Jenny Fleiss on Unstoppable with Kara GoldinMy guest on today’s episode of Unstoppable is the incredible innovator and entrepreneur, Jenny Fleiss.

Besides co-founding and serving on the board of Rent the Runway (the hottest clothes rental company on the internet), Jenny leads an amazing new startup called Jetblack, a members-only personal shopping and concierge service.

On today’s show, Jenny talks all about how she came up with Rent the Runway while she was in business school at Harvard, her tips and tricks to succeeding as an entrepreneur and innovator, her best advice for raising venture capital and so much more.

I think you’re going to love todays episode!


You can Subscribe and Listen to the Podcast on Apple Podcasts. And be sure to leave us a Rating and Review!

Unstoppable with Kara Goldin on Apple Podcasts

“Entrepreneurship is like highs and lows. I think it is like flying a plane at low altitude. It is like the highs are really high, and the lows are really low and it feels like your going to crash. It is great having a co-founder because there are different moments during then when you need to pick each other up.” – Jenny Fleiss

Show Notes:

  • What is Rent the Runway
  • How to start a business
  • Why to start a startup
  • How to raise venture capital
  • What is Jetblack
  • How the Walmart incubator works
  • How to innovate

“I think we need to constantly work at driving this risk-taking culture and training that it is ok to fail.” – Jenny Fleiss

Links Mentioned:

  • Connect with Jenny Fleiss:

Twitter | Instagram | Rent the Runway | Jetblack

“Another piece of advice we give sometimes is not to write a business plan. Like in the example I just gave you of Rent the Runway, you’ve got to get things out to the consumer.” – Jenny Fleiss


Kara: Hi everybody, it’s Kara Golden from Unstoppable with Kara Golden, this morning in New York. Very, very excited to introduce you to our next guest, for those who don’t know, Jenny Fleiss. Yay!

Jenny: Hello.

Kara: Very, very excited to see her. Jenny is the co-founder and current board member of Rent the Runway. Jenny recently left the day to day responsibility at Rent the Runway, and is now leading a very, very cool startup within Walmart’s tech incubator called Jet Black.

Jenny: Yeah.

Kara: Reshaping the way consumers shop through one to one experiences, super highly personalized. I’m really excited to hear her talk more about this.

And again, going back to Rent the Runway, I remember when she was first starting it, and we’ll get into some of those details.

Jenny: I know, it’s like 10 years ago now. We had our 10 year anniversary.

Kara: Crazy. 10 years.

Jenny: Yeah. Dog years. It feels like 50 years.

Kara: Yeah, it’s insane. So Jenny is one of Inked Magazine’s 30 Under 30, Fortune Magazine’s 40 Under 40, and Most Powerful Women Entrepreneurs, Fast Companies Most Influential Women in Technology. Lots of good, good, good things that she’s done have been recognized, very, very cool.

So welcome, Jenny.

Jenny: Thank you. Thanks for having me. It’s so good to see you.

Kara: Yeah. Super great to see you too. So I want to talk first about Rent the Runway and when we first met. You had graduated from Harvard business school, actually with somebody that used to work at Hint, Alyssa, ages ago. We love Alyssa.

Jenny: Classmate of mine, she’s great.

Kara: Yeah. Super, super cool. So tell me a little bit about Rent the Runway first, and how that all came about.

Jenny: Sure. So I’ve always had this entrepreneurial spirit, I loved running lemonade stands. I knew that at some point in life I was gonna start something. And even prior to Rent the Runway I had side hustles while I was working in finance. And in business school, I met my co-founder, Jen Hyman. And during our second year we were having a lunch discussion and she was telling me this funny story about her sister Becky, who was trying on a Marquesa dress that she had just purchased, it was a $2000 dress.

And Jen was saying, “This is nuts, you’re going in credit card debt over this. You have so many dresses in your closet, why did you buy this dress?”

And Becky said two things that were pretty funny, but also pretty telling about the culture that we were in at that moment, and some major trends that were shaping how millennials were shopping.

