How Jenny Fleiss Built Rent The Runway | The Further, Faster Podcast

Welcome back to Further Faster. I'm your host, Jeff Becker. I'm a general partner here at Antler in New York City. This is the podcast where we talk about bringing great ideas to scale. And if you're loving the show, don't forget to like, subscribe, and share so we can bring more great operators and more great investors on the podcast to talk to you.

Today on Further Faster, we're fortunate to have Jenny Fice, the founder of Rent the Runway and storyried investor at firms like Valition Capital and Initialized. Today she's getting back into the founder journey with a new set of co-founders, her kids, with Ro Ryder. But today we're going to hear all about what it takes to build an iconic company, invest in the early stages, and get back in the trenches to build for another time. Jenny, thanks for being here.

Yeah, thank you for having me. So fun.

Um, you've obviously you've built one of the what I would call few iconic companies in New York.

Thank you so much.

I mean, everyone I know loves it and I would love to hear just the story of Inception, the very beginning. Um, maybe you can tell us a bit about how you guys came up with the idea, where you started, just founders a a sense of what it's like in the beginning.

Well, thank you. It's been such a gift of a journey and there's so many chapters of founding businesses, but I definitely relate most to all these early stage founders going through the many questions and triangulating trying to figure things out. Um, we started Rent the Runway, my co-founder and I, when we were at Harvard Business School, and it came from a simple lunch conversation where my co-founder, Jen, um, her sister Becky had just purchased a very expensive dress, an $800 dress from a top designer brand. And Jen was telling me the story about how she was criticizing her sister who spent this money frivolously at a moment when she really didn't have the income and the resources to be doing that. uh and her sister had said a couple of things which were very funny but also telling of the moment that we were living through. It was 2008 at the point um and it was a recessionary moment but it was also a moment where social media had really started to take hold at an more aggressive level and I'd say today it's 10x that. Um but the things that Becky said was first off all the dresses in my closet are dead to me because I've been photographed in them and they're posted on social media and I can't possibly wear them again. So, she bought an expensive dress even though she had a lot of dresses she could wear because she knew that she was putting her brand and her statement out there in this indelible way with a broad audience and that it wasn't as easy to repeat an outfit. And the other thing she said was, "I might meet my future husband at this event that I'm going to." The idea that when you're in your 20s, you might be at your lowest income earning level, but you're actually going to a lot of events and you're at these like high stakes moments of your life. So the investment essentially in yourself and in your future and in this brand building could be seen as really worthwhile. And when you think about it, that discrepancy between your lowest income earning moment and the number of events and the theoretical importance of the events is kind of the greatest pain point in your 20s. Um so that was kind of the initial conversation that sparked the genesis of Rent the Runway.

That's amazing. And so uh maybe just before we jump into what you did first to start the company, you have to find a co-founder. You mentioned your co-founder, you mentioned Jen and Becky. How did you decide who to start with and if that was the right team and or was it more natural?

Yeah. Um, it was pretty natural. So, one thing that was fantastic was Jen and I had met at business school and we were in the same section, which means it's a group of 90 students who during your first year of business school, you spend really every hour there together. You're in the same room and your teacher cycle through, but you're going through case method studying and teaching, meaning that you hear about different examples of businesses and how different business problems were tackled. And then you and your peers in the class are actually responding and commenting as much or more as the teacher. So, the teacher is guiding the conversation, but you really are back and forth with other uh form of colleagues at your business school. And so, it's a chance to really see how you think and how other people think. Um, and you naturally get a sense of who could be a good complimentary skill set to mine. Who do I really respect? Do I think they're smart? Who could I work well with? And I think Jen and I had very organically therefore seen, you know, she comes from a sales and marketing background. I came from more of a finance, strategy, consulting background. There was a lot of nice synergies. And then in our free time, and the lunch conversations, we got along and um, we had some similar ambitions in terms of the types of jobs and careers that we were pursuing. Um so I think this mix of finding people who you want to spend time with because it's a lot of time and that you know you can get along with um people that you respect and then people who have that complimentary skill set is really important.

