Varun Rajan 0:07

Welcome back to the Push/Pull Podcast. I'm Varun Rajan. when I started this podcast, I named it Push/Pull because it was about career transitions, the forces that push you out of one thing and pull you towards the next. And that's definitely still in here in the conversations that I'm having, but somewhere between when I started this podcast and now, the show has become something a little different. It's becoming a lot more about the future of work, and more specifically, about what it takes to build a life through work that actually holds up. What's durable, what you can carry forward when everything else is shifting right now in 2026 with the macroeconomic environment and AI. My guest today is Helen Huang. Helen is a product leader, a two-time founder, and the creator of Trove, a company building what she describes as the behavioral identity layer for the internet. The short version is that it's a product that helps you understand yourself through what you do and not just what you say. And you'll hear when we get into the conversation, that distinction matters a lot. there are a ton of potential applications for Trove, especially hiring and recruiting and how job seekers are able to present an accurate depiction of themselves based on what they do, kind of a character profile, if you will As someone that's spent my career focused on adult learning and the talent space, I am super interested in how people are figuring out how to show up as job seekers As well as how people approach upskilling themselves at the jobs that they have right now and so I was super excited to talk to Helen about what she's building right now Helen has had one of the more interesting career arcs I've gotten to learn about this season. She went from earth science to product management at Zynga, Microsoft, GitHub, To founding Colab, an edtech company that she bootstrapped to seven figures, to taking a year off, to building Trove. And somewhere in that gap year, she also hosted a garbage bag fashion show, uh, and I'll let her explain that one when we get into the conversation. What I'll say going in is that Helen is someone who combines genuine curiosity, a real care for people finding fulfillment and success in their lives, and a bias towards just doing things that I find genuinely refreshing. And I think you'll hear it too. We're here with Helen Huang. How you doing Helen?

Helen Huang 2:42

doing good.

Varun Rajan 2:43

Awesome. Um, remind me again. Okay, so when did we last connect? It was probably like five or so years ago. I remember getting in touch with you. You were working on CoLab,

Helen Huang 2:54

Yep.

Varun Rajan 2:54

you were a founder of CoLab. Uh, and I think I was, uh, I was at Chegg Skills at the time. We were working on trying to find ways for bootcamp students to, to get jobs, and I think that was kind of the, the basis for our conversation back then.

Helen Huang 3:05

No. Exactly.

Varun Rajan 3:07

Yeah.

Helen Huang 3:07

I think we were trying to either to talk about like a partnership of some sort or some sort Yeah. Some sort of pathway to experiential learning and like hands-on learning. but yeah, that's definitely the last time that I got in touch with you.

Varun Rajan 3:19

Yeah. and ultimately I think that we're still focused on a lot of the same problem sets, which is one of the reasons I'm really excited to talk to you today. Uh, tell me before I start asking about troves specifically and, and all these other things, I also want to get a sense of like your whole career trajectory and story and all that kind of stuff, but, um, tell us a little bit about yourself and, uh, how you would introduce yourself and what you care about.

Helen Huang 3:44

Cool. oh gosh, yeah. I haven't had

Varun Rajan 3:46

I.

Helen Huang 3:47

or interview or anything for so long. I've just been heads down grinding by myself on Trove, so it's nice to be asked again. It's nice to believe that someone cares. okay. Anyhow, so my background, I was born in China. I immigrated to Canada as a kid. I graduated from the University of Waterloo, but not in. or computer science. I actually studied earth science, and then realized that I wanted to pivot into tech. That pivot was extremely hard, but I ended up finding my way. so I was a product person, at Zynga first, and then I ended up moving to Seattle, to work at Microsoft and later GitHub, as also a pm. then in 2021, I ended up moving back to Toronto to start up my last company CoLab. So that was fully bootstrapped, and again, as that was all around experiential learning, like helping non-traditional tech talent break into the industry, helping career switchers get the experience, confidence, and community that they needed to really transition into a career that was gonna be better for them. so I did that for a couple years and the company is actually still going. It's now led by my co-founder, Fumi. and they're still doing some pretty good stuff even to date, but I left that in 2024, mainly to one, pursue a little bit of a gap year. but there was so much happening within AI at the time, and it's only increased now, but the feeling that I got was, whoa, okay. I need to take the time to actually learn all of these skills from the ground up because there's gonna be a fundamental shift. I'm excited to see what I can do within it, really. So I ended up taking a, gap year, an adult gap year between 2024 to 2025. and in the later part of that gap year, starting to play around with a lot more different ideas and AI all around the concept of helping people live authentically, helping them find where is the right fit for them. Like all of those kinds of themes. Essentially I care a lot about ai, being part of our lives, but how can we make humans more human and how can we allow human relationships to flourish, while centering the individual? So a lot of those kinds of themes, and that's also how I ended up, up landing on Trove. but I would say that's a little bit of like a spiral of what has brought us here.

Varun Rajan 5:57

Yeah, totally. I'd love to dig into a little bit more of what you just called a spiral, because I think there's probably a really compelling story there. when you decided early on that you wanted to pivot into tech from the kind of like earth sciences stuff that your education was leading you into, what was there any sort of clarifying moment that kind of brought you there? what were the things that you were like. Looking to achieve or get done. when you made that switch?

Helen Huang 6:22

Honestly, Varun, all my reasons are so silly. and I think I'm a good example of somebody who. Like a good example that you don't need to know exactly what it is that you want to do in order to eventually make the impact that you wanna make. Because I feel like I've spoken to so many students that are very clear as to what it is that they wanna achieve. Like they wanna be a founder, they wanna be a pm, they wanna be in text, stuff like that. but that was actually never my story at all. I wanted to get into tech because my boyfriend at the time was in the US and so I needed to get. Away into the US and the only companies that would sponsor visas were tech companies. that is actually the only reason completely. I had no idea what product management was. all, like, all of those things came together. and I think that's also why nowadays I really believe that you have to just take one step in front of the other because you'll discover the plethora of opportunities as you do that. and that you don't need to plan so much and be so much in your head to ultimately execute something that you are really passionate about. But no, I had no real, I had no North Star, no pulling vision. I have that now, but back then there was nothing.