The first was that all the dresses in her closet were dead to her because she’d been photographed in them, and they were posted on social media. So she couldn’t possibly wear one of those dresses again. This was November 2008, social media was on an upswing, and it’s gotten even more crazy since then.

But it was doing two things. It was making everyone their own brand, so there was more eyeballs on you. Suddenly there were thousands of eyeballs every time you posted something on social media. And it was truly ruining the ability for you to wear something one day, and wear it again the next day.

As a woman you probably relate, it’s like sometimes you wear an outfit and you’re like, “This is great. I paid money for it, I’m gonna wear it again tomorrow with a different group of friends.”

Suddenly, with social media, you can’t really do that as much.

The other thing Becky said was, “You know, I’m going to a wedding and I might meet my future husband at this wedding.”

So this funny but true point that you have all these high-stakes occasions when you’re a woman in your 20s, that it’s really important that you put your best self out there, you look great. And ironically, I think as I’ve gotten older, as you get older, you have fewer and fewer events, but you reach this different level of income earning potential.

So there’s this gap of, you’re a post-grad, you have all these events, you want to look great, you care about social media and how do you afford a wardrobe to make that happen?

So the response that we had seen in the industry was fast fashion. H&Ms, or Forever 21, ways to get a knock-off stylish piece of fashion that you weren’t breaking the bank on.

So we realized that between some of these trends on the consumer side and also the retail and designer industry, there was an opportunity to create something different. And so, we started talking about what became Rent the Runway. And decided to test out the concept with consumers, because in my entrepreneurial DNA and Jen’s as well, that’s what you do. You don’t write a business plan for four months, you get out there and just figure out what’s what.

So we wound up buying dresses, and we bought them in our own sizes. And we’re like, if this doesn’t work, we’re gonna have a great wardrobe. Always have a backup plan.

Kara: So how far after business school was this?

Jenny: This was during business school. This lunch conversation, within having this lunch conversation and the next two weeks, we had met with Diane von Furstenberg, and gotten all of her feedback. So cold called, emailed her, driven to New York and met with her. We had run this test pop-up where we were renting dresses to women, figuring out how to operationalize it.

Found a lawyer who was representing us on a contingency basis, to introduce us to venture firms and help us set everything up. So yeah, it was a pretty wild ride right from the get-go.

Kara: That’s amazing. So you cold called Diane von Furstenberg. What was her response to this?

Jenny: So the first email, we weren’t sure if it was her email, and we got a response that day, and it said, “Come to my office tomorrow at 5 pm.”

And we’re like, is this her? Is this actually her? It was a hot pink, bubble letter response. But we drove to the city, and we put on our DVF dresses, and sure enough it was her, and she met with us for an hour and a half, which is very generous, and told us how she hated the concept.

So we listened to that. And I left pretty demoralized.

Kara: Why did she hate it?

Jenny: Yeah. So why did she hate the concept? And that was I think the big aha there, is that you learn so much from everyone you talk to. So if you can ingest it and then think about how to reframe your business, or things that you might want to tweak and pivot.

So what she was nervous about was cannibalizing her sales, right?

Kara: Totally.

Jenny: So would people continue to buy her clothing if there was an option to rent the items? So what we wound up being able to prove, and what we talked to her about, was this is not your customer who’s buying items at Saks, who’s actually in their 40s and 50s.

This is a consumer who’s in their 20s and 30s, who otherwise you were losing to the Zaras of the world. And if instead you can introduce them to your product through experiential marketing. They’re gonna rent it, they’re gonna try it, they’re gonna fall in love with it. They’re gonna see how different it feels from a fast fashion knockoff item.

And then later in their life, they will buy something from your brand. Maybe it’s a black blazer, a white T-shirt.

So that was one thing. We also said, this is a great way to get more of your editorial styles out there. So the Neiman Marcuses, the Saks of the world, they’re not buying the bold prints, these statement pieces that all these designers want to get out there, the actual runway items.

