The Incident That Led to a $375M Startup

My really crude AI had a full conversation with my girlfriend at the time. It told her I love you. It sent her memes. It went back and forth without me realizing it. People like to feel known, not surveilled. I started programming at like 10, became like a senior-ish engineer by like 11, 12, and team lead by 14. Insane.

Is that even legal?

There's definitely—

I actually only ended up spending 3 semesters in college.

And you guys dropped out?

He finished his entire CS degree in 3 semesters. What? Over the years, I'd pitched different startup ideas to WJ, and he kind of said that those sucked. It was when I had pitched Cloaked, and he's like, this is actually a good idea. I'm like, wait, I'm onto something.

What does Cloaked actually do?

Cloaked is a consumer security and privacy company. We're here to clean up your past and protect your future. With the Series B, we've raised over $300 million.

Holy shit.

Did you have any specific stories from raising from some of the folks that you guys had raised from?

I can talk about like one with—

Well, okay.

Abhijeet, Arjun, welcome to the show. Welcome to the MakerPod.

Thanks for having us, guys.

Thanks for having us. Excited to be here.

Yeah, I feel like we've known each other for a couple of years but have not really had the excuse to just like go really deep on your story. So I feel like you guys are two incredibly interesting brothers that happen to be co-founders, and I'm excited to dive in. So Thanks for being here.

Appreciate it. I'm, I really enjoy the time we spend together. I'm glad to put on a pod.

Not to mention, like, we've actually gotten to meet and learn a little bit about it, but just exciting to share with the world, like, your guys' story, how you got about. We did a little research on you guys beforehand, and like, there isn't really much that talks about like the full arc. And so what we hope to do today is just like really dive in and like hear the real Full Cloak story from the beginning to where you guys are now.

Sure.

Cool.

So let's, let's just start with childhood. Like, would love to paint the picture for the audience. What was the beginning? You guys are obviously brothers who work together. Like give us like the origin story of kind of the early days of you guys working together.

Older brother related to start it?

Yeah, so I'd say the first part of this is always that one, I have to point out that I am the older brother, but I'd say is that I've always been technology from a pretty young age. We were decent, not too well off as a family early on, but we did have a family computer growing up. And from like 3 to 4, jumped in, started to use it, remember playing games like on CartoonNetwork.com, and by like 6, 7, started taking apart computers, figuring out how it works, but then really got into programming at the age of 10 when I kind of realized one day I had a friend who made a website and I got jealous. I was like, oh my God, how do you make a website? And it hit me when I, uh, when I got home, I was like, wait, let me go figure this out. I Googled, read, like wrote a notebook on HTML and started writing, built my own website in the first 4 hours. And then it just kind of snowballed from there. And Abhijeet always been with me where we've been, we joke from Legos to startups working our whole lives. He always kind of saw what I was doing. It's like, hey, let's start building together. Um, and Abhijeet can talk about his journey into it, but he's always been a builder. And I think programming just became something that I started, then he kind of took to the next level. Yeah.

What's the age difference between you two?

We're 3 years younger.

Yeah.

3 years younger. Okay, cool. And then were you guys always best friends? Like as soon as you came out of the womb, like were there, was there a time where you guys were enemies?

I mean, it's funny.

Uh, I think our relationship actually grown a lot in the last—

how many years? 15 years working together. When you have a, a builder family, is a lot of your relationships like tend to revolve around building. And like, I think about like our early childhood and the memories that come to mind are like sitting, you know, we're 2 and a half feet tall, sitting in the back of his chair while he's putting together a MapleStory private server. And like, he's trying to explain to me how databases work, and I'm just like, I want to play video games, right? So we've had a long arc of, you know, going from kids in a very traditional Indian household, mostly talking about work, versus growing up, I became a little bit more rebellious, us, him and I figure out where our boundaries are, living together as like 21, 22, 23-year-olds in the city, lots of like interesting first things to cross first time. Having relationships and partners staying over.

I think we definitely have all had all the different types of fights. I'd say between us, for the family, the one thing I always stick in my head was when we were very little, none of us had locks on our doors. It was a big thing around like—

In the house.

In the house, we didn't have locks. Very different now. It's like now having girlfriends, different people, like we're so used to it's an open door policy between us, etc. The joke is even when I've got a big idea or I'm just an idea, I like knock on the door and he's fast asleep. I'm like, are you cognizant? And then I start pitching the idea. Or he's in the bathroom, I just start talking while he's in.

Has this happened?

I mean, this happens like this morning.

Oh, okay. Like it happens.

He'll call. This was literally yesterday. He was driving from Florida to Maryland with his girlfriend. And he calls me at like 7 in the morning being like, are you cognizant and awake? And I'm like, no. He's like, okay, get cognizant and awake. I'm like, give me 25 seconds, and then he pitches me on something, and I'm like, this is great, let's talk about it in 2 hours. I'm awake.

But the difference between the two of us, I never approached like, that's just how it is. Abhijit built a lock on his door when he was 5 or 6. I remember, go your own lock, his own lock on the door. He took apart a coat hanger and he built a full mechanism, and his door had a lock. And I remember my dad trying to open the door, and it's like, it's locked. And it's like, what do you mean it's locked? He's like, My dad would just speak to the door. I locked my door. And then like after like going in and seeing it, he had built a full contraption to actually keep himself locked.

And were your parents like builders? Did they— is this just like a natural thing for you guys? Or like how, how did that— how did you get that natural like instinct to do that even?

Our father's in technology as well. Um, he, he runs his own technology company. Um, definitely there's some element of it's in the DNA, it's in the house, it's in the air. Not directly as much as, you know, sitting down and saying, here is a system, a technology, a circuit, go build it. But I think when you have the, like, a mental model of what creativity looks like, it's a lot easier to start tinkering in that direction. I think it's really interesting for me in my perspective. I'm curious how he feels, but as like the younger sibling and the son of two people who are both extremely creative, I don't know a world in which that wasn't the norm. Form.

Sure.

Um, you like, especially with him, like, my father's at work all the time, right? He is a source of my like 9 to 5 or like when I wake up to sleep, like, inspiration. I'm curious where that fostered in you.

I'm sure I have some sense, but our whole family, through with enough time, are all entrepreneurs. And eventually our mother even started her own business and started scaling that. Um, but our father, um, was in technology and he's actually a doctor in computer science. But we were always hesitant to talk about it because they're like, oh, of course, that's where you learn things. It's like, no, we never actually talked about programming, computer science until like I was 18 when my father's like, oh, you actually know quite a bit. And then we actually, now we talk in depth about AI, talk about neural networks and all this stuff. But when you're younger, it was, he kind of looked at it like, oh, we're kind of doing some things on the side, but didn't realize as I started kind of building projects, working for different companies, like, oh, this is actually, he's actually built that skill set. I think what really shaped your childhood was that. Our father, and this kind of instilled in our qualities, was that mentality about always learning, being curious, and in— I always say this— investing in yourself. And I think that mentality of just always doubling down on like figuring it out, you're on your own, taking something apart, understanding it. Our father always approached problems like that. We'd always talk about time travel or science.

Like, I'm curious on the parenting topic, what did your dad do specifically that kind of taught you to see the world in that way, like to have this, you know, heightened sense of curiosity with everything? Like, were there any specific moments where you're like, wow, like, this is how he's sort of ingraining us in this?

I have an interesting anecdote. It's not necessarily how he saw the world, but how he taught us to value our time. I remember when I was like 13 or 14 coming back from like in this over the summer, all of my friends were getting their first jobs, you know, doing some sort of retail somewhere. Making money, right? They had disposable income, and we were going to movies, and they were buying fancy things. I remember I got in this big fight with my dad being like, hey, everyone's getting a job at the Market Basket down the street, why don't I go work there? He's like, no, you might like having money, but spend that time on yourself. And I remember I fought with him for this whole summer, and then this summer ended up being the summer that him and I started our first company. So there's like one world in which I, you know, there's the rugged individualism of like, yeah, go, go make your own way, make your own money, do everything. Um, the other one was, you know, sit down, invest the time in something that probably won't have monetary outcomes, and it might turn up well. And I, I try to think a lot about what would happen if my dad was a little bit more trusting of me and my instincts. And if he— it's funny, you talk about like how you trust people and let them grow. He almost didn't let me go down my own route of, of doing that. He said, no, focus on yourself and kind of forcing me to focus on myself, and it paid off.

Yeah, I was saying, in hindsight, do you agree with that advice?

I mean, I think the bias towards self-improvement is what I highly agree with. Um, I think I thought I was self-improving by trying to, like, you know, be in the real world, get a job and everything, but my— like, I was like 14, right? My, my perspective was so small compared to what my father had.

Absolutely. In hindsight, I think that my, the difference is, right, we're talking right here, right now as founders working in this company.

Sure.

The idea, we never chased money. And I think that was something that was very ingrained in us. It began with not having a lot. Now I think our family's in a much better situation, but we never still like, we have to go make a lot. It was always chasing the idea of getting better at what you like. Phrase, chasing excellence.

Right.

Being really good at what you do. Versus trying to chase money. And like, yes, I think in college I remember where like we, I had a floating balance of $100 in my bank account, like almost all the time, roughly around that. And like going to movies, like $20 ticket. And I like, I think about it, but I never really like was stressed about it.

You're just like, whatever, that's how it is.

Whatever. Like that's how it is. And now we're in a completely different position because I think the education itself compounds way faster than the emphasis on money. And I, I'd give one more point about, we talk about our father, but I think the other dimension is our mother. Where our foundation education has always been what put us ahead. Where I remember doing multiplication tables at like 3, decimal division at like 4 or 5, because their mom's like, having a strong foundation education just gives you the ability to do a lot. And so school was never the hard thing for us. And we were predominantly like an all-white town. And it was like, not a lot of minorities. Now it's kind of crazy. Like I remember seeing, we went to an event, it was like all Indians, like all Indian tech founders. I'm like, oh my God, like that's a, way different perspective, but because we were always focused on education, we kind of were very different than everyone around us. Sure. And, but then we started embracing being different. And I think definitely as you get older, you like it more, but when you're younger, you're like, oh, well, why am I different than the other kids? And I think it pays off though over time.

