Topic
80 facts from 5 episodes, in date order. These are what speakers said on the shows, each linked to the moment it was said. They aren't independently verified.
1980s
Aaron Levie describes the first era of enterprise software, roughly forty years ago, as systems of record such as CRM and ERP.
“if you think about the eras of enterprise software, forty years ago, we had the initial wave of systems of record, which was CRM systems, ERP systems.”
1990s
Levie says earlier online-storage companies had died off in the late 1990s before Box launched.
“there had been companies that would let you store your data on the internet, but they all kind of died off in the late nineties”
2004
Aaron Levie was an intern at Paramount in 2004, the year he began the college project that became Box.
“got some internships in the entertainment industry, and then I was an intern at Paramount in 2004.”
2005
Mark Cuban became involved with Box between Levie's sophomore and junior years of college, when Box was about four months old.
“between our sophomore and junior year of college. Box had been around for about four months or so.”
2005
Cuban's investment led Levie and his co-founder to drop out of college and work on Box full time.
“That led to actually us dropping out of college and betting on the company full time and pursuing it full time.”
2007-2027
Levie says cloud computing took about two decades to spread across businesses and the migration is still ongoing.
“It took two decades for that to actually play out across all all businesses, and still, we're still going through the migration phase.”
2016
Levie says Box tried a similar AI question-answering project about six years before ChatGPT but it could not work without very large models.
“like six years prior, we actually had a project to attempt that. It just was never gonna work because until you had, like, 200, 300 billion parameter model”
2020s
Levie says Box offers agents that go through customers' contracts, invoices and other documents and extract structured data from them.
“give us your contracts, your invoices, your healthcare documents, your research files. And we have agents that go through all of that data and extract all of the structured data from that.”
2020s
Levie expects Box to charge a predictable per-user price of roughly $10 to $30 a month, with agent usage priced on top.
“There's gonna be seats for the user that will be a predictable price point, $10 a month, $20 a month, $30 a month, whatever the plan is that you're on.”
2020s
Levie argues that AI agents could increase the number of users on systems of record about a thousandfold.
“my general view is is that what what you basically have is like a thousand x increase in the number of users on these platforms.”
2020s
Levie uses a hypothetical of an agent given all company files without permissions to illustrate how it would reveal salaries or acquisition plans.
“you took all of your company's files and you put them on a server and you gave that agent the server.”
2020s
Levie estimates AI expands the software market by at least three to five times, possibly ten times.
“it's at least a kind of a three to five x increase in the size of of software, maybe a ten x increase in the size of software.”
2020s
Levie says the average enterprise spends only a few percent of its revenue on IT systems, far less than on headcount.
“usually you're spending a few percent on IT of your total revenue, like a a couple percent to maybe like two, three, 4% goes into IT systems.”
2020s
Levie says Box would spend about 5% of an engineer's salary on AI because it could make the engineer two to three times more productive.
“would we be fine to spend 5% of an engineer's salary on the equivalent of AI? Absolutely, because it's gonna make that engineer two times more productive, three times more productive.”
2020s
Levie says no incumbent software did legal contract review itself, only managed data around it, which is why agents open new markets.
“So there was never a an incumbent software vendor that did legal contract review. You had software that managed the data in a contract review process, but there was no software to do the review.”
2022
Levie says Box concluded within about ten days of ChatGPT's release that it should let users ask questions of their enterprise data.
“we realized it basically probably within ten days of ChatGPT”
2025
Aaron Levie says he had at least a hundred customer interactions about AI in the first quarter of the year the episode was recorded.
“From my anecdotes, I've had at least a hundred interactions with customers in in the first quarter of this year.”
2025
Aaron Levie estimates that about 80% of his customer AI conversations concerned work the companies did not do before AI.
“The vast majority, you know, 80%, I'm guessing, the bulk of the time of AI use case kind of, you know, conversation was spent on things that the company didn't do before AI.”
2026
Box counts 68% of the Fortune 500 as customers, according to the host.
“Aaron Levie is co-founder and CEO of Box, which counts 68% of the Fortune 500 as customers.”
2026
Aaron Levie says agentic coding could let engineering teams do three, five or ten times more work, and do it faster.
“you might be able to do it three or five or ten times faster.”
2026
Aaron Levie says he uses Salesforce about five times more than before by connecting its MCP server to Claude Cowork.
“I use Salesforce more today than at any point in history, maybe like five times more.”