Because it doesn’t make sense for a woman to purchase those. You buy the black version, you buy the basic version. So this was also a great way for these designers to get some more of their exciting, creative pieces out there and then in turn, onto social media and start more of a discussion about their brands.

So those were some of the unlocks that in hearing her response, we were able to learn, and tweak and pivot our business model and how we engaged with future designers.

Kara: So you went back to school.

Jenny: Back to school.

Kara: And after having this meeting, you guys were- I mean, were you feeling energized or were you feeling crushed at that point?

Jenny: I was honestly feeling kind of crushed. Jen was energized. I think there’s these moments. Entrepreneurship is like, highs and lows. And I think it’s like flying a plane at low altitude. The highs are really high, and the lows are really low. And you feel like you’re gonna crash.

And it’s great having a co-founder because there’s different moments during that when you need to pick each other up. So i think Jen’s attitude was very much like, “We just learned all the things that are paining her and that are hard in her industry right now.”

Saks was slashing prices 70 percent at the time, because it was a recession. So she was like, “How do I retain control of my brand?” There were pain points that she felt.

So she was like, “She just told us all these things and we can pivot, and we can address them in a really smart way.”

So that took work. I think we came back to school, we regrouped, we thought about, how do we position this? What do we need to tweak and change?

And then we had some serious conversations about, could we raise money again to make this a really big business?

And the reason we decided to go after it was from the consumer response. So yes, we saw needs that the Diane von Furstenbergs of the world had in their world, but from a consumer perspective, the big unlock was when we tested this concept and we bought dresses and we went to go rent them?

Consumers were emotionally changed when they put on a great dress. So when you see that transformative, you put on a great dress, you’re strutting your stuff, you have extra confidence, you realize that there’s something just magical about what this business can do for a consumer.

So from that, we said, let’s go after this. Let’s make this something really big.

Kara: So were you actually going after the Harvard business school audience initially, or were you-

Jenny: A little bit. We were going after anyone who was accessible to us. So we were at Harvard business school, our first coffee meetings and surveys that we sent out were to our friends at Harvard business school.

When we did this pop-up with the dresses we had bought, we went across the river to Harvard undergrad, and we realized they were having all of these graduation events at the time. It was March or April, so there was a need for them to have lots of dresses. And we invited different groups of women. We had the Women in Business group. We had the A-List Sorority group.

And through that we had this mock customer segmentation also, which was interesting. And we wanted to test and learn and observe. We wanted to learn, what styles did they want? What sizes? What designers? Did they care about the pricing? Did they need styling help? Did they need to try items on, and was fit an issue?

So we were trying to think about all these things through a minimum viable product test, is what it’s technically called. Though at the time we didn’t think about it in that formal of a way.

And from that moment, we did more tests. We then went and did a test at Yale, which is where I went to undergrad. And that time, we didn’t let customers try the dresses on.

So each time, we were trying to learn more things. And then eventually we did a test where we emailed people a PDF document and said, “Call this number to rent one of these dresses.”

So each time, with very scrappy, low-cost ways, of just getting a little more confidence in the business concept.

Kara: That’s awesome. Very cool. So you graduate and then you guys decide you were both headed back to New York? Was that a decision that you made based on being around fashion, or were you guys just ready- are you from New York?

Jenny: I’m from New York. I’ve lived here my whole life. And I was engaged, so definitively coming back to New York anyways.

The big decision, Jen and I both had other jobs lined out that we had worked really hard to get, and we were very excited about also. So for us, there was this agreement that we were gonna raise money by the time that we graduated, otherwise we had these other jobs lined up and we were gonna go do those jobs.

And part of that was realizing that Rent the Runway would require a lot of capital. It wasn’t a business that you could just bootstrap. Because you needed to buy a lot of inventory to make a real, legitimate business, and you needed to build an advanced website to enable a reservation capability.

