Ambika Singh - Armoire CEO & Co-Founder
00:00:00“Does anyone know who this girl is?” Then I went out to raise money. And everyone was like, “Great pitch! So is this a real company?” I was like, “Yes! Didn’t you hear me on the stage?” And they’re like, “Yeah that’s cute… Next!” I was like, “Duh!”
00:00:24 Ash Faraj:Hey! Welcome to the ExecuTalks Podcast. It’s the show that gives you insight to the personal stories of today’s top executives. In this episode, you will hear from Ambika Singh, also known as Bika. She is the current CEO and Co-founder of Armoire, a clothing rental company with a modern-day boss lady. She successfully raised over $5 million, has over 75 employees, and the company is on its way to disrupting the entire retail market.
00:01:06 Ash Faraj:Bika was born and raised in Bellevue, Washington, and was extremely talkative throughout her whole childhood. She was part of the first class to graduate from the International Community School and there she would become the ASB President and get her first “Start-Up” experience.
00:01:26 Ash Faraj:Speaking of your childhood, if I was in a classroom with you in high school, who is Ambika Singh?
00:01:31 Ambika:Probably annoyingly chatty. I remember in seventh grade, my history teacher picked up my whole -- we had like those desks where the chairs connected to the desk. Remember those? -- he picked me and my desk up and moved me into the hallway. [laughter] That probably would be illegal now. He was like, “Enough talking. Enough.” [laughter]
00:01:57 Ash Faraj:I thought I read somewhere you were like the ASB President of your high school?
00:02:01 Ambika:Wow, you really went deep there. [laughter] I was the ASB President of my high school which was a really interesting place. It was my first start-up experience. Yeah. It’s called International Community School. I’m very proud of it. It persists. There’s one in Kirkland and one in Bellevue. I was the first class to graduate all the way through. So when we started, we were in the six porta cabins on the Redmond High School campus. There were 37 of us, or something like that, across two grades. Seventh and eighth graders on a high school campus, and we’re already this nerdy, super weird group of kids. They amazingly scheduled it so that we had the break at the same time as the high school kids. It was a complete disaster. [laughter] I luckily avoided this, but a lot of the kids had those rolling backpacks and the high school football players would come by and kick the backpack out. The kid and the bag would go flying. It was like a nightmare! I don’t know who decided that, but this was never going to be a great idea. But we adjusted like all start-ups. They changed the times of the breaks, so that we only went to the bathroom when the high school kids were safely in their classrooms. But it really was an amazing experience. We built it. I felt like we all had a part in it. There was a philosophy at the school; one-third students, one-third parents, and one-third teachers. So everyone had sort of a responsibility and a voice in making it successful. I really do think those were core lessons that I learned at a really early age about how, you know, you make a mistake and a kid goes flying because they get kicked by a high school kid and you adjust. You’re like, “Oops. That didn’t work very well.” Now the mistakes we make are -- less sort of impact people’s bodily harm -- less acutely. But those are real lessons that I think…
00:03:56 Ash Faraj:Did you have a plan after high school?
00:03:58 Ambika:I was pretty ambitious, always. One is to go to the best school I could get into to.
00:04:04 Ash Faraj:Was there a specific school that you wanted to get into?
00:04:06 Ambika:I really wanted to get into Stanford. I didn’t get in. I remember my dad walking me around the backyard of his house as I like bawled. He was like --
00:04:19 Male Voice 1:-- You thought it was the end of the world, huh?
00:04:21 Ambika:[laughter] Yes, totally.
00:04:23 Ambika-- “You’ll survive.” But at the time I couldn’t see that. It really felt catastrophic. I think that that is one of the amazing gifts that my parents have given me and continue to, and the people who are close to me, is like the gift of perspective. Because when you’re in it, things feel really up and down. The wins feel really big and the losses feel really catastrophic. But people outside of you care about you and can often give you perspective that you can’t necessarily see yourself. This thing is a thing that you wanted, and you’ll find another thing that you want.
00:05:08 Ash Faraj:I’m sure you’ve had the feeling before where you’re not unhappy, but at the same time you don’t feel like you’re doing something that’s important enough. Or in other words, you feel insignificant relative to what other people around you are achieving. When Bika graduated college, she went to work for Microsoft for almost three years. Towards the end of her time at Microsoft there was a point in time when she felt sad and insignificant.