Varun Rajan 7:31

No, that's that. That's great. That's actually like super insightful. I'm curious what, when you were looking for those jobs and you had that kind of want you just like you needed to get into the us you wanted to be with your partner at the time, how did that kind of how did that desire or aim or outcome that you wanted, did that translate into how you were showing up in actually, like searching for those opportunities, how you were pitching yourself as a PM and all that kind of stuff? or was it a hindrance? did it feel like, you talk a little bit about putting one step in front of the other and not necessarily knowing exactly what you want while you're pursuing it, because your reasons were pretty. like divergent from the actual like day-to-day job.

Helen Huang 8:08

Right.

Varun Rajan 8:09

yeah. So I'm curious, like, did it fuel you in certain ways? Did it hold you back in, in others?

Helen Huang 8:14

I would say that I ended up breaking up with that boyfriend and I was never able to make it into the US while we were together.

Varun Rajan 8:21

Okay.

Helen Huang 8:21

even though that was the initial spark, it didn't end up happening, which is also totally fine. I'm happy with how things ended up now, but, so I would say that during the job search process, I. In hindsight, all of the things that we ended up teaching at CoLab, and I'm sure you guys taught your students at Chegg, I didn't actually take advantage of any of those things. I wasn't reaching out to anybody that I knew wasn't hitting up recruiters or hiring managers, was not even doing mock interviews with my friends. again, it was all a reasonably silly way of breaking in, but I would say the one thing that never. Faltered was just the perseverance and the never giving up.'cause I think, again, speaking to even some students now trying to make a pivot or trying to get their first full-time job, I think a lot of them are relying on tools. They're relying on not having to submit so many apps. for reference, my own pipeline at the time, I think, and this was pre any AI tools helping any sort of submission. Keep in mind, I was at 800 apps where I was probably half of them. Personally crafting a actual cover letter. And of the 800, I only had four interviews, so I think, and now as for showing up for those interviews, I definitely grinded and I like interviewed craft by myself a lot. And it wasn't at the time, it was really a realization that the goal is to get the role and to see what

Varun Rajan 9:45

Yep.

Helen Huang 9:45

in the role. Not necessarily for any personal reason, but. But yeah, no, I think looking back it's really interesting because that those job apps, like I did that over the span of probably two, three months. and yeah, it was very disheartening to like never hear back for even the ones that I would put in a lot of effort for the cover letter. and again, I think part of it is. At the time, like my background and what it is that I was studying, it didn't really pattern match the expectation that a lot of recruiters or hiring managers had as well, right? Because that's how we treat a resume. it doesn't really look at what you're capable of, it just looks at what you've done. yeah, I feel like I've been through that and I give my old self a pat on the back for persevering.

Varun Rajan 10:27

Yeah. No, that, that's awesome. and I think I, I love that it comes back to that insight of the resume being like what you've done and not really a good signal for capability as a candidate for a job. I don't know how much you wanna go through the. Time that you were a PM at Microsoft and a GitHub. but I'm genuinely curious about what you liked about it. What were the things that were difficult about it and ultimately you chose to move on. There was a move associated with it, right? Like a physical move going back to Canada, to Toronto, if I recall correctly. but you moved. Being a founder. so I'm curious about what was it that you experienced in those roles ultimately that you liked and didn't like, and how did that inform the transition that you ultimately made?

Helen Huang 11:05

I'm so grateful to have done those roles, honestly, as a pm'cause I truly recognize now

Varun Rajan 11:10

I.

Helen Huang 11:11

when they say product is so similar to being like a mini CEO. I will say for anyone listening that. There's a lot of differences as well, but some of the traits that I was able to learn around like project management communication, like cross-functional team development, right? All of these things are so core to what it takes to also be a founder. and I think during my time at Zynga, Microsoft, and GitHub, because there was both like a ina a very crazy time period where. I was on a product with only one other PM who was my manager, and we, were getting sued at the time and had to like, change our name and then our reviews tanked to one star. And then the CEO of Zynga at the time emailed our team as like an example of what not to do. So that was like a very stressful, hectic time, all the way through to now. Big, bigger, much bigger company figuring out how to navigate. What it actually means to work at a big company and seeing how things are structured, how teams are structured, how projects flow, flow down and map up to a greater vision, how that vision is communicated. I feel like those were all amazing things that I was really grateful to learn. there was also, Like one of my managers, like one of my first managers at Microsoft also said something that I still carry with me today, which was, Hey, at the time I think I had submitted a spec and like people gave me all sorts of feedback and I felt oh, why didn't I get this perfectly right? Like, why is there this feedback? he had just like an offhand comment about, oh, if everything was went perfectly the first time around, like life would be extremely boring. and sometimes I still think back to that, so many years ago. And I think about how I go through the things I do now and the mistakes that I make. And yeah, actually if I did get it for perfectly the first time, like there would be really no purpose, and it just wouldn't feel exactly the same. So again, a lot of really solid stuff that I felt I learned from. Working in corporate, and working alongside people, and also professionalism. So of those things I think I was able to bring to my first company and now hopefully to my second.

Varun Rajan 13:16

Yeah. and, and, and tell me about the decision to, to leave corporate and start your own thing.

