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30 Years of Career Advice in 1 Hour | Deb Liu (CEO @Ancestry.com, VP of Product @Meta)

1h 15m 1s

30 Years of Career Advice in 1 Hour | Deb Liu (CEO @Ancestry.com, VP of Product @Meta)

Deb, a tech leader and co-founder of Maya Road, shares insights on building a successful career in a competitive environment. She reflects on the early struggles of launching Facebook Marketplace—its chaotic first launch and long, slow path to success—emphasizing that true growth takes time and trust. Her career journey illustrates a shift from aggressive, results-driven work to a more nurturing, supportive leadership style, where she learned to lead through collaboration, not control. She highlights the importance of self-awareness, advocating for women to recognize their unique challenges, including unconscious bias and lack of role models. Deb stresses that career success isn’t about relentless persistence, but about knowing when to pivot, change environments, or simply quit if conditions are toxic. She encourages authenticity in personal branding and underscores the need for women to build supportive networks rather than compete. Central to her philosophy is the idea of "repotting"—reassessing one’s path, team, or role when the current environment is stifling. She also emphasizes financial preparedness and escape velocity, urging professionals to build emergency funds and explore side interests to stay adaptable. Ultimately, Deb promotes a mindset rooted in iteration, resilience, and self-compassion, drawing from personal experiences to show that growth comes not from perfection, but from learning through failure and continuous evolution.

