Building the World’s Most Wearable AI | Dan Siroker (CEO Limitless)

It starts with recognizing our own limitations. And this is something that really inspired me to even start the company. Realizing I'd been losing my hearing and not noticing it, and then only when I got a hearing aid. Realizing how much I had lost really opened my eyes to the fact that we all live our lives with limitations, biological limitations that we don't really recognize are there. First and biggest that we're focused on is memory. 90% of what you experience, you forget after just one week what that means. You know, for a normal tech productivity employee, if you have a weekly one hour meeting, you only really remember, at best, six minutes of that one hour from one week ago. And we don't realize it because you forget it. So you don't know what you don't know. So we basically live our lives like Dory in Finding Nemo, forgetting most of what we experience and, you know, maybe most of the time that doesn't matter. But there's so many ways in which using those moments that you forget to give you a better experience and to give you context for things that can make you more productive, make you more present. We think that's a huge opportunity.

My guest today is Dan Sirilko, CEO of Limitus. In just 24 hours after launch, Dan and team sold over 10,000 AI pendants to help people augment their memory with what they've seen, said and heard, making Limitless arguably the fastest growing AI wearable in the market. In this short interview, Dan and I talked about his journey to create the most wearable AI in the world, how the team ships fast without compromising quality, and how he manages his time with three kids. Dan also co founded Optimizely and is one of my favorite entrepreneurs to follow. If you enjoy our conversation, please like and subscribe to support the podcast. All right, Dan, well, welcome. I'm super excited to talk to you. You had a really big week. I think that the Limitless, you rebranded Limitless, the pendant. You announced the pendant, and I think now you have 10,000 orders. Or is it more?

We've got even more. We've got 10,000 orders of the pendant, 20,000 total customers, which has been kind of crazy. And surprisingly many of those are actually outside the United States. About 40% are outside the United States.

That's awesome. I would love to talk more about Dependent, but before I get there, I kind of want to talk about the history of this company. Like, maybe you can start with why you started Limitless or rewind the first place.

Yeah. The inspiration for starting the company actually came out of an experience quite a while ago in my 20s, I started to lose my hearing. And when I turned 30, I tried a hearing aid, and it was magical. I to. To lose a sense and gain it back again felt like gaining a superpower. And ever since that moment, I have been on a hunt for ways that technology can augment human capabilities and give us superpowers. And that led me to the path that we're ultimately on today. So we started the company back in March 2020, and it was started really trying to find ways that technology can augment human capabilities, not replace human capabilities with AI, but augment human capabilities with AI. And we took a meandering path and ultimately landed where we are now, which is a personalized AI powered by everything you've seen, said, or heard.

Yeah. So I would love to learn a bit more about the meandering path. I think in the beginning, it was mostly to, like, remember your personal activity on a computer or, like, kind of what you're doing, and then you kind of move towards more of a meeting focus, maybe talk about that path first.

It's a bit zigzag, you know. One of our investors, Andreessen Horowitz, describes this as the idea maze. You're just sort of exploring the idea in kind of a maze, and certainly feels like that. So the very first idea that we tried and launched pretty quickly was called Scribe. It was an online meeting bot that would join meetings, transcribe the meeting. That's why it's called Scribe. And that was the beginning of the pandemic. So lots of people were doing zoom meetings, and we learned a lot from that. And one of the things we kept hearing from customers is they wanted to capture way more than just meetings. They wanted to capture their lives. They wanted to capture what they see, what they hear, what they say. And at the same time that we started hearing this from users, we were seeing the emergence of Apple Silicon M1 chips, M2 chips, and that really fast compute that was possible for the first time ever on native devices. And so we had the idea to. To pivot, really, and create a new product called Rewind, which was a Mac app that would capture everything you see, saying here, including meetings, store it all locally, compute all locally. And that took off. And then what was interesting is it sort of came back to meetings. Because what we found is with Rewind, what people loved with Rewind, and still do, because it's out there and people still use it, is that their data is safe. It's safe from their employer. It's Safe from the government, it's safe from us. And we realized if there is a way to actually deliver on that same privacy guarantee, but also have the convenience of being in the cloud, then that would be the best of both worlds. And so that's what Limitless is. It's the same guarantees of a local app, but with the convenience in the cloud, you can access your data from any device we have. You can use the best AI models and you have unlimited storage. And so that's partly why we call it Limitless. So that's how we landed where we are now. And, you know, we just launched this week, so we'll see how it goes. But so far, so good.

