Transcription
I was kind of a little, I'm so sorry. My past managers, I'm so sorry.
"You're all right."
"What were the biggest lessons you've learned as a manager?"
"I think letting go, giving them enough guidance, letting them bump their way and like make them little mistakes. The first instinct is to just do the work."
"Let me do it."
"Yeah. Give me the wheel."
"[laughter] and I'll drive. That's like short-term easy and long-term really hard."
"Kevin says my toxic trait is whenever I say..."
"It's not even that hard."
"[laughter] Holy This is the reason people hate PMs."
"[laughter] How hard can it be to change this one line of code?"
"Yeah, how hard could it be? I've always had a question for you. Why did you lay me off?"
"Office Drama. Welcome to Office Drama, where we sit with people obsessed with their work and talk about the inner drama behind their career breakthroughs. I'm your host Chloe Shi, and today in the office, we have one of the most perfect, beloved product leaders in all of Silicon Valley. He is the principal product manager at Roblox. He worked at YouTube, Twitch, Yik Yak, and Facebook, and he was my manager at Discord. Derek Yang, everyone."
"[cheering] Hello. That was a big sell. Thank you."
"Derek, you know you're a very special person in my life because you were the very last manager I've ever had in corporate."
"Wow."
"It's been exactly 2 years, but I feel like we accomplished a lot together. I think of those days fondly at Discord. We were talking about creator revenue, we shipped a lot of stuff. Shout out to creator revenue at Discord, which was helping Discord server admins make money."
"Yeah, well I still remember..."
"Make money. You're a phenomenal manager. I trusted you with my career and my life, and I've always had a question for you. Why did you lay me off?"
"[laughter] Wasn't my choice, but you know, it's it's a..."
"Look at the Look at the camera and tell them."
"Yeah, I I think it the First of all, being your last manager ever means that I was probably not as good as you were making me out to be."
"[laughter] but..."
"You're amazing. People loved you."
"Yeah, but look like I think at the end of the day like you are doing something that hopefully you love even more than product management right now, right?"
"Product a lot. Yeah."
"Yeah, I mean, look, I think you were a great product manager, but like you're an even better content creator, so hopefully that's a good thing for you."
"Good product manager?"
"Your words, not mine."
"[laughter] I can't believe it's like the 2-year anniversary of when all that went down. That was a really traumatic time. What was that like for you guys? You had no idea, right, as a product..."
"Idea until that morning. It was a big surprise. I had I guess little little birdies tell me at the very very last minute, and I immediately was like, 'The hell's going on?' you know, and I didn't get much info, but I knew that it was coming."
"I felt it, too. I felt it. I felt the energy. I feel like I didn't try hard enough to be in the inner circles, and I wasn't visible enough cuz I was in LA, I was remote. I really stuck with my team. I didn't really do anything with any other team."
"Mhm."
"Um do you think if I tried harder as visibility, that would have changed anything?"
"I think it would have helped. I mean, if the people making all the calls know you and value you, they're maybe less likely to put you on a cut list. I don't think you were, you know, invisible because you were remote or anything like that, but I think yeah, the office presence given how, you know, the execs were very concentrated in office, maybe it would have helped."
"I remember 1 to 2 months after 2024 March."
"Yeah."
"we hopped on a video call, and I was like, 'Derek, what do I do with my life? Should I go back to tech?' And you were like, 'No.'"
"[laughter] I remember that."
"You were like, 'The The economy's bad right now, Chloe. It's tough out here. I think you should do content.' And I was like, 'Are you sure? I don't know. I'm scared.'"
"I was like, 'You got to put all your chips in content. You're doing so well. There's momentum. Like, why give that up?'"
"I mean, it was just scary. Like, I was so torn. I was like, 'Go back to tech, do content, make start a company.'"
"I know. Looking back now, do you do you feel like you regret anything about the way you chose?"
"I don't think so. No, thank you for pushing me."
"Yeah."
"Yeah, kicking me out of tech is what got her did."
"I feel like in a lot of ways like your personal definition of like success, your goals changed over time. All of us..."
"Yeah."
"...have that same experience and that's perfectly okay."
"Yeah, thank you. Thank you for believing in me. I was very scared."
"Of course."
"I'm a scaredy-cat."
"Chloe fan club."
"You're an ENTJ Taurus that chose product management. You worked at elite companies and made it to principal PM, making bank, hopefully. You're a new father. You have a beautiful home in San Francisco. You're a morning person. You work out. So, tell me, are your parents still disappointed that you're not a doctor yet?"
"Yeah, I mean, I have Asian parents. Of course they are. Um I don't know about about being a doctor, but I feel like both my parents are highly highly educated, very, you know, successful in their own careers."
"So, do they know what you do?"
"I don't really think they understand what product management is fully. I think they have a rough idea of like the day-to-day types of things that I do, but if you were to ask them, I think they would give a uh not a great answer."
"[laughter] Do they know what Roblox is?"
"Yeah, I think so. Yeah."
"I I don't think I even know what Roblox is, to be honest. I've seen it, but like, I don't know."
"Okay, let me try it. Let me try this."
"Let's go. Let's go. Let's go."
"Roblox, everything you know about YouTube for videos, think about Roblox is that but for games. This place, this platform where you have tools that allow people to like make games, distribute games. There's players that can find and play games, and there's tools that can be used to like monetize those games for the developers, what we call creators on the platform."
"And what do you do there?"
"So, I'm a product manager on the user team, and I look after all of our content sharing products. So, we just launched Moments last year, and what it does is let players and creators capture the gameplay on the platform, and then share it out, publish it directly on the platform."
"Wait, isn't that basically clips that you did at Twitch?"
"I may or may not have pushed really hard for clips as the name, but with shutdowns and..."
"No. You've had a really, really successful career. Do you When When did you feel like you really made it?"
"I'll let you know when it comes."
"[laughter] [gasps] What are you talking about?"
"I don't think I've really made it, to be honest. I feel like I'm doing well um by maybe external measures, but I feel like there's a a lot more to go."
