Startup Journeys with Ei-Nyung (Podcast & Transcript)

“[We were trying] to make good decisions while trusting the people that we hired, because that was really fundamental to us. If you hire people that you think you can trust, then actually trust them and see how it goes, as opposed to micromanaging.” - Ei-Nyung Choi

Ei-Nyung Choi is an engineering leader, fractional CTO, technical advisor, and speaker. A full-stack engineer with more than 20 years of experience spanning mobile, web, and gaming, Ei-Nyung is passionate about mentoring founders and women in tech.

In this episode, we discuss:

• The importance of being willing to learn and make mistakes

• Slowing down to help those behind you vs running at full speed

• The advice Ei-Nyung gives every startup founder

• What to consider when raising a seed round 
  

Transcript has been edited for clarity.

Karen Ko: Hey there. Welcome to Engineer Your Career, a podcast brought to you by WEST, a learning community empowering women technologists through mentorship. Join us as we hear from inspiring women tech leaders who are challenging stereotypes and paving the way for future generations. We hope their career journeys inspire you with new ideas to engineer your career.

Let's get started.

Heidi Williams: Hello, and welcome to Engineer Your Career. I am super excited to be here today with Ei-Nyung Choi. She is a startup advisor and a leadership coach. She's also been a fractional CTO and has a fascinating story of her journey in tech over the last little while. So super excited to have you here.

Welcome, Ei-Nyung.

Ei-Nyung Choi: Oh, thank you so much. What a wonderful welcome. We met a couple of years ago, and every time I talk to you, it's been so amazing. I love your dedication to the mission. Yeah, very happy to be here.

Heidi: Yeah, thank you. Thank you. Yeah, I love that we're connected and that we've had many opportunities to do things together.

So, appreciate you supporting WEST along the way. It's been really awesome. Well, I would love to start, just for folks who may not understand all of the things I said about what you do. Do you wanna tell us a little bit more about what is it that you do right now?

Ei-Nyung: Oh, so the thing I lead with sometimes that people kind of like is I'm semi-retired, and the only thing that it means is that I can take on only the work I want right now, and I'm so incredibly lucky. I recognize that that is a very few people, and I'm in a very privileged position, but startup advising is something I really love. I've been in a lot of startups, so what I like to do is, I connect with a lot of young or first-time startup founders, and I coach them on a lot of things.

At first, it probably starts with product feedback or hiring questions or reviewing their pitch deck for VCs, right? But it ends up really being a lot of, no matter what the product is, no matter who the people are, it ends up being a lot of similar themes, which is like loss of motivation or like feeling dejected, feeling burnt out, or people issues.

So I think startup advising is very similar to the other thing I do, which is leadership coaching, because all those things I just mentioned, they all experience that. And by leadership, I mean usually tech lead managers or first-time engineering managers or first-time engineering directors, and anything in between.

Usually, with people who have just changed roles into a higher level of leadership because they were wonderful at the lower level, and then they switch, and they're so lost.

Heidi: Yeah. That's awesome. I love that. And I totally resonate with what you're saying in terms of the startup experience, and I think both of them have a similarity in that you're doing something new that you've never done before and you go in with a ton of confidence and then you end up in that sort of like bit of disillusionment that happens like, "Oh my gosh, am I actually qualified and ready and can I do all the things and do I have all the answers?"

And so I can see how starting a startup or becoming a new leader would have a similar moment where you're faced with the realities and maybe a little bit of overwhelm, in terms of all the things that you'd have to do. So that's awesome. What a cool set of things to be doing. So thank you for sharing that.

Maybe wanted to start and back up a little bit to like, where did it all start for you? How did you first get into the industry or into software and programming?

Ei-Nyung: Okay, so, I have been so lucky because it's been luck after luck after luck for me, timing-wise. I graduated from MIT with a mechanical engineering degree in 1998.

1998. It was such a different world. There was almost no internet, but jobs were falling from trees if you wanted to get an internet job. It was just really incredible. I actually only had a little bit of HTML knowledge. I was like writing a little homepage, you know, for myself and with, I don't know if anyone's old here, but like rotating fireballs as bullet points and a visitor counter at the bottom.

So I was making those things, and that was, luckily, enough experience to get hired at the Sloan School, which is MIT's business school, to help work one of the department's websites. And the funny thing is that that job was available because so many actual computer science students, they wanted the really cool technical work studies, and working at the business school, doing some website was not their thing. So it was beneath them, basically.

But no job was beneath me. I just needed a job. So I did that as a summer job for a couple of years. When 1998 rolled around, I applied for a job that I saw on Craigslist if—

Heidi: Love that.

Ei-Nyung: —Anyone's familiar, and I responded to them, and then they called me on one phone call, and then they flew me out to interview.

I interviewed with maybe five people over maybe three hours, and then two hours later, they called me and faxed me an offer for employment.

Heidi: I love that. I love that. So many of the things you said just took me back in time to 1998, and I actually, when you were saying about the rotating fireballs and stuff like that, I remember the early days working on Dreamweaver, and we would build sites, and I would use the JavaScript timeline, and I made a site that had an image of a skier.

Like skiing down across the page, and it was so janky, but I was like, oh, I love that you can animate stuff with JavaScript, and, yeah, fun, fun times, back then.

Ei-Nyung: It was fun times, and sometimes I like to tell people I started working on web technologies before the table tag was in common use, or before, actually, JavaScript was in the browser, I think.

Heidi: I love that.

Ei-Nyung: I think it was only there experimentally, but—

Heidi: Yep. Yep.

Ei-Nyung: But the other thing about luck and getting into the industry is that the two technical people, aside from my future boss, that interviewed me, one was a bio PhD candidate dropout.

Heidi: Oh, wow.

Ei-Nyung: And the other one was an 18-year-old who was just like hobby tinkering on code and was going to college part-time.

Maybe he was 19. Yeah. And so they interviewed me, and I guess they didn't care that I had like, not a real computer science background. They just gave me a questionnaire and talked to me a little bit, and they're like, “I guess.”

Heidi: Yeah.

Ei-Nyung: I'm, yeah...

Heidi: I love that. I love that. Well, clearly, you impressed them by being smart and capable and interested in learning.

And those years were wild. I mean, we were sort of talking about how 1998 was really the huge dotcom boom, and then only just a couple years later, the big bust in '99 and 2000, and you mentioned that you were working on some really fascinating early technology. Tell us a little bit about what that was. I actually remember the technology that you worked on, but tell us a little bit about what that was like to be in that moment of—

Ei-Nyung: There are actually two different ones that are like big markers, which is the first startup I was at, MP3s hadn't happened yet.

Heidi: Hmm.

Ei-Nyung: They hadn't happened yet, but they happened while I was at that startup, and our startup was like a web interface to Usenet, which has a lot of binary files that are all over the place. But the MP3 standard came out. People started to create MP3 files and then.... And now I understand they were pirating.

I didn't know, as a fresh young grad, what was happening, but they were pirating a lot of software. There was a lot of not-safe-for-work stuff that was being put out there, but I had no idea. Anyway, I was just working on this Usenet website thing, and we were, I think, the first to be.... Back then, you had to download little bits of files, and then you had to put them together, and then you had to run a script, and then run it.

But we were able to do it such that you could search for a random file on all of Usenet and then get all the files, have them stitched together on their own, and you just download the MP3, and you can just play it right there. And to celebrate that, we all got the first Rio MP3 players that only had like, I don't know. Was it three megabytes? Something like that. It was very small.