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So you are famous for founding Facebook Marketplace. It went terribly the first launch day. In my head, I thought it was like a blast of success. It was definitely not. The New York Times headline, "Drugs, guns, and baby hedgehogs." Oh, yeah, I've seen that. Story of a Marketplace gun wrong. It took a long time for it to be successful. Look, the job environment is not amazing and tech right now and I get it. You just need to be repotted. Maybe you're just the wrong plant and the wrong cut, right? Could you change teams? Could you change products? Could you change managers? Like, having all three be broken is a recipe for disaster. So you have three kids. Would you be down and take a forest? [laughs] Office drama. Welcome to Office Drama, where we define the modern career for Gen Z and Millenials. I'm your host, Chloe Shee. And today, in the office, we're at the Patreon office right now in San Francisco. We have tech royalty. She started off her career at BCG as an associate. And then she moved on to Paypal Ebay for like nine years or so, starting off as a senior product manager and then became a director. And then she went to Facebook and spent her career for 12 years, where she went from product marketing to product management to director to VP of the Facebook ad commerce platform and organization. And finally, she became the CEO of Ancestry.com for four years. She's also the co-founder and partner of Maya Road, which is a scrapbooking arts company and is a proud board member of companies like Poshmark and Intuit and she's famous for her sub-stack, where she's written over 250 articles on tech and business and has over four million views. She is the one, the only deb. [cheering] So excited to be here. I'm so pumped for you to be here. You have no idea. You're like my, okay, so you asked me who my dream list was. Like, you were definitely at the top. But I was like, I gotta wait for a little bit until I can ask her. Oh, of course I would say you're down. I know you would because you're like, you're supportive and you're a girl's girl. And I'll definitely get into that. I wanted you to introduce yourself really quickly to the viewers. If you can't just tell them your MBTI astrology sign, where you grew up and your age, can you do it? We'll see. Mars Briggs, I and TJ. I and TJ, E and TJ. Okay, astrology sign, Pisces. Pisces? Oh, I don't know much about Pisces. March. Okay, March. Yeah. And your age. Oh, okay. So I just turned 50. The big 5-0. Happy, happy, happy birthday. I think people should celebrate every birthday. Yeah. And this was special one. And I grew up in a small, small, small, small town in South Carolina. In South Carolina? Yeah. So it's about maybe half an hour, 45 minutes from Charleston? I worked in Charleston for a summer for at the Boeing plant. Oh my gosh. Okay. Very few people have ever been to South Carolina. I know. I learned about hush puppies and palm metal bugs and tornadoes at 3 p.m. and then there's a lot. Lightning. And then my coworkers were like, wow, Chloe, your English was really good. And I was like, thanks. It is a state when I was growing up that was, it had 16,000 Asian people in 3 million people. It was less than 1%. That's rough. It was just a very different way to grow up. That's so different. But I am so pumped to have you here. Do you remember the first time we ever met or talked? So I believe, and I was thinking back when I was coming. Oh my, you were thinking about me, Debbie. You were thinking about me? Debbie introduced us, right? Abby went. Was that the first time she had actually said, hey, there's a, there's somebody who wants to be a p.m. at Metta and she works in product marketing, I believe. I was in product operations. Product operations. Yeah. She wants to meet you and figure out how to convert into a product manager and then commit. Okay. Okay. So I was thinking to you on WorkChat, but I didn't even know if I could ping you on WorkChat because don't you have like EA's and stuff? But here's the thing. I had an open door policy. Oh do. So I used to have an open door policy at Metta where anybody could reach out to me and I would just spend 15, 20 minutes meeting with them. You were too nice. And I still have that today. So people would reach out to me and LinkedIn and I can't hit their heads. What? But like people, I just, yesterday I was like, oh, I'm walking the dog and I called this guy who reached out to me. He's like, hey, I started the startup and wanted some advice and he's from Duke and I was like, sure. Why not? Should I do this white comedy or thing? Wish Hashtag I think about X and I was like, the open door policy has helped me meet thousands of people. That's so much. You're not an eye. You're not an eye. You're an E. Well, it's where you get your energy, but I love helping people. I feel like the world is so much better if we just used five, 10 minutes of our day to help somebody. So I'm the opposite belief. I'm not helping anyone these days. Why did you give me a chance or is it just like you didn't really matter, open door policy anyone? Well, so the open door policy was really opened everyone. I actually started it because so I did new higher PM training. So I did a lot of the recruiting. And then when I did the training, a bunch of people just reached out to me and I said, and then part of the training I would say, you know what? Someday you're going to need a friend. It might be tomorrow. It might be two years from now. Just ping me. And it's going to be dead blue. And it's good. And then people heard about it. So other people would, you know, then people who are product ops, product specialists. I talked to people all over the company. And it was such an amazing opportunity to get to know people and get to know the company much better. You're just such a good person that I'm going to cry because I don't think you understand at that time, I felt like I was fighting the world to be a PM. And then I remember I was so nervous like pepping for our one-on-one. And then I was like, I better not freaking waste this woman's time. I better like show all my cards. And then we had, we hop on a call and then I just stayed like, oh, I would like to figure out how to transition to PM and choose like, oh, you were like, oh, I got a spot. Let's just like figure it out with the HRBP. And I was like, for the first time ever, I felt that in my career, I didn't have to prove myself. You just like had blind faith in me. And I was like, wait a minute. I don't think I deserve this. Hold on, hold on. What? You just gave me that chance and didn't work out in the end. But like, even your executive sponsorship of, let me just start the conversation and see what options we have without vetting me and testing me. It blew me away. Well, you know, I see the world's, there's people who say, you know what, you should trust everybody. And then people would say, everyone has to prove themselves. I'm one of those people to say, you should trust and then people will either rise to the occasion or they won't. But if you give them the opportunity, they have the opportunity to do more than you ever imagine. I've met a lot of people who are like, everyone has to prove to me that they're worth my time. I usually meet those people. And I, so I feel like if you give people a chance, so, you know, 80, 90% of the people will rise to the occasion. And so why would you basically filter out those people who feel like they have to prove themselves to you? And you know what? It may work out. It may not work out. People will not work out absolutely and I help them find something else or exit the company. But those who, I gave a chance to, thrived because they felt like for the first time someone had their back. Wow. And what was missing in their lives was somebody who believed in them. Yes. And they had spent the whole time like, maybe some people are really bad at striving and climbing. Yeah. But they're really good when someone trusts them. And so I said, why don't you come to my team? I will trust you. It doesn't always work out, but this is your chance to actually prove yourself. And I feel like that changed the mentality of so many people. Would you be down to take a fourth? In 20, I think 2022 or 2023, I asked you out to coffee on a date. And then you once again, we're like, yeah, sure girl, let's do it. And I was like, what? She does not test people. She does not test people because we talked about your bug, take back your power. And then you signed it. And then we had a coffee date and then I was going through, I think at the time started to do a little content, but I was still a PM at TikTok, I think. And then last year you sent me an email and it's called crazy idea. Yeah. Thought, thought, die. And you're like, hey, I have a crazy idea. Call me when you can. And I was like, out of the blue. So we hop in a call. And then you're like, hey, do you want to take a vibe, coding boot camp? And I was like, yes, it was super fun, right? It was actually really hard for me because I picked a really hard project. It was a whole project. Yeah, I was like, wait, this is hard. I'm glad I struggled through it and it made me appreciate my engineering team in the past a lot more. And I was like, I get it now. I think every PM should build up the fee because building, first of all, you learned so much more about your designers because design is hard. Signs hard. And by the way, when you try to one-shot it, it's terrible. No, one-shot it. Everyone thinks, oh yeah, just have whatever tools, just one-shot it. And you're like, that's not how I. It's usually really bad. Shut up. You know, but you have to really think through like, what am I trying to achieve? Use my ICP. Yeah. I think a lot of times PMs just take that for granted that someone else, they're outsourcing and thinking, actually taking buy-coding for you to make all the decisions yourself. And you can't rely on someone else's brain to help you. And so it was super fun to have you in the car. Yeah, thank you for inviting me. And that same call, you're also like, do you want to talk at women in product conference? Yeah. I was like, excuse me. I'm never even been. I'm like, am I even allowed to be there now that I'm not a PM anymore? And not only that, you all set me up with a panel with the one and only Ami Bora. I know. And I'm like, that was a very popular panel. That's a big stage. Well, talking about personal brand, in particular. You know what's funny? I don't know if we talked about this, but yeah, one in product reached out to both of us. And they're like, oh, can you guys do a talk on personal branding? And both of us were like, oh, we don't. We don't know what that is. But two of you have two of the biggest personal brand. Yeah. Really? I mean, I've never, I don't really know what that is. Like, I think I understand that we do have a vigorous on brand, but we're all, I've never thought about manufacturing that, like, that's what was magical is that you guys said it wasn't just about doing that. Yeah. It wasn't just like artificially pumping up your numbers and trying to be influential. It's really about authenticity and building, like, real connection. Yeah, that was really awesome. That was really fun. So I was like, I got so lucky to have that on stage experience with her and be part of women in products. I never got to be part of it before. Yes. Yeah. Every p.m. who was a woman would, like, look at that as a goal in their career. Take one. to go. So Deb, you wrote an article called 50 Lessons, you learn by 50, and that's on Substack, which we could go into, but then that would be like a full leadership summit. And this is for free. So I really wanted to dig into all of that, because I'm also known for the 30 Lessons by 30 series. And now Deb came out with the 50 by 50, and I was like, "Girl, we got some parallels." I bucketed everything into five themes, and I just wanted to share, or go over some of those biggest lessons in your life and career and work, and the first theme that I really observe is define success before the world defines it for you. And then you go on to be like, "You need to discover your life's North Star." It's a very tactical article, but my question for you is, at one point, did you see your world was defining your success for you and that you had to take the wheel for yourself? Well, I think it's so easy, especially when you're in corporate world, so you're chasing the next promotion. It's like a treadmill, right? Because once you get the next promotion, then it's the next one, the next one. I want a bigger team. I want this. I want to own more scope. I want, where does this end? What is the ultimate goal? And I realized that once you're on that treadmill, it is very hard to get off. And so, you know, one of the things I write about in my book was when I went to Stanford, the GSB, one of the things that happened was the first, I think within the first two weeks of us arriving. These were like 20-somethings. We are like right out in Bushytale. They asked us to write our obituary. And so we had to write down, like, what does our life look like at the end when we were just getting started? And when you write your obituary, what do you say? You're like, I was promoted to director at 28. Do you say I had a team of 250 people? That's your LinkedIn obituary. Right. You know, and I see that. And sometimes, by the way, I actually see when people pass away and their friends give them tributes on LinkedIn. I go to their LinkedIn and I read about them, but it's very cold. It's like, you know, it's just like a checklist. Yeah. But their lives are so rich. They have families. They have kids. They have all these experiences they had. And I realized, it's too often. It's like, you're just trying to add on one more line on LinkedIn to say, I've made it to director, then senior director. And I checked all these boxes. But what is it ultimately add up to? But I remember in your lifespan, you had this very chip on my shoulder. I'll prove it to you mentality. And of course, you were greedy. You were working so hard. You worked from a lot of quiet work, a lot of like, I'll show you. And it seemed like surviving to get to the top. What was the turning point that you finally realized? Well, got me here won't get me there. And I need to change from that attitude to like a more, I don't know, abundance, my set and loving mindset and loving yourself. I feel like you're really hard on yourself as a lot of second-gen immigrants. Yeah. Well, it just didn't do. Well, you feel like, you know, you want to prove that your parents made the right decision to come to America that you can make it, that you can fit in, that you can deal these things. But the huge turning point was actually, there was actually a CMBC article written about this, which was when Cheryl Sayonberg was my mentor and somebody who I worked with