Inclusive Inventor
How Jenny Fleiss, co-founder of Rent The Runway, created the “closet in the cloud” to bring high-end fashion experiences to everyone, and how she’s guiding the next generation of entrepreneurs with expertise and empathy.
Episode Notes
(3:13) How Jenny’s experience as an entrepreneur led her to join Volition Capital this year
(8:32) Assessing the state of digital commerce—global challenges & innovations
(11:47) Jenny’s POV on the three pillars of personalization-at-scale
(16:56) Launching Rent The Runway with an unprecedented dive into logistics and a crucial market insight
(23:29) How Jenny linked up with RTR co-founder Jenn Hyman, along with her tips for finding co-founders
(29:23) Changing the VC funding landscape and increasing opportunities for women-run businesses
(31:23) Lessons for parents on teaching and encouraging entrepreneurship
Jenny Fleiss is co-founder of category creator Rent The Runway, but in some ways, that’s an understatement of the time and energy she put in to revolutionize the designer fashion industry—and forever change old ideas of Who Gets to Wear What.
In her talk with Jesse, Jenny recounts the detailed logistics work and core insights it took to drive growth at Rent The Runway, with lessons learned for aspiring founders. She describes how she now brings her entrepreneurial experience to bear as an investor, emphasizing inclusivity and the growing importance of shared wins. Jenny outlines a format that digital commerce businesses can follow to create personalized experiences at scale. And she offers advice for parents on how to inspire entrepreneurship from an early age. All told, Jenny’s story highlights the transformational power of building in oneself – and others – the confidence to excel.
Guest Bio
Jenny Fleiss joined Volition Capital in 2021 as the company’s first Venture Partner, where she focuses on next-generation consumer brands. She is an entrepreneur and intrapreneur, founding two scaled digitally native businesses from scratch: Rent the Runway and Jetblack. During her time at Rent the Runway, Jenny wore many different hats, serving as President, Head of Logistics, and Head of Business Development.
Jenny has been honored with numerous recognitions including Inc. Magazine’s “30 Under 30”; Fortune Magazine’s “40 Under 40” and “Most Powerful Women Entrepreneurs”; and Fast Company’s “Most Influential Women in Technology.”
Helpful Links
Fast Company: Inside Rent The Runway’s Secret Dry-Cleaning Empire
Harvard Business Review: Women-Led Startups Received Just 2.3% of VC Funding
+ Episode Transcript
[00:00:00] Jenny Fleiss: We saw the first girl pick out this gold sparkly dress. She twirled around in the mirror and she's like, "I look hot, "and she was transformed, she didn't want to take the dress off. And Jen and I, because, again, we were that end consumer ourselves, we related to that. This isn't about the cost or the convenience, all these things we were trying to test and learn in our model for the business. It was really about that emotional feeling of empowerment and confidence. And so, we're like, "That's what we're renting to her. She gets to be Cinderella," and we built the whole brand around that feeling.
[00:00:31] Jesse Purewal: From Qualtrics Studios, this is Breakthrough Builders. A series of conversations with people whose passions, perspectives, instincts and ideas fuel some of the world's most amazing products, brands and experiences. I'm Jesse Purewal, head of brand at Qualtrics, builder, coach, storyteller and your host. At Qualtrics, we're for breakthroughs and those who are bold enough to chase them. But when you're chasing breakthroughs, you've got to be thinking and executing at two speeds, the monumental and the incremental. The move by Netflix to go from DVDs to streaming or Apple's decision to invest in stores when eCommerce was replacing physical retail are monumental breakthroughs. They're the moves that defy convention and fundamentally reshape customer experiences.
But incremental breakthroughs are just as important. That's because, more often than not, change in a category or company is the result of reliably consistent steps forward. Those smaller steps may not always get the spotlight that the more daring, disruptive innovations do but they're no less critical. I believe that the most successful builders have a hard-earned yet deeply intuitive understanding of how to innovate to move the world forward, both monumentally and incrementally.
That's why I wanted to sit down with today's guest, Jenny Fleiss. Jenny is best-known as the cofounder of Rent the Runway. She's also a venture partner of Volition Capital, a New York based entrepreneur, a wife, mother, board member, advisor and relentless problem solver. She's helped create some of the most inspiring and inclusive innovations at the intersection of fashion, operations and technology over the past decade. Here's her story.
I am here with Jenny Fleiss. Jenny, thank you for joining me on the show.
[00:02:14] Jenny Fleiss: Thank you for having me.
[00:02:15] Jesse Purewal: Jenny, let me start with who you are. Who is Jenny and what's the place that you hold in the universe?
[00:02:21] Jenny Fleiss: Wow, big question. Well, I've always had an entrepreneurial spirit. I love noticing problems in the world and thinking of solutions. So, it's not just about identifying what's wrong but how can you make it better. And as I think back to the youngest ages, always trying to do that. I see it in some of my kids right now, which is very rewarding. But I didn't know you could be an entrepreneur as your career. I guess in some form, my parents, actually, were entrepreneurs and yet, I never really thought of that as a career path that I could choose. And so, it wasn't until later in life that it clicked, that I wound up starting a business and, subsequently, some others and feeling, wow, work is not work because I was just having so much fun doing it.