Heidi: That's amazing.

Ei-Nyung: So that was one, and the other one was that I got to get on in on the iPhone and Android and webOS, the Palm phone. Pretty much as they were born. Because before that, I was working on pre-smartphone technology, like the Nokia phones and the... I don't know, like the old like Windows phones, Windows CE phones. Ooh, they were terrible. So I was working on enterprise software that was a software replacement—or competitor to Blackberry, which.... Do you remember Blackberry? Yeah, so....

Heidi: For sure, for sure. There was a moment where we [crosstalk] we were sort of hoping Blackberry would be an interesting third competitor to Android and iOS, but, unfortunately, that didn't happen.

Ei-Nyung: Yeah. So, for people who don't know what Blackberry is, it is a small, little handheld device that you can carry around that only does email. Just email. That's it.

Heidi: Yep. Yep.

Ei-Nyung: Yeah, so we were trying to get email on lots of other kinds of phones that you couldn't use email on, which sounds ridiculous now, sorry. [laughs]

But the really fun part of it was like I said, I started in web technology, but there, I was working on firmware and also on embedded software. So I only did a little bit of firmware stuff, so that scared me off. But I did a lot of the embedded software that would ship, and be flashed onto the ROMs, and for the Treo.

Heidi: Yeah.

Ei-Nyung: Treo 600 was my favorite model, I think. And so I went from HTML, and at the time, Perl... Perl is like what PHP might be now, to learning C++ and C, and I learned Java on the other job, as well. So I just went from Perl straight to C++ and putting them onto tiny devices with limited memory, it's like, "Wow. Memory management's super hard, huh?"

Heidi: Yeah. Yeah. We live in a world of abundance now, where it feels like you almost don't have to worry about that stuff. It's not totally true, but...

Ei-Nyung: Yeah, I had that background, and there's a long meandering story, I won't tell, but a different startup, later, that I was in, wanted to start developing for mobile.

Heidi: Mm-hmm.

Ei-Nyung: While, like, Android phones were not out yet, we were on the G1 prototype, and we were on the SDK that started with a zero, beta SDKs. And so, because I was the only person that my boss knew that had Java experience and mobile experience. So rare. I was like, “I could do the Android work.”

Heidi: I love that.

Ei-Nyung: It was super hard. So I was developing the Android version of what the team was developing, and we were developing for the iPhone, the Palm phone, and also for Flash. That's right. I also owned the Flash work.

Heidi: Yay, Flash.

Ei-Nyung: That was a fun job, too, because every time I left a job, it was basically like, hey, learn a new language and platform at the same time.

Heidi: Yeah. Did you have tricks for, I mean, you must have gotten really good at learning, but did you have tricks for, like... what resources did you have or how did you go about learning all of this stuff?

Ei-Nyung: Okay. I have to tell you this one story. The trick is that I really read a lot of other people's code, and I would look at other people's commits, and back then, we were just committing to the trunk and manually pushing. It was like just main—There was no branch [inaudible] just pushed main to production. But I have to tell you this story because it's super embarrassing, but people love it. So I was about a year and a half into work, and I was still very in the stages of learning anything at all.

And I was working with someone who was incredibly senior, very experienced. He had worked at a bunch of, like, he worked at Apple when it was way smaller, and he worked at a whole bunch of other places, and he is probably in his forties already now. He was just like 22 or something. His name was George, and this is important in the story because he and I were on a project together, and he was so nice.

He taught me so much stuff. I saw so much code patterns and design patterns that I wasn't exposed to before. I was like, oh, this is what posting a message means. This is what an event handler is. So I learned all these things while working with him, but I also saw that some of his variables, not his [inaudible], but just his variables had a G in the front, a little G.

And followed by a capital letter, you know, like timer whatever, status timer or something. And I was like, "G, he must be notating for George. G for George, so that he knows that he wrote that code." So guess what Ei-Nyung did. Ei-Nyung made a bunch of variables with it, starting with a E. And the G was just for global variables.

Heidi: Oh, no.

Ei-Nyung: And also, if you followed any convention, the E would be for enumerations, which doesn't make any sense. But anyway, so, but I had been checking in this code for months at that point, months of like variables—And there were global variables that started with an E—

Heidi: Oh my gosh.

Ei-Nyung: Next to George's variables that started with a G.

And I think he actually didn't notice. And so I admitted it, and I changed all the variables. Slowly, so that I didn't mess up, but, that was a shockingly embarrassing mistake.

Heidi: That's so great. That's so great. It is funny that you… I feel like I have embarrassing examples of software practices I had way back then as well, and it was, yeah, you're right.

I feel like you have a mentor, you have someone you're following, and sometimes you ask why, and sometimes you just follow the pattern and whatnot. I love that.

Well, amazing that you were working on... like all of that was sort of innovating so rapidly and changing so rapidly. I think it's really incredible.

It sounded like, at some point, you transitioned to founding your own startup with your husband. What was that like?

Ei-Nyung: It took a lot of preparation.

Heidi: Yeah?

Ei-Nyung: So I actually grew up my entire life being like, I do not wanna be a business owner. I do not wanna run my own company. I do not wanna be anyone's boss. And the reason is because... so I'm an immigrant and I am around a lot of immigrant families and their parents, and so many of the parents are trying to do their own thing.

They own their own restaurant or run their own dry cleaners. It's very like, oh yeah, it's a stereotypical what are the Asians doing, those are my friends. Right? And I saw how hard they struggled. I saw that. And like my dad, he was a carpenter's contractor, which again, is your own business, right? And I saw that, like, if the business didn't do well, you could lose your house.

Heidi: Yeah.

Ei-Nyung: Right. You could, like, not have a place to live. Whereas if I work for someone else and they don't do well, I always have the option of going somewhere else.

Heidi: Yeah.

Ei-Nyung: And I had heard this myth that they have benefits at companies, and I was like, "Oh my God, I could have healthcare for the first time in my life."

'Cause we didn't have health insurance. I think I literally went to the doctor zero times until we had to apply for college.

Heidi: Wow.

Ei-Nyung: Zero times for dentist and a doctor because they needed medical records. So yeah, I never wanted to start my own business. It just seemed like a bad idea. And plus, we had two small kids at the time.

I think they were three and six, and that's little, and need a lot of work. And I love them. Like my heart just changed when I had them. Sorry, I'm getting emotional.

Heidi: No, I love that.

Ei-Nyung: But I was like, okay, so we can't do anything to endanger their future. Like, we cannot dig into anyone's education fund.

We cannot dig into our retirement funds. We cannot do any of that. We can only do this if we think we have sufficient buffer that we can actually lose this specific chunk of money and we could survive. Without remortgaging the house, right? So it's like we're only gonna do it if we can do it. Not if we have— like so many people I know went on, took out like 20 credit cards, right?

And put their startup spendings on that. And I was like, I can't. I also had really bad credit because I had to pay rent with my credit card when I was in college 'cause I was so broke. And I couldn't pay it, so I had really bad credit, and it took me years to fix it. So I'm scared of credit card debt, and so I was like, I can't do that.

And I've always just wanted financial security. There were so many times when we were not secure when I was growing up, and I was like, startup founding sounds like the very opposite of that.

Heidi: I was just gonna say, that's what I would think.

Ei-Nyung: Yeah, because it's also like specifically for a startup, it's not even just like starting a new business.