Amazing. And so what is the first thing you do? Did you bring this to a Harvard class and pitch it in front of all your friends or did you did you build something like what was actually the first moment of of you know momentum for you all?

Yeah. Well it was lovely in business school they have independent study that you can elect to do. you can find a teacher and you can kind of as a course credit you can work on your startup and so we immediately decided that we would spend real time um working on this concept and that gave us the ability to find a an amazing teacher who was a mentor to us we had Francis Fry who's like a legend in all things operating but also just culture and and the principles of running a business uh and we therefore had this kind of built-in time in our schedule to spend time and work together. We also structured the classes that we were taking to be classes that we knew would be helpful. So, entrepreneurial finance, uh, entrepreneurship and the law. And I always say, you know, I had my notebook for things I was learning for Rent the Runway and then I had my class notebook, but there was almost everything was almost like a crash course in in work for the startup while we were actually also getting course credit and and and learning real skills. So, it made it that much more impactful and meaningful to be taking a course that was directly relevant to what we were doing at any given day in our startup. um we decided as soon as possible to start testing the concept out with consumers and also with the designer industry. So the concept of rent the runway which is renting designer apparel, we started with dresses, now we have accessories, jeans, handbags, you name it. Um, but it was really this two-sided marketplace, right? We knew we needed the customer to love the concept and the pain point existed, but like what could make them feel this was cool and fun? We needed to test that and then we needed to build the relationships and understand how to get the supply, the actual product, the clothing from designers and make sure that they were comfortable and excited to work with us. So, we right from the get- go, like literally day one, even when we were sitting at that lunchroom, started reaching out to designers and to potential customers.

Got it. And what's the pitch to the designer?

Gosh. Well, the first person we emailed was Diane von FFenberg who is like a legend and I had her email or I thought it was and hoped it was her email through like a distant contact who was on some not-for-profit board and um she responded within like a couple of hours and she actually said come to my office tomorrow at 2 p.m.

Incredible.

And and this is like Thursday at lunch that was Friday. We're like is this really her? Her message was in like large pink bubble letter. was a very weird email. And I think the email was something like dvfaol.com. It could have been anyone. And so we're like, well, sounds like a fun adventure worst case, you know, like why don't we go and try? And the idea was literally so fresh at that point that it was like on the drive to New York that we were, you know, we were all decked up in our Diane vonfenberg dresses and such. But we were actually kind of still formulating what was our pitch. What were we going to say to her? And the the first meeting, she actually took an hour and a half with us and she was like so lovely and kind and warm for most of it, but pretty clearly hated our concept. And it turned from this, you know, supportive female woman and mentor from the beginning to the more she dug into the business, it was clear that like this was going to be a real challenge to get designers comfortable. She was worried about cannibalizing her sales. Like why would people rent? Why would people buy if they could rent? She was worried about, you know, what is the perspective, the reputation? She's built this brand over decades. Can rentals still be seen as high-end and premium and designer and so like what is your website going to look like? People were at that time, 2008, 2009, just starting to go online to begin with to sell, let alone to rent. So there was a lot of caution and care about cannibalizing sales, but also that brand image and reputation and how she could retain control over that perspective. Um, and so after we left that meeting, honestly, I was like, well, that was interesting. She was nice, but like, okay, that was fun for a day or two, you know, to work on, but I felt like actually there was just too many holes that she had poked in our concept that it it meant we couldn't really proceed. Uh, whereas Jen, and this is part of where having a co-founder is great, she was like, "What are you talking about? She told us all the things that were wrong with our idea. So now all we need to do is adjust our pitch, fix those ideas, and like we have the template, the solution of of how we go back and we pitch again. Um, and so she did agree to meet with us again. And so a couple of weeks later, we came back and she was going to cancel the meeting. She tried to cancel the meeting. We had a whole moment where we pretended we were actually the phone was getting cut off. We're like, "Oh, no, no, we're in the lobby." And then like hung up the phone, but she was trying to cancel the meeting. And when we came in that time, we had edited our pitch to be all about experiential marketing. So what we had heard from Diane vonfenberg was that her customer was aging out. That her customer was now in their 50s and 60s. Her customer wasn't buying a lot of the more editorial styles like they weren't buying the prints and the hot colors and the one shoulder. They were buying like the little black wrap dress. And she wanted a way to get these exciting, interesting styles out there. She wanted a way to attract and engage a younger consumer and stay relevant and interesting and fresh and on top of the trends. And she actually wanted to get her product out on social media. So social media could have been this amp, you know, this megaphone for any cool girl who we were getting to try out her product to then spread it even more. Um, and if at Rent the Runway you were renting the hot pink one shoulder dress as opposed to the black wrap dress, it was a way to get some of her cooler, more editorial styles out there. Let alone the fact that if you do put a young woman in their 20s in an amazing Diane von Fenberg dress and they can feel the difference of designer fashion then when they can afford to buy something they are more inclined to consider Diane or a designer than Zara H&M. So we're like you know what your biggest competitor isn't cannibalizing your sales via rental it's fast fashion. Um, and so our pitch became around that. We we realized and understood that the fear factor that the opportunity was they were losing sales to fast fashion which at that recessionary moment for designers was the only category that was actually growing. And so that if we could reorient and say this is a way to acquire a younger consumer and introduce them to your brand in a positive way that it was a customer acquisition tool and it had a lot of brand building potential.