"Mm. Okay. What's making it? What Why didn't you make it yet?"
"Know. Actually, I I've never really sat down in the in the past like 5 or 10 years to like re-evaluate what does made it mean to me. I just know that there are a lot of changes happening in the world, and there's always going to be more stuff that I can do that brings value to the world, right? Like this sounds a little corny, but I think that's that's just really what I believe in. So, I don't know. I I don't know that I would say I've made it, but I think I'm doing okay."
"So, only child syndrome?"
"Yeah, something like that. Maybe. I feel like..."
"If your job didn't exist today, what would you do instead?"
"When I was little, I actually really wanted to pursue a career in acting. I know."
"Is that the UCLA in you?"
"Super random. No, I I think that dream died when I was growing up. When I moved to the US, I was like 10 years old."
"Uh-huh."
"And immediately, it was brand new world, culture, language that I didn't speak, and so um that actor aspiration really just like fell to, you know, the abyss. I had to do things for survival first and then try to figure out what I wanted to be. First of all, meaning I didn't really speak the language and kids are kind of jerks, little when you don't speak their language. So, a lot of my effort was really just piled into like how do I assimilate, how do I fit in, how do I speak and communicate effectively so I can make friends."
"Are you okay?"
"I know."
"Are you like healed yet?"
"[laughter] Somewhat."
"I wasn't actually a good student for my first two years in high school."
"You?"
"I was a bad student, yeah."
"Like you were dumb or you were just didn't care?"
"I took like the wrong branch in the road at some point and I I don't think I was a very good high school student. I didn't focus on my studies very much and it was only until only in junior year when I started focusing on like here's what I should be doing to set myself up for a, you know, college, career, and and stuff like that."
"It's hard at that time. Your favorite anime is Hajime no Ippo. It's a boxing anime and it was your biggest inspiration for you to get fit to lose the muffin top."
"Yeah."
"Yeah, muffin top is..."
"Do you remember coach Kamogawa?"
"Yes."
"He says, 'Run until you can't run anymore, then run again. Constant effort is life's greatest shortcut.'"
"Yeah."
"Is that your life philosophy or is that your personality disorder?"
"[laughter] Little of both, actually. I feel like that philosophy takes you to a certain point, but it's also something you have to kind of like let go and unlearn. I really like that. I don't know if you like found that on my Facebook or something, but..."
"I did not."
"[laughter] There are more. Not everyone who works hard is rewarded, but all those who seek succeed have worked hard."
"I like that. And see, this is why..."
"That's your boy."
"Yeah, Ippo is my favorite."
"That's your boy."
"Yes."
"Is this your reason for your ambition, why you're you always want more and want to be the best? Cuz you You so hard, Derek."
"Yeah."
"You have no chill."
"I I Yeah, I think that's what a lot of people perceive me as."
"[laughter] Um maybe not super wrong, but I feel like, you know how some people are just born super confident and like self-assured in everything they do. I'm not really like that. I think I really build my inner confidence by putting in the hard work and the reps. So, I know like deep down I've done the legwork. I've done all the necessary sort of foundation work to be confident."
"Mhm."
"Um so yeah, I think like Ippo really represents that and that anime got me to, like you said, like lose lose weight. I started like running a lot and doing weightlifting and stuff like that when I was in high school. And yeah, I went from like a little chubster to uh you know, some someone more fit."
"What is your mastery? What are you like better than everyone else at?"
"Just being relentlessly curious and persistent in what I do. I feel like that is a superpower."
"That is."
"And I think that's not really something you're necessarily born with. Like you can learn that skill, right? Like I think everything about curiosity and like genuine interest in something is something that you can develop. It's not something that you're just naturally born with."
"Serious question. What adversity do you face as the owner of the @dereck handle on Instagram? And please don't minimize your experience."
"Yeah, I get My inbox is full all the time. And it's..."
"Popular than I am."
"No, no, no. Maybe something."
"[laughter] But no, I get people asking me like, 'Hey, bro. Can I have your handle?' Yeah. The number of randoms who who message me about that. And I've been offered, do you care to take a guess? Like the maximum amount of money that I've been offered."
"A thousand? Five thousand? Oh! [gasps] Ten thousand?"
"No. Fifty thousand dollars."
"What?"
"Yeah."
"And you said that you're not selling."
"No. Well, one is like I don't really know if they're truly legit. Although they offered to actually like send me the money in crypto first."
"Okay, crypto is a scary."
"Yeah, I know. I know. Crypto or just like wired funds, too. But yeah, anyway, like I'm not really interested in selling. Like..."
"You don't have a number?"
"Not really. I mean, I'm sure there's a number if you I mean if If people offer a very..."
"Like 500,000?"
"I would consider it, but it's also against platform policy."
"It is?"
"Yeah, it is. So, I feel like part of it is just like people are trying to trick me to say that I'm selling it and then get me banned and then they can claim it."
"Yo, you're so smart. I would have fallen to that trap. Well, there's a responsibility of representing all Derek globally. Keep you up at night."
"You know what? My account has actually been taken down before for impersonating Derek Jeter, the retired baseball player. Yankee. And obviously I don't do that, right? Like no, but it's people just like doing everything that I that they can to take that name down so that they can claim it for themselves."
"That's a really tiring life you live."
"I'm not as active on Instagram these days, but when I was, I was super annoyed."
"I feel like every Derek in the world has looked you up."
"Very possible."
"Yeah, and they're like, 'Oh, I wonder if Derek's taken.'"
"Yeah."
"That's rough. You are now a new father. Congratulations. If the technology was possible for men to get pregnant, would you have chosen to birth your baby and yes, your wife will watch this."
"[laughter and gasps] Um I think that would have been a pretty serious discussion. My wife and I would..."
"Let's have it. Let's have it. The discussion."
"I feel like that experience is probably one of the most traumatizing things in life. And I'm I'm like speaking this from like second-hand experience taking care of my wife through the process. And I wouldn't want to do it, but if the option were there to take some of the pain off of her plate, I would consider it."
