Episode 09: Amy Yin
Amy Yin is the Founder and CEO of Office Together, which delivers manager empowerment and scheduling tools to realize the full potential of a flexible workplace and make hybrid work, work. In this episode, Amy walks us through her decision to drop out of Harvard to join a start-up, and why she ultimately went back to finish her degree. She shares insights on knowing when you have the right idea, how to de-risk early hires, being a first generation Chinese founder, and her approach to “conscious leadership.”
Conscious Leadership with Amy Yin
Episode 9: Show Notes [TRANSCRIPT BELOW]
This week we get together with Amy Yin, CEO and Founder of Office Together, a company that delivers manager empowerment and scheduling tools to achieve the full potential of a flexible workplace. We talk with Amy about her unique life experience and how it influenced her mindset and career. She describes how her parents raised her to have a CEO mindset and be comfortable with risk and how this differed from the upbringing of her peers who share her American-born Chinese identity. We hear from Amy about her decision to drop out of Harvard to pursue an opportunity to be part of a start-up with her professor in Paris, and why the opportunity was so valuable despite the company ultimately not succeeding. Next, we discuss Amy’s work experience at companies like Hired and Coinbase and how her experiences with working remotely prompted her to found her own company. Amy goes on to explain why she was determined to hire her friends, why she is proud of her choices, and how she maintains those relationships with clear boundaries and expectations. You’ll also hear how Amy nurtures creativity and inspiration in her daily life and why she is a big proponent of conscious leadership. Join us today for this inspiring conversation on what it means to start a company!
Key Points From This Episode:
● Get to know today’s guest Amy Yin, CEO and founder of Office Together.
● Amy’s company Office Together and how they are helping managers by selling empowerment and scheduling tools to run a hybrid office.
● How Amy started Office Together after being inspired by the quiet time inherent to lockdown measures and working from home.
● Amy’s upbringing and how it diverges from many of her peers who are also the children of immigrants.
● Why Amy’s parents raised her to take risks and have a CEO mindset and how that affected her education, career, and attitude towards risk.
● How Amy dropped out of Harvard to build a company and how her parents’ support was integral to that.
● Why this experience was hugely formative and positive, even though the company didn’t succeed.
● The Conscious Leadership framework and how it manifests in Amy’s attitude to work and life.
● Amy’s decision to hire many of her close friends and their experiences organizing other events together.
● What Amy has learned from working with friends like setting clear boundaries and expectations.
● Some of the ways that Amy encourages people to think outside of the box at social engagements.
● How Amy recognized the moment that she should start a company.
● Why it was difficult for Amy to leave her job at Coinbase and start her own company.
● Amy’s search for a co-founder and how she became a solo founder.
● How to determine whether you have a customer and whether something is worth building.
● How Amy used her connections to interview companies to test the viability of her product idea.
● How Amy nurtures creativity and inspiration in her daily life.
Tweetables:
“I find that when I approach things with more of an open mindset, with curiosity of, like, ‘How can I figure this out? How can I make this super fun?’ I’m enjoying myself more and I bring in more of the energy I want to feel around me.” — @yin_amy [0:12:02]
“The number one reason I quit my job at Coinbase was because I wanted to work with friends. I wanted to start a company with friends. I really felt I’ve been able to accomplish that.” — @yin_amy [0:16:39]
“It sounds really simple, but it was like agonizing for me to leave Coinbase. It took me a good three months of suffering before I had the guts to quit.” — @yin_amy [0:25:31]
“The question, when do you know it’s time to build? It’s when someone is willing to pay you. That was the moment we started building was when someone told us they would pay us for the software that didn’t exist.” — @yin_amy [00:30:32]
“I really zone out for the weekends. I know a lot of founders don’t necessarily do that, maybe take one day off, but for me, it’s like Saturday and Sunday are off. I totally checked out, offline. I look forward to my weekend.” — @yin_amy [0:35:16]
Links Mentioned in Today’s Episode:
EPISODE 09 [TRANSCRIPT]
[00:00:01] JU: This week, I’m joined by my friend Melissa Miranda who’s filling in for Mar.
[00:00:05] MM: Thanks for having me, Jeremy. I’m Melissa. I was a previous co-founder and I’m now leading product over at Facebook. It’s great to be here with you.