That's amazing. There's a lot of nuggets in there for founders to pull out from the cold email just shooting your shot to reframing objections as needs.

Yes, totally. And listen, you know, listening and, you know, making sure you take the time to find all these stakeholders and and take time to listen and hear them out and then frame your pitch to the specific person that you're, you know, you're speaking to.

Was it just was it one email to DVF or did you guys

Well, that that conversation was really from one email. I think we tried a bunch of iterations of the email just in case. Um, but subsequently thereafter you know, we were lucky she made some introductions to other people in the designer industry cuz we didn't have fashion or technology background. Um, and then we con we just continued to network. So the same way we had gotten to to Diane we found you know a dozen more and sometimes you know a random meeting would actually be like oh my cousin knows someone and works here. Uh, and like we chipped away chipped away and it did take about 10 meetings with a designer until you got one yes.

Wow. So the idea I mean for example even Diane after building the relationship she didn't work with us for years. So we got her blessing that okay now she understood why we were doing this and there was a chance that this could work but she wasn't signing on to sell us her inventory so that we could rent it. Um, she was um a mentor and guide at points along the way but it took a while to build comfort. So we had to knock on a lot of doors and take a lot of pitch meetings where it was like no no no and 10 nos to every one yes.

Yeah. How do you think about that as an investor now looking at founders at that same stage and their level of resilience on the nose or creativity on reaching out to DVF like how do you think about those early days and what that might have taught you about what to look for?

Yeah, I mean it informs it a lot and when I look for a founder right now I think resilience, the positive outlook, the optimism is really important. Creative problem solving of you know whether it's reframing your sales pitch or how do you get to a designer that you're pitching? Um, sometimes I, you know, I I talk to the folks at HBS or other schools and I'm like, have you guys made it too easy for entrepreneurs now? Because I think part of this is like you need people who are ready to to fight through a lot of obstacles and a lot of hurdles and who are just willing to kind of take on the next hurdle again and again, even though it feels like there's 10 doors slammed in your face, to still believe that that 11th door might like lead to an opportunity. Um, and yeah, I think that like the resilience, the optimism, the grit, the resourcefulness, creative problem solving, those are like the foundational things of what it takes to be an entrepreneur.

Yeah, I I imagine you may have had more door slam in your face than other people with a direct to consumer business, the opex of running a business that has physical goods, the logistics component of it. Uh, it's not the typical thing that a venture capitalist would look at and say, "Oh, that's software. That's high margin.

That's, you know, a playbook we've run before. How did you navigate that? How did you think about getting the first capital in the door and and getting some of the first yeses?

