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Podcast Episode Notes: 20VC: Box's Aaron Levie on Predictions for the Next Wave of AI
Episode Overview In this episode of The Twenty Minute VC, host Harry Stebbings interviews Aaron Levie, the Co-Founder and CEO of Box, discussing predictions for the future of AI, the evolving landscape of SaaS business models, and the competition between startups and incumbents in the AI space.
Key Guest Information
- Guest: Aaron Levie
- Role: Co-Founder and CEO of Box
- Company Highlights:
- Over $1 billion in annual revenue
- Market cap of $3.85 billion
- Raised over $560 million from notable venture capital firms
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Discussion Topics
- Entering the AI Wave
- Transformative Window in AI: Levie emphasizes that the tech industry is experiencing a pivotal moment akin to previous shifts (PC boom, web boom, mobile boom).
- Success Factors: Founders need to focus on specific use cases that incumbents may overlook.
- AI Adoption: Business Models and Implementation
- Impact on Work: Levie discusses how AI will reshape business processes and operations.
- Obstacles to Adoption: Identifies the biggest challenges facing large organizations in integrating AI.
- Business Model Shifts: The SaaS business model is expected to undergo significant changes due to AI.
- The Next AI Breakthrough: AI Agents
- Emergence of AI Agents: Levie advocates for the belief that AI agents will transform organizational structures by automating processes.
- Differences from RPA: Compared to Robotic Process Automation (RPA), AI agents are seen as having greater intelligence and versatility.
- Startups vs. Incumbents
- Competitive Landscape:
- Startups have an advantage in the application layer, while incumbents hold strong positions with their data and established workflows.
- Incumbents may struggle to innovate quickly due to their existing business models.
- Advice for Startups: Focus on areas where incumbents are not paying attention, especially in niche markets.
- AI and Employment
- Job Displacement Concerns: Levie discusses potential job losses due to AI but believes that many employees will be repurposed to higher-value tasks.
- Future of Work: Organizations will likely reinvest efficiency gains from AI back into their workforce, expanding roles rather than reducing them.
- Regulation and the Future
- Concerns About AI Regulation: Levie expresses less concern about regulation stalling innovation, noting that current discussions are more about refining IP and copyright laws than halting progress.
- The Future of Box
- Goals for the Company: Levie aims for Box to leverage AI to enhance the way businesses manage their data, ultimately setting the stage for significant growth.
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Key Takeaways
- Timing is Crucial: The current window of opportunity for AI innovation is finite; startups must act quickly.
- AI's Role in Business: AI is transitioning from a tool to a core element of organizational structure and processes.
- Market Dynamics: The landscape will see a combination of existing firms adopting AI capabilities while new startups emerge to fill gaps.
- Future Predictions: In five years, expect to see a variety of AI roles in the workforce, transforming traditional job functions.
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Conclusion Aaron Levie provides valuable insights into the AI landscape, emphasizing the need for agility and focus as the market evolves. The discussion highlights the importance of leveraging AI technology not only to enhance productivity but also to redefine how organizations operate in the future.
Listen to the Full Episode For the complete discussion, access the episode on [The Twenty Minute VC](https://www.20vc.com).
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:00Open AI is kind of telling us what they are going to become. ChatGBT is going to be this universal, assistant interaction interface. You probably don't want to do things that instantly could be subsumed by a horizontal chat interface. You have to do the workflows that eventually a human who wants to go and run a full business process has to implement. We are in at one of these moments with AI, which is a period where we are going to see not only breakthrough technology, but the breakthrough application of those technologies. That is as much going to be an incumbents game as a startups game this time around.
0:32You're gonna be working nonstop if you're in one of these companies. Like there is no chance that you should be focused on sort of anything other than just pure survival and execution. This is 20VC with me Harry Stabbings and this show today is a special one. It all starts on Twitter on the weekend with the one and only Aaron Levy sharing some wisdom on the AI landscape today. And I said, hey, let's make a show happen. And just three days later, here we are, recorded, released. For those that do not know, Aaron is one of the OG founders of the last two decades, as the co -founder and CEO of Box.
1:04Today, Box does over $1 billion in annual recurring revenue, with a market cap of $3 .85 billion. Yes, that $3 .8X is something we discuss in the show today, and Aaron has become somewhat of a luminary on Twitter, on the evolution of the AI ecosystem. system if you don't follow him there it really is a must at levy. But before we dive in, I want to talk about Cooley, the global law firm built around startups and venture capital. Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 60 plus years working with VCs.
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3:43You have now arrived at your destination. Aaron, I am so excited for this. I'm like a big fanboy of your tweets. I go downstairs. People don't know this. It makes me sound really sad. I go downstairs for like my evening espresso, which is weird in itself. And I like read your tweets from the day on AI and I'm like, oh, this is a good one. So, thanks. Hi, Robby me. Hi, I'm happy to provide your evening entertainment. I want to start with one of your tweets mentioned, as you're living through the transition to cloud. And I just thought you really had such a front row seat to that. Having the experience that you have in terms of living through that transition, how do you think about what it takes to be successful with this transition in this next wave of AI?
4:23We are clearly in this window that is going to be relatively temporary. I don't know if it'll be two years, I don't know if it'll be five years, I don't know if it's already over. But basically you have these windows more or less once a decade. We had it in the PC boom, basically the 80s. You had it in the web boom in the 90s. You had it in the mobile and cloud booms in the kind of mid -2000s and 2010s. And in each one of these moments, there's an architecture shift that happens in tech that creates really the only window of opportunity you have for new kind of platform scale, large franchise kind of companies to emerge because you need to change in the technology industry for New insurgents to be able to enter where else basically the incumbents will just naturally gobble up all of the market So we are in now one of these moments with AI Which is a period where we are going to see not only breakthrough technology But the breakthrough application of those technologies that is as much going to be an incumbents game as a startup game this time around because the incumbents have a lot of the data and a lot of the workflows.
5:24So it's even more competitive, I think, than the prior periods of these windows. But you will have this moment of opportunity where startups will emerge that will be able to figure out a set of use cases or a way that they should deliver functionality on AI that an incumbent will not be paying attention to, will not maybe go after in these windows where you can build now very large companies. And so we're in one of these windows and it's sort of, these are the only times when you really have that level of clear opportunity in front of you. And so now I was most of the issues I call to, you're going to be working nonstop if you're in one of these companies.
