“It's terrifying and
it's also really, really fun
and feels right.”
Emily Kenney, co-founder of Wearwell
Erin Houston and Emily Kenney are the co-founders of Wearwell, a personalized shopping experience that makes it effortless for women to find clothing that fits their style and their values. Here they talk about the hours spent seeking sustainable fashion options, the hard work involved in creating a seemingly effortless partnership, and how to “find your people.”
What was your initial vision for Wearwell, and what drew you to that vision on a personal level?
ERIN: Both of us have different experiences that came together through this journey. I was working at a media company heading up their corporate partnerships division. The media company serves the international development community, so a lot of my clients were really large multinational corporations that were doing corporate social responsibility work or emerging markets work in a variety of places across the world, and actually making really tremendous impact in the lives of people. Unfortunately when the Rana Plaza factory collapse happened [which caused the death or injury of approximately 3,600 garment workers in Bangladesh in 2013], I realized that none of my clients were in fashion and apparel. And then when I tried to go shopping for my own clothes and started picking up tags and seeing "Made in Bangladesh" of course made the connection that, if I want this industry to change, I need to shop differently for my clothes.
EMILY: So at the same time, I guess before Rana Plaza, all my experience was working mainly in developing countries and doing field-based operations, data collection and research, and evaluation for local community development nonprofits. I moved back to the U.S. to go to grad school, which is where I met Erin. When Rana Plaza happened, I was going through this transition back the U.S. The local food revolution was happening, so I was figuring out, “Okay, I'm coming from working with small coffee and produce farmers in Latin America. Can I shop locally now that I'm back in the U.S.?”
After this shift with my food, Rana Plaza happened and I thought, 'I have a career that's aligned. My food habits are aligned. Can I shop for clothes that are aligned?' I was looking at child labor laws and studying: What are the rights of children? What does fair trade mean? All of these different high-level, development-related labor issues. In a similar way to Erin, I tried doing it [shopping for sustainable clothing] and I couldn't. I was reading tons of reports, spending hours doing this, finding really expensive items that I couldn't afford as a grad student, and just found it really frustrating when I realized that I'm coming from working in global development directly in communities, but really all the different sectors and projects that are happening aren't looking at fashion. I feel we were coming from these two areas of micro-level, macro-level, realizing nobody's really talking about it and if the consumers cannot do it—either they can't find things or they don't have time to vet things themselves—there's never going to be any pressure for companies to actually change.
Did you have any fears about becoming an entrepreneur?
ERIN: Obviously there's the fear of saying goodbye a paycheck. There was also the fear of: Will anybody even like this? We did a couple things to validate before making the leap, but honestly the biggest motivator was that I couldn't stop thinking about it. I've always had a little bit of an entrepreneurial spirit. I remember telling a couple close friends and my parents about this, and they had this attitude of: “Okay, she'll be on to the next thing in three months.” But this is the thing that I thought about for years before actually going fulltime. That helped with a lot of the fear and actually making that leap. Not only do I think that this is a real opportunity, but it's the thing that I want to be working on, because I’m using all of my free time working on it.
EMILY: In a similar way, I never saw myself starting a business. I think now, looking back, I realize I have an entrepreneurial spirit, but I didn't ever call it that. I always wanted to live abroad. I was consulting or working for really small NGOs that were startups—super scrappy, getting things done, and wearing all the hats. I always loved that, but never specifically connected it to: That's being an entrepreneur.
When we came up with this, I was so excited. It really was that thing that was in the back of my head all the time. Every few months, especially in the beginning, it would kind of be like, “Are you still thinking about that?” It was just this whole thing where it was like, “Well, let's just do it. Let's see what happens.” It was scary, and a progression; it's sort of like you dip your toe in, and you get to your ankles, then you're at your knees, and all of a sudden you're up to your eyeballs completely working on it. I did a slower progression [than Erin did]. I was part-time on some other things and working on Wearwell. It's way more stressful to start a business and yet, it's so much more enjoyable than anything else. Once you realize that, you’re like, “Oh, yeah. This is what we're supposed to be doing.” It's terrifying and anxiety-inducing, but it's also really, really fun and feels right.
What has been your greatest struggle in founding Wearwell?
EMILY: For me, it was my old career. It is so related to what we're doing, with what we're looking to change with Wearwell. But on the surface, it’s drastically different. There's no overlap in the people I was working with before to working on a fashion technology startup. Also I was living in other countries, so for me, I think that personal challenge of having two identities.