Yeah, so the venture capital side was interesting for sure. There was a lot of, you know, most VCs are are men and still to this day and most of them that we were pitching were men in their 60s. So, they were definitely not our core consumer. In fact, there were many that we were pitching where we had to explain words like accessories, right? Accessories are bracelets and jewelry and handbags. And if we talked about that, we'd have to like, oh, like you're scratching your head. We have to define that. So, there was it was a real gap in our core consumer and the people we were pitching, which was one thing we really had to create strategies of like how do we show we video testimonials of customers? How do we show this painpoint, make them feel it and understand and relate to it. Um, so that was one hurdle. I think the other was there was some perception of that like, you know, the world of fashion can be seen as something like cute or light-hearted and like there's like these two women, you know, coming in and pitching in in their dresses and like, oh, this is like a cute fun concept, but like didn't take us seriously enough, right?

You're going to IPO, you know,

right? And I think that that sometimes though is the difference of knowing which investor is your fit. just, you know, like just you you you can't take money from every single investor and not everyone's for you. But it was often pretty quick to see like who took us seriously and digging in and asking the real legit questions and pushing on it. And you know, some investors who were a lot more inclined to like try to call their teenage daughter or call in their secretary to see like their perspective, but like you know, they they didn't really feel to be asking and pushing the hard questions around the numbers and the margins and the operational details you're talking about. Um, the one of the investors we were lucky to meet early on though, Scott Friend from Bane Capital, he did wind up investing in us. Um, and he from the get-go asked all the right questions, all the hard questions. He was introducing us to folks like Mick Mounts who had started KA systems which was like early robotics where that was then bought by Amazon and Zappos. Um, and so like once you have people that are like oh yeah like a lot of this business is going to depend on the operational complexity and they realize that and you're like okay this is the type of person who can both be helpful to me and who's taking this seriously.

Yeah. How you mentioned investor founder fit. What was it like? Is it is it hundreds of meetings? Is it how important is it to get that right? And how important is the volume and how do you get to that first moment where you say someone believes in me enough to give me capital to go chase this?

I mean it varies on the number of meetings. One thing that I felt was important was to set like a timeline. I say to this to a lot of founders like you need to hold yourself accountable because the biggest asset that we ultimately have is our own time. And so Jen and I had other jobs that we were going had planned to go do after business school. And so I said if we don't raise capital by the time that we graduate then I'm going to go take that other job. And so that became this like work background timeline for us to say, okay, if you got to have money in the bank by, you know, let's call it June, how many pitches do you need to get, you know, to to get one term sheet? How many emails do you need to send to get the meeting to potentially get to pitch the partnership? And you back into that and you kind of wind up with this like weekby-week playbook. So So that's kind of how I organize, you know, Jen's strategic big picture thinker and visionary. And I'm a lot of how do you get from point A to point B? So I organized us around this like every week and even every day there were kind of like these milestones and things that we needed to do to incrementally lead up to raising capital. Um, for us we wound up meeting with I'd say maybe it was somewhere between 40 maybe 50 investors. Um, a lot of the initial meetings and maybe early on maybe 30 to 50 investors but a lot of the initial meetings you can pretty quickly say this might be a fit or this isn't a fit and then be done with it. the ones that seem potentially interesting, that's likely five or six meetings before you're pitching the partnership. And of course, it's different if you have a term sheet in hand and then you call in a couple and they're kind of accelerate. They might accelerate the process so they get in there. But I think the healthiest thing, and we did get this chance with Bane Capital and Scott, is where you have a meeting, it's a get to know you, maybe the next meeting is the deck. And then Scott came to some of our customer trunk shows and he was the only investor who did. So we set up shop um at Harvard undergrad. It was around graduation and we borrowed dresses from our friends. We purchased some dresses and we like we're like let's rent dresses out like let's we want to see this for ourselves. We want to see how much people pay. What designers do they like? What styles do they like? What are they saying about the concept? And even though we were always starting a digital concept, we did this in person because you learn a lot from your customers. And I think we mentioned ad hoc to Scott that were doing this and if you know if he wanted to pop in and and he actually came and he brought an associate from his team who I'm still connected to and know who was our core consumer. So we also acknowledge like he wasn't but he wanted to see that and it let him directly see from the customer's perspective like what was happening what was this concept and I think he alongside us really saw that magic and of course it said a lot to us that he made that effort and showed up. Um, and then like I mentioned, you know, the additional introductions he made to people in his network, that was a big gift to us in terms of our ability to learn, but it was also him behind the scenes kind of checking like, all right, did these girls ask smart questions? Like, what do you actually think of this? Right? So, um, you know, I think once you get down to the investors who are likely a fit or who are really serious, you can easily expect five meetings with with those guys before they're getting you to the final partnership.