[00:03:04] Jesse Purewal: Talk to me about joining Volition Capital as its first venture partner and what it was about the match between you and Volition that made it a great fit?
[00:03:13] Jenny Fleiss: Yeah, I joined Volition about nine months ago and I'm their first operator on the team. It's a group that came out of Fidelity Ventures based in Boston, so I'm also their first New York City person on the team. And I think they really embraced the fact that I was different and wanted to bring that complementary skill set to the table. I, from Rent the Runway, very much realized how having an operational background, we were lucky to have a couple of our investors who came from entrepreneurship and seeing the lens that they had and how they could help and relate to Jen and I as we were building Rent the Runway was so valuable and important. So, I respected it and thought, one day, I hope to be able to bring that to other businesses as well. And Volition saw that and agreed and, I think, wanted to add that to the mix of their businesses and be able to offer that to the companies that they work with.
Volition is a growth equity fund which means that we are focused on businesses that are often a little later in their pipeline and stage, $5 million or more in a revenue perspective but, also, that have this proven, disciplined financial model that can work. So, it's got to have proven the fundamental economics are going to work. And in a moment where there's a lot of venture dollars flying around the market, question marks over how much it's inflated and is there going to be a downturn, I think it's great to be able to have that discipline [inaudible] you control your destiny and responsibly, manage money for all of your LPs.
In addition, I love that Volition really wants to make sure that none of their businesses are a zero. So, the way our model works is we want everyone to win. Ideally, they're winning at 30x but, sometimes, it's the 3x, the 5x and we will fight to make that happen. So, again, unlike venture where it's a 1 in 10 becomes a unicorn model that you're working towards, we're going to lean into the businesses that are actually, maybe, struggling the most and are really needing our help and support. And knowing, as a founder, how this is your whole world, I think, it's really important to know that your investor-partner alongside you feels as strongly about making this a success.
[00:05:12] Jesse Purewal: Yeah, I love that ethos around the founder should be able to go after their dreams without risking them. I think there's something really special to that. And when you think about US consumers, women account for anywhere from 70 to 80% of purchase decisions these days yet, depending on your source, only 2 to 4% of venture dollars are actually flowing to businesses founded by women which, to me, is an astounding and disappointing statistic. So, Jenny, what are the things that you think need to be done to close that gap so that the world starts to benefit more from the ideas that might, otherwise, be sitting on the sidelines?
[00:05:50] Jenny Fleiss: Yeah. So, I love that you mentioned these stats, it's something I talk about a lot because I fundamentally believe that the best businesses are created when you are the consumer yourself. So, you've seen and witnessed and become passionate about the problem that you're solving in a way that, because you're the consumer, it lets you revisit that problem and make sure you're continuing to solve it in the best way possible on a very regular basis. Point in case, Rent the Runway, Jen and I started that business, we were women in our 20s. We also had a lot of events, we wanted to wear great designer dresses and so, we very much related to the ethos of social media. Increasing the social pressure to turn over your wardrobe, increasing the importance of putting a great look out there wearing your best outfit.
[00:06:33] Kim: Hey, guys. I'm Kim, we're in Brooklyn, New York and come to my closet. So, this is my closet. This is where the Rent Runway stuff goes because this is what I use the most.
[00:06:43] Jenny Fleiss: The confidence that instilled in women-
[00:06:45] Kim: It is such a value added to my life, to how I feel, to how I show up. So, being able to access, literally, hundreds of designers that I would never have tried before because I was a fast fashion person, that is huge impact.
[00:06:59] Jenny Fleiss: And I think that let us build the best business that spoke to our consumers in the most natural way. It also let us continue to evolve the business over time. So, as we matured and had babies, we realized there was a maternity angle to the business-
[00:07:11] Speaker 4: I rented dresses for my baby shower and it's great that there's a section on the website. So, it was easy to see what was stretchy, what was bump-friendly in the different trimesters.
[00:07:26] Jenny Fleiss: ... bridesmaid angle to the business. There was an everyday use case behavior where our business evolved into subscription, which is the lion's share of the business, and women can rent for everyday. It could be a meeting at work that merits an outfit. So, I think only when we have more women starting businesses, more funding going to women, will we actually have problem solved in the best way and the best solutions to problems. And that doesn't just apply to women, I'd say it applies to all aspects of diversity. If you think of making sure that we're representing the actual true consumer base with investors, with talent, with founders so that we can accurately and passionately solve these problems.
[00:08:06] Jesse Purewal: And what kinds of businesses or categories or innovation vectors are really interesting and intriguing to you right now, Jenny, as you have your investor and advisor hat on? I know you've been advising early-stage entrepreneurs for some time. But as you look at, let's call it three to five years out, what's getting you most excited when this generation of entrepreneurs is coming to you and coming to the team to share their ideas and their ambitions?