6:00Like there is no chance that you should be on sort of anything other than just pure survival and execution as an organization. Do you think new juggernaut companies will be created both in the foundation model layer and in the application layer or just in the application layer with incumbents gobbling up the foundation model layer? I would say that there will be some foundation model companies, but not nearly the magnitude of the application layer companies. And much of that is due to the trends we've already seen, which is, you know, the moment you have people like Zuckerberg that are literally willing to spend billions and billions of dollars commoditizing the model layer, it becomes very hard to sort of figure out, well, how do you differentiate in that space enough where you won't, you know, going to be taken out by one large training run from an OpenAI or a Google or a Zuck.
6:52There will be like niche or industry specific, you know, sort of approaches you could take or some very, you know, kind of specific domains you could go after. Like I think there could be categories where, you know, maybe the big incumbents are more nervous about going after audio because there's obviously going to be lots of interesting conversations about copyright and whatnot. But I think for like the pure play horizontal LMS, I think those are largely species -sumed by the big players with maybe room for one, two, three independent companies at scale that are not in the hyperscalers, but they'll not be room for 50 companies.
7:26That's just not going to be possible. When you think about, say, like a box today, how do you think about leveraging LLM? Is it a case of actually using six at the same time and switching between them for different use cases and purposes and being able to transition seamlessly between them? How do you think about that and the choice that companies have that? So we are building an architecture that lets our customers do what you just said. So effectively switch between models that they want to use for different purposes. I don't think you're going to have complete commoditization of sort of the personality of the models for the sort of style and the response.
7:57To the point where then, you know, if you're a user, any given response could come from Gemini versus GPT -4 versus, you know, Claude. I think that's probably less practical. You're going to be more wired into a particular model for some use case as a user of software. Well, what we did basically is, as sort of this wave started 18 months ago, we basically started working on an AI platform layer that connects the data inbox securely with any AI model, starting with open AI models. And then over time, we will be opening that up to other AI models as well. So if you're a customer and you say, okay, I really find GPT -4 is very good at legal answers, but Gemini is very good at point metadata from documents.
8:37Those would be two different use cases you would have with AI within Box, and we would give you the ability to interact with multiple AI models to go do that on your content. When it speaks to large enterprises, they will say the same thing. They say, hey, I want to get the incredible benefits from some of these providers. But fuck, it's really sensitive data. I'm not willing to put that anywhere near any vulnerable openness. They don't want to put it in the cloud. It's like we're seeing this reversion back to on -prem in a fear of security issues. How do we solve for that? You know, interestingly, I'm not necessarily seeing that in fact, I'd probably say the opposite.
9:09For the first time ever, we're now talking to customers that have been cloud holdouts that are said that previous to AI they said I'm fine with this data being on prem I feel like it's safer inside of an on -prem environment AI is kind of the final death nail to to that particular approach if your data is not in the cloud or in a cloud ready form I think it's going to be extremely hard for you to get the full value of AI on your information. I had Sam on the show when he was in London and he said that the the biggest kind of rate limiting factor was actually just the rate of model improvement.
9:38When you look at it how do you analyze the race of model improvement. We have our own internal benchmarking that we do. So we compare models using a set of business documents, but the rate of improvement has been truly incredible, just in the past 18 months. What one critical metric for us is basically token window size. We rely heavily on how much data can you give the model and can you get back from the model in a single sort of interaction or inference. And when we started this whole exercise with just GPD, 3 .5, 18 months ago, So the thing that kind of started the chat to BTWave, the token context window was more or less, I think, 4 ,000 tokens.
10:16So you kind of give it like a blog post to analyze in the past week at Google I .O. Sundar announced a 2 million token window model or version of Gemini. So think about that. That's about a 500X improvement in 18 months of how much data you can give the model or get back from the model. And there's just nothing in technology history that grows at 500X every 18 months. It's just never been been seen before. And that is the kind of pace of innovation that we're able to see in AI right now. So does this completely discard Moore's law? Because as you said, we've never seen that before and it's completely atypical compared to previous progressions.
10:52To be fair to maybe like a Moore's law, like religious, you know, Zellett, this is a sort of a different variable than what Moore's law is, which is about the density of your chip or the performance of your chip. So this is more about model algorithms and how we're actually utilizing these models. There's actually a different law which is sort of the GPU performance and I think there's a sort of a you know Gentson almost kind of created a law around this But we have seen faster than Moore's law improvement on GPU performance So the good news is we get a little bit of a reset on you know There's been a lot of talk on hey is Moore's law slowing down and GPUs kind of are giving us that you know Maybe next tailwind of compute performance improvement, which is this you know miracle that that that we now get to deal with But I would say I'm seeing no signs of AI models slow down anything plateau in terms of the innovation curves that we're seeing.
11:41Going through your your tweet. So there was another cool kind of a chapter slash segment. I really want to stick in on which is that AI agents. Yes. Quite do you believe the next big breakthrough in the world of AI is AI agents? You know, it was interesting is last year when six months or so after the emergence of of chat to BT, there is this mad rush for basically everybody sort of believing that the paradigm of software was you would just kind of chat with all of your applications. And so everybody launched these chat interfaces for software. And that was good because you sort of had to have some way to get started in this movement and to see what the use cases were.
12:19If we're really honest about sort of the chat, you know, use case, chat is more of like a UX paradigm shift. It takes, you know, what used to be a graphic, you know, graphic user interface and turns it more into a command line. I'm going to talk to it. But like at the end of the day, you're kind of still accomplishing the same thing with software in a lot of cases. You can get to information faster, but if all we've done is move the user interface to a chat interface, that's sort of not taking advantage of it. Obviously, the full potential of AI. So I think last year, we sort of saw the chat interface, you know, wave where where that was the initial, you know, kind of instinctive of software providers, and then somewhere around middle of last year, tail end of last year, this idea, or at least more established idea of AI agents has begun to emerge, which is instead of sort of talking to AI to get information back, what if we could talk to AI to have it do something for us, and really kind of complete the underlying task that we're actually trying to accomplish, as opposed to just get information to do the task.