Yeah. As you're describing some of the execution, it almost sounds scientific. Like you described the gap between how important the moment is and how expensive something is versus how much money you have. And then you started to describe the questions you would ask of these people that were renting the dresses, you know, was the price point right, was the product right. It almost sounds like you were sort of like underwriting and strengthening the thesis constantly and trying to like ship the product and take action. Like was that what it was like in the moment or was it thoughtful enough to go these are the things we need to prove to ourselves?

You know, it's interesting because so we didn't have a business plan. Like literally all this was happening so quickly that we frontloaded all of our energy and time on anything that was like real customer data or real designer data, right? So we didn't sit back and take 3 months writing all the details of the financial model we had and I think every entrepreneurship like the basic unit economics like does this make sense? What do you need to believe you can rent a dress for? assuming how much it costs to clean it, how much it costs to ship it and and and take a ballpark like don't go crazy about that. Um, but then I think actually getting your product out there to the consumer and the designer is where the really learning starts. And if you create a business plan in advance of that, then I think you risk >> not leaving space and openness to really hear and see the problem and certain insights that might evolve your product to be better. So I, you know, I think I always advise, you know, don't write a business plan. Um, and in fact, when we went to those customer trials, we definitely said, you know, we're curious about customer segmentation. We did purchase a a range of designers and types of dresses and some that were last season and this season. We purchased some with sequins to see if they would fall off in the dry cleaning process. Like a lot of things that we were testing and that we were thoughtful about. But ultimately, the biggest aha that we were able to see was the this woman grabbed the gold sequin sparkly dress. She put it on, twirled around in the mirror and said, "I look hot." And she was transformed. She was just like bounce in her step, extra like strut, the confidence, the whole thing. Um, and that was like Jen and I looked at each other and we're like, "That's our business." Because it wasn't really about the specific specific minutia and details of the product. It was like, how can you make a woman feel amazing? How can you make them feel confident? And that is the main secret of why women need and want all these dresses and they want to spend time and money looking good and putting together the makeup and the accessories and the dress. It's because like they can feel transformed. They feel like they have the power to take on that amazing work meeting or that first date or that, you know, rehearsal dinner of their wedding, whatever it is. And so we needed to create not just, you know, the basic product, but the whole experience that would let our customer feel that way.

Yeah.

And that was what we then kind of had as our guiding light to to work on, start the business. It's like that's the magic moment like how do you manufacture it quickly and and fast and efficiently.

Yeah. And it so it trickled down to everything from like the website appearance which mattered to the designer partners as well to the packaging and we decided to use garment bags which were similar to what like a high-end designer store uses and eventually we would we'd ship in the garment bag on the outside not no box. Initially we had a box also but it was meant to feel luxurious and special. Um, we leaned into like, you know, language and verbiage and things that just felt premium and we were like gifting you what should feel like this magic experience for you to feel like a celebrity of sorts for your special moment.

It sounds just like an insanely high bar for what you believe magical would be for these customers and optimizing for that and and not just going as far as to, you know, think about one thing, but to go as deep as the website and the packaging and every piece of it to create an experience.

Yeah, I really think that's what like great brands do. It's like you know your customer. Ideally, you are your customer. So, Jen and I also had the benefit of like being the customer ourselves along the way. And so, we related like when you saw that spark and that that woman who put on the dress and twirled, we like related to that insight in that moment. So, I'm also very bullish on >> finding and investing in founders who are their own customer. Um, and I think that there's a lot of power in that. But yeah, I think all these details like the 360 of how they echo for the brand. You know, we built out retail stores for an omni channel strategy and we wanted those stores to feel amazing and luxurious. When we think about any event that we're holding, we want it to really reflect the values of our consumer.