You're starting a new business where that product doesn't exist yet. That's the whole point, right? So you don't know if it's gonna work. It's not like opening another, I don't know, version of a whatever. Right?

Heidi: Yeah, yeah.

Ei-Nyung: Well, the thing was that we had left the prior company under stressful terms.

We weren't happy when we left. We voluntarily left, but we weren't happy.

Heidi: Mm-hmm.

Ei-Nyung: And that was a startup that my husband was a—he was a co-founder in that startup.

Heidi: Mm-hmm.

Ei-Nyung: I didn't meet him there. He and his co-founder had sort of started this little startup under the umbrella of one of my former bosses.

Actually, he was my present boss at the time. It's complicated, but basically, my husband got funded for a startup at the startup I was working at, for a different thing.

Heidi: Okay. Yeah.

Ei-Nyung: And at some point after having my first kid, I was like, I can't commute from Oakland to Redwood City all the time. And neither can my husband, but my husband is getting to work from home three times a week because he's at that other startup with a lot of people in Oakland.

Heidi: Yeah.

Ei-Nyung: And coming back, my project had been shut down because it was understaffed. And it wasn't doing well. And I was like, uhoh, what am I gonna do? And that's the time when I was like, I know Java. I know mobile devices. Put me on the Android part of that project. There's no one that can do Android there.

Heidi: Yeah.

Ei-Nyung: And so I got put on that project. I didn't report to my husband; I reported to the technical co-founder. We always kept separate streams. Like we didn't go to lunch together. We didn't say hello. We didn't exchange looks at work.

Heidi: Wow.

Ei-Nyung: People knew we were married, but we did our best to just treat each other like coworkers.

Heidi: Mm-hmm. Mm-hmm.

Ei-Nyung: I didn't want any special treatment. He didn't want there to be any, like… honestly, the shadow would be on me, right? Not him. Right?

Heidi: Mm-hmm.

Ei-Nyung: And so he would always be like, “Oh, Ei-Nyung was the one that worked here first, and then we got the startup,” blah, blah, blah. So he was very supportive in that way, too.

But we worked together for, I don't know, four or five years at that company…

Heidi: Mm-hmm.

Ei-Nyung: …That he was running. And I was the most senior engineer there, and I was shocked at how—like, I always loved him, right? And I always respected him and thought he was a great person and blah, blah, blah. But the level of professional respect I gained for him at work because of the way everyone else felt about him and because I could see how he like directed the team and made difficult decisions.

I was like, oh wow, I didn't know you were this good. Like everyone loves you. Everyone says you're the best boss they've ever had. Like, literally everyone.

Heidi: I love that.

Ei-Nyung: And he found the just as deep professional respect for me. He knew I did programming, but what is that, right?

Heidi: Yeah.

Ei-Nyung: Like, he was not sure what I did at my desk or with people, what kind of projects I worked on.

Even though we talk about it, it's still kind of a mystery. But since I was working on projects that he was fully aware of, he could see how much of a leader I was, how much of a big hand I had in engineering, how I hired and onboarded everybody, basically. And everyone loved me.

Heidi: That's awesome. Awesome.

Ei-Nyung: There were a couple that didn't, but that's fine.

Heidi: I love that. I feel like not a lot of married couples actually get to see each other in a professional setting, and sometimes, being together in a professional setting is terrible.

Ei-Nyung: Yeah.

Heidi: That sounds like it was an amazing experience for both of you. 'Cause I was gonna ask, I feel like not every couple would be good co-founders.

And so I guess it sounds like you at least knew ahead of time that you could be good co-founders together.

Ei-Nyung: But the downside is that like... Here I am sleeping, right? And my husband gets a call being like, the servers are down, right? And next to him is the most senior engineer. So he is like, can you restart the servers? [inaudible]

Heidi: Did he page you or just rollover and say hi?

Ei-Nyung: Yeah. He'd be like, [whispers] “Hey, can you, can you wake up?”

Heidi: Yeah. Yeah.

Ei-Nyung: I was like, oh, this part sucks. Because we were new parents at the time. Like our kid was like half a year old.

Heidi: Yeah. Oh my gosh. That's really funny.

Ei-Nyung: So he felt really bad, but he was like, I don't know what to do.

Heidi: Yeah.

Ei-Nyung: Yeah. So. I mean, my husband and I only decided that we could be co-founders.... 'Cause we talked a lot about it. We weren't like, “Hey, let's do this thing.” We were absolutely not like, “Hey, let's do this thing.” We were like, well, I wanna do something and you wanna do something. We have different complementary skills.

We know the other person's work ethic and how good they are.

Heidi: Yep.

Ei-Nyung: But it was still this long process of like, that sounds like a mistake because... but the only thing that made it correct was that yeah, we checked our finances, we decided on a specific budget that we were never gonna go past.

Heidi: Mm.

Ei-Nyung: Like we would move it into a different bank account, right?

Heidi: Yep.

Ei-Nyung: To do the startup. We also went to sort of counseling to make sure that we were working out personal stuff and professional stuff, and that they were not intermingling and that we were not bringing stress to the other parts.

Heidi: So smart.

Ei-Nyung: And we would still never have done it if we hadn't worked together on the same projects.

Not in a hierarchy, but together. Like we were in products that made this decisions. Right? Like on the same thing.

Heidi: Yeah.

Ei-Nyung: So because we knew that we could work well together and that we could also work well together in a situation where other people didn't seem bothered by it.... Maybe they were, right? But they didn't seem bothered by it.

We were able to maintain that professional wall. We're like, we could try this.

Heidi: That's cool.

Ei-Nyung: We tried it. But, you know, every single time I meet a startup founder, I'm like, tell me about your co-founder. And they'll be like, "Oh, this is a friend I've known for a long time.” Like, this is a friend? Did you ever work with them?

Heidi: Mm-hmm.

Ei-Nyung: They're like, “Well, we worked on this project.” Was it a real job? And I push and push and push. Or they're thinking about bringing someone on board that they just met. And I'm like, no, do not make anyone your co-founder if you haven't worked with them before, when you're a startup. Not when you're big.

Heidi: Yeah.

Ei-Nyung: If you haven't worked with them before, just because you get along really well as friends. It is actually almost a guarantee that you will not be friends anymore, I feel like.

Heidi: Yeah.

Ei-Nyung: From the number of startups I've seen, so I always ask.

Heidi: That's amazing insight.

Ei-Nyung: I always say you can become friends after you've worked together, but don't work together after you are just friends.

Heidi: Yeah. Yeah, I can imagine that. I really do feel like that's the extreme version, you know, being with a partner and co-founding something. And it sounds like you took a lot of really key steps that you would actually recommend for others as well to sort of… I mean, is that something else you talk about in terms of having folks figure out their budget of what they're willing to put into it before they make a decision about continuing or seeking more money, as well as the sort of counseling piece of it in terms of building that founder relationship.

Ei-Nyung: Yeah, I think that, like any other large financial decision, you really need to have not just thought the idea through…. Like people think about buying a house, right?

Heidi: Yeah.

Ei-Nyung: And what often happens is they're like, "This is my budget.” They go see a house, they're like, “Well, this isn't it.” They go see another house that's a little higher than their budget, right? Oh, this is a little nicer. And then you start to see things that are much higher, and you go see them, and you fall in love with them.

You know, and a different kind of thing happens with startups, which is that, I'm running out of money, but we're so close, we're so close. If we just had another month, another two months, we can do it. And this credit card offer with zero APR for the first year, I'm not even joking, this is such a common scenario.