13:19Can I ask a stupid question? Is that not what RPA is? We have a large RPA provides. I always thought I was what RPA was. Everything I just said is exactly how you would have pitched RPA for the past decade. Everything I just said doesn't sort of negate the need for what RPA would be in the enterprise. The challenge with RPA is, you know, RPA is relatively frail. It's often sort of like looking at your computer screen and you know, performing some kind of routine actions. Doesn't handle variability very well. doesn't have the level of intelligence that you now have in AI models. So I think RPI actually gives you a little bit of an early preview of what becomes possible when you could apply more general intelligence, maybe not sort of full AGI, but like a general intelligent model to a large number of business tasks.
14:03So the big breakthrough is what if we could go from a world where software is something that you or I use to get our jobs done faster or enables us to do our jobs to where software is something that you or I use to basically farm out work to AI to go do. It's a real shift of how we think about software and the role of information and intelligence in our organization. So the best examples that are emerging now are I could have an AI that is my outbound sales rep or I could have an AI that basically does full testing of my product as a quality assurance engineer or I could have an AI that responds to all my customer support tickets.
14:45So when you think about now an organization that has, you know, effectively AI agents that augment the labor or the people in the organization, they're not co -pilots. They're literally autopilots that are going out and doing work for you. That's a pretty significant revolution in not only the software space, but literally how you'll run a business in the future. How do you think we'll see org structures changes as a result? Obviously I'm a content business and it changes content immensely. How do you think we'll see org structures changes a result? I think org structures somehow seem to stand the test of time on all forms of disruption.
15:17So there's some good books and like go back, I don't know, 80 years at this point, 70 years at this point that basically codified today's org structure, you know, kind of format. And it has survived the test of the internet of remote work. So I think org structure stays the same. I think what happens is you now have the ability to sort of drop AI labor into any part of that org chart. And in fact, in many cases, augment whatever you would normally have had people go do. Now you have AI go and and swap in for people where you need more support. But I heard you on, you know, the the Bill Gurley show, you know, you kind of speak about kind of doing the work and not selling the tool kind of similar to a Sarah Tavall who's kind of sad.
15:55He's actually out of the use of the lesson tool. And I thought, well, you wouldn't have outbound teams if you had an AI tool that was very efficient. And so you all should change immensely. Yeah, sorry, sorry, sorry, sorry, I mean to be very, I mean, yes, at that level of specificity, you might have certain roles that have now turned into AI roles. But you know, the classic example would be let's say customer support. My general view is that you'd have a layer of AI labor that handles the first line of defense on your inbound customer support. That will still eventually escalate to the human side, which okay, I've got to take on the more complicated processes.
16:31Maybe I'm doing things that are a bit more proactive with customers that have, you know, that have signs of issues. Workday might look somewhat similar. There's just now an extra layer of AI that has been added to parts of the work chart. And then similarly, if I have an outbound sales rep, they will generate leads for then the inbound sales rep that has to go and basically pursue these. So what we've done is really kind of just shift the type of work that that team was probably doing previously in most cases. But we can have two customer support wraps, not 10, because we've taken away all the annoying front line stuff, the low hanging fruit that was handled by AI, and then you've just got the complex for a fewer number.
17:07And we've lost the outbound team. So we've gone from like 20 to 2. Yeah, so if this is a question on then total number of people in the organization, I think given it a couple of interesting questions. So if you take a mature company, let's just say, let's say box, basically anywhere within box, if we can make that particular function more productive, so if I can take a sales rep and have them sell 20 % more, or if I could take a customer support rep and have them handle five times more tickets because AIs helping. At least so far empirically, every time that we've done that, we will actually reinvest in that area of the business because there's simply just more work to be done than we've ever had people to be able to go and do.
17:48If I can ensure that an engineer at Box could develop 30 or 50 % more code, we would actually reinvest that productivity gain back into engineering to build even more software. Some companies I think will choose to just reinvest those dollars in that efficiency and even in the customer support case if we can get rid of Some percentage of those frontline customer support tickets We're gonna take that that that the time of those people and have them turn into customer success Where we're gonna actually go and you know reach out to our customers more proactively when they have issues or when we think There's an opportunity to use the product once that's that's sort of one side of the equation Then I think you have an interesting example which is take a company that starts from scratch They have got one employee.
18:26It's the founder. What does that company sort of look like in the future that actually might look like a different company now I would actually argue that they will actually if AI is sort of doing what it's supposed to do I believe that company will actually hire more people over time on a like for like basis because what they would be doing is that one or two Person company would hire the AI outbound sales rep you know software company They'll actually get more leads faster than they would have as an alternative of kind of way they would run the business, they're going to have to now hire sales reps to handle those leads and they will literally be scaling more effectively and probably faster as an organization.
19:02So there's a lot of belief that like, well, you might have these solo companies that become multi -billion dollar companies with just one person or three people and a bunch AI. I think that will be done by virtue of like everything happens in the world multiple times. But like, I think that will be a relatively novel way to run their company. I think most companies would take the AI efficiency gains and then you'll end up hiring the functions that eventually need to be serving all the new growth That you've just developed because of AI many points. I want to talk to you in that one Do you think we're still in the experimental budget phase for enterprises?
19:34We mentioned there about how we can change functions and optimize them Do you think we're still in the experimental budget phase and how all the best and the worst enterprises Engage an adult with AI. I think there's two types of spend happening There's probably the bulk of the dollars that you see in the headlines. I would argue are likely experiments where you'll have some kind of hit rate success rate that happens. And then those experiments graduate into production spend. We just don't have an accurate kind of pygraph yet of what's in the production category versus what's in the experiment category.
20:07It would be probably too generic to say it's all experimental. And it's certainly not accurate that it's all production. The exact sort of split of those two things is sort of hard to diagnose at this point. I've just been on the road. We've done maybe about a dozen or so AI events throughout the US in the past quarter. The vast majority of companies have a meaningful number of AI experiments happening with lots of different areas of their business, lots of different applications. But the vast majority also have areas that are in production already. So unfortunately, it all would get lumped into the same category of AI spend by the time the CFO gets the AI bill, but we are seeing real production and lots of experimentation.