Yeah. And now you've been backing amazing companies both at Initialize. You must share these stories with founders in the beginning. and and I at least in my business sometimes I don't think founders are holding a high enough bar for that magical moment for the insights they gather the openness they might have about those insights might be

I'm curious like what maybe their stories or insights that you regularly share with your founders the things you go back to what are some of the things you always are coaching founders on yeah

from this experience

it's um you know it's definitely been really rewarding to invest in a bunch of businesses and also advise and spend time with a lot of founders who are going through these moments I'd say the stories that I tend to share the most are often the ones about like the grit, the resilience, the hard moments because I think it's really easy to get down and to need to be to hear and be reminded that everyone goes through this that this is normal. There's a lot like this. And then I say the other is like how important that customer understanding is like the obsession with the customer. And it's not enough to even have it up front. It's like you got to like in the beginning, you got to keep finding ways to reinject it into the business to keep doing focus groups, keep doing dinners with your customers, hearing and seeing them. And I think luckily we now, you know, we exist in a world with where social media and a lot of these platforms for sales actually just make it a part of your business that the feedback loop is like being hammered. You know, you don't have to work as much to set it into your culture and your system. We had our customer service team was our customer insights team and everyone had to take shifts on that team. Whereas now a lot of sales and and interactions are in social media and like everyone can see it. So I think luckily like it is there but like you do need to care and you need to you know I'm always wanting to find the the founders who are like naturally obsessed with that customer um, you know the passion that the customer feels and the subtleties of I always say like let the customer lead the way. So like what else are they doing in their behavior that can give you insights of how you want to even evolve your product further. Um, there's an amazing founder I'm spending time with later today. the business is Alta Daily and it's like a a digital styling um app and I've seen a ton of businesses try to do this effectively with like you know your personal avatar and like how you integrate shopping and such. Um, and this one I think the founder, um, Jenny, she's so obs she's so obsessed with the customer and understanding her and that comes from like a data perspective, but I think also cuz she is the customer, she understands, and she knows the customer. Um, and it's, you know, you can tell that's like what she eats, sleeps, and and drinks. And she's also like a product person, so it reflects in even the subtleties of like how the customer wants to engage with the actual product itself.

Yeah, it's so interesting. There's so many parallels. It's um across every founder I work with on this, right? Even though it's a physical product, the idea that you're in search of like what is that moment I'm trying to create or um

and it's can be true for B2B also, right? Like I always remind people B2B businesses where you're selling to a business like you still have a customer. Your customers are those businesses. So just in the way we were also talking to Diane vanver and many designers like you can find the person you're selling to that's your customer. or if it's a business, just talk to as many of of them as you can. Be obsessed with what what they think about it and their feedback and the net promoter score from the businesses that you're working with and what what they're saying about it.

Yeah. And so, um, you IPO Rent the Runway and become an investor. Why make the switch? Tell us about the journey into into this part of your career.

So, I had started investing while I was at Rent the Runway. um as part of just being true to our brand and our customer, we had started um the Rent the Runway Foundation to support female entrepreneurs and we had a ton of content and one of the pieces of it was also like a business plan competition that um ended in an accelerator program we hosted and I would always pick a company to invest in and advise that founder as well on a continued basis. um, and then the other thing that happened was a lot of people who had been at Rent their own way left to start their own businesses and I because I think you know founders and talent are so much of a piece of the puzzle once I knew them and you know so deeply and I wanted to support them but also believed in them I would invest in their businesses too. So so that's kind of how it started and I realized that I um had an interest and a passion for it and I loved always thinking of like what's the next Rent the Runway? What's the next step forward? Um, and um I actually then I'd say the transitional step was after Rent the Runway I went to Walmart and I set up a retail tech incubator and I launched a uh personal shopping over text message product and it was called JetBlack and we were learning about conversational commerce and this was back in 2017. So we were thinking for Walmart how do we inject all sorts of like future technology to make a shopping experience better. Um, and I was also connected to, you know, we worked a product for in-home fridge delivery and we worked on virtual merchandising and um, you know, hands-free checkout and a whole lot of other things we were exploring. Um, but this portfolio approach where you're kind of looking at like things on the cutting edge that are kind of 5 years out. Technology of course always had me talking to a lot of interesting additional founders and continuing that investing journey even alongside my time there. Um, and and I loved it. I really enjoyed it. Um, and so naturally, uh, I think as an opportunity came up in the investing world, it was something that I'd always been really curious about. And what I love now is I have investing as a piece of my world, but I also do advising with these companies where I get to dig in a few clicks further. um board work and then sometimes a consulting project where if there's a company that has a particular moment they're living through where I can be very helpful then I'll do the like you know two three days a week where I'll like deep dive and I'll go in hard with them because um I like investing but I also love operating and I think there's a a true kind of heartbeat that exists in me on that front as well.