Will pay for that month or two. And I'm like, oh no, and it always seems so close. Because almost no one gets zero users. They'll get one user or two users. They'll get, maybe, someone that looks like they might sign up for money. But the thing is that in order to not run out of runway, you need to either raise money.

Heidi: Mm-hmm.

Ei-Nyung: Or you need to become revenue positive.

Heidi: Yeah.

Ei-Nyung: You can't become revenue positive of one, like, consumer in a B2C business or something like that, right?

Heidi: Yeah. Yeah.

Ei-Nyung: So you need scale. So we actually also predicted the scale of like, hey, if we're doing this kind of thing and the average pricing is blah, blah, blah, what volume do we need for us to become sustainable if we have two, sometimes two and a half employees, right?

So we ended up having two employees, and we were like, how much do we need to raise? What we ended up doing was, we just raised an angel round with friends and family.

Heidi: Mm-hmm.

Ei-Nyung: But, actually, no family, just friends.

Heidi: Yeah.

Ei-Nyung: Also, I have another tip for startups, startup people. When you're raising money from friends that believe in you, imagine you lost all of it, like all of it, next week, like it's all gone, right?

And you have to meet your friend for dinner. Is that friend gonna be able to look you in the eyes? Are you gonna be able to look them in the eyes?

Heidi: Mmmm.

Ei-Nyung: That's the amount of money that you can take from them where you both feel comfortable with you losing it all. There's no return, zero return. And it even has to be like, my friend trusts me enough that even though it looks like I'm making bad decisions, you know?

Heidi: Yeah.

Ei-Nyung: And I lose the money, that should be okay, and we still have our friendship.

Heidi: Yeah.

Ei-Nyung: So if they wanna give you a lot of money, say, "Is that gonna be true? If I lost all of this, would you be okay?" Right? So don't take it if they wouldn't be okay.

Heidi: Yeah.

Ei-Nyung: And also there are things like, hey, sometimes even when you're in really tight circumstances, you want something nice for yourself.

So you might have a reasonably nice dinner or something, right? And then, and this is based on a true story, right? And they might see that you went to a reasonably nice place on Instagram, and they'll be like, well, they're saying they're running out of runway. How are they going to the thing? And resentment builds.

Heidi: Yeah.

Ei-Nyung: So, it is really tough to take money from family and friends for that reason. So only take money from if you have rich friends, you know... or not rich. They're secure. Very, very secure.

Heidi: Yeah.

Ei-Nyung: And very risk-tolerant.

Heidi: Yeah. Yeah. That's great advice. 'Cause when we had our startup, I was nervous about doing a friends and family round, and we ended up not doing it.

Partly because I feel like I wanted to be securely in the space, both of where, I knew that the investors we were talking to could evaluate what we were doing in a way that they felt comfortable with it, and they're professionals at doing that. And also, it's their business, and risk is built into how they think about everything.

And so we did not do friends and family for ours because I wanted a real professional evaluation of what we were doing and whether they thought that it had legs and could make returns for them.

Ei-Nyung: It's actually really interesting because, in a weird way, that was the opposite of our approach with VCs because we did think about raising—we met a couple of VCs—but my husband and I realized that we don't have.... You know, the unspoken question, sometimes the spoken question, is, how is this gonna make me a billion dollars?

Like, whatever, right? Or how's this gonna become a billion-dollar company? A unicorn.

Heidi: Yeah.

Ei-Nyung: And the fact of the matter is, my husband and I were not trying to become a unicorn. We explicitly did not want to become a large company that is faceless and nameless.

Heidi: Mm-hmm.

Ei-Nyung: And really focused on just the bottom line because that's what we left. You know, the other thing, right?

Heidi: Got it.

Ei-Nyung: Yeah. And we loved it when it was smaller, and like you only had one project at a time, and everyone sort of focused on the mission. You had shared values. And no one was a stranger. We really liked that. And so we talked about it, and we're like, yeah, there would be this thing where we have to pitch it as a potentially billion-dollar business, a billion-dollar market.

Heidi: Mm.

Ei-Nyung: And we have to live with their expectations that that would be the case. But we don't want it. It'd be a total lie. If we pitched that, that'd be a complete lie.

Heidi: Yeah.

Ei-Nyung: And what we really want is what they call a lifestyle business, which I think is, I like the sound of it on one side, but it kind of sounds condescending.

Heidi: It is, yeah. It's pejorative in their minds.

Ei-Nyung: Right? And I'm like...

Heidi: It's a failure.

Ei-Nyung: But if you describe a lifestyle business, It's like, oh, you have a steady business, and it makes enough money to keep running and paying you and all the employees, and you will be able to continue to do that, and doing that for decades.

Heidi: Yeah, it is—

Ei-Nyung: Like, oh my God, that sounds great!

Heidi: It's wild to think that that's not the definition of success, but you're right. Yeah. That's fascinating. Well, how did things end up turning out for your startup?

Heidi: Let's take a quick break to hear from our sponsor.

Karen: Are you ready to take control of your career?

WEST can help. The WEST Career Accelerator is a six-month learning program that combines one-on-one mentorship and group-based career coaching to help women gain clarity, save time, and define success on their own terms. We're here to help you create a path towards the career you'll love. Check out how WEST can help you succeed at joinwest.org.

Heidi: And now back to our discussion.

Ei-Nyung: Short story is we ran out of runway. Totally burned out. Lots of crying.

Heidi: Oh, that's hard. That's hard.

Ei-Nyung: But the longer story is that we worked really hard. We tried to implement a lot of the ideals that we had. We had a weekly check-in that was, yes, it was a standup, but it was also like, Hey, how are you doing?

How's your burnout? You know the whole company. And we would, even though it's very small, we would have one-on-ones with the other employees, always looking to see what we could do better. And we really try to toughen ourselves up for feedback.

Heidi: Mm-hmm.

Ei-Nyung: And things like that, and try to make good decisions while trusting the people that we hired, because that was really fundamental to us.

If you hire people that you think you can trust, then actually trust them and see how it goes, as opposed to micromanaging.

Heidi: Love that.

Ei-Nyung: And we also tried the four-day work week, and it was great, actually.

Heidi: Oh, cool. Oh my gosh.

Ei-Nyung: They are right. It's less stressful because you have things you have to take care of. Everyone has things they have to take care of that's only open on the weekdays.

Heidi: I love that.

Ei-Nyung: And we weren't doing like 10 hours a day, crammed in. We were doing like, hey, we're gonna do a regular workday the other four days, but we're gonna just trust ourselves to really get it done, right? Yeah, there were no slackers in our team, and we also really cared about work-life balance.

Even in the startup that my husband was running, there was zero crunch time, except for—no, there was one crunch time, only, and it was—we were developing games. Games and startups, both are notorious for crunch time, or, you know, just overworking people, but my husband was super dedicated to keeping a work-life balance.

So the office would be out of people by like six, unless someone randomly wanted to stay behind, but he was like, I'm leaving. You know?

Heidi: Yeah, I love that. I love that.

Ei-Nyung: So it was really great. We tried to do all of those things that we had learned. Tried to be the kind of bosses that we sort of saw ourselves being.

Heidi: Yeah.

Ei-Nyung: And we were also trying to make the best decisions for the product, right? Like constantly. And the hard thing that I didn't realize about being a founder is that if you wake up every single day and you do the best work that is humanly possible for you, and then you finish the day and you're like, I did my best, right? And you do that day after day after day. But you still result in failure, or what feels like failure, right?

