Ep 159: Aaron Cannon Is Building the Leading AI Customer Research Platform; It's About to Upend a $140B Industry

2 Jul 2026 · 40 min · 22 chapters

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In short

Outset’s AI-moderated research platform replaces low-quality surveys and unscalable one-on-one interviews with AI-led, one-on-one customer interviews that scale “infinitely” while preserving interview depth. Guests argue this will upend a $140B customer research industry by enabling always-on, real-time feedback loops (beyond NPS) and “self-driving research,” potentially integrated with agents that fix product issues.

Guest backgrounds

Aaron Cannon is founder of Outset (backed by 8VC; ~8X revenue growth last year; ~75 employees). He previously built in tech and worked in customer research/insights. Co-founder Michael is a former professional firefighter (built Watch Duty) and applies firefighting systems principles to company operations.

Key claims

AI interviews reduce survey fatigue, capture deeper “ground truth,” and reduce social desirability bias (people share with AI they won’t share with humans). Outset doesn’t replace researchers; it increases researcher leverage and shifts them toward methodology and interpretation.

Notable examples

First production study with Weight Watchers; interviews used by 100+ major companies including Microsoft, Nestle, Google, and Uber. Mentions “expert calls” and NPS limitations; possible integration with “Cognition” to push PRs/agent fixes.

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

Chapters

Tap a time to open that second in VO

Introduction to AI in Research

0:00 to 1:11

Learn about how AI is transforming customer research and insights.

“People actually share things with AI that they won't share with the person.”

Aaron Cannon's Journey to Founding Outset

1:18 to 2:34

Discover Aaron's background and motivation behind starting Outset.

“All right, Aaron, you spent a big chunk of your career as a builder all over the valley before, and you decided to take a big swing and create Outset.”

Building a Company with Unique Partnerships

2:34 to 4:19

Explore the dynamics of complementing skills in founding a tech startup.

“Like there is, you have a certain, like you're naive about the world and that can be really valuable.”

Balancing Optimism and Paranoia in Leadership

4:19 to 4:30

Learn why a balance of optimism and caution is essential for founders.

“Especially if I'm always projecting all this optimism.”

Understanding Outset's AI Moderated Research Tool

4:30 to 6:01

Gain insights into how Outset utilizes AI to enhance customer research.

“But yes, we balance each other in that way.”

The Evolution of Research Methodologies

6:01 to 8:10

Discuss the shift from traditional research methods to AI integration.

“What was actually broken about how companies understood their customers before you came along with Outset?”

Engagement and Honesty in AI Interviews

8:10 to 11:21

Explore how AI facilitates deeper engagement and honest responses in interviews.

“This was obviously not possible until the last few years.”

The Impact of Social Desirability Bias

11:21 to 13:25

Understand how social biases affect research and how AI can mitigate them.

“And Alex Kolesic, a very skeptical Serbian CIO, was like, why would anyone ever talk to a computer extensively?”

Winning Trust from Major Enterprises

13:25 to 14:03

Learn how Outset earns the trust of large companies like Microsoft and Uber.

“So it's a hard thing selling to the giant enterprises.”

Navigating the Speed of Change in Enterprises

14:03 to 14:55

Learn how social pressures and enterprise structures impact AI adoption.

“There is a huge amount of social pressure and people want to keep their jobs.”
Show all 22 chapters

The Role of Human Researchers in AI

14:55 to 16:44

Explore how AI changes the role of human researchers and enhances productivity.

“So if AI is running the interviews, it might sound to some people like you're just replacing people.”

Always-On Customer Insights

16:44 to 17:46

Discover how AI can facilitate continuous understanding of customer needs.

“So we talk a lot internally about productivity improvements and how that's obviously a much better aspirational goal for how AI can help with a lot of these corporate use cases.”

Transforming Corporate Feedback Mechanisms

17:46 to 19:26

Learn about the shift from traditional feedback methods to constant customer engagement.

“So the best always-on understanding of people we have is an NPS program.”

Balancing AI and Human Interaction

19:26 to 20:57

Understand the balance between AI-driven insights and personal relationships in business.

“So I would like, people are all the time mixing.”

Self-Driving Research: The Future of Data Gathering

20:57 to 22:36

Explore the concept of self-driving research and its implications for decision-making.

“I don't know if you ever noticed this about yourself.”

Synthetic Research: The New Frontier

22:36 to 23:58

Delve into the concept of synthetic research and its potential alongside human insights.

“I will still get Jack and other people and I'll be like, I'm the boss signing off on this, even though I've not contributed anything.”

Empowering Researchers Through AI Tools

23:58 to 28:00

Learn how AI tools are designed to empower rather than replace human researchers.

“So I think synthetic research is the idea of simulating someone.”

Company Growth and Culture

28:00 to 29:40

Learn how the company's rapid growth is linked to its strong culture and hiring practices.

“At the end of the day, the researchers are going to be there.”

Onboarding and Employee Integration

29:40 to 31:20

Discover the innovative onboarding process that empowers new employees immediately.

“And I think it is like such a real thing right now and all the debates about 996 and like that to be hardcore, like it's so often contrived.”

Fostering a Collaborative Culture

31:20 to 32:50

Explore how fostering a collaborative culture contributes to team success and morale.