2026
Aaron Levie says that in 2026 Silicon Valley insiders have perhaps an hour's head start on AI information over everyone else.
“Today, uh, in 2026, there's like, you know, maybe I have an hour, you know, heads up of information from from anybody else.”
Undated
Aaron Levie says Box stores well over 100 billion files.
“We store well over 100 billion files in Box, and you could imagine every single one of those has incredible insights and value inside of it.”
Undated
Aaron Levie says building the Hubs file architecture took about a year to a year and a half of deep architecture work.
“Because it was about a year, year and a half of just deep architecture work, like there was no way to build it any faster.”
Undated
Aaron Levie illustrates the weakness of broad retrieval augmented generation with multiple near-identical earnings drafts, whose search embeddings look equally relevant though only one is authoritative.
“you might have a document called like earnings underscore final and earnings underscore draft one and earnings underscore draft one, you know, underscore sally edits.”
Undated
Aaron Levie says public AI search services like Perplexity benefit from a PageRank-like authority signal that corporate data lacks.
“The reason why this is less of a problem for the public services like Perplexity or other is because you get the benefit of almost like a page rank algorithm for public data.”
Undated
Aaron Levie claims Box's Hubs-based retrieval service is at least a hundred times better than broad retrieval across all of a company's data.
“That has made our particular rag service, I think, you know, at least a hundred times better than just doing like broad based deployment across all your data.”
Undated
Aaron Levie describes the second era of enterprise software as systems of engagement, such as Slack and Box, which are less structured and more collaborative.
“Then we moved to systems of engagement, which was this idea of like collaborative systems, Slack and Box and other tools, where things are a lot less structured”
Undated
Aaron Levie says early cloud adoption required enterprises to trust new vendors such as Amazon, which they had not previously used as enterprise suppliers.
“They had to trust these new vendors that they hadn't worked with before. If you were an enterprise, you'd never worked with Amazon, you know, as an enterprise vendor.”
Undated
Aaron Levie predicts that enterprises becoming AI-first will take at least a decade.
“I mean, this is going to be, at a minimum, a decade long change for for how enterprises go and become more AI first.”
Undated
Aaron Levie says coding assistants like Copilot and Cursor took off because they add productivity to an existing workflow without requiring users to change behavior.
“I would say this largely explains the breakthrough in copilot or cursor I is because I get to do exactly the same thing I'm doing now, but I'm seeing incremental productivity gains right away without changing really any behavior.”
Undated
Aaron Levie says Salesforce, perhaps with a couple of other companies, invented the per-seat subscription model for software.
“Salesforce basically invented, you know, maybe with a couple other companies, basically invented the idea that you pay per seat on a subscription basis.”
Undated
Aaron Levie says per-seat subscription pricing has been the business model of SaaS for more than twenty years.
“And that's been the business model of SaaS for twenty plus years.”
Undated
Aaron Levie says Box employees report AI coding tools make them roughly 5 to 10 percent more productive, and new hires up to 50 percent more productive.
“somebody will say, Hey, it was five or 10% more productive, maybe a new hire, it's 50% more productive because they can just ramp up so much faster.”
Undated
Aaron Levie says Cursor is the fastest growing software company in history, at least in an enterprise context.
“As far as every stat I've seen, Cursor is the fastest growing software company in history, at least in an enterprise context.”
Undated
Aaron Levie says deep research features in AI assistants take about five to ten minutes of thinking time to produce much longer answers.
“The deep research moment of of this paradigm is is much longer answers i in terms of the amount of content you get takes about five or ten minutes of kind of thinking time for these AI models.”
Undated
Aaron Levie gives an example in which an AI agent reviewing 50,000 customer contracts might cost a company about $5,000.
“But now, if it only costs them $5,000 for an AI agent to go do that, they would do that all day long.”
Undated
Aaron Levie says the Duolingo memo reflects an emerging idea that teams must prove AI cannot do a task before they can get headcount.
“There's some emerging idea, which is sort of you have to prove that AI can't do this thing for for you to get then headcount.”
Undated
Aaron Levie says that at Box, being AI first means using AI to speed up customer outcomes, decision making and feature building.
“So for us, AI first means that we want to use AI as a means of driving an acceleration of the customer outcome, an acceleration of decision making, an acceleration of building new features.”
Undated
Aaron Levie says there are arguably five to six AI model makers that could each hold the leading model for a brief period.
“We have somehow ended up in a category where there's arguably five to six players, all of which you could throw a dart on a dartboard and they will have the leading AI model for some at least brief kind of period of time.”