Helen Huang 13:22

so at the time, EdTech was also booming at the time, so part of it was a great market for what it is that we were trying to do. Me and my co-founder for CoLab, Sefunmi, and I think we just felt significant user pull. We were getting a lot of like inbound people interested in the exact thing we were trying to solve, which was again, helping people like ourselves break into the industry.'cause both him and I had the experience of like how difficult it is when you might not have the right matching background. so that's what we were super passionate about. And then when we were getting a bunch of people messaging in responding to what it is that we were posting, sharing what it is that we were saying, I think it was a very clear. sign that. Okay. we're really onto something here. so we had the pull from the company side, but at the same time, I think, again, I had been at Microsoft for ar almost four years at that point. and I was also excited to try something new. I never saw myself really as a entrepreneur. like I didn't go into my work thinking that, oh, eventually I'm gonna be a founder. it really wasn't a thought in my mind. I liked working on projects, I liked doing things, and I liked, like helping people. but I think it really took my co-founder, to pull and be like, Hey, why don't we actually just try this out for real? and so quit my job. was confident that we were gonna make 200 k That first year did not happen. did not make 200 k. First year, second year, did not make any money first year, frankly.'cause we were just fully bootstrapped, but wouldn't go back and change it for the world anyway.

Varun Rajan 14:55

Yeah. Um, tell me a little bit about the process of, of building CoLab and, and lead me up to the, kind of like the decision of taking a career break ultimately.

Helen Huang 15:05

Yeah, building CoLab was so much fun. It was so much fun and I'm I, looking back, I also recognize how lucky. it was seen as, it was literally my first ever company. I had never tried to build anything really for money before that at that point. So I feel really grateful for the amount of progress we were able to make from a business perspective.'cause we were able to bootstrap it to over seven figures in revenue, and profitability by the end of the four years. but also on the impact side. Because we ended up graduating over 2,500 students all around the world. many of which had never been even able to like, build their confidence at all in the workplace. So I think being able to grow people's confidence was really heartwarming to me. and also in our final, like in 2024, 2025 as well, and probably also this year, we were also able to train hundreds of black Canadians in product and ai, as well. I feel really happy about all of the progress that we were able to make. I think there was, in 2024, there were a lot of changes as well with our business model, right? Like the industry was not doing well on its own, which is also why we pivoted partially into working with like government and working with like provincial government to facilitate a lot of these training programs so that they could be free. That we were able to deliver them to more people.

Varun Rajan 16:28

Oh, very cool.

Helen Huang 16:28

we were around that frame, like frame phase of company. but I projected ahead, I could also see that was unlikely to change in the upcoming few years, frankly. Because, I fundamentally believe that good education, like education at depth cannot scale. That is my hot take.

Varun Rajan 16:50

Yeah.

Helen Huang 16:51

because if you wanna educate and do it really well, you just can't think about it from the perspective of, oh, I'm gonna try to hit millions or Right. Because you're just not gonna have the real impact on every single individual that. You might need to achieve. so in 2024, that was the main thing on my mind. And again, as mentioned, I was like already building out little side projects, not side projects, but embedded AI tooling for CoLab while I was still there. and got my enthusiasm up really high as to what it is that we could achieve in the future. But I also knew that. Transitioning CoLab from a company that was doing well and really supporting students at depth into something that could really leverage AI in the way that we could see hockey stick growth, which I was also interested in. probably just wasn't gonna happen. So the good thing is that my co-founder was also really supportive. We had a long period of conversations about it. and so we ended up deciding, hey, he was gonna take the company forward in all of the things that we've achieved to date. Without me, and that I was gonna step back and chill out for a year.

Varun Rajan 17:57

That's awesome. Um, there, there's a lot there that really resonates with me, especially having been somebody that's worked in education and like worked on, you know, online coding boot camps and, and all that kind of stuff. The idea that. Education, like at depth, like doesn't necessarily scale because it's a very human endeavor. People learn very differently. the, it it, it brings up a couple of different questions that I have. One is did, did you see, was, was that something that, was that a hypothesis that developed, that informed kind of more of your experimentation with ai like. Within CoLab, right? Being like, okay, how do we achieve this hockey stick growth? Things are changing in the market. There are new tools at our disposal. there's Khan Academy doing all of this stuff for like personalization and so, so we're, so was Chegg and all, all of these other ed tech companies are kind of like moving in that direction because there's this new capability that's like cannibalizing a bunch of different businesses, but at the same time could enable something really amazing for learners, right? and so it, so it's kind of like a two-prong question. One is, did that inform kind of what you were trying out? and ultimately it sounded like you landed on that spot of like, I don't think that, like the kind of growth that we're aiming for is gonna be possible. And the second question is like, what do you think, as, you know, as CoLab as you've seen it, kind of like adapt to the new environment and like train folks on AI and all that kinda stuff. What do you think people who are, evangelizing AI tools and adoption of AI tools are, are getting wrong today? Because I, I have so some takes on that too, but I'd be curious to know, yeah, like both from your experience, what you were seeing in terms of how education could scale, uh, given the fact that there's all of these like. Developing tools. and then also it's like what are people getting right and wrong about where we think the future is headed in terms of how we're skilling people for the workforce.

Helen Huang 19:48

both solid questions. I'll start with the first one. I think the first thing with CoLab is. we didn't understand our users as deeply as I believe we should have. because the entire positioning, not entire positioning'cause we would never position it as if we were gonna help like students get a job, but. is, if that is the end goal expectation of a student, then you have to help them in the areas that they actually need help. Which means establishing more of a team on the, like the post learning experience, for example. But Fumi and I were both very focused at the initial stages of, hey, just the education phase.'cause the whole concept was that. I think one thing that career switchers get wrong, is that the goal is to land a job the goal is actually to succeed in the role, right? It's to be in a place where you can flourish and you're learning what you wanna learn and you are respected and like that. That is the goal. and I think that is one positioning piece that all boot camps. Generally don't focus on, but is also the goal. But then I think with bootcamps, I have so many thoughts about bootcamps at this point in time that I just will, not rant about for now. I think they're great. I think they're great. I think they're a great learning playground for people to try new skills and to meet new people. and I think doing a cohort based approach where others can learn alongside other people, I think that's awesome. But I do think that the expectations and the business models that follow some of these bootcamps are not the right things to necessarily do, but that's like neither here nor there. The tools that I was making at the time were primarily geared around student success. Throughout the programming. Throughout the programming. and the other realization that I had was from our users that, hey, what they really wanted was they wanted to land a role. They wanted intros, they wanted all of the referrals that came from after. and I think at the end of the day, it doesn't make sense to create tools to use in situations that. People aren't actually asking for. the goal isn't for me to make a tool, right? It's for me to help a customer or a user achieve a thing that they want to achieve.