“Like you hire the right people and you put them in place and you let them figure stuff out.”

Transition to Demand Unconstrained Growth

32:50 to 37:40

Understand how the company transitioned from education to meeting high demand for AI-moderated research.

“I thought we were getting a deal, right?”

Future of AI in Research

37:40 to 39:43

Discuss the implications of AI-moderated research for businesses of all sizes and industries.

“We're talking about real use cases and what will look like in the future.”
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Transcript

Automatic transcript. May contain errors.

0:00People actually share things with AI that they won't share with the person. Outset is what we call an AI moderated research tool. The research like underlies everything that we interact with in the world. There are billions of surveys done a year and they are the lowest quality data you could imagine. You can have AI get the depth of that interview, but you can scale it infinitely. It's like such an obvious opportunity to be smarter. I think you ate X revenue last year. This is an insane amount of growth. How did you get Microsoft, Nestle, Google, Uber? This is the killer application for insights and research with AI, period.

0:41Aaron Cannon is a founder at Outset. We backed him at 8VC last year. He grew 8X last year. It's one of the highest growth AI companies we're involved in. This is a really fun one because he's doing things that are only possible now thanks to AI. Over 100 major companies are using him to interview tens of thousands of people to learn more about their product. The world over the next decade is going to change. We're going to have real-time feedback from everyone about how everything should work. It changes how all companies are going to work, not just big ones, but small ones as well. I'm planning on using their product after talking to them here today.

1:09Excited for you guys to learn more. Welcome to American Optimist. Really excited to have Aaron Cannon here, the founder of Outset, and my partner, Jack Moskovich. Jack, thank you for being here too. Thanks for having us. All right, Aaron, you spent a big chunk of your career as a builder all over the valley before, and you decided to take a big swing and create Outset. Why do you do this? Yeah, great question. So I spent a bunch of my career kind of building stuff and being in the industry. I came from the world of research and insights and understanding customers. Then I went on to work at a number of tech companies to build stuff, but I never started my own thing until later.

1:41and uh yeah like there's an archetype in silicon valley that i'm not uh there's the 20 year old kind of naive you know dropout founder type and i'm old compared to that and i think the the uh i waited to start a company until actually i had a kid and that was like a i kind of reset my mentality by my career there was something interesting to me about like you know are you uh working for someone else are you going and doing your own thing in the world and i thought that was really, I don't know, I got reinvigorated by that. And it happened that right as I was having that kind of a mental shift, I, uh, large language models started coming out.

2:17So this was back in 2022. And that's where I, it felt like there was going to be a huge change to everything. And we started kind of, I started thinking about it. So eventually I just, I, I, I took the swing, um, which, which I was just going to like, I think the being the older archetype of founder is like, there are some, you know, obviously there's some upsides of being the younger type. Like there is, you have a certain, like you're naive about the world and that can be really valuable. Uh, at the same time, like having a little bit more experience under my belt, like it also, you know, we sell to the biggest enterprises in the world.

2:49There is something like really helpful about walking into a room and being taken seriously, having credibility, being able to speak to executives when I've sat in their shoes. And so there's a real kind of, advantage to that too. You actually know what they need to know about their customers to get their job done really deeply and you can do it from having done it before. That's right. So how'd you and Michael connect to the side of buildings together? He has a pretty unexpected background of his own firefighting. Yeah, yeah, yeah. So Michael and I worked together at a previous company where I was the VP of product.

3:19He was the tech lead. He was the best engineer at the company. And interestingly, after he left that company, and he had done the fire academy when he was younger. he has really interesting background where he had gotten really passionate about that and so after that company he went off to be a professional firefighter yeah and so he did that I think it was during I think COVID during the worst of the fires so he was doing wildfires that's pretty dangerous actually right? absolutely yeah they have to be really strong he's a lot bigger than me so he's your best engineer and also really fits yeah that's right that's right exactly So if we have to outbuild someone or fight them, we're on the right side.

4:00Michael and I actually work out at the same gym. I thought you said he was the angsty one. He's really strong, though. Both. It's actually both. Turns out you can do both. So Michael is the younger, angsty, always paranoid one. And Aaron gets made fun of a lot for being old. You need someone like that at this startup who is nervous about things. Especially if I'm always projecting all this optimism. You kind of want someone around you saying, here's where it can go wrong. That's right. That's right. I think the job of the founder is to be always paranoid and optimistic. Like you kind of have to be extremely both.

4:32But yes, we balance each other in that way. And no, and Michael, like, I do think also like really people who are really good at one thing are often really good at other things. And that's where like he just was a very good firefighter. He figured out the systems. And then he's actually like a taken a bunch of those principles that he used in the fire service and brings them to how we operate the company today. It's pretty interesting. The cool thing, by the way, that I've observed with the two of you is starting a company with someone you've actually known for a long time is beneficial in weird ways.

5:04And maybe sometimes in unexpected ways where you complement each other in weird ways. You have always been more motivated by what is possible and what could go right. Versus Michael, I actually think, is uniquely a person who is motivated by what could go wrong. And actually having both of those things at the company has been really useful. We learned this in the first year working together that we kept butting heads about like we kept coming into like points of tension because he would frame everything against the negative. We cannot lose this. If we lose this, we're screwed. The fire is going to kill us all.