[00:00:15] JU: Let’s dive into our conversation. In this episode, we talked with Amy Yin, the CEO and founder of Office Together. We talked with Amy about her decision to drop out of Harvard as a student and how she decided to go back. We talked to her about how she de-risks, hiring her friends, how she discovered that she had the right idea, and how she frames her work as a game in order to engage in what she calls “conscious leadership”.
Maybe if you wouldn’t mind just for the sake of folks who may be listening later, it’s great to get to talk with you. I’d love to hear a little bit about Office Together as a business; what you do? What value do you bring to the world? How are you changing people’s lives? Then, I just want to tell you right now, the first question we’ve got to ask is, you said you have a funny life story and you’re outside of what’s considered “normal”. I’d love to hear more about that as a disclaimer.
[00:01:13] AY: Yeah. I’m the founder and CEO of Office Together. We’re helping businesses charge into the future of work. What we’ve all learned during the pandemic is that flexibility is one of the key perks and benefits you can offer to your top talent, but making part-time office schedules, coming to the office once or twice a week or month is a huge headache for managers and for folks to try to make an office feel a little bit less chaotic. We sell manager empowerment tools and scheduling tools to make hybrid just work out of the box. It’s a big trend. Right now, we’re still in this, like, pre-pandemic office case and we’re helping companies move to how they want to collaborate and maintain some in-person elements while giving all the flexibility of being, like, remote.
I started this company last year, because I was really inspired by being locked in my own bedroom. I was working at Coinbase at the time. I was an engineer. I really missed being in the office. By like being forced to work remotely, I realized how powerful it was, like learning how to have this quiet focus time, and that other people were having like that same aha moment across the world, because we’re all in this shared experience of the lockdown. Then I wanted to make sure that these moments of being able to get heads down work at home could persist post-pandemic and that we could transition to this new world, normal together.
Just a little bit of Office Together, your question was kind of like, what’s like a little bit of my life story and what makes me a little bit weird?
[00:02:43] JU: Yeah, you said, “I’m outside of what’s considered normal.” To me, that’s a super interesting teaser if you only meant it as a teaser. But why do you feel you’re outside of what’s considered normal?
[00:02:53] AY: Well, I think that one of the big things as I’ve consistently oriented my life around taking risks, and like pushing really hard. I think that that’s really different from how a lot of us were trained. I grew up as like a first foreign American – my parents are from China. A lot of my friends who are Chinese immigrants, they are told by their parents, “Become a doctor. Get a stable job. Start a family.” The thing my parents always told me growing up is, “We didn’t raise you to be an employee. We raised you to become a CEO. Go start your company. Go and take risk.”
Growing up, my mom emphasized that it was important for me to not do too many chores. She like told me, “Hey, Amy. I don’t want you to feel like your priority is like making the house look nice or domestic work. I want you to focus on your extracurriculars. Focus on school focus and focus on becoming a leader. I don’t want you to end up like me.” My mom like cleans the house for like three hours a day and like works full-time. That was like – the way I was raised was really different from a lot of like the other ABCs, like American-born Chinese that I was around.
[00:04:06] JU: Okay. I’ve got here – I mean, this is fascinating as a father of daughters, my head is spinning just thinking about that as a frame. We didn’t raise you to be an employee. We raised you to be a CEO. Can you comment on how that positioning affected your thinking about your career? I can imagine there’s – you use that phrase ABC. I haven’t heard that before. But I can imagine there’s some pressure on an individual who thinks their life calling is to become a doctor because their parents say it. Is there pressure associated with your life calling to become a CEO? Just talk about how that influenced your career trajectory and how you thought about making choices to leave your company for example and start Office Together.
[00:04:53] AY: Yeah, absolutely. Well, it showed up in a lot of different ways. Okay. My parents weren’t always aligned on this. On one hand, my mom like wanted me to like go for gold, but she’s a little bit more risk-averse. When I told her that I was switching my major to computer science while I was at Harvard as an undergrad, she told me, “Oh no! Your life is going to be so hard.” Like she’s so worried about me like pursuing a life as like a technical person, because she associates it with like not like a woman’s job and really difficult. But at the same time, she knew that it was important for me to work on something really hard. Whereas my dad was on the other side being like, “No, you have to have hard skills. [Inaudible 00:05:31] hard skills? Are you able to like build something? If you can’t build something, why are we sending you to college?” His emphasis was always on like gaining hard skills.