So knowing that, we said, let’s put ourselves on a timeline and a clock to raise this venture capital. And we wound up raising, from being capital ventures, which was our seed investor, right around the time we graduated. So from then on it was like no looking back, and quit the other jobs we had teed up, and went at it full steam.

Kara: What was the first round that you did? How much did you guys raise initially?

Jenny: We raised $1.75 million. And I think like most first rounds, they convinced us to take a little bit more than we thought we needed and wanted. For better or for worse.

But there was a great investor there, Scott Friend, who I’m seeing later today. We still talk to him probably every week if not more than that. And just became such a partner in the business.

So I tell people when you’re raising venture capital, yes, the firm is really important. But I think thinking about the partner, super important as well.

He came, he was an entrepreneur himself, so he really understood where we were coming from, exposed to the retail industry. And literally feels like a co-founder in the business. That was the extent to which he was invested and involved with us.

Kara: That’s awesome. Very very cool. So you go 10 years at Rent the Runway, and then you decide that you’re gonna go off and do another startup. So how did that come about?

Jenny: It’s crazy of me. So about 18 months ago, I left Rent the Runway on my day to day and I started a business called Jet Black.

Jet Black is the first business within an incubator that Walmart set up. And the incubator is called Store #8, it’s meant to focus on key technical innovations that are gonna change the retail landscape.

Kara: So did they reach out to you to-

Jenny: They did. So Mark Laurie, who started, and then started Jet, which was sold to Walmart, he’s now the CEO of

I have known him since the earliest days of Rent the Runway. I actually got to know him because I was trying to learn about logistics. I ran our warehouse for about four and a half year. I vertically integrated dry cleaning, we run the world’s largest dry cleaner at Rent the Runway, to give you a sense.

And I had no background in logistics, warehouse, fulfillment, supply chain. And at the time, Diapers was a huge company, was very successful in the New York area.

And I was like, who can I find and who can I learn from? So that’s how I got connected to Mark. Stayed in touch with him, so he reached out and said, “I want you to start this business within this incubator.”

And it was really exciting to be able to get to work on it with him. He’s my co-founder in this business, because a lot of it is his vision that I’m making come to life.

It was a really interesting setup, to think about, how do you drive innovation even faster than you would as a standalone entrepreneur, being inside this broader ecosystem. So what can we leverage, in terms of the infrastructure of Walmart, to go super fast and quickly?

And then I think finally, thinking about the impact that you can really have. And that’s what matters to entrepreneurs, you want to have impact, you want to do something meaningful.

Being part of the largest retailer, I can drive so much impact, if I can create real innovations.

So the area of focus for Jet Black is conversational commerce, which is shopping over voice or text. And conversational commerce could even be when you go into a store, and you’re having a discussion with a sales associate about the right sneakers to purchase, or fleece to buy, or whatever the case. And you’re asking them questions, and there’s a back and forth discussion about it.

That sort of interaction has gone away in how people shop online right now. But if you think of some of the voice devices and some of the innovations that are happening with voice technology, natural language processing, those interactions will become possible again.

So that was the landscape of, this is gonna be a change, let’s innovate.

So what we decide to launch is personal shopping over text message. You can text whatever you want, be it laundry detergent, a birthday gift, or designer handbag, and we will serve out typically three options of the best options that we think match who you are as a person, and the best of the best in the market at that time. And then we will deliver it to you same or next day.

We use bags, not boxes. If it’s a gift, we’ll gift wrap it for you. We do free and easy returns.

And the main goal for us is trying to save you time. I think time right now is the greatest luxury for consumers. And everyone is looking for new ways to save time. So shopping over text and eventually voice is a very efficient way to get things done.

Kara: So it’s all being sourced by Walmart.

Jenny: It can be sourced from anywhere, actually.

Kara: Oh, interesting.

Jenny: So all things equal, we’ll source from Walmart or Jet. So your laundry detergent, your paper towels, a lot of great toy selections, and then there’s the Walmart family of brands. So Bonobos, Hay Needle, Modcloth, they just acquired Eloquy, there’s so many great brands that they have as well.