Varun Rajan 22:06

Yep.

Helen Huang 22:06

and so the business model and how we were orienting the company just wasn't suited for that, right? Because we were very focused on the education piece.

Varun Rajan 22:14

And then.

Helen Huang 22:15

I also have my own thoughts on personalized learning and like what that actually means. Because part of learning means being. like discovering and learning about all sorts of various things that you might not like. but I think nowadays when we think personalized learning, it's just, oh, tailored to exactly what's right for you. But what's right for you is developed in the difference and like robustness of experiences that you gain, right? So I have also my own thoughts about what intentional personalized learning means. but all of those things were not relevant to CoLab, basically,

Varun Rajan 22:49

but it makes sense, right? Like it's, it's a lot of, there's so much of the tools and so much of how we talk about this stuff where it's like, how do we remove as much friction as possible, but Part of learning is the friction of

Helen Huang 22:58

Yes,

Varun Rajan 22:59

with things that you don't like, that you don't understand through methods and, and, and, you know, channels that you don't get, in order to like get to those aha moments afterwards. Right. Like the process is very much the, the product in that sense.

Helen Huang 23:11

exactly.

Varun Rajan 23:12

cool.

Helen Huang 23:12

Did I answer in the two questions? I

Varun Rajan 23:14

no. yeah. I think you did. I think it makes a lot of sense. I think also just generally, not just from a, like a. Like a bootcamp perspective, but also the other thing is the sense that I get a lot of the content that I see about AI tools and bringing things up, like for me feels very scarcity based. Like it feels like very fear oriented. and that really rubs me the wrong way. And that's something that I'm feeling like, I really wanna see less of, I wanna see more about like the opportunity, like more about having fun, like more about

Helen Huang 23:46

Totally.

Varun Rajan 23:47

to dig into something because you're excited about it. I'm worried that we're like scaring people away from, being more effective. and so that, that's how, yeah.

Helen Huang 23:55

I totally agree with that as well. I think, if you're under pressure and under tension, how are you gonna learn effectively? I think we've gotten used to this kind of like fear-based mechanism driving news headlines and LinkedIn posts and stuff like that. but yeah, I think it's important to recognize that like time. Things are changing. It's probably not changing as fast as many would like you to believe, but. I think to be a holistic, curious individual is a good trait. And so if we're able to help people recognize that, hey, there's gonna be certain things in this new world that they can adopt and be really good at, or just be curious in learning, and that it's gonna help them in their careers, but they don't need to fully throw away all of the things that they've done in the past. It doesn't remove the expertise that they do have. It does have an opportunity to like. Improve and help them. I think if we use that kind of language, the expectation and like the excitement will come back to learn some of these tools, rather than, oh, we're being left behind. Like we're never, we're out of jobs. we're in the permanent underclass. what's the purpose of this?

Varun Rajan 24:59

tell us about the time off. I'd love to hear about the goals that you had in mind. so te tell me a little bit about what you thought you were gonna be doing, going into it. How did it evolve?

Helen Huang 25:09

in hindsight, I think a year was a bit long. but when I first started my gap year, like I was. was trying to hit a year, so in my mind I was like, Hey, I actually want the full year off. I'm very grateful that I was able to and had the personal runway to do that, which I know not everyone has. which is also why I'm like, okay, in hindsight, maybe I didn't need the full year. I went in thinking that, okay, I'm gonna relax for the first, like month or two, and then I'm gonna get right on it. I signed up for these AI courses, didn't take them. my one to two months of relaxation was actually more filled with. I make the right decision? Should I go back? oh no, I'm screwed. Because this was also around the time when like AI was picking back up again and it was like, oh, if you don't have a job now, you better get a job now.'cause like jobs are gonna go away. So then I was like, oh, did I really pick the right time? Am I gonna have a job? what if I don't level up enough? in, in hindsight, I probably shouldn't have worried about those things, but definitely even going in prepared, still felt those things.

Varun Rajan 26:17

Yeah.

Helen Huang 26:17

was really interesting. and so what ended up happening is in the first quarter I, at the end of the first quarter, I was like, oh, man, I need to find a job. So then I started looking for jobs. and I actually went pretty far in the process, like even got an offer for a senior PM role out of New York, but it just didn't like it, it didn't resonate in my heart.'cause I think one thing I didn't realize from just my time at CoLab is how deeply I would care and could care about a mission. and how just money is really a super. Big driver for me anymore. Which I think previously, like being in FAANG, a lot of your peers, like that's what you're talking about. You're talking about comparing total comp. and it taught me that, oh, actually the years of working on CoLab and like the years of doing something that I really felt like had value and helped others, um, I can't let go of that anymore. So I think that was a really interesting learning in the first half year of my, sabbatical or gap year. And then that realization also kicked off the desire to learn again. So the course that I had taken in week, like in month one, I ended up taking in like month seven. it was great. Learning AI tools like cloud code, et cetera. I ended up vibe coding. My entire personal website took a long time at the time, but I was really proud of having actually been able to do something like that, especially coming from an earth science background and especially having built a company on, oh, if you're non-technical, you gotta play to your strengths. But realizing that the non-technical label is also something that you give yourself. so lots of like just internal work and like learnings there. I ended up hosting a garbage bag fashion show.