Another example was this of like, you ask like, “Oh! What does it mean to have your parents orient you towards entrepreneurship rather than being an employee?” I dropped out of college between my junior and senior year to start a company. I think most parents would have been like, “You’re doing what? You’re moving to Paris to work out of your professor’s basement, to work on an Internet of things idea that we don’t understand?” My parents were like celebrating. They are just like, “Amy, this is it. This is your manifest destiny. We are so proud of you.” They were so excited for me to go work out of my professor’s basement in Paris.
I think a lot of American-born Chinese or other people of immigrant backgrounds would have gotten a really different reaction, where they’re like, “Oh my God! Are you going to be able to pay the bills? How are you going to medical school?” I never got any of that from my parents. I think that makes such a big difference in how I think about risk reward. They’re kind of rewarding me to take risks.
[00:06:38] MM: Did it make it easier for your mom and your dad? Because your mom wanted to see you as a CEO. Did it make it easy to decide that, okay, you’re going to take this giant risk and drop out of school to do this? How did this experience pan out?
[00:06:53] AY: Yeah. My parents were a very – actually, the funny thing is, of that whole set up, the thing my dad was most worried about was me going to Paris and having harm to my physical safety. In his world, he’s like, “Amy, Europe is so dangerous. You’re going to get like mugged. This is like the worst mistake you could make.” He was all about me dropping out of school. But like the risk of living in Europe for him was like really intense. It’s kind of like [inaudible 00:07:20] like most people think Europe is very safe, especially Paris, but that’s just how my parents orient.
Yeah. You asked me, did it make it easier to make that decision? Absolutely. Knowing that I have like my parents’ support and care, like they were just like, “No. This is like the absolute right thing. We have a feeling in our gut. This is like what’s meant to be.” That company didn’t end up working out for me, but I gained some of the most amazing experiences in my life. Like I learned how to build my first mobile application. I was the only software engineer so I learned how to build so much technology from scratch, and be self-sufficient and be super scrappy. I knew that any day that I showed up, if I didn’t get something done, we wouldn’t make progress.
That is like an amazing feeling to have when you’re 20 years old, that you single-handedly are propelling forward this business because there’s only three of us in the whole business. That was a really great experience. I did end up realizing that I didn’t have quite as many technical skills as I needed to be a super successful technical founder. I did go back to school and graduate, then I went to Facebook after work. My parents had a mixed response to that. My mom on one hand was super proud because he’s like, “Oh! Facebook. I can like tell people about it. It’s a really awesome brand name.” Then on the other hand, my dad was like, “Well, you’re going to go to Facebook. When are you going to start a company?” That’s always the question for my parents. “When are you going to start your company?”
The context they’re coming from was in communist China. Very few employees have power. Power was centralized for the government. The most powerful people in like the CCP tend to like work for the Communist Party. The people who had the most freedom and autonomy were small business owners. For them, they’re not thinking of like high-tech startups. They’re thinking about like real estate, or Mom & Pop shop or like retail, things like that. But the way that you could set yourself free was by starting your own business in their minds.
[00:09:24] MM: Yeah. That’s amazing. It’s amazing to have that sort of support. I think one of the things that I personally tasted as a founder was that, starting a company is like running a marathon, except, you don’t ever really know when you’re going to reach the end. It could be 26 miles. It could be 2,600 miles. In that experience when you were in Paris, did you get a taste of the risk and the effort that it takes to get a company? And the fact that you’re not in control necessarily all the time, and if you did, how did you manage it?
[00:09:57] AY: In this set up, I was not the CEO. My professor was the CEO. He took care of a lot of things around like fundraising, making sure we had salaries. I never had to think for like burn rate and things like that. But I did have the taste of just autonomy, and like making stuff happen and being super scrappy. Especially working with hardware, it just has to be scrappy, because even getting and MVP out there is a lot. I would say that that experience of working with someone – my professor was a serial entrepreneur. It was really different than now, where I’m being like the CEO and founder, and I’m going out in like fund raising, and like really relying on my network to build the company.