So you were talking, I think we skipped ahead to like 13, 14 years old, but you guys started, you started building a game, right? That was kind of your first foray into programming. So maybe talk about that. There's something about the MapleStory server and— Yeah.

So I'd say even before that and what led to that experience was the kind of core experience. I started building websites when I was 10. And I kind of got the, I remember the time I learned the word entrepreneur, which is in the third grade. And I only remember that experience. I thought it was a really weird word.

It's a French word.

Yeah. Like, and it was, and I remember seeing that and I was like, wow, what a weird spelled word. But why I bring that up is that from like the third grade on, I'd always had a mix of both technology and business. I had started an entire economy using Pringles in my third grade. Where our teacher had like these Disney dollars where you could trade Disney dollars for things. And I had accumulated $150. The next person had $20. And it's because I had started realizing Pringles towards supply and demand. But why I bring that up is that when I was, started programming, I actually started doing cold calling and started trying to get people to, can I make you a website? Can you do a thing? Because I started, it's like, even if I didn't know how to do it, I wanted to try to like get a project, do something and make it happen. And like, I remember my first client I closed, I called, uh, I called somebody and said, hey, do you need a website? And we start talking and I was in my little chair. I had drinking, uh, juice box or Capri Sun. I can't remember one of the two. And she, um, said like, oh, I'm so sorry, my 3-year-old's running around. And I was like, oh yeah, my 3-year-old. I have a 3-year-old as well. I'm just all the time running around all the time. And I was 10 and I was like, But I closed the deal. I couldn't get money, so I had to open a PayPal account in my dad's name, but we actually got paid and started building. But I just kept taking on projects. And, but since we were kids, video games is our big foundation. So I really kind of exponentially increased my knowledge with video games where we built a MapleStory private server for anyone who knows what MapleStory is, but it's a game from the past that we were both playing, but whenever we played games, building the server and having friends and different people connect to it always made me way more fun.

More fun than the game itself.

Yeah, more than the game itself. When Minecraft first came, like, was like, I remember way back in the alpha and beta, like, I was like an hour into playing into it and I was way more interested in how to get the server running and how you get different people connecting than I was playing Minecraft. But we started, I started learning how to build this private server. I learned Java. I learned databases. We didn't have any fancy computers. I had a Black Friday laptop that had become the cornerstone of my entire career, but I'd run a server, was running a server on that. And it'd get extremely hot, like actually, like if you touch it, like it would scorch. And so I had a damp towel on it all the time. And we had 1,500 concurrent players actually connecting. And we had our own website and we had actually hired moderators. People are moderating the server and it was like all running. And I still remember like this, and I was like, I had to put the laptop laptop a little down, I had to put a towel on it. I couldn't play because that's not only my only computer. And so we had to like, when people are playing on it, I just, Abhijit was using his laptop and I'd watch as people were playing on it. But definitely created a foundation for me because I learned about networking. I learned about how like server states, databases, I wrote my own code. I still think the bug of programming really picked up then. I think started the HTML stuff early, but I feel it's lost now. But I remember waking up every morning with like a smile on my face. There's a bulletin board for at least from programming where people would share scripts and things they created. And I would like wake up every morning to see what new script somebody posted. And I would read through the code, see what they did. I'm like, how could I integrate that into my game or my website? That feeling, I feel it's not no longer, maybe now AI is just like, a little too crazy, but that joy of waking up and reading new code that people put out there, contributing, really, like, yeah. And I contribute back to it. Like, it was just awesome.

That's awesome.

And so that was kind of, it sounds like your first, like, assembly of people and organization. Where did we go from there?

Oh, it's just been, so like, that's the first time where Abhijit and I actually started, like, truly starting to work together.

And how did you guys divide extra responsibilities? I'm curious.

It's interesting. I, I, there's a little bit of a younger sibling syndrome here. Where I've always kind of felt like I've learned a lot of things and it's always been about like 2 or 3 years below before what he did. So I felt like I've always been playing catch-up my entire life and maybe only the last like 5 years or so I feel like we've had a nice dividing and conquering. But in general, we've always had more work to do than time to do it. So a lot of it's been down dividing responsibilities. He always did some of the more complicated infrastructural architectural stuff. I was actually always more hyper-obsessed with like the customer experience, the products, and what people actually touch and use. That's our initial foray. Even when it came down to the original day, like my foundation in computer science was actually not websites, but like programmatic mathematics, very deep algorithmic work or stuff that's very customer-facing was always where I, where my bread and butter was.

Cool.

And his was all the hard stuff.

It's actually an interesting point. I never thought about it till now, but even in that, in this private server, Abhijeet would be in the game interfacing with players and moderators. I had a cool like admin thing, but I never like logged in as much. But Abhijeet was on, uh, and I was much more on the server side trying to get it going. But that experience divide and the server— now I think the, the interests have matched both on every dimension. But early on, that divide kind of started.

So you guys, by the age of like what, 12 years old, you're both technical?

Yeah, yeah, crazy.

And then you were leading, like, can you talk more about how you got involved with like another company that then brought you on and you're, you're being promoted in like a very short period of time?

The, the kind of spiel I always say is like, I started programming at like 10, became like a, like a senior-ish engineer by like 11, 12, and team lead by kind of like 14.

That's insane.

Is that, is that even legal?

Uh, there, there's definitely, uh, like, don't wanna get into naming any companies and things, but I was paid in iPod Touches and different things. Like I was super excited because that mindset of make, in hindsight, I'm like, I should have tried to make some money. But now actually I'm like, nah, it's actually okay.

Was there a moment you were like, I'm really good at this and I know it? Like did something happen that you were like, oh wait, actually I'm quite good at this?

I think that imposter syndrome, uh, I don't think I've ever hit it. I think maybe now I'm starting to feel like, wait, we're hiring all these super smart engineers. When is somebody going to be way better than me at something? And I'm like, still kind of trying to figure out that line, but I think we're slowly getting there. But growing up, I've always felt there's so many people smarter than me. Um, I think there's one moment where it hit me, which was in, um, so when I got my job at MIT, um, and then also when I went to college. But so I worked at MIT when I was 16, 17. Um, I started off as an intern. I had some stuff before then, but I was, uh, came as intern a few Remember the science class chemistry? You do those labs where you follow the instructions, repeat the experiment. So I was the kid who would be testing those things before they would go out to kids in different schools. And I did that for a total of 7 days. It was boring and I hated it. But I was just like, I was in the Media Lab and I'm like, MIT. And I was like, this is awesome. And I was an unpaid intern there. But I decided to just wander the halls. I asked my the professor I was working under, can I just like walk around and talk to the people? And so I started asking everybody, I'm like, what do you do? And like, I remember in an elevator, I was talking to somebody and she was, the lady was the product lead for a project that was like an Android app drag and drop builder. And she was telling me about it. I was like, can I join your team? And she's like, well, we're about, we're just live. We just went live and we're not really looking. And I was like, can I just like join you? And then She's like, okay. Then I worked there for like 3 weeks, realized it wasn't a lot of work, but then I just kept asking people what they did. I wandered down the hall and I found my— what would be my future boss. And we geeked out about Java versus JavaScript and we had such a like really awesome conversation. And then he's like, why don't you work with us? And then he gave me an internship to work. But then what happened was within the month I got promoted to the team lead.

How big was this team?

This team was like 9 people.

And how old are these people?

Oh, they're all grad students. Postgrad, undergrad, and some like much older, like, like masters, like have master's, PhDs.

You're not even 18 at this point.

No, I was not even 18. And I also was like the Git expert because everything at MIT was SVN at the time. But like, I remember like I had so much respect for my boss, but he would tell people, I was like, oh, because MIT had started mandating you have to use Git. And I was like, oh, I hate Git. And then all these different people from different teams would be like, how do we do this? And they're like, ask Arjun. I don't know how to use Git. Um, and, but what was really cool was given the opportunity to, like my, the reason why I grew quickly is the first day my boss gave me a task. He's like, it'll take probably 2 weeks. He's like, set up our environment. And then like, what I would end up doing is I built kind of the core blocks that eventually power a lot of different things that use the Logo programming language, the drag and drop that powers Scratch and a lot of different projects. I did that whole thing in 4 hours. So I got the environment set up because there's no documentation. So he's like, ah, you gotta figure it out. I say, wrote documentation, got the environment set up, and then he just started giving me more and more things, and people just started saying, wait, this guy knows what he's doing. Yeah.

Would you call this person a mentor to you?

Oh yeah. He, um, I picked, I talked about Cloak with him 3, 4 years ago, and he said 2 lines. Now I'm giving the credit because people think, people think I came up with the line and like such a cool, and then I'm like, it actually comes from my former boss. So there's two things I always say about Cloaked. People like to feel known, not surveilled. And people like this idea of like software and technology, things where they're customized and personalized. They like that, but they don't want to feel compromised in the process. Those two lines actually comes from my former boss.

I forgot about that.

Yeah. I say it a lot and everyone thinks like, oh wow, Archie's really good at some soundbites. But actually my old boss is actually the one who said that to me. And now I kind of see it stolen, put it in my, the way I pitch it. He was definitely a mentor and he's actually the reason where I changed my college direction where my goal was to major in computer science, go and write in engineering. We had a lot, I remember that long walk for an hour where I was like, so what do I, what should I do for my life? And he's like, Arjun, you shouldn't major in computer science. You already know everything you could possibly know. Like you should go into business. I, I, like I, because we had started working on our own startup at the time on the side and started building it. So I'd work a full day at MIT, come home. Um, and then I would then start working on our startup at night. And just a loop. And so then I decided to go like a unique path, like an opportunity where I could get 2 degrees from a school called Babson College and Olin College of Engineering. So you can do business engineering. And that was the right move for my mentor then.

What was the startup you guys were building at that time?

It's Hey Heads Up, our people reminding people platform. Okay.

What was that?

Do you want to give the promo, the basic spiel?

Rewinding the pitch. If you ever need someone to do something for you, use Heads Up. The idea was that back then there wasn't necessarily the idea of Google Calendar as much. Um, Doodle wasn't really out then. Uh, but if you, for like meetings and events at work, you use Google Calendar, but everything else, what do you do? You kind of like use to-do lists. Your, your wife tells you to take out the trash. You get a text on your phone and then you're like, oh, I forgot. And so this idea is that we would use calls, texts, and emails to coordinate or pester and remind you between two people.