very closely. She pulled me aside. We were at this meeting. We had finally achieved success in our product. We hit product market fit. It was like, growing like a weed. And I made some comment and she pulled me aside. And she's like, you can stop fighting now. Yes. Yes. Yes. I wrote that down. I know. And she said it. But she said that because I had so much fight in me. You did. And I was always then, but you died. No, you can read all of it. I read all of it. I was like that person who combative, competitive, like all those things. You know, I am much more zen now. You're so zen. Well, you are abrasive too. I was probably very abrasive actually. And so if you think about it, it's like, I just was so goal oriented. I just want to get things done. Like I was very impatient. I was that person, people hate working with, but I was also hyper competent. I know. So you can't not. I know. You had the outcomes. So what are you going to do for you? Yeah. Except that you're irritating too. And so, you know, I think she was saying, like you, you know, show some grace. And you know, it's not like it's when it was fighting, it was more of the, you're so competitive, you're so combative. And I realized I was putting my energy in the wrong thing. Do you remember how old you were at this point? Probably about 2012, 2013 or so. It was like 13 years ago. So it was like, yeah, I was in my late 30s. Wow, that's a, you kept going until your late 30s like that girl. And I think it's important to realize that if you're really difficult at work. So I tell, I tell this guy who one of those brilliant people I've ever worked at, I said, the problem is your R is high, but your eye is also high, your ROI. Yeah. And every manager is measuring the ROI in their mind. If you return as high, they'll put up with a lot of crap, which means the eye is high. Yeah, yeah, yeah. But then you are constantly having to put up the numbers. Yeah. And I said, if you could just be a little easier going and less combative and less difficult. And he, and I told him the example of how I used to work. And I said, you don't want to make people have to work with you. You want to make them want to work with you. Did he say you well? He did. He actually got he, you know, and, you know, after some coaching and stuff, he's gotten so much better. But the point is, and I coach a lot of people in this section. It's like super high maintenance, super results. But the problem is the minute the results aren't going to deliver. Yeah. Then it's like, do I need to deal with this crap? Right? And I know people felt that way about me. So was that at, at that point in your late 30s, were you finding like, okay, you know what? I think I've made it. I'm good. Well, so I don't know if anyone ever feels like they made it. But what I realized was this path is not a path to success. And I realized that like at some point, what is the goal? What does success look like if you just keep wanting more? So then where were you, was your head at that time? Where was the transitioning to from promos to power to then Cheryl said that. And then you're like, yeah, you're right. Well, so that's the thing. It's like the thing that was rocket fuel for me. The thing that fueled my entire career was that combative. I'm going to show them. Yeah. I had to rethink my entire foundation and why I was doing something. And it forced me to really rethink like, how do I approach things? Am I giving out of abundance and generosity? Or am I just doing it because it gets me the next place? And it really had to do a hard reset on how I looked at the world. And I got this career coach who was incredible who helped me through this. I still have in contact with her today. She coached me all the way up until I stepped down last year. You know, what she showed me was that when you when you actually give out of abundance and you have an abundance mindset, you get so much more in return. I agree. I do think it's not a zero-sum game. I don't know exactly how it happened to me, maybe because I left corporate and I was like, yeah, whatever. So I feel like I operate from that mindset, which is nice. And I think life has been so much better. Yeah. Like easier for me. I've got no enemies from it. So that's awesome. Well, think about this, right? Think about like in your in your fields. Yes. You can collaborate with people or you can compete with people. Everyone grows if you collaborate. Exactly. That's what I think to the second theme is essentially how power actually works, which is a lot about your book, like the invisible rules of power and influence. Yeah. Your book is take back your power list. Let's be taken back our power. Rule number one is know your playing field. And what that really means is like when any woman enters a room, there is this invisible tax that you have to pay. Like people look down on you already, no matter what position you're in, and you have to be cognizant of those rules and be better than them, which is so exhausting. There's a funny thrust post where it's like maturing is realizing that what comes after healing is becoming the inner bitch you were always meant to be. I guess healing become inner bitch and then realize you don't have to be that way anymore and then you operate from abundance mindset. So there are stages of evolution. What comes after knowing the playing field? Well, I think here's the thing. Life isn't fair. You know, we are born with a lot of advantages and disadvantages. And we always say, well, you know, we just want equity for everybody. But here's the problem. Like some people like, for example, my parents came to America to go to college. By definition, they had parents who had enough money. They were not rich, but had enough money to send their kids abroad. Yeah. That already put them in the top, maybe 10% of people who could even afford, you know, from their countries back here. And then they were able to go to college, which again, only 20, 30% of the people at the time had college degrees. And so there's so many things where we forget that the privilege that we have is built in. You know, my parents became homeowners. They had a very successful life. Yes. And they lived the American dream. And was everything perfect, absolutely not. But at the same time, I lived with a great deal of privilege because we had a stable family. And my parents loved each other together. And you know, all of those things. And yet we often forget that. And in our minds, we're like, we only look at it disadvantaged. Well, so here's what I would say to women, which is, is there structural disadvantage for women? You know, I would say that a lot of the structural things have been taken down. But there's a lot of unconscious bias. You know, even the numbers, even today, I think McKinsey and leanon has been doing the study for, I don't know, like 10 years, where it's like for every, you know, it's something like 85 women promoted to manager 100 men are. So nobody goes to the 15 women and say, well, Chloe, you're a woman. We're not going to promote you. You wonder, well, what's wrong with me? Because it seems like everyone else is going just a little faster than me, especially the men. And so, you know, that's the level playing field I need everyone to understand, which is it's not the overt, okay, we're only going to, we're only going to hire a permitment. That's not what's happening. It's the same thing with VC. It's something like, you know, it's like 2% of the money is going to all women teams. And I think in mixed teams, it might be like 18% or something, right? So, do men have 82% of the best ideas in the world? No. Or is there something about unconscious bias? I don't think VC firms are like, hmm, we should invest only a men. That's not happening. What's happening? Is there something about that bias? And then the question is, what do you do about it? Because I think we were like, we should just make the world fair. And I'm like, absolutely, but not everyone has parents who are married, who went to college, who had grandparents, who had enough money to send them to America at a very fraught time in their country. That's how I think about it, which is, what do you do with what you have? And then how do we actually raise the floor so that we make it more fair for everybody? Do you think there has been a difference for you experiencing like the glass that ceiling versus the bamboo ceiling. Well, so I would say this, which is by the way, there's a study that talks about that, right? Ascend has done a study that said Asian women or something like. - Or 2016 study, I think. - Yes, it's my study. - I don't know. - They've done it updates since then. It's something like 13% of tech workers are Asian women and something like 3% of the executives. - Yeah. - And so one or two things have to be true. That those 13% of people are way worse than everybody else. - Oh, or there's something that's unconscious, right? And I don't think there's any structural barriers like we are not going to promote Asian women in this company. - Yeah. - There's just unconscious expectations. It's the same thing, my friends who are black women are like people expect us to be a certain way. - Yeah. - You know, and we have to show up a certain way. You know, I have friends who have told me, like you don't want to be like the angry black woman. - Yeah. - And I was like, they would never say that about an Asian woman. - No. - But instead, if you're an Asian woman, you're expected to be, you know, put your head down. - Yeah. - Do your client, right? If you speak up too much, you're like, - And so people experience you differently. And by the way, other women experience you the same way. And so if you think about that, I don't think, I think we've gotten rid of a lot of the structural barriers, but we have not gotten rid of our expectations of each other. - Yeah. I remember that study coming out and it kind of, not that it like manifested my future, but it really made me think, wow, I got it, I got to go extra hard. I got to room, room and rev it up because I don't want to be that statistic. And then I left, I got to do my own thing. - You did do other things, but not such a power. - Like here's the thing as a creator. - There's also not that many Asian women creators. - Oh my god, we are not, we can totally talk about this after though. But yeah, it's really lonely at my stage and I'm at a point in my life where I have no mentors and role models who are, you're definitely were there, where there's like no one who took your path. And so then there comes a point where you cannot really ask for help and advice. You can probably ask for it horizontally with your laterally with peers who are going through something similar. But you, the answer will come from your path. You will be the answer for other people to look at. And that's like a scary transition for me and I was like, oh shoot, I actually shouldn't be asking more questions to other people. I should just be doing like following the gut instinct and figuring out my intuition and just executing and building. So that's a, that's been a crazy journey and pivot. - But I remember what my coach told me. So we were in a meeting and I was, did not a VP at the time. And a colleague of mine kind of went in and we were the junior people kind of fixing a huge company problem. And everybody else in the room was VP. They were all white men. And he, who's, he's a black man and myself, were the people, the junior employees who were like fixing everything. And we did the presentation and we walked out of the door. And I remember telling my coach about this. And my coach is like, yeah. And I said, you know, it was really uncomfortable because we were the two people of color sitting in this room. We were the doers. They were here in judgment of what we were doing and giving us feedback. And she said, yeah, but when you're looking at them, they're looking back at you. And I said, what does that mean? And she's like two people who are very qualified, showed up and solved the problem. And they see you, the two of you, being the problem solvers, the solution to a huge problem the company had. And I was like, oh, I never looked at it that way. And she said, yeah, you're looking at them. But they're like, wow, you know, these are two people who don't look like us, but have solved this important thing. And so I guess that really changed my mentality, which is sometimes you're the first person to show up in that room. I went to a CEO summit and I was the only woman of color and like 200 people. And I was like, 200 is a lot. Yeah. And if I'm the only woman of color, but next year, if I show up well this year, they'll invite more next year, hopefully. And next year and the next year and the next year, too. How confidence is this? I went to a lot of CEO conferences. They were very similar to this. Oh, okay. But I think one of the things that is difficult is for us to realize that when you blaze a trail, it does feel really lonely. But then it gives people the opportunity to see this is possible. Oh, yeah, that's what you were to me, for sure. I was like, definitely the only one in that echelon that all of us can look to. I don't know if you had people you were looking to. I mean, you had Cheryl, but that's me and the one else. There's incredible women who have blazed the trail. So many nameless women who got the opportunity earlier on who had to fight their way into that room. Yeah. And I remember now, that's why I said in my role models, it was the nameless people who had to fight to get in, you know, to the sea suite of a steel company, you know, or like who was working in IBM in like, you know, 1980, who, you know, eventually they had a woman CEO, right? And so you can think about what it takes to get there. So that the unconscious bias when it hits you, it isn't as, it doesn't hit as hard. Yeah. So then I remember how many trailblazers had to bake it. And so then when I think, oh, it's really lonely, I think, but all of those people are forgotten in history, but so important to who we are. It's the end of September. We are entering Q4 and Drumalomas. This is a time we got to lock in to get our projects done by the end of 2026 because it's peak hiring season. There's new headcount. There's new budget to use before the end of the year, and your calendar is going to be stacked if it isn't already. So make sure to use granola. The AI power notepad built for the way real people actually meet. Granola securely transcribes your meeting. You can take notes if you want, but it's really there so you can stay present in the meeting, ask the important questions so that we don't have to have another meeting about the last meeting because no one took notes and no one remembers. And my favorite part is that after every meeting, granola spits out a clean set of notes and to-dos and takeaways. I usually just copy and paste that into the follow-up