That taste in Paris, it gave me a taste and like left me hungry without feeling exactly like what the experience I’m having as now. But to your analogy about the marathon, I love running so it feels really fun. This is the most fun job I’ve ever had, like I love being a CEO. It is new challenges every day, it’s super refreshing. The main thing for me is I have to like remember, it’s like a game I’m playing with like my career, and like my team, and like life. When I think about it that way, it’s still uplifting and so energizing.
[00:11:13] JU: Can you say more about that? You said, “I have to remind myself it’s a game.”
[00:11:18] AY: Yeah.
[00:11:19] JU: That’s very counterintuitive to me. Why do you remind yourself of that? Why do you feel that’s true? Maybe there’s two parts. Why do you think that’s true and what purpose does that mantra, that reminder have? What impact does it have on your outlook thinking team, et cetera?
[00:11:37] AY: I practice this framework. You might have heard of it, called the Conscious Leader. It’s called Conscious Leadership. They have like the concept of a line. From below the line, life is serious, like things are hard. There are problems. From above the line, I’m like open. I’m expansive. Everything feels like fun, or interesting, like another situation for me to figure out. I find that when I approach things with more of an open mindset, with curiosity of like, “How can I figure this out? How can I make this like super fun?” I’m enjoying myself more and like I bring in more of the energy I want to feel around me. It’s not true or not true, right? It’s one of those things where I create the universe I want to be in. The universe I want to create for myself is like, hey, this is like fun and we’re in this together. The outcome doesn’t matter. It’s about the journey.
[00:12:34] JU: Do you feel that’s an attitude that you’re able to transfer to others as well? Because one thing to remind yourself, this is a game. Do you feel like you’re able to kind of pass that game mentality onto others?
[00:12:46] AY: I mean, I think so. One of the things I’ve really done with my company is I’ve brought in a lot of my closest friends to work with me. For us, it kind of feels like a natural extension. I have a large very close friend group of – people think it’s weird. I have like 20 best friends, and we just like do a bunch of like great stuff together. We’ve always done all these major coordination events for our social level. It’s like, we’re coordinating, like we got to get a permit at Golden Gate Park, we’re going to set tables and we’re going to have like five different field events and there’s like three different teams. This is like the order and here is like the master of ceremonies. That applies to running a company. It’s either like we’re setting up games in Golden Gate Park or we’re building enterprise SaaS that makes companies move into the future of work. It all feels really similar, it’s just kind of the attitude that you bring to it.
I think that when I take things as more fun, and lighthearted and more from a place of curiosity, I bring that energy to the people around me. I think it makes more enjoyable to work together. This is not meant to be investment banking. This is meant to be, we’re here because we’re here to have a good time and build something really interesting.
[00:14:04] MM: Yeah. That’s amazing. It sounds like through this conscious leadership that you can actually inspire people and bring them along on this journey, and lead them through even though it could be risky and tumultuous at times for sure. Tell us a little bit more about what it’s like to work with friends. I think that a lot of people think that you should never mix business and pleasure. How does this play out at your company and how do you manage the friendships and [inaudible 00:14:29] business?
[00:14:30] AY: I don’t know how I would have started this company without relying on my friends. I guess like from early on, I’ve always made a point of like making really close friends with the people I worked with, whether that was at like Hired, or Coinbase or Facebook. Then I started angel investing and my friends, like three, four years ago. Then, fast forward now, I have a bunch of my friends on my cap table. Friends who are like, “Hey, Amy. We just really believe in you and we want to be a small part of your journey.” That’s kind of like of one small step. I’m like, “Well, take this money, assume it’s gone. Light it on fire. But yeah, I think you’re welcome to invest as long as you have that mindset.” I was trying to set really clear expectations. That’s really important, just maintaining really cool, clear expectations of boundaries.