00:05:38 Ambika:… passed on them and create solutions that were really viable. So anyways, long story short, it was an incredibly inspiring job, great manager, great small team (there were just five of us.) I really loved my job. I don’t remember at that moment thinking about doing other stuff, but I think at that stage in my career I was like too many people around. I remember thinking [laughter] at the end of the day if I died in my office, no-one would notice for a few days. That was like my visualization. I was like I’m so redundant. What am I doing? [laughter] I think there’s phases and times and so that’s when I really started to think about it. How do I create a place where I feel impactful?
00:06:24 Ash Faraj:After coming to the realization that she needed to find a place where she could be more impactful, Bika simply started engaging in conversations with other people and found a start-up she was interested in working for.
00:06:39 Male Voice 1:What did you do when you felt that way? You’re like, okay, I need to just get out of here or did you actually put a plan together? What was that process like?
00:06:49 Ambika:I think I started to like, ears open, eyes open; so started to talk to people outside of Microsoft to figure out what other people are doing, what kind of things were exciting. Really, I think I continued to solve problems by talking. I guess this is the seventh-grade problem. [laughter] A lot of the times when I’m talking, I’m trying to work out my own feelings and what I want to do and that kind of stuff. So talking to people has always been a successful tool for me in that way. I think that’s what I started doing. That’s how I eventually found my start-up experience that I ended moving out to.
00:07:29 Male Voice 1:What were some of the companies, the earlier ideas that you had?
00:07:32 Ambika:At that point I don’t specifically remember thinking about me being the leader of them. I was just looking at small companies that existed.
00:07:41 Ash Faraj:I’m not sure if it was our discussion or I read it somewhere online, but I think you had left Microsoft to start a company or something and it didn’t work out. You came back to Microsoft?
00:07:52 Ambika:I didn’t start it, but yes, the company at the time was called TravelPost and became Trover. It was started by Rich Barton and Greg Slyngstad. Greg Slyngstad was the first Expedia CEO when it was still inside of Microsoft. When they spun it out Rich became the CEO, and then like a couple of other really early Expedia employees. So it was a very exciting…The headline was “The band is back together.” They raised a bunch of money. I came in with a cadre of about like five other younger, more junior folks. We had a blast for a year, but we never really crystalized on what exactly we were building. After a year, they really downsized the team down to two engineers from seventeen people. So it was a pretty jarring… It was the first time I’d ever been fired. I guess I got laid off. I still don’t really know the difference between those two. Whatever it was, they were like, “You’re done.” I was like, “Ah! But this is my home!” So it was a very… Yeah, it was painful, heartbreaking really.
00:09:11 Ash Faraj:If you could point to maybe two things why that start-up, that company, failed. What were those two?
00:09:18 Ambika:I think we weren’t able to crystalize on what we were building. The idea was that we would sort of like innovate in the travel space. Particularly those guys that had the experience of building Expedia. We really felt like -- and I still think this product should exist -- you really felt like there was a gap around recommendations and reviews and even content creations on the individual level. This is all in the context of travel in a way that is youthful and consumable back to the content creator themselves. Some of the scenarios we talked about were like, “If I go to Guatemala, how do I plan my trip? And then how do I save my trip? And then how do I share my trip and the parts of that that are interesting and important? I still think that that solution is not stitched together well. Right now, we do it through Instagram, and maybe we solicit advice from Facebook, and we use TripAdvisor for reviews and Yelp, and Instagram for inspiration, but it’s all very sort of fractured. The save and share side I also feel is incredibly fractured. I have these bizarre google docs that I’ve tried to keep up to date because I’ve been very lucky to travel. When people ask, sometimes I’ll share them, but they’re super inefficient. So anyways, we couldn’t quite crystallize on what the vision was in all of that and chunk it out in a way that allowed us to start to build.
00:10:57 Male Voice 1:You were at the start-up. You kind of got let go. You’re devastated. What’s next?
00:11:04 Ambika:I went on a spirit quest.
00:11:06 Male Voice 1:Spirit quest?
00:11:07 Ambika:Yeah. [laughter] I was telling somebody else this story and she’s scolding me for being such a millennial. I had convinced my still very good friend and very early Armoire customer -- so again these people come back around -- so I had convinced her. She was at Microsoft with me, and I convinced her to come over and do this exciting start-up. Not only now have I convinced my friend, we both have no jobs. We’re both like sitting there, like holding the bag just staring each other. So we decided we would go on this spirit quest.
00:11:37 Male Voice 1:Were you married at the time?