What was the rationale to extend beyond just like software in the cloud to actually build a hardware device, like an AI wearable device?

Yeah, it really started with the problem first. So I, if I could have avoided building a hardware device, I would have. You know, I think a lot of people out there is like, oh, I want to build a hardware device and then what should it go do? We have the exact opposite opinion. I personally think, you know, and I'm not the only one who thinks hardware is hard. And if we can stand on the shoulders of giants and build an iPhone app or an Apple watch app, like that would have been much easier. The challenge is that the existing technology and particular the operating systems that run on those devices limit what you can do. You can't have an always on microphone that captures everything you say in here. As soon as you get a phone call, the microphone stops. As soon as you watch a YouTube video, the microphone stops. And so the frictionlessness, we wanted the ability to capture what you say, say what you say and what you hear without having to remember to go back to turn it on. And to have the convenience of being able to ask your AI anything with just a tap of your finger meant that really to deliver on that customer experience, we had to build the technology necessary, which was unfortunately hardware. And you know, that was why we started that path and that's what we're doing now. And you know, one day I'm sure Apple will support these use cases, especially if we're really successful, in which case, you know, be very happy to use their platforms instead of having to physically create things out of, out of matter. That is much harder than creating things out of bits.

Got it.

Yeah.

I was looking at the limitless pen and there's like so much that I love about it. I love how it's focused on meetings. It helps with personal note taking. I love how it's like a full solution. It's not just hardware, but it comes with software and the confidential cloud. And of course I love its price point and battery life. Only 99 bucks for 100 hours. That's pretty amazing. Maybe talk about, you're like really good at like speaking directly to the customer online. So like talk about how someone's life could be changed with this thing. If I buy this thing and I have it, like, how can my daily tech employee life be different?

Yeah, well, it starts with recognizing our own limitations. And this is something that, you know, really inspired me to even start the company. Realizing I'd been losing my hearing and not noticing it, and then only when I got a hearing aid, realizing how much I had lost really opened my eyes to the fact that we all live our lives with limitations, biological limitations that we don't really recognize are there. The first and biggest that we're focused on is memory. 90% of what you experience, you forget after just one week what that means. You know, for a normal tech, you know, productivity employee, if you have a weekly one hour meeting, you only really remember at best six minutes of that one hour from one week ago. And so we, and we don't realize it because you forget it. So you don't know what you don't know. So we basically live our lives, you know, like dory in Finding Nemo, forgetting most of what we experience and you know, maybe most of the time that doesn't matter, but there's so many ways in which using those moments that you forget to give you a better experience and to give you context for things that can make you more productive, make you more present. We think that's a huge opportunity, you know, and we're focused right now on meetings because I think that's where it's the biggest immediate opportunity. In particular, you know, we take note. Taking away from you. You don't have to take notes. Yeah, there's this myth that taking notes helps you remember the meeting better. But really what taking notes helps you do is remember the thing you're writing down, but as you're writing it down, the thing that's being said immediately afterwards you're going to figure out and you putting everyone here in the first place and so being able to be present, focus on the person directly in front of you and not have to worry about note taking, about tracking action items, coming up with a summary, sharing it out afterwards. Limitless Automates all that for you. So that's how we start. And we've got A long roadmap of things. And by the way, it's all public. If you go to roadmap limits, AI, you can see all the things we're working on that's going to make that, it's going to extend that. But that's sort of the key wedge that we're starting with.