I knew the connection [of sustainable fashion] to a bigger system, but everybody that knew me through that work, if I also told them, “I'm starting a fashion startup,” they would look at me and be like, “What are you talking about? That makes no sense from what we know of everything you do.”
ERIN: I have two. One's identity related. It's actually the polar opposite of Emily—and I think this is perhaps an entrepreneurial journey challenge that never really goes away—is people perceiving you as having a singular identity, and that's the business. When you when pour your heart and soul into the business, you are part of it. It is you. But you also want to have fun and put the business aside for a little while, or you want to have these other aspects of your life that you can have conversations about with people. That's something that is certainly a journey: being able to express to people just how passionate I am about what we do and how much I love what we do, while holding space for the fact that it is really hard to be an entrepreneur and sometimes you need a mental break.
The other for me is kind of funny, so take this or leave it for what you're writing, but public speaking. I used to black out from public speaking. Like, completely be unaware of whatever I said. [Laughs] And now I don't even get nervous about it—unless it's like appropriate nervousness for a pitch or something.
What has been the greatest triumph in your founder’s journey so far?
EMILY: The one that first came to mind is how we work together. We've known each other for seven years. We've been working on this for maybe four years, and just the trust and partnership that we have. There are definitely stressful times and hard decisions and hard conversations, but just the way that we work together and treat each other and respect each other, and just know that we are a team in this and that the business doesn't exist unless like the other one is there—I'm really proud of that.
ERIN: We don't define things as like, “This is your part of the business and this is my part of the business—and don't touch it.” [Laughs] We very much collaborate all the time.
EMILY: And yet, at the same time, we know each other’s skills so well and how our working styles are, that it's almost like this unspoken—like if something comes into our inbox, it's like this unspoken: “Oh, I'm going to do that,” or “Erin's going to do it,” without having to actually delegate to one another. I think more and more, especially since being in Philadelphia and getting to know so many other companies and founders, I think that your relationship with your co-founder is so essential. It's like a marriage. It's like a partnership, and if it's rocky, then everything feels rocky. I'm just really proud of how we talk through things, how we work through things, how we just work together.
ERIN: And it is, especially having conversations with other founding teams, it really is rare. That feels like a wonderful thing that we've actually worked to build.
“Don’t waste your time
on the people who don’t
get you and why you’re
doing what you’re doing.”
Erin Houston, co-founder of Wearwell
What has been your biggest personal sacrifice in becoming an entrepreneur?
ERIN: I'm not going to lie; it's financial. I haven't properly traveled in years now. I used to travel all the time because I loved it. So things like that, that you say goodbye to. But also the sacrifice that comes into play when you're not quite sure how you're going to pay rent—that type of thing. It's the really real stuff.
EMILY: Financial, for sure. It's always on your mind. The business comes first. You know you need to kind of prioritize certain things, so sometimes it’s like between a rock and a hard place where you're like, “Certain things need happen, but I also need to pay rent.” I think a lot of times, founders, after raising a ton of money or selling their business and coming out the other side, you hear that reflection of like, “Yeah, but it always works out.” And it's true. It does work out. But when you're in the thick of it, it's really hard at moments, day-to-day. You say no to things.
Has anyone in your personal lives been a constant source of support?
ERIN: My parents. I fully expected them to think I was crazy and discourage me from quitting my stable job—sable and rather exciting and prosperous job. [Laughs] Instead, the hardest question I got from them was: What are you doing about health insurance? The rest was pure encouragement. Still is. On really, really tough days when I'm curt and short with them, they’re like, “I love you. You can do this. You're great.”—Which I feel multitudes of gratitude for.
Also, we have a couple mentors. We have a group of mentors that have been phenomenal, but we have two in particular that have been particularly outstanding: Holly Flanagan is one at Gabriel Investments. Brigitte Cooperman, is the other. She's had experience in retail and e-commerce, and clothing and apparel for decades. They not only have been sources of encouragement, but they've also been willing to open up their networks to other people who can help in whatever it might be that is maybe a business challenge, maybe it's a personal challenge, maybe it's just something related to us continuing on this journey. That's just been tremendous.