Undated
Aaron Levie, who has worked in tech for twenty years since the start of the cloud, says AI is moving at least five to ten times faster than any earlier wave he has seen.
“Having done this now for twenty years, uh, starting right at the at the start of the cloud, seeing the iPhone, seeing the iPad, this is absolutely the fastest I've ever seen tech move by at least five to ten x.”
Undated
Aaron Levie argues that punitive tariffs above roughly 30% on a country raise the cost of serving an industry and put that country's exports at a competitive disadvantage.
“But take any kind of punitive tariff above, I don't know, 30% on a country. You've now inflated your cost of serving in a particular category or industry.”
Undated
Aaron Levie says his political comments are his own views and not official positions of Box.
“These are not like the box official, like put our logo on it views. These are just Aaron's views about a thing.”
Undated
Aaron Levie says he believes some components of the Department of Government Efficiency made sense.
“I do think that we could spend less money in the government and get more out of it. Some components of Doge, uh, I I've I felt made sense.”
Undated
Aaron Levie says hacking and intellectual property issues in China are big problems, even though he is not deeply afraid of China winning in AI.
“The hacking issues are a huge problem. IP issues in China are a huge problem.”
Undated
Aaron Levie says the Trump administration is biased toward not over-restricting AI, which he credits as an improvement over the Biden administration.
“There's a general bias toward not trying to overly lock down AI, but actually let let AI get more diffuse because you you eventually innovate faster”
Undated
Aaron Levie proposes giving a green card with the diploma to anyone who studies AI or computer science in the US, and says neither the Trump nor the Biden administration did this.
“What you would do is you would just do the whole green card stamped on the diploma, uh, after college, and you would get anybody studying AI in the US.”
Undated
Aaron Levie says cloud computing is twenty years old and its quarterly adoption is still growing at the same rate as before.
“We're twenty years into cloud computing, and and the then the quarterly rate of cloud computing sort of adoption is still growing at the same rates as ever before.”
Undated
Aaron Levie says banks still announce new cloud deployments for systems like trading platforms twenty years into cloud computing.
“When I go to a bank, they'll still say we just deployed cloud for this trading platform. Twenty years, twenty years into this.”
Undated
Bob Safian says he put Aaron Levie on the cover of Fast Company about a decade earlier to represent new leaders embracing adaptability.
“I put Aaron on the cover of Fast Company a decade ago to represent how a generation of new leaders were embracing adaptability.”
Undated
Aaron Levie says that, by every statistic he has seen, Cursor is the fastest-growing software company in history, at least in an enterprise context.
“As far as every stat I've seen, cursor is the fastest growing software company in history, at least in an enterprise context”
Undated
Aaron Levie says deep research tools take about five to ten minutes of thinking time per answer, compared with a few seconds for a typical chatbot reply.
“takes about 5 or 10 minutes of kind of thinking time for these AI models”
Undated
Aaron Levie estimates he had at least 100 customer interactions in the first quarter of the year, with about 80% of AI discussions focused on work the company did not do before.
“I've had at least 100 interactions with customers in in the first quarter of this year. The vast majority, you know, 80%, I'm guessing”
Undated
Aaron Levie gives a hypothetical in which an AI agent reviews 50,000 customer contracts for about $5,000, a task companies would not previously have paid people to do.
“But now, if it only costs them $5,000 for an AI agent to go do that, they would do that all day long.”
Undated
Aaron Levie describes the Duolingo memo as an emerging idea that teams must prove AI cannot do a job before they are given new headcount.
“There's some emerging idea, which is sort of you have to prove that AI can't do this thing for for you to get then headcount.”
Undated
Aaron Levie says Box's approach is the opposite of the Duolingo-style rule: teams that show they can use AI get additional headcount.
“If you can prove that you can use AI, then that's actually when you will get headcount.”
Undated
Aaron Levie says there are arguably five to six companies competing in AI models, any of which may briefly hold the leading model.
“there's arguably 5 to 6 players, all of which you could throw a dart on a dartboard and they will have the leading AI model”
Undated
Aaron Levie says earlier platform contests, such as operating system and device wars, usually had only two to three credible competitors.
“And even then, there's usually only 2 to 3 credible players that that kinda take the attention of the market.”
Undated
Aaron Levie says he has worked in technology for 20 years, beginning at the start of cloud computing and through the iPhone and iPad eras.