[00:08:32] Jenny Fleiss: Yeah. Well, there's a lot of innovation happening right now. So, there's a lot to be excited about. It's a really fun time to be in the investor and advisor and board's role, because I get to see the whole landscape and all the innovation that was largely spurred on through the rise of digital commerce with COVID. So, a lot of what I find interesting right now is, okay, if the world is going increasingly digital, what are some of the backbone pieces that are going to be needed to support that? So, supply chain is very interesting. We know the supply chain, especially post-COVID is broken. The shipping ecosystem is under an immense strain and shipping prices have soared with a very small number of folks who are actually delivering shipping solutions, UPS and FedEx. And I spent a bunch of time at Rent the Runway leading our logistics team, so I have a special sweet spot for that.
I also find it really interesting to think about how do you, in a moment where there's so much innovation and you can put up a website same day on Shopify or, even on Instagram, you can start your own form of mini business, how do you really build a business that differentiates itself? And I think what I see is a deeper level of personalization and a deeper level of experiential commerce. And so, with personalization, you no longer just see algorithm showing me a unique homepage, you start to see one-to-one personalization where someone may take their aura ring which I'm wearing today and it's a business that I invested in. Or Vessel Health which is a strip that you pee on and it shows you your daily vitamin makeup and get the specific multivitamin for you, not just for someone like you. Or the specific sleep regimen and recommendations from my aura ring because of how I slept that night and the activity I had that day.
So, obviously, Cara Vitamins and all those started in one level but, I think, we're going into just the next level of this one-to-one personalization and thinking about how can that filter into other categories. So, there's a business called Supergreat I find really interesting because you initially go through a personalization quiz around your skin type, your coloring and then you get to see lots of influencers in the beauty category who are actually trying and using different products and you can walk through that tutorial, which bleeds into this area of experiences as well where shopping should be enjoyable as well, it shouldn't just be about getting the product. It's like, "Did I enjoy the time and can that be an actual enjoyable part of my day?"
So, those are a couple. I think the Creator economy is also interesting. So, this Shopify on steroids. What else is going to be out there that lets creators and everyday person be an entrepreneur that much faster and more easily to take advantage of this digital moment. And in a moment like COVID, just jump in and start selling day of and I think that there's more and more infrastructure enabling that. I could probably go on and on about all the innovation happening right now.
[00:11:11] Jesse Purewal: Jenny's hitting on a topic that both inspires and confounds many builders. How do you create a product or an experience that's incredibly personalized, yet not ask too much of a customer in terms of dollars or data to get to the right level of personalization? I wanted to ask Jenny more about that, given that she'd run operations and logistics at Rent the Runway, which is an incredible demonstration of personalization at scale. What advice do you have for them and how do you think about the privacy personalization tradeoffs?
[00:11:47] Jenny Fleiss: It's a great question. So, I'd break it into three buckets. The first is trust and how do you build trust from your consumer. A lot of that is in the work of branding and communications. With Rent the Runway, a bunch of our strategy was, can we build a brand that you hear about through your best friend or through a friend at a dinner party because that's a great anchor and way to build trust, to get questions answered, et cetera. The second pillar, I'd say, is transparency which ties into trust. I think when you're communicating and telling and letting people know how you're using their data, if you're using at all, I think that helps build trust and I think it's just the way the world is moving, that there's more transparency and control over I say yes to this, but I say no to that.
And then, I'd say the third bucket I think about is, ultimately, I think it's a trade-off between your privacy and your efficiency. And I'm a believer that time is the greatest luxury, it's the most scarce resource for all of us. So, I think at the end of the day, consumers, most often, will choose efficiency over the privacy within some reasonable constraints, we can't get people tapping into bank accounts and everything. And so, I'm more bullish on the fact that with the right tools and monitoring and control and transparency, I think consumers will continue to lead into the world of privacy sharing for the sake of getting better products that serve them in a faster way because you can more quickly identify the right product for a person if you have their information and having their life be more seamless.
[00:13:10] Jesse Purewal: Yeah, yeah. I love that you brought in the trust and transparency angles. I've heard you use the phrase disruptive commerce a lot throughout your career. You like to create new business models and you like to reimagine customer experiences which, I imagine, takes a certain degree of intestinal fortitude and courage. So, talk about how you cultivated that fortitude and courage in yourself and maybe what advice you're able to leave with investors as you counsel them in the roles you're in now?
[00:13:38] Jenny Fleiss: Well, first off, it's really fun to work on transformative business models. It's also somewhat necessary because it does take some time to get a business up and running and the world is moving so quickly that, unless you're thinking at least a couple years down the road, you may have already missed your window to service a customer need amidst the time that you're building something. There's so many entrepreneurs and funding out there. I'd say it comes back to, honestly, I'd say, first off, the way that I was raised, I was born in New York, it's the city that dreams are made of, I never felt like there was a glass ceiling. It felt like I could always dream super big and anything was possible. So, I think that probably rooted it.