Heidi: Mm-hmm. Mm-hmm.

Ei-Nyung: Like your business doesn't go anywhere. No one wants to play your thing, right? Then that really shakes your confidence because if you were like, I could question that decision I made two months ago.

I mean, you do question it, but every day you're showing up trying to make the best decision possible and learn the lessons and iterate and do all those things. And I've been in, I don't know, that was the fourth or fifth startup I was at, maybe sixth.

Heidi: Yeah.

Ei-Nyung: Oh, that was the sixth startup, right?

Heidi: Wow.

Ei-Nyung: So I've been on a lot of startups. I know what that life is like from the employee side, right?

Heidi: Mm-hmm. Mm-hmm.

Ei-Nyung: But I think having other people's salaries and their living situation, basically, and their healthcare depend on the decisions you're making. And then every day you see the bank account going down, down, down. And also, we were very open with the bank account.

We would update them every month on how much, like, actual dollars are in the bank account.

Heidi: Yeah.

Ei-Nyung: And how much runway that translated to. And we always said, if it looks like we're running out. Even during work time, we're not gonna be mad if you're looking for a job because your family is the most important.

Your housing, your healthcare is the most important. While you still believe we can do this, like, do this.

Heidi: Yeah.

Ei-Nyung: But if you are like… we're not gonna be personally offended at all. Like you can't be, you shouldn't be. Yeah.

Heidi: Yeah, yeah. That's amazing. I mean, I do think not a lot of startup founders really think about that level of care in terms of, I'm responsible for people's livelihoods here.

And so you owe it to them to be transparent and authentic and honest about where you are while still hoping that they'll keep with you on the mission and the journey, and you'll find a way to sort of turn things around and whatnot. But I do think that there's a… I mean, you are right also about the VC money.

It's easy to think that the VC money is someone else's money, and it's okay to just spend it. Whereas if you feel like you know who it came from more personally, you might take more care with sort of how you spend it, as opposed to feeling like, whatever, we'll just go to the next VC and get more money.

Ei-Nyung: Yeah. Like you can't have that party, I'm sorry, I can buy lunch myself.

Heidi: Yeah, exactly. So, yeah. Well, I'm sorry it didn't work out, but you know, I, I do feel like it's... startup journeys are hard. And it sounded like after that, you took a bit of a break. I'm sure you needed time to sort of decompress and whatnot, but did you think about not coming back after you took a break?

Ei-Nyung: Well, so at that point, we had two kids.

Heidi: Mm. Right.

Ei-Nyung: And they were small, and we were burned out, but because we weren't paying salaries, we could take a little time off.

Heidi: Mm-hmm.

Ei-Nyung: So we both started looking about… actually, I started looking about three months after. No, I think I started looking two months into it closing down, and the assumption was that, I would get a job easier because he's a game designer and studio head, and I am an engineer, a very senior engineer.

It's like, yeah, I'm gonna get that job first because there's much more opportunity for me. And that time was also a good time. In the economy and in the industry. But I would have loved to not have gone back for a long time. Because I was still burned out. And I actually remember, I'm so embarrassed.

They were so nice about it. I actually cried in one of the interviews.

Heidi: Oh.

Ei-Nyung: Because they were asking me about difficult decisions I had to make as a leader. And I was like, talking about startup stuff. And I was like, oh God. And I started, I was like, this is very fresh. I'm sorry. And they were so kind.

They actually gave me an offer at the end.

Heidi: Oh, wow.

Ei-Nyung: Yeah. So they weren't just being like, that's fine. They were like, that is fine. They were so empathetic. Love those people.

Heidi: That's amazing.

Ei-Nyung: But that's not the job I went to, though. But the job I went to was Slack because right before the startup… Actually, right before our startup and serious talks started with my husband, I had made a little file, a little list of companies I might want to go to.

It was like February, 2014. Slack had just come out into public beta or something. I think they were in private beta until the end of the year, and they came out at the beginning of the year. I love Slack. I was like, this is the best thing ever. And we were a game company, and they spawned from a game company, so everything Slack had we needed at the time.

It was incredible. And so I had that on my little short list of companies I would go to. Also, because I had read up on the founders' bios, and I knew about at least the professional side of their backgrounds. And I felt like these are people that seem like they have ethics and values and a mission that I can actually be aligned with.

You're not gonna align perfectly with anyone, but I was like, I wanna go somewhere where I know that they've made good decisions about things. And you know, I think he did, like when, I don't know if people know the Slack story, and I'm not gonna tell it, but he had to do a lot of difficult things because they had to pivot, to become Slack.

And a lot of hard things happened. And I had read all these stories of how that was handled, and I was like, he's the guy. I would work for him. Stewart Butterfield, right? So I had that on my list and then, you know, things went.... We ran out of runway three and a half years later, and then I was applying, and I was like, Slack's still at the top of my list.

I had done the research, so I applied, and I really liked everyone I met. I was like, this is super nice. And their process was a little different, and I was like, oh, I enjoy this. And I went, and I did love it. At first, it was really hard getting used to a bigger company because I was in such small companies.

Heidi: Yeah. How big were they at that point?

Ei-Nyung: I think, I think they had something like, the rumors were that there was something like 400 engineers, but I was in the front-end organization, and there were only 55 because I asked, I was asking around how many front-end engineers are there, and they're like, no one knows.

And I literally went and counted. There were 55, so I was the number 55 engineer at Slack for front-end, only.

Heidi: Front-end. Yeah.

Ei-Nyung: Because they had a lot of different teams.

Heidi: Yeah.

Ei-Nyung: But it felt really small because those teams sort of operated like little communities.

Heidi: Yeah. Yeah.

Ei-Nyung: And it was really supportive. I had never worked with so many women and people of color in engineering.

Heidi: I love that.

Ei-Nyung: And like I was like, oh. I mean, the number's not that good now, and the numbers, it turned out, weren't that good in other departments and other teams, but my manager and my director were incredible.

Heidi: Yeah.

Ei-Nyung: But the thing I always tell people is that when I joined my team, there were more women named Jessica than white men.

Heidi: Oh my gosh.

Ei-Nyung: Can you believe that?

Heidi: That's funny.

Ei-Nyung: In my engineering team, right?

Heidi: That's so awesome. What a statistic.

Ei-Nyung: How? Right?

Heidi: That's awesome. Oh my gosh.

Ei-Nyung: And like, you know, because people talk about the Matts, right? They're like, oh, you work with more white guys named Matt than black women in the company, or something like that.

Heidi: Yeah. Yeah.

Ei-Nyung: And you're like, oh, that's true. Like you count and you're like, oh my God, that's not an exaggeration.

Heidi: Yeah.

Ei-Nyung: 'Cause tech is so... undiverse right now, right? But it was such a wonderful environment, and like it really did, you know, just whole bring your whole self to work, and you don't, you shouldn't bring your whole self to work, right?. But it felt like I could bring as much of myself to work as I wanted.

Heidi: Yeah.

Ei-Nyung: And be totally like, this is fun.

Heidi: That's amazing.

Ei-Nyung: Yeah.

Heidi: That's amazing. It is such a different feeling. I do feel like I had that when I was at Box, I really felt that. And it is amazing when you actually find an environment like that.

It's hard to find, but it is always a real pleasure and a real joy to be able to do that, which is cool.

When you went to Slack, were you... I know you obviously, as a startup, you were a leader in the organization. Were you hired as an individual contributor and as an engineer, or did you get into management while you were there?