Yeah, it feels like the operating is pulling you back.

It's I like you know I really enjoy both and sometimes like that's been that's tricky. I think on the one hand it's great because to be an investor who relates to operators and you know who stays close to that feeling and that energy um I think is very powerful and meaningful and also um the tech around us is changing so quickly that I think as an if you just stay only in the investor lane it's actually hard to fully appreciate and and learn and know all of the dynamics that that an in that an operator needs to have around them. Um, and it's one of the reasons I started roller with my kids. It's a scooter suitcase business. There was a lot of new things that I was learning. I'm still learning around creating a product and, you know, sourcing it overseas and dealing with, you know, the engineering of it, the the transportation and logistics of it, the warehousing of those things, selling through Target and Amazon and Walmart, and I hadn't done digital marketing directly myself, and Tik Tok shop is now a thing. Um, but I was like, I want to stay close to this like massive learning curve that I think, you know, the Shopify ecosystem. I didn't live through the Shopify ecosystem as an operator and now so many of the companies I look at are either impacted or on that platform and so I was like I want to build on that platform and so I think this like curiosity is a constant learner is a part of operating and a part of investing. Um, but yeah I think that that intersection and our first investor had been an operator himself and I think the intersection of investing and operating is actually like a really powerful place for a founder to partner with.

Yeah, for sure. It's awesome to see you back and building again. Are you taking the own advice, the advice you gave founders when you were an investor or are you uh are you learning new things? Like how is that experience as the founder the second time through?

Gosh. Um, well this is a bit of a different you know I think Roll Rider um and we have a promo antler 15 for anyone who is traveling with little kids wants a scooter suitcase. So you can check it out rollrider.com. Um, it's been a different project. Like a part of this was really for me to teach my kids about how you start a business. And I think the greatest thing that I've seen cuz you know I go back and teach at HBS and there's a Rent the Runway case and I talk to a lot of early stage founders and I think the biggest thing against that goes against them is like their lack of confidence or like how high the mountain can seem. And so sometimes it's just reminding whether it was, you know, my kids with Roll Rider or kids sitting in the classroom about how we were those two girls at the lunch table starting Rent the Runway without a fashion background or a tech background just like figuring things out. And so just showing people by being that person yourself, the vulnerable person that like this is possible and it's not easy, but like there is a path and a way that it can, you know, it can happen. um like I wanted my kids to see and learn that and it is what I tried to you know remind a lot of founders from also I also you know wanted my kids to learn the tactical pieces about you know how do you start a website and how do you do branding and pick a name and you know digital marketing but even the fact that like you can love work I think for kids and people growing up even postgrad isn't always obvious like there's a lot of people and myself included I was like grinding and out in finance for the first couple of years and I did not like what I was doing and so and I think like homework and work can easily get a bad rap when you're a kid and you're young and it's like wow like what if you can actually enjoy what you do dayto-day like what a gift is that? Um, and so that's kind of what I hope to show them and it's a good reminder I think for entrepreneurs is also like find something that you really love to do cuz if you get to choose it you're the entrepreneur you may as well find a team and a a concept that like you're just you think is really fun.

It's incredible. I loved it. I love having you on the every time we get a chance to talk and have you with the founders or have you on the podcast, I'm always learning something new. I really appreciate you spending the time with us um in this market. Maybe as a final question or thought.

Yeah.