20:46That's really interesting. Is it an AI line item or is it actually a FinTech line item, a HR line item? Is it segregated by the functional tool that it's in or in an AI tool? We're literally seeing both, just simply because of the way that these products get priced or so are so varied. Sometimes it's included in your SaaS spend and sometimes it's like, no, here's your consumption of your AI usage. We mentioned that about kind of selling the work and not the tools and actually how it changes in terms of providing that output. What does that do to business models? Because we're so predicated on seats.
21:17I'm a south master. How happens now? The good news is that everybody is experimenting with every version right now. So we will eventually see where it lands in six or 12 months. I've certainly had conversations with both with customers and then startups also selling customers on every variety. So do you price to what value are you delivering? How much would that workflow have cost you prior to AI? Oh, it's $100 ,000. Well, we'll charge you $50 ,000 for it. That one's tough to scale because everything's bespoke. So let's kind of throw away the value, the kind of bespoke value oriented approach, except for maybe like a palantir or something, it's very, very hard to kind of make that model work.
21:56So eventually you're going to have some unit that we all agree with that you can go off of. So is it sort of a consumption model of what is your unit of volume? Is it customer support tickets? Is it leads that I generate? Is it emails that I write? You know, what to figure that out? On the AI agents' place, then, when we look forward, what do you think it looks like in five years' time? I would imagine I can sort of sufficiently say, hey, AI, generate leads for my business or answer my support tickets or review my contracts or process my invoices if I can do that. Then, realistically, you will have kind of category winners in a large portion of sort of job functions that today exist.
22:34and there'll be AI versions of those functions. This is again one of these windows where 10, 20, 30, 50 companies will get started that were like the window in the mid 2000s where like all of today's SaaS companies basically emerged in like a five year period, essentially. And we'll have that for basically AI jobs where you'll have the AI security engineer, the AI customer support agent, the AI marketer. You know, lots of companies won't work just for the kind of typical reasons, but we will have a landscape of basically labor that you can get from AI. Then there'll be really interesting kind of second and derivative effects, which is, okay, how do you manage AI labor?
23:12Like right now, and you wanna manage lots of software, you implement AACDA or you implement a security tool. Well, this is kind of a crazy world where all of a sudden, I have digital labor from a variety of providers. Do I need some way to kind of organize them, make sure that they can interact well, have guardrails around what they can do? You can almost imagine like a work day for AI. Like, how do I actually organize what all this work is? How do I actually make sure that it's organized well, you know, versus what the humans are doing? Also, lots of incredibly interesting kind of downstream questions in this world that there were only only scratching the service of.
23:46You said we'll see this whole generation of AI versions of each function. To what extent do you think we have that with new players in each of those functions? Versus Gone Sales Loft Outreach at AI and have it as a another product which is integration into existing workflows and is an extension. The cool thing is this, this will be an epic battle of existing incumbents with existing data workflow and customers that will add AI into their platform to deliver a set of services. That will work some percentage of the time and it's almost like hard to know in advance which categories that works better or worse in.
24:23By default, that will work a meaningful portion of time. Like when Facebook needed to get into mobile other than Instagram, they basically could get into every mobile category that they needed to when they chose to do that. Only the categories that they didn't pay attention to, did you sort of see these emerging, you know, new players in the mobile space. Similarly in AI, I think there will be some categories where incumbents have the natural advantage, but then there will be either blind spots that those incumbents don't kind of go after, or there will be things so different from their existing business model in kind of classic innovator's dilemma of fashion that they just don't understand that they have to go after that particular problem.
25:00It looks like it's not like an actual threat or it doesn't seem to be solving the same problem and then all of a sudden overnight you're like, oh, the business is now over because we were disrupted by the AI version of what we do. You know, if you're a customer support company, you might sort of think like, okay, my classic customer buys seats for every customer's rep that's in the business and that's the business model I have. This AI agent thing looks too different from that business model, all of the sudden, and then even when you build and manage the AI agents to do customer support will be different from what the typical customer support software company will be building that all of a sudden you get disrupted three years later and nobody needs customer support software.
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25:39That is not going to happen exactly like that, but that would be the one disruptive of angle that we could see with some of these incumbent categories. It's funny when you said about the incumbent categories adding on those features and kind of having an extension with the distribution benefits that they have already. The one that everyone's shitting themselves about and start up while there's, well, open AI, I'll just do it. And you're fair enough, played, so it's a warranted worry. And just how do you think about, you know, Sam said on the show? Yeah, I do. Well, deem role. So there were some great memes from that interview.
26:10Well, everybody should think Sam for the clarity and transparency of their model. It's actually very good when basically the lead platform player tells you the types of things they're going to go after versus the ecosystem, people should be paying close attention to that and really understanding what that advice means. When you look at their releases last week, you're looking at language learning tutors and going, fuck, did you or Linga have a business anymore? and does language learning actually have an independent category if OpenAI is able to provide such quality? I think there's a heuristic here that that probably works, which is no matter what, I think we agree that OpenAI is kind of telling us what they are going to become, which is ChattuBT is going to be this universal assistant interaction interface.
26:56All the subsequent tools to manage that and interact with different AIs that kind of come together there. And then they're an API business that will be, you know, you can almost just very quickly easily understand. It's going to be audio, video, text, like it's going to do all the formats of information with, you know, kind of complete intelligence on them. So then you're sitting around, you're like, what startup should I go build? You probably don't want to do things that instantly could be subsumed by a horizontal chat interface. And you probably don't want to do things in the model area that might just be one training running will run away on their end of being subsumed by a more superior model.
27:33This is sort of like to me, it's the most exciting part of software. To 80 % of people, it sounds like the most boring part of software, but it's like you have to do the workflows that eventually a human who wants to go and run a full business process has to implement that doesn't want to just do back and forth chatting with a thing. To even to your tutor point, you know, language learning, I don't think chat to BT itself is going to be coming language tutor. I think it'll have the full capability to be a language tutor at the model level and could you prompt it to being a language tutor. Seems plausible, but hard to imagine it follows a multi -year journey with you exactly in the way that Duolingo would maybe do.
28:11But what should Duolingo do? It's probably as quickly as possible adopt whatever open AI is building from a model standpoint and make sure that they are incorporating that into their product. Because what I do tend to see happen way too often is that incumbents will hold on to their own technology way longer than they should because there's some perceived, I have to own something that in practice, the moment that whatever you thought you had to own is inferior to what the rest of the market has access to. You need to drop the inferior thing as quickly as possible and adopt whatever is superior.