Then two, working with friends, it’s definitely more intense. I have done a lot of contract to hire. Basically, I’ve worked with a bunch of different – about 60% of my company has been contract to hire, which his like, they work like part-time or as contractors and then we convert them to employees if we find there’s a mutual fit. There’s about like a 50% conversation rate, so a lot of people end up being contractors and then coming in full-time. You get some real-world taste of what it’s like to like work with me, so you kind of know exactly what you’re getting into. That helps like de-risk it. I guess another big part of it is separating like what’s going on at work with what’s going on personally. I know I don’t do this perfectly, like a party, I can help to talk about work because that’s like a really important part of who I am, and I wouldn’t want to like make these two different like parts of my life.
It’s really important for me that I don’t use my power as like a manager, or like a CEO to like ask my friends for social favors, like the people that work at my company. I do have to like walk the careful line there. But overall, I think it’s been like a super positive experience. I highly recommend. I say this now, we’re only a year in, so maybe you check back in with me like a year or two. We’ll see how it’s been. But so far, I don’t think I would have done it any other way. The number one reason I quit my job at Coinbase was because I wanted to work with friends. I want to start a company with friends. I really felt I’ve been able to accomplish that.
[00:16:47] MM: Amy, was it just that your friends happen to have the skillset that you needed to start this company or is it –
[00:16:58] AY: My friends are so freaking talented. It’s just amazing. I think there’s something magical about being in the Bay Area. But yeah, – I did a dinner the other day with some of my friends. I think it was something like, ten of my friends I invited and there were people that just like were like my friends through social party, et cetera. Over 10 or 20 of them had become founders in the last year or two. That’s just kind of like the nature being at the Bay Area. My like friends I just like used to go and have wine with are now starting companies. There’s definitely like a density of talent that I’ve been lucky to tap into. But then yeah, I think that being in the Bay Area, your friends happen to be like designers at Google, or engineers at Facebook or amazing like this or that. More than anything, there are people who are super smart and whatever you throw at them, they just figure it out.
[00:17:49] JU: Tell us about the dinnertime conversation. Because one of the things that I’m – part of my nerdiness is, I really admire Ben Franklin’s practice of – he had a Junto, it’s what he called it, which as a weekly gathering, a leather aprons club of folks from different walks of life and different industries. Not inside his company but outside. He met with these people every week for 30 years. He’s just kind of amazing. He had rules of engagement. For example, has someone moved to Philadelphia whom we should know about? is the question. Has someone’s business fallen into ill repute and does anyone know why? Are there any scientific discoveries?
That’s kind of an extreme example, but I’m often thinking about what are the rules of engagement in a social interaction that has a potential to spark imaginations and creativity. Is it a free-for-all? By the way, that’s not a bad thing. It could be great. But all that said, I’d be curious to hear. You said, “I got a dinner with 10 or 20 of my friends who become founders.” How does conversation go? Is there any kind of structure? Is there any kind of – how do you think about that?
[00:19:04] AY: Yeah. I guess I’m a little bit more chaotic about it, but I am really intentional about bringing people together on a regular basis. Two or three of the companies that I’ve angel invested in; I introduced the founders to each other. They just like happened to meet through like me bringing people together. With the specific dinner I had on Wednesday, the exercise we did is we had everyone turned to a person next to them that they didn’t know. Then they swapped life stories, and then the one person had to pitch the person they had just matched to the rest of the group. It kind of like flips the introduction model on their head. I try to do things like that where we invite people to be a little bit more creative or out-of-the-box with how we do different social engagements.
I guess the second thing I would say is that I make it a point to talk about work. I talk about work with my friends and I always ask about it. I think some people are trying to like stray away with it, but I found so many like amazing synergies through that, like one of my portfolio companies, I introduced them to three of their first five customers. Just because people are always like talking to me about stuff, I’ve been able to connect people, like get them place at companies or introduce them to investors and like whatnot. I always make a point to ask people what’s top of mind for their business and I tell them what’s top of mind for my business, because then often, it can be helpful to me.
I guess those are two things. It’s just intentionally bringing my most talented friends together. They’re just my friends actually, but they’re my most talented friends too. Then making a point to talk about work and like what ask they might have or what ask I have.