How are you thinking uh or how are you advising founders to navigate what's changing now with, you know, new tools, new technology. It seems like we're entering another crazy cycle potentially.

Um,

and I just love to get your thoughts on it since you've been on both sides um investing and advising. And I just think it'd be really amazing for

our customers.

So I think it is a really interesting time. I mean how quickly AI has accelerated into like permeated every industry um is fascinating to me. I do spend a lot of time on e-commerce and e-commerce enablement. So the place that I've been really digging in right now is just how people will shop I think on LLMs more. Um, so the idea that you will shop and do your research, but also check out on chat, GPT, Perplexity, name your LLM of choice, and then when you kind of ladder back and think about um all of the implications from an infrastructure perspective that that entails, there's a lot of interesting businesses that I think have to be built to support that being possible. I mean, just think of Google as the old search engine. If you think that chat GBT might be the new search engine, SEO optimization and how do you, you know, get to be one of the brands that an LLM recommends, how do you have the right conversational attributes so that people can ask questions about your product? There's, you know, there's that. There's a whole checkout flow and how can that be seamless? That has to happen in a secure way. Um, and then there's a lot of personalization opportunities too, right? where if you're shopping in these platforms across categories, but maybe you're also planning your trip to Japan, then in theory, this chat GPT can also like start recommending or knowing because you're going to Japan in a certain exact month and they maybe even major itinerary like other recommendations and start, you know, proposing other things that you might want to buy or do. So, I just think we're entering really the next frontier of how people will shop digitally. It relates to some of the work I did at Walmart, even back back then. Um, but now the tech is just like so advanced so quickly that I'm excited to see what's to come.

I love it. It feels like so much of this is inevitable. Like we will see it and it will come to fruition. But from the stories that I've heard from others and from you today on the show, it seems to me like it all comes back to the people.

People that are willing to work hard, be resilient, challenge themselves, challenge their customers to think differently. It's so cool you're starting Roll Rider with your kids and I mean there's no shortage of chaos in the world. I'm just curious to hear about like life as a mom, life as a co-founder with your kids like what are you thinking about right now?

Yeah. So my initial like answer when people would ask me this and I I had young kids um was you know I think being a mom, being a parent makes you a better entrepreneur or a better executive. You have no time to sweat the small stuff. I think you've really got to um prioritize in a deeper way. I found great ability to blend my kids into my work life and like show them which I think was really inspirational to them and bringing them into the office, making them a real part of what I was doing. Um, it has gotten a whole lot harder as they've gotten older and I think the time of co also created maybe more direct dependency where the kids like need or want their parents like it feels like there was like some shift there. Um, but whether it's like homework that only you can kind of help with or you know a social moment or something going on in school that you want to be there and with them for. And I think one thing I'm really grateful for is um in the world of entrepreneurship there there is some flexibility that you're enabled to incorporate into your life. Um, and then I think there's also just like so much better technology that sometimes I feel can actually support whether it's, you know, AI helping me plan my kids' birthday party and organize documents or whether it's Google Docs which lets me even if I'm traveling on a work trip actually like jump in and and work on something with my kids. But um, I think kids learn a lot from seeing and other people doing. And so I guess my my greatest hope is that amidst all of the chaos and the multitasking that just feels frenetic, you know, the the perseverance and just like, okay, things seem overwhelming, but like it's possible. We can find a way to make it work. Um, everything is figure outable.

I love it. That's awesome. I hope more parents are investing in their kids the way you are. It's just amazing to see that, you know, you can do anything you want, right? You can like pick a project up and you can take it as far as as your creativity and your inspiration and your ambitions will allow you. And like to see you doing that with your kids is is inspiring.

Good, good stuff. Well, this was so so fun doing this. Thank you for having me on.

Yeah, thank you for being here again. Um, we love it and the founders are always grateful. So, thank you for being here, Jenny. Thank you for watching. This has been Further Faster, the Antler podcast that talks about taking ideas from inception to scale. Thank you, Jenny, for being on the show today. And if you've liked and enjoyed the show, please remember to like, subscribe, and share this so that we can continue to bring more great founders and investors on.