And in the process, we actually ended up building effectively a telephoning company. Like, we had entire telecom infrastructure, routing, phone numbers, emails. How old were you guys?

I was 17, Abhijeet was 14.

Yeah. Crazy.

What were you doing at 14 years old?

Not that.

Well, we built whole infrastructure around how any sort of signal can trigger any sort of communication. So whether you're leaving your office or, you know, you're a time-based signal or something happens and this triggers something else and whether it's texting you or calling you or having your toaster pop up, we just wanted to build this system of connecting all the plumbing and all the pipes, which I mean, I don't need a segue to Cloak, but like this is sort of thinking about how we lay the foundations of how we can get anything to segue.

What's the basic pitch though for those listening? Like what does Cloak actually do?

Yeah, so I'd say, so Cloak is a consumer security and privacy company focused on how we put you in control of your data and identity. But the simple pitch, we say we're here to clean up your past and protect your future, all as one solution. And it's all around this idea of we think about privacy as all about being anonymous, but it's not about being anonymous. People, we all realize we're at risk of identity theft, hacks, being compromised. We're inundated by scam, spam, and phishing. And there is a deep concern around surveillance, being tracked, who knows what about me. And we turn that into one solution. And the real thesis is that we're not here to make privacy an or statement where you have convenience or you get privacy. It's we want to really be dutiful around keep doing what you're doing, but Cloak makes you feel better about that entire experience. And like that's really our ethos is that there is a way to do it. You just have to think about the problem a little differently where you keep your existing technologies, existing workflows, but introduce security and privacy into that. And it's been paying off. I think we finally, we've cracked the audience that no one has been able to crack before.

And how do you guys make money?

Yeah, we're mostly B2C consumer subscription. MRR, ARR, people pay monthly or annually for our product.

How much is the product?

It's about $10 a month for individually or $100 a year annually. And then we have tiers for couples and families.

Cool. And is that competitive to others doing it? Is that higher or lower?

We are on the price point side, lower than—

We're probably pretty underpriced. We like to think about what it means to like tackle privacy as a whole. And there's many people who do individual point solutions that their individual point solution is more expensive than their entire suite. We probably could charge more, but we're not right now in the service of maximizing that figure. We're really thinking about what does it mean to grow, scale, and provide the maximum amount of value to customers. Cool. There's a root in everything somewhere.

Let's learn a big set of our first failure where we built that first startup, the first iteration of startup. And we just kept building feature after feature after feature. We're like, we wanted so many features and we realized that like we had like 100, we couldn't get any users. We had like 100 users and then we were very, very demotivated and we thought we could solve it by adding more features. It was when then we took a step back and I finished high school and then I was going to college. And so the summer after it hit us, I was like, well, what if we did fewer features, focus on the core functionality and solve the problem where both people don't need the app? Only one person needs the app.

I just, I remember us having this conversation when I was, it was like the middle of my sophomore year wrestling season. So I'm in the middle of, you know, tournament hell and I'm cutting weight every day trying to like be 15 pounds lighter than I need to be, not drinking water, not eating food. And I'm doing my like calculus class and then I come home and then me and him are chatting about like, you know, how do we reach product-market fit?

Yeah.

And I'm just sitting there like, what the hell is my, what am I doing with my life?

Can I ask what were kids at your school thinking of you guys?

Well, it's interesting. Um, perhaps you have more of that experience. Uh, let's go back to your previous question of like, when do you feel like you're doing— you're— you feel like you're, you know, good at something. I think one of my core pathologies is I think I've been surrounding myself with people who are exceptional from like— I mean, I've had an exceptional father, brother, mothers, and then all my classmates. I went to Exeter, which is one of those prep schools, so every second person was a national champion at something or on some USA math team or whatever. So if anything, I was a bit more of a black sheep vagabond, because I think that was a lot more like traditional academic excellence, whereas like entrepreneurship is pretty strictly outside the bounds of school. So it was hard because you still have to manage, you know, being an athlete and being in, in these classes as well as having to come back and do your work. And then you run into the 24-hour problem of not having any time, and people didn't really get what I was doing. So people just kind of thought I was goofing around.

I definitely stood out and was the weird one. I actually went to— Abhijeet went to Exeter for all of his high school. I went to public school for the first 2 years and then switched to prep school. I was a little guinea pig, right? So I learned about, oh, prep school actually could be helpful. And then he benefits from that and then went to that earlier. But even in public school, I started a club where we'd start trying to build things. And I realized nobody in public school wanted to do anything. It was very exhausting and it was painful for me where I try to do a lot of things after school and I'd have to stay. There's no place to stay in public school. So I sometimes have to go to McDonald's and sit there for 5 hours till my parents could pick me up because both of them were working. And I still remember late night McDonald's. Sometimes it'd be so late I'd go back to night school to just sit there and stay there. Like we were, I was working in robotics and I was working on building things and it was a lot more fun. What doing them, just painful of just the nuances of going back and forth, but it gave me a lot more freedom because that's like on campus, like independence. Um, and then I once again started doing things on my own. I think everyone knows who I, who I was because I was always kind of the oddball. Uh, and people in my dorm, well, I had this sign where, because everyone loved to hang out in my dorm room because I learned the hack of social. How do you keep people social? Just have another chair in your room. You'll find solely realized friends will hang out with you. Sure, sure. Nobody likes to sit on the bed. People hang out in my room a lot, and I actually had to put up a sign that says, I'm busy for doing, uh, trying to chase my dreams, leave me alone. And so I think that you were that guy.

Yeah, he had those signs. You know, some of the, some of the folks from Governors are at Cloak now, so they still roast— we still make fun of him about it.

Were you just like this kind of like arrogant young person that was so focused on?

No, no. I, so I never talked about doing, so that's, you'll see, that's why I'm not a big social media guy. I liked doing and I just never talked about it. Yeah. Um, like an example is like I kind of became mildly famous on the internet at that time. Uh, cause I, I was one of the first pioneers that, uh, hacked Siri onto the iPhone 4 in high school. And so I had like a massive Twitter following. Now it's kind of all gone. Like I had like tens of thousands of followers. Now it's like kind of like 1,500 or something now. But at the time, like girls were like all like comparing Twitter followers and they're like, ooh, who has more? And then they're like, what the hell is Arjun? Like what's going on with him? Why does he have so many? And like I was never tweeting or anything. Um, and so it's like in every dimension, I just kind of did a lot of things and then people would see the results or the ethics after it. Cause I, I never was looking for the limelight.

So sorry to jump around, but what is— what ended up happening with Heads Up?

So the first iteration while I was in high school and Abhijeet was either in middle school or going to high school, um, uh, we ended up relaunching when I started going to college. That eventually got acquired, um, as I got into my sophomore— closing up my sophomore year of college and, uh, or into my junior year of college.

Did you guys make money from that?

So we had a—

so wait, let me— yeah, I just wanna point out something.

We did make money.

But since I was so young, my name was not on any of the incorporation docs or on any of the accounts. I've never seen a single one of those. I've never seen a single cent from that.

Yeah, it's so—

think about it now. I wonder where the money went.

It was a modest outcome in terms of money. I think it's more like kind of like an IP acquisition and a technology takeover. I think the reality of it is like we could have kept scaling it. The way we got it was pretty cool is that we started scaling, we kind of cracked how to get go-to-market. We started getting tons of users, but we didn't know how to make any money.

Yeah.

So then, uh, we didn't wanna charge for the app either. So then one thing we realized when we started looking at the data was that there was tons of LensCrafters are using our app. There was, um, a church group in the Midwest, a big church group that use using our app. Then we found like there was an entire bus system that was starting to use our app. Um, and they were using it for notifications and like letting people know about rides. And then, then we started getting in touch with them, started, then we pivoted to enterprise, and then we actually ended up getting acquired by them.

Mm-hmm.

Um, our technology, our systems. Um, and we wanted to keep going. I had some, a major life event that happened in my time at that, uh, personal thing, and I couldn't keep running the company.

Sure.

Um, and that was where it kind of, it was good, but I'm kind of glad now in hindsight that we had that cuz it gave us a good learning moment.

Sure.

And we could do other things.

And it sounds like two things were true here. One is you guys were like, we're gonna be entrepreneurs. That's what it sounds like thematically. This was directionally, correct me if that's wrong.

That's right.

And then the second was that you guys were going to do it together.

It's interesting. Well, I've never worked on a startup outside of Arjun, but he has worked on a startup outside of me.

Yeah.

Okay. So when I was still in high school is when we wrapped up Hey Heads Up. But at some point in time, you know, senior year of high school kicks in, college kicks in, and he's at Babson now, which is a college for entrepreneurship. And that's where you started your second company, which I think— I mean, you can talk about like the highs and lows, but yeah, it was a pretty exciting experience to try it without me.

Yeah, I'd say so. I've done— I've done now a company without Abhijeet. I've worked different jobs, but actually doing a startup done without Abhijeet, to give a little bit of like pulling back the curtain, because it was not too many topics that I know I'm okay with going into anything, but the incident that kind of happened was that my fiancée at the time passed away. So that—

your fiancée passed away?

Yeah. So I was like, I got engaged pretty early in college. And that caused me to say like, I can't do Heads Up. And like, I completely checked out.

I can't even imagine.

Yeah. So it was a tough experience. And then instead of dealing with the grief, I decided to do another startup. And that was, I think, the wrong idea. I think it was good for me to learn that experience, but I did that without Abhijeet. And I think I picked not so good co-founders that I shouldn't have worked with. But the company did pretty well. We scaled pretty quickly in the first year and we actually got an office. We started building up the team. It was the startup was around the idea of like a portable product agency. The idea was that we could actually spin up a team of an engineering architect, design lead, and then engineers and designers that build out an entire app or website for Series A, Series B startups, and then kind of some mid-size enterprises. But we kind of build a whole team to take on your backlog or launch initiative. And it's doing pretty well, but I think picked co-founders that didn't— we kind of had co-founders clash, and that also helped me learn through that experience. But after that, like, I took a break and worked in VC, but that kind of gave the inkling if I'm gonna do another startup, it's with Abhijeet, um, because I think trust and being able to work very closely through such difficult situations, tough times, that's really important for a co-founder bond. And like, that was very useful for me to go through.

