Aakash GuptaCollege Dropout Raised $20M Building AI Tools | Cluely, Roy Lee
EVERY SPOKEN WORD
50 min read · 9,947 words- AGAakash Gupta
How are you guys prioritizing what those engineers work on together? Are you guys building a roadmap together on some sort of cadence, deciding sprints, or any of those things normal tech companies do?
- RLRoy Lee
I feel like it's pretty obvious when you have so many users. Like, literally, when we started Cluely, we said, "Let's build the most general version of Interview Coder." We built Interview Coder for everything, and we've given it, like, a very controversial marketing flair and called it Cheat on Everything, and now we have, like, literally millions of requests coming in a day that literally tell us how people are using Cluely, and we have, like, hundreds of customer emails saying like, "Hey, this is what I hate about Cluely," and like, like, okay, okay, now I know what we need to fix.
- AGAakash Gupta
Roy Lee is one of the smartest and richest 21-year-olds you'll meet. With his company Cluely raising $15 million Series A last week, at typical dilution levels, he would be worth eight figures. What does Cluely make? AI that helps you cheat on interviews and tests, AI that can't be detected but can listen to your computer audio and read your screen. What do I need to know about your early years to understand the Roy that's sitting in front of me today?
- RLRoy Lee
I think the single most defining character feature of me from the second I gained consciousness was, um, provocative.
- AGAakash Gupta
So you've been kicked out of not one, but kinda two schools, with Columbia as well.
- RLRoy Lee
Yeah, yeah, yeah. After that one time, like, you get kicked out of school once, and it sort of, like, really toughens your mind and really makes you rethink, like, do I even need school in the first place?
- AGAakash Gupta
Talk about being at the top of the timeline. You guys are the main characters in the X For You page right now. How does that feel?
- RLRoy Lee
It feels like I have all these assumptions about virality, and I've spent months wondering, like, man, I wonder why X feels so different from Instagram, TikTok.
- AGAakash Gupta
One of the most interesting things I saw recently on Twitter was people claimed your system prompt was leaked. I have that up on the screen right now. Is this what was actually your system prompt? [beep] Really quickly, I think a crazy stat is that more than 50% of you listening are not subscribed. If you can subscribe on YouTube, follow on Apple or Spotify Podcasts, my commitment to you is that we'll continue to make this content better and better. And now on to today's episode. Welcome to the podcast.
- RLRoy Lee
Thanks for having me, brother.
- AGAakash Gupta
What do I need to know about your early years to understand the Roy that's sitting in front of me today?
- RLRoy Lee
I think the single most defining character feature of me from, like, literally the second I gained consciousness was, um, provocative. Uh, like, literally since elementary school, kindergarten, there's been a camp of people who have been, like, avid Roy supporters and a camp of people who have been Roy haters. Every single time I've had a thought that's entered my mind, I've said it out loud publicly and, like, very brazenly, and this has, like, burned me and helped me many times. This has, uh, gotten me, you know, like, like, in school, leadership positions at clubs, and a bunch of people who love me, like a solid friend group, and it's also gotten me, you know, like, like, suspensions from school. I spent, like, every other Sat- every other Saturday in Saturday school and, like, a bunch of... a million detentions, and it e- even even- eventually got me, like, kicked out of Harvard. So, um, there, there, there's been a lot of, like, like, burns and a lot of gains from me being the polarizing person that I am.
- AGAakash Gupta
You were kicked out of Harvard?
- RLRoy Lee
Yeah, yeah. Senior year of high school, I, um, got into Harvard early as probably a result of me doing all this crazy shit, um, and later that... Like, like, I had a suspension for sneaking out of a field trip, um, and later that year, there was a camp of Roy, Roy haters who did not like a- all the brazen, crazy shit that I did. Um, they, they, they mass reported me, and, and it ended up getting me suspended, uh, rescinded from Harvard.
- AGAakash Gupta
Wow. So you've been kicked out of not one, but kinda two schools, with Columbia-
- RLRoy Lee
Yeah
- AGAakash Gupta
... as well.
- RLRoy Lee
Yeah, yeah, yeah. I mean, after that, after that one time, like, you get kicked out of school once, and it sort of, like, really toughens your mind and really makes you rethink, like, do I even need school in the first place? And after that first time I got rescinded, like, my mind was locked onto, okay, I've always been unconventional, and I've always been successful at things that I've done. I need to channel this into, like, the biggest, boldest play ever, and that's, like, building a company, bro.
- AGAakash Gupta
Building a company indeed. And last time you shared the stats, it was at 5 million ARR. What's the latest for Cluely's growth?
- RLRoy Lee
Yeah, yeah, yeah. We're, we're, we're almost at six, so we're, we're, we're going... we're growing quite quickly, and I think, um, one thing that people don't, don't realize and often forget is, uh, like, we wrote the first line of code for Cluely, like, 10 weeks ago. Um, we are earlier stage than, like, most YC companies of the latest batch. Uh, but it's, it's hard to remember that because it feels like we've been on top of the timeline forever. But, um, it's just a function of a really world-class amazing marketing team.
- AGAakash Gupta
Talk about being at the top of the timeline. You guys are the main characters in the X For You page right now. How does that feel?