"Wouldn't do the whole thing, but like if you could like Bluetooth connect and then be like, 'I'll take some I'll take some.'"
"Yeah, you know how like in some animes, you can like share the pain and stuff like that? Yeah, I would be willing to do that."
"Do you know what this is?"
"It's a truck."
"Specifically, what do we call it? You know this."
"I don't."
"Are you a weeb or not?"
"I I guess I'm losing weeb points here."
"This is the isekai truck."
"Oh."
"Hit by a truck."
"I see."
"Okay, so let's say you get off of work late because I don't know, you get chewed out, your manager chews you out, shareholders chew you out. You're at a convenience store."
"Tuesday."
"Yeah. Grabbing a juice, you walk out, smell the cold competitive air of San Francisco, and you're like, 'Ah, my stock options.' Or your stocks. You're going to cross the street, and you see truck-kun. Do you step in front of it and go into another world?"
"No."
"Okay, so I didn't prepare for a no answer."
"Okay, let's..."
"[laughter] All right, I choose no, but someone behind pushes me."
"Yeah, someone from the higher pushes you, then truck-kun swerves into you and hits you. Would you rather be reincarnated into Demon Slayer, but you're a civilian,"
"Okay."
"Jujutsu Kaisen, but you're a civilian, Attack on Titan, but you're a civilian,"
"Hell no."
"or Apothecary Diaries, but you're a unique?"
"Definitely not Attack on Titan."
"No stressed out civilian."
"Yeah, yeah, those those that just food. You're just being reincarnated as food."
"[laughter] Demon Slayer is actually kind of interesting, but as a as a civilian, like you can't become..."
"You're just You're just there for the main character's aura farm. Like you're on the side, and like you get hit and stuff."
"[laughter] I'll probably choose Demon Slayer, and I think I think that world also has non demon slayer sort of characters that are really interesting that I can maybe Yeah, exactly. Yeah, exactly. The The blacksmiths and the stuff like that. Yeah, yeah, I think Yeah. I think that those could be interesting. And if I got bored, I could always I guess get turned into a demon."
"What is your morning mantra to get up?"
"Interesting. This is such a boring answer, but I don't think I've ever had a morning mantra. I just know what I got to do and I go do it."
"You look at the mirror. You know what you got to do and you go do it."
"Yeah, I I feel like instead of looking at myself in the mirror and giving myself like a pep talk and stuff like that, it's actually just like looking over again what the plan is [laughter] and then saying like, 'Is there anything I'm missing?' If not, let's go."
"You're an ENTJ and us, we are both ENTJs."
"Yeah."
"Uh what's your bedtime mantra?"
"Hold on. Before before we get there, what's your pep talk? What's your like mirror mirror routine?"
"I don't have a pep talk, but I'm just like, 'Oh, you're so cute.'"
"[laughter] Oh, like you're cute today. And [clears throat] then sometimes I sometimes Kevin will walk in and I'll be like, 'Careful. Kevin, careful.' And he's like, 'What? I'm cute today.'"
"Oh my god. This sounds very you. You know how some people have like this whole stand in front of the mirror, do the Superman pose, puff up your chest, and you know, give yourself the the confidence thing. I don't think I've ever really done it. Like I've tried it and it just feels really silly and awkward to me. So, yeah, I don't think I've really worked that into any routines. Oh my gosh, I'm getting..."
"Can you just hold this?"
"Sure."
"Can you just start curling? And I'm just going to ask you a question."
"Okay."
"So, in 2023, Discord hosted a company-wide hackathon and Derek submitted his hackathon project while curling a dumbbell on the screen. What was the product decision behind this tactic or were you just aura farming?"
"I I kind of aura farming, but I thought it'd be really funny to just bring in some random elements. Like when I see YouTube videos where they're just in the middle of some really serious conversation and there's a cut and something random starts happening being introduced into it. It I just find that hilarious. So, there we go."
"That's what the prop was for."
"Hey, first place in Hack Week, all right?"
"You were first place?"
"Yeah."
"I forgot. I was laughing my ass off from my screen cuz I'm remote. I was looking at it on my Discord video and I was like, 'Yeah, I believe Derek is doing this. This is so insane.'"
"Yeah, thank you for bringing the five-pounders to to it. Makes it look like effortless. I appreciate that."
"Uh that's just what we could carry. You have an impressive collection of figurines, collectibles, and anime merch in your home office. How much money have you spent on it all?"
"Oh my god."
"And did you get written approval from the wife?"
"No. I did not."
"Jail."
"Yeah, I know. It was bad. I think that's something that I really picked up during the pandemic and I thought it just..."
"Would end?"
"Yeah, but it didn't. I stopped buying them after the baby was born, but yeah, I think in total I've spent probably north of 2,000."
"I was going to guess 10K."
"No, no, not quite. Um..."
"But I think your Genshin Impact stuff counts."
"Ooh, if we add that, north of 5,000? Yeah."
"You have more in Genshin than in physical things."
"Yeah, it's a it's a gacha game. I've spent a lot of money on character pulls."
"You're the most emotionally stable, empathetic, and not annoying product leader I know, which is statistically unlikely. What are you actually hiding?"
"Wait, not annoying? That's a thing? That's a low bar."
"Product leaders are Product managers are so annoying."
"Yeah, I think that's the perception that people have about product managers on on like Blind, too."
"Yeah, everyone hates PMs."
"PMs get a lot of hate. I feel like they get a bad rap. I'm sure some people I've worked with really dislike me, too, for whatever reason. And I feel like there's uh there's there's a bit of it that is like, 'Okay, this this person is super anal about the details and hypercritical about things that we do.' I feel like I'm sort of misunderstood on that, but..."
"Misunderstood?"
"I feel like a lot of the things that I really care about is is literally just I'm curious. I'm trying to like find the truth, right? Instead of being critical. And I'm like passionate and interested about the thing. That's why I like lean in and ask a lot of questions."