That said, I was very lucky to have worked with two and, now, I think with Larry at Volition, a third person in my life that inspired and pushed me to dream and think big. And it's, all too often, I think, something that women are not as good at as men and why venture funding dollars still, very majority, goes to men. My cofounder, Jen Hyman, in Rent the Runway, is definitely a big picture visionary strategic thinker. And, from the beginning of working with Rent the Runway, I was able to start to see through her eyes and allow myself to think and believe in the bigger picture vision.
My skill set is much more around how do we get from point A to point B, so it's fun to think about the what ifs and what could happen. But then, how do we build these bridges to actually make that effective and often it comes in pieces. With Rent the Runway, we started renting black tie dresses and, now, we rent everyday apparel, even some athletic gear, jean jackets, handbags. And that was a journey that we went along with our customers and the brands that we work with in both the front-end consumer as well as the back-end process. We're evolving as we built the business.
Jetblack, the business I built for Walmart, I was lucky to have Mark Lowry as cofounder of that business and to work with him closely as he was the CEO of Walmart eCommerce at the time and he is very much a big picture thinker. He's building an incredible city of the future right now, you can't dream much bigger than that, but someone who sees where the puck is going a few years down the road. With Jetblack, we built personal shopping over text message and knowing that conversational commerce, being able to shop by asking questions as you would in a store, is going to be the future. It's like, "Well, how do you tie in to the way a consumer acts and behaves today in a way that's actually convenient and comfortable that's going to build the right datasets and technology to let you bridge towards a voice solution or better tech solution in the future?"
[00:16:13] Jesse Purewal: Rent the Runway really runs on a lot of data analytics and precision logistics. It's very easy to posit a brand on Instagram and the notion of direct to consumer and not really worry a lot about the part of the iceberg that's under the water or the duck's feet pedaling furiously underneath the water, but that was your jam and you're running-
[00:16:33] Jenny Fleiss: Yeah.
[00:16:34] Jesse Purewal: ... one of the world's biggest dry-cleaning operations and you build a warehouse management system from scratch. If folks don't have an appreciation of really what operational tenants are required to run a business like this, what's the best way to upskill? What's the best way to build the team? How do you really build a D-to-C at scale beyond what we see on our screens?
[00:16:56] Jenny Fleiss: Yeah, it's a great question. Well, I joke that I drew the shortest straw with leading logistics at Rent the Runway because, in earnest, as a founder of a business, you do whatever needs to get done most that day. You're constantly drinking from a firehose when the business is growing so quickly. And I think part of the beauty of being a first-time founder is you're somewhat naive. So, when Jen and I started Rent the Runway, we didn't have tech, fashion or logistics experience. I definitely never thought I would be running logistics and, in the process of hiring and building out teams, it wound up being the most complex area of the business as well as an area that was just really hard to hire for.
And the reason for that was, we were forced to dramatically innovate in that category because there was no reverse logistics at scale, especially in the garment world. The closest that we could find was Netflix, which at the time, was still doing physical discs and DVDs and they had built all their own custom proprietary technology and warehouse management systems to do that, and good luck pulling, really, anyone out of there to help do it.
So, in some ways, it was a detriment if you went and hired someone out of an Amazon or McMaster-Carr more traditional warehouse background because we needed to do things really differently and to think with a super open mind. And coming from a very different background, I had worked in financing consulting before, I think it gave us that, "Okay, here's the problem we need to solve." There's many paths and routes to solving that, the open mindedness to test try, fail, learn and then, ultimately, to evolve and build systems that we do have a lot of amazing experts that have taken that business and that part of the company to the next level now.
[00:18:32] Jesse Purewal: I think to go on a learning journey like that, where you weren't an expert or someone who studied logistics and systems earlier in your career, you really had to have been galvanized around the mission and the vision that you had for the business. I think of things like empowerment and discovery and inclusivity and access and I love the turn of phrase you used around it's the kind of brand you would learn about from your friends. But give me the view from the founder seat on that. What was and what is important to you to have at the heart center of the Rent the Runway brand?
[00:19:05] Jenny Fleiss: I think it stems from the initial work that we did 12 years ago when we were starting the business. We held trunk shows at different college campuses and, at that point, the business was still nascent enough and we were early enough in our journey that we had a really open mind, when we went to these trunk shows, of learning and observing from our customers and that became such a core foundation of our culture, our values of the business and still something, I believe, makes for the best companies.
We saw the first girl pick out this gold sparkly dress, she twirled around in the mirror and she's like, "I look hot," and she was transformed. She had a better posture, her confidence, she didn't want to take the dress off. And, Jen and I, because, again, we were that end consumer ourselves, we related to that. This isn't about the cost or the convenience. All these things we were trying to test and learn in our model for the business, it was really about that emotional feeling of empowerment and confidence.