- RLRoy Lee
It's pretty crazy, and it's really, really, I'd say, like, vindicating. Not... No, I, I, I, I, I, I think crazy is the most general and, and, and specific that, that this feeling can get. But it feels like I have all these assumptions about virality, and I've spent months wondering, like, man, I wonder why X feels so different from Instagram, TikTok. It feels like on Instagram, TikTok, there's creators who have cracked the algorithm. I wonder why the Tech Twitter feed looks so different. Like, why don't people apply these concepts on Twitter and just go hyperviral like they should? Um, and I've had all these assumptions, and as soon as I started implementing them, like, they started working immediately and to, like, a massive scale. Like, I've literally become the main character of Tech Twitter in the span of a few weeks, like a few weeks of pressing the button that I feel like is so obvious and clear to everyone. Um, and it feels crazy that nobody else has caught on. It feels like I genuinely am pioneering something.
- AGAakash Gupta
What have the millennials like me, what are we not understanding about your approach to virality?
- RLRoy Lee
I think what people don't understand is that short-form, like, these algorithms reward what is most controversial. And people on X, LinkedIn, like, these are nerdy tech bros who want to appear smart or like, like, like, thought-provoking, and they'll write these long essays that maybe, like, 200 people in the world can understand in, like, an attempt to appear smart. But in reality, the algorithm rewards things that are digestible, controversial, and force people to have an opinion about. And for some reason, people on X, LinkedIn just have not caught on about, like, what are the best ways I can, I can grow my company and, like, like, bring visibility to my company in doing this. And it's, it's just like, like, obviously, like, the nerdy tech bros that grow up and start tech companies are just not the same people that will be scrolling on Instagram, Instagram, TikTok and just be-Caught up on the latest in cultural trends, but, um, I think I am part of a new generation of founder that, that has. Like, I've grown up on, on, on this shit.
- AGAakash Gupta
Yeah, we grew up on Facebook and stuff, and I think it was always about, like, presenting your best self. Even on LinkedIn, it's, like, about presenting this curated version of yourself. But you're willing to present kind of a more controversial side. How do you correctly create content that's controversial but still drives to your product? Today's episode is brought to you by the AI PM Certification on Maven. Run by Miqdad Jaffer, who is a product leader at OpenAI, this is not your typical course. It's eight weeks of live cohort-based learning with a leader at one of the top companies in tech. OpenAI just doesn't stop shipping, and this is your chance to learn how. Run along with product faculty and Mo Ali, the course has a 4.9 rating with 133 reviews. Former students come from companies like OpenAI, Shopify, Stripe, Google, and Meta. The best part? Your company can probably cover the cost. So if you want to get $500 off, use my code AAKASH25 and head to maven.com/product-faculty. That's M-A-V-E-N.com/P-R-O-D-U-C-T-F-A-C-U-L-T-Y. Today's episode is brought to you by Jira Product Discovery. If you're like most product managers, you're probably in Jira tracking tickets and managing the backlog. But what about everything that happens before delivery? Jira Product Discovery helps you move your discovery, prioritization, and even roadmapping work out of spreadsheets and into a purpose-built tool designed for product teams. Capture insights, prioritize what matters, and create roadmaps you can easily tailor for any audience. And because it's built to work with Jira, everything stays connected from idea to delivery. Used by product teams at Canva, Deliveroo, and even The Economist, check out why and try it for free today at atlassian.com/product-discovery. That's A-T-L-A-S-S-I-A-N.com/product-discovery. Jira Product Discovery, build the right thing.
- RLRoy Lee
I think this is something that less people have to worry about. Like, there's way too many people that worry about a highly converting marketing funnel and all this bullshit, but in reality, there's no one else out there with more brand visibility than me, and there's probably not a company out there that would not die for, to have this sort of visibility on their product, especially at this early stage of being, like, two and a half months, um, in. And, um, I think it's really hard to put a monetary value on this because how exactly can you track all the conversions from literally being the, the main character of Tech Twitter? Like, it's impossible. More than that, the, the formats that will be viral, these change, like, literally overnight. Overnight, you need to know the new thing that will be viral, and you have no i- And if, if your content is changing literally every week, then how are you supposed to... Like, if you find a winning content format, it's not really like you can rinse and repeat it, 'cause in a month that's expired and it's not viral anymore. You just have to keep iterating and trying new things, and I think it's pointless to track conversions on bull- and then, like, bullshit like that because, uh, if you just know, "Hey, my product is visible here. If I was a consumer and I saw this pro- and I saw this video, I would actually be incentivized. There's an actual call to action here," then the video will be converting and you don't have to worry about it. Because even if you discover, oh, it's converting and it's like, like, roughly like a $2.73 second, like, like, like, like, it, it's, it's all, it's all noise, bro. Like, like, in a month, the numbers mean nothing and they're expired.
- AGAakash Gupta
The growth marketer in me died inside a little bit hearing that.
- RLRoy Lee
Perhaps, yeah. I mean, like, like, may- maybe I'm wrong, but it's really, you cannot put a dollar value on the, the visibility that we have right now.
- AGAakash Gupta
It's crazy. I would say you guys are easily the best distributing startup at the Series A or B range. If you were to break down the strategy for your friend who wanted to kinda copy your playbook, what would be the key elements?
- RLRoy Lee
A lot of people don't know, but we're averaging, like, in, in our first month of UGC on Instagram, we've done, like, we're probably on track to do, like, 50 million views a month. Um, it's not just X LinkedIn that we're viral in. We're, like, pretty much viral everywhere. And, uh, there's things... Like, the, the one thing that you need to understand, I think, is that since five years ago, uh, short-form content has surpassed long-form content in views and, and, and, and, and, and usage.
Episode duration: 45:23
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