28:40Even if it means potentially supporting what you think emotionally is your long -term competitor. What do you think the streets response to that would be if some of the largest public companies to say drop the inferiority problem and set up, fuck it. We're going to adopt open AI's instead because they're models of that. Probably people would like it if Duolingo announced tomorrow that GBD40 is powering their translation engine. That would actually be a positive because it would just be like, oh, this is this very powerful AI that now your user base has access to. And we understand that you're selling a different flavor value proposition than what open AI horizontally is going to sell.
29:18So we think that could be better for your business. But I have no idea. I mean, this is like, it's impossible to give dual and go advice on this on the top. But all I would say is I've seen some people bury their head in the sand being like, no, my custom train model is so good at this one thing. And we don't want to give open AI this particular data or we're going to compete over time with them. It's like, you can wish all of that to be true. But if what they have is better for the product that you're trying to deliver to customers, that is the only way that you're going to survive this. That's I think what a lot of incumbents tend to run into, which is the classic innovator's dilemma challenge that you see.
29:52You've spoken before about the need for just unwavering commitment and speed and working hard on that though because there's a short period of time where winners will be made. That's kind of easy if you're a startup and there's three people in the proverbial garage. It's quite hard when you're a large company like Box and it's like, oh no, no, no, hundreds of people, thousands of people. This is the time again, back to work, proper, proper work, not nine to five. It's how do you galvanize a team to know this is a sprint go? The tweet I sent was not for anybody else other than boxing employees So for us were 2700 or so employees were still enough though that we can literally get on a zoom call And our all hands is like everybody in the company on one call and then we talked through this tragedy What we have to do I think we're in a moment where anybody reading the news in tech understands the kind of period that we're in I don't necessarily know that everybody understands what's on the line.
30:47If your company doesn't make it to the other end of this bridge before everything kind of breaks off, you know, you're out of business in this new world. So that's probably the only alarm that needs to be, you know, kind of set. What's the biggest thing that you've lost with scale? Some people lose speed, some people lose creativity, some people lose innovation. If you were to say, no, I probably lost that. What was something that you lost at scale that you most want to get back? There is a premium when you're a bigger company, which is when you make a decision It needs to be a well thought out decision that you're just gonna press a button and we're gonna go execute and you're gonna Interate and you're gonna learn lots of things because of the work it takes to drive that alignment But it means when you do that you don't want to follow up a week or two weeks later Be like ah just kidding like we got to do this thing when you're a 20 person company You're just getting a room and you're like okay, here's what I think we should do it looks like this It should be priced like this.
31:35Let's go build it let's test it or whatever. And then the whole company is sort of like fully lined up to go do that thing. You find out that it sucks, and you just quickly pivot. And everybody was on the same page that, no, no, we were just, this was just clearly a hypothesis. We don't really know for a fact what's gonna happen. We can just pivot through this. In a big company, that team still exists. But the problem is you have everybody else watching that team saying, please tell us when the thing is exactly the thing, and we're gonna go off and kind of race. You have to kind of find exactly the right moment where you're ready to now expose the working thing to everybody else.
32:09If it's too late, then everybody's going to be like, well, Bozo's what were you doing? And if it's too early, then you're going to have thousands of people go through the sort of like, oh, that didn't work or like, hey, that didn't land. Finding that balance is kind of an interesting thing for anybody on the more product development, sort of side of these kind of companies. I think of Gemini actually as the first round of Gemini, all the massive mistakes that it made. It's probably some version of this manifestation, which is like if it was a 20 person startup They would have put out there everybody would have known okay This didn't this kind of sucks at these things.
32:40Let's go improve it But at a company the scale of Google like there's some team working on it They kind of throw it over the fence and then everybody's like oh my god. What is this thing? It's just because you had a separation of the people working on the whole thing from then the ultimate people that needed to like You know flag the alarm and by then it was too late and and just chaos do you think you go smashed it last week? I do. I think last week, to me, the thing that I think it underscores, that I think, honestly, Cloud Next did as well, is like, you know, Sundar has set a message to the company that AI is the number one most important priority of all things.
33:14It's like 10 times higher than every other level of everything else you're working on. It's going to be like the new way to search. It's going to be the new products in Cloud. It's going to be in workspace. And I think that message, it was very important. It is now very clearly the evidence of it working is now showing up. And I think Google I .O. is merely the another moment of it manifesting that that company has religion now on AI. Would you be a buyer or a seller of Google? I don't buy or sell anything, so I'm generally long Google in an AI era. Are you worried about AI regulation? I said in Europe, we favor a very regulated environment.
33:48We've made our business kind of constraining our residents and then taxing the shit out of anyone who wants access to them and that's been cool to business this model in this continent, as you know. It's cool that they haven't kicked you out for your views on this. I mean, also just for, you know, it's 10, 30 here and I'm working. So I mean, it's like, I literally had a reference school before this and they're like, dude, are you European? And I'm like, yeah, I know. Are you nervous about regulation, preventing progression in AI? I'm increasingly less nervous only because of what we've actually seen these bills sort of come up with.
34:22They don't seem as sort of progress halting as maybe what would have been rumored about a year ago. The scariest moment to me was the Pause AI kind of moment, which was, okay, we need to stop the development of Advanced AI for six months until we kind of figure something out. It was like, guys, like, it's been, let's say, a decade of us all as a community talking about AI. If you think that in an extra six months is all it takes for us to have some kind of alignment on what is the Doomsday AI going to look like, what is sort of dangerous AI, what is less dangerous AI, six months is not going to solve this.
34:55There are very fundamentally different philosophies in the land of AI that are irreconcilable. They will never fit together. It's okay. It's great to have actually a dynamic set of perspectives. They will not be able to ever be fully unified. And so I thought that that was going to really kind of gum up the advancements if, you know, governments started looking at Pauzei and they're like, oh, even the tech community wants us to stop this thing. And that was what I was kind of most nervous about in that period. Since then, if I look at what has legs, what progress has been made, it's often more surgical AI regs.