And of course when it comes to like, you know, meetings are, can be the biggest waste of time time ever, right? And like all this best practices around taking notes and like sharing rafter it's just like a lot of busy work that people don't want to do. So but I think the biggest barrier here is like, you know, if I'm going to a meeting in my company, like how, how do I know this thing I'm wearing is not like you know, sharing information with limitless or like just like privacy concern and you kind of tackle that head, head on. So maybe talk about that a little bit more.

I'll just say one quick first thing, quick thing, the first thing you said, which is meetings today are not fun. But our hope is that we make meetings a joy. They become the moment. If you think about it, meetings are at the most fundamental level as a social species, what we do, we connect with other people but we get distracted from that connection by all the other things that are on our plate. The next meeting, you know, back to back meetings, I've got hard stuff. I'm thinking about that, you know, like if we can truly be present and connected with the people we're with, I truly believe we can make meetings a joy. So that might seem like a crazy claim, but that's just. I wanted to address that first of all on your the bigger question around privacy. So from the very beginning, this is something we really focused on because we knew in order for the pendant, in order for our web app, our Mac app or Windows app to be accepted socially, it needs to respect not just the privacy of the user, the person running it, you, but the people around them and their organization. And so we've done two things I think are pretty novel here. One is called consent mode, which means that in a meeting or a conversation, we actually keep track of who is speaking. We can identify their voice and, and if somebody starts speaking who we haven't identified before and they haven't previously given consent, we don't record it. So you can have an entirely, you know, you can have an entire conversation. I'm speaking, I've given consent, you're speaking. And it just gets my side of the conversation until I say, hey, Peter, would it be okay if I record this conversation? It's important to me. I want to be able to remember it. You say, sure, no problem. That's a verbal opt in. As soon as you've given a verbal opt in, it's identified your voice, then for that conversation, we record it. So that's a huge breakthrough. No one else has done that before. That's called consent mode. The second breakthrough was Confidential Cloud. And that's going back to what I said earlier, which is giving you all of the privacy guarantees you get of a local app, but with the convenience of being in the cloud. And that was also a major breakthrough. We've got eight bold claims on our website if you go to Limitless AI that all begin with your data. What do we mean by your data? Your data is legally protected, your data is encrypted, your data is safe from the government. We really thought through all of the different angles to make sure that when you use our product you don't have to worry about your privacy. You get privacy and convenience.

That's awesome. Yeah, I'm definitely going to try it out. Hopefully I don't have to pass like a security review or something. I'll definitely try it out. Yeah. So, so now let's talk about something a little bit different. I mean, I've been really impressed with how you put together a really awesome team and kind of how you build products and you know, you've been an entrepreneur for like 15 plus years. One of your advice that you shared is to ship faster and higher.

I would commit fully to it and not hedge and just say in this moment, like, you know, the last few weeks or maybe last few months, frankly, I have been so heads on, focused on this product and this launch. I basically, everything else says it's gone by the wayside. Partnerships, emails, investors, you know, I just completely say like I'm heads down focused on product and that's what I'm focused on. And you know, usually even if you're wrong, if you're focused on at least one thing that's meaningful, you will do a good job of that and then you can move on to the thing that, you know, you'll feel the pain after you're done. Like this week when I've emerged from the cave of that was, you know, building a shipping product, you know, I was in the code base working hand, hand in hand with their engineering team and now I'm starting to see the pain. Oh, that's something I should have forgot. Oops, that's a partnership I should emailed and you know, those are the kinds of things you find out afterwards. But most of those aren't actually all that important if they, if they weren't so painful during the moment.

Got it. I really love that. And like, you know, you brought some really amazing talent. Like, I know Stanley from the Twitter days. He's now, he was designer, he's now a co founder, I think, of the company. How do you attract people like, like this who, like. Or maybe he's just tired of the big company thing, you know, that helps.