"And they perceive that as a tax."
"I feel like they do sometimes, and they immediately have this sense of defensiveness. I think that's natural, too."
"And then [clears throat] how do you like calm them down?"
"Okay, like they're thinking we're doing something wrong or or bad, right? But that's not really my intention at all. How do I calm them down?"
"Yeah, I'd be like, 'I'm going to ask you a question. Don't take It's not It doesn't mean anything.'"
"Yeah, I think prefacing with the context is really helpful. There's like interesting framing that you can do to just like annotate before you you make a suggestion or ask a question that can set the mood differently. And yeah, we just thought it's actually perfect."
"Time for our next segment. It's called personal shields. This is an activity I did in my leadership nonprofit many years ago, and I super love it, and I get to know people on a deeper level. The assignment is simple. All you got to do is think of your top two to three skills, role models, values, and turning points, and where you see yourself in 5 years, and you just draw it on a shield. No words. Just drawings."
"Okay, you want me to just go from the top left?"
"Mhm."
"Okay. Role models. I feel like I have different role models through different eras of my life, I suppose. Um the first part is when I was little. And so, that's me. And this is my my dad."
"Aw, papa."
"Yeah, so my dad was my first role model. I think that's pretty common for kids. This big human who seemed to know it all and have everything under control, very stable, mature, wise, and can like do everything I want to do but better."
"[laughter] And I think as I um aged into I don't know, teenage years and and honestly even like into my 20s, I found a lot of my role models in anime that I watched, right? So, we talked about Hajime no Ippo and that's what this boxing glove represents. Yeah, so it was like a bunch of like hard work, grit, perseverance, and really like using all of that to formulate your like inner confidence and stuff. Um this is a very poorly drawn. Do you know what this is?"
"Haikyuu volleyball?"
"Yeah, oh my god, you called it a volleyball. But yeah, Haikyuu is another one of those coming-of-age stories where you are on a journey to get better, you go through ups and downs, and you basically have to overcome a lot of your own shortcomings and be humbled in a lot of ways to get to where you want to be. Okay, and then values, I have three drawings. The first is curiosity. So, it's this guy seeing an apple drop from the tree, it's Newton asking why, yes. Um so, the second one is persistence. So, it's a turtle on a racetrack to a very distant goal. Um and the third one is optimism."
"Oh, the half empty half full."
"Yeah. Oh, you're an optimistic guy."
"Yeah, I think you got to be. And if you're not,"
"[gasps] life is pretty bleak."
"[laughter] Yeah."
"I feel a lot of people are not."
"Yeah. I feel like you have to believe that the effort you're putting in and what you're doing is going to get you to a better place. So."
"Bare, delusional. The lulu is the salulu."
"That's a great That's a great quote. And then in terms of turning points, I have two. Um the first one is brunch with friends."
"Huh?"
"I I I know. I know. So,..."
"Like every Sunday?"
"Yeah. Yeah, every Sunday I have a turning point. I just had a turning point. No. No, this was like a specific brunch in 2013 where I was living in LA. I was in my second job out of college. And this was doing like marketing analytics. I was doing fine, doing well, just got a promotion. Um but I wasn't really feeling fulfilled. And there wasn't a lot of purpose to what I was doing. I visited my friends in San Francisco, and we had a brunch catch-up. All of them worked in tech at that point. And one of them just whips out a laptop with like a Balsamiq design thing."
"Mhm. That's old."
"Very old. He just starts talking about this this concept that he's been thinking about with these really, you know, shitty wireframes. And the other two just like started chiming in, and they were just like jamming, riffing, just had a ton of ideas going. And I was just sitting there like unable to participate cuz that's not really the world that I lived in."
"Mhm."
"But I felt super energized just like listening to them talk about it. And I got super curious on like how do I get into this world where I'm actually part of building out this thing that I'm deeply interested in. Um and that's what got me to start exploring the the world of tech, actually."
"Wow."
"Yeah. The other turning point, less happy, but this is me, and this was uh a previous manager that I had at some point. Let me think about how to talk about this one. So,..."
"He."
"Uh yeah, so it was I actually wanted to make this one like a three-panel comic, but..."
"[laughter] skills were limited."
"High taste, low execution ability."
"Yeah, that's right."
"[laughter] Good thing we've got AI."
"AI can't draw markers on this piece of paper."
"Yet. Not [laughter] yet."
"Um but yeah, so the the context is basically I'd done a lot of really good work if I were to evaluate myself and I'd sacrificed a lot. Like personal time, family time, and all those things. And I think the expectations that I had for myself and and loosely with management was that this would you know, earn whatever to the rating, blah blah blah. But the end result was that I actually got a meets most expectations which in the tech world means that you failed, right? Like you you are not good doing a good job. We we we literally were the only team that hit all of our launch goals and milestones and metrics that we set we agreed on with leadership. And like basically everyone thought that like, okay, cool. This this is like the the product that's like on the up."
"Yeah."
"And on that cycle I got a meets most."
"[sighs and gasps] Yeah. Oh, the feedback given to me was that I wasn't decisive enough and I uh didn't push the pace enough which was really surprising given that we had hit really ambitious timelines and the metrics that we all agreed on. But yeah, made me feel like, okay, like I have to play this game..."
"Better, yeah."
"Yeah, yeah, better and um really changed the way that I was thinking about doing things cuz I had sacrificed a ton."
"Right, yeah."
"And the result was basically the opposite of what I thought I would be getting. That was really hurtful. Like for for the next maybe 2 days after that conversation, I was just like in this hazy like, what am I doing with my life type of thing? I know it's like very over dramatic. Yeah."
"Chosen the truck? [laughter] Would you have chosen the truck."
"Truckcoon sounds pretty good at that time. Yeah, it was it was different and I think it it really changed my outlook a little bit on how much value was put on like the the effort and the grind and I think that's your one of the less lessons that I learned about careers in general is just we all evaluate ourselves based on our efforts and intentions. We get evaluated and we evaluate others based on the outcomes and some perception that is out of your control."