And so, we're like, "That's what we're renting to her. She gets to be Cinderella. She gets to feel that feeling for a night or day or whatever it is," and we built the whole brand around that feeling. And, that, I think has been what has driven the whole team and the company from that moment onwards and the logistics was a piece of getting that done because logistics is the last touch point with the customer of how are you going to present an aspirational experience that people want to talk about and will make them feel empowered.
To a customer, it's like, "Well, if you don't own logistics and you don't take control of that process, then you risk putting the whole brand and that whole value proposition to risk." So, it quickly became and it felt like the most important piece of the business. It's fun, though. We started, actually, running that out of my local dry cleaner. I was trying to learn about how much would it cost to dry clean the dress, I noticed he had an empty rack and I was like, "Can we store our dresses here?"
We used it as our warehouse and we learned a lot about dry cleaning and logistics and all that while being trial by fire. And the whole team, at 4:00 every day, would go from the office to the warehouse to pack boxes and I think that started a journey of just being really hands on with, really, every piece of the business. But certainly, the logistics is something we decided we wanted to own and evolve and is now a core competency and, I'd say, a real competitive barrier to entry for us.
[00:21:14] Jesse Purewal: Yeah, it certainly is. We talk about breakthroughs on the show, incremental and monumental. When was the moment that, beyond any reasonable doubt, you knew that not only was the idea of renting a dress from a designer label for 10 cents on the dollar an interesting and provocative idea but, actually, one that you could build a thriving business around?
[00:21:39] Jenny Fleiss: I think my initial reaction was, wow. I don't know if you ever know. And yeah, in the sense that every time I even pass a Rent the Runway garment bag, I'm still delighted and tickled and I'm like, "Wow, this is working. This is a thing." Or, when you see brand awareness studies or the more people you talk to that know about the business and the brand, I think that starts to make it tick that you'd really broken through to enough people.
But at least for many years, it was just this hunger and this fire of being heads down, laser focused of, "Will it work? I got to make it work," and just plugging away at that and never resting on your laurels or assuming that, because you had a million members or 2 million members, that it was working. You want it to make it work better, you want it to service more people, you want it to constantly learn and evolve.
And I think one of the gifts of entrepreneurship is that learning process, learning from your consumers and then getting to learn about something like logistics, which I would have never otherwise stumbled into and, certainly, dry cleaning, in my career, in my life. But for the fact that I had to figure it out. And through that, I actually met Mark Lowry and Nate Foust, who I later worked with as well. A lot of people who helped teach me because they were dealing with the same questions and issues in their own businesses and entrepreneurial journeys.
[00:22:48] Jesse Purewal: Talk to me about the dynamic with a cofounder, particularly someone that you're with, from the very instantiation of the idea and take me behind the scenes of it. The stuff you don't read about in the books or the stuff that isn't as obvious in the onstage interviews. If someone is trying to think about, "Boy, I really want to partner up with this person. But I need to check on X, Y or Z," or I'm thinking about, "I need more help in a certain skill set. What has to be true about that dynamic, as you experienced it, that you're either really glad was there from the outset or that you had to actually work on and develop in your relationship with Jen as you went through the growth arc of the business?
[00:23:29] Jenny Fleiss: The first thing I'd say is we had, almost in retrospect, the ideal setup for finding a cofounder. We went to business school, we found ourselves in the same section at Harvard Business School, so a group of about 90 kids. The whole year, you take all of your classes together and the classes are business case studies. So, every single day, you're spending, probably, three or four cases a day and you're digging into a problem that a business is facing and the class is run, essentially, by the students. So, the teacher prompts it but then, it's all a discussion format of different students being called on. And so, you very naturally get to understand from a work smart perspective how different people think of an issue, how you respect one another and the different skills you bring to the table.
And so, that was the origin of both our friendship as well as how we got to know each other within this work businessy construct that very naturally, without any presuppose, "Hey, we're going to start a business together next year," let us unpack. Did we enjoy spending time together? Did we respect each other's feelings and opinions of different businesses? Did we have complementary skills? How would we work together? So, it reduced some of the risk factors and made for a very natural, fertile ground that when, during the second year, Jen started talking to me about this problem that her sister, Becky, had encountered where she'd bought a $2,000 dress and it made absolutely no sense.
[00:24:51] Speaker 5: This is all of my closet and I wear, probably, 20% of this, not even. This still has its tag because I've never worn it and it was $260, which is pretty expensive for a dress that I've never worn. So, it's going to go back in the closet where I won't wear it.
[00:25:11] Jenny Fleiss: And Jen was speaking with this passion around we could rent dresses and I immediately went to some of the what's happening behind the scenes with the designer industry and fashion. How do we make this work? What should we do next to see if this will work? It all came to life very naturally, I'd say, and that was the greatest gift. To be set up in that ecosystem with professors around us that we could, then, go and talk to to learn about something or get an introduction or to vet the concept a little bit further with our logistics professor, with our marketing professor, finance professor, et cetera. And it, also, I think, was this [inaudible] this fertile brain space where your thinking in this business context, you have enough time on your hands that you can make space to, in a smart way, work on a concept in a business like this.
