Name: Brainstorm Tech 2024: How to Innovate Without Losing Your Mind
Uploaded: 2024-07-17
Duration: 14 min 2 s
Description: Jennifer Fleiss, Partner, Initialized Capital; Co-founder, Rent the Runway, Jetblack Interviewer: Andy Dunn, Chief Executive Officer, Pie; Co-founder, Bonobos; Co-chair, Fortune Brainstorm Tech

Jennifer Fleiss, Partner, Initialized Capital; Co-founder, Rent the Runway, Jetblack Interviewer: Andy Dunn, Chief Executive Officer, Pie; Co-founder, Bonobos; Co-chair, Fortune Brainstorm Tech

Brainstorm Tech 2024: How to Innovate Without Losing Your Mind

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Thanks for having us. So Jenny and I were comparing notes we met in Soho in 2009 and you were starting rent the runway and I wanted to begin with what it's like when you come down from the entrepreneurial journey. So you spent nine years building rent the runway at some point that went public. Then three years during the go go days of e commerce Transformation at Wal Mart. What was it like? After all that excitement came too close. A really big comedown. So nine years then jumped straight into the next role, starting and leading and growing up to zero to about 300 employees within the business. I ran at Wal Mart all of a sudden came out of that and it was COVID and I had left Wal Mart and I was like, who am I as a person? What do I want to do with my life? And in that process of that span of entrepreneurship, which was a complete blur. I had, had three Children. I had lost my mom and there was a lot I think I just hadn't processed because it was 1 ft in front of the next problem solving, taking care of the hundreds of employees that we had at various companies. And so this kind of question of like, what did I actually want in life? Where was I in life? Like, really suddenly hit me really hard along with time to kind of process that, which is in theory important, but it can also be a little bit rattling. Yeah. So one thing I like about you is that over the years as we've gone through some ups and downs as friends and fellow entrepreneurs, we've talked about where do you get help from a mental health perspective? We've compared notes on executive coaches and I think at some point shared one of those compared notes on therapists. How do you decide as a founder when you're dealing with difficult things? And maybe even as a human folks in the room who have this decision to face, when do you hire a coach? And when do you hire a mental health professional therapist, psychiatrist, et cetera? Yeah. Well, before I had a coach or a therapist, I had people like you, Andy, honestly and my co founder, but truly in New York, I mean, the ecosystem is a lot bigger now. But when we were starting around the runway in Bonobos, there was like eight of us and we all were helping each other. Whether it was like, how much are you paying for per square foot for office space? Like the silliest question all the way to really hard stuff around fundraising or first person, you were going to fire and the ability to, like, authentically form friendships and meet people and get advice from them both. Kind of the most practical way. Like, we didn't have any time, it was like a very practical way to get things done and figure it out. But also it was like, it was really meaningful and it led you feel like you're not in this alone and having a co founder does that as well. And so I feel like, very grateful that in these like dramatic highs and lows of entrepreneurship, I had someone not just to deal with the low moments because those definitely happened in entrepreneurship, but it's way more fun to deal with the high moments. And like at the end of the day, that's what kind of gets you to muffling through the next, the next blow. And that idea that you're not in this alone because your co founder implicitly like cares just as much as you do, like your necks are both on the line. You've both got to make it work. That was something in the second business that I started for Walmart. Like I didn't have that in the same way. And I never, I never actually took it for granted because like, it literally came up so often. And I think that's what kept me really afloat in a very sane way amidst losing my mom and having three kids while being at rent the runway. Yeah. And we joined Wal Mart at roughly the same time, I can remember sitting down with Doug mcmillan when we were doing the Bonobos deal with Wal Mart and Doug just looked at me with those like piercing blue eyes and he was like, Andy, why do you want to do this? And I was, I was nervous at that dinner. There was a $300 million deal on the line and I just thought about it and I said, Doug, I need a job and he was like, you have a job and I was like being a founder of a company is not a job. Always worrying about payroll and all these things. I'm curious was your experience of managing your own mental health different when you were a founder versus when you were a doing great things but effectively a corporate executive. Interesting, you know, I think, um I think the biggest difference was probably like, there was more resources that you could put to work within the ecosystem of Wal Mart. One being coaches, for example. So around the runway, there was easily seven years before we had coaches or we talked about having a coach for Jen and I within the company, I don't think it was as common back then. You know, we launched the business in 2009, but we also didn't necessarily have the capital, the resources or