email right after the meeting and bam! I find that the follow-through rate on the tasks and to-dos with my stakeholders is so much higher. It's really the small things that get work done so tasks don't fall through the cracks. If your meetings are eating up your day, granola is a no-brainer. You can try it for free. Just head to granola.ai/office drama. That's granola.ai/office drama to get your time back. Try it for free at granola.ai/office drama. It's the world's second largest marketplace behind Amazon. It's ahead of Alibaba, Walmart, eBay, Talbao, and Craigslist. You pitched this in 2009, but then it took five years for execs to say yes in 2015 and then launched in 2016. That's like 10 years ago. Happy 10 years, by the way. You called it a five year overnight success. How do you remember how your pitch changed from the first rejection to the final approval? Well, actually, it's funny because it wasn't the five year overnight success. After we launched it in 2016, it took several years for it to be successful. And I wrote an article about the four year overnight success. It was actually took even four more years for it to be successful. I did not know that. And so I had just, during the interviews, I pitched Facebook Marketplace because I could just see what was possible with like local community and I really wanted this product for myself. It was selfish. I actually did sell something on Marketplace like the other day. But basically, I was like, think about the potential of building community commerce, true local commerce. And so pitched it every year, different forms of it. We tested wish list, we tested all of these things in commerce. And finally, in 2015, I got the green light to explore it and start building it. We started with Groups Commerce. Eventually in 2016, in October, we launched Facebook Marketplace The Tab. And it went terribly the first launch day. You can still look this up is October. I think it was October 16th, 2016. Wow, and my head had thought it was like a blast of success. The New York Times headline, actually, you have a screenshot of this, you can screenshot it, show it. I have a lot of sat New York Times. It's something like drugs, guns, and baby hedgehogs. Oh, yeah, I've seen that, yeah. A story of a Marketplace gun wrong or something like that. That was the day one. How did you feel? It's terrible because it was a culmination of everything we had built. And it just, it went sideways for, there was one specific bug that happened on the day of launch. And it was just like, one of those one million things. And then we built it back up and we got it to a great place. But it took a long time for it to be successful because you're really building something brand new. Yeah. But it was such an amazing adventure. And four years later, I think four or five years later, we announced that a billion people were using it. And that's really what success looks like. Is really changing local commerce. But I thought Facebook wouldn't like nick something if it had a failed attempt. So how did you keep that positivity of float within the company to let it keep going? Well, so part of it was, it was that belief. It's like what is possible? And there were a lot of products where it was fail fast, right? It was succeed faster, fail fast. In fact, Facebook Marketplace was one of those not succeed faster, fail fast. It was like a slow burn product, which is not that popular at tech companies. But also, we could see like it was actually powering local commerce. Like people were doing things. People were buying things from the community. And so, you know, every year we got another year to keep working at it. And now, you know, it's amazingly successful. And yesterday, I was really excited to hear it. They launched a Marketplace Cellar app. - Yeah. - So congrats. - It's really exciting. - So it's still used it. - My son jokes, like I get a lot of cred because, you know, that's the only part of Facebook that all my friends use because he's in college. - Right. - So young people love Marketplace. - Oh yeah. - For sure. - So I'm so excited. - I'm so excited. He's like every young person in college uses this. And this is why we're on Facebook. And I'm like, well, I hope you use the other things, 'cause I love all the other things too. And he's like mostly Facebook Marketplace. - I know you just write it off as like we got another year, we got another year, but I think that the storytelling and the narrative telling you have to do internally for you to even get the chance of another year is so hard. I remember when I was at Discord, we launched Forum Channels, which is like essentially threads, but in a new channel. And now it's like a lot of people love using it and I use it. But it took a really long time for people to adopt it. And we basically saw no impact growth. Like in our impact metrics, we saw no change. And then they're like, well, do we cut it? And I'm just like, but foundationally, foundationally. This is really good, but that wasn't enough an argument. And then I got dinged on my performance review and I was like, well, good things take time, right? But it's not sexy. It's not sexy. - It's not sexy. And I think sometimes we expect the overnight success. We launch and it becomes amazing. And yeah, do some things take off absolutely. But you think about a lot of products are slower in products. It takes time to get adoption and it's not an overnight success. And I think that that's what makes it something really special is that if you really believe that there's a value on the other side, can you convince enough people to believe with you? So were you more of a qualitative storyteller and like anecdotally giving examples to the exact team to be like we need another year? So we would every year we do our product review and every year they were like I don't know, you know, and every year got another year and so it did take a long time though because my team was really behind it. They worked so incredibly hard and I said you know it's just one of those things where the the thing that ultimately now is has proven its value is that it drives people who would otherwise not use Facebook to it, but it's very hard to prove that. It's so hard because it takes forever incrementality as you know is impossible to measure in a short term. It was like downer and he was like well I think he was like he he understood why we wanted to build it. Okay. And so he really believed in the mission. Okay, but it just didn't show up in the numbers and here's the thing we all work at tech companies with the numbers. And numbers are your forums right? Yes and say it's like well it's not really hitting the numbers why would we be doing that. So you just had to use your personality and be one. Just believe me guys. Trust me. Trust me. But I have the vision. But now you know it's a mentality wise it's like you know it is my son and his friends who use it all the time and say it's like this is the reason we use Facebook and Messenger. And so I do think that it ended up having a great story for the company but at the time that was not the reason we built it. And you know sometimes you just have to align with the strategy of the company at the time when meet them where they are. That's that's a journey. That's a journey as a super successful woman at the top of tech. Do you run into woman versus woman problems? Never. Oh really. So I do write about this in my book about Queen Bees Syndrome. Yes. And the most supportive people in my career of the women. You know I've had a lot of male mentors as well. But some of the best people. And so there's a there's a study about Queen Bees Syndrome. And I included in my book because it drives me crazy when people talk about this. The only time that women hate this. I know. I absolutely hate this. The only time that the women are actually against each other is when it's made clear that there's only one slot for a woman. How is it made clear that they're okay. It's like so the studies were so the studies were talking about law firms. They usually only have a one woman slot for a partner. But the nights come out. So you know often there's like there's only one woman on you know it's like we're going to have a woman on executive team or one woman on the board or whatever it is. And suddenly it becomes very competitive. But I have never experienced women versus women in that same way because I think that you know actually studies have shown that when there's actually like two with like women on boards. Yeah. The minute there's two women on the board there's like three four five women like the numbers go up that's like yeah. And so you think about that right. Women are actually helping other women to like get opportunities to get the chance to interview. And so I have not experienced that. I think when it feels like a zero-sum game that's when it's difficult. I feel like for a lot of people watching I think a lot of us have experienced a zero-sum game very aggressively. Have you ever heard the you know I'm not here to make friends I'm just here to work mentality yeah yeah okay well here's the thing some of my best friends are from work yeah some of the most important connections I mean these are people who invest each other's companies they like you know they help each other when they are recruiting they get each other jobs that I hate that mentality there's kind of this new mentality is like I'm just here to work and get the paycheck I don't do any extra yes but then you're losing out on so much and so when I say make friends at work both men and women these women that I knew from before you know these are people I'm still friends with to this day and I don't see that kind of mentality I've been in three four lean-in groups now and these are some of the most supportive women these are the women who open doors if I need anything I can call on any of them to get anything I need done you know and so I just feel like I've had such a community of support like one of the lean-in groups them in is like all the women VPs Facebook from a certain era you know one of them is like you know a bunch of people that had worked together previously another one is just like a one in our community but you can call on these people day or night to do anything and that's the thing I feel like is is too much in the new mentality of like you know work is work it's very individualistic right now and I think like think about what we lose in that sure I understand with playoffs like you know companies are not families I get that but at the same time your colleagues are the ones who are going to get you your next job they're the ones who are going to introduce you to the right investor they're the ones who are going to help you find a co-founder someday they're the ones who are going to introduce you to the person who's going to promote your show like that's how it works and so I don't know I'm too worried I'm worried that young people are kind of taking the wrong lesson from the layoffs and feeling like they're very disconnected from work yeah they're gonna lose out on something that's so rich I truly believe in that that one quote rising tides raise on both yes but I don't I don't think that is the majority mentality actually I think people are very I'm gonna gatekeep what I know to me and people are absolutely trust and wonder if it's a generational thing with like the internet and everyone having this personal brand and everyone trying to like make it on their own it feels very individualistic but why why does this woman's success take away from someone else's success I don't know I just don't get it I don't get it either but you're so generous with your time with people who are sparring creators and want to learn apparently I'm rare apparently like it's like you can have very successful creators you can have thousands tens of thousands hundreds of thousands just giving away your playbook make it that different maybe because people are transactional like in this space you know I we just talked about right before this recording where like even in podcast interviews and people who want to collaborate people only will do it not for the relationship and the long-term benefits but just for the cloud and the clip and the clickbait and you feel that and you're like I shouldn't have access to that person and then you put your walls up and you continue to put your walls up so I've seen a lot of walls going up lately so every year my daughter Bethany who we're right to call them with for as am news she writes the lessons I learned from my mom so last year she wrote one when we were in Taiwan and then she wrote one this year when we were in Amsterdam and this year was like five things I learned about relationships from my mom and I was curious what she was going to write so she did it romantic or okay connections and I I have never really said these things to her but she was you know she talked about like you know be curious not critical and then there were some things where she was like mom just like helps people yeah and then people like drop off food and flowers and stuff at our house and I was like I guess that's true right so it's just you know for her she just sees that and I said you know I'm like you to live a life in the same abundance where you feel like you can give to others and it's not taking away from you the third theme that I got from your list of 50 is essentially becoming a leader without traumatizing others because I know you were gritty you were hard to work with aggressive whatever you have high standards you had something to prove and I feel I am an ENTJ Scorpio and sometimes I'm in a little bit in the it was so hard about this like what can't you do this to the mindset and so it's not the most constructive or helpful or positive I wanted to ask you what your evolution of leadership style grew to be from this aggressive to assertive to peaceful and now encouraging like yeah how well so you know I was exactly like you when I first became a manager you see me I see myself when you described it I so I remember when I first so I like objectively I feel like I learned so I started in product and not didn't know anything about it and but I really had so some people just have great product instincts I didn't really know what a parent product manager did but it was like I know what I want to build and I know I can work with people to build it and so that was my home mentality so I write these specs I knew I knew exactly I just had so the the skill that I had was good product instincts I had to learn the rest of it and to I would coach these new PMs they would these APMs joined our team and I was their manager and I was like they're so slow and they have like terrible product instinct and it's taking forever and I'm like this is so obvious and I was like I can't they know right I can't figure it out yes and I was like I could do this so much