Jen is this big picture, strategic visionary and I'm how do you get from point A to point B and that came to life pretty clearly and pretty quickly. But I also think it's super important for folks who consider starting a business with a cofounder to do an MVP test, a minimum viable product test and you do that for a couple reasons. You do it to better hone what your concept is and to make sure customers like it, hopefully they love it and are obsessed with it, to unpack insights, like I mentioned, where the girl is twirling in the gold sequined dress and she's emotionally changed by wearing designer fashion. But I actually think the biggest gift and the reason to do it is to see how you work with your cofounder and to see if you, yourself, like spending time in this way.
So, by virtue of putting out a trunk show, we were renting dresses to women, we had to realize, "Okay, we're schlepping dresses to a dry cleaner, we're setting up these racks of dresses, we're interacting with customers. How are you sharing the workload? Who's doing what? How are you acting as a team?" And then, "Am I enjoying this and what parts of this am I enjoying?" So, it gives you a test drive, essentially, into starting this business with that person.
[00:26:58] Jesse Purewal: I'm imagining, too, as you're searching for capital, and now you're doing this on the other side of the table, that one can read a room reasonably quickly and find either synergy or lack thereof and be entranced by that. That, if I'm wondering whether to deploy a few million dollars to you early in your journey, if you're finishing each other sentences, there's a certain degree of confidence I can get around-
[00:27:22] Jenny Fleiss: Absolutely.
[00:27:22] Jesse Purewal: ... what you believe as well as having that diversity of perspective and background and opinion like you talked about. You weren't in the same skill set, you were really nicely complementary and I think in a probably cool and fun way.
[00:27:34] Jenny Fleiss: Yeah. Early on, you're investing in the team, I'd say first and foremost, in the people. So, seeing that that dynamic were poor, the complementary nature is ticking is super, super important. I definitely think that. It's also important that when you're chatting with the investors, you're thinking of them as your cofounders as well, to some extent, especially your early-stage investors. You are stuck with them for a really long time and doing the same leg work that you do with your cofounder through having them make introductions, like your test driving this relationship in a way. Like, "They say that you've got a great network, can you introduce me to this person?" Don't wait till you've signed a term sheet, like, "Let's get going."
And then, they really respect if you are the type of team and people going and making stuff happen. You're not just writing a business plan, you're not just sitting behind a desk, you've seen what customers need and want. And, without any dollars at that point, you're making some traction and building something.
[00:28:25] Jesse Purewal: And how would you say you helped move the investment community's perspective on the possibilities for this kind of business forward as you went through the different funding cycles? I know in early conversations with investors, you would sometimes hear things as ludicrous as, "Oh, well, I'll ask my daughter if this is a good idea," or, "I'll ask my EA if this is a good idea." And at some level, you must have been completely flabbergasted that you were getting that kind of feedback. But on the other side of things, there's a little bit of that, "Well, this is the water we're swimming in this investment world."
But over time, I think Rent the Runway has been a non-trivial part of moving our societal perceptions of not just women run businesses, but the idea of bringing something into the world that could be around fashion and confidence. What is the mark that you would say you're proud to have left on the world from the perspective of how you've shifted perceptions on the possibilities of this brand in business?
[00:29:23] Jenny Fleiss: Well, that's so kind of you to give us credit in that way, it's very humbling. I've certainly seen more female entrepreneurs and stats, while moving very slowly, have gotten marginally better and it's part of why I'm excited to be doing investing and advising in this chapter and to have seen so many people who worked with us at Rent the Runway or who were customers at Rent the Runway going and starting businesses themselves and this great multiplier effect that, I think, it's showing can be more powerful than telling. I think, for sure, in pitching to those male VCs, it was, yes, frustrating when [inaudible] ask their assistant or their wife about the concept, at the same time, appreciate wanting to really, from the consumers lens, understand the value proposition.
And so, doing that work in that diligence now as an investor is critical. You're not always going to be the end consumer yourself, so you've got to find that touch point. I think the struggle for us was that, if it was someone's daughter, they were typically too young to be really our target demo and if it was someone's wife, billionaire VC, they often weren't exactly our demo either. Often, the assistant wasn't exactly our demo. So, we found a lot of success in showing rather than telling. We would start our pitches off with videos of these trunk shows that we had done where the women are talking about how they feel transformed and how fashion makes them feel.
So, it started to let them, through these customer testimonials, do the diligence of understanding the lens. And we would, then, offer to make introductions to different customers or people who we had spoken to so that we could make it easy for them to put themselves in the shoes and the mindset of the customer.