5:36The fire is going to kill. You're right. The fire is going to kill us all. And so whereas I'm like, you know, we could stop all the future fires. Right. And like, that's exciting. Let's let's run towards that. So anyway, so we started working together. He had also built Watch Duty, which is like the most downloaded app to track fires in California. And so he built that as well. And so he had already brought kind of the software and the firefighting together. So let's start simple. What is Outset? What was actually broken about how companies understood their customers before you came along with Outset?

6:05Yeah. Yeah. Okay. So Outset, I'll start with that. Outset is what we call an AI moderated research tool. So what that means is AI is leading interviews, like actual one-on-one interviews with participants who are your customers, your users, people out in the market that you want to learn from. Right? So traditionally, you basically have to – well, actually, I'll take a bigger step back. Like I think a lot of people in tech don't quite realize how big research is. So you think about like – I'll go all the way back to free market capitalism, right? Is like the whole thing, you have to sell something.

6:39The whole thing is you sell something to someone else. and that's how the whole obviously system operates so the question is how do you know what to sell how do you know how do you know how to meet their needs how do you know how to meet their needs how do you know what their needs are how do you know how to position the thing you have this you know this mug how do you know how to position this to them and say well actually it's really nice because of these reasons like everything around you has been researched right you walk down a grocery store aisle you'll actually see a thousand different like packages every one of those has been tested and those were the winner by the way of 20 other ideas that were tested so basically research like underlies everything that we interact with in the world and so i think it's like a massive massive opportunity but like uh unfortunately the tools have been like pretty rudimentary so uh the tools we've we've had like what's been broken is what we have is surveys which are you know there are billions of surveys done a year and they are the lowest quality data you could imagine these are super annoying people always spam me with these things and i won't do that's right and even if you do you're just trying to get through it right it's like it's not even you don't care It's not people will say the voice of the user.

7:40It's not really the voice of anybody. It's just somebody clicking a button. And the alternative is you actually call people up one by one. Right. And that is actually where the most the deepest, most thoughtful, most like powerful insights are. But, you know, you have 24 hours in the day and you're one person. It's not very scalable. No, it's like zero scalable, right? So ultimately, if you can have AI get the depth of that interview, but you can scale it infinitely, you wind up in a much more like, it's like such an obvious opportunity to be smarter. This was obviously not possible until the last few years.

8:13And it's probably even more possible today than it was a couple of years ago. Exactly, exactly. So, you know, we built our prototype on, I think it was on DaVinci, right? Which is the earliest model of GPT. And like, it kind of worked. but of course it was very rudimentary. Now it's like video and screen sharing and multimodality and there's all sorts of awesome things it can do now. But yeah, the why now for this is just it was not possible and now it very much is. I think there is two cool things we talked about during the race. One is we obviously asked the why now question and the why nows on this were pretty obvious and as obvious as we've seen in a long time which is computers can now talk to people and computers can also process large amounts of unstructured information and actually without either of those things, you're still going to be bottlenecked by human time of either going and talking to the people or reviewing what they said.

9:03And then the other cool thing was, in many ways, all of us companies we work with solve some fundamental trade-off in their industry. In this case, you either had large-scale surveys, which were low fidelity, or manual interviews, which were lower scale but higher fidelity. And now that you can have computers talk to people, you can have the scale of the survey with the fidelity of the manual interview. And I'll just add to that. So I started my career doing the low scale, high depth, extremely repetitive work. I mean, we used to I would run an interview. I would then and then, of course, I'd be one on one 90 minutes.

9:42Right. I could do a couple a day. I do a handful a week. It would take two months, three months to do a project. And every transcript I read four times. There was a system we had. Right. You then put Post-it notes on the wall. Everything was manual. That sounds really annoying. Yeah, it was really annoying. The interview itself was actually pretty fun, but everything else around it is extremely difficult. And then we'd be delivering this to some Fortune 500 company that would have to make multi-billion dollar decisions based on me reading the transcript four times and pulling out some good clips and notes.

10:12And that is a hard thing to do. And they're doing it, right? It still happens today. How do you get someone to talk to an AI for a long period of time? It just sounds like a cute girl or something who's interested in them. No, seriously. Are there tricks to this? What do you do? You pay them. But can you make it less boring or less arduous somehow? It's actually – yeah. So obviously paying people is part of research. That's a very common thing. But the reality is this has much lower fatigue rates than surveys. So meaning that people will go for an hour and they won't drop off. And the reason is like it listens to you and it plays back what you're saying.

10:53And the same way like if we were talking and like you didn't nod or listen to anything I say or play it back and you just asked, you know, just deterministic questions. And I know like it'd be really hard. So it makes it a conversation where it's actually you the same way a person would is engaged. That's right. And the really interesting thing about this is that not only does this scale and get this kind of economies of scale that we talk about, but people actually share things with AI that they won't share with the person. It was one of the most unintuitive things when we were talking for the first time.

11:25And Alex Kolesic, a very skeptical Serbian CIO, was like, why would anyone ever talk to a computer extensively? and then you kind of experience it and the realization is like oh people actually really like sharing their opinions but they want to make sure they're not just going into the ether they want to make sure they're actually captured so they know the ai is gonna be better at capturing exactly but it's even more than that there is a uh there's the idea around like social desirability bias so it's the bias of like i'm gonna share something in a way that like i want you to receive me in that way right like yeah like i want to be seen as a person that fill Yeah, not a jerk that's positive on something.