faster than teaching them and I went to my manager and I said that and I knew and he was so gracious he was like you know that's true because you are very skilled like the reason you're a manager now is that you're very good at what you do yeah here's the thing you can't scale you need to learn how to do through others right yes yes because when you do here's the thing when you said it everything yourself on all your videos yes right yes it was perfect and then when the first time you had someone else do it it was like I want to pull my hair out yes then you're teaching you know you're teaching them every day you're teaching them they're getting closer and closer and you'll find some kids it's like why can you not just tie your shoes or yeah I gotta tell you potty training I have never resented my kids as much as during potty training anyways thanks in your couch it was it was a mess like I we got rid of the rug let's put it on and so one of the things I think it's one of those things where it's like so obvious yeah some people and so obvious like toilet hello there was like what are you doing to show you this the whole thing is you know what you realize then with kids is that you know my my friend to Margaret she's an incredible manager she said having kids was the best thing to teach me how to be a manager because you want your kids you know they're gonna get there and you know you can teach them but you have to have infinite patience because you love them infinite and so I was like oh my gosh then my kids were very young when she said this to me but I think one of the things that I think you know each each of us need to learn is that you are the expert but you the best thing you can do is actually extend yourself by basically working through others and the problem is you know you're the best because you know exactly what you're looking for yeah so how do you teach someone to edit better than you you can't unless you figure out how to break down your process and actually help them understand and that's the same way as a manager and I was so impatient I was like I literally write that spec in five hours and spend 50 hours. - Exactly, why did you take 20? - Yes, this is not a waste. - I was so frustrated, but my manager really helped coach me through it. It's my first time managing. I probably should not have been a manager at the time. I'd been a PM for like approximately two years, so I had no idea what I was saying. Anyways, and so he said, you know, when you work through others, this is a totally different skill. And so I had to learn how to actually lead through others. And that's something that's a totally different skill than managing. And the problem is we always hire our best I see to become a manager and they're like, the worst person, because it comes the most naturally. - Yes, it's like that. It's like, you're most naturally comes to you and it seems so easy to you and it's hard for others. And so actually some of the best teachers are the ones who had to learn piece by piece, the process. I was that person who had great product instincts and didn't know how to explain it to me. - You just had the sauce and not the sauce. I was like, but I was terrible at managing. - So your first step was like, okay, I'm gonna reflect deeply and figure out how to break it down one tiny micro step at a time, and then be able to like say it word for word to someone else. Right, so that's what I gotta do. - Yes. - Am I not allowed to be aggressive anymore? - But you can be aggressive. You can actually set high standards, but not treat others with aggressiveness. Does that make sense? - Okay, okay. - You can hold the high bar. Okay, high bar, I got it. - Yes, I got it. - But then you actually say, you know what, this was 80% of the way there. And here's how we close the gap between 80% and 100%. - That sound like patience. - Wait till you have a baby. - You're just a good, you're just the best person ever. You're like, I don't know how to say it. - I have to learn this the hard way. - There were a lot of people who had to report to me when I was not in this arc. - I really don't believe you. I believe you were evil. - No, I really had an arc that was not good. - You were an evil arc. You had a good idea. - I don't know that I was evil, but I would say that I was not the greatest manager to report to. - Let's put it that way. - The fourth theme is when to persist pivot or change. You say don't mistake persistence for progress. We're taught that grit is the path towards greatness. - How do you know when to essentially persist pivot change? When do you know how to change the method? Change the environment or change the goal? - First, I'm writing a new book on transitions. - You're writing a new book? - Yes, go on. - You're not to down. - So on transitions, and the first chapter I wrote is quit. - Wait, quit. - What? - Everything, quit everything, quit now. - What do I first not working? - Okay. - You know, so often I see people, especially they have terrible manager relationships or they're in the wrong role or they have unreasonable goals. And I'm like, okay, you can fix all those things. - Yes. - Or you can just find a new situation. Maybe you're just the wrong plant and the wrong plant, right? - Repotted. - And so somebody gifted me this plant when I had breast cancer last year and I had surgery. And the thing was, it was not thriving. I couldn't figure out why. And realize the pot was too small. So I just had to buy a bigger pot and more pot. And I needed more soil and I need more water. And then I put it in a different place. And suddenly this plant is like three times bigger than it. And now I have to repot it again and just giant pot. But the point is, sometimes just like you're being constrained. You're just in too small a pot. It's just the pot that gave it to me and was too small. And I needed to repot it. And I'm gonna do that again. And the thing is like you only grow when you're in a new, blossoming a new soil. - In the right pot, in the right soil. That's true. I think the wanting to quit, isn't an intuitive thing for people? - We can't really tell people to quit even if they say it all or like break up in that toxic relationship, right? But actually I think that so often I coached, so a lot of women call me, especially women call me. And they say they tell me everything wrong with their job. And I'm like, well, why are you still there? And they don't have a good answer. And like have you looked for another job even? And they've not even considered like changing teams, changing managers, changing products, changing roles. They were just like, oh, I thought if I just tried hard enough, I could fix this. - Fixers. - Yeah, it's sure. Can you fix certain things? Absolutely. But by the way, and I actually kind of measured this for a year when a lot of people would come to me with these the same problem. Most of them, more than half the people stayed in the situation. And of those very few people turned it around. And then the people who left, more than a vast majority of the people who left and tried something else were way happier. - Yeah, yeah, you just shoot to the moon. - Yes, it's just, sometimes you just need to be potting. And look, the job environment is not amazing. And tech right now and I get it. And so like, could you change teams? Like having the right combination of those things is really important. And you know, having all three be broken is a recipe for disaster. - It is. I love how you mentioned, make sure you have enough escape velocity to make that next move because you can't just like Willie Nilly quit and still have rent to pay off. Or like want to become a product manager when you're not, you don't have the background for it because it's a hard role to go into. You tell people instead of going for that promo or that new opportunity, ask yourself what experiences must I collect to become qualified for the future I want? 'Cause that's the next step. After you decided to quit or to pivot or to repot, you got to make the plan of action to get there. And I really love that 'cause that's a tactical piece. Yeah, it's very easy to tell people like just break up. - I know. - And just like quit, like life is short. Life is short, but also life is really hard. - But you also need the tools to actually quit. You need either the safety net. - Yes. - So one of the things I think is really important is having, you know, I think more women need an emergency fund. - Yes. - So just in case something happens, if you get a layoff, there's a situation in where they're housing, you break up with your boyfriend, you're living with, like, you need emergency funds. So that's really important. And, you know, number one, financial piece of advice. - Like six months savings. - Six months saving accounts of your spend. - And like, know what you're gonna fall back on. So if your parents live nearby, you're like, they have a place for you. Okay, you don't have to worry about rent. - Where's case scenario? - Yes, or if you have a friend who has an extra room that you could rent, like, just in the back of your mind, just in case, like, have an emergency plan. I think so many people are just like, the day-to-day, they're living paycheck to paycheck, but they don't realize that they're like, one paycheck away from something really disastrous. The other thing, though, I would say, is don't just put all your eggs in your current career and your current role. Think about the whole thing about your escape velocity. I write about this, which is, what are the things you should do outside? You know, maybe it's learning live coding. So go learn something, you know, really figure it out. Like, make connections. - So, are you the eldest daughter? - No, my sister is a little older. - Oh my God, well, perfection is the enemy of the, well, eldest daughter of an immigrant family. It's also the enemy of a lot of corporate people that I've met and everyone wants to not be cringe. They wanna look perfect in their first post and they never want to look like they've ever failed in their life. And you reference a Chinese saying, "Ibu Tantin," which means trying to get into heaven in one step, but one cannot reach perfection in one step. You need to take life iteratively one step at a time. I'm sure you have a lot of very perfectionist people who go to you and be like, "How do I do this?" How do you shake someone who's so locked into their own perfection and they cannot let go, but they need to take their next step iteratively and to discover themselves? - Well, first, I feel like we have this paralysis around perfection. - Yeah. - It's like, your first post should be perfect. - Exactly. - But here's the thing, like, if you build a product and it's, what startup built the product, launched it and it was perfect, nobody. - I'm no clue. - And so every product you build is an iteration. It's like, oh, when you build forums, when we worked on Marketplace, it didn't work for the first time because our ranking was off, our notifications were off, we didn't have top picks, our search was not great. There were so many things broken, but the thing was we launched it, and then we figured out what was broken. The problem is if you never actually iterate, and so in our career, it's like everything has to be perfect. I have to check all the boxes for this qualification to even apply for X or-- - Yeah. - But you iterate, you get feedback. You say, hey, I applied to speak at this conference. They said, no, because of these things, now I gotta go do these things. - Yeah. - The thing is, you're getting feedback and say, why would we, so I wrote a bunch of articles around like how to PM your career, like you see your product. So many product managers do these amazing things for their product, and then they don't do anything for their career. - Yeah. - The thing you do for your career is you iterate, you test, you see what works, what doesn't work. You see what resonates with people, you connect and see if it works. I just feel like that process teaches you so much, and you're now in the learning mindset, and you're getting feedback back. And then I'm like, why would you just want to just, it's like, you're gonna launch the channel. - Yeah. - And you're gonna, I know exactly what I wanna do, and I'm gonna film all of it, and then it's gonna put it out there. No, you actually say, what resonated? What are people telling me? Who are the kinds of guests that worked well and what didn't? And suddenly, your product is getting better, like 10% at a time, but then 10 shows in, it's gonna be 100% better. You know? - Yes. - And so I think it's that kind of iteration that's super important. And I feel like we don't do enough of it. It's like, we're just like so heads down. And you're like, I'm just gonna launch a perfect product. My career's gonna be perfect. I'm gonna apply for the perfect job. And then I'm, no, interview, I always encourage people just like, be out there. You don't have to be interviewing all the time, but be out there and see what people are reaching out to you for. And if they're not reaching out to you, why not? And then talk to a few people. You don't have to say yes, but at least get a sense of like, what does the market look like? You would do that for your product, but you would do it for yourself. - I think maybe it's back to for women, and especially the invisible tax part, where you have to be better than what everyone perceives you. So you don't have room for mistakes. And maybe that's where a lot of people-- - But this is where the network matters too. - All right, say more. - If you have someone vouching for you, that tax is much lower. - Your fifth theme is, and Vision has a cost, so decide what is worth paying. And a lot of it is like writing about the motherhood penalty and the fatherhood bonus. And when I first read that, I was like, oh girl, no. You have this article of like, try to never forget, and this is one of them. - Yes. - You want to describe what it is. - Basically in multiple countries, including the United States, the men, when they have a child, they make the same amount, or even more, in some certain cases, and women make way, way less money. - Way less, visually way, way less. - That was a crazy chart. I knew it was like-- - And this is by the way, A lot of those countries have very generous. parental leave policies for men and women. So this is like Sweden and Denmark and Germany. So it's not just like the US where we have almost no parental leave. So. - Thank you famously stated that your career is stagnated for about seven years and you didn't get promoted. In fact, you got demoted and that was really hard. But you also say children can alter the timeline without changing the trajectory, which I found pretty beautiful. But I'm currently in that phase of motherhood right now where I am deathly, deathly, afraid of losing my velocity and having