35:27So, okay, we have to deal with copyrights and data training. We have to deal with IP protection. I think those are important conversations, actually. I think that our IP law did not anticipate a world of AI in the way that we have today. And I think it's a good conversation that is important to solve. There's another conversation of what is the national security issues with super intelligent AI at some point, in the future, how do we want to make sure to protect against that and regulate that? And I sort of like that this is an open conversation that we should be advancing. I, you know, the show has been successful because I specialize in dumb questions.
36:01From the way that you described agents, it was like the next generation of RPA. What happens to prior RPA providers? Does the ZY pass just adopt an agent -based model and actually move away from kind of wrote learning? But what happens? Yeah, I mean, actually, I think being an incumbent RPA vendor is actually a great spot, Because if you already are talking to customers about literally automating business processes and workflows, and there's just a better way to do that, and there's nothing in conflict with their business model. In fact, if anything, actually, they probably were the first to have more of a consumption -oriented model for automation.
36:35So I think you could be very bullish on RPA vendors right now. I do think it means that more players get in and around the space. The thing that will 100 % guaranteed happen, like in five years or now, this will be the most obvious thing of all time. But when you look at like RPA you had to be you know a relatively deep expert in in RPA You had to be like a mid -size or large enterprise or kind of developer oriented, you know kind of individual The total size of the market was basically arbitrarily or artificially held back by just the complexity of the legacy approach So if AI makes a 10 times cheaper faster and easier to automate workflows then it stands the reason that the market will be substantially larger, could be 100 times larger at the end of this whole journey.
37:20So what will happen is the market will get much larger, traditional RPA vendors if they execute should take a good portion of that market, and there's going to be a new set of entrants that will bring automation and intelligence to their platforms that take out parts of the new market that emerges. That's obviously what we're focused on, which is, hey, what about all the parts of the business that you never automated before. If you go to most companies and you say show me where your digital assets are, all your marketing materials, they're going to be like, okay, it's in all these folders inside of my hard drive.
37:49And well, what if you could just go in and ask a question of like show me all of the red dresses and just like instantly came up? Well, that is what you'll now be able to do with AI. What if you go to your contract repository and instead of it being just a bunch of folders with contracts in them, you just say, hey, what contracts are up for renewal next month with this particular clause in it? And instantly you now know So what areas of risk does your business have? So these are things that you just could not have done before that AI now lets us do on top of all of our data. Do you think there's a hard end -to -price consumer behavior shift that they have to go through in order to fundamentally change how they work?
38:23I mean, probably the long pull of all of AI right now is not going to be the technical breakthroughs. It's going to be the implementation and change management on the human side. So I actually tweeted that AI services companies are going to make more revenue than any foundation model providers and then Accenture posted 2 .4 billion in revenue and opening I posted 2 billion in revenue. So how do you think about that? Did you agree with me? Do you literally mean the Accenture type services? I do actually, I mean implementation and education. Services are almost the leading indicator to compute because you need services to implement the thing that then eventually is sort of on autopilot.
39:01So I think I would take the bet on AI services for the next five years unquestionably. the amount of dollars that will go into the change management of systems, the implementation of the technology is going to continue to be massive. On the other hand, the other thing that goes along with that though is a bunch of the AI stack. So the actual GPUs, the data center build out, that as well. At some point though the curve, if AI is as meaningful as I believe it is, and I think so much of tech believes it is, at some point, the actual AI, the software services of AI, the infrastructure services of AI, will eventually exceed the human services on the implementation.
39:39Simply because now once it's in production, you don't need that same change management 10 years later. Like it's just literally running. Like the amount of money we spend today on our cloud infrastructure, vastly exceeds the amount of money we spend maintaining our cloud infrastructure. Versus five years ago when we were first moving more into the cloud, our services were higher than our infrastructure spent. Is that anything that you think we don't spend enough time talking about? Well, there's not enough light shown on in the AI discussion, and that we haven't discussed today. To me, there's just interesting downstream kind of consequences if everything plays out as it should on paper.
40:14So I have asked everybody the idea of what SaaS did was it made it. So I have a friend who has, he sells balloons online. It's actually not a bad business. It's like it makes real money. And he sells balloons online. And I don't think he would have started the business if Shopify didn't exist. The existence of Shopify made it so he could like be like, oh, well, I had this like random idea Let's just say it works It lowered the barrier to then going out and and basically starting a business And I know that Toby has thousands or tens of thousands of these types of stories So if Shopify caused businesses to get started because it lowered the barrier to being able to sell online if AWS Caused applications to get started because I was like, oh, I could just build an app and run it in the cloud I don't have to think about servers anymore.
41:00If Stripe caused businesses to get started, so I don't think about payments anymore, then in a land of AI agents, you can almost similarly be like, well, somebody literally one day could just be like, well, maybe I should start this idea because I've lowered the barrier to, again, getting customers or supporting customers or testing the software. I now have AI labor that can let me now scale my startup idea or whatever. And I think there's an interesting global democratization that could happen where you could be a company based in a place that did not have this type of talent for a business being started.
41:34I don't know which country I should pick on as a made up, you know, kind of country as this problem. But like if you're two or three people in name your random country, does that country have like the SDR sort of infrastructure that got built out in parts of Europe or the US because of the SaaS boom? Probably not. But like now, I go and I can and just like literally like higher in a outbound sales rep, you know, with AI. So think about what is that gonna mean in terms of where companies could create it, how much you can scale up. I think we'll just see a boom in all new ideas begin to emerge. The one thing I really worry about is slightly on the tangent, but when you have anything kind of generous of AI, essentially supply just becomes unlimited, it could be that outbound sales rep and they can send a million messages a day or we could have a podcast logo cover up or podcast themselves, fuck, people don't know this, before our intros, it's not my voice sound because we have thousands and thousands of hours of my channel.
42:28And so my point being though is that value appreciation going to go to zero when suddenly you get a thousand emails a day from outbound sales reps that are all AI. Yeah, I think you will always see this a standard powerlock dynamic. I think if we were having this conversation, imagine having this conversation 20 years ago exactly and being like, wait a second, if the iPhone lets you have any software and Amazon lets you build any software. Aren't we just going to see tens of millions of apps? How will anybody even know what to find or discover? And I don't know, the world magically just kind of figures out this stuff.