really the time to be thoughtful about that. I mean, I wish we were more proactive about it. What we did do very well, Jen and I was, we forced ourselves to sit down every other week together. The two of us, whether we thought we had something to talk about or not and it was meant to be about, like, our relationship and, like, talking about like us and like, there was some hard stuff that came up, there was like some funny stuff that came up, but like definitely some like hard tense conversations that came up and that advice had been given to us by of our board members who's still an observer to our board. But I think just having, you know, for those seven years having great board members, great advisor, great peers around the table took that role within the Walmart ecosystem. Like they have a great set of existing coaches that they can pair you with and I was able to see like huge benefits in then leveraging that resource and also having this feeling, you know, within that broader corporate, I wasn't also fundraising, you know, there was a sense of like there was some safety net connected and this broader, you know, it wasn't entirely 100% on my shoulders. So I think that let me breathe a little bit more, but it was also like a different sort of responsibility to live through totally. And I do want to take questions in a moment. So please prepare your question. Um Let's talk about co founders for a second. And I have to tell you something. You don't know when we sat down for lunch in 2009, I was in the middle of a co founder, divorce with my business partner. And I remembered thinking these two have no idea how hard it is to have two amazing leaders. Both who with business school pedigrees right out of H BS. The two of you were, this isn't going to work, which was the most weird thought to have had. And then you have endured with your co founder and the CEO of Run Runway Jen Hyman. You were there for nine years. You had a thoughtful transition. You're still on the board. What is unique about your friendship and partnership with her that has enabled you to do as friends and co founders, something that we so rarely see which is to endure as both. Yeah. Well, thank you. You truly have seen the whole trajectory. It is probably in the course of around the runway. What I feel the most proud of like legitimately is my relationship with Jen and the fact that it's still a very strong relationship. Today, we talk almost daily about pretty much everything and I'm still on the board with her. So some of it is business related and some of it is like friends and life related. But the reality is we started our friendship and our relationship during this time where we went through so many moments together of blitz scaling and highs and lows and fundraising and go public and COVID at a time where people didn't need to get dressed and we could never imagine that would have happened. Right. And then the moment when I did decide to leave and the moment when we brought in a couple of senior executives for the first time, like there were just so many like hard and special moments that like kind of like a spouse, like no one lived through that with you in the same way. But then I think knowing also as a person that she and I could both kind of weather storms as people and keep that relationship with each other. And I say with like our founding team in this really like special place, like that's a, that is like the stuff that's meaningful uh in life. And, and ultimately, I don't know, like it, it really is what I'm most proud of when I think of my time there, great anyone ready to jump in over here? Um Can you talk about the specific moment when you had the self awareness to know you had to step away in order to keep the company growing? Yeah. So I've always loved the earliest stages of entrepreneurship and at rent the runway like Jen and I were able to have really real conversations. And so at one point I took on a role in like starting the new parts of our business actually. And so I started our omni channel retail strategy. I started our subscription business, which is say about 90% of more than 90% of our company. I started a whole sponsorship business. So we were like finding these ways to like use my best self that would also make me the happiest within the business. And at some point, like, there wasn't more stuff we should start, it was just about baking all of that. So that was like a very clear thing. And we'd also hired an amazing senior team that felt really like good that, you know, I felt like I could leave if I wanted to. And coincidentally, I feel like, right as everything was feeling very settled and good in that way, Mark Laurie, who we both worked with at Walmart, reached out with the opportunity to go start a business on my own within Wal Mart ecosystem. And he's like, you know, pick your team, like, you know, it's your company, your vision. And I had for really all of my career, done things with Jen and she'd always been the CEO which like I was always psyched about and that was great. But like, it was a chance for me to be like, who am I as an individual leader and business person and to like, try that on and have that experience in a really unique moment in time. I mean, this like entrepreneurship at a moment where Mart had just sunk $3.3 billion of like through the elephant in the swimming pool. Like we actually care about digital and we were led to take some really big swings. It was, it was a really unique opportunity. And I think she