[00:20:40] JU: That’s really cool. I love it. I kind of want to shift gears for a minute if you’re okay with that. I’d love to go back in your life story so to speak. You told us about when you got a job with Facebook, your mom was excited because it’s a brand name and your dad, I’m just scrolling up in my notes here, “When are you going to start your company?” I’d love for you to walk through from your job at – I don’t need like the career progression necessarily, but my question is, knowing that that was always on your mind – I think for some people, it’s not even on their mind to start a company. It’s like not even on the radar. For you, it seems like it’s always been on the radar. But what were the signals that you were monitoring a year ago when you said, “I realized I’m sitting in my room and I value downtime.” Would you walk us through how did you decide it’s time to start? My destiny has culminated so to speak, to put words in your mouth. Walk us through how you knew now is the time.
[00:21:42] AY: Yeah. I wish it were a little bit more scientific from that, but I would say, worked at Facebook, worked at Hired, got really excited about crypto, left Hired, took a pay cut to join Coinbase. Like was on this like amazing journey with Coinbase. A lot of like ups and downs. Then I got to a place at Coinbase where I realized that we had ballooned in size, which is a great problem to have. But we have gone from like 100 people to like 1200 people. I realized like I just didn’t love being at a big company anymore. I started interviewing for new jobs at other startups. Then by talking to other startup founders, I just kind of realized that they weren’t more qualified than I was to start a company, but they’re getting a lot more upside than I was by being an early employee versus the founder.
If I wanted to work at an early-stage company, why not my own. It happened like pretty organically. I went from like being like, “Dad, I’m not read to start a company. Dad, I’m not doing this. Dad, I’m trying to like find a boyfriend. Dad, I don’t have time. I’ll start a company when I’m ready to. Right now, I just don’t want to.” Kind of like within like a month or two being like, “Actually, dad. I’m starting to figure out when I’m going to start. Like I want to start my own company.” My parents did a very good job. They were just always he I was playing at my subconscious layer. It felt like it happened very effortlessly.
Being not an entrepreneur, it felt like me trying to avoid the default and that like kind of the natural state was to like progress back to entrepreneurship. Because I was always starting stuff. always like starting new groups and doing – always like initiating like things. Starting a company, when it happened, it didn’t actually feel like effortful. It just happened because it – it felt like all these pieces just like fell into place. Like I had all these great technical skills. I like was out of place where I felt like ready to leave Coinbase. I had like all this great support, my like romantic and like social life kind of like stabilized and it got to like a really great place.
I have done a lot of self-work, like working with like a coach for a few years while I was at Coinbase that like introduced me to conscious leadership. Her name is Samira, she’s like amazing. Then she helped me like realize that I can like live in my full magnificence at Coinbase or I could do it by starting my own thing and the latter felt way more appealing to me.
[00:24:08] MM: Amy, tell us what came first? Was it the desire to start a company of your own or this particular idea for Office Together?
[00:24:19] AY: It was definitely the desire. I wanted the experience of building up a team, working with friends and just learning a bunch of stuff all at once. I iterated on a few different ideas. The first I had worked on; I did like a bit of a co-founder shopping. I had like worked on some other people startups for a bit, that didn’t like work out. It’s just like wasn’t a good co-founder match. Then after I – this was like the third idea I like seriously iterated on. It came from like, “Oh! I actually feel like this future of work thing.” Work is changing as we know it, and it’s going to need a whole new set of tools to go along with it. Started just like interviewing – I interviewed like 40 or 50 HR leaders and like folks in the space, realized that their companies wanted to take a totally dramatic shift in how they viewed in-person collaboration. Started like mocking up and working on a few different slide decks for like what features mattered to them.
Within like maybe like eight weeks or so, I had my first two customers lined up before I even had a product. I hadn’t written like a line of code. I was like, “Okay. This people like want to buy something from me, I think it’s time. This is go time.” It sounds really simple, but it was like agonizing for me to leave Coinbase. It took me like a good like three months of like suffering, before I had the guts to quit. I tell it like it was super simple, but at the time, I was like, “Oh my God! Should I leave? I’m going to be salary-less. I don’t know how long I would go without a paycheck.’ Really, really agonized about it until like I was like, “Oh my God! I’m tired of agonizing about this. Let’s just pull the plug.” I finally did it and it felt really good. It was like such a huge sense of relief once I finally told them I was like leaving. Coinbase had been a home for a while.