But if someone wants a Gucci handbag, we’ll go buy the Gucci handbag. If someone wants a designer top or dress, we’ll go buy the dress. So we’re starting to partner with major retailers and brands so that we can source those products.

But think of it almost as a personal shopping layer, where we’re going and finding these items and making it really efficient for the consumer.

Kara: So how is it different from I don’t know, insta-cart, or even Grubhub, where they’re gonna deliver something? Obviously those are more food-focused.

Jenny: Well, sometimes I compare us to Instacart for everything. I think that’s a decent comparable. So I think a few things.

One is that it’s over text message and voice, so you can do voice to text right now. So that’s one of the main things customers love, actually. As much as it sounds simple, the modality of being able to use text message, which feels very personal and fast, I don’t even need to open an app, I can just fire something off, is very powerful.

What we actually do is we store all of the preferences you have, and the products you’ve bought in the past, to enable click-free shopping. So that’s another key difference.

So if you were to say, detergent, I know what detergent is. And it’s great, your order is confirmed for Tide clean and free, and it’ll be there later today.

So just think of this mind-dumping behavior, the way people shop today is on this more rolling basis, where you realize that you are out of something, you need something, and usually you need it that day or the next day.

Versus in the past, people would make these weekend shopping trips with lots of items all at once. And what happens is people can be really distracted by all the things they need to get done and do. So to be able to just mind dump onto text is one of the things customers love the most.

Kara: Yeah. That’s such a great idea.

Jenny: I think another difference that people really like is this universal catalog, this idea that you really can shop for such a wide range of products. It’s another efficiency driver. I don’t need to remember as many logins and passwords and enter new shipping addresses to be able to order a gift for the holidays at the same time as I’m ordering paper towels. It’s truly the most efficient.

To be able to store, I always deliver gifts to my cousins in California, and their address is stored, so I can just say, “Send that Hanukkah gift to the cousins,” is really powerful.

And then the third thing that I think is differentiated that people really love is the ability for us to recommend products, but for us to also answer key questions about the product.

So what we find is that sometimes customers, let’s say you’re buying a night light for your kid. You might have a lot of questions. And if you were to go on a website, you’d have to read reviews and Q and A’s, it might take you a ton of time for a basic purchase.

And instead, if you could just ask someone directly the question that you had, it’s a much more eficient exchange to get the product that’s the best fit for you.

Kara: So is this nationwide?

Jenny: It’s New York only right now. We just launched in June.

Kara: I’m going online after this.

Jenny: We just launched in June, it’s invite-only, it’s membership-only. It’s $50 a month.

Kara: Can I be invited?

Jenny: Yes. You can be invited, but for when you’re in New York, you can be invited.

Kara: Okay.

Jenny: Over time, we’ll definitely scale this out. But we’re seeing so much demand in New York, and also so much usage. So we have 75 percent engagement every single week, the average consumer is asking for 10 items every single week. Super high conversion, because it’s this intent-based shopping. You come to us when you really need something.

So it’s efficient for the consumer not to be cluttered with all these other things on a website and overwhelmed with all these items on a website, we just make it as simple as possible for you.

Kara: I think my brain is racing right now. If you could get a hold of somebody’s calendar, for example, to figure out, keep track of all my nieces and nephews’ birthdays.

Jenny: Yeah.

Kara: And just figure out what they would want based on their age.

Jenny: And over time we will do that. A fun usage case, because we’re always learning from our consumers too. So one fun use case is people will screenshot paperless post invites, text it to us, and immediately I know the theme, the age, the date of the event. So I can just be like, “Here’s my recommendation, it’ll be gift-wrapped and delivered to you in time for the party.”

So just think of the ways you can drive efficiency and time saving in life. You’re a mom of four kids, I have three kids. So some of this concept came from just my behaviors that I started to adopt to save time, of getting to know a sales clerk and texting them when I needed a gift for a birthday party, asking them if they could do the gift wrapping for me.