[00:30:56] Jesse Purewal: I want to ask you about growing women leaders and being intentional about that early in a girl's life. If you're talking as a business builder and, now, also as a parent, to parents or families of girls, what would you say to them about the kinds of experiences that you would wish for their daughters to have early in life or the learning journey that they should go on to help them dream fearlessly and feel like they can make a dent in the world the way that you learned to dream early on?
[00:31:23] Jenny Fleiss: Wow, it's such a big question and something I feel hardly an expert at. My children are almost 10, six and a half and five, two girls. So, I have a 10-year-old girl and a 5-year-old girl. But for my son, I think of just as equally, as how do I inspire them all to dream big, to think in an entrepreneurial way and to build the right foundational skills. I think first and foremost, seeing that their mom works and explaining to them what I do. They think it's pretty cool. I've taken them all to the office, they have met a bunch of people. I'd say it's more of a blend than a balance. So, I try not to make it an either or, I try to talk to them about what I'm doing. And, lo and behold, I found this with my firstborn, starting around age five, she actually got it and she understood I was going to a speaking event and was speaking to a female audience. And so, she was really upset that I was leaving.
And when I explained what I was doing, all of a sudden, wow, that was worthwhile and that was meaningful what I was doing and it was cool and fun. And so, I love that she sees that women can do this and, also, can have fun with it. That it's a fun industry. Fashion is fun for most every little girl and that you can work on something fun and enjoyable and that you can be really proud of. And I try to tie that back to even just every day schoolwork that she's doing and feeling the accomplishment of trying your best and learning something and the joy of learning. Storytelling about something like dry cleaning, which maybe wasn't always the most interesting thing to learn about, but it can become that and it can still be valuable or you can find value in the relationships you build while you learn about something.
The other thing we've done is they're fascinated by entrepreneurship. I think kids these days are more fascinated by entrepreneurship generally. And so, we started a couple of businesses. This trend started a little bit when we were in COVID and there was, first, a mask business my daughter started and we did it on Instagram. And then, there was a children's business where we're selling products that you would redeem points for that you earned from your parents. And I worked on both of them with my oldest daughter and, actually, my other children got involved as well. And I think seeing, first of all, how hard it is and all the pieces that are involved in it, it's like a lemonade stand on steroids. And I ran a ton of lemonade stands, that was my childhood favorite thing to do that my parents were incredibly supportive of. Helping me bake and lug all the supplies and prep all the signs and everything.
And so, we do lemonade stands, we do some attempts which some things work well, some things don't work well with the startup. And so, I think they're getting to sample and taste it and, also, to understand sometimes you fail, sometimes you decide to abandon ship on something, doesn't mean you can't try something new. And I think one of the most important skills of entrepreneurship and probably life is trying to look for and see the silver linings or the positives and the good pieces. It's like, you had a bad day at school, was there something that made you smile? Was there some interaction you had that was good? Looking for those pockets of optimism.
The dream big thing, yeah. Again, I think it can happen in just the imagination of every day. So, even if you're doing imaginary play with a young child or, sometimes, it's the moment where you say, "Oh, you think this is an interesting idea? Let's go work on it," and you just let them live like, "Why shouldn't you be able to do that?" I remember one day my daughter was learning about Jane Goodall at school and I'd bought a book then we started reading it at night and she became fascinated. And we started looking at her website and I said, "Oh, sometimes she speaks at different events in schools." She said, "Would she ever speak at my school?" And I was like, "Email her," and we did. And she didn't come speak at the school but it was there's no bar. I emailed Diane von Furstenberg to start Rent the Runway. It's like, "Why not?" Right?
You never know until you've tried and so, I think little things like that, that let life be optimistic fun and give people that permission to just go for it and, worst case, you have a great story and a laugh.
[00:35:01] Jesse Purewal: You said blend more than balanced, I totally resonate with that. But it also sounds like it's really a one plus one equals 10 or 15 situation to have your family close to your professional building efforts. And you're probably getting some interesting feedback from the kids along the way about what they think is working and not working with either your routine or what's happening with the businesses that you're part of?
[00:35:24] Jenny Fleiss: Yeah, they love giving feedback. I also think it's great from a setting examples to other employees and the tone of the culture to have kids at and around the business. So, that's been an important piece as well. But for sure, being a mom and having kids has contributed to my entrepreneurial journey and, I'd say, success as a business leader. First off, I give the example of going through pregnancy. You're wearing maternity dresses, you launch a maternity collection for Rent the Runway or what have you. The more of these consumer touch points that you can see, the better you are able to innovate. And in that sector of women who are making purchase decisions, moms are a really big percentage of that.
So, having kids immediately let me connect with this whole other segment and to see the need for a service like texting to order, reorder your paper towels or diapers and using one hand because your other hand is full with a child that I related to because I am a mother.
[00:36:17] Jesse Purewal: Yeah, I can relate. On August 27th of 2014, I was in a segment of people who support a pregnant spouse. And on August 28th of 2014, we became twin parents and, all of a sudden, we were in a much different segment and needing much different things in our lives.