00:11:39Ambika:No. So we got in her car or my car. I can’t remember. I think we kind of had a plan, but not really and just drove away. [laughter] We drove south where the sun is. We ended up staying in these crazy places in the middle of the redwood forest or we’re eating like cheese sticks from the gas station; it wasn’t that glam. We didn’t have that much money, so it was like it was very ‘unglam’. But then eventually we got to San Francisco. Her brother lived there. He had a real apartment and real job. We’re like, “Oh, this is nice.” Now this allure of a spirit quest is already starting to wane. [laughter] So we made like a little further south. I think we got to like LA or something. Okay, we’re like basically out of money. We’re done. I think we had the idea that we should write -- and I do regret this -- that we should write it down; like what we have learned. The turmoil, and the heartbreak, and like maybe what we could have avoided, or what we couldn’t see at the time, and blah, blah, blah.
00:12:45Ash Faraj:You said heartbreak. What was like the heartbreak? Was there a heartbreak you went through?
00:12:50Ambika:It was like an amazing, I guess… And probably all entrepreneurs or small company people go through this at some point. The first one it’s like you’re first love. Like you’d be at lunch together every day. We were really excited about what we were building. We hung out every weekend. We were very like all in. For it to all go up in a second, that’s the way I perceived it because I wasn’t privy to the fact that the thing wasn’t working. In my view it was sort of like we were doing great. It was very heartbreaking. I felt like something had died. I think what is likely is that given some distance it probably also made me, not tougher but less afraid because it was heartbreaking. And then it was fine because it’s actually not a person. It’s a thing that you built and you love, but it’s not a person. I felt like something had died, but it didn’t. I guess the fear around failure. Really, I learned a good lesson there; which is even in the worst case, you take a swing, you do the best you can, you meet some lovely humans who hopefully you take with you, and if it doesn’t work, it doesn’t work.
00:14:11Ash Faraj:Up until now, you’ve heard a little about Ambika’s childhood, her experience after college, and some lessons she learned along the way. After being out of school for seven years, she decided to move to Boston and attend MIT for an MBA and would go on to start Armoire during her last month in school. Before she graduated, she had a very generous offer from the Boston Consulting Group that even she admitted was so much it was hard to turn down. Ultimately, she decided that she was going to follow her heart and focus on building Armoire.
00:14:51Ash Faraj:So your father is a serial entrepreneur. After he had started a bunch of businesses, he started this family investment firm from what I’ve read. When you first started your business after your MBA, did your father offer to pay you money to invest?
00:15:13Ambika:He offered; not pay me money, but invest in the business. Yes.
00:15:16Ash Faraj:Did you take it?
00:15:18Ambika:I did not originally. I wanted conviction from outside that this was an investable business. I wanted to personally have conviction that this was something the market was interested in. I think I also wanted to stand on my own two feet. It’s a scary place to be, right? Taking anybody’s money is very scary. Especially, you know what it took for the other person to accumulate that wealth. I personally don’t know anyone who had money just fell on them from the sky. Everybody’s hustled for this, and you are saying, I think I can take that capital and turn it into more. That’s the conversation with your investors, right? There’s obviously a lot of conflicting emotions in that. Yes, of course, I believe. My belief is fortified by results, so I know that we can create value. But am I deathly afraid? Of course. Because there are things that I can see and things I can control, and there are things that I cannot see and cannot control. There’s some elements of risk in all of this. As the CEO and the Founder and the Fundraiser, you are the conduit of that sort of transparency or the explanation of that risk. It’s your job to be both utmost factual and transparent and honest, but at the same time convey a level of confidence. Because if you’re just sort of like all about the doom and gloom, nobody’s really excited to invest in your business at that stage. So it’s an interesting kind of push and pull.
00:17:15Ash Faraj:How did you go about initially raising money after you rejected your father’s money? How did you go about raising money from angel investors and did you have initial success?
00:17:24Ambika:It was very painful. [laughter] So I started in Boston. I’ve told this story before, so you may have found this in your extensive research which I’m very proud of; I mean very impressed by. I kind of came out of the Accelerator. The Demo Day video that you saw was the end. There were a bunch of investors in the room. That auditorium is like a 2,000-person auditorium. It was packed. I’d certainly never stood on a stage that big and the pitch went well. I sort of came out really feeling like a hero. I was like, “Oh, man. Does anyone know who this girl is?” Then I went out to raise money, and everyone was like, “Great pitch! So is this a real company?” I was like, “Yes! Didn’t you hear me on the stage?” And they’re like, “Yeah that’s cute… Next!” I was like, “Dah!” It was a really painful kind of awakening, just from like -- I think this is also an amazing start-up lesson that I heard early on. One of the things about start-ups is that you climb the mountains, literally daily, and you fall off either side daily. It doesn’t matter how big that mountain is that you either had to get up or that you fell down. So I was like on top of the world and then I fell off the other side and it hurt all the way down. It was painful.