"Cuz you're full of grit. You're a gritty sweaty boy."
"I don't know about sweaty, but..."
"Sweating for the shareholders."
"Yeah, always. Yeah, shareholder [snorts] value. But I have that tattooed on my back actually."
"[laughter] Um, two skills. One is min-maxing because min-maxing actually to me is not just like pure optimization. It's making really difficult trade-off decisions too because you have to min some stuff so that you can max other things. And yeah, I think focusing on the right things and giving up things on giving up on things that you sort of kind of want as a skill."
"What have you been min-maxing lately?"
"I've given up a lot of video game time to be honest."
"Is personal min-maxing not like at the workplace. Like I'm minimizing my one-on-one so I can maximize my strategy heads down time. I don't know."
"It could be that too. Um, at work I feel like min-maxing for me has been I'm I'm no longer trying to please everyone and like satisfy everyone else's needs. I feel like if you're not disappointing someone at the company..."
"Wrong."
"...you're probably disappointing yourself at the end of the day cuz you're you're you're like trying to please everyone else's expectations and you you may be actually giving up a part of your own identity. I feel like that's the the shadow to the whole like adaptability sort of superpower."
"That is your shadow."
"Yeah."
"Yeah."
"Yeah, so I've been trying to dial back on that and like really just be very like self-assured and confident in pushing for the things that I believe are right. It's like the positive spin on main character energy."
"Yeah."
"Yeah. Yeah. Yeah. It's It's less of the like self-centered me me kind of thing, but it's a more like like this thing is the thing that we all need. Second skill, thought bubble thing. It's meant to represent scalable communication."
"Dude, how do you do that?"
"I think it's knowing your audience a little bit and being flexible stylistically, language-wise, with how you present ideas, and how you convey things."
"Wait, what what's scalable? Like I know what communication is. What's scalable communication?"
"So, yeah, I think scalable communication is basically you can effectively talk to anyone. Yeah, with different context levels, different skill sets, different functions. I think written communication is a really good way to have scalable communication. Doesn't matter if it's on Slack, email. I think you just adapt to the medium. I think it involves a lot of practice in real time, which means you can fail a lot in real time, but that's how you get the reps in."
"New grads don't know how to do that at all."
"Yeah."
"Like giving context to the right elevation of detail, asking the right questions, and then knowing where things should go, what the blast radius should be, what even to ask."
"Mhm."
"I I don't know how to teach that."
"Yeah, it's really hard to learn. And what I see from like a lot of the like more junior PMs that I work with is they first tend to give all the context, like all the details, all of their thinking, show all of their work. And it turns out that's way too noisy, and sometimes it just like dilutes what you're actually trying to get across. So, that's part of what I mean by scalable communication is you hone in on the right messages and the key points. Cool. And then the last part is the 5-year vision. Super simple. It's just me, my wife, and my daughter. Everyone is smiling. She is bigger than she is now."
"What was last year's theme about? What was like the greatest learning of last year? Cuz last year it was a big year for you."
"Last year was pretty humbling for me. It was when I became a parent. It was also the year where we worked on our product from like zero to one. And as the product lead on that, being gone for an extended period of time is pretty rough. I I have limits to to what I can do and what I can accomplish, especially when there's like a little human that depends on me to keep surviving. Yeah, it was like a year that really made me give up on a lot of things that I I've wanted for myself and I really enjoyed. So, video games one of those examples. Um Brazilian Jiu-Jitsu, I had to like hit pause on that. I've always admired like the colleagues I had who seem to be able to balance somehow their career growth, super ambitious, um but also being like really there for their families. Now that I have one kid who is like angel baby on on a relative scale. Yeah, um it's still a lot of it's a lot of work, right? You you take away a lot of your time, you can no longer do whatever you want anytime you want. Yeah, it makes me it makes me really admire those people even more cuz some of them have like three, four kids and they still manage to like do it all."
"What kind of leader do you want to be at work? How are the youths?"
"[laughter and gasps] The youth. A lot of overcoming imposter syndrome, I think is a big part of it."
"Oh, how do you What do you say? Cuz I just raged my way through my 20s."
"Dude, I think that might be the way to go."
"Yeah, I was just so angry. Like I think I felt imposter syndrome and I just got so mad and then I was over it."
"Yeah, yeah, yeah."
"And so whenever people ask me I'm just like, 'I don't know. I don't know. I'm just so angry. Like I hate everything. I'm just like everyone sucks.'"
"Yeah. I feel like the the maybe a place of insecurity comes from like oh do I do I really deserve to be here and there's all these amazing people around like what right do I have to voice my opinion and stuff like that and I think you just got to get over it at some point and that's that's maybe a little insensitive but the truth is like you went through this pretty rigorous interview process or recruiting process. You're here because you should be and that's like that's like the beginning of of the contacts right? And then afterwards I don't think anyone in a workplace really cares about your title as long as you can bring the right level of like conversation..."
"Value, yeah."
"...thought value and..."
"Maybe the fear comes from slipping up in in live and they are afraid of seeming dumber."
"Mhm."
"Yeah, I feel like that's how it plays out. It's like oh I should know this because I'm in this role and position. And if I ask a dumb question then they're going to like make fun of me and judge me inside their heads. But you kind of have to embrace the dumb questions and ask in like a non-dumb way."
"[laughter] Also ask like well whatever."
"That might be a skill in itself but..."
"Yeah."
"Dude I ask a ton of dumb questions throughout the years and dumb questions are great I feel like the times where I've asked questions that I later was like this is super embarrassing how could I have asked that? Those are all like fleeting feelings. They just go away. Like I've gotten embarrassed by the questions I've asked before but yeah I feel like that's how you learn."
"When did you first be become a manager?"
"I hadn't managed some in tech the first place that I became a manager was at Discord."
"Mhm. And then you were just a manager elsewhere as well."
"Yeah but in a completely different role."
"What what were the biggest lessons you've learned as a manager cuz it's such a different role to step into."