also saw that and wanted that for me as well. And the whole board, the whole senior team, I think we were able and we still have like very healthy relationships and conversations because I would never have left if it wasn't that I knew like the business was in a really good ok place. So back to rent the runway, the company went public at one point. I remember it was valued at 800 million in the private markets and worth more than a billion. I looked this up last night, 66 million of market cap today. Tell us two things about that. What's that been like for you as co founder? And what has that meant for showing up for gen and maybe some specifics on how you've had to show up because it does become asymmetric at some point being the person that's still in it and running it versus being the board member looking in on it. Yeah. No, absolutely. I mean, as much as there's highs and lows at a company, as much as there's for your co founder it is quite different when, you know, I've diversified from my own career and from my role in investing now and the portfolio of founders that I work with versus being there day in and day out that said, you know, like the actual valuation of the company, I think in some ways that's never, has never felt like something where like, wow, that's money in the bank. I mean, like my shares have been like, as far as I know, it's kind of like, always been this thing where there's, there's money that hopefully at some point will exist, but it was never, it was never as like tangible. So like, I like the pieces that I cared the most about and that I really saw Jen care the most about were like when our employees who were brought in with like option valuations at a certain amount. Ben saw those being underwater in a way that when you're a private company is never visible and it was not, it was not at all connected to the actual performance of our company or what they were doing, it was connected just like what's out there publicly day to day and you have to kind of manage through that emotional and kind of cultural tension and pain for your employees. Like that stuff was really hard and friend of mine um seeing Jen carry the weight of what like I think for her too, it was more the weight of what that was to be a leader to employees then than it was like what her personal portion was was worth and to like, try to be the partner for her to support her in the moment where that was happening and then you have to compound it with like laying off employees at different points in time. Yeah, it was definitely really tricky. You know, I think all this stuff though. It is. What in this next chapter now where I landed about that? Tell us about now you're on the other side of the table, you're a venture capitalist. What's different about being a founder now from back then? And how do you show up for the founders that you partner with? Yeah. So it, it still feels, I don't know, I still feel like I'm both an operator and an investor. So I started doing investing while I was at rent the runway even and then at Walmart. And I think one thing that's awesome about initialized is like all the partners are former operators and founders. And so I actually feel like I'm at home in this entrepreneurial ecosystem and in the way that we work with founders. So that was like for me, my answer of how do I find my happy place in making this dramatic transition between being a builder, being an operator, growing teams to being the one on the sidelines and guiding. But what I will say, you know, I think all the learnings and the highs and lows like have become these amazing learnings that I can now share. They weren't just like for nothing and it wasn't just like these pains and scars and bruises. They were ways that I could like now guide and share it with founders. And, you know, my favorite one, I actually shared this tip with a founder earlier today. It's not just about sharing the scar stories. It's also like create an email account that's like memories at Rent the runway.com or whatever it is. And when you have like a fun moment, a funny email, a photo just like BC that email and then like look back at it every five years and like celebrate and figure out like fine, like remember those special fun moments because it all goes by really frigging fast, right? I've got one more for you. Yeah, let's go back to the beginning. Let's say you had a founder who was exited and was at a similar low point. What would you say? What would be the one thing you would say to someone who was in the, in those shoes that you were in just some years ago? Yeah. Well, first off, I hope that I would be the type of investor that they would come to because one reason why I went to investing is our first investor, Scott friend from being capital. He had been an operator and the ability for him to empathize and to be that person that we called at like 830 in the morning or 10 pm at night in those moments, like is literally still there. Like I still have to find an investor with empathy with the empathy that's on through it, that you can trust that like you want to call and you feel is going to be there for you and have real thoughtful advice. And I think what he what other people told me, it's like this journey and life is like a lot longer than you think of it as when you're an entrepreneur, you're entrepreneur, it all runs by and I'm getting to this. You're going to let me just say I so admire your journey and thanks for being here to talk about this. Thanks everyone.