Varun Rajan 28:05

Yeah. Tell me about that.

Helen Huang 28:06

that was so fun. the whole purpose was, honestly there was no purpose. I just really wanted to do it. And what I wanted to do specifically was I wanted to trick attendees into not realizing whether this is a real show or not. So had volunteer shopkeepers, quote unquote, who were pretending to sell garbage bags. Like I had a little magazine, I have a whole website. we had photographers, there was a runway, we had models. Like I went very deep

Varun Rajan 28:35

This was a whole social experiment that you just for fun.

Helen Huang 28:40

Yeah. We had like interviewers, we had like VIPs. it was so much fun and the whole point was, hey, can we create this like immersive world where you don't actually know what's right or what's wrong or like what the reality is? And can we pull people into this world that's fun and like whimsical and exploratory. I, which are all things that I feel like after you leave university, it's sometimes hard to get that back. And it's hard to realize that can also be part of your everyday life.

Varun Rajan 29:05

Yeah.

Helen Huang 29:06

so I was like doing things like that. I hosted a bunch of, like life wheel exercises. once we got 40 people into a room and like it was silent for 30 minutes'cause everyone was writing a letter to their future selves. So I got, I spent Q1 of 2025. Working on things like that. and then and then eventually Q3 was me getting back into the mindset of, oh, you know what? I have the desire to build something again. I

Varun Rajan 29:36

let me let me just take a step back into that, like Q1 Headspace that Helen had. it sounds like you. Acted very quickly on, like just sparks of inspiration. did you have a sense of outcomes in mind? Things that you wanted to do other than just like create a fun experience? yeah, like the, these are two complete, the examples you shared are two completely different things, right? there's the, there's the kind of like trash bag fashion show, uh, which is hilarious, immersive experience. And then there's this kind of like journaling, like, you know, silent dinner room for 30 minutes kind of thing. Um. You know, did you have goals during that time? I guess is, uh, is the short way to ask that question? Yeah.

Helen Huang 30:16

no, I didn't. and part of it is because I knew that I'm the kind of person where I can spend so long setting goals. Like I can spend forever being like, here's an OKR and here's the KPI and here's the rock underneath that and here's how it ladders up and here's how it's gonna make sense in the grand scheme of things. But part of also what I wanted to achieve, I guess just like internally, was letting that go because that is a lot of pressure for somebody who thinks a lot for an overthinker, for someone who's like hypervigilant.'cause that's how I am. I just wanted to like, with the garbage bag with baggy, that's the line, with baggy and I'll send you the link after,

Varun Rajan 30:55

yeah, please.

Helen Huang 30:56

you can even buy a bag.

Varun Rajan 30:58

Oh, amazing.

Helen Huang 31:00

the only thing I wanted to do was prove to myself that I can execute at the pace of my ideas, and. Just have a shit ton of fun.'cause I just felt I felt already dreary getting sent all of these articles about AI every day. and I just wanted something even for myself that was like, Hey, this, my world can be bigger than just the internet and Claude code. So it really was just fun, execution pace, just wanting to create a fun experience for other people.

Varun Rajan 31:31

Excellent. Awesome. Yeah. Cool. Uh, yeah. And, uh, tell me kind of what came next, how you, uh, discovered trove, what was your, what was your headspace like and, Yeah. How did that all evolve?

Helen Huang 31:43

do you want the detailed version or like the shorter version?

Varun Rajan 31:45

I think I wanna hear whatever you're inspired to tell.

Helen Huang 31:48

Okay. Okay. so basically in May of 2025 is when like my desire to start working on something kicked up again. at the time I was actually creating like a AI arbitrator for legal courts. I got really into civic tech. in that month, in that period. and so I was sitting in on all of these like open, that you could listen into as part of the public, right? And one of the common things that I was hearing at the time was a judge, who would sometimes need to be. like corrected by the representation, like the plaintiffs or the defendant or whomever, because they were making the wrong calls because they had such a backlog of continual arbitrations that they had to go through. So there were so many cases, and the situation, at least in the Ontario, like the landlord tenant board, is what I was mainly listening to. there's just such a backlog of items that people are missing the real details and. People are, getting the wrong results as a result of that, right? So I was like, okay, that's exactly what I need. So I ended up creating it. I ended up trying to speak to all of these like volunteers who, fighting for like tenant and also landlord rights. no one was interested. So I spent about a month doing that, realizing no one was interested in adopting AI for that particular problem. and then. So I was like, okay, what do I do next? I still wanna figure out like there was something around AI helping facilitate conversations, especially hard conversations where there might be benefit of having some objective view. So I swapped into helping. Co-founders.'cause I was like, okay, business partners also deal with problems. they have communication issues where some person might have a lot more background than the other. can we bridge the gap and help people communicate better, and help them resolve conflicts in their relationship? spoke to a bunch of business owners. and at the time I was also pitching this to a 16 Z speed run. I was testing out a new co-founder, so I flew to Miami to work with this new co-founder for a week. Things didn't work out. We pitched it, we didn't get in. and so that company also collapsed. at that point I was like, okay, maybe it's not in the books for me to. Be a founder again. maybe I should just apply to jobs. so I was back in my grind of applying to jobs. so I was in New York for a bit. I spent the summer in New York, but it just so happened that I, um, came across a new accelerator, or not new, but new to me, called Betaworks in New York City. So I ended up getting into this other accelerator that was right up my alley in terms of creative, consumer craft, like really paradigm changing things because I also knew that again, wasn't fit or trying to create like another verticalized B2B SaaS that's meant to. Increase efficiency because increasing efficiency also means something else to the people are there and part of the org, right? So I had a lot of my utopian thinking around some of what AI is aiming to achieve. so I knew that I didn't wanna do that. I knew I wanted to, if I were to create a new company, do something that would allow human flourishing. bring back authenticity in an age of ai. Like I knew I wanted to do something around there. and so when I got into Betaworks with Trove, I think was a good sign for me that, oh, you know what, I think there's really something here. Now going through the accelerator was actually, I had a rough time, just personally because as a solo founder, there was just so much to do and happy to share more about that. but I think now that I've graduated from the accelerator as of November. and have really built out and shipped a bunch of things. Actually heard user feedback. I think it really solidifies the fact that I am now on the right path to achieving all, like the things that I think we'll, we're gonna be able to do.

