July 2, 2025

Thirty Minute Mentors Podcast Transcript: Rent the Runway Co-Founder and CEO Jennifer Hyman

Transcript of the Thirty Minute Mentors podcast interview with Governor Chet Culver
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Adam Mendler

I recently interviewed Rent the Runway Co-Founder and CEO Jennifer Hyman on my podcast, Thirty Minute Mentors. Here is a transcript of our interview:

Adam: Our guest today disrupted an industry and changed the way countless women shop for clothing. Jenn Hyman is the co-founder and CEO of Rent the Runway. Jenn, thank you for joining us.

Jennifer: Thanks for having me.

Adam: You grew up in New Rochelle, not too far from Rent the Runway headquarters in Brooklyn. Can you take listeners back to your early days? What early experiences and lessons shaped your worldview and shaped the trajectory of your success?

Jennifer: I think that first, you’ve got to have a lot of love around you because what really has shaped my ability to be on this journey is knowing that no matter what, I have a support system. No matter what, I have an amazing life, a great family, great friendships, and a lot of love in my life. So entrepreneurship is fundamentally about failure and iteration and resilience and picking yourself up and taking the next best move. And in order to have that ability to take the next best move, you have to have a deep-seated sense of confidence. And for me, that confidence has always come actually from love, from being loved by family and friends and by giving love to others. I think it’s really hard to be on the entrepreneurship journey if the components of your life, the family and friendship components of your life, are not in place. And we don’t often talk about that, but the more you have a great family who is supporting you, a partner who loves you, the more you have a great set of friends who don’t care at all about your job and what you’re doing, I actually think it sets you up for more success.

Adam: I think that’s great advice, and a lot of us are fortunate in that we have families who love us, who provide us with tremendous emotional support. They’re there for us, great friend groups, but a lot of that requires effort, work, going out, building it, cultivating it. What advice do you have for anyone listening to this conversation on how to create and develop a great support system?

Jennifer: One of my fundamental philosophies is like everything is better when experienced together. Everything is better as part of a group, as part of a team. I’m not an alone time person. I’m a mega extrovert where I get all of my energy from being around other people and having the vibes be just filled with joy, filled with energy, even filled with chaos, I’m cool with. I much prefer chaos over quiet. And I think that you can’t build anything of substance in life, whether it’s a great company or whether it’s a family solo. You need to learn how to be part of a team. And what that means, and this was something that was instilled in me from a very early age with my family, what that means is having the self-awareness to understand that your role is going to shift on a dime. Okay, so I’m the oldest daughter in my family of four kids. And that has a set of assumptions of what that implies and what role I’m going to take on in my family as a leader. That being said, you have to be ready for that role to adapt. So I was part of a family where I had a younger sibling who’s severely autistic, who cannot live independently, who has created an environment where life is a surprise. You don’t know what you’re going to get with the day with Sherry. There could be hilarious laughter. There could be outbursts and crazy episodes. There could be a lot of different scenarios that happen based on her behavior. And there’s so much to be learned from living your life with someone with a disability. But the reality is that my sister, though she’s now approaching 40 years old, is still in many ways like a four or five-year-old. So she still has to be taken care of in every single physical, emotional sense. And that is an exhausting endeavor, especially for my parents. And so, as a kid, you’re kind of intuitively picking up that, yes, your parents are meant to be the ones who are always in control, who always have everything covered, who always are the ones who are providing the care. But there were times when myself and my siblings had to step up and play a more parental role for a period of time, where we had to assist in that way and bless our roles on the team. And you’re recognizing not just this idea of what everyone around you is contributing to the team, but you’re recognizing that you have to be nimble and understand that things are agile and they’re moving and changing quickly. It’s that lesson of comfort with continuous morphing of how you’re going to contribute to the team that I think has prepared me for building a startup. Where, yes, on paper, my role and my title have been the same for 16 years. But every time I hire new teams of people around me, I’m adapting in terms of what I should be contributing to RTR? How do I leverage the strengths of the people around me so that they can shine? And let me fill in some of the ways that I can uniquely do based on their capabilities. So that’s this idea of a team always being at the center of everything, and just an appreciation of the fact that teams do not stay in their position indefinitely. So it’s not like sports where the power forward is always the power forward and the center is always the center. You’ve got to be able to flip your role on a dime on the field and know how to respond to the situation based on the other players there. And that is what I learned as a kid. And I think that that’s been the very best lesson for my marriage, for my career. And it’s ensured that I’m always thinking of how I can contribute, and also focusing on the fact that change is good and change is expected.