12:04That's right. That's right. It was made famous by a lot of political polling that there was a huge skew. I forget what year it was. Everyone will not admit they're voting for Donald Trump in certain contexts. Things like that. Exactly. Exactly. That people want to be seen as someone who votes for Obama even if they don't. And that was a huge kind of polling error. And that is a microcosm of the reality in research is that when you're talking to someone, they want to impress you. They want to look a certain way. so our first uh like our first study ever our first customer ever our first study ever like in in production was with weight watchers and that was really interesting because you're asking people about their weight loss journey oh so they're gonna be more honest the computer exactly and like weight watchers really cares about this like it was their growth efforts that were it was for their growth efforts and of course if you're marketing to somebody like you want to tap into the emotional drivers and like if you know you ask the first question they i want to be healthy It's like, okay, but like, why is that important to you?

12:55And before you know it, people are talking about how they want to live long enough to see their grandkids graduate high school. And you can immediately imagine the commercial you'd build around that. You know, we have a weird version of this in investing where our research is called expert calls. And we run into this all the time where you're talking to this expert who's actually being paid money to teach you something about a product or an industry. And you have to drill down like five different times to actually get to the truth. Because frequently they'll be like, oh yeah, and I can pay for this.

13:22and then you'll ask them like five more times and you're like but can you really and they're like okay fine it's actually my boss's boss who can pay for this right yeah i thought so that's right that's right and why would people use us for expert interviews too right like there there is a uh a huge advantage it's almost like we've we fixed the trade-off and there is an advantage of getting closer to ground truth at all times how did you get like microsoft nestle google uber like how these are huge companies they've done this a lot like why do they trust you to work with you Yeah. So it's a hard thing selling to the giant enterprises.

13:52Like there's basically, there's both like headwinds and tailwinds into approaching them. So I think there's a, like right now, obviously the technology is moving extremely fast. Humans are moving reasonably fast, right? There is a huge amount of social pressure and people want to keep their jobs. There's a lot of that. And then enterprises move slowly. And so you're dealing with all three speeds at the same time. um it is so so ultimately like what we what we do is like we try to sell very um it's very like consultative where you're we recognize that we're not just replacing something right we're not taking a thing you're doing and just replacing it you're adding something they couldn't have had us that's right that's right which means it's a new behavior and if you're selling a new behavior it's actually a much more complex thing right we actually have an idea of forward deployed researchers at our company we are forward deploying people who are experts that are professional researchers you're Teaching them how to do this you couldn't do before.

14:45That's right. That's right. And the reality is just it is really hard to take a huge division of Microsoft or, you know, the entire team at Uber and like change the way we understand customers. So explain it. So if AI is running the interviews, it might sound to some people like you're just replacing people. Like what's the remaining job for the human researcher? Yeah. Are you even are you creating more jobs in some cases for them to do? Like explain this. Yeah. So I think it's easy to think about this as an automation play. Right. But it very much is not like we have not seen that the case. So like to draw an analogy, kind of an opposite analogy, with customer support, you have a static amount of demand, right?

15:20You have the tickets you get and you're automating N percent of them and you want that to be as high as possible. And that's going to probably cut people. And that's just reducing cost and you make the money on the margin. I think in the other case, like what we're in is there's not static demand. In fact, demand has been pushed down because of the tools that we have. So if we bend the economic curve, we could do more. So if one person they hire can now use you to do a thousand interviews, then each person they hire might even be worth more for some reason. Exactly right. Yeah, yeah. So each person is infinitely more valuable.

15:50And the other thing is like if research, if you can do enough research to drive a meaningful change in sales, let's just say, just to use direct revenue. If you do the right research, figure out the right thing, build the right product and sell it and drive more revenue, you'll invest more money into that research, right? Because that's just a growth engine. It's a growth driver, not a cost center. And so what we see is that future of researchers is certainly different. They're not doing as much of the pure execution. But we kind of see the barbell where they're either playing a big role in infrastructure.

16:19They're laying the pipes for the entire company to be much more in tune with customers, to be listening much better. And on the other end, they are the experts. They're the methodologists that can actually interpret data in a really, really good way. So how does this change the corporate world's relationship with its customers? Because you have this always on dynamic thing now, I guess. You're going to be always hearing how your customers' needs and wants are changing. Because I'd imagine the surveys one year could be very different than a year or two from now in certain categories. What's that look like in the future?

16:51So we talk a lot internally about productivity improvements and how that's obviously a much better aspirational goal for how AI can help with a lot of these corporate use cases. and I think one of the really cool things observing you and the company has been you can almost start asking these like sci-fi-ish questions every company wants to talk to every customer all the time but it wasn't economical and now you can ask the question well what if you could do that well you probably don't want to talk to every customer it'd be too annoying for sure until they're in the way yes yes at the limit yeah at the limit right and like You want to know what they're thinking, I guess, all the time.