Ei-Nyung: So there were manager positions open and individual contributor positions open, and I gave it a lot of thought. 'Cause I was like, even though intellectually I know it's not true. But, going from, you know, and I managed at the job before that. Going from, like, being a leader to an IC again feels like failure. It shouldn't, but it feels like failure.

Heidi: That's hard.

Ei-Nyung: And I was already really low on self-esteem, right? But I was also like, I'm not in any state to manage anybody, be responsible for big decisions. I wanna not have big decisions. I wanna just like do the thing I know I can do, which is write code, ship products, you know?

Heidi: Yeah.

Ei-Nyung: Implement features, right? So I was like, all right, maybe I'll do that again sometime, but I'm just gonna go in as an IC.

Heidi: Yeah.

Ei-Nyung: And actually, I had so much more fun as an IC because, well, one, it did build confidence, but I had more bandwidth, and I impacted a larger part of the organization than I would've as an engineering manager.

Heidi: Mm.

Ei-Nyung: I mean, I befriended a lot of people who were engineering managers and people who had become engineering managers at Slack while we were there. And their team is like three people, right? And they interact with a total of like maybe nine other people, and that's their scope.

But at Slack, I started all sorts of random initiatives, like a brown bag lunch, a tech spec review, a couple of recurrent mentoring programs, and that impacted literally hundreds of people every quarter.

And I'm like, I love this. And no one's saying no because I don't need a budget to just have a meeting, right?

Heidi: I love it. Yeah.

Ei-Nyung: They're like, I'm not hiring people. Whatever, right? I don't need a team. So I had a really good time. And because I was doing random stuff like that, people really liked me, and I was like, oh, it's so nice to be well-liked, you know?

Heidi: That's awesome.

Ei-Nyung: You know what I mean?

Heidi: Well, it's kind of nice that you were able to choose those things as opposed to them being assigned to you as part of your job, and do you feel like maybe as an individual contributor, you had the bandwidth to do that, that maybe as a people manager, you might not have had the bandwidth to do that?

Ei-Nyung: Oh yeah. As a people manager, I definitely would not have, but as an IC, I also shouldn't have, but I was carving out time. I was making time, I was making sure that I was always on. I knew that if I slipped up in my work at all, my actual assigned work, if I looked like I didn't care, if anything looked a little shoddy, that all of that would be gone because those are extra, right? Those are things I'm signing up to do.

So I could not let my work quality slip, and I never did. And I also enjoyed... And this is weird. I didn't get into coding because I enjoy software, but I now really enjoy the process of developing things with people. So I enjoyed it.

Heidi: That's awesome.

Ei-Nyung: So I carved that time, and it's interesting because all of the things I'm saying is glue work, right? And we talk about glue work all the time. Women and people of color always pushed to do glue work, not rewarded for it. And it's free, right?

Heidi: Yeah.

Ei-Nyung: And the interesting thing for me is that there was a time when I really wanted a promotion, and my manager was like, you're not ready.

And I was devastated.

Heidi: Oh.

Ei-Nyung: In Slack, right?

Heidi: Yeah.

Ei-Nyung: I was really upset, and I was upset for a while. My manager was like, are you okay? I'm like, I'm not okay.

Heidi: Oh boy.

Ei-Nyung: She was really great, but. I was like, I could try to work in the specific way they want me to work to get to the next level, or I could do whatever I want and be happy and have the impact I actually wanna have.

And so I was just like, well, they're still giving me raises because I'm doing a great job. Good. I got the money. If they weren't giving me the money, I'd be like, Hmm. But...

Heidi: Right.

Ei-Nyung: Gave me the money. I was getting paid on the, some of the highest parts of the band. 'Cause we had like a little anonymous tracker for people's salaries and stuff.

It's like, oh cool. I'm not getting underpaid. So I chose to do the things I wanted to do, and be like, I'm not gonna hunker down and do these things. I'm not gonna... I think the thing that was upsetting for me is that in order to get promoted to the next level, essentially, you needed to jockey for really plum projects.

Be like, oh, like sniffing out a good project and being like, I want that and grabbing it outta someone's hands or coming up with something that is potentially useless, but sounds really cool. And I was like, I'm not about that. And also, that was from staff to senior staff. And even as a staff, I felt like there were so many people who are more junior that need the opportunity.

I'm like, I've led projects before. I don't need to lead another project. I've led company-wide stuff before. I don't need this. I don't need to prove this to anyone. So I didn't, and instead I was,,, and I would lecture the senior staff and principal engineers too. I'd be like, you guys should be mentoring people.

Heidi: Yeah. Yeah.

Ei-Nyung: And I was just like, Hey, have you considered mentoring someone? I would say it nicer.

Heidi: Yeah. I love that, though.

Ei-Nyung: Like, hey, instead of you taking the project, what if you were the shadow help? And help them figure out what to do.

Heidi: Yeah, that's amazing. There's so much value in that and sort of looking at it as an investment in capacity and figuring out how to deliver more value, and yeah, definitely, I can see that.

I feel like there are, I've heard that a lot of companies that it's more about whether something is sort of innovative and presentation-worthy than actually impactful or valuable to the organization or to customers or anything like that. It always bums me out that the incentives are not aligned to actually kind of create more value for the organization, or to help people learn and grow.

You did mention that there was a pivotal moment at Slack where you did end up getting promoted at the end of it.

Ei-Nyung: I was like, there's a happy ending.

Heidi: If you weren't sort of seeking out projects, how did you end up assigned to that project?

Did you ask for it, or did someone bring it to you?

Ei-Nyung: My manager clearly saw how upset I was. I was not a person that was used to crying at work. I was like, you do not do that, especially as a woman. You shut that down.

Heidi: Yeah.

Ei-Nyung: But I cried for her a couple times. I was like, this is so unprofessional. I was apologizing. I'm so emotional about this.

And so she clearly knew I wanted to do stuff. Like I felt like I should be promoted and needed to be promoted to be happy, right?

Heidi: Mm-hmm.

Ei-Nyung: Not happy—to feel like I had what was fair. I think that was the thing. I was always looking for fairness and equity.

Heidi: Yeah.

Ei-Nyung: And I was like, I don't want it for the title, I want it for equity.

Heidi: Yeah.

Ei-Nyung: I'm not trying to like slag on anyone. I was like, some of them in the tier above me are not contributing as much to Slack engineering as I am. And I know that for a fact, you know?

Heidi: Yeah. Yeah.

Ei-Nyung: And so I was like, I just. I should be where they are.

Heidi: Yeah.

Ei-Nyung: But I did get a project, she, she found it for, well, we needed to do the project. Like, every department had a part of this internationalization project that they needed to do.

Almost every department, and our department had our slice. But what happened was that because I had prior internationalization experience from way back in my other jobs, and because I've been a proven tech lead for projects before, I got chosen as a tech lead for this whole project.

Heidi: Oh, cool.

Ei-Nyung: And so I had to coordinate different departments and check in code on their code bases and do all sorts of weird stuff.

And that project was awesome because I think, generally, there would be like eight or nine people that came to meetings, and all of them were women of color, or there was one white guy, but we were all like women of color or women from different countries.

And we were like, this is really nice, and sorry, I feel like I'm being incredibly sexist, but I was like, I feel like this project's going so well. It's so unstressful, and everyone's like, this is the most unstressful project I've ever had, and it's going so smoothly.

Heidi: I love that.