Adam: Jenn, I really, really love that. And there’s so much to dive into. And I have no choice because you brought up a sports analogy to start there. When you said the power forward isn’t always the power forward, the center isn’t always the center. That was true up until recently, when basketball has become a positionless game and has become exactly what you just described. The best basketball players are essentially positionless basketball players. You look at LeBron James, who can play 1-5. You look at the entire Oklahoma City roster, where you have player after player after player who you can put at guard, put at big man.

Jennifer: This shows how clear my knowledge of basketball was in the late 90s, after the whole John Starks, Patrick Ewing, Anthony Mason, Knicks era, that’s when it kind of ended for me. So I’ve really been really inspired by the Knicks and actually the Liberty of the current era. So I’m getting back into it now.

Adam: Well, going back to your heyday as a basketball fan there was really only one player who was a positionless player and that was Magic Johnson and that’s why he was Magic Johnson because he was able to do exactly what you described and what you’re describing is what every entrepreneur needs to be able to do and What is really at the heart of adaptive leadership? Being able to wear whatever hat you need to wear on a given day, being flexible, and being agile. That’s what it’s all about.

Jennifer: I think that we specialize too quickly. We specialize too quickly at work. We specialize too quickly. I see it now with my kids, where my oldest daughter is in second grade, and if she wants to play a sport, they’re already requiring her to come four days a week. And that means that there are less days to pursue other interests and to understand what her other interests are. She’s eight. We have no idea what her interests are going to be. I think that we’re so pre-professional in every single aspect of our lives that we’ve taught ourselves that specialization is the way to succeed. I don’t think it’s the way to succeed, and I certainly don’t think it’s the way to be happy. And so the more that we stop doing that, stop just saying, well, I’m only a marketer or I’m only a chief financial officer. Like, no, my CFO is actually one of the most strategic people in the company. He’s often giving product ideas. He has ideas about the fashion that we’re buying, and that’s Pete. I don’t want people to stay in their lane. When people are staying in their lane, I’m not gonna get their full brain power out of them. And it’s not fun. No one wants to just stay in a specialization. That’s where you wilt away and die.

Adam: That’s such great advice. The importance of not pigeonholing yourself. I just did an interview with a CEO specifically on cross-functional teams and what it takes to lead a cross-functional team, and what it takes to succeed on a cross-functional team. And so much of it comes down to as a leader, encouraging every person on your team, regardless of what their background is, regardless of what their title is, not to think of themselves as limited within what their specialization is, not to limit their focus, but to open up their mindset and to be willing to contribute beyond whatever their specialization might be.

Jennifer: Couldn’t agree more. That is how Rent the Runway functioned for the first 11-plus years of our business. And then we had a period of time where we got bigger, and we thought we needed to be much more structured and much more process-driven in how we operated, and much more about functional leadership as opposed to cross-functional goals. And let me just describe where we are right now, and that’ll elucidate this change. I made a change at the company 18 months ago, where I thought we had to go back to our roots. And we were going back to our roots in two important ways. One was customer obsession, but the second was ways of working and how do we inspire the team again, make the team more agile and increase productivity, and create more of this sense of ownership where everyone is a founder of this company. And how we succeeded in the early days of Renzo Runway was we have these cross-functional pods. We would have really simple goals. We would have GMs of these cross-functional pods. A pod would mean that every sort of specialty that you needed to get the goal done was on the team. So that team comprises engineering, merchandising, finance, analytics, marketing, and product plus, plus, plus. And those pods are what turned us into an innovative company that was able to move from just renting special occasion wear to disrupting an industry with this cloth and then the clap out of this entirely new way of getting dressed. It was because of the pods. We went back to that structure 18 months ago, even though we’re a much bigger business than we were at the time. And it has been the very best change to our culture that we’ve ever made. The more you get big, the more you actually have to edit what you work on, and the more you have to make sure that everything is even more cross-functional than it was before. Like, it didn’t work to have OKRs just layer up into individual functions. It meant that everyone was doing their goals in isolation, and it wasn’t connected as much to a customer goal. Now we have a customer-oriented goal. We have a squad of people that are focused on delivery against that goal. They have all the resources they need. They’re owning it. They’re autonomous. They’re creating their own roadmaps. They’re launching their own releases every week, every two weeks. They’re looking at the results, figuring out where to allocate their internal resources, because that’s what a company is. It’s just about the allocation of capital. Whether that capital is human capital, whether it’s time, or whether it’s money, and you need to allocate your capital appropriately to the things that have the highest chance of success. And doing that in a cross-functional way is a much smarter way to get to the outcome of growth than creating functional OPRs. It has truly revolutionized my company, where we were able to bring the business to break even, now set it back on a growth path, and do some really huge things on behalf of our customers that I think set us up for really the next chapter of success for RTR.