17:33That's true. And you can. And that's really cool. And I do think it changes how companies fundamentally operate a lot, actually. Just to paint the picture of how silly the current universe is. So the best always-on understanding of people we have is an NPS program. Exactly. We all use Net Promoter Scores. And it's like nobody likes it. Well, that's not true. Some people like it. But most people don't like it, and yet they are stuck with it. And all that's happening is you're asking somebody a forced choice of 10 numbers and pick one. And then you're pulling that together, building a DEX, giving it to an exec.

18:08They say change something and you go to it's like the most manual and also extremely like low value data. Right. Each person. And so so it's it is like what what it should be is a constant on the constant listening to customers. Right. So a AI moderator talking to everybody that they can. right all the time always on you should know the moment something's going wrong in your business or your product you should not not just know something's wrong you should know like why and what happened and what's the product experience and you have videos of people talking about showing you their lives showing you what they're doing wrong like so you should have this loop all the way to the to the to the point where like uh we should then not only tell you what's wrong but start fixing it for you right so let's let's give an example here because this made me think of something so at a par for example a company i started there's like 1500 firms on some are very big banks big ra some smaller family offices and they're constantly 15 years old they put billions of dollars in the product it's the number one in the market but they're constantly trying to like optimize because there's like infinite demands for different types of things for them to do and in some cases i imagine it feels like they'd want like the people to have the relationship where they're hearing from them because they want a relationship with a person because that's a really important valuable relationship for us but then in other cases there's probably lots of people we're not getting that we could be getting what parts people do what parts the computer do how do you think about this yeah yeah it's um what when people say people often ask me to like judge my credibility they're like when do i not use a i moderated right it's like uh they're testing me like when a buyer will ask that the answer is like if you are want to have a relationship with that person then have a relationship with that person right don't like put ai between you and somebody you want to have a relationship with so like a hundred percent but the question is like what is the kind of cadence at which you want to have relationship and what is the cadence at which you want to understand more.

19:53So I would like, people are all the time mixing. I'm going to have a couple of interviews with people who are like, they'll call it like a red carpet research, right? When you're really talking to somebody with deep relationship and then the rest of the year, you're sending them AI interviews, right? It's, but like, of course, like there's, there's a mixture that like ultimately needs to happen. But the other thing is like, and these are stuff we're working on is you should take that interview with them and then be able to like, that should help, without that help inform what else you should be asking them from AI and even start informing a simulated version of that person to start asking.

20:26I imagine some of these firms, just to do the Adapar example, might have like a thousand people in it and there might be people in the back office we would never talk to that have like certain things they love and certain pet peeves or something like that, right? You probably could talk to people you never talked to before. That's right, exactly right. It's like some amount of common sense is you're not going to be using this to go and talk to the CIO of a firm who is directly responsible for procuring the product. However, there's probably like 50 other stakeholders in that account who might actually want their, their, to be heard because they're using it.

20:56You know, the other interesting thing, by the way, is we live in such a high velocity world. I don't know if you ever noticed this about yourself. Like I'm increasingly more and more upset if a digital thing I'm using is broken and doesn't quite work the way it should. And I expected it to be fixed really fast. This directly is a function of that. You know, we joke that, you know, maybe by the end of the year, the thing that's possible is you see some NPS score go down, you go interview people with the AI moderated researcher, you synthesize the data, you put together a presentation, and then those tickets go into something like cognition, which actually just goes and compute.

21:35That's hilarious, yeah. So the cognition agent goes and like, fixes the thing that's like, Like, maybe a person slides off, yes, go fix that. And then it just does it. So there's two directions here. Like, one direction is, you know, we gather data. And instead of doing that whole loop you just described, we literally just, like, push a PR to cognition and say, like, or a request or prompt cognition to say, go fix this thing. The other version is that you tell cognition to do something, and it hits outset as a research agent to go learn stuff. Double check. That's even higher level. So the AI could be using you to figure something out.

22:07and then coming back to the human, ideally for now, I have you in the loop for now, and saying, I think this is what we want to do. That's right. For now, at least I want to sign off on these things. Eventually, they might run the world, but for now, I think you need to do it. That's right, that's right. It's this whole kind of idea that we're building is self-driving research, right? It's the idea that research should not actually have to be constantly pointed by humans. Humans are critical in the loop, right? Like, we are decision makers. We have judgments. Similar to a boss at a VC fund, we like to think we're critical.

22:34So even long past the time we are, I will still get Jack and other people and I'll be like, I'm the boss signing off on this, even though I've not contributed anything. I'm sure you add some value here. Every once in a while. But you have to pretend that I do. I'm going to not comment on this. Yeah, you can't comment. Okay, the funny thing is, so we've had a couple of APC build companies use the product to do really early research before they start building. Exactly. That's cool. And the CEO obviously is responsible for all the decisions. Yeah. But now they're going to be making decisions with access to information from a thousand people.

23:10A product went out and reached. I'm probably joking about that. I do think people are going to be in a live long. There will be certain circumstances where the AI maybe. I think humans just play a very different role, right? Like we do not need to be doing nearly the manual work I did in my career. No, we can all be the boss like me. We should all take credit for all the work that is being done by all these smart agents like Jack. I want to go back to something you started talking about, which is this notion of, okay, we've gone out and we've interviewed a bunch of people. And now we actually have some amount of information on what people think on different concepts and topics.