Varun Rajan 35:44

Yeah, that's great. just tell me a little bit about Trove, the whole like authenticity, maintaining that, like investing in that, in the age of ai. What does that mean to you? what does that mean to us, like individually? how is that informing the things that you're working on and, and what you care about?

Helen Huang 36:02

yeah, let me just give a one-liner or like a short blurb on Trove first.

Varun Rajan 36:06

Sure.

Helen Huang 36:07

so Trove is essentially a new way to understand your authentic self through what it is that you do and not. Just what it is that you say. So the way it works is that you'd play through these like daily interactive stories and based on your decisions, it's building up a character sheet of how you actually are. now the broader vision here is that this can become like a behavioral identity layer for the owner to own or like the user to own, and one that can be plugged into any system that they use. So like dating, hiring. Onboarding, ai, personalization, stuff like that. but for now, the main focus is really on the individual players, helping them gain knowledge and like just more awareness of their inner world, and just making sure that we're capturing that robustness and authenticity from them. So that's what Trove is.

Varun Rajan 36:58

That's awesome. one of the things I think I've seen from you, either in one of your job descriptions that you've put up,'cause I, I know you're hiring and honestly reading through them was actually super insightful to get a sense of what matters to you and, and, and what you're really aiming for here. but one of the things that stood out to me, and one of the things I kind of like pride myself on having been able to do with like, you know, career. Coaching clients that I've had in the past and just with people on a day to day is like helping people really understand themselves and the things that they want in ways that they haven't been able to articulate to themselves. It sounds like that's a little bit of what you're trying to do here.'cause I think one of the things I saw you write was like, we don't really understand ourselves. Like we have a lot of trouble communicating who we are to other people and signaling that, like whether it's in dating or whether it's in hiring, but like. That first step of us being able to like understand ourselves is also something that we don't necessarily achieve. Yeah.

Helen Huang 37:54

this is science. Like I'm not just saying this is actual science, is that we, it's really hard for any one of us to really understand our blind spots. Because how we are changes on a day to day, it changes based on our feelings that day. Did we eat, whatnot. but it's like we're too close to ourselves to really get an objective view. and we need to fully understand ourselves first before we can even express it to others.'cause there's like a two part problem. Do we know ourselves and then do we have the right language to explain ourselves in a way that others can receive appropriately? And I think most of the systems that we use today, including like some of these personality assessments, or like the profiles that we write or like the prompts on Hinge, most of that focuses on what it is that we say, right? Which is part of it. Part of who we are is what we say, but a big part of who we are is also what it is that we do, we could say a lot of things like, think about like the. A professor, like a politics professor who knows so much information about what democracy is like, but is that really what translates into their real life? Potentially not. So many of us have so much robustness of like information, but that's not actually how we behave. And it's not like our gut feel and it's not what we do. but to date none of the tools that we have really capture what it is that we do. to me, half of who we are. Shown through our actions is actually not being reviewed by any of us.

Varun Rajan 39:20

Hmm.

Helen Huang 39:20

think that's a part of our personality or our character or of our values that we should be able to look into and glean information from. And only when we have that can we be able to think about, okay, yeah, what is the right language to use? How do I present my authentic self to others? How do I consume it from other people as well?

Varun Rajan 39:38

tell me a little bit about you. You've had, like thousands of people go through, some trove games and stuff. Uh, tell me a little bit about like how many people have, uh, uh, have been through it, have played the games, and also tell me about how it's been received. like what are people getting out of it? what, how has that actually like, translated IRL into their, into their lives so far?

Helen Huang 39:58

so right now, just so you know, we're actually pre-product as well.

Varun Rajan 40:02

Okay,

Helen Huang 40:03

a few different demos, which are gonna be representative of the full campaign and like the actual experience, but. Each, so far, each of these have been like short term drops or

Varun Rajan 40:13

sure.

Helen Huang 40:14

time campaigns, for example. so the Valentine's Day one, we wanted to do a series of games called Tangles, by the way, in the trove universe,'cause you're untangling these like dilemmas and you're figuring out what to do with them. we had a two week campaign in February geared towards. scenario where you as a user are going on a third date with someone and there comes these issues. but the whole point is that at the end, as you play through multiple games in different instances, what are the patterns underneath all of your play? And what can we teach you that you might not have been aware of about your own dating style? So that was the goal of the game. and. I've always been a product person, right? And a lot of times, like product people don't do super good at marketing, and so I think I probably could have poured far more fuel on the fire from a marketing perspective. But that's why I was also so surprised because we had over 6,000 people visit. Site. we had to date now probably around 3000 players, but during the full end to end, it was, 2200 players that played through the entire thing. the entire thing is a seven minute experience, which if you also know how hard it is to even get a second of attention from people to, to have known that somebody sat down cold. Was like, oh, you know what? Let me do this thing. And it pulled them enough to let them complete a seven minute experience and then eventually log in. I think just, I was super happy with the stats, basically.

Varun Rajan 41:45

Yeah,

Helen Huang 41:46

and

Varun Rajan 41:46

incredible.

