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Jenny Fleiss and Larry Cheng Discuss Rent the Runway, Jetblack, and Why She Joined Volition Capital


Jenny Fleiss sits down with Larry Cheng to discuss her entrepreneurial background, the lessons she’s learned from Rent The Runway and Jetblack, and why she’s excited about joining the Volition team as a Venture Partner. 

Video Transcript

Larry Cheng: Hi, I’m Larry Cheng, I’m a co-founder and managing partner of Volition Capital, and I am very excited today to have a chance to chat with our newest team member, Jenny Fleiss, who’s joining us as a Venture Partner.

Jenny Fleiss: Hi. Thank you so much. I’m so glad to be here.

Larry Cheng: I thought we could do is have a little time together for those who don’t know you to get to know a little bit better. So, tell us who you are, and like the short version of your experience of life, give us the whole spiel!

Jenny Fleiss: I’m Jenny Fleiss. I co-founded Rent The Runway out of Harvard Business School. And then I went to start a business for Walmart and helped launch their tech incubator. I’ve been doing my own investing as well. So, along the last few years, investing in a bunch of startups.

Larry Cheng: Now, did you go to business school at Harvard Business School knowing you wanted to start a business?

Jenny Fleiss: No, I did not.

Larry Cheng: What did you think you wanted to do?

Jenny Fleiss: I wasn’t quite sure. So, I had worked in finance. I went to Yale for undergrad. I worked in finance, and it wasn’t quite hitting the mark. I worked at some of the larger investment banks. And, so, I went to Harvard Business School with the goal of finding just something I love. And it drove me every single day. And that’s where I discovered that being an entrepreneur could be a career. I hadn’t actually even realized that before. And, it just so happened that during my second year, my co-founder of Rent The Runway and I started having a lunch conversation and it amounted to what would become rent the runway.

Larry Cheng: If you want the full story on Rent the Runway, there is a “How I Built This,” podcast that you and Jenn Hyman are involved with. I would recommend that. Having scaled a very significant Internet business, both independently and within Walmart….as you think about your Rent The Runway experience in particular, and what you learned there and what experiences you had that you might bring to sort of thinking about investments, what would that be? What are the lessons learned?

Jenny Fleiss: Yeah, well, listen, part of why I’m excited to be going into growth equity and working with Volition is because the VCs we worked with at Rent The Runway were such a key part of our journey. And, it inspired why I wanted to go into this industry myself and hopefully share that operating lessons that I’ve had myself with other founders.

Larry Cheng: So, you were operating there for many years as a company scale, which is exciting. And then you made the move to an entrepreneurial venture within Walmart. And tell us what that experience was like and what you learned that might be different from Rent The Runway itself.

Jenny Fleiss: Many things were different know some things were the same was and Walmart empowered me in a big way to join their team as an entrepreneur. And why they brought me in was because of my entrepreneurial skills that Mark Lurie hired me and wanted to bring in entrepreneurs who would run at that same pace and with that same passion that an entrepreneur does. So, the business that I started for them was called Jetblack.

It was personal shopping over text message, and there was a whole host of things that we wanted to learn for Walmart, the largest of which centered around conversational commerce. The idea of buying something with your voice or with the text message and having an actual dialogue with a bot and/or a person. And, so, we had a lot of learnings in the tech stack we were building there, but also in merchandising insights and ways that consumers wanted to shop, that Walmart could continue to evolve as they got more digital.

Larry Cheng: That’s great. For those of you who’ve been following our blog and so forth, you know that we’re spending a lot of time on e-commerce. We have spent a lot of time in e-commerce and we’ll continue to do so, have done a lot with you to see. Brands have done a lot with their digital media and other aspects of Internet and consumer businesses, along with our core software efforts. And, so, we think Jenny will bring a ton of expertise, especially to our Internet and consumer efforts. We’re excited about that. You’re now making the transition somewhat to growth equity investing. Now, you’ve been a very active seed investor along the way. We should point out that you’re based in New York City. And, so, you’ve told us about your background, now to your investing efforts… so, how is it that got you interested in investing – and why did you decide to come here now?

Jenny Fleiss: Yeah, absolutely. Well, first off, just starting Rent The Runway and the relationship we had with our investors showed me how that impact at an early stage is really key. As a first-time entrepreneur and founder, as Jen and I were, and partnering that with the skillset and resources of a fund who really wants to be that partner, like a true kind of co-founder partner had made all the difference for us. And, so, as I started to see employees from rent the runway, starting their own businesses and then employees from Jetblack starting their own businesses, there was this natural dialogue around how should I find product-market fit and just getting their businesses ready to raise funds. I was happy to help, and I really loved those conversations and that work, so I invested in some of those employees, initially, other friends from the startup ecosystem that was evolving in New York.

I’m really glad of what a strong entrepreneurial community there is in New York and was excited to kind of be a part of forming that and helping that continue to thrive and wanted to kind of pay forward some of the amazing advice and mentorship that Jen and I had gotten, which I think was so instrumental to starting Rent The Runway. I just kept listening in to these amazing founders who I knew really well, who were starting businesses. And as their businesses grew, often it led to a Series A investment and then a Series B investment. I was able to flex my muscles into that landscape and realize that that’s where I want to learn from you and to build more skills. But also, that I think it’s a really sweet spot, an opportunity from a returns perspective in investing.

Larry Cheng: So, as you look out for the next many years as an investor, as a growth equity investor, what started here now? What are you interested in? What what’s your lens? What types of businesses either sector-wise or certain parameters or characteristics you’re looking for that really kind of hit your sweet spot?

Jenny Fleiss: Yeah, absolutely. Well, listen, I always like to see an ambitious founder who has great talent in both pitching and selling to investors, but also to pulling together great teams. I think the teams that you pull together are a really big, important part of the journey. A couple of categories and themes that I’m interested in: I have this belief in the “executive athlete,” where we all treat ourselves like we’re performance athletes, optimizing our every daily move. And that can mean fitness trackers via your Apple Watch or sleep trackers like the Oura Ring I have on. I think there will be more home health tests because they’re so easy and affordable at home, we can just take them more regularly. And COVID has accelerated this trend, even more, just showing up-front and center how critical our health is and how we really need to prioritize health. So, in-home health, health maintenance, and monitoring is one theme.

I’ve always just been excited about the experience economy. The idea that if you are spending time on something, that it should be an experience for you…it should be something that’s enjoyable and exciting. I think coming out of COVID, consumers are going to be craving those experiences and looking for new ways to spend their time that are Instagram-worthy, that they’re going to want to actually make the time to connect with people in a new format. I have an eye out for that.

And then, omnichannel generally. I mean, one thing that working at Walmart gave me, an even deeper appreciation for is just the real power, not just of digital, but of how physical and digital can work together to amplify a brand, to leverage supply chains in a more creative and effective way for last-mile logistics. So those are a few of the trends that I’ll be watching.

We can’t ignore sustainability. I mean, there’s so many things I’m excited to dig into with you!

Larry Cheng: Well, we’re so excited to have you here. We’re going to spend a lot of time with you and let all the folks out there get to know you better in the evolution context. And we’re thrilled to have you join us. So welcome and thank you.

Jenny Fleiss: Thank you so much. Glad to be here.

Jim Ferry

Jim Ferry


Jim Ferry



Larry Cheng

Managing Partner

Larry Cheng

Managing Partner

“Success is 1% inspiration, 98% perspiration, and 2% attention to detail.”  – Phil Dunphy