23:48And a very hot, buzzy thing in the venture community recently has been this notion of synthetic research. Talk a little bit about that and your thoughts there. Yeah, okay. So I think synthetic research is the idea of simulating someone. And so if you can simulate someone effectively, you can ask them questions and do research without talking to a person. And my take is like, I think there's it is. I don't know if it's overhyped, but it is definitely going to be a kind of side by side with human research. Like humans are extremely weird creatures and we evolve quickly and we change our minds and there's things that are hot and not hot.

24:24I think the best application of synthetic is to do it hand-in-hand with human, where you can do human research that builds this synthetic picture of someone. So what we use are digital twins, right? The idea of like, I have a digital twin of Jack. Like I did two hours of AI moderated with him. I now understand him enough that I could ask the digital twin questions. That's dangerous. I mean, is this really going to work all the time? It's not, right? So here's the thing. And so the more you do the digital twin work, the more it tells you, we don't know stuff, go talk to the real Jack. And so there's a virtuous cycle where I can, rather than having to call up Jack every week to get the latest.

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25:02I'm suspicious. I'm suspicious because there's a lot of things that you're just modeling what you think the answer is based on things he said. You might actually assume he likes things because he's always liked things before. But actually he doesn't like this, but now you're not getting that. No, I definitely agree, which is why you have to do both together. That's the key part. And I think a lot of people are very excited about doing – imagine like don't even call it research like you're bouncing an idea off of someone right it's early research pre-research is what they'll call it or or it's a echo so i do a big study and i want to just get like can i you know get an interpret or or um infer like from the concept he liked would would he really like this again so it could give you so it can give you some ways of thinking about things and iterating on it it's because i it feels like the human brain we're not really close to mapping out all this stuff no no but but we do like the more we know about somebody there are simple questions we can get get a pretty good answer i guess this is a quantifiable thing you just say what percent times are you right about like a bunch of new questions and you can just quantify this and you know but are you doing that now are you trying to like say okay here's the actual interview but but we already talked to him six times and our here's what we thought the interview was going to be and we got 80 of it right here's the here's what we're building and and the model that that uh i'm most excited about there are others doing kind of let's just say, scraping public data and just saying, hey, I can predict what someone says.

26:20I'm terrified they're going to do this about me because I have way too much content online. They're going to model me. And what if it's right? Then you don't even need me to sign off. You just need the AI to sign off and I can go hang out with my kids. Right, exactly. I think the most interesting way is rather than taking publicly available data, instead have a digital twin model where your digital twin could answer a question and then actually you could have Jack validate his digital twin's answer every third time it's just super creepy someone has built these models of me have you seen these things it's really weird they send them to me and it's them having a conversation with me and it's like kind of annoying to listen to yourself already but it's even more annoying if it's like the computer copying all of your weird ways of talking it's very creepy it's definitely weird to the point where like i think so for outset like our role is to be the front door to the customer understanding yeah and not be we're not that right like like yeah we're not what you just described.

27:16We're the front door to customer understanding and synthetics is a tool to help bring you different kinds of data, more data. It's one of the new tools to get more data, more nuance, but you're going to complement it always right now with the real... Exactly. But if you can't start modeling certain things for them, that's just going to be useful to save time. Exactly. Exactly. To go back, I think the core point here, and you've been very opinionated about this since you started the company, is your job is to empower the researcher. Your job is to not replace the researcher and your job is not to replace the human.

27:43Your job is to understand the customer or help your customer understand their customers the best. You started with an AI moderated user interviewer. And if it just so happens that in some cases you're going to be best off running something by a simulated version, so be it. At the end of the day, the researchers are going to be there. The people are going to be there. That's the actual customer. And they're always going to be in there. Yeah, you're going to have thousands of customers you're paying. They're going to have other ones that are synthetic. For some cases, you guys have proved it's useful.

28:11But let's talk about the company just a little bit more. I think you 8X revenue last year. So this is this AI world stuff is just like, I guess that's normal in San Francisco in 2025. But it's very impressive. I don't think I, you know, previously 8X things when I was building my companies when I was younger. And you've made something like 60 hires, I think two or three dozen in the last few months. Like, tell us about the growth of the company. Yeah. So, yeah, we 8X last year. The trajectory continues to be exponential, which is obviously an insane experience, right? Like we've grown the team.

28:43I think we're now about 75 people. We started the year, I think, at 40. So already just this year, we've almost doubled. So this is an insane amount of growth. And at the same time, we've like the most important thing of a company. I read this article on X the other day of like the last moat is culture. The last moat is people. It's true. It is ultimately the most compounding advantage you have, right? The better people you get, the better people they hire, et cetera. and that you just are executing better. How are you keeping the bar high? What are you doing? So then ultimately, we are obsessed with candidate experience.

29:16So my co-founder and I will meet every single person. There's nobody new that we don't meet. So to some degree, trusting that he and I have the most effective judgment. And we also, as a result, we have a more than 80 % acceptance rate of our offers. And these include, we've beaten labs with multi-million dollar packages. like we are we are beating them uh uh uh like for these jobs for engineer jobs for for go-to-market folks um we've had zero regrettable churn of the company since starting wow um so we're like we're obsessed with candidate experience and also obsessed with culture and i think one of my um my like my missions in life is to prove that you can be an incredibly intense incredibly ambitious and a very effective company and not be asses.