Yeah, it's certainly. It's easier to hire people out of big companies where they get a chance to have ownership and autonomy and really master their craft. You know, I, it is, I'm incredibly, incredibly lucky to work with folks like Sami and other folks on the team who are just world class at what they do. You know, I don't have a secret recipe other than to say that it requires care and attention to the culture. You know, trying to build the kind of culture where they're going to thrive, be energized, be motivated, give them things they couldn't get at their prior employer, like Twitter or Google or Facebook. You know, the kinds of environment where they can truly do their best, the best work of their career. I think that's a key part of it. And you know, in Stammy's case too, like, we promoted him to co founder too. So we had, you know, we have a. That's a pretty atypical thing to do. So giving people the opportunity to take on more and to do more and to reward their, and recognize their, you know, their impact, I think is also really important. And then the other part is I think you just aim high. Like you keep trying to raise the bar on yourself and on the team and you know, don't. This is why that the, this goes back to the higher slow in the advice earlier, because people think, oh, if they're no good, you'll just fire them, whatever. But the thing is, you don't realize when you hire too fast, you are actually creating a large opportunity cost because that person that is in that role in that moment could have been somebody 5 or 10x better, but you just settled on that first person or the person that you think is good enough. And so that's another thing to recognize. Especially as a small team, each person has incredibly high opportunity cost. And almost certainly for the person you're about to hire, there's probably somebody out there who's two or three or five or 10 times better. It's often better to wait to hire them than to sort of fill the team with the best first. The first, best person you could think of to. To hire for a particular role.

Yeah, that's interesting because the usual advice is like you got to think like a year or two ahead when your company has like you know, double the inside or something and you got to hire the right people right now. But maybe that's not good advice.

I don't think that's.

Who knows what the company is.

I don't think that's good advice. I think and I made this mistake plenty of times, you know, with optimizing. We raised a $28 million Series A and then a $57 million Series B and a $58 million. We didn't need any of that money. And I just thought, oh, it would be great to have it. It's great valuations. Just keep it in the bank. The mistake is. The mistake isn't raising the money. The mistake is spending the money. That was what we did is that we ended up spending it on all kinds of people. We probably didn't need, you know, we didn't have the, the visceral pain of that particular role. But if you hire some bigwig CMO who's come and done this before, they're like, I need this demand gen person, I need a events person, I need a. You end up building this whole army of people of which the vast majority aren't really having that much of an impact. So that's again a good reason to hire slow is to really. You want to feel the pain. You want to make sure there's really pain. You're spending the money. That was what we did is that we ended up spending it on all kinds of people. We probably didn't need, you know, we didn't have the visceral pain of that particular role. But if you hire some bigwig CMO who's come and done this before, they're like, I need this demand gen person, I need a events person, I need a. You end up building this whole army of people of which the vast majority aren't really having that much of an impact. So that's again a good reason to hire slow is to really. You want to feel the pain. You want to make sure there's really pain you're solving by hiring this person trying to be proactive. You're almost always going to get it wrong. You have somebody who's going to be twiddling their thumbs not having them impact that they should have. And again that's opportunity cost. As a company gets bigger and bigger, you know, you start having coordination issues and so just, yeah, hire slower than you think you should.

Yeah, if you hire like really top notch a talent, like they will rise to the occasion. Right. Like they will surprise you. What?

And many of them, by the way, want to be at a small team. They don't want to be part of a 300, 400 person bureaucracy. They want to be part of a nimble 20, 30 person team. I'm sad to admit that like even the team we have today, 20 people, we are able to get more done ship faster than we ever did with a team of hundreds at Optimizely. And so it really shows you that a small nimble team that's, you know, truly exceptional, like folks like Sami, can really actually have just as much impact as a huge army of people who are, you know, who aren't truly the best fit for the company at that stage.