43:04Like the things that don't work die off. People don't pay for the outbound emails anymore. The things that do work take off. Creative destruction is an incredible thing that's alive well in the world. Final one. We've talked about regulations. We've talked about model quality. You've tweeted before about the job displacement concern. If that was one thing that did worry you, what would that be? I think we have ways of defending this, but like, you can, it doesn't take like that much imagination to be like, ah, we know one of those like robot dogs with like a gun and a multimodal AI like, wow, wouldn't want that thing running around.
43:35So, I think there are real reasons we should sort of pay attention to some of the more dangerous use cases of AI. I just think we have, in many cases, sufficient legal frameworks for addressing those things. and then for any net new one that we come up with, let's actually have regulation to go and support that. But what I'm less worried about at the moment is probably the more fringe extreme things of the AI sort of self -replicates, jumps over, outside of the data center to another data center, and then self -propegates. And I'm less nervous that that is sort of on the docket of events. So I wanna do a quick file with you.
44:12I love this. I just essentially, I say a statement, you give me your immediate thoughts, that sound okay? We'll see. Which stage of the business did you suck in as a leader most and what did you learn? Definitely delegation. I like to get my hands dirty with all aspects of the business And so it was it was very hard to kind of let go of parts of it to other leaders Can you not micromanage at scale Jensen Wang as told us was 60 dire at reports? I cannot wait until we're a two trillion dollar company and I will be able to I will be able to go back into that mode I'm in a brief period where I have to delegate to keep people happy, but eventually we will be back to that land I think the real lesson is now is you choose the areas that you need to exert that level of involvement So in places like let's say critical areas like AI or end user experience and some product, you know strategy I still kind of revert back to you know early startup self But there are many areas where just honestly either because of the amount of hours that the job takes or just the fact that like like you want to be able to bring on great people that are motivated to go execute, delegation is actually extremely important.
45:19Why do you think Zuck's crushed it so much? In life we're in AI. I mean, in AI specifically. My read on this is you have one of the best entrepreneurs of our time that has basically all of the right underlying resources for AI. So lots of compute, incredible engineers, billions of users, IE lots of data. And I think he is extremely motivated to have a platform that the internet builds on and participates in. And I think AI is sort of his moment to really kind of reestablish the dominance that I think we remember Facebook having in the maybe late 2000s, which was like we were all going to build on the social fabric of the web.
45:59Some of that happened. Some didn't exactly happen as planned. And I think AI is now this moment when actually you can provide a real alternative to more of the relatively closed approaches to AI. and he's sort of set up extremely well to be that kind of counterbalance in this space right now. So I just think it's like all of the stars aligning for his particular both philosophy and resources. You can add anyone to your board, but obviously you don't have them already. Who would you add them? Why them? We had Jensen's speak at Box six years ago and Jen and I was not a thing, but AI was a thing.
46:35So I'd say Jensen having access to, you know, basically the start of the supply chain of AI is such an important perspective on where things are going. I mean, you, you, if you could just look at his invoices to and from TSMC, if we could just see that data, you would kind of know what to go build next. His window into, you know, five or 10 years out in tech is as unparalleled right now. What did you not do with box that you wish you'd done? Everyone has to prioritize. Everyone has strategic decisions on we focus here. What decision did you decide not to do that you wish you had done? Earlier in our journey, I would have focused more on cash flow.
47:11I have become a little bit of religious around cash flow. I think owning your own destiny as a company is important. I think caring about and inspecting every single dollar of spend in the business is very important. In very loose capital environments, it sort of gets forgotten about or people don't really care about it. But actually, I think it helps you build a better business because you apply constraints that forced better decisions, better strategy, better execution. So I would have done that years earlier than when we ultimately focused on cash flow. Even my now for a few years, what's the secret success is like fucking on it, public market CEO, and a happy marriage.
47:48Pretty tough to do. It helps that my wife is equally busy. So I don't get yelled at as much as probably as possible for for my own not busyness. I mean, you just probably all the standard things. You just you carve out the daydates, you have weekends for family time, and then you just ask for forgiveness a lot. Why are you bullish on Apple? I'm bullish on Apple for a variety of reasons, you know, institutionally how the company operates. But there's some meme probably of like, why is Apple not fully in AI yet? First of all, if you look at the most immediate threat that AI poses for for companies, I don't think Apple is is immediately threatened by AI.
48:27Most of my AI usage is on an Apple product that I have often paid money to Apple to be able to use. So like, just like on the most immediate basis, all of my usage of AI is not threatening to anything that Apple does and is purely contributing even more to their platform dominance. But now let's go on the offensive side. So that's sort of on the defensive side. Like you have to first assess, you know, does this new technology hurt a business that I'm in? And I think the answer is largely no for Apple. They're not selling something that AI is sort of directly threatening. Then you flip to the offensive side, which is, does AI help the business that Apple is in?
49:03And I think it's unquestionable that if you could turn this thing into basically a command center, I just say something to AI. And it does a thing in the world. It gets me an answer to a search query, hey, what's a good way to make dinner tonight? whatever you do as a personal side, instantly they'll just do that. And then if it really turns into a thing of like, hey, book me this flight or call this Uber for me or whatever, that's just an infinite amount of new types of transactions that they can facilitate that they are not currently monetizing in any kind of meaningful way. Now, who knows how they actually monetize those things, but I think it turns your phone basically into your task automation engine, this intelligent sort of device.
49:48And so if you have a billion plus people that are using this device for now a new set of things that they never used it before It's all through your interfaces your APIs or your software. I think that put them in a very powerful position So then the only question is like oh well, so why is it taking kind of quote -unquote so long? I would actually argue that any of the any of the kind of quote -unquote either delays or slow down doesn't amount to anything The AI that I was using a year ago is totally different than the AI I'm using today This space is changing so rapidly that it is way better for Apple to enter the moment when they, you know, believe that they've built the right user experience When the technology is sort of stable and when it's high enough quality We will all use with the thing that they launch whenever that point is all they just partner with open air I asked that I suppose it's these toasts be doing it That's my thing is like there's not that's not even an or what why is that an or like what does it matter to you?