EMILY: For me, it was my parents also, my family. In a similar way, when I told them, I was so nervous. I was so scared for this conversation in a way that I just never—I don't know why. Looking back, I have no idea why. Their reaction was like: “Is that what you wanted to tell us? Okay!” They reminded me that, when they were first married, they opened up a Baskin-Robbins franchise. My mom was like, “You do remember that we had that business and we ran it when we had three kids under the age of four?” In that moment I was like, “Oh, yeah. I shouldn't have been scared to tell you.” They supported me so much. My siblings and my parents still to this day will just be like, “How's it going? Do you need anything? Do you want to talk about it? Do you not want to talk about it? We're proud of you. Just keep doing it, and let us know whatever you need—no questions asked.” I think for both of us, having that family support and knowing that we have people that just believe in us and don't think we're crazy is just such a solid foundation.
Just to second what Erin said about Holly and Brigitte: I've had really great mentors before that I'm so grateful for, and having them come into our lives—I can't even express it.
ERIN: Doors fly open when we talk to them.
EMILY: Doors fly open that we don't even really ask for.
ERIN: We didn't even know they were there.
EMILY: We'll just send like a quick “Hi” update email and they're like, “What do you need? Let's do this and this and this.” The amount of energy and encouragement and confidence that they have in us, especially having as much experience as both of them have and how much we look up to them professionally—Your parents of course love you and support you, but having two women like that is just unreal in how supportive they've been to us.
Did anyone in your life try to dissuade you from becoming an entrepreneur?
ERIN: We have had some experiences of—How do I put this? A certain demographic of people who we do not serve as customers who are older, who are white, having dissuading conversations at conferences, on phone calls, things like that that actually happened fairly early on. I remember hearing the words, “You're never going to get funded,” very early on, or “I just don't see why this is a business opportunity at all. Why aren't you a nonprofit?”
EMILY: Or “Maybe I'll ask my wife.”
ERIN: Exactly, yeah. And I don't mean to say every older, white man is not helpful, because it's actually far from the truth in our experience. But this old school demographic that just doesn't really get what we're doing that we had to persuade otherwise, and then eventually deciding, 'You know what? We're just going to build this and prove them wrong.' And that's how we fixed that criticism.
EMILY: We've also had individuals of the same demographic and who are also more old school and they know that they're old school in the way that they see business and investment that have also been champions for us. They see what we're doing and they see who we are and they identify that we have the ability to do this. I think in those early conversations, it was easy to get frustrated by it, and discouraged. I think most female entrepreneurs would have similar stories and similar discussions under their belt that they can look back on. I think it helped us get a little tougher, but also realize that rejection kind of doesn't matter. It's like you just get used to it in a really funny way.
ERIN: It helps you weed out who your people are, and that's fine.
EMILY: Yeah. I feel like we've gotten that advice a few times of like, if somebody doesn't get it, they're not your potential investor, or they're not your potential board member. They're not going to get you, and you're not going to get them, and that's okay.
Tell me about your work-life balance.
EMILY: Usually, if one of us is feeling overwhelmed, we have this unspoken policy that we just need to say it out loud to the other person. It's usually like, “Hey, this isn't going to change anything. You don't need to do anything about it, but I'm about to burn out.” We know it's not something the other person has to fix. It's just like, we need to talk about it because usually if we don't, it's going to get bottled up and we're going to actually burn out. We also are firm believers in like, “Hey, I didn't sleep great so I'm going to start at 10 today,” or “I really need to take a nap, so I'm going to take a long lunch and take a nap.” It definitely isn't perfect, and we work longer and we work on weekends, but it's not because there's a judgment if we don't.
ERIN: My attitude has definitely shifted. My work-life balance style used to be I work when I am expected to, because I was in an office setting before. I wouldn't work at all on the weekends. I wouldn't check my email at night. I wouldn't text co-workers unless it was within those hours. I had to readjust what work-life balance looks like for me because that's not the reality of working on your own business. I don't care how good you are at maintaining certain hours; it's just not the reality.
I've had to reset my expectations and I think the most productive way I'm able to do that is realizing I'm only going to work when I can actually get good quality work done. That also means being strategic about the hours that I do certain things in the day. So if I have to write something, I know that I'm going to be able to write it my best and most quickly between 9:30 and 11:30 in the morning without any distraction. So I'm going to save the other tasks for the end of the day. And I'll get to them. It might be that I work a little longer that day or it might be that I've done a lot of productive stuff and now my brain's not functioning, so I stop at 4:30. I think being strategic about when you use your brainpower has been the most helpful way for me to rework what is balance. It's not a time-spent type of thing; it's just how I'm spending that brainpower.
What would make you feel like you accomplished what you set out to do with Wearwell?