Helen Huang 41:47

anything about consumer stats, we had 77% day three retention, 34%, day eight retention, and there's no push notifications. So but, and that's just on the metrics. I think what was more exciting to me was the inbound emails.'cause I was getting, people were messaging me on LinkedIn being like, Hey, there's a bug here, can you fix it so I can finish the gameplay? and then people messaged me asking for their full transcript.'cause again, part of this, part of Trove is that. The data you create belongs to you. And I think that's a core ethos of the product as well. And so people were messaging in being like, Hey, I wanna read my play through again. and I was like, okay, sure, let me send it to you. But why? And they were like, oh, I wanna show it to my therapist because these are things that we discuss within therapy

Varun Rajan 42:32

That's wild.

Helen Huang 42:34

way of role play that I don't have to spend my therapy time doing. And I was like, you know what, here? that's awesome. That's true. we, I mean I also had an email from someone who broke up with their ex-girlfriend over the game.

Varun Rajan 42:48

Oh wow.

Helen Huang 42:49

like how they reacted, which again, was not part of what I was hoping to achieve. But I think that also speaks to. we all have such intense inner worlds that never gets pulled out because the right questions don't get asked. And so

Varun Rajan 43:04

Yeah.

Helen Huang 43:05

have a diverse range of questions that are asked, like what can we learn about each other and ourselves, and it's just so interesting. But that was a lot of the follow ups that I got from people. I also had some folks like play through just In a dumb way, trying to play the game, not really trying to react as they would. But then when they got to the end and they realized that, hey, this is learning about themselves and it's a profile about themselves and there's no game and there's no winning and there's no right answer. they emailed me in asking if I could erase their data so that they could replay it with how it is that they truly felt.

Varun Rajan 43:39

Huh.

Helen Huang 43:39

I think now, and that's also why I'm so excited because I think I mean, if we think about it, a resume has stayed the same format for the last a hundred years, right? And in tech we've now pivoted into having portfolios because it matters how people think about things. But with AI making all of what's written and even what's spoken sound perfect on paper, what is the result that's left, right? Like, how do we actually quantify. Our values and what we believe in and like how good of a communicator we are. And I think every person inside themselves does have a desire to showcase who they truly are. and there were comments just being sent in about the aspect of this like profile and knowing someone's character and seeing someone's character and how that could help in better matching, not just in relationships, friends, but also teams. I think. I think it really was reading the emails that came in, that got me more and more excited that, hey, I think we're on the path of doing something that is really gonna be positive for humanity, and in keeping like our human selves.

Varun Rajan 44:45

Yeah, that's incredible. there's a ton of stuff that I asked you, Helen, I'm just curious, like what's top of mind for you right now? what are the kinds of things that you're excited to do next, whether it's for, for Trove or, any new fashion shows that, that you're putting together? and what do you hope people. Take away from like, interacting with you. if you could kind of like leave a lesson with an, anybody that you talked to, if you were to like, leave a lesson or like, even like, I wish, more people would pay attention to X, y, or z. What, what would that be?

Helen Huang 45:16

I would say that one, no, no fashion shows planned in the future.

Varun Rajan 45:22

Okay.

Helen Huang 45:22

but I would say that if there was a fashion show, it would not be garbage bags, it would be corn stalks.

Varun Rajan 45:28

Ooh.

Helen Huang 45:29

if you think about the corn stalks that are left behind at, after, at the grocery store, after someone's pulled through all of the corn, hey, we can do, probably do something with that. Anyhow, I'll just put that aside. But if

Varun Rajan 45:40

Great.

Helen Huang 45:40

listening that wants me to, wants to help with that, lemme know. I think if there, there's so much things on my mind. Frankly. There's so much things. because right now I'm in the throes of hiring, like I am looking for a founding team, people who really believe in the mission, but also recognize how hard startups are gonna be. So that's happening. I'm also actually just kicking off my pre-seed fund rate. So speaking with a lot of investors and angels and like micro funds right now. so that's also happening. Again, I should probably focus, but I would say my superpower is actually just sheer execution. So I'm gonna get through it and we're gonna look back on this episode, Varun, you and I, and we're

Varun Rajan 46:20

Hell yeah.

Helen Huang 46:20

don't you Rema, don't you remember? And we're gonna cheers.

Varun Rajan 46:24

Yeah.

Helen Huang 46:24

happen. but I would say if there's anything that I want to leave, I think it's just remembering that the answers are within ourselves already. I've been speaking to a lot of students recently just because they're navigating the job search and oh, the first full-time job and. I, I think a lot of what is happening, especially with AI, is people feel like AI is giving them the right answer and that's what they should follow. But the truth is, AI is trained on a variety of previous documents and like things that have been written down, but even that, there's a lag in that, right? Because the most novel thoughts are probably in our minds and they're not written down, I think it's really re important to remember for everyone that you have the right answers for yourself already. yes, you can think and you can listen to anyone's advice on a podcast. You can read a book. But all of those are learnings that person has had for themselves, which is unique to their own situation. I think one of the things that during CoLab I really cared about was the aspect of a flipped classroom and not centering the instructor when it comes to a lecture, but rather centering their own learning. never think of a teacher as the. Yes, they can be a source of truth, right? But you have to do the work of crafting your own narratives and deciding on your own values. and it's the same thing with Trove. I think we're so used to us prompting ai, ai giving us the answer. And with Trove, what I really wanna do is, Hey, AI prompts us. We give the gut feel, we give the answers, and no matter what it is that we choose to do. There's gonna be some spark of individuality, and that's what we need to continue to develop within each person.

Varun Rajan 48:10

I love that. it's incredible. on that note, I did see one of your LinkedIn posts where I think you just had a, like a throwaway line here about like the people that had been applying already that, like, maybe you would think about like pairing them together or like, you know, let, letting applicants meet each other. Is that something that you were actually able to do?