"Yeah."
"And you actually care. Do you you actually care about your reports?"
"Yeah."
"And I realize I guess I I don't."
"Yeah."
"[laughter] And I'm like, 'Yo, that's a very selfless thing to do.'"
"Yeah."
"I realized um I was kind of a little in my career and I'm like,"
"[laughter] 'I'm so sorry my past managers. I'm so sorry. I worked hard, but I was also annoying in my own ways.'"
"You're all right. I mean, I feel like you're pretty opinionated, you had your own taste, your sense of like what should be, you know, done in a certain way. And that's actually kind of awesome versus someone who..."
"Doesn't."
"...has no opinion, right? And is looking to other people for guidance on basically every single thing. You had just like, you know, your own sense of taste and that was helpful. I think letting go of something that you had been doing hands-on before and trusting this other person to do it, giving them enough guidance and bumper lanes, training wheels that they don't, you know, fall off the sides, but letting them sort of like bump their way and like make little mistakes through throughout their own process and learning. I think that's one of the things that you have to show a lot of restraint in because the first instinct that I think a lot of new managers transitioning from ICs is to just do the work for..."
"Let me do it."
"Yeah. It It's like Give me the thing, right? Give me the wheel [laughter] and I'll drive. And I feel like that's that's like short-term easy and long-term really hard cuz then your reports never really grow, they don't really learn, they don't really develop the skills to do it on their own. And they may actually develop this habit of like relying on you. Over-relying on you."
"Crutch."
"Yeah. Yeah."
"Yeah, they become their crutch."
"Yeah. W- One of the things I found really helpful was like, if they ask me for the answer, I'll just ask them back. Like, 'What do you think?' Yeah. I I think I did that with you a few times and I think you always actually had an answer you already came to. It might not be the same one that I came to, but um I feel like in the end you need to make decisions, have results, and take accountability for those results so that you can learn."
"How do you define success in your life now? In your personal life, in your professional life."
"Yeah, I think this is why I I have the themes of sustainability and intention in in my current era. I want to be able to do what I do for the next, I don't know, 10 plus years, right? And so, I'm not going to get there if I let myself burn out and try to do everything."
"Everything."
"Were you burnt out in the last couple years?"
"I think I was um feeling effects of burning out from time to time, but typically I can like recharge and get back into it."
"What's on your 2026 vision board? One professional, one personal, one creative."
"I I think this is really around fitness, actually. Um Yeah. Yeah, exactly. Bring that 5-lb back. I feel like right now it's less about performance of how much weight I can lift and more about how sustainable and how..."
"Healthy..."
"...the lifestyle is making me. So, introducing more, you know, lightweight days, mobility, flexibility, like cardio back into what I do. Um I do feel like that seeps into my professional and like, you know, brain power type of stuff, too. I can just last longer in terms of like a heavy work day when I when I feel like I'm active and I'm fit. That's personal. I guess the other part of personal that I I I need to mention is just be a good father. Um [laughter]..."
"Felt obligated to say it."
"...I mean, I feel obligated to to be that cuz she needs me. And I want to be here for her, and she's super adorable. She's like very chubby baby, and I don't think she's going to be in that phase for super long, so I want to cherish that. Okay, professional. I'm not really interested in in like going for promotions right now, and that's nice. If if that's like a side effect of what comes to be, that's great. But for me, it's actually in the current position that I have with the platform that I have, um we can actually build really cool..."
"I can't say that."
"What if your audience was like 12 years old?"
"Um [laughter]..."
"But..."
"Your audience is 12 years old."
"Oh god. Yeah. Um [laughter] But I think it's building cool stuff that I feel is actually valuable for both creators and users on the platform, but also for the company pretty itself. Can't share too much about what it is that we're doing, but it's basically how do we iterate on Moments, the product that we launched this year so that it becomes much more scalable and impacts a lot more people in how they discover and play games on Roblox."
"Exciting. Creative goal."
"I haven't played around with AI tools as much as ideally. And so I wanted to carve out some time that I can use to create some agents that just like automate and simplify, maybe like improve the way I live life."
"What's your creative goal? You have a lot going on."
"Oh, I have a lot."
"Yeah."
"One of the biggest goals, and I don't think I told you, is that I'm starting a production company."
"Wow, big moves."
"I incorporated a couple weeks ago, and then I made my first hire, and he accepted and he's joining next month."
"Oh my god."
"Exciting."
"To be a real manager now with like a full-time employee. So we talked to you like 401k, health care, dental, benefits, incentives, levels. Made a leveling rubric. And I was like writing down what is meets and what's like the next level, what's the career path forward."
"Mhm."
"Yeah. I went there's so much and I was It's not like I'm nervous, but I'm just like anxious because I realized that you know, when you're in your 20s, you're like being a manager is the golden dream. Like you want to get to management. But then the more I got closer to it, the more I realized I just would rather be a super icy."
"Yeah."
"Like I I don't I don't care about management. I don't want to deal with your problems."
"Uh-huh."
"Like you you figure that out. Like that's not on me. That's on you, sir."
"Yeah. [snorts]"
"Yeah."
"Your criteria that you look for in the hire?"
"A huge learning last year was I need to make sure they have they want to be the best."
"Mhm."
"Like they have that grit and that tenacity and that drive cuz I can't teach drive and ambition."
"Mhm."
"I realized that. I thought I could. I was like, 'Oh, if you're a really high achiever, you're very competent, you're..."
like your base level skills are really good, but you don't have drive." I kind of took those people in on the contract side. It it worked for like a baseline, but when you want to I realized if you want to be at the top charts and you want to do something new and things that no one has ever done before, you need someone who's like so obsessed that they will go and search and very curious and very driven to like search up how to improve something without me prompting them and asking them.
Mhm.
Like if I always have to ask and give you the assignment, we're always bottlenecked by my assignment and how good I can instruct. But I'm not that good at instructing. I'm just like, "Can you go figure this out? Blah blah blah. I got to go figure this out." Like you have to figure that out.