30:04And I think it is like such a real thing right now and all the debates about 996 and like that to be hardcore, like it's so often contrived. And like people work hard, like the best people work hard because they care a lot, not because somebody's telling them to. And like, so all we have to do is hire people, treat them like adults and we don't have to like create urgency. Urgency is here. Like the market is moving fast. Like we have a ridiculous opportunity right now. And so as long as we share that and we have people in it with us with skin in the game, like they're going to operate with that level of intensity.

30:40Give us an example on the culture. How do you onboard someone? You're adding people while you're accelerating. How are you like making sure they come in and they're part of however you're doing it? Yeah. So when people start, I guess a couple of things. When people start, they always build and run their own studies. First thing they do. Yep. Right. They have to use it. They may not be a researcher or anything close to a researcher. They should learn how to do it. They got to do it. Right. The other thing is, like, we just give them the responsibility of the job right away. And don't we don't have a month long onboarding process.

31:10We don't have giant sessions that you have to sit through on day one. Like you make it through security training and now you're doing the job. And I think that, like, again, you hired the right people who can operate like adults and not have to be told what to do. Right. Like you hire the right people and you put them in place and you let them figure stuff out. and it like it goes just really well and like people are like people are supportive like one of one of our like one of our values is that we win together not against each other which is like it is really easy to get a very kind of adversarial culture where everybody's kind of jockeying for position to win and it's like it's pretty simple like we all clearly all win together can we build run studies together we should be doing this ourselves for sure i want to i want to go through that can i go there i think we do it for our listeners we get like talk to a bunch of our listeners and they could all tell me what they're annoyed about exactly and then and then maybe do do it for like you just you don't know something else too we didn't even touch on this but for our ceos exactly but the experience of setting up a study is actually really cool now where you can give it an objective it'll suggest a set of questions i love the ai's gotten so good at this no it's so it's so ridiculously good and and it will uh not only build it out for you but it'll ask you follow-up questions so it'll like it's like what are you really trying to get at is it more A, B, or C.

32:26And it'll actually give you And you've trained it how to do what you would do there. Exactly. And we have a whole best practices library that's a skill that the agent's hitting constantly. So it's really cool. I want to do this for our listeners. I want to do this for our CEOs at the firm. And maybe I'll even do this for our LPs. 100%. I think it'll be super interesting. Let's do a few together. And then it's obviously an opt-in. And then they get to see our technology and then maybe we'll show it online in the process. Let's do this. This is a sales call, it turns out. Let's do it. I thought we were getting a deal, right?

32:54See? No, no, no, no discounts. No discounts. Okay. To go back to the culture thing briefly, because I do think, you know, we had the board meeting a couple of weeks ago, and this is one of the sort of strongest impressions I came away with. One is we started the conversation with talking how you're going to solve the tradeoff between the scale of surveys and the fidelity of manual interviews. I think like clearly solving trade-offs is a thing that you really care about because your company is truly the first example I have seen to the extent to which you've done it that has just solved the trade-off between high intensity culture and people liking their job.

33:33Like both can coexist and it's so rare, but actually it can happen. And then two, typically, you know, we work with all these companies that are growing extremely fast and they're hiring a lot of people really quickly. And usually the thing that happens is the more people you hire that quickly, the more things slow down inevitably. You are genuinely the first team I've worked with that has actually accelerated as it relates to the velocity at which things at the company are happening as you have added more people, which I've genuinely never seen before. The other push that we constantly have, like Michael and I are absolutely allergic to overhead.

34:11So anything that feels like overhead, some overhead is needed, right? Like we need to like figure, you know, we need to be tracking things, right? Like there is overhead, but like every bit of overhead is highly scrutinized by us. Everybody is building, selling, right? Building, selling, supporting. Like that is, that's the business. That's the pure business. Keep everyone close to the substance that matters. Exactly, exactly. And so like, you know, we, for example, we've got, you know, more than 25 engineers, like historically you put them into pods and those pods are very structured and they're focused on different things.

34:39and they're like suddenly you've got this kind of like bureaucratic overhead we're like well which pod and who's leading the and like we don't do that right it's like we have the projects that matter for the next two weeks and people swarm to it you have someone setting up the desks and the shit chairs and ordering yeah exactly someone is doing well there is some overhead in running a company but but it's like everything that's overhead to be scrutinized not just from a financial perspective but actually from an operational one where overhead slows everybody down. I love it. I want to go back to one last thing, which we started talking about and sort of moved on really quickly.

35:14We talked about how you had some of the biggest companies in the world working with you, even when we were investing 18 months ago and you were a relatively small company. And you talked about this notion of being almost like a partner to your customers that are helping them navigate this new AI world and teaching them what AI-moderated research actually is. And then I think, correct me if I'm wrong, since then, in the last 18 months, the market has really tipped. And actually now, every large company in the world and every large research team in the world knows what AI-moderated research is and want it.