Helen Huang 48:27

I really want to do it. I still really wanna do it. I think what is gonna end up happening is. Oh, Varun, I need people, I need a team.'cause trust me, the solo founder experience is, I love it. It's great, but it's also very rough. and I've had some really amazing people be able to help out with Trove, like on contract and stuff, but it really is time to bring on a team. But anyhow, to go back to your answer, I definitely wanna do that. first I need people to opt in, so I'm not gonna just randomly do

Varun Rajan 48:55

of course.

Helen Huang 48:56

I think I'm gonna message people back and be like, Hey, are you in? Are you interested? This is not gonna lead to a job. But it could lead to someone who, again, is so similar to you or so different in some unique way. And I think that was also the benefit of like really pouring my heart into this job app, like into the job

Varun Rajan 49:12

You really did. Yeah.

Helen Huang 49:14

because I think the people that responded gave me that same energy and time back, and I'm very grateful for that because I fundamentally believe that every business or like collection of people really, it's like a, it's a mutual fit and it's a mutual decision.

Varun Rajan 49:28

Yeah.

Helen Huang 49:29

I'm really grateful for all of the amazing apps. but because of that, I feel like I could do some interesting matching.

Varun Rajan 49:35

Yeah. Do you, do you have a, o obviously there's the kind of like consumer angle. You're getting people like involved and like playing games and like they're excited to learn more about themselves. Do you have a sense of the use case for which, it will be applied sooner rather than later? Like obviously maybe that's. Uh, down the line, you said you've been talking to hiring teams and stuff like that. There's the kind of like recruiting angle, there's the dating angle. you know, where, where are you most interested in, the results of Trove showing up in terms of applicability?

Helen Huang 50:05

I think with Trove, so the first goal really is gonna be like the first milestone really is gonna still be focusing on the individual user.

Varun Rajan 50:14

Yeah.

Helen Huang 50:15

and providing them both entertainment and self knowledge. and getting to the point where we have engaged players and their really giving their. Their inner world and that they trust trove as the place to do it. So that is the primary first goal. I think once we have that data, there's a lot that can be done with it. one thing that I should say outright to anyone listening is that I'm not interested in providing this information to ads. and I'm not interested in doing that. what I think is that this is, again, it's the concept of a resume, right? And a user owns their own resume. Okay, if a user wants to give it to their therapist, if they wanna plug it into chat GPT, if they wanna attach it to their resume, I think a user should be able to do that. what I am excited about is paving the ground for that. obviously coming from an ed tech future of work background, this thing that interests. To me the most really is disrupting this concept of job applications, candidate experience, fit for the company, and rethinking that entire process. But I also know that within that process, there's a lot of regulatory things as well, I think. I'm very aware of the roadblocks, but that would be the industry that I'm most excited about disrupting. But I also think that it will again, be based on the individual. I

Varun Rajan 51:33

Yeah.

Helen Huang 51:34

space is probably a little bit more, relevant, just as an immediate jump because on both sides there's value in bringing your authentic souls. if you care to do that, obviously, like if you're, maybe not so much if you're just looking for a hookup, but if you're looking for something that lasts, I think that's what matters. And so maybe the jump there is a little bit shorter. And so from a go to market perspective, that might actually be what comes next. But first and foremost, focusing on the consumer.

Varun Rajan 52:02

Cool. Um. Thank you, Helen. this is awesome, and also someone who's kind of like, education and future of work oriented. Obviously I'm eager to kind of like learn about how this stuff EE evolves, generally, but I think you gave us a, a, a really great breakdown on how you think about things and what the opportunities are here. and I know you kinda like left it with I kind of asked you about like, what would you leave for the audience a little bit before and then I had to dive into more questions.'cause there's just so many things that I. Love to just get your insights on, super, super, uh, loved having you on. Thank you for, for taking the time and sharing all of your thoughts with me and sharing your story with me too.

Helen Huang 52:39

No, thank you. Thank you for asking the right questions and pulling it out.

Varun Rajan 52:44

I appreciate it. something that really stayed with me after this conversation, is something Helen said near the end. She was describing what Trove is trying to do, and she put it this way. We're so used to prompting AI and obviously waiting for it to build stuff for us and do stuff for us, but also waiting for the answer from AI. And what she's building is really looking to invert that. AI prompts us, and we use our gut feel to give the answers. And I think that's one of the most interesting framings I've heard this year for what's actually at stake in this moment. Because the risk isn't just that AI might give us the wrong answers. That risk exists, but the real risk is that we stop being the ones with the answers at all, That we hand over our instincts and not just the task. Helen talks about self-understanding as a first step, not as a therapeutic exercise, but as something genuinely practical. And I find myself agreeing with that completely. When I think about what a career is, I think it's a series of outcomes that come from relationships. And relationships, real ones, whether personal or professional, require you first to develop a relationship with yourself. And that starts with you actually knowing who you are, what you value, how you operate, what you're willing to do and what you aren't willing to do. And if you don't have that clarity, you're just optimizing for the wrong things and wondering why it doesn't feel right, wondering why you're burning out, wondering why you're feeling disengaged or languishing. What struck me about Helen is that she doesn't just believe this intellectually. She spent her gap year living it. She followed sparks of curiosity without needing an OKR to justify them. She executed at the pace of her instincts, the fashion show, the civic tech experiment, all of it, not because she had a strategy, but because she trusted that moving toward the thing that lit her up and captured her interest in itself was the information that she needed to move forward. And then she built a company out of that conviction. She also has a perspective on AI that I really wanna hold onto, that approaching it from curiosity rather than fear isn't just healthier, it's more honest. The fear-based framing, and I think I'm annoying people with how often I'm bringing this up, but the fear-based framing, the permanent underclass, that jobs are going away. I'm not saying that those things are things that we should necessarily ignore or that aren't true, but what I am saying is that it tells you nothing useful or practical for what you should be doing in this moment. The curiosity framing opens a question instead of closing one. If this conversation landed for you, share it with someone who's trying to figure out who they are before they figure out what they wanna do. And I'll see you next week