Also, what I learned was sob stories are not grit stories.
Mhm.
Yeah, and I heard a lot of sob stories and I I my biggest mistakes was interpreting that as, "Oh, this person has like a lot of drive in them."
I feel like everyone can go through sob story, but it's like how do you change yourself? Basically, the thing that you can actually control
Yeah.
to make sure that it doesn't go that way or it goes better the next time.
Have you had people cry in a one-on-one with you?
You.
Hey, when did I cry? I probably did cry. When did I cry?
[laughter]
I cry a lot, but I'm also someone who externalizes my trauma and then I get over it.
Yeah.
And then I'm like Okay, I'm done.
Yeah, actually you were really good at moving on. You're not the only one, but yeah, there were times
How do you like
hold space?
For me, I think it was like this person that I care about is feeling something that is traumatizing them or causing them to feel this way um at the workplace, right? And I'm responsible for how they do at work and their progression. So, it's really like start from a place of empathy, openness, listening. And then you don't have to be a problem solver all the time, right?
That's a big life lesson.
Yeah. Like I think a lot of the time what you needed was actually just dude, we need to vent. Like this is a vent session. This is not a help me as my manager type of thing. This is just like I need to just talk some
[laughter]
Get it out of my system. And then we can move on, right? And that's super healthy. Yeah.
Uh, I think I remember now. I think I got super mad. I remember now.
Yep.
Yeah.
Yep.
[laughter] [gasps]
What a time.
Yeah. I think actually Kevin came like in the in the background of your video camera. Kevin came in was like, "What's going on?" And then and then he like slowly backs out. Loved it.
I remember. I'm a I'm a loud crier. I will be like
But I think that ability is just like really feel that thing, express it, and then move on is super healthy. I I I recently like heard about this framework for how to evaluate or like look at resilience and then overall like how do you how do you like evaluate someone's mental strength? I forget the exact words they mentioned, but there were four dimensions that I thought was like super interesting. The first, how much you can take before you break. Um, and I forget the word for it, but it's like can you endure a lot before you, you know, reach a breaking point and you change your behavior and like you you need to outburst or whatever. And if you have really low tolerance for that, then that's like one dimension where you have pretty weak mental strength. And the second is like when you do hit that breaking point, which everyone does at a at a certain point, how badly is your outburst, right? Like is it is it like you
my outburst
[laughter]
No, yours is fine, but like is it like you are outbursting in a company all hands you're like yelling and swearing at the CEO and like limiting your career? Or is it like you vent in a trusted circle and then that's it? Or like you you you just basically like do a puffy face, right? Like if you have really like dramatic spikes in the way that you express this kind of stuff, that's also really bad. That's like a mental strength thing that you can work on. And then third is like how quickly do you bounce back when you have those mental outburst breaking moments? And this is where I think like you were actually super strong, right? Like you had the outburst or like the expressions, but then you're just like next day, okay, cool. Let's move on. We're good, right? And and I think like that ability to bounce back quickly is another sign of mental strength. And then the last dimension is when you've bounced back, where is your new baseline? Has this thing basically, you know, changed your behavior for the better or for the worse, right? And if you let that thing be a lasting trauma for you that you always sort of reminisce on, then that's that's another sign of like mental weakness.
Any advice for me as a new manager though, knowing me and my personality and my PT?
You have a really high expectation for yourself and other people. And it can come across as whatever I do is never good enough for Chloe, right? Like I don't know if you've ever heard anyone say that to you before.
Kevin says my toxic trait is whenever I say it's not even that hard.
[laughter]
Holy
It's not that hard. Like
This This is the reason people hate PMs.
[laughter]
How hard can it be to change this one line of code?
Yeah, how hard can it be? Like let me just look at it.
[laughter]
I think he's just coming from a place where we have a shared objective and we're tackling this challenge together instead of like me versus you. I'm I'm like giving you, you know, strong constructive feedback. You're not doing your job. I think it's one of the hard lessons I had to learn is you don't just put your head down, do work, and win in the corporate place in a lot of ways. Someone showed me this quote the other day. It was like, "It's much better to be a race horse than a work horse."
Woah, what's the difference?
Yeah, so I feel like the meaning of that is really like you want to be a race horse that people can see as like super high potential, can really [clears throat] push, drive, and get stuff done, and takes responsibility, take risk, and accountability over a lot of things. And they see this like They see this ability of you as like a leader that can really drive results. Um versus a work horse, which is you're dependable, you're responsible, you deliver on what you say you will, but they don't really see that latent potential in you to become like a super high high influence sort of high scope leader.
Yeah.
And in the workplace, and I think in the horse racing world perhaps, too.
[laughter]
Um I I think the thing you see is like people treat their race horses a lot better, and they get rewarded, recognized, pampered in a lot of ways.
And we want to be pampered. We love that.
Yeah, exactly. And so I think if you care about career progression and recognition and that kind of stuff, it is better to be a a race horse and take risks, take space, like I said.
Yeah, be a character.
Mhm.
Not be an NPC.
Yep. Exactly. It's better to be known for something controversial than to not be known at all.
Yeah, I feel like I also got bolder over time and just a little psycho.
Yeah. If you're known as a strongly opinionated person, but you have all the, you know, right I I I guess street cred to be, then that becomes a positive.
Before we wrap, we need to conduct your performance review.
Okay, I'm ready.
Legally, this does not affect your compensation or leveling, but it does affect your aura. Are you ready to get started?
Yeah, let's go.
Would you rather be right or be promoted?
Damn, wait, this is already This is question one? That's so hard.
[laughter]
Uh I'd rather be right.
Ooh, he's not getting promoted this year. Are you ambitious [snorts] or just too scared to stop?
Ooh, wow, this is like surprisingly deep. A little both. Holy Do I have to pick? Yeah, I'm more ambitious.
Out of 100% for a promotion, what percentage is skill and what percentage is visibility?