to ramp back down during the stage. But I know it's like time. It's like, you know, but we planned for this. We decided this is the choice that we were gonna make. But it doesn't mean I don't like feel it. - Yes. - What advice do you have for a little Chloe? And for all the mothers out there. - Yeah for the mothers out there. - You know, when the six years old's having kids, you know, so I had three kids and each I had them spaced about two and a half years in heart. - And it really slowed down my career. Like I just felt like everything stagnated and it was difficult and but for the fact that I had incredible mentors and managers, I am still here. First, we tell women that they can have it all. But then the reality is, when you feel it and you're like, I can't, it's something wrong with me. So a lot of women turn it inside themselves and they're like, well, I'm clearly the one who's doing a bad job because I can't have it all. No, actually very, look at the stats. Women are not having it all. It is very, very difficult to have it all. And even someone who has been very successful can, you know, I can look back and actually tell you the story because I'm successful on the other side, but so many women during those six years drop out. - They do, a lot of my peers in the creator space, they just stop, they just disappear. And I'm like, wait, but posting content is our lifeline. Like, we can't just disappear. So it terrified me and I really wanted to stay and compete and keep going. - But first, if you don't acknowledge that there's a problem and that there's something you need to solve, you're not prepared for it. And so I think you saying you're preparing, that's really important. - Okay. - I think people just assume, oh my cruise, I'm just gonna take a few months off and I'm gonna come back and it's gonna be exactly how it is. And I'm like, not at all. Because you lose a lot of momentum when you're out of the workforce for like four or six months, you just lose a ton of momentum, right? All the projects you're worked on are taken away. You have to restart them. Like, you know, everything that you've been championing, people forget who you are. Like it just takes time to restart that velocity. And so I encourage you to really think about, you're making this decision and you're gonna come back and it's gonna be hard. What choices are you gonna make now to make sure you're ready? So make sure you have a manager to come back to, the role that, you know, define the role ahead of time. All of those things matter and actually wrote about, you know, how to come back well from attorney, how to go out and maternity leave and how to come back well in a corporate setting. So you could read about that on my blog. And I write about that because no one prepares you. No one. It's literally no one tells you, oh my gosh, this is gonna be hard. And so you go in with this like idealistic, oh, just gonna be gone out for four to six months. And then the entire org has re-orged. You have like a different manager. And by the way, that happens to me multiple times. You have a different manager. Your projects are all taken away. You're like assigned to a new team and so you're like, you're floating. You're floating. And so many women actually went through this. There was one woman who came to me. She's incredibly successful now, very well known. But at the time she came back and she didn't have a job. But they physically had to give her a job because obviously they, you know, you can't just hire her. Fire laws. So she was like, she was just floating for months. And so, - Wait, did she like that though? - No, I think she felt-- - No, she hated you. Because she felt like her career had just like, it was like, you know, being snipped from a rope. You're just hanging by yourself. And she was like, I have no team. I have nowhere to go. I don't even have a role. So at some point, they're probably gonna get rid of me. What am I gonna do? So I put her in touch with a bunch of folks. And she's like, I felt like no one was on my side when I got back because her manager had changed, like, had moved over to another role. So she was literally left by herself floating. But they kind of had to give her a job. So she kind of was in the organization. And I was like, this is somebody who's like super competent. I worked with a four. - A super star. - Super star. The thing is, she was in a different part of the work. So I couldn't take her on my team. But I was like, let me just introduce you to other people I know in your function. But the point was, I just remember how frustrated she felt. - Yeah. - And I could feel it too. - Is there anything you would redo differently? - I think you can go back to your family. - I think I would have wished somebody told me that had completely unrealistic expectations from my career during that time. - I think I do too. (laughs) But now looking back, it turned out that it was a pause, but then it was a springboard to the trajectory that I had after. - I love how you say, solve for joy and the rest will come. - Yeah, that's a beautiful quote. - I stole that from Eric Bond from Hustle Fund, by the way. - Okay, well, it's okay if I just credit that to you. (laughs) You say, ambition without joy becomes brittle. So we got to optimize for it. And it's kind of like how Elissa Lou, when she was doing her performance, she was like, you can't beat someone who's having fun. So fun, maxing, became. It's trend online, but of course, it originated from De Blue here. How do you know when someone's living and operating from the state of joy? Like you and just telling, sniffing from their energy? - Well, so I've seen this happen a lot at work where you're working with somebody and it feels heavy. - Okay. - It doesn't feel right? And so I've had this talk with many people where I said, I feel like you're barely, you're swimming and you're barely keeping your head above water, I want to see you soar. And you can't soar in this job, or this role or this product, or there's something that's keeping you weighted down in the water and you're struggling. And so many people are like, no, no, I'm just like, I'm gonna figure this out and I'm like, or you can find a place where you can soar. And let's go do that. And I think you know when you feel it, when the winds at your back. - And someone's just? - Yes, my coach calls it swimming downstream, right? When you swim downstream, it feels easy. - Oh, yeah. - But when you're swimming upstream, I don't know if you've ever seen salmon trying to make it back to their smiling. They literally look like they're standing still because they can't, the motion of the water and how hard they're working. By the time they get there, they've used up all of their reserves. And you see that happen in people's careers where they're swimming upstream and you feel it. It's, every day is heavy. And so if you can find a place where you can have joy, whatever it is, like even if you can notch it a little bit differently, it's like, maybe you change your environment. Maybe you change where you're sitting in the office. Maybe you try to, you know, work from home two days a week, whatever it is that helps you find a little bit more joy. And then figuring out how do you ultimately find the place where you feel like you're soaring? That's gonna be the most important. Is there like concrete signs when someone's not operating from a place of joy? Well, I just remember working with this PM who was incredible, but I just, every meeting we had, I just felt like she was so unhappy. And I just, she's like, yeah, she's like, I got stuff to say. Well, no, it was not that. It was, you could feel she was, that the role had changed. She was like an amazing executor. But she hated doing like, we were doing a ton of executive reviews. It was under a lot of scrutiny. And she just hated doing presentations and hated doing that part. But she was just shy. And yeah, and it just, it felt like every day she was dragging herself in. But ultimately I said, you know, let's find you something else. And I think it was hard because her identity was so tied up in the product. Right. But at the same time, she went on to soar in other places and went on to do amazing things. And you know, this happens multiple times. There was one person who moved from one product team to another and it was just a bad fit. I'm like, I need you to go back to your old product role because that role was much more strategy. This one is much more like tactical execution. She's like, no, I can do this. And I said, every time I see you, I see you fighting. Yes, you're not, but you are incredible at the strategy stuff. And that team is really focused on that. You hate the, you know, a hand-to-hand combat. And you know, eventually she went on to go back to that team and got promoted. And so again, you know, she could have fought it out, but eventually, it made, but it took me over a year, maybe two years to come into her back, actually. But in the end, you thrive when you're in the right environment. I think that people intellectually know that, but they're having a hard time letting go of the image that they're supposed to keep up, that they're supposed to be able to do it all. That there are, I mean, especially people, now in my 30s and a lot of people are here, it's hard to shake off old habits. I see a lot of high impact, high achieving people who cannot let go of that identity because that's who they've been their entire 20s and into their 30s and they look perfect on paper, but they're actually highly insecure, high anxiety people who are fighting demons every day. They just cannot get over the insecurity of like not being enough, not doing enough. And I guess this is a part of like the when is it enough? Conversation with the, I need to be perfect conversation with the, I get intellectually get joy, but like, I can't do it yet. So what does it take to make that change? Look, when you build products, most new products fail. And yet we expect that we take a product role or take whatever role and yours just to be perfect. - Yeah, why? - At a, why? - Crazy. - Why do we expect that, right? Why do we expect it's like, you hit product market fit with every role, with every manager, every single time. That's impossible. And yet with our products, we're like, well, you know, it's not for everybody, right? Not every product's for everybody at this time and that's okay. And so I think we, but then so many times people say, if I quit, I feel like I've failed. And I'm like, no, you're actually running towards something better, which is leaving behind what's not working. But in our minds, we have been trained, especially type A people go into tech and go into these roles, right? It's like, if I give up something, like let's say you try something new, like you try writing, you know, something, and it's like, oh, it doesn't work out. You're like, I'm a failure. But that doesn't mean everything else you're doing is not working. You're experimenting with 10 different things in your portfolio. And I think often we have that same thing with our careers. Like, if this job didn't work, I'm a failure. - Yeah. - Because when we're in school, we had to get A and A's in all the classes. That's the problem with school. One of the things I loved about working at Facebook, and I really wanted to instill this in Ancestry, was, you know, play to your strength. Some people are really great at certain things. You don't have to spend all your time fixing all your problems. Sometimes you just let people play to their strengths. And if their strength, if towering strength is amazing, then cut out the stuff that they're bad at, as opposed to making them fix all the things that they're just not that great at. And so I do think one of the things things that we should think about in our careers is like, don't see it as a failure. See it is going on to something better. - Ooh, I like that, I like that a lot. So if your mantra is operating from joy, is that what your new venture is about? - Yeah, and your motivation for it. What is it? What's this, what are you doing? - What are you doing? - What are these days? - So the vibe cutting class you took, it actually, we actually ended up creating a platform and now we actually bring AI into organizations. So we worked with a professional services organization for shipping, logistics, basically organizations that don't have software engineers. They're left behind with, you know, you can't build, it's like, it's hard to build and host your own agents. And so what we do is we actually come in and help you figure out your strategy and then we actually implement workflows to help you save time. It's really focused on, you know, there's like 20, 30% of jobs, like A job, a single job, that like, it's just a waste of your time. It's like, I'm moving like this from this excel street to this excel street. I mean, you're doing reconciliation between two things, like this system and this system, we automate a lot of those things so you can actually free up humans in your organization to do the things that only humans can do, which is the creative stuff, like talking to clients, all those things, I think a lot of times people were like, "Oh, just take AI and replace all these jobs." I'm like, no, no, no. What if you took AI and actually unleashed human creativity? - Correct. - And so that's what we do is we go into organizations, we help them understand where are you spending a bunch of time that could be more quickly automated? And then how do we actually free up those people to do the things that literally, "A, I will never be able to do for you," 'cause they don't have the judgment, it doesn't have the history, and free up your team to focus on those things. - What is it called? - So, it's Ember.New. - Ember.New. - It's Ember.AI, but our website is Ember.New. And we work with a number of different organizations, but it's been super fun because, you know, I could just see how AI can transform organizations. We partner with some private equity firms, we work with a bunch of professional services companies, but a lot of the companies are ones where, you know, they don't have engineers. And so, they don't have a way of securing data, they don't have a way of building workflows. And so, we do it for them. - Oh, that's awesome. - It's been a super amazing adventure, and we're having a great time. - You started this year, last year? - So, we started it, you know, we started it just last year, so it's been about six months. - And you're writing a book? - And working on the book? - Although, it's slow going, because obviously, I don't have a lot of time, but, - For sure. - It's been super fun. I still write my sub-stack as well. - Yeah, and you're on it, that's amazing. - I wanna ask you. Now, you've seen me throughout the years and online, and you've had this conversation with me. What are you excited for me