Ei-Nyung: It is, right?

Heidi: Love that.

Ei-Nyung: It went so smoothly. And the thing is, it wasn't going smoothly because we were all just being agreeable. It was going smoothly 'cause it was working.

Like our work was top-tier. We got stuff done.

Heidi: That's awesome.

Ei-Nyung: And we were able to write code that affected the entire project. And it was a refactoring project, unfortunately. No, it wasn't ref— Actually, the thing that got me promoted was a refactoring part of the internationalization project. The project itself was just shipped out to multiple different new languages and locales.

Heidi: That's cool.

Ei-Nyung: But we secretly refactored.

Heidi: Yeah. Yeah.

Ei-Nyung: So that got me promoted. But the bow on the whole thing is that, Cal, the CTO, would do a little announcement to the whole company when someone got promoted.

Heidi: Mm-hmm.

Ei-Nyung: And he usually will review... or your manager will write the blurb and review it with you.

They reviewed it with me and they put like, oh, Ei-Nyung is really well known for her technical leadership, blah, blah, blah, blah, blah, and you may also know about her mentorship and blah, blah. I was like, no, can we do it the other way? I literally was like, I know I didn't get promoted on it, but I want people to know that what I'm actually known for is caring about bringing up the whole organization and caring about... specifically looking into underrepresented people.

So I was like, shuffle the order, please.

Heidi: Yeah.

Ei-Nyung: And so they did. And, and so many people reached out and they're like, I can't believe you got promoted on that! I didn't. I'm known for that. [laughs]

Heidi: You're known for that. I love that. I love that. That's amazing. I can definitely hear that passion for mentorship and bringing others.

And you had mentioned it one point that, after Salesforce acquired Slack, you got lured away for your dream job. What is your dream job? And maybe tell a little bit about whether that really was your dream job or not, or maybe how you feel like you have crafted your dream scenario now?

Ei-Nyung: Yeah. I think the answer to the final question is I have, and I will get into it more. So at the time, I had become a senior staff. That's only like, I think there were only like 16 people and maybe there were 20 senior staff at Slack. All of Slack across all departments.

Heidi: Mm-hmm.

Ei-Nyung: All engineering departments, and there were like eight principles?

Heidi: Mm-hmm.

Ei-Nyung: And at that point we had, I don't know, 900 engineers or something.

Heidi: Wow.

Ei-Nyung: So I was pretty proud of myself, but I was also like, huh, we got acquired about a year ago. I actually know from… 'cause all the startups I've been at, aside from my own, have been acquired. And I always would stay about a year and realized this is no good.

Heidi: Oh.

Ei-Nyung: I was like, even in the best circumstances of this acquisition, it's not gonna feel like Slack in about a year or two, and I'm almost fully vested. With the major portions I got. 'Cause I was there for the DPO, also.

Heidi: Yeah.

Ei-Nyung: Which was great. So I was like, I should think about leaving. But I was like, okay, you have to wait until you get that last chunk.

You gotta wait the last chunk. Just keep waiting. It's fine. You're happy. And I was happy, so I was like, why would I quit? So I wasn't looking.

But actually, it's related to the internationalization project. I wrote this LinkedIn message where I was all weepy about.... Because one of the languages that we rolled out Slack to was Korean.

Heidi: Mm-hmm.

Ei-Nyung: And like, my Korean is not great. Business Korean is terrible. I have no idea what business Korean is, or like any technical Korean, but I can speak like a random middle schooler, I guess, right? But that knowledge was actually fairly useful for certain parts of the project. And the other people in the team also spoke different languages, so this was incredibly useful.

Heidi: Yeah.

Ei-Nyung: And so... and that was where bringing our full selves to work was actually genuinely useful in a specific way. I wrote this message about like, "Hey, we put this out," but I was like, I put in a personal part, which was like, this is the first time in my, at the time, like 21 or 23 years of working where I've been able to send my mom, who doesn't speak English very well, just tiny bit, something about what I actually did at work. 'Cause they had a press release, right?

Heidi: Mm-hmm.

Ei-Nyung: Like an announcement, a blog post about the project we did. So I was able to give it to her in a way that she could understand it.

Heidi: I love it.

Ei-Nyung: And like, sorry, that meant more to me than I thought it would mean, and so like I said, I wrote a really weepy message, and then someone emailed me about it… like didn't send me a LinkedIn, like someone emailed me about it, and it's like, “Hey, Ei-Nyung.”

But also using like a title for me that indicates she's obviously Korean. Right?

Heidi: Oh, wow.

Ei-Nyung: She was saying how she moved she was by what I wrote, and that… she said, a lot of these things are genuine and personal, and I was like, and definitely wasn't a bot.

Heidi: Yeah.

Ei-Nyung: Definitely wasn't just summarizing whatever I wrote to like, recruit, right?

Heidi: Yeah.

Ei-Nyung: And I was like, huh, I'm gonna actually write back to this person. Because she's like, I really relate to that because I also don't speak Korean very well. And you know, my mom doesn't know, like yada yada. I was like, oh yeah, this is very relatable. So I wrote back to her and she was very transparent also that it is a recruiting attempt.

I was like, alright lady, I'm not looking to leave. That's like another six months, maybe six to nine months from now.

Heidi: Yeah.

Ei-Nyung: But we talked, and she was like, but could you please? Like, and I loved her. I'm still in touch with her. She's amazing. She's such a great person. Like, incredible, like the fastest, best engineer I know.

And the nicest human being with such a kind heart.

Heidi: Oh, I love that.

Ei-Nyung: Yeah. She's the best engineer I know, actually. So, she was like, please talk to my CEO. I'm like, nah. Like please talk to my C—No. But then a couple weeks later, she's like, he's in town. Can you like meet him? He's in Oakland. And I was like, oh, uh, okay.

I guess that's like super close. I guess I'll meet him.

Heidi: Yeah.

Ei-Nyung: But he knows I don't want a job, right? And so we chatted and he was like, well, you know... "Person" tells me that you're not looking for a job, but tell me what are you looking for after you're done with Slack? And I was like, well, at most companies, if you're like a principal engineer or the high level engineering lead, a lot of your work ends up being, I wanna say like 70 to 90% technical where you are leading on the technical initiatives and there's only a little bit of time for mentoring and really a negligible amount of coding.

You only do it for prototyping probably.

Heidi: Yep.

Ei-Nyung: But I was like, I love the technical side. I actually don't wanna walk away from the technical side. I grew to really enjoy it. It scratches an itch, but I love mentoring and I'm like, there's not enough people who are trying to not just do great and feel good and get rewarded, but be like, hey, we want more of other people that are gonna excel in their own different way, right?

And like, be great. And I'm like, that's what I want. I wanna be like able to, like, instead of taking the project, help someone do the project because it's their first time doing something of that scope, and that's the kind of principal engineer I want to be.

I was also like, and I mentioned the mentorship programs to him that I had started at Slack and I was like, you know, when I was doing it all by myself for the first three cycles or so, I literally was looking at these Google forms, putting them in Post-its, and trying to match people, and I a hundred percent prioritized women and people of color.

Heidi: Mm-hmm.

Ei-Nyung: And I was like, I'm gonna get them the best mentor match. I'm gonna give them the best ones, right? And I'm like, you know, I'm sorry, everyone else, but all the mentors were good. All the mentors were so amazing. I think that's the testament to at least the front-end engineering team of Slack at the time.