All right, so two last questions. So, so you know, you worked at Optimizely, which was kind of like an AB testing platform. How do you feel about this whole, like maybe just came out of left field, but how do you feel about this whole product management function and this data oriented approach? Do you think this is the right time and place? Maybe you'll hire some PMs as a company, continue to scale or.

Yeah, I mean I started my career as an associate product manager at Google and so I have been a PM. We had fantastic PMs at Optimizely. We don't have one here. I'm basically the PM now at Limitless. And I do think product managers play a really critical role. But I do think one of the downsides of hiring a product manager and hiring the wrong product manager is it allows the rest of the team to outsource their thinking to that pm. You know, the PM then sort of dictates the priorities, the sort of the work to be done. And you miss a lot when you actually have an engineer who's also thinking about what's the highest impact thing we should be doing. Because they know the benefit of the engineer is they know the effort, they know how much effort it's going to take to do that. So they are actually in a much better spot to accurately determine for any piece of work what the ROI is, the amount of effort to build it and the return we're going to get. And so great examples this week. You know, we launched, I mentioned to post this video yesterday, but we launched on Monday. Almost immediately we were getting A ton of votes on our roadmap for additional language support. It's not something we really immediately considered, but one of our engineers saw this. We're saying, wow, we've got like 185 votes for additional language support. He recognized there's some really low effort ways on our part to leverage other solutions to make that possible. And within days shipped support for 33 languages. Now, would a PM have done that? I don't know. You know, I don't know if a PM would have been so close to the details to understand the effort necessary to actually do that, that they would have prioritized that ahead of the other things they're hearing. So I do think that's the biggest downside of hiring a PM is you don't want your organization to outsource their thinking to one person who only has one point of view. You want to make sure everyone feels a little bit of that product ownership over what they do.

Yeah, that's a good point. PM will probably like, be like, oh, this sounds like a lot of work, so let's put it on the Q3 roadmap or something.

Right, right. We'll just put it on the backlog and it never happens.

Yeah, exactly. So my last question here is a selfish question is like, how do you do this with like three young kids at home? Like, like what? What does your day look like? How do you ruthlessly prioritize your day?

It is very hard. This goes back to what I said earlier. That's where, like, the main thing is, the main thing stays the main thing. I really try every day to get home in time for dinner at 5pm so I'm done with my day at 5. Maybe late night, I'll get back on. But, you know, I have dinner with my kids, I shower them, I put them down at night. And so that is a ritual I stick to every weekday if I'm not traveling. And that's hard. I mean, it means you do less things and it really. And by the way, my most productive 15 minutes of my day is 4:45 to 5:00pm because I know I've got. The clock is ticking. I got to get home in time for dinner. And so that forces constraint. And that's the thing. Maybe if you are, you know, earlier in your career, you don't have that. I just force yourself to have that constraint. Because with that constraint comes creativity, ways you can figure out how to work. And the biggest thing, it goes back to the product too. It's scope, figuring out what's the scope that you need to be focused on and cutting your own scope, realizing that you can't do everything. And if you did everything, you're going to do everything. You tried to do everything. Anything you did, you're going to do poorly. So it's saying, what's the main thing for me? What's the focus I should have? And that goes with the willingness to accept you're going to disappoint people, you're not going to get back to people as fast as they would like. There's going to be things that drop because it's not your main thing. But ultimately, if you're successful, that's fine. People will forgive that, you know. And so I think it starts with this sort of mindset of I need to really ruthlessly focus my time, let everyone know that's what you're doing. You know, no one's going to be offended that you said, sorry, look, I can't get this done because I get at home in time for my kids and it's not my top priority. And so it starts with that, being clear on what your priorities are and focusing on that.

Got it. So set the right expectations for co workers and your wife and everyone else. Yeah, got it. This is awesome conversation. Thanks so much for your time.

Yeah, yeah, thank you for your time. Really appreciate it.