So I think these life hacks that you develop, and it was the same thing with Rent the Runway. We were living in this moment where Jen and I had a lot of events, and we wanted dresses to wear.

So I think you draw off your own experiences and needs as an entrepreneur.

Kara: That’s awesome. So one thing that I’ve been thinking a lot about is, we’ve seen examples, I think I’ve seen examples mostly of female entrepreneurs that have done this, but maybe Mark’s the exception to this as well, where you’ve gone from being the head of a company, to zig-zagging into working inside of Walmart.

Granted, you’re running a startup inside of Walmart, but I think about Julie Rice, for example, from Soul Cycle. She’s now the CMO of We Work.

So I feel like there’s this trend where it’s not like, Jenny needs to go and be the CEO again. She can go and do things because she’s really passionate, she can go and solve problems, great.

What do you think, do you think that’s a new trend for people, just in terms of, I just feel like there’s no, this is what needs to happen, you need to go and be the CEO of 10 companies in your career.

So often I talk to founders, especially ones that are trying to have a family, trying to do something at the end of the day that fills their soul and does something interesting.

Jenny: Well, that’s more what I think it is. So I think careers these days are more of a jungly gym than a ladder. You’re going from one place, to the next, to the next. I think the next thing is you have more entrepreneurship than entrepreneurs.

And what drives entrepreneurs is typically a desire to make impact and to do something they’re passionate about. And with that, to me, titles have never mattered. I think to many people working in a startup, titles are secondary.

It’s not the main thing. So I think that that is the case. It’s less about the title, it’s more about the content of the work you’re doing and the impact that you can have.

For me in this role, I am CEO and co-founder, so it was a unique opportunity, the way it’s set up was to start my own office. So we have our own office in New York, separate from the world of Walmart. So to be this total startup, to hire my team from scratch, was a really unique model.

So even though I’m within this ecosystem and there’s additional learnings that come from that too, like how do you push and make change and drive impact within the broader Walmart organization, but yet getting to do my startup thing, somewhat separated from that, was a really appealing part of it as well.

Kara: Yeah. That’s awesome. How many people on the team now?

Jenny: Almost 200.

Kara: That’s so great.

Jenny: So a really good example of, I started 18 months ago, so the team was 0 at that point. And just that pace of growth and scaling, we could never have done but for leveraging infrastructure around HR and finance in particular.

So obviously the fundraising is done through Walmart, so versus being a startup and having to go through a whole fundraising process, which can easily take six months and all of the founders’ time, that was removed.

Then a lot of the infrastructure pieces, of how do you get benefits and healthcare, all that’s set up. How to get your financial system set up, that was also a plug-in-place solution.

So we were able to get going a lot faster from the get-go. There was recruiting resources that we leveraged, so I’m really fascinated by this model of intrepreneurship. And I very much believe in it. It’s hard to pull off and to do. But if you can make it work, then 1+1=3.

Kara: Well, I think we’re also seeing this trend where large companies, before they were actually trying to do what Rent the Runway did, but instead, now we’re seeing that they’re basically hiring in people who could potentially start these little companies, a lot of people don’t even know that Jet Black is part of Walmart.

I know a lot of people have said to me, “Don’t you know Jenny Fleiss, that company sounds so cool,” it really seems like it’s a standalone company.

Jenny: That’s the idea.

Yeah I think there’s all sorts of different models people are experimenting with, which is very exciting. A lot of venture firms are incubating startups within venture firms as well, based on trends and concepts, and almost hiring the founder to put them into this business and concept that they’ve thought about.

So I love this experimentation with different ways of innovating.

Kara: Do you think, outside of not having to go raise money in a traditional way, and the human resources and the benefits and all that, do you think, what do you think is the key difference in having a Walmart backing you versus the day to day of growing Rent the Runway?

Jenny: Yeah. And I think about it a lot, because it does feel different. The edge that we’ve had in hiring talent and that we’ve leaned into is that we don’t have equity. So right now we don’t have equity in Jet Black. And instead, we pay market comp.