to do, and what is a warning for me? - Okay, that's a good one. Okay, so, I would say, if I had to take a word to talk about you, it's fearless. - Oh. - Because, you know, very smart. - Well, I think you're willing to put yourself out there. You reached out to Abby. - I did. - You didn't know her. Then you asked you reached out to me, and she reached out to me, and I said, "Yes." And you've reached out to so many people. You've, like, you put yourself out there. - I do. - Do you have my rejections? - I do. - And here's the thing, that you don't let the rejections bring you down. - It's a no for now. - Yes. And so, I really think about the world as people who are willing to put themselves out there and not, and I think that you've put yourself out there, and, like, you don't know what's gonna happen, and that's okay. And I remember when you recorded your layoff reaction video. - She saw it. - I saw it. - I was like, "Oh, my God." - But, you know, it takes a lot of courage to put yourself out there and say, "You know what, this is a very vulnerable moment." And you were like, "I kind of suspected this might happen." I'm kind of, you know, but you, like, said, you said the things that everyone feels, and I think that's why it resonated so much, you know? - What? - And the thing is, you told me, "Hey, I would love to be able to do this creator thing." And at the time, you were at, you know, I think you were at discord when we met for coffee, right? - Yeah. - And maybe the, the right, the right, yes, was somebody saying, "You know what, this layoff is the reason why you had the courage to do the thing." - It was a sign. - It was a sign. Sometimes the best impetus is the worst thing that feels like happened to you. - Wow. - You know? - Yeah. - And so I feel like you are showing people that you can go from something that is a huge loss and a huge, I mean, you loved it there. And so you're like, you lost something that you really cared about, but then you used it as fuel for the next thing. - Yeah. - So a stumbling block can become a stepping stone and a springboard. - You're full of bars today. - Yeah. - Full of bars today. - The one warning I would say is, is creating is hard. - Like a baby? - Yes. - Like life is hard. - But we're saying creating like stops. - I'll create. - Well, I think that influence, like being an influencer or a creator, it is really tough out there. And I just see how much burnout there is. - Ooh, okay. - If you don't pace yourself, right? - Yeah. - You see a lot of people basically just stop because they just can't, because you just feel like you're so burnt out, because it's not like a normal job where you're like, you know, you can deliver, but then you can go on vacation for like a month and you can, whatever, you can take six months off and there's still a job. - Yeah. - But here it's like the pace of chasing the algorithm. I feel like I, you know, watch a lot of creators and I just, it feels like they're just chasing the algorithm. But I want you to stay authentic to yourself. Because that's what makes you special. - Yeah. - And you see these creators are like, oh, you have this viral hit, so you just keep doing that one thing. - Yeah. - But then you forget why people will follow you in the first place, you know? - It's harder to remember. It's hard because then I think the brands and the companies and the agencies are like, well, your numbers are just not high enough. And I'm like, so, your numbers are incredible. What are you talking about? - Thank you. - And I told my, my kids, so we went to an escape room last night that I told them we were coming here today. They're like, oh, she's in our feet all the time. You know her? - What? - They told us they didn't know that we know each other. - They were like, she's the one with a baby box toy, right? And then they were like, she's the one who's hiding. You gotta find out with the gender. And I was like, she hasn't revealed it. I'm not gonna ask her. So anyways, I think it's one of those things where even my kids are your fans, even though they're like a generation below. But they, you know, I think that really like, your authentic voice is the most important thing and not chasing the just the numbers 'cause it's easy to chase the numbers. - It's so easy. - And it's like chasing the promo, right? - Yes, it's like changing the promo. But then it's like, but if it's not a good fit with your brand, if it's not a good fit with your voice, like don't chase that because it's too easy to take the short term, but then lose track of the long term. - You gotta think long term. Before we wrap, for better or for worse, we must conduct what is called a performance review. - Okay, let's do it. - You are no stranger to this. Legally it does not affect your compensation title or follower account, but it might affect your aura, which is really important in 2026. So I'm just gonna ask you about the fire question. - Okay, let's just give quick answers. You ready, Deb? - Yes, let's do it. - Number one, would you rather be right or be promoted? - Ooh. - Right. - Would you be down to make $2 million, but you'd have to be a course person? - Actually, I would totally teach a class in. - Yeah, no, Deb would. - 'Cause I would actually just do that, just for fun. Not for $2 million, but just for fun. - Like you would do it, you would do a propono. - Would you rather ship something mid or not ship at all? - I would ship something mid because you can always iterate. - That is the debu answer. Should filming, a day in the life working in tech be banned or permitted in the office? - I think it should be permitted and why not? - Yo, Facebook had really strict policies on that. - I know, I know. - Really strict people have fired. Are you living with main character energy right now or are you in your NPC era? - Ooh. - A little of the, oh, oh, oh, how's that? - Yes, well, Sue, I feel like, you know, starting a company, you have to feel like, you have to make your character come into that energy, yeah. But at the same time, you know, it's so great to see my kids thriving and say it was a mom. I feel like I'm in the NPC era in my own life, with my kids. - Yeah, they're, like, you're in the NPC. - Yes, I'm the NPC. - Actually, wonton is the main character. - That's right, meetings before 9 a.m. Human rights violation or personal problem. - Ooh, I hate meetings for 9 a.m. - Oh, I am not, I am a night person, not a morning person at all. - Shut up. - Yeah. - No, that you're lying. - I am absolutely not a morning person. Like, when I have a 9 a.m. meeting, I like roll out of bed at like 840. - Oh my God. No way, aren't you the type of person that would wake up and send emails back at 7 a.m.? - No, I would be the person who answered the email at 2 a.m. - You're the first corporate person. - What? - To say that. Everyone has said that's a personal problem. I'm taking my 8 a.m.? - Yeah. - I was like, I hate that. I wouldn't you'll never see me before that. - I hate to speak for 9 a.m. - Wow. - But the other thing is I spent my entire career working with engineers. And I remember we did our all hands at 9 30, and they were like, you know, that's like a human rights violation. - They would not calm. - So then I had to move it to 10, but then we had a team on, so at one point, we had a team like in the UK or something working with us, and they were just like, you know, at 10 a.m., one time, it's like 6 p.m. here, and I was like, oh my gosh. So you can't make everybody happy. - You can't. - Out of 100% for a promotion, what percentage is skill, and what percentage is visibility? - Ooh. - I would say skill is a floor, 70% visibility. - Ooh. - Boy, what does floor mean? - Like, you can't be like-- - Oh, you can't be on skills. - Oh, you can't be on skills. - You can't be on skills. - But so much is visibility. - Yeah. - I've seen so many people with the skills who have no visibility, never get promoted. - Got it. - That's a lot of sense. - Should working while pregnant be illegal? (laughs) - For me, it was so bad. I was telling you I had sciatica and SPD. It was so bad. - So why are we working? - I just don't know how Fubi's generations, like people who worked on farms, people who like had to, you know, work in textile mills. How did they even survive? - I don't know. I don't know. I mean, we have cushy tech jobs, and like, you know, you're sitting on your butt, and it's still impossible. - I mean, my butt, yeah. - You are phenomenal. - I gotta give you a greatly exceeds expectation. Everyone, I feel like I've learned so much and I hit my heartstrings in ways I haven't felt in a while. Deb, where can people find you? - So I write a substack. So devloo.substack, if you want to go there, you can subscribe. I just write about the world, tech, careers, everything. I'm on LinkedIn and Instagram, so follow me. - Should they message you on LinkedIn, or Instagram, or LinkedIn? - Mostly LinkedIn, and I know you have open-door policy, but you don't say yes to everyone, and you don't respond to everyone. So I try to respond to as much as I can, so even if I can't make a call, I can at least like, if you ask me a question, I'll try to answer. What increases their chances of being responded to? Well, if somebody like, for example, introduced me, so this is the connection. One connection? One connection? Yes. But the other thing is like having a very specific question, 'cause somebody might be like, "Let's just hang out." I was like, "Well, I'm happy to help you with a specific thing that it's very hard to just people are like, "Hey, can we hang out, Deb?" And you're like, "I don't know. Who you are?" But I mean, like, for example, if it's somebody in products, I do like product dinners, so maybe I can fight you to something, you know, stuff like that. So find a way to like, always find commonality when you're trying to get a connection. Okay, got it. And would you, Deb, do you ever be down to come back on a future episode of Office Drama? Yes, absolutely. What chapter of life would you want to come back after and talk about next? Ooh. Actually, I want to wait till you're pregnant with your second, because that will be my second. You mean my second? Yeah, this one, but the second-- I'm not sure this one. Because life change is so much more. Once you've seen the babyhood and you're into toddlerhood, your life will change all over again. I'm terrified. I know. Is it some warning? It's some warning. Well, it's a blessing. Okay. Well, he didn't do that. There was a book called, like, "All is joy, none of the happiness or something like that." It's like a sweat. There's a lot of meaning in being a parent. I love every single day of it, but there are many days where you're just pulling your hair out too. So I will come back. I will come back. But I'll come back. Okay. I'll talk more about it then. I'll hit you up. I'll call you. Yes. Thank you for being here. Thank you, Dad. Shout out to our drama llamas on The Patreon. I want to give you a little sneak peek on what I've been posting there. We usually have about one bonus Patreon video per Office Drama episode, so last week we posted the episode with Ellie, and we have this private conversation where I share my horrific experience that I had with a male co-worker, who absolutely blew up on me at work. One day is one of those like ego-too-big experiences, and me as an Asian woman and product manager. I just kind of took it, and it was awful. We also talked about what it was like working at TikTok and Byte Dance, which is a Chinese company, and we shared our honest thoughts on AI/AI prototyping, and we have differing opinions, so that's interesting. This video is a mini vlog on when we release that pipe and hot tea episode with Megan Liu on her experience attending that one open AI band trip, and this kind of just showed my nerves throughout the day. I just wanted to document how I was feeling, you know, like you never get to see the hosts and the guests engage with each other or what they were thinking and feeling before going into a shoot, and so I wanted to bring that element to Patreon. And this one, oh man, so a couple weeks ago, or maybe a month ago, I was shot at the Patreon Office in San Francisco. I usually leave my equipment there, but I got locked out of the equipment room where all my gear was stored, and we had to set up for filming for the next day, like, first thing in the morning, but we figured it out, we survived, it was just really rough, so yeah, that's the Patreon. If you like what you've been seeing on Office Drama, feel free to check us out at patreon.com/office drama, because, well, you see, podcasts are not profitable for perhaps many, many years. Now, onto my thoughts about today's episode. I walked out of this chat with Deb Blue on Cloud 9, I mean, I loved it. It was just such a good energy match. I love Deb, she exudes joy, positivity, but she's also super competent. She has an opinion and piece of advice and wisdom for every single question and problem that I have. Like, she's just so on it, she's so fast, and I know you guys see the edited version, but a lot of people and guests actually don't have immediate answers. They take a really long time to get there, and we do cut that time out, but when it comes to Deb, she just had one immediately. I think it really comes down to Deb's nature of being a very introspective person. She proactively practices that by writing her newsletter, doing mentorship, going on calls and just being a leader who cares about how other people are doing. I know there's a lot of growth I need to go through in my journey as I attempt to build my career from creator to media to whatever is next. I'm going to do a little recap of the takeaways, because that helps me and hopefully helps you. But her five themes were, number one, define success before the world defines it for you. Number two is learn the invisible rules of power and influence. This was a conversation about knowing your playing field and knowing about the invisible tax before a woman entering any room. Number three is how to build a leadership style where you can still have high standards, but not be unbearable and like traumatize others and put people down. And number four is when to persist pivot or change. And lesson number five is when Deb says, "Solve for joy and the rest will come." Ambition without joy becomes brittle, so we got to optimize for it, like you really can't beat someone who's having fun. It was definitely one of my favorite episodes by far. I mean, we've had a lot of bankers on Office Drama, but I was not joking when I said Deb was on the top of my list. I just knew that this was a type of conversation that Office Drama is for that I couldn't quite do with my previous podcast, Jummo. So I hope you've enjoyed it. I want to hear what is the one thing you took away from this episode I'd love to know, drop it below, and I shall see you next time. Bye!