Yeah, I mean, at this point, I think I was pretty deep in the academic track. He went to business school, I went to study, I went to college, I was a major in math and CS and econ. So I was just all in on like learning and acquisition. It was actually only COVID, I think, that actually brought us back together because, you know, as many horrible things happened, it did bring us all back to our parents' houses.

So you were not necessarily going to go down the entrepreneurial route?

I was going to eventually, but I kind of wanted to— I was enjoying college. I had my rock climbing club, I had my girlfriend, I had my friends, I was living in California, you know, I was learning a ton of cool things. I figured one day or another I would start a startup and I'd probably be with him, but I just didn't know when it would happen.

Sure.

It was in this time where I was pitching Abhijeet different ideas. And this is the fun dynamic between us is that Abhijeet poo-poos on all of my different ideas. And that's usually my good benchmark when I'm onto something. Like over the years, I'd pitch different startup ideas to Abhijeet and he kind of said that those suck. And like, it was when I had pitched Cloak to Abhijeet when he's like, this is actually a good idea. I'm like, wait, I'm onto something. Like if he says it's a good idea, it means we could actually do this.

And there was some clear trust there, right? Like you guys really trust each other's word.

Yeah, I mean, this comes back to like everything we talk about growing up is it's really like how we've grown to trust for the relationship is how we base our company.

It's kind of ironic based on the business together.

Right. But I mean, privacy is foundational trust, right? Like that's the currency of the social capital. But everything we've done from date has always been like we have a sense of what we each other value. We have the sense of like what kind of problems we like to work on. Um, like you said, we're not too financially motivated. It's a lot more, you know, motivated by what is the largest net impact you can have, or what is the coolest thing we could possibly do. Sure. In that realm, I think I've always been a little bit more like blunt and, and calculated about some of my responses, and he always said he's always been very aspirational with his pitching and ideas. So it's nice when there was like a bit of a synergy in what we both thought about.

So how does Cloak start?

Oh yeah, well, we, I remember this happened during COVID right?

I, my version of the story is that, and how old are you guys at the time?

So I was either 19 or 20.

I was 24.

And where were you guys like in the world?

I was living in Cambridge. He was living in Berkeley.

So like a little opposite ends.

Yeah, a little bit of distance.

A little bit, right?

Like just pre-world shutting down. Okay, I think back then I was still pretty much focused on school and life, and you know, I was triple majoring, so I had enough on my plate. But RJ, you could do that. I actually only ended up spending 3 semesters in college, so that's my fun brag.

You guys dropped out?

I dropped out.

He finished his entire CS degree in 3 semesters.

I did technically drop out.

What?

No, he, he says it as a fun anecdote, but he has a computer science degree. He only spent 3 semesters in college.

How do you do that?

I don't know.

He overloaded on classes, came with credits.

Did you have any social life?

I actually spent most of it. Well, I mean, so this goes back to like, why did Arjun not go to school for CS, right? Like for me, I just kind of showed up to the midterms.

Wow.

So I like just spent the entire time hanging out with my girlfriend.

Okay. So it just came easy to you.

Well, it was like math and econ were like the things I wanted to learn. Yeah. So I wanted to front-load all the classes I already knew ahead of time so I could spend like the, you know, the glory days of college studying the hard stuff in the, in the majors I wanted to learn.

Can you relate to this, Max?

No, no, I was in college for about 2 weeks, so, you know, I, uh, and I did not get a full— I did not complete anything. As a matter of fact, they're like, uh, yeah, we're not giving you any money back. I couldn't even get a refund.

That's crazy. Well, I, I think I get— I mean, I really didn't want to college. Um, I took a gap year after high school.

The whole big part about— oh yeah, he obviously worked in the, uh, military defense contracting.

So I worked with this company called MITRE, which is like an offshoot of MIT, which is doing basically subcontracting for various arms of the government. The only person hired out of high school there, um, where it's mostly like a PhD-level company.

Yeah, so you guys both have this in common, like you're just given so much responsibility at a young age and trusted with it.

Yeah, yeah, I think that's like— I mean We talk about privilege a lot, and I think like there's a lot to be stated for just being able to have that trust, like just being given the opportunity to succeed. I think a lot of people would succeed if they were given that opportunity, and it's just fortunate that like I was given my opportunities and he was given his. Um, but yeah, I mean, I, I really didn't want to go to college, so after Exeter, I sort of— there's like a chip on my shoulder being like, I don't need college, screw you guys. Keep in mind, like my entire class went to fucking Harvard.

I was gonna say, that is like a direct funnel right into all the—

Yeah, yeah. So like basically like my entire friend group went to fucking Harvard. So I'm just like, fuck you guys, I don't need college. So I went to like, you know, get my six-figure salary right out of high school just to show that I could. So I did that. I was happy with it. You know, I had responsibilities. At some point in time, like I did some cool stuff with healthcare data and creating standards of healthcare data. And then At some point in time, Joe Biden even shouted out the work that my team was doing. Theoretically, one of the tech leads on.

So it was very, it was a very visceral experience for an 18-year-old.

But like, I really didn't want to go to college, but then I entered like year 2 of this and I was like living in Cambridge just to be around all my friends who are going to college in the area. And I'm like, I really should just go to college and like meet girls there and like have friends there.

A lot of friends were 45 plus.

Yeah, yeah, all my friends, like I was in a D&D group with people who all like had kids my age.

Got it.

Right?

Yeah, yeah, yeah.

So like—

It's gotta be lonely.

But you kind of probably liked that a little bit. You liked being kind of the youngest in the room.

I mean, I did at some level, but like the part of me that wants to like, you know—

Socialize.

Socialize and do all the freshmen in college things didn't.

Yeah, that's true.

So like, I was like on the latter end of 18 being like, I think I've like that ego part of my thing where like I, you know, I didn't get into Harvard. So I needed to prove that I was otherwise, you know, at some high level, that was all sort of squashed and I was over it.

And were your parents supportive of this or were they sort of like, what was their head—

I think both of you guys up until—

they're supportive of him, they're very supportive of him.

I think, I think moms now also, uh, come over or come around on a lot of things. I, um, I think if we could have a way, my mother probably would, would have loved early on for us to become doctors, but I think definitely the work that we've done and the experience and the Opportunities we've created for ourselves has definitely shown that, okay, we're, we're on our own path. But I think there is this element, both our parents were very supportive of us trying and doing our own things.

It's like the least relatable podcast in the world.

That's interesting.

As long as it's honest.

Yeah, as long as it's honest and it's interesting.

It's very, it's not very Indian of like our family. We're definitely like an outlier on the Indian side. It's like our parents were like, go explore, go try, go do things. They're like, some inner desire to like be a doctor, et cetera. But they were very supportive of us trying and failing and doing things. Like I, I remember when my second startup like came crashing down, like I called my parents, I was in tears, like all those different things, a very messy situation. My parents like, these things happen. Like we're here for you. Like we'll figure it out. That gives a lot of strength. I was running negative in my bank account. I remember it was such a lonely period where it's messy, but my co-founders like ran away, left me with debt. That's all in my name. And then I was trying to pay it down. So I had negative money in my bank account. And I remember going to, if anyone from Harvard remembers Hong Kong, right? There's a Chinese restaurant.

Hong Kong.

They'd give you sesame chicken, orange chicken for $10.57. Give you a ton of food and like free extra chicken wings and eat that every day because then it also lasts for lunch the next day. But I was just like doing that and then like my mom chipped in to help, like, figure out how to pay off some of this debt. And then, like, I worked through it and it was really, really supportive. But I think now I— my mom is now like, yeah, don't even be doctor. I think you guys have crushed it. Like, now I think we fully surpassed that. But they were very supportive there.

Can I just say, I think having— I feel like your parents are kind of the same way. Like, having parents that are supportive of their kids doing something that is off the beaten path is so important. I just can't imagine— like, I was very privileged in that my parents were always like very loving and supportive of whatever path I wanted. But I can't imagine like coming home and just feeling like so disapproved of.

Yeah, I think all of us here share that and that all of our families and parents have given us this leeway to kind of just try things and experiment and it's okay to fail and try again.

Yeah, I mean, I think a lot about privilege as a concept, like especially since I'm somebody who's like, you know, I went to Exeter, which is a very privileged school, and then Berkeley is obviously a very privileged institution for people. In our field. Um, something I go back to a lot is like, there's this, there's this anecdote I heard once before where like privilege is almost like shooting darts at a carnival, where if you like, if very, very privileged people are going to shoot many darts, you know, some people who get really lucky and work really hard, they gotta shoot one dart. And like some people who have like, they're the ones who are, who are man in the booth, they don't get to shoot the darts. And I think the thing that I've always found is like, what is my foundation of privileges, like having this idea that I have parents who, even if like all goes to hell, they will still love me and let me like crash on the couch. I try to keep grounded in that way as well. Very, very hard to overstate the value of having a strong safety net.

And the final anecdote before we get into Cloak to talk about parents supportive, they were not very supportive, but said, okay, do what you want. Where for my second startup, instead of getting an office, We ended up getting an office. Obviously, we rented a 14-bedroom mansion and we made half of it our office and half of it where we let other entrepreneurs live there. And where was this? This is in Natick, Massachusetts. Wow.

And you guys signed like a 12-month lease or was it like—

We signed a 12-month lease. And it was— Very interesting experience learning to be landlord. We were subletting to other folks and it was insane. Or 12 people, whatever it was. And it's too many stories. We also had like crazy parties. We had clients that come into our house. We had like, we had whiteboards, everything. But like one of the parties, I didn't have as much fun at the parties. I was so afraid of people dying and whatnot. Like some people like jumped off like on the roof into the pool. It's like Project X. Oh, there were some tech version. Yeah, one of the parties had like 400 plus people. We hired a bouncer. After the first party, I'm like, we have to have a bouncer. Oh, because like high school starts showing up. I'm like, no high schoolers, nobody. But like we had like wristbands and everything. Cool experience. I'd say learned a lot, would never do again. But like the whole idea of living, working together. I think Abhijeet and I and our small microcosm, us two living and working together. Works, but that many people, it is, it's a lot.