[00:26:08] JU: How did you know it’s time. I mean, I want to dig into that because you’re saying, “I don’t have a salary.” It sounds like you had maybe a couple customers lined up. Walk us through that like what gave you the confidence to say, “You know what.” Because you said agonizing. I mean, that’s a really – it doesn’t sound like it was easy. How did you know or I mean, you may not know it’s right, but what gave you the impression that you said, you know what, it’s worth at least exploring and in a more – I got to cut the cord. I’m going to stop my paycheck. What enabled you to – it if not even with confidence just make the decision.
[00:26:47] AY: Yeah. That’s a great question. I got to the point where I was working like over 100 hours a week, because I was working for Coinbase full-time while working on my own company full-time. It became like physically unbearable to work like – I was actually working three jobs at the time, because I started a conscious leadership coaching practice, working on Coinbase as an engineer at night and then during the day time, I was doing all these customer interviews for what would become Office Together.
It became like logistically impossible to juggle all three of these at once. That was one part of it. The second part of it is I just like was not looking forward to my job at Coinbase at all. Like I was delivering and like having amazing outcomes, so like I was doing like a growth team, like really helping boost the company’s revenue, but it wasn’t getting me excited. Like I was not looking forward to any of the stuff I was doing at work. That’s like, it has nothing to do with Coinbase and everything to do with like whether I was.
I think that was getting to that point of just being like, “Oh my God! Like doing this again is going to suck my soul out. I’m too young to have my soul sucked out. I’m too young for that.” I was just really not happy being just a cog in the corporate wheel, which is what how it felt being at that big of a company. The company had also never done remote before. They really didn’t know how to engage employees remotely. I think that that was a combination of just – like this actually what I advise a lot of entrepreneurs who are like – or people who are like – or people who are working jobs, they’re like, “When do I quit?” I was like, “When you literally cannot do your job anymore?” That’s the point I got to.
[00:28:28] MM: Amy, you mentioned co-founder shopping. Did you shop for your founder for Office Together? Did you find them before you left?
[00:28:38] AY: I’m actually a solo founder. Unsuccessfully co-founder shop. I worked with a few different co-founders. I had met some through On Deck, which is this like fellowship for founders. Then I’d met – I talked to some people who I’m like really close friends with. Nothing felt like the right fit, like I felt like with each of these co-founders. I had spent a month each working with them. I just really believe that I can move faster alone than with someone. Which is not the right like – that’s not just the right partnership then. All three of these people are starting their own companies and doing fabulously well, but it just wasn’t the right chemistry for me.
I just realized that the time was now, like if I didn’t get on this, I would be behind. The future of work wasn’t going to wait for me. I just decided, okay. I’m just going to do it on my own, fund raise, start the company and built the team. In ways, it’s like, “Oh man! It’d be nice to have a co-founder.” But in other ways, I’m like, “Oh wow! I am more powerful than I even realized.”
[00:29:37] JU: That’s fascinating. I love the future of work wasn’t going to wait for me. I think that’s a great – there’s a sense of timing, a sense of moment there.
[00:29:46] AY: Urgency, yeah.
[00:29:47] JU: I’d love to hear about customer interviews. That’s certainly a part of the process we advocate at the d.school. We often say, never build something you haven’t sold. But that is a radical reframe for a lot of people. Can you talk about being in these interviews, putting features that you haven’t built on slides? It’s like second nature to some people and it’s like unfathomable to others. If you’re going to just give like one or two-minute crash course in, how do you determine whether you have a customer or how do you determine whether something is worth building? What did you do? How did you think about that? How did you know when, “You know what, I got to start building now?”
[00:30:32] AY: The question, when do you know it’s time to build? It’s when someone is willing to pay you. That was the moment we started building was when someone told us they would pay us for the software that didn’t exist. What we did, it was me and then the person who became my first employee who’s like a designer at Google, super talented, one of closest friends, Becca. Becca and I were like living at this house together for a week in SoCal. I was like, “Hey! I just quit my job and I could kind of use in helping with the design side.” She’s like, “Yeah. I love to get involved.”