So it’s a very unique opportunity for someone to come work at a startup, have the startup feel and DNA, and fast-paced, and the impacts you’re driving, and the innovative headset that you can put on, but to not have the risk of a startup. Because typically your equity is the majority of your compensation at a startup, and it could be worth zero.

So if you risk adjust what the equity you think you would make in a startup is worth and you back it into compensation on an annual basis, you can attract talent that might not be at a place in life where they can take that risk. Maybe they have a mortgage, maybe they have kids, maybe they’re just not as risk oriented.

So we’ve gotten some great talent, that I think that’s been a unique edge. That said, I think we need to constantly work at driving this risk taking culture, and the training that it’s okay to fail.

There’s still a lot of expectation of specific process and everything being T’s crossed, I’s dotted. We’re going through a performance management process now, and just the level of expectation of everything being so clearly laid out feels very different than a startup.

So you think about, what creates that expectation, and I do think it’s you’re part of a Walmart, you’re making market comp, you’re getting healthcare benefits, maternity leave policies, all these things that are so well ironed out. You become very, subconsciously almost, acclimatized towards that.

And so then I think you’ve got to make sure that you’re having that risk taking behavior, okay to fail feeling in other ways to compensate for it.

Kara: So what’s next for Jet Black?

Jenny: We’re growing, yeah. We’re growing. So let’s see, it’s a very complex technical problem that we’re solving. Interacting over text and voice means that you’re leveraging a part bot and artificial intelligence, machine learning, and then a part human.

And for us, we think that the best is actually a combination of the two. And that’s how you can have a non-frustrating experience that is also scalable and efficient. So for us, most of the work right now is actually on building the technology to support huge scale of this business.

Kara: That’s awesome. And what will be the next city?

Jenny: You’ll be happy, San Francisco, definitely we talk about. But one thing that I think is cool is, we have a wait list right now, so you can sign up on It’s a large wait list, and some of them, many of them are from New York City, because that is where we’re live.

But I like seeing where else there’s interest and demand. So I might do it based off of where there’s the most registrants on our wait list to launch our next city.

Kara: Yeah. I think that’s super, super smart. So just a couple more quick questions. Best advice you’ve ever gotten?

Jenny: No doesn’t mean no, it means not right now. It’s a mantra that Jen and I, we say to each other.

Kara: My dad used to say it. My dad had a different way of saying it. He said, “Kara, to you, no means maybe. Maybe means yes.”

Jenny: I mean, I give that advice to people a lot. I love it, I believe in it. Another piece of advice we give sometimes is not to write a business plan.

So just in the example I gave you of when we started Rent the Runway, you’ve got to get things out to the consumer.

Kara: See how they respond.

Jenny: So you can see what’s what.

Kara: Yeah totally, I tell people that all the time in consumer products. We had a business plan, but just getting it on the shelf. There were so many changes. We wanted to get it on the shelf and see how consumers reacted to it, and then once we got it on the shelf, we were changing the labels, tweaking them. We had really small runs.

You never really know until the consumers actually get their hands on it and purchase it with money. It definitely makes such a big difference.

Jenny: Definitely let the consumer lead the way, becomes important not just in the beginning, but it’s something that throughout the life of Rent the Runway and now Jet Black, you need to incorporate in the DNA of how you evolve the business.

So Rent the Runway now is a subscription-based business, primarily. Which is for every type of apparel. It’s not just dresses. It’s blazers, it’s tops, skirts, scarves, coats, everything.

And that really was driven largely by the consumer’s demand for more products, different types of products, realizing that in the market there was this appetite to rent just on a daily basis, and that maybe it was your power meeting at work that merited a cool blazer, not just your black tie event.

Kara: Yeah. What about men on Rent the Runway?

Jenny: We always get this question. Men, the emotional connection I mentioned that women have with fashion, I don’t think exists in the same way with men. I think men can also get away with wearing the same suit or outfit the entire week and no one would probably notice.