00:19:00Ash Faraj:Obviously like 98% of investors are male, right? Is there a point in time when you’re pitching to the male investors and what tactic did you use when they said no or you kind of hit a wall with that?
00:19:11Ambika:Is that over? You’re saying that like it’s in the past tense.
00:19:16Male Voice 1:[laughter] It’s still the same. It’s still going on.
00:19:18Ambika:[laughter] I’m still in that. But what was like tactics to move the conversation forward? I’m still learning. One of the problems with this this is a difficult business. I mean all businesses are difficult, but this one is retail. Depending on how deep you’ve been following the news on retail. Barneys went out of business this year, Macy’s is having a tough time, Forever 21 went out of business. There’s a long list.
00:19:56Ash Faraj:Dennis, wasn’t there a story we were talking about where she had gone to the investors’ wives to pitch them instead of going to the investors?
00:20:07Male Voice 1:[laughter] That was genius. That was pretty smart. They all rejected you, so you went… that’s really smart.
00:20:13Ambika:Well, that’s a strategy that I would like to learn how to execute better. Because what often happens is that they will say to me, “You know I really don’t understand this, but I’m going to ask my wife.” But what happens then is they get some watered-down version. You know, you guys are in the entrepreneurial space. You know how important a pitch is and the cadence. We practice every slide and the delivery and the passion and all this stuff. And they get some version, “This woman came by. She wants to do something with clothes. Do you like clothes? Do you think I should invest in the business?” “I don’t know honey. We’re late.” I’m not even in that conversation! So I did try to start figuring out how to be in that room when that conversation happens.
00:20:57Male Voice 1:How did you?
00:20:59Ambika:Going directly to them. So our cap table for a long time was nearly 50% women, and a lot of them had never written a check before. Many of them have last names with husbands of people you might recognize, so a lot of operators in town. A lot of investors, but for their wives they understood this business. Sometimes it was their daughters. And they really got it. Either they wrote the check, or they pushed dad or husband to write the check. To me that’s a perfect example of how the table and the companies that we fund would look different if we had a different group of investors sitting around the table. So yeah, wives, girlfriends, daughters, all my friends. All of them. Got to go find them. Yeah, it’s a hustle man.
00:22:00Ash Faraj:Have you ever told yourself, “Once I get successful, I will be so much less stressed out,” or “Once I grow my company to $10 million it will be so much easier from there.” Well it turns out for Bika, the stress levels actually increase and other, more difficult, challenges begin to arise.
00:22:23Ambika:Fighting fear is a big thing, and success begets different problems. Today, I worry a lot about the fact that we have 75 amazing humans who I care deeply about. I want to keep paying them, forever. As long as they’ll stay. I want to have the ability to do that. I want to build careers for them that are worthy of them. A lot of these people now have put in two, three years of their lives into a dream that we all believe in. I want to make good on that. I want this to look like the dream that they imagined. I think about that a lot. I think about how much talent they have. How do I unlock all of that stuff and allow people to learn and grow and just pursue the stuff that they want? I worry about my humans probably the most of anything. I think about our customers a lot. One of the things about running this business is that we’re very intimate with our customers. Clothing is an intimate thing. We often know when people are pregnant or when they’re moving or when they’re changing jobs. We all could know that way before even their families, and so it’s a huge responsibility to be a part of somebody’s life like that. When we do well, and we make good on that trust, it feels really good. When we don’t -- and everybody makes mistakes and so it happens -- when we don’t it sucks. It really does. Sometimes we will ship completely the wrong size out. Life that happens. Somebody on the other side is waiting for a size 24 pair of pants that are going to make them feel great. We ship them the completely wrong size and they don’t feel great about themselves. They either can’t get them on or it’s just not what they expected. That’s like a common one that happens regularly. More uncommon, but also happens, is like stuff gets stolen, or we forget to, I don’t know. Over the snow we had last week, we had to close the store. Not everyone got our emails and they drove out to the store looking to pick up their stuff. And it’s like, “I’m going on this trip. I counted on you, and now I’ve got to go shopping. This isn’t the promise.” So that part is like… It’s really… It is an amazing gift of trust to be that much a part of somebody’s life. A lot of our customers like… I’m one of these people. I haven’t worn my own clothes in years. That’s a huge amount of trust that people are lending to us. We want to make good on that every single time and we can’t always make good on it. That part, I worry about that.