Depends on how high up you are. If you're a, you know, fairly junior employee, I feel like more of it is on skill, but the higher up you go, I think the more the skill leans towards visibility. Uh for me, I think it's 50/50.
Ooh, right now?
Mhm.
Ooh, would you rather ship something mid or never ship at all?
Uh I would rather ship something mid if I can improve it. Uh if I know that the thing I ship will always stay in that state, I would rather never ship at all.
Meetings before 10:00 a.m., human rights violation or a personal problem?
Personal problem. I'm a morning person, dude.
[gasps]
10:00 a.m.?
You'll never catch me. You'll never catch me at those hours. Are you the main character or you an NPC?
Main character.
If the pay were absolutely the same, what's better, being a super IC or being a people manager?
Super IC.
If your job disappeared tomorrow, would you feel relieved or panicked?
Panicked. Losing a pretty big part of how I identify with myself. And the income kind of helps. I have a baby to feed now.
That's fair. That's all the questions for performance review. You got an exceeds expectation. Good job.
Yay!
Yay! [screaming]
Thank you for being on this is the first ever Office Drama episode. Appreciate for you taking a risk on me. I really love having our conversations. Whenever I'm in like a moment of I need advice and I need someone to like gut check me and shake me and be like, I think you need to do this. I I always want to reach out to you. So, thank you for staying in touch even after the apocalypse.
Of course. Yeah, it's been an honor even after you left the company. I feel like we've been able to stay in touch and it's been such a joy just like kind of watching how you've evolved your career into a full-time content creator.
Where can people find you online?
You can reach me at LinkedIn. That's probably the the most uh consistent place. Uh you can probably DM me on Derek at Instagram.
They would have to compete with all the other DMs.
Yeah, yeah. Make sure you you put a good offer in for using it.
[laughter]
Has to be above 50k.
Yeah. Exactly. Yeah, LinkedIn is probably the best place.
Derek Yeng, LinkedIn.
Yeah.
Are you open to people cold messaging you in general?
Yeah, I am.
If they do, what do they have to do to increase their chances of you responding back?
Ooh, something focused. Like if I can actually help you with something. Don't just make it about like, "Hey, looking to connect." or something. Make it more specific.
Quick coffee chat?
Yeah, I know.
minutes? Can I pick your brain?
Yeah, those don't typically work as well these days.
Would you, Derek, be open to coming back to a future Office Drama episode?
Yeah, of course. This is fun.
Well, that's all we have today. We did it.
We did it. Inaugural episode done.
Episode one.
[gasps]
Wow, that was our first ever Office Drama episode. I hope you really enjoyed it. I had this show idea for, I don't know, like a year, but I never thought I could pull it off until now. In January, I was like, "Screw it, we're doing the thing. It's now or never. Stop thinking too much." So, I booked this really, really expensive studio in San Francisco cuz I just wanted everything to be beautiful. Then, I asked Derek if he'd be down to be my first guest, and he said yes, and I was like, "Thank goodness." I didn't know what pacing would make the most sense, so let me know what you think. I wanted to bring the essence of Jomo that I crafted so intentionally into Office Drama. I wanted these conversations to feel raw, cheeky, introspective. It feels like you're listening to friends catch up, and you get to hear some very insightful things, because honestly, I get the huge ick from business podcasts that feel super grindy and that make you feel really behind, that, I don't know, say AI everything, and then like uses accolades and Ivy Leagues credibility to get you to click in. It's just It's just a lot. I I also don't think that's healthy dialogue in this day and age, but, you know, titles and big brands really get that sweaty click. But, I really want Office Drama to be that cozy comfort podcast for the modern career and life, where you can be both highly ambitious but also a happy, healthy, good person. That's the majority of what I see in my real life, but it's not clickable on the internet, and I hope we can change that here. The episodes will vary a lot as I figure out where to focus the story with my guest. If I remember correctly, this interview was originally 2 hours long. Actually, most of my interviews have been over 2 hours, so I got to figure out what's going on there. We just have so much to say. There are several interesting segments that we are leaving as bonus content on our Patreon, so check that out. Also, this is just going to be so new to all of us. I think starting over a brand new project is terrifying. Starting a new podcast is terrifying. It's a really hard vertical to produce for. Like even for this episode, it really was just me and Kevin packing up all that we had in LA, flying all that equipment up to San Francisco, setting up all the lighting, all the set design, moving all the couches by ourselves, and just I don't know, just like literally managing an entire production day by yourself. And usually you have full teams for stuff like this, but I don't want to let perfect be the enemy of good. So we just had to start, you know? Oh, also I love our intro bumper trailer. Like the animation, the 3D blender characters, the the entire set design, the music. Like we spent so much time putting that together. I wanted something that felt new and fresh and upbeat, kind of like an Asian variety show with all this like Animal Crossing inspiration. And yes, I did voice the Animal Crossing sounds. Like the dialogue sounds. Like I was like So I hope you enjoyed that. The music went through several iterations. We wanted something that felt like chip tune, electronic meets anime, that was also Asian variety show-esque, and that was like super upbeat. Cuz yeah, business podcast and career podcasts are just so boring. Like there's no brand identity, there's no there's no excitement, there's no creativity. And I think, you know, career can be fun. Thinking about what you want for your future is is sexy, is exciting, is is full of dreams. Like why aren't we romanticizing and dazzling that up? So that is the the intention behind the design. I just wanted everything to feel cute, too, because um you know, Hello Kitty is my spirit animal. Hello Kitty with a knife, that is. So I hope you enjoy every part of this project. We put a lot of thought and effort into every single detail, but of course it's at the beginning, we're going to make mistakes, things are going to be a little bit awkward, so we're always open to feedback, but constructive feedback, of course. And I am so glad you are here for the first steps with us. Thank you so much for listening. I need to figure out what a good community name is. So far I'm like, "Uh, coworkers?" Well, like that sounds so boring. We'll figure it out. I had Jo Mies for Jo Mos, which I loved. I loved it, okay? Let me know what ideas you might have. Thank you so much for listening, and I'll see you next week.