So I don’t think that the drive and the demand is quite as large. Of course, never say never. But I think we’ve also hit on a unique and community-oriented brand for women that embodies female empowerment and female entrepreneurship, the story of Jen and I founding the business and now having 75 percent of our corporate team there is women, is really a powerful piece of the business and the brand that we leaned into.

Kara: And I think women are such decision makers. I have two boys and a husband, they’re relying on me to actually go figure out exactly what they’re going to wear to an event. Whether it’s a bar mitzvah or a senior prom, or a wedding, or whatever it is.

Jenny: Totally. Throughout e-commerce, I think the stat is, it’s over 80 percent of e-commerce purchase decisions are driven by women. So when people ask me about creating a female culture, hiring a lot of female employees, I often say, you know what? I hire the best people for the job. I think if you have an ability to relate to the consumer need and to have that vantage point, you’re often best positioned.

So I think there’s a way that women can be a real asset, given that women are driving so many purchase decisions.

Kara: Yeah. I think that’s huge. So if you could try any other profession, last question, what would it be?

Jenny: Any other profession? I mean, this would not just happen, but I think being a professional ballerina or a movie star.

Kara: Were you a ballerina?

Jenny: When I was really little. I had pipe dreams of being a ballerina, it ended at some point. I try to live vicariously through my kids now and push on them a little bit. But I mean, those are really sexy and glamorous.

I also in another life, or maybe future of this life, would like to be Kelly Ripa, just that sort of talk show host, a little funny, a little day to day humor.

And I think one reason I like her and I think a powerful piece of how I try to run my business is, getting to connect yourself and authentic life with work. And I think that’s a really cool aspect of today’s modern jobs is that it enables that.

I can have my kids come into the office. The fact that I’m a mom and I have different needs is helping shape and drive how I evolve Jet Black. I think there’s a lot less lines between work and personal life.

It can be challenging, but can also be really healthy and empowering.

Kara: Yeah totally. Great. What’s your favorite flavor of hint?

Jenny: Oh, goodness. Right now I’m having peach. I do really like peach. I also like blackberry.

Kara: Awesome. And the kids, we just launched the kids.

Jenny: I’m so excited for the kids to try it. The kids have been drinking hint water, they love it. Especially they love, they call it bubble water. Now I start calling it bubble water too. They love that.

But the juice boxes will be huge, the juice boxes are so unhealthy, and there is something novel about-

Kara: Yeah. I think we’re gonna define juice boxes. Most parents don’t really understand that what they’re giving their kids is so much significantly worse than they can imagine.

Jenny: It’s gonna be huge.

Kara: And now what they would drink, so why are they giving it to their kids, their family? So it’s crazy. Anyway, we’re super, super excited about it. So we’ll give you some.

Jenny: That’s great. I’m excited about it too. It’s super smart for you guys. You need to invent a straw that doesn’t enable it to all squirt all over the kid, and then you’ll be true geniuses.

That’s the thing with the juice boxes. Every time they have it they squeeze it, and it comes out all over them. So that’s the next invention you guys can work on.

Kara: No, we’ve been looking at different packaging ideas. That’s what I love about my job too. In fact, I saw one in Europe that I thought was really, really interesting, that actually embedded a straw inside of the top of the box. But the problem is, it’s not recyclable.

So basically when you add any type of plastic, and then the paper, just disintegrates.

Jenny: Paper straws, I need to use three of them to get through a drink, that just defeats the whole purpose.

Kara: And then the recycling of this paper and the amount of trees that we have to cut down in order to actually create more paper straws. Don’t get me started.

Jenny: But listen. If they squirt the hint juice box on them, it’s water. So unlike the sticky apple juice.

Kara: It’s not sticky, it doesn’t stain.

Jenny: It’s like, ugh.

Kara: No, it’s super exciting. Anyway, well thank you so much Jenny, it was-

Jenny: Thank you for having me.

Kara: Yeah, it was great. It was super great.