ERIN: There are a few things, but the one that sticks out most to me is, when we started Wearwell, our real goal at the end of the day—in addition to making it no longer something that you needed to question, that people just assume that their clothing is ethically and sustainably made because there’s been so much change—is actually being a company that revolutionizes the industry so that it’s more ethical and sustainable. A milestone within that goal for us is being able to be in partnership with large brands to help them navigate an informed way of how they can change their supply chain practices. What I mean by that is being able to offer them insights, not just on what their particular customer base or target customer segment says they want, but how they actually choose to spend their money. That type of data and insight, those are things we can provide with the service that we’re building. When we’re able to actually launch a service like that and be in partnership with those types of brands—that will be an enormous milestone for us.
What would you guys say is the most important lesson that you've learned as an entrepreneur so far?
EMILY: What come to mind are two things, which almost seem to combat each other, but they make sense. Trusting your gut—meaning trusting our collective gut—has been a huge lesson. But then, at the same time, learning how to ask for help. We’ve gotten so much better about this, but early on, you’re kind of stumbling through. You’re making it up as you go because there’s no manual of ‘Step one: Do this. Step two: Do this.’ When we have those moments where we have no idea what to do, when our gut is telling us this one thing or we have just no idea what the right thing to do is, knowing without even really having to think about it anymore that now is the time to ask for help. Now is the time to shoot a text to other founders, send out something on the PSL Listserv, or ask our mentors. That usually makes all the difference and takes hours of worry and twiddling your thumbs trying to figure out what to do just go away because you can just reach out to people.
ERIN: I guess navigating the space between following your gut and listening to advice, because if you just listen to advice, you’re not going to get anywhere. But if you always listen to your gut, you’re going to have blind spots every step of the way.
EMILY: And you’re going to waste a lot of time creating something that you could just reach out and say, “Hey, has anybody already done this?”
ERIN: Another one that I’ll throw out there is resiliency, but not the way that people typically think of resiliency as just never give up. Rather, resiliency in constantly searching for new solutions. Not to sound super cliché, but if one door closes, find a window, right? For us, that certainly has happened many times where, we’re like, “Okay, this is just not going to work.” Our answer is not “Give up, the business is done,” or “Give up, this was a bad idea.” It’s always, “Okay, it’s not working how we’re doing it. Let’s switch gears and try it this way. Let’s make it work this way, and if it doesn’t work that way, we’ll find another.”
Do you have any advice for female entrepreneurs in a similar space or the tech space in general?
ERIN: I think the best advice is: Find your people. Don’t waste your time on the people who don’t get you and why you’re doing what you’re doing. I think it can be really easy as women to waste your time, because women tend to want to please more people. But really sticking to the people who already get you is key.
EMILY: Be really kind to yourself, because I think there’s a ton of conversation about gender and women and equality, which is amazing. But I think it also puts this extra layer of pressure, of like, “Yeah, the odds are stacked against us, so I need to do everything even better to get ahead and actually succeed.” Realistically, you’re going to mess up and you’re going to be bad at certain things, and you’re going to be great at certain things.
I think women tend to think and reflect and be really open about talking through everything in ways that stereotypically male founders might not. They [male founders] might just glaze over, like, “This is great. This is awesome. We’re amazing.” Don’t listen to that. Be kind to yourself. Find your people and also filter things for yourself a little bit. Maybe you’re going to be the only woman in the room, and maybe everyone is going to be telling a really great story about how amazing they’re doing, and just remember that it’s hard for everyone. You’re probably stronger than most people in that room because you’re a woman. I’m just biased and think women are badass.
ERIN: I was privy to a conversation recently about gender lens investing, and—just from a macro level of what Emily’s talking about—there was a woman who said, “We need to stop the conversation the way that it’s happening right now and reframe it, because somewhere along the way, we didn’t just say, ‘Invest in women because there are good business opportunities.’ It was: ‘Invest in women because they are expected to outperform.’ Why are we putting that level of pressure on female founders, that they must outperform their male counterparts?” So keeping in mind that mentality that you don’t have to be perfect. You don’t have to be better than your male counterpart. I hope they are, but don’t put that pressure on yourself.
This interview has been lightly edited from an in-person conversation for clarity. Capturing Lightning is a project from Woden, a strategic storytelling agency in Philadelphia that helps organizations articulate who they are and why people should care. To learn more about how to tell your story, visit us at wodenworks.com.