[00:36:35] Jenny Fleiss: A lot more things that you-
[00:36:36] Jesse Purewal: A lot.
[00:36:36] Jenny Fleiss: ... need in your life.
[00:36:37] Jesse Purewal: Yes, and it's more than two X everything. Just-
[00:36:40] Jenny Fleiss: Yes.
[00:36:40] Jesse Purewal: ... so once clear. Well, Jenny, I want to close with the lightning round, just a-
[00:36:44] Jenny Fleiss: Yeah, I love it.
[00:36:45] Jesse Purewal: ... couple of quick ones and want to get your first take on these. What's a book that you love to recommend to people?
[00:36:52] Jenny Fleiss: Delivering Happiness. It's the story of founding Zappos.
[00:36:56] Jesse Purewal: Give me a brand you admire. One that you personally can't imagine living without.
[00:37:01] Jenny Fleiss: it probably changes depending on what I'm going through at life and with my kids and what they need. I use FreshDirect on a very regular basis. There's brands like Lululemon that, for me, I think both from a female empowerment as well as having very versatile clothing that make it easy to feel comfortable and get out there and talk [inaudible] .
[00:37:21] Jesse Purewal: And how do you describe your secret sauce? The special blend of stuff that makes you do you?
[00:37:26] Jenny Fleiss: Highly focused on efficiency. I call myself a creature of convenience and that I will soon prioritize eating whatever's in the fridge or going to the closest coffee shop versus the best coffee or what have you. But more often, it's in trying to manufacture some of the efficiency and structure my day and my time in a way that's really guarded and thoughtful. So, that's definitely one.
I really enjoy connecting people to give them new opportunities and learning. And I think it's, in part, developed because my energy is having that insight of, "Ooh, you should meet this person," because, for Rent the Runway, that was transformational. We probably had about 80 meetings in the first several months when we started Rent the Runway and you often enter them and you don't know where they're going to take you. But usually, you build a relationship and they take you somewhere great and I don't think we could have built the business without people like Diane von Furstenberg who responded to our one-off email or Mark Lowry who responded to my question about logistics and Elie Seidman who was starting a business at the time. I just think you need this deep bench of a network and I'm glad to try to pay that forward now.
[00:38:28] Jesse Purewal: What's your go to exercise regimen?
[00:38:30] Jenny Fleiss: I love running. I've always been a runner, more of a jogger than anything. And one reason I love it is I took a running meeting with someone this week even and it was someone I've never even met before. They saw that I like to do running meetings and we have a great chat while we got our workout in. This morning, I did a walking meeting with someone else. So, I love trying different workouts and mixing it up and pulling other people into it with me.
[00:38:51] Jesse Purewal: All right. So, my last one to you is a little bit of a curveball. I heard you say in a conversation you did with Rebecca Minkoff on her podcast a little while back that you are a big practical joker.
[00:39:02] Jenny Fleiss: Oh, yes.
[00:39:03] Jesse Purewal: That you like playfully joking with your team or your family. I want to turn the tables on you. Give me a time when somebody flipped the script and got you with a practical joke of their own.
[00:39:14] Jenny Fleiss: Oh, my goodness. My kids are always trying to do practical jokes. They've used fake dog poop on me in the spot that they know my husband would get annoyed with, I more often use that one on him. But that's definitely happened. I don't know that they've yet to get me with what I'd say is a really good one. But yeah, there's little things. You're about to get out into the soccer field after driving there and it's like, "Oh, I forgot my soccer shoes. Just kidding." I think just anything you can do to bring a little lightheartedness and fun to the everyday is why I love impractical or practical jokes as the case may be.
[00:39:50] Jesse Purewal: Listen, this has been terrific. I'm so glad for the chance to have sat down with you and heard your perspective across a wide range of, I think, really interesting and important topics. So, wish do well with absolutely everything and I can't wait till we can do it again.
[00:40:03] Jenny Fleiss: Thank you. Likewise. Thank you for having me on. This is really fun.
[00:40:07] Jesse Purewal: Thanks for listening to Breakthrough Builders. If you're enjoying the show, please subscribe and leave a rating and a review and tell a friend about the show. Breakthrough Builders is a Qualtrics Studios original hosted and executive produced by me, Jesse Purewal.
An awesome team of people puts this show together including our show writer Todd Bagnull, folks from StudioPod media in San Francisco and Vayner Talent in New York. From StudioPod Media, our executive producer is Katie Sunku Wood, producer is Sterling Shore, editing and music is by Ryan Crowther and our show coordinator is Kela Sowell.
From Vayner Talent, publicity and promotion support come from Samantha Heapps, Hannah Park, Lindsey Blum and Ivanna Lin. The show's designers are Baron Santiago and Vansuka Chindavijak. Our website is by Gregory Hedon and photography is by Christy Hemm Klok. Special thanks to the entire Breakthrough Builders crew at Qualtrics including Ali Rohani, Ben Hawken, John Johnson and Kylan Lundeen.