People are just wonderful. So. That was a really wonderful thing that, and I told him is like, ideally I would be helping so many people who are underrepresented who don't get the same trajectory chances that, you know, other people get to. But I wanna be involved technically, but I wanna help mentor.

And he says, "What if we made that job for you?" What if we were, I mean, he's like, we are trying to hire from a diverse pool. We have N number of women, blah, blah, blah. He gave me some stats and this many people in the pipeline, yada, yada. And I was like, oh, this does sound good. And he's like, yeah, so we already want a diverse pipeline, and we do think that some of the people could use some either technical or leadership coaching.

There are people who are incredibly technical that do not know how to lead a project because they don't communicate. They just write the code and then, and then vice versa, right? Like people who have really great team skills and leadership skills, but are a little lagging on the technical side.

And I was like, huh. And he's like, and you'd be salaried of course, but that would be your whole responsibility. I was like—

Heidi: What's the catch?

Ei-Nyung: I literally said, what's the catch? Like how could this work? What would I do? And he described some of that stuff to me. And we continued to talk, and they sent me a job rec that I helped write.

And the job rec was very specific that that was my role, right?

Heidi: Wow.

Ei-Nyung: But I went, and what they really needed was really fast, smart, technical people. They needed people to be writing the code.

Heidi: Yeah.

Ei-Nyung: They couldn't afford… they shouldn't have hired me. Oh, so they did lure me away.

Heidi: Yeah.

Ei-Nyung: And I left with three-quarters unvested, which I still regret.

Heidi: Oh no.

Ei-Nyung: It was not the right place for me for a lot of reasons. Some of which I feel like I shouldn't say. Not the right place for me. I was incredibly miserable. It was a... for me personally, it was my worst experience at a startup.

Heidi: Mm. That's too bad.

Ei-Nyung: Even though for a lot of other people, they said it's their best experience, so people differ, right? And I don't wanna paint a picture where like it's evil. It wasn't for me.

And I was miserable. I was gonna leave after the first three weeks, actually. And my husband was like, you sure? And I was like, I don't know. He's like, well, what if you stuck it out a little longer? And he was right. Because if I walked away then, I would've been like, what did I walk away from?

Heidi: Right.

Ei-Nyung: But I ended up walking away at nine months.

Heidi: Yeah.

Ei-Nyung: But I still stayed in touch with them. They brought me on as a technical advisor, so I continued to vest shares, and I was mentoring people who reached out to me. So that was fun for a while, but at some point, I felt like I wasn't very useful to them.

So I was like, I'm enjoying this, but I don't think you're getting the value you should get. Let's cut this off. So they did.

Heidi: Yeah.

Ei-Nyung: And then they got acquired last year, so I did make a little, a little....

Heidi: Well, it's always good to recognize that even in a... you know, I think it... to have your dream job, you sort of have to have both what you need, but also what you know, what they need as well.

So, yeah, I can see being aware about that is really great.

Ei-Nyung: Yeah, that mismatch was so terrible.

Heidi: So, you know, sometimes it just doesn't pan out exactly how you want. But amazing that they created that opportunity for you. How did you pivot from there into what you're doing now, which sounds very much like it is your dream job and exactly what you were hoping for yourself?

Ei-Nyung: Yeah, so the funny thing is, after I quit that job, I actually immediately went back to mentoring and coaching.

Heidi: Mm-hmm.

Ei-Nyung: And it was actually my first time charging people for coaching. Before that, it was all volunteer mentorship, and I was mentoring at like six different organizations, and at Slack, I just really like it, and I was like, oh wait, I can get this piece here, like in the coaching and mentoring.

Well, could I get the technical piece somewhere else? Ah, through startup advising, there is a lot of working with this technical stuff. It's like, hey, those would be bad technical decisions. That makes the system too complicated. Oh, do you need to do a round loop?

So, I was able to be involved in that way with the startups and also a little bit of coaching, but with the startups, there's fewer startups than there are underrepresented people that are engineers or, you know, about to be managers.

So I wanted to do women of color as my startup people, but some of them aren't, but they're still wonderful people, right? Sorry, I just really feel like I'm saying something bad. [laughter]

Heidi: No worries.

Ei-Nyung: They're fine too. Yeah. And the thing is, I super enjoy working with... I think there's just this relaxation and understanding when we're like, let's just talk real stuff, right?

Heidi: I love it.

Ei-Nyung: So I get that, and I think the thing I was missing about it was the little bit where I get to work in a team and write code, because I kind of miss that too. And, oh, actually, this ties into what I'm doing with my niece. I've taken her on as an apprentice. She's doing UX design and UI/UX for me, as well as web, like actual implementation.

And I'm writing the actual code. So we're doing some of... we have like regular standups, we have meetings where we're like, what are we gonna do next? Did that make any sense? And so I'm training her on all this professional stuff, and it's super fun.

Heidi: I love that.

Ei-Nyung: Because, also, we're not doing the dumb stuff people don't like at work, right? We don't have like a million tickets. We don't have standups that last two hours.

Heidi: Yeah. Yeah.

Ei-Nyung: You talk about the stuff that needs to get talked about and exchange information we need to, and I'm extremely happy with the stuff she's doing, and she's probably okay with what I'm doing. Yeah.

Heidi: I'm sure she is. You must be the best aunt ever. That's so cool.

Ei-Nyung: But it's been fun little projects. For instance, our first one was, um, so I recently got into K-Pop.

Heidi: Oh, nice.

Ei-Nyung: Yeah. And it's a little bead count estimator for if you're making concert bracelets.

Heidi: Mm-hmm.

Ei-Nyung: Because I was always running outta beads at the wrong time.

So you can like, whatever. And then the second one was, uh, I'm specifically into BTS, and they just had a comeback. [laughs] Um, that one was, you know, the game Connections that New York Times has?

Heidi: Mm-hmm.

Ei-Nyung: This is a Connections clone, but it's only BTS stuff.

Heidi: Oh my gosh. That's awesome. I love it.

Ei-Nyung: And the third one is we're gonna do a K-pop DB.

Kind of like IMDB and the data requirement is ridiculous. We're like, we'll never be able to fill out the data. We're gonna just start with two groups that we like and see if anyone even likes that. You know?

Heidi: What a fun thing. I love that you're getting your technical, your mentoring and coaching, and doing a startup with her at the same time. So it's all the fun stuff together.

Well, I wanna thank you so much for your time today. It's been really fun to hear your journey and all of your insights along the way. And I just, I really love that you have creatively been able to construct an amazing set of opportunities for yourself to sort of get everything you need and have the self-awareness of what you love and be able to follow those things that give you joy.

So, really inspirational, and thank you so much for taking the time. I've just really enjoyed our conversation.

Ei-Nyung:

And thank you so much. This was super fun for me, and I hope we can do something like this again.

Heidi:

Alright, well thank you. And I also wanna say, shout out for all the support you've given WEST over the years.

Thank you so much for leading conversations, leadership talks, career development workshops, mentoring, et cetera. So thank you so much, and I really just appreciate everything you've done for the WEST community over the years. So thank you.

Karen: Engineer Your Career is produced by WEST, a learning community that empowers women technologists through mentorship.

Special thanks to our audio production team, Heidi Williams, Amanda Beaty, and yours truly, Karen Ko. If you enjoy our work, we encourage you to share this episode with a friend. Want to hear more from Engineer Your Career? Subscribe on your favorite podcasting app. We look forward to having you back for our next episode.

Thanks for tuning in.