35:52And we're almost operating in this entirely demand-unconstrained way. So maybe just talk a little bit about what it's been like going through that transition and running it first in a world where you have to teach people what you're doing. And now actually everyone wants the thing that's this well-defined concept. You've got a wave that they're all pulling. Well, we'd like to think we created the wave, right? Even better. So we basically, we started, yeah, when we started, it was entirely educational, right? Every call was like, what is this thing, right? And I was educating what's possible. There were calls I joined where they did not know what LLMs were, right?

36:29Or they did not really, they were like, oh, I've heard of ChatGPT, is this like that? Or they would say, are you using ChatGPT? I'm like, ChatGPT is a product. Like, what are we talking about here? But like, that was our job. And I was doing all of those calls. I was like, and it was like, the beginning was tough because we were in category creation mode, right? Where we have to wheel this thing into existence. It is not existing yet and it has to exist. So once we figured out, we did that Weight Watchers study, we're like, this is real. This is a real thing. we had to start pulling the industry forward or pushing it forward.

37:00And so that was the hard part. Ultimately, yes, I think in the last 12 to 18 months, the market tipped where it went from this default skepticism and default kind of need of education to, oh, this is the killer application for insights and research with AI, period. This is the killer application. It's so obvious, as we've already talked about. It's the killer application. So the market tipped and now you have and the big research budgets are all the big companies. And so now it's about us investing in to the, you know, the boulder rolling downhill. Right. And so I think that's a yeah. I mean, so now I get on a sales call.

37:41It's a very different discussion. Right. We're talking about real use cases and what will look like in the future. Talk about how do we enable a thousand people to use this product? Not like two people. Right. It's become a kind of organizational question. not a, you know, cool widget question. And I think that's a big difference. And it sounds like a lot more people should be using this even for their small business or whatnot because if you learn about your customers, you could do better, which is why I'm saying we actually probably ourselves even should be using this. It's becoming more of a, I imagine it's going to become a default thing, not just the big companies, right?

38:12That's right. This should, this is a, research is agnostic to industry and to size. It powers capitalism. Like it is, it should be everywhere and we should all be much more in tune. I love it. Thank you very much for joining us. This is awesome. Jack, any final words? No, I honestly watching you guys over the last 18 months has been awesome. And we talked about this a lot. Like this rate of growth used to be sort of a sci-fi thing. Now it's becoming normal. But I think the way you guys are doing it is the most admirable about it at all. And it's just been really cool. And I guess I'll leave you on the question we like to ask.

38:47Like we started American Optimist to push back on a lot of nihilism and cynicism and negativity. uh what makes you optimistic for the next decade in america yeah it's um so so when i think about what is possible if you actually understood what people needed right think about patient experience i like this one it's like patient experience at a hospital it sucks right like we all know it hospital administrators know it right but it's it is so hard to understand why what so i just like i like the idea for my kid right like when he's older that like you know He doesn't get frustrated like Jack does when a digital thing just doesn't work the way it should.

39:24Things are really in tune with people. And it goes well beyond products that you buy, literal experiences, health care, or just education. The things that matter in the world should be just better. And we can help make that happen. Sounds like a pretty awesome world. Thanks, Aaron. Thank you so much. See you guys.

From the publisher

Aaron Cannon is applying AI to solve one of the oldest and most important challenges in business: understanding exactly what customers want and need. Traditional consumer surveys often provide low-quality data, while one-on-one interviews are cost-prohibitive and not scalable. But AI unlocks profound new possibilities. How is Aaron using AI to conduct deep, insightful interactions at scale? What happens when organizations have always-on customer understanding? And what are the new opportunities for incorporating real-time feedback into product improvements?

Aaron Cannon is the co-founder and CEO of Outset, one of the fastest-growing, agent-led customer research platforms. Try it yourself here and help us improve American Optimist; we'll incorporate the top recommendations!

Prior, Aaron was the head of product at Untapped and Triplebyte and worked in senior product roles at Tesla, Pebble, and Monitor Deloitte. He launched Outset in 2022 after seeing an opportunity with large language models to fundamentally change how organizations learn from the people they serve. For this conversation, we're also joined by 8VC Partner Jack Moshkovich, who helped lead our investment in Outset.

We begin with Aaron’s path to founding Outset and the inefficiencies he saw in traditional customer research. Next, we explore how Outset’s AI-moderated interviews work in practice — from consumer studies to enterprise deployments at Microsoft, Google, and Uber. Learn how AI-led interviews can actually elicit more honest and in-depth responses than human-led conversations. Then, we dive into the explosive growth of the company — 8X revenue over the past year — and its “forward-deployed researchers" model. Finally, Aaron shares his vision for "self-driving research": AI that doesn’t just gather feedback but helps close the loop by identifying problems and even suggesting fixes — ultimately leading to improved products, experiences, and organizations.

00:00 Episode intro

01:10 Aaron’s entrepreneurial journey

06:00 How does AI-moderated research work?

09:25 Why people will talk to AI more than humans

13:40 How Outset landed Microsoft, Google & Uber

14:55 Are you replacing human jobs?

20:56 New possibilities for real-time product improvements

23:30 The pros and cons of synthetic research

28:00 Insane growth / how Outset 8X’d revenue

35:00 How AI is upending a $140B industry



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Ep 159: Aaron Cannon Is Building the Leading AI Customer Research Platform; It's About to Upend a $140B IndustryJoe Lonsdale: American Optimist · 40 min
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