“Having done this now for 20 years, uh, starting right at the at the start of the cloud, seeing the iPhone, seeing the iPad”
Undated
Bob Safian put Aaron Levie on the cover of Fast Company about a decade before this interview.
“I put Aaron on the cover of Fast Company a decade ago to represent how a generation of new leaders were embracing adaptability.”
Undated
Aaron Levie argues that a punitive tariff above roughly 30% raises the cost of serving an industry for that country's exporters, which no competitor faces.
“take any kind of punitive tariff above, I don't know, 30% on a country. You've now inflated your cost of serving”
Undated
Aaron Levie proposes giving graduates studying AI or computer science in the U.S. a green card with their diploma, and says neither the Trump nor Biden administration did this.
“What you would do is you would just do the whole green card stamped on the diploma, uh, after college”
Undated
Aaron Levie says cloud computing is about 20 years old and its quarterly adoption rate is still growing at the same pace as before.
“We're 20 years into cloud computing, and and the and the quarterly rate of cloud computing sort of adoption is still growing at the same rates as ever before.”
Undated
Aaron Levie says banks still announce new cloud deployments, for example for trading platforms, 20 years into the cloud era.
“When I go to a bank, they'll still say we just deployed cloud for this trading platform.”
Undated
Aaron Levie estimates that 60 to 80 percent of engineering time goes into necessary work that does not itself differentiate a project.
“maybe sixty, seventy, 80% of of your engineering time is going into the work that doesn't really actually make the the project differentiated per se.”
Undated
Aaron Levie says engineering suits agents because the work is mostly text-based and models are trained on large amounts of code.
“The work is mostly in a text-based medium, so, you know, you're mostly just writing code.”
Undated
Aaron Levie says code is verifiable through regression testing, unlike contracts or financial analyses.
“if I build a bunch of code, uh, and I can go and do a regression test on it, I can see, you know, did I break anything or does it still work?”
Undated
Aaron Levie says engineers already have access to the code base for their project, so the agents they deploy do too, unlike in the wider enterprise.
“if you're an engineer working on a project, you already have access to the entire code base relevant to that project.”
Undated
Aaron Levie warns that organizations relying on security through obscurity can have agents leak data to the wrong people.
“you have too much access to information. Um, and we have sort of, s you know, a security through obscurity, uh, in your organizations, and now all of a sudden the the agent is leaking data, uh, to the wrong people.”
Undated
Aaron Levie argues CEOs are the furthest from real work in a company, which makes them prone to overestimating automation.
“Is like a CEO, by definition, is the furthest away from the real work that's happening in the company.”
Undated
Aaron Levie predicts enterprises will have internal forward-deployed engineers, typically in IT but embedded in lines of business.
“I actually think there's going to be a role for effectively an internal FDE.”
Undated
Aaron Levie predicts that within one to three years the cost of top frontier models and the next-best models will diverge, making model routing important.
“you're going to see this sort of stratification between the cost of frontier intelligence and the cost of sort of the second best frontier intelligence.”
Undated
Aaron Levie says a period of venture-subsidized tokens for coding agents lasted about a year and appears to be ending.
“It was a beautiful moment in history. It lasted about a year, um, and we all had a great time.”
Undated
Aaron Levie says IT budgets typically run about 2 to 5 percent of revenue, which he sees as a cap on AI spending unless business units own budgets.
“IT budgets kind of run at depending on the industry, maybe three, five, you know, you know, two to two to 5% of of sort of total revenue”
Undated
Aaron Levie predicts there could be about a hundred times more agents than people using software.
“we're going to move to a world where there's going to be, you know, maybe a hundred times more agents than people using software.”
Undated
Aaron Levie argues companies should not vibe-code core systems of record such as CRM or ERP.
“we don't think that you should be vibe coding like a core system of record for your documents and enterprise data.”
Undated
Aaron Levie warns that wrong prompts and limits could produce a $50,000 token bill overnight.
“you could probably, like, go and spend 50,000 and wake up the next day and, like, have that bill.”
Undated
Aaron Levie says giving an agent too much context is a security risk and also leads to wrong answers because the agent has too much to attend to.
“You can't actually just shove as much context as possible to the agent.”
Undated
Aaron Levie says agents may be the most technical solution ever deployed to non-technical people, raising the importance of the CIO role.
“agents are are maybe the most technical solution that has ever been deployed to non-technical people.”
Undated
The host says this was Aaron Levie's sixth appearance on CXOTalk.
“This is your sixth time on CXO Talk and and I'm very grateful to you.”
Episodes