Fast forward. So how did Cloaked get started?

So Abhijit kind of alluded to, we came back together, but Cloaked had been kind of manifesting in my head over the coming, for a couple of years. So I worked in VC for a while after my second startup did like kind of shut down. I needed to pay the bills. So I became a director of technology at a company and also became a VC. Um, so I had two jobs. It was really cool. But in that time, It was kind of like that whole Einstein working at the US Patent Office. It was like my time of like thinking and like, it was the healthiest I've ever been in my life. Like I had been also having a lot more fun, but percolating the idea. But I started kind of thinking around what is the future of the world with AI going to look like? I'm like, we're headed into some world of AI. Nobody knows what's going to look like, mean. And 2020, this is like 2019, 2018. In 2018, I have a book called Book of AI where I started writing all my notes down. And like 2020, it's a few years away from LLMs and ChatGPT.

GPT and everything.

Yeah. So in 2020, I had started now like coalescing what the idea was. I said, I want to figure out what every piece of data about me looks like online and help me understand like my behaviors, my moods, my actions, all rooted in data. I wonder if I can somehow use this data and AI to help me live my life better. So I connected my, like my basic stuff, my Facebook data, my Google Calendar. I hacked iMessage, my banking, my workout, my eating, my healthcare, my GPS, my movement, everything about myself. I either had API integrations, I did scraping, or I did like all sorts of ways to get the data in. And I kept pulling this data and I wrote some crude models to study this data and try to give me some insights. And what I realized is my hypothesis was that it's not about volume of data. It's about breadth of data. And that actually started coming true where I said, started making, trying to make me healthier, help me eat better. And on its own, it started giving me recommendations. It said, and I set conference stretch goals, things like that. It said, hey, you missed your workout yesterday, do 15 pushups in these 2 meetings. Based on my spending habits, it said, let's cut back on the alcohol and the Chinese food. And like, this is when that time where I was like very stressed and it noticed my like, my habits there. And then, but one day it hit me. Hit me when I was at lunch at somebody and put my phone down. And then at lunch I picked up my phone and my really crude AI had a full conversation with my girlfriend at the time. It told her I love you. It sent her memes. It went back and forth without me realizing it. This is 2020. And I just stared at it. I said, this is crazy. But it hit me in that moment. I was like, okay, we're headed into some world of AI. Something's going to happen real soon. And so there's going to be two big fundamental questions we're going to have. It's like, well, all this data that is about me, I don't own any of it. And it's all being controlled by all these different people. What's going to happen there? And two, whoever makes this future of AI, Facebook, Amazon, Google, whatever. I was like, well, I'm not, I was not a big privacy guy, privacy conscious, privacy aware. Like my fun anecdote is in 2006, when Facebook started picking up, I remember I had a fake name on Facebook. Because I'm like, what if this Facebook company becomes like a big thing? And People started looking at our profiles and different things. And my friends are like, you're insane. This is stupid. But I, like, and then I was a little bit conscious, but I was like, well, how are we going to get lost when all these companies and AI start to get every piece of information about ourselves? So I said, the biggest problem we're going to have in a wave of AI is going to be how do we tackle security and privacy and true data ownership? Where it's not gonna about being about hiding, it's gonna be changing the way people interact with who you are. Mm-hmm. And how do you solve that problem? And so I didn't have the answer yet, but I start, like, I, that's what it kind of hit me on the opportunity. And I start the sketches of the idea and what would become Cloaked. And then I called Abhijeet and I started pitching to him. And then he said like, I think that actually would work. And I was like, okay, I'm on something. I gotta get dig deeper. And like, that was my, um, like That Cloak began and like the part 2 of it is like, I was a big runner at the time. And then I was thinking about enterprise and how could we build an enterprise solution? And then I was, when I was, but I'm like, I spent 2 months ideating on enterprise. I worked on it, but I was on a run one day and I was like, this is gonna suck. I can't change businesses overnight. It's gonna take forever. We're all gonna die before we change every business, how they work with data. And I was like, well, what if we could work with consumer? Like, that'd be like, I wish we could figure that out. And then as I started running and I was like, wait, what if we did? And then I started sketches about what a solution would look like, how you get started. 'Cause I know people like, I know because of privacy, how do you actually make that more feasible? And then I started getting the inklings of the idea and then I started telling Abhijeet and he is like, this works. And then we started like, let's make a company. Let's try to fund. Like now we didn't think about fundraising, but let's figure out how we build this company out. And that's what led to beginning Cloaked.

Wow.

And did you kind of naturally know you guys were going to work together on this, or was it— were you kind of taking a gamble, like maybe he wants to do this, maybe he doesn't?

I've always approached this idea where I like to be left alone to just do the fun nerdy thing. So I've always had this idea of if I come up with some nerdy idea, I'll let him figure out how to make it a business, um, which I think ironically it's been a lot less that, a lot more collaborative than I expected. Over the last few years. But, um, I, I mean, I imagine with your past experience and the fact that this was still, you know, the summer before— the summer where everybody came back together at home. So when we were pitching each other these ideas, we were actively just in the next room together, and we were like, hey, check out this cool thing I made. And I'm like, oh, I can tinker on that. Let me, let me add something on top of that. So it naturally emerged.

I think we played a lot of ping pong and like we're brainstorming ideas and talking about like What if it can look like this and think about this? And, and I actually teach, I teach our teams this for like, they're like, oh, we gotta do like a strategy full brainstorming session and sit in front of the whiteboard. And I was like, I don't know, a lot of my ideas have come from like not actively trying to ideate, but like playing ping pong, like walking around doing something and like, and then like starting to think around it versus like come up with idea right now type of thing. And that's how we started flushing a lot of the business.

And so it just starts with you two?

Yeah, just us two. We had some, I had some contractors before that were working on that, that what I call the data box, which is where all my data was in. One of those contractors eventually later joined us as one of our employees full-time. And then we also H1B'd him here from Africa.

Wow.

So that was a cool, fun story.

That's awesome.

Yeah, I do kind of, I, you know, shout out to Arnaud.

Right.

Yeah. But it's fun that there's some people who technically, because they're in the ideation phase of Arjun, they've been around from day zero.

Founding team.

Yeah. Yeah.

And so this is really the first time you guys are, are you guys planning to raise venture going into the future?

No.

No. Really?

We have no plan of that. And I actually don't really know when. Maybe you remember this more accurately.

I remember everything.

I just remember Arjun approaching me one day being like, hey, here's some forms you should fill out for some like fellowships or whatever. And I'm like, that seems like a lot of work. Like, I don't want some people managing us and micromanaging us. So he's like, just fill them out. And I'm like, okay, fine, I'll fill them out. And that, I think that was the first thing that led to our first conversations that led to our first checks.

I don't know if you know, but I remember, or I can't remember, we talked about it, but I applied to a lot of government grants and different grant programs and got rejected.

With this current business?

With Float, yeah, yeah. I was applying for like $10K grants and $15K grants and got rejected. But in that process of researching grant programs, we discovered one of our, now one of our lead investors was doing their own fellowship program. And I found their form.

What's the fellowship?

So the company's called Human Capital, one of our investors. They had something called the Delta Fellowship, which was like a non-dilutive $50K grant they'd give for early-stage startups. And I found it, what I found most fascinating was their application process. Because they didn't ask about our business. They really wanted to understand who we were as people. And I was like, oh, this is really cool. But like, there was like a month, so I remember like I applied in the beginning of like July or something and the deadline was end of July. And Abhijit finished the application at the last day and I was like, Abhijit, finish the application. And that, and what's really cool is that our investors that now they're on our board, we're such a good relationship, but they, when they, they heard our, our, what we're trying to do as Cloaked, which is a different, different name back then, but they, they actually said, this is really fascinating. We've been thinking about this space and said, instead of the grant, would you be interested in us doing a pre-seed check? And when we, they gave us offer and we're like, oh, this is actually pretty good terms. I was like, from my experience of being a VC, I was like, I don't want to do VC. But then after seeing the terms and I really, we really liked them. We said, you know what, let's do it. Let's go on the VC track. And I think it was the right move.

I remember, this is a really funny anecdote, but I know you were a VC, but I think we had no idea, like you were an East Coast VC.

That was East Coast VC.

We had no idea like sort of the attitude of West Coast VC. I remember when we did our pre-seed round, we tossed in a number, we tossed out a valuation number for our very first check and they were like, what if we did it higher?

Yeah. Yeah.

We were like, oh, just give us this much. And they're like, What if we just like double that? 'Cause I think that's fair. And we were like, oh, okay, sure.

Yeah, that's great.

Which is like, I mean, shout out Baris and Arman. They've been our partners for a long time. Yeah. But it was an interesting, like just several, several digits later in funding. Like we've done a lot more since then. But thinking back to that very first day, it's funny how little we knew what we were doing.

And where's the company? So you raised the pre-seed, are you guys in market yet? Have you not launched yet? What's going on with the actual product?

Yeah, so Cloaked is fully in market. We've launched, fun, and a fun fact is, We just recently announced our Series B funding.

Awesome.

Congratulations, man.

Thank you. It's been a really big time journey, but as a company, we've been growing pretty rapidly. We have over now 300,000 users.

Wow.

Scaling rapidly month over month.

How did you guys get to 300,000 users? Like, well, clearly, I mean, obviously congrats on the Series B, but there was obviously a road to get here. Maybe talk a bit about like, how did we get to where we are now?

Yeah. So we—

I mean, it hasn't been easy.