Podcast Summary

Key Points:

  1. Facebook Marketplace’s first launch faced a disastrous day due to a critical bug, with a New York Times headline mocking its chaos, highlighting the challenges of launching new commerce platforms.
  2. Success often takes time—Marketplace took over four years to become widely adopted, proving that meaningful products grow slowly and require sustained belief and patience.
  3. The author emphasizes that true leadership involves shifting from aggressive, self-centered approaches to one rooted in trust, empathy, and supporting others to grow—learning through collaboration, not control.
  4. She advocates for “repotting” in careers
  5. A key insight is that persistence without progress is ineffective; people must evaluate whether to persist, pivot, or quit when conditions are toxic or unworkable.
  6. The author shares personal experiences of overcoming self-doubt and professional setbacks, including her transition from product roles to leadership and co-founding creative ventures.
  7. She champions authenticity over performance in personal branding, noting that real connection and shared vulnerability build stronger influence than artificial visibility.
  8. Women in tech face unconscious bias and structural barriers, but real progress comes from recognizing personal privilege, building resilience, and creating supportive networks.

Summary:

Deb, a tech leader and co-founder of Maya Road, shares insights on building a successful career in a competitive environment. She reflects on the early struggles of launching Facebook Marketplace—its chaotic first launch and long, slow path to success—emphasizing that true growth takes time and trust. Her career journey illustrates a shift from aggressive, results-driven work to a more nurturing, supportive leadership style, where she learned to lead through collaboration, not control.

She highlights the importance of self-awareness, advocating for women to recognize their unique challenges, including unconscious bias and lack of role models. Deb stresses that career success isn’t about relentless persistence, but about knowing when to pivot, change environments, or simply quit if conditions are toxic. She encourages authenticity in personal branding and underscores the need for women to build supportive networks rather than compete.

Central to her philosophy is the idea of "repotting"—reassessing one’s path, team, or role when the current environment is stifling. She also emphasizes financial preparedness and escape velocity, urging professionals to build emergency funds and explore side interests to stay adaptable. Ultimately, Deb promotes a mindset rooted in iteration, resilience, and self-compassion, drawing from personal experiences to show that growth comes not from perfection, but from learning through failure and continuous evolution.

FAQs

The first launch day of Facebook Marketplace in October 2016 was a failure. The New York Times headline read 'Drugs, guns, and baby hedgehogs,' highlighting issues like a bug that allowed users to post inappropriate content. Despite the poor start, the platform eventually became successful and is now used by a billion people globally.

After the launch failure, the team persisted, focusing on fixing technical bugs and improving the user experience. The product was built with a long-term vision for local commerce, and over time, it gained trust and adoption, eventually becoming a major success.

Persistence isn't the same as progress. You must regularly assess whether you're making real progress or just pushing through challenges. Sometimes, changing the environment, team, or goal is more effective than continuing in the same direction.

Early in my career, I was highly competitive and impatient, often working alone and expecting perfection. Through experience, especially managing others, I learned that effective leadership involves patience, coaching, and helping people grow through small, manageable steps.

A toxic or unproductive environment can hinder growth. Changing teams, managers, or products can be more effective than trying to fix everything from within. It's often better to grow in a new environment than to struggle in one that doesn't support your potential.

When facing a difficult situation, consider quitting or pivoting if you're in the wrong role or environment. This requires self-awareness and a plan—like repotting a plant—where you grow in better conditions, not just through effort, but through change.

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