie built Box into a $4 billion company used by 64% of the Fortune 500. Now he says we're at the best moment to build an AI company in 15 years — and the window is 3 years.
In this episode, Marina sits down with Aaron to talk about what's actually happening inside enterprise AI, why younger founders have a surprising advantage right now, and which jobs are genuinely at risk vs. which ones AI will make more valuable.
Aaron shares why AI agents still need humans at the beginning and end of every process, why the real new constraint isn't code — it's sales and marketing, and what he'd do if he were 19 and starting over in 2026.
If you're building, thinking about building, or trying to figure out your next career move in an AI world — this one is for you.
Topics: AI startups, entrepreneurship, future of work, enterprise AI, career advice, business building, AI agents, Aaron Levie, Box, Silicon Valley
Links:
📩 Follow my Newsletter: https://siliconvalleygirl.beehiiv.com/subscribe?utm_source=spotify&utm_medium=video&utm_campaign=futureproof-sub&utm_content=AaronLevie
🔗 My Instagram: https://www.instagram.com/siliconvalleygirl/
📌 My Companies & Products: https://Marinamogilko.co