It hasn't been easy. I think we've learned a lot over the past 4+ years. 4 or 5 years where privacy often feels like very tech savvy, very also male-centric. And truthful, that's where we began. We've had a couple 20,000+ beta users that were really heavily using our product, very tech-oriented and very deep into privacy. And we've been scaling and building and improving Cloak for them. But then we realized, especially in the last couple years when 2024, the real, when it hit us was that the world is changing where it's not just around building really cool technologies. We are really powerful in the way we're doing approaching phones, emails, and nobody can do what we're doing with Cloak Phone. But, and we're now getting really excited in the coming months around our launch of our Cloak Pay product. But the issue is that we need to make money. And so a couple years ago, we ended up realizing that We have to crack the mainstream audience. We have to make sure how they understand it. And so we started dissecting the problem and realized that people do care. And we've always known this, people care about the problem, but it doesn't seem intuitive, seem like, well, what, what's the point? It's all hopeless, right? We started getting obsessive about how do we present and share what Cloak can do for you. And we do this via paid ads and marketing. We built a really strong funnel. Where if you hit our checkout, for example, checkout page, you're 25% chance or somewhere on the vicinity of converting to paying customer. And so, and the idea is that we got really good at that funnel process of like helping you identify the core problem you're feeling, whether it's some sort of safety concern, something around spams or scams, or maybe it's around being surveilled and really kind of drilling into that message. Then showing you how bad the problem is. We, We kind of got some viral moments and things where we've built this really cool system where from just your phone number, we can show you the extent of your problem, where we can show you your Social Security number, name, address, family members, and soon showing even passwords, compromised breaches, all from just that phone number. And people don't believe that. And when they see it, it's like, it's one thing to say, oh yeah, my information is exposed. When somebody tells you on the phone, yeah, it's like, but then when you hear your social security number, you see it on the screen, you're like, oh, I didn't realize that. And that's where the problem lies, where we protect things like our passwords or social security numbers. But the reality is you're leaking your, the most important detail, your phone number or email, which ties back everything about you. Because you haven't changed that piece of data. It's the same thing you've been using for decades.

When do you think you guys first got product market fit?

I mean, it's a good question of what is product market fit. I think we obviously have a business that has positive, the machine, the growth machine is positive now, right? So at some level that's product market fit. But what is 300,000 people versus the world?

Yeah, I mean more just like when did you see that customers really wanted this? Forget making money on it, but was it kind of immediate? Did people have to be convinced? You said you had 20,000 beta users.

Yeah, so I'd say from day one, one of the things that I've always believed is always launching. So we, in early 2021, we actually launched Cloaked, put out there, put about the product, we actually started seeing our, we launched like our first set of 25 users and people started using it right away. Like they ended up, somebody had organized like their shopping list. People started doing some home hunting or apartment hunting, even our crudest UI that I had made. And like our new front-end designers were like, ah, that looks like horrible. But people are using what I, the original UI had made and it started getting value. And I think the idea of privacy, of being part, making me feel safer and a bit more in control and being a bit more organized was starting, the thread was starting to show.

I see.

And then for us it's just been, it's been a journey of improving the technology and cracking what experience works. 'Cause it is a little hard. It's a hard problem to tackle. And so I'd say we, we're not even perfect yet, but we've been getting better and better. About how do you start from nothing and build up from there?

I'm just going to talk about 2024, where I think a really pivotal year for us in general. We've chatted about this sometimes personally, I think, but, you know, this is the moment you're talking about urgency, like we have to make money, but what is the, what's the larger context around that, right? Like this is a few years after our A, you know, money's not infinite. Towards the end of the year, right, we're running towards the end of our runway and we're still sort of in this inventor's dilemma mindset. Then halfway through the year, we start talking about, well, what if we do an extension round? We'll do this thing or that thing. Our investors actually sat us down. They said, no, you're not getting any more money. We're not going to let you raise any more money. You need to feel the pain. Sit there and feel the pain.

Yeah, yeah, yeah.

I remember like we walked away from that being like, well, fuck, what do we do now? And they were very clear that like, it's, it's, there's no shortcuts here. So this is when me and Arjun like said, what do we not know how to do well? What can we do this well? I think this is, we're talking about product market fit and like marketing is the word here is we had a crude team around marketing about that time, but we fully took over that entire function. I remember I spent every minute of my day like learning how every step of this funnel is supposed to work, how all this was supposed to work. We found one of our team members, we realized what talents. Yeah, we elevated them up into positions and we really took it over. And within like an 18-month journey, starting from like Q3 of 2024, or even like 12-month journey, we just had to be completely different types of founders. Like we had to shift from technological founders to like growth founders and figure out what it means to be that in order to even like survive, let alone meet product-market fit.

Did the company almost die when that happened?

Arjun, I think, is very good at you know, there's always a strong sense of safety, right? I don't think we ever felt like this is the death's door. Um, but I think he probably felt that way and I felt that way. Um, where it was, I mean, money is a real thing. There's a finite amount of it.

Yeah.

I remember our phone call was about a year ago.

Uh, so that's late 2024.

Do you wanna remind on the day of you announcing your Series B, do you wanna announce what our phone call was about a year ago?

Yeah. So ending 2024, I called, uh, Matt Carley. And we had a great chat around. I was like, hey, so I'm about to commit to spending where we haven't figured out around yet. And he brought up a really good point where this term of burning hot, we were spending more money than we, and we were trending towards spending more than we had in our bank account.

And that month, that month, let's be clear, that month you were going to spend more money than you had.

Yes, especially. And so like we were talking in November and December, I was I was projecting to spend more money than we had left in the bank. And he had really sound advice. He's like, look, you can, if you measure yourself, you can scale, you can reset and figure it out. And I was like, but everyone's, the number is going up. Everyone's seen number go up. And so I was like, I can't let that hockey stick curve go down. And, and so we went back and forth and I took it and I like respectfully disagreed and said, you know what, I'm gonna run with it. Yeah, but I didn't have an answer yet around the fundraising. And we got our like lead opportunity December 27th, 2024. That was, and we, we pulled it off or post-Christmas and I'm like, oh my God, we're gonna see 2025. Um, but I kind of had an innate sense that like I didn't have an answer, but I had a belief that I was going to figure it out because we knew something was clicking. We could feel it. We just like, we are unfortunate that we're a little late in the amount of money left. And in the fundraising climate, everybody probably remembers '24 was very late, was very difficult post the administration change. There was a lot of uncertainty, especially with AI and a lot of companies were stuck like, what does fundraising look like? And I think we started out with a pretty decent outcome between our A and B. And we didn't get a down round, which really helped us. We got actually an uptick in valuation. And I think that, and our existing investors came in and new investors came in. And a lot of people said no, had no nonstop being told to me. Even in this process, saying the Series B, it's like, oh, like while I'm executing the Series B, a different investor who we hadn't chatted a while called to tell me no. And I was like, Sounds good. Like, let's stay in touch. Like, I am signing a term sheet. But I think that the belief it's going to happen was like, I knew there's something. And I know that I have to make some changes come January if things don't happen. But we're born and raised from Massachusetts. But, and when I say about Boston, it's always about how do you minimize risk and minimize loss. But why I think California's done really well is how do you optimize for success?

Yeah.

And I think that was the moment where I said, we're going to optimize for success. If I keep minimizing loss, like you're minimizing a downward function.

You play to win, not to lose. You're not playing not to lose. I will just say after that phone call, I remember thinking, wow, well, you know what? That man is convicted. He will will this into existence. And look at here we are today on the other side of that with the Beast. So man, guys, congratulations on that. Really, like that is, you know, again, just really cool full circle moment.

Cool.

So yeah, you want to just walk us through the overview of the business today?

Yeah. So prior to our B, we raised over $50 million and that's really got us to the point we are up into this moment scaling, getting to closer to 300,000 users or getting beyond that. And it's been awesome instrumental where we've solved a lot of different key problems in the business. But now We're about 60 people today and we're looking to probably get to over 100 people with this fundraise. But I don't want to grow like a lot fast, like, or that, or much past that. I think in reality, scaling and like being disciplined as we scale has helped us a lot versus like, let's go hire 50 people right away. Has allowed us to survive all these different junctions.

What do you think, now having this quantum of cash coming, and frankly, that you've raised to date, what's changed within the company for you over the last few years, you think?

There's a lot of interesting anecdotes I'm learning as I talk about reshaping the company culture and everything. One phrase I keep on going to a lot, and he'll be sick of hearing this, but I read somewhere that when you build systems, you build them to scale 10x with the idea that you might need to throw it all out between 10x and 100x. I think a lot of the stuff we've built, whether it's like the company culture, the way we do engineering management, we do like the— we built it about 10x ago, right? We built it at 10, 20, 30,000 users. So I think we're going to see a lot of shifts in how my— how the team actually operates. I would really love to see us be a forefront engineering culture that is able to contribute not just to like our company, but to you know, open source and everything as a whole. I think the way we want to build is going to be a lot more based off of individual creativity. Um, I think there's a lot to talk about in terms of just with more people, there's more layers, there's more management, there's more focus. Um, why? It's— we've always been really comfortable with like reorganizing teams on a whim, on a quarter. Um, and I think as we have more people, I'm gonna have— we have to figure out exactly what that looks like. And I have some plans, but obviously we'll see what the growing pains are.

So the team's evolved a lot over the years, people coming or going, or— I think right now I really like everyone who works at Cloak, and I think that I want to figure out how we keep that as we continue to scale.

That is one of my— like, I, I just— I'm very, very happy with the team we have. They're just all killers and rock stars and And like part of my goal in 2026 is like, I want to make sure I can let them cook. I keep on saying this a lot. I'm like really smart people and like almost all the brilliant things that have helped us succeed have been through, you know, individual people, whether it's me or Arjun or other people on our team, just having some spark, some whim that they explored and they cooked on it for a little bit and that turned into, you know, a completely new segment. Or a new product vertical that we've been relying on a lot. So I really want to see how I can maximize that kind of energy because I just want to let smart people cook.

I would love to hear what was going on for you guys in like your personal lives as these rounds are happening. You know, you're raising all this money and then, you know, burning a lot. I'm sure that there was like a lot of really stressful moments, but I'm curious, like, just to paint a picture for folks, like, what's going on at home?