I like basically wrote down a few words and each word represented like a feature. I was like, “Well, here are the words I keep hearing.” Let’s pick three of them and I’m just going to go pitch it.” I just had her like mock up the simplest thing for each one. It was something like calendar, like desk health checks. Something like that. Very, very simple. I just put these three things on the slides and then I just like went through and started selling it to people, being like, “Hey! It sounds like you might have this problem. Do you have this problem?”
We just kept going at it for like maybe like six weeks and tell customers like, “Wait! We actually need this thing like right away. We’ll pay you money for it.” I was like, “Okay. Great. Let’s do it.” It’s actually not that hard. I would just like make a really sort slide deck. B2B customers are really used to buying a slide deck. Most customers will buy something without ever touching your software. We never lied about it. They knew exactly where we were in the feature development and whatnot. It just solved a novel problem for them.
[00:32:05] MM: Amy, it sounds like getting these yes answer, so I want to buy it from your deck was super important for you to know that this was the right thing to build. How did you find people to interview?
[00:32:17] AY: I just reached out to my friends and was like, “Hey! I noticed you’re working at like X, Y, Z company. Can you introduce me to your HR leader? It just like holds – I just did that with a bunch of my friends. I started like maybe 40 or 50 phone calls that way, just the – that’s it. There’s no secret to it other than, you just got to like prospect and outbound and set up a bunch of calls.
[00:32:39] JU: I feel like this conversation could continue for two hours. I mean, it’s amazing. I love how thoughtful you have been about your journey and I love hearing how your personal life and your work life are largely integrated. Can you talk for a moment? Maybe [inaudible 00:32:59] from work, but what I want to hear about maybe in the last piece of our conversation here is, tell me about how you stay inspired, how you stay invigorated, how you preserve space for divergent thinking. You mentioned space for heads down work, and remote work being a good opportunity. I would say, in a way, I have less space for heads down work because everybody can book another meeting and I’m like – it’s like I end one meeting and the next person goes, “Hey!” And I go, “Oh! I didn’t even have a chance to write down my thoughts.”
It seems like that’s important to you. I don’t mean to project, but talk to me about nurturing your own thinking and creativity, and inspiration.
[00:33:42] AY: Let’s see here. A few things. One, as I do no meeting Wednesdays. It’s something that Coinbase did and have stuck with me. If I take a meeting, it’s only because it’s last minute or like urgent, but it gives me a day to actually do heads down work, get to like my to-do list and just have some like time to link space.
Obviously, the very stereotypical Silicon Valley answers. I definitely meditate twice a day. That’s like a generic thing that every founder is going to tell you they do. Because they’re not going to go on public radio or whatever and say they don’t meditate because it’s not good for their business or whatever the investors are hearing. Meditating twice a day, very important. I also – I’m very extroverted. I do my best thinking when talking to people. I participate in like different like founders’ groups and like coaching circles because I get so much like from like the back and forth bouncing ideas when people are hearing other people talk about their problems. Other people making space for me.
Even though I am like so, so busy, I still make time to go to regular founders’ groups and sessions. This morning, I went to like a coaching group for sales founders like working on sales. It was like one of the highest impact things I did in a week. These kinds of things, they don’t feel urgent, but they’re like really, really important for the long-term, is just making space for personal development. Yeah, I would say I do that and then I don’t work on weekends. I turn of my computer, check my email and I really zone out for the weekends. I know a lot of founders don’t necessarily do that. Maybe like take one day off. But for me, it’s like Saturday and Sunday are off. Like a totally checked out, offline. I look forward to my weekend. You guys are one of my last calls for the day. I’m like so excited for my weekend because I know that I get to totally reach out. I mean, we can feel so alone when I don’t have like to work, that I feel so refreshed on Monday and ready to go.
[00:35:43] JU: That’s incredible. That’s an incredible discipline and I admire it. I wish you all the best of luck and if there’s anything I can do to make instructions or support you in any way, I mean, I would love to. But Amy, it’s an incredible pleasure to get to meet you and learn from you. You’re right, you do have a fantastically interesting, unique story, but I think one that people absolutely can and should learn from. Thanks for your time.
[00:36:12] AY: Of course.
[END]
The fine folks over at Section recently interviewed me about some common mistakes I’m seeing folks make when they use AI. One of the biggest ones? The tendency to expect too little, and get just that.