50:40What is the underlying engine in Siri? I don't care I want to be able to click my phone, ask a question, get something done. So, I don't even see that as an or. I see that as just a natural sort of technology, partner supply chain thing. And who even knows what they're even doing because it's all rumors. I don't see that as any weakness on Apple's front. I see that as a consumer. I just want the best AI to be on my device. Final one. If I said to you, it's 20, what is it, 2029, why would you be thrilled for box to be then? There's, there's, there's, like metrics like, you know, We just passed a billion in revenue.
51:14We like to get to two billion as quickly as possible That's an important milestone for us at Can I be blunt? Well, I'm so sorry for being so rude you talk billion in revenue your market cap is 3 .89 I'm I like I'm depressed Don't be too depressed. No, but like I was taught like at least like 8x Yeah, I'm a rasta. This is sort of why I am the lesson for everybody's future is eventually, at some future point, you will be measured on a set of metrics that are much more boring than AR multiples, and they will be free cash limit multiples or whatnot. So, we are at the later stage of that journey now.
51:564x is clearly way too undervalued. You should be in the kind of 6 or 8x range. We had a period probably the last couple of years where the kind of core business slowed down and we've been launching a sort of second act as a word or third act within you know both AI Workflow automation more business process that takes time to get to scale before obviously the top line growth You know can slow down so so we're kind of in the midst of that transition right now But these are the things you deal with as a as a public company So why would you be five years then sorry? I interrupt you with no No, no, it's fine.
52:30So our next set of goals, get it to a billion as quickly as possible. Marker cap kind of, you know, whatever is associated with that, you know, I don't have a specific, one specific thing as much as kind of back to what we were talking about earlier on AI. You know, if you think about the information that goes into your content, your contracts, your marketing assets, your financial records, your invoices, this is basically, you know, the closest thing that a company has to its digital memory, let's just say. And AI now has the ability to actually tap into your digital memory as a company. The thing that over the next couple of years, and so let's say five as an arbitrary point, is really enabling just the world to reimagine what they can do with their data.
53:11And what if every company had infinite digital memory to make better decisions, to automate more processes? Think about the new employee that has to be onboarded, that doesn't know anything about what the hell the organization is doing. Instantly, that's now what they can tap into. So, so we think it's just a profound moment for for how you work with your information in the cloud. Listen Aaron, thank you so much for putting up with me pressing in any different areas, which was toad also like there was no schedule send ahead of time. This like arranged on Twitter without the usual process. I'm sure.
53:41Who wants process? So we're going to. But thank you so much. Thank you. I mean, what can I say? I absolutely love doing that show. If you want to watch the full episode, you can watch it on YouTube by searching for The 2020 VC does 20 VC on YouTube, but before we leave you today, I want to talk about Koolie, the global law firm built around startups and venture capital. Since forming the first venture fund in Silicon Valley, Koolie has formed more venture capital funds than any other law firm in the world, with 60 plus years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund's lifetime.
54:18We use them at 20 VC and have loved working with their teams in the US, London and Asia over the last few years. So to learn more about the number one most active law firm representing VC backed companies going public, head over to Coolee .com and also Cooleego .com, Coolees award -winning free legal resource for entrepreneurs and speaking of providing incredible value to your customers. Travel on the expense and never associated with cost savings, but now you can reduce use costs up to 30 % and actually reward your employees. How? Well, the van rewards your employees with personal travel credit every time they save their company money when booking business travel under company policy.
54:59Does that sound too good to be true? Well, the van is so confident you'll move to their game changing all in one travel corporate card and it spends super app that they'll give you $250 in personal travel credit just Thanks for taking a quick demo, check them out now at navan .com -4 -20VC. And finally let's talk about Squarespace. Squarespace is the all -in -one website platform for entrepreneurs to stand out and succeed online. Whether you're just starting out or managing a growing brand, Squarespace makes it easy to create a beautiful website, engage with your audience, and sell anything from products to content, all -in -one place, all on your terms.
55:36What's blown me away is the Squarespace Blueprint AI and SEO tools. It's like crafting your site with a guided system, ensuring it not only reflects your unique style, but also ranks well on search engines, plus their flexible payment options catered to every customer's needs, making transactions smooth and hassle free, and the Squarespace AI? It's a content wizard helping you whip up text that truly resonates with your brand voice. So if you're ready to get started, head to squarespace .com for a free trial, and when When you're ready to launch, go to squarespace .com slash 20vc and use the code 20vc to save 10 % of your first purchase of a website or domain.
56:13As always, I so appreciate all your support and stay tuned for an incredible episode this coming Friday, a compilation where we bring together the best minds in AI to understand where they think true value lies, whether it's in the infrastructure layer with foundation models or in the application layer with start -ups.
From the publisher
Aaron Levie is one of the OG founders of the last two decades as the Co-Founder and CEO of Box. Today, Box does over $1BN in revenue with a market cap of $3.85BN, and has raised over $560 million from the likes of DFJ, Andreesen Horowitz, and Coatue.
In Today’s Episode with Aaron Levie We Discuss:
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What You Need to Know Entering This AI Wave:
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Why does Aaron think we are currently in a transformative window in AI?
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What does Aaron think it takes to be successful in this next wave?
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Which areas does Aaron think founders should be focusing on today? Where should they not?
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AI Adoption: Business Model, Implementation, Regulation.
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How does Aaron think AI will change how we work & run a business?
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What does Aaron think is the single biggest obstacle to AI adoption in large organizations?
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Does Aaron agree with Sarah Tavel @ Benchmark AI companies will be selling work not tools?
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How does Aaron think AI will change the SaaS business model?
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Why is Aaron not as worried about AI regulation? What are his biggest concerns today?
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The Next AI Breakthrough: AI Agents
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Why does Aaron believe the next big breakthrough in AI will be agents?
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How does Aaron think AI agents will change org structures?
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How does Aaron think agents will differ from RPA? How will RPA companies benefit from AI?
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What does Aaron think AI agents will look like in five years?
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Startups vs Incumbents: Who Wins?
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What is Aaron’s advice to startups today building against OpenAI?
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Does Aaron think startups have more advantage in foundational models or the application layer?
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What advantages do incumbents have? What are their biggest weaknesses?
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Who does Aaron think are the biggest winners in AI today? Who is underperforming?
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Why does Aaron think Apple isn’t losing the AI race?