Yeah, man, it's not been easy. I do think like one thing that being a founder or even working in a startup requires is living a very holistic life where there's not a large separation between what you do, who you spend time with, and like the work you are spending time with. That's actually always been very hard for me because I've always been someone who's very, you know, I, I, I, I, I have a lot of, like, I place a lot of emphasis on my personal life and the people in my life. I remember during, I think this was after our A, but still pre, you know, this was still in the, like, the chasm of uncertainty when we were building a lot and still not trying to figure out, like, still haven't figured out product-market fit. No, I ended my longest 3-something-plus-year relationship and then this is still 2022. Where it was still COVID and people hadn't start like left the home yet. So I remember I'm, I've discovered during COVID that I'm actually extremely extroverted. So I like being stuck home alone with nobody around me made me realize that like I'm happy when there's people around me. So it was like this incredibly hard situation, both just COVID and then breaking up with in COVID. I remember I had, I had none of my friends, I had none of my boys, I had none of my like my, my, my close people to, you know, do the process of grief with. And we talk about me and Arjun's relationship too. Like, at some level, at that time, him and I were more colleagues than we were, you know, close friends. So I wasn't even going to him to necessarily grieve. So it was— I remember at some point in time, I had to take like a whole month or two where all I did was just rot in bed and do nothing. And to Arjun's credit, he just said, listen, take your time, I'll hold on the ship. I don't, I don't care. We will handle it all. I'll handle the team. Just take care of yourself. Which is like something you get when you have a partner you trust a lot. But the consequence of that, actually, I remember was I one day I decided, you know what, I need people around me. So I booked flights for that next morning to go back to Berkeley where my friends in college were still staying. And I slept on a couch for like 6 months.

6 months.

6 months of couch surfing just to like be around people and be immersed in a social environment. And actually we raised our entire A during this period. So Arjun came to SF for part of it too. But like I remember I was taking— I was like sleeping on the futon of my friend's apartment and it would be 6 in the morning and I would wake up from— I'd wake up on the futon, I'd get dressed, go to a small little dining table do a phone call for our A, and then I'd go back to being homeless in a futon.

This is before the A. Yeah, yeah. Like I say, personally similar. I think I broke up with my girlfriend at the time that led to the idea of Cloaked right before we raised our pre-seed. I think the biggest kind of key social or personal things for me were really kind of— I'm usually more personally pretty regulated and more moderate. but I, before we raised our A, we finished our C, we had finished our C, it's been a year coming into 2022. I remember I wrote myself like a note in like December and had a long chat with our father. I was like, I don't know where the company's going. I don't know what we should be doing. Um, and I, my father and I talked, man, he said, I think you should go to San Francisco. You should go be there, learn, like, because COVID's still there. It's like, we still didn't have like and I think we just got our vaccines. And so come Jan 1st, I bought a one-way ticket to San Francisco and we had no plan, nothing. I was like, we didn't get an apartment, Airbnb and figuring it out. But I wanted to be in the world to figure out how do we get the next chapter of the business. And I told myself, I wrote, I still have that note. It's like, hey, Tarjan, 3 months from now, I hope you've raised a Series A. I hope you figured all of your stuff. Like, I hope you're in a much better mental spot than you are now. And like, and going to San Francisco is definitely also took a big toll where a lot of our team is East Coast, also like on the Europe, etc. And so I, we actually were starting the day at like 4 in the morning. And it was hard to get up at 4 and then start to sync with the teams. And then the day would end around 5, 6 PM. Then you'd go get dinners or events with investors and then come back and like the day would end around 1 AM. And I remember breaking down late Jan, calling my dad and like crying basically. I was like, I can't do this. There, I am working. There are no more hours. Cause I called him at 2 in the morning one day and I'm like, I started at 4. Like there, there are no more hours left in the day. Um, and my dad's early riser. So it's like 5 AM his time. And he's like, you got to power through. And I was like, okay. He's like, and I was like, okay, I got to figure this out. So we actually ended up getting our Series A the next month. And then I slowly started liking San Francisco. But the one thing that was really painful, what Abhijeet alluded to, is that both of us like being a lot more holistic. And being in SF, everyone's in tech. Now I love tech. I love entrepreneurship, but Everyone's in tech, everyone's in VC or private equity or some tech related. And as everyone knows in founder, like you're in like founder mode on, like when you're talking with people, talking to investors, I was just on on mode all the time. And there was just no reprieve. And I remember hilariously, I was with a partner from Redpoint Ventures. She was like, we're going to like a warehouse party. And like people always like talk about, oh, creepy guys hitting on girls. What was not, well, that was not what was happening. We, I was with her and we were like, at the party, guys coming up to pitch their startup ideas to her. And she's like, ah, it's normal. I'm like, oh my God. Like when does this ever stop? I like, eventually that rest of the year we stayed in San Francisco, started getting adjusted, we got our own place. But it really took a toll to the point where I remember Abhijit, like, also had it like broke down again post-Series A where it was like, we are working so many hours. And I knew Abhijeet, like there's no outlet that's coming in. So one day we, I came back from an investor meeting and Abhijeet was working at home and I said to him, I was like, hey, let's get in the van. I'll get an Uber. And he's like, where are we going? I said, just hop in. So we hopped in an Uber and I took him to an animal shelter and we adopted two cats. 'Cause I was like, we need, we need, like, I was like, I, I could see him breaking down. I'm breaking down. Let's like do something different.

Sure.

And so we got our two cats and we, we still have our cats. We flew them to San Francisco, but at the end of the year when the world started opening up, we thought about what does the culture we want look like? And I, I love in person. I, I work really well remotely. I'm big for remote proponent, but I know that ideation brainstorming, as I said about the ping pong between Abhijit and I, it comes from interacting and seeing each other. So the moment we, our investors also nudged us, like, think about in person. And I said, okay, if you're doing it in person, we're going to try it. We're going to try New York. I don't want to do San Francisco. Let's try somewhere else. So take a one-way flight to New York. And then we started figuring out what New York would look like. And that has been a huge boon for our mental states, our social lives.

I'm the biggest New York over SF advocate. In general, I'm a very big in-person advocate, but like, I just love New York.

It's been way more— I, I realized I love Broadway. Uh, I didn't know this. Um, I will join anyone in a Broadway show. I have so much fun going to Broadway shows. Um, but I, I think New York is just way more holistic. You get so many different, uh, avenue to avenues. And we go to SF all the time for work, so I, I feel like I'm not really out of the picture loop there, but, uh, So that was also a big mental and social uplift for us being here.

Going back to some of the raises that you guys were doing, did you have any specific stories from raising from some of the folks that you guys had raised from? Your investor list is pretty star-studded. Were there any moments you can think back to where you were nervous?

We definitely have a lot of stories fundraising-wise. As I started alluding to, Peter Thiel has been an investor in Cloaked. And he had, we actually, he invested in our seed and then also invested in our A, but we flew to his house in Florida, but we were in the middle, we were in San Francisco and we were, we were in the middle of our A process. Peter's team said, oh, let's go, you should go meet Peter. And we were like, this was like Wednesday night, San Francisco. And we had to be, we had a meeting in San Francisco either that night or the following thing. So we flew to Florida to then fly back to San Francisco for the day. Like, yeah, the day, like, we flew to Florida and then flew back that same day from their meeting. Um, but we went to his house in Florida. Um, and, uh, what I'll say is that Peter is like, he has such a commanding, intimidating aura, but he's a very kind human being, which we didn't expect. Like, um, but we were in his house and he has basically his two houses, one that he lives in and one that he has meetings and works in. Um, so we were, we were in the second one, but he had like like, we went in front of his house and we're like, is this the place? And they're like, people who— like, there were vans, people who were like, uh, like bodyguards sitting in front. And they're like, why are you here? And we're like, we're here to meet Peter, uh, pitching something. He's like, wait here. And then he goes inside. Then he's like, all right, come in. And then we'd come in. Then it was like funny, like, it's like, uh, he had strollers for his kids on the side. Then he had like, uh, tables. And there's a staff is like with like a, like a waiter type of guy. Like, what would you like to drink? And we're like, uh, water. Uh, and then we were ushered into a room. Our partner that works with Peter, uh, was there in the room and all three of us sitting at a circular table. And I still remember the funniest moment. It was like, we were this fourth empty chair. This, we realized Peter would sit there and Abby just like swapped with me so that he had me sitting across from Peter. Um, and then, uh, Peter came in. He was wearing gym shorts and socks and like drinking a protein shake and he's like, let's get started. And he's like, didn't say like hello or anything, but throughout the whole like pitch process, we pitched Cloak. We also demoed Cloak. He smiled, he laughed and he like really loved the product. And we had a really, and he asked really thoughtful questions and realized he's very nice in person. Like you see all the media and all this stuff, but it's actually a pretty kind person. But obviously very thoughtful civic questions. But after the meeting, Peter left and then his business partner was like, Peter never laughs. That was a great meeting. I was like, oh, good. And then we found out later, he's like, yeah, Peter wants to invest and put in money. But it was, and he kind of mentioned, he's like, people talk about his investments in Palantir, et cetera. And he's like aware of the problems that have been created in the world. And he's like, like, and he left Facebook, but he knew what a big problem Facebook's created around data and tracking. It's like, so a lot of money he's made from that whole process. He's like, well, in the next chapter, he left, like, I'll make a lot of money fixing the problem. And he did say one quote, which is really interesting, which stuck with us forever, was Peter said, and this is what we talk about in our product market fit. He's like, Arjun, I think if you sat with every human on earth for 5 minutes, they would become a Cloaked customer. You need to figure out how to turn that into the way you sell and position Cloaked in the market. And so that was like always stuck by us. It's like, we gotta figure out how to sell and position Cloaked. That was a really, really good story. We also had like crazy investor stories. This one I won't just name any names, but like we were at dinner with an investor and that dinner, that it was like, and like a 3-person dinner where they, we spent like like 3, they spent 3 grand on the dinner, which is insane.

Yeah, my first time ever legally drinking alcohol was like a VC dinner where it was like a $1,000 bottle of wine. Yeah, because I like just turned 21 and this was like a, you know, a celebration, a celebration dinner that the VC was in town and they're like, oh, let's just, let's do all of the, let's do all the fancy things. And I'm like, okay, this is way too high of a standard for to set. My palate is not nearly refined enough for this.

Yeah. And it was a weird, like, that investor, he tried to get us to take their term sheet or take their terms versus another investor. They're trying to cut out, getting us to cut out other investors. And he was also like starting to lean into like ethnicities and like different things. And Abhijeet, he got Abhijeet to drink a lot. I started to like realize what was going on. So I was like kicking Abhijeet underneath the table because he was like starting to get into Abhijeet. But Abhijeet was like, they were both wasted. And like, he got wasted, Abhijeet, like, he made Abhijeet drink a lot. And then eventually I like straight up just like kicked Abhijeet hard and like I pointed to my phone, I put the phone, I was like, go to the bathroom. And so like he got up, he's like, I'll go to the bathroom. It's not like I reset the, like, I reset the conversation, uh, because he was like, you usually like, uh, underhanded like type tactics, but it was ended up being very, very, we ended up working out well. Like, and it's like nothing, we didn't end up going with like that person, etc. But it was a eye-opening experience. Whatever, Jason. Yeah, during our process, we went to Sam Altman's house.

It was funny. It was like 6 months before ChatGPT launched. At this point in time, he was still only just the YC guy, right? He was just a guy who used to be in charge of YC. And we had dinner with him.

Or was it ChatGPT 3.5?

3.5 was there, but like, you know, the most impressive thing that had been done to date was, you know, but yeah, we, you know, through some mutual seed investor partner of ours. We all had dinner at his house, and I remember meeting him, and he was talking about how he had solved AGI and all this stuff, and he was on the verge of, you know, super intelligence. I'm like, this is all a load of— like, I don't believe any of this.

But it's a cool experience. It's strange. His house is, first of all, beautiful. Yeah, I mean, you see in San Francisco, it's like a Japanese oasis in like a steel, like, uh, jungle type of feeling where You go up like, where does this— where are we? Um, and in this big house, he was like in the corner of his room, like, like, like, yeah, he sat like—

you guys know, um, this is anime Death Note, or there's this character named L who sits on his chair like on his toes. And I remember Sam Waldman sat exactly that way.

Really?

And I'm like, is this— I could not tell if this was like performative or real, on the balls of his feet. Like talking to us. And I'm just like, this is incredible.

There's just 4 of us in the room. It's us 2, one of our investors, and him. And the thing that I still remember is like, we, we pitched Cloak. He thought it was cool, but we were still early stage. But he, um, he talked like, uh, he's talking to our investor about his main interest in investing, which I think he's like, oh yeah, just like everybody else, like my main, my main 2 focuses are nuclear and living longer. Like the only 2 startups I'm investing in.

Yeah, take What about the time in the company where you guys need to figure it out?

Yeah.

We're running out of money.

I remember that time period very clearly. We realized that we have all this great technology. We can't just keep going down the privacy audience. Also, one of the companies in our space had absolutely started to fail, which was also VC-backed. And they were really squarely fighting with like Proton and the privacy audience. The team had started kind of starting to tinker on changing the experience and like starting with like data removal as more of the focus. But one of the things that I had then started to do like a side quest on, we had learned from an ad we had run like earlier last, the year before, where I had an ad where I was showing another person like, hey, you know, adjust your phone number. Like somebody could find out all of your information. And I was just using, I was showing from the dark web, like people's names, SSN and all that. And the ad performed really well. But one of the things I remember me and that marketing person was like, dude, it'd be so cool if at some point you can actually make this like a tool. And I was like, yeah, I don't know how you can make this a tool. But like, and then what I remember the first part of 2024, as a team started tinkering with like data removal as a way to get people in, I was like, let me go side quest. So like, can I go from SSN name, phone number to SSN? And then so I started studying a lot of data brokers, studying a lot of information out there. And then I started finding a way that that path of combining the data and presenting that as Sen and all that information. Coolest moment was when one day we actually were at the office late night and we were sitting with one of our lead PMs and one of our VMs and we were sitting down and talking about the idea and he's like, like, it'd be sick if you could just like call a phone number and hear your name, your SSN, et cetera. And I was like, well, we could totally do that. And so like, I started connecting the system. I hooked up a plug phone and we called it and we used just like a basic voice and just said, hello, your name is blah, blah, blah. Your social security number is this. Your address is this. And we're like, oh my God, this is sick. And so we turned both the phone number experience, the calling and the idea of typing a number and seeing else experience into that part of the funnel. And we, we had, hadn't figured out the rest of the funnel yet, but just launched that to see how it would perform. And it was moving like crazy and like people were starting to pay for us. And we, we dropped our price down to like $5 or things just to just like isolate all the variables. Would this work? And then we saw that it was working. And this is when we had taken over marketing. And when we saw that was working, we just double down. Let's build the whole funnel. Let's flush out the product experience. Let's make this all work. Let's add all the transparency, show all the data brokers that the information is coming from. And it then really clicked all together. And it came down to philosophy around like, uh, we called it identify, remove, protect. But the idea is like, identify the core problem that somebody's facing. If it's around scams, if it's around spam, or, uh, data being exposed, compromised, or being surveilled, then take action in the moment. Like our goal is like someone should get value in day zero right away from signing up for Cloak. It shouldn't be like, oh, like cool, now you can go figure out how to use this thing. And then protect is like Cloak is also an all-in-one solution. It's not just a single tool. That became the foundation of our app. And then very quickly, if you look at our entire industry now from the big names like LifeLock, etc., Every single company in our space is just a copycat of Cloaked. Like, like from, it's pretty bad where like some big name brands that are like multi-billion dollars, like ARR, have like taken our ads and just changed our logo to their logo and just ran them. And there's companies that just now have cloned our landing pages, our page, like everything. We think about it and it's like, oh, like how much should we be concerned about it? In reality, we have been creating this and understanding this and tinkering on this. So I think we're going to keep evolving. If they're just going to copycat us, well then good luck. And I think that no one's really figured out how to connect all these dots really well in terms of really meaningful experience. And because we've got like, I nerd out with Abhijay and the team about deep privacy concepts, infrastructure. And then also we talk about how does this experience make sense for the customer? I think we're in a way more beneficial and like a spot to have an unfair advantage because everyone else kind of looks at this as like some marketing game or it's some deep tech problem, but you have to balance both. We are a company that's really obsessed about customer experience and really like Abhijeet is arguing about marketing copy the other week of like, hey, we want to do this marketing copy right. And then we nerd about how do we do zero-knowledge encryption and do all these principles really well. And that puts us in a really unique spot. Both very technical, we're both generalists. I think I'm the go-wide guy, Abhijeet is the go-deep guy. Right? So I kind of got the ball rolling, got in this ad foundation, how this work. Abhijit took this and ran a million miles. Like they would wake up and get obsessed around what word shows up first.

Okay. So you guys obviously just raised your B. Looking back on the journey so far, what have been some just like really key lessons?

People always ask investors, say like, hey, would you do anything differently, et cetera? Even team members think about like, oh, what would you differently? I think everything we did was necessary to get to this point. Say maybe I could shortcut some things like optimize 6 months roughly or things on that. But the lessons and the way we now have command of the space, the command of different customers, we had to go through this process early on. Even if I came up with this breakthrough ad early in the beginning, we didn't have the foundations, the rest of Cloaked to then give them a better solution. So I think it was like necessary to go through these motions. I'd say Lessons that I wish I could like share earlier is that it's a bit cliché, but when you think about the team, I think Elbij and I have really good different philosophies and he's really good dynamic where I'm a bit of a coach to try to help level up people and Elbij is really good around identifying like this person isn't a good fit right now or isn't in the right role. And I think maybe having some like you should really index on don't chase clout and whatnot for hiring team members, et cetera. Really people who have a balance of they, they want to get into the grind, they have the hunger and they have the capacity to evolve rapidly. Like that is really indexed on when you're like trying to figure out PMF, like everything else doesn't, nobody's going to, you're not going to hire some super strategic smart guy using the crack PMF for you. That's not going to happen. You're going to find like the hunger and the evolutionary capabilities are going to really win in that journey.

I think it's really hard for me not to attribute a lot of like, I mean, we've made a lot of mistakes, a lot of mistakes, and I just, I can think just countless of things that, you know, there's always a push and pull between, you know, trust, like delegating and trusting your team versus like reining back control, and it's really hard for me and my personal philosophy not to attribute a lot of mistakes to like my own personal failure. Like where there are things that I delegated out because I wasn't able to do them versus I delegated them out or I didn't manage them properly, right? I think this marketing thing is one thing where I wish like we started off as very technical founders and that was our primary skill set. And you know, it's a very common trap of technical founders to invent dilemmas themselves up to running out of money. And like, could I go back 4 years ago and tell Abhijeet then to like be better about learning product-market fit and marketing and be more obsessed about the data? In general, like a thing we learned was to be more obsessed about the data, right? I probably should say all those things to me from 4 years ago, but it did take like a couple years of failing at it to learn that. I said before, like one of my core pathologies is like this imposter syndrome of like knowing too much about what you don't know. I think that held me back for a long time in my, in my career. It was like I was always too aware of what I didn't know and I was too afraid to like venture further than when I felt like there were people who knew more. So sometimes I would lean on, you know, I would try to hire a rock star and then lean on that rock star and then something would be something would go wrong. And then ultimately, right, like it's up to me to fix something that maybe I should have been involved in earlier. So there's a lot of stuff about like individual responsibility that I've had to learn on my own and like learning when to upskill myself versus when to recognize who I trust and deputize to. And I think everyone will have to go through that.

I think there's one thematic thing that I had mentioned when we— I gave a Maker Talk a while back around fundraising. But I think it applies to the business as a whole, which we're really embracing. One of our key investors told me this, and this is after he, we pitched him for 45 minutes and he pitched me back cloaked in 2 minutes. And I'm like, wait, that sounds sick. I want that. Where he told me the phrase, ditch the deck, tell the story. And I think fundamentally that has really helped me think around, and it's not just around fundraising. I think it's a big advice for fundraising around You should be able to tell the story of your business, where you're headed, what's going on, what's working, why is everybody else looking the wrong way, and really put that as a really strong story. But you're telling a story to future investors, to your future employees, to existing team members, to customers. And that story is something you've got to keep sharpening. And like, and I know enterprise got its own journey, but like enterprise also the same way. It's like, We've learned now after bungling enterprise for a while, what our story is in enterprise. And that's actually been starting to click. And I think that's been our biggest lesson that I had probably, like if 10 years from now I talk about us sitting in another podcast, like, oh, a long time we'd say, it's like, well, the moment we started realizing that everything's a story we're trying to say, we just want to make it a story worth telling. [MUSIC] [MUSIC]