Adam: And Jenn, as you describe your efforts to lead the turnaround of Rent the Runway, you’re alluding to ups and downs that you’ve experienced over the course of the company’s history. And you’ve experienced significant highs, significant lows. It’s part of the entrepreneur journey, but as a company that has experienced your level of success, those highs have been higher than most, and those lows have been lower than many. And I want to start with the highs. How did you get to the level of success that you were ultimately able to enjoy? What were the keys to going from this great disruptive idea to a billion-dollar business?

Jennifer: I think that number one was the idea had product market fit from the very beginning. Product market fit is about Do customers in a consumer-oriented business. It’s really about do customers really need this? Do customers really want this? I think that sometimes people who are entrepreneurial and they want to start a company can tell themselves a false narrative on whether there’s a true product market fit or what they’re putting out into the universe. So we knew how renting clothes would financially make sense for customers, how it made sense for them in terms of the variety they wanted in their wardrobe, how it actually helped women show up feeling like their best selves every single day and the confidence boost that they got from continuously being able to change their clothes and change how they felt about themselves. We knew that there was product market fit and how we were opening up an entirely new marketing channel on behalf of all the brands that we work with. How do you build brand affinity? You give someone an experience wearing that brand where they understand the quality, they understand how it fits, they wear it in their real life, and then they become a fan of that brand forever. So the first rule is to make sure that your idea actually has legs with the consumer, like that there’s something here to really build. Number two, you have to ensure that there is customer obsession along the entire journey. And this is where we’ve done a very good job, but there are times that I wish I could go back and change some of our priorities. Every single thing that you build along the journey has to make the customer’s experience better, has to deliver more value to the customer. And that has to be real. I think that often you can develop great salesmanship within your own company, where you justify work streams that actually have no bearing on us. But you can’t build anything of real sustainability without continuous innovation on behalf of the customer. And that innovation has to come from a deep understanding of the customer, a deep vision of where the world is coming to. and channels that you build within your organization to get continuous feedback from the customer on what she likes and what she doesn’t like about your experience and how you can continuously iterate. And when your customer is obsessed, it naturally implies that you are going to be flexible in how you deliver the best customer experience. So I’ve always had a very strong vision of where I wanted to go. I had an understanding of what the real product market fit was. I had a vision for this Plaza in the Cloud 15 years ago, when people thought that the idea was insane because Rent the Runway came into the market before secondhand clothing was really part of the closet. We were pre-RealReal, pre-Poshmark, pre-ThredUp, pre-everything. We were the first of these businesses to launch and normalize, and make aspirational the idea of wearing clothes that other people had worn before. But I knew that a closet on rotation was going to be a significant part of the industry in the future. So I was pretty hard-lined about the long-term vision, but I was very flexible and have always been very flexible on the path to get there. And that path has to be continuously iterated in partnership with your customers. And you need to create channels where you’re really understanding how you can continue to serve her as her life changes, as the world changes around her. And I think that the success has come from that honoring of the customer, honoring of the long-term vision and beliefs in that long-term vision, but deep iteration and flexibility on the ways to get there. Which means that my expectation is that most of what we launch will probably not be successful out of the gate and will require a lot of different changes and iterations over time. Or a lot of what we launched is just the wrong idea. You have to be so comfortable with constant, constant experimentation and therefore failure to get to the right answer. And I think that for some people at every level of an organization, a fatal flaw is stubbornness or dogmatic adherence to what their belief set is. Yeah, it could be dogmatic about the vision, but don’t be dogmatic about anything else along the way. And that means you can’t be dogmatic about talent. You can’t be dogmatic about what should be on your roadmap. You literally have to continue to experiment.

Adam: Jenn, you shared so much there that is so incredibly valuable to anyone interested in starting a business, growing a business, scaling a business, or even working in a business that they’re trying to help take to the next level. When you started Rent the Runway, I’m sure plenty of people told you that it was a bad idea. Now, everyone tells you it’s a great idea, but you have confidence in your idea, unshakable confidence in your idea, which is essential. But that’s where it stops.

Jennifer: Let’s talk about that. Not just about confidence, okay? Because there’s a lot of people that have confidence and they have shitty ideas. And you shouldn’t have confidence in those ideas. Why did I have confidence? Yes, I’m a confident person. And just like I said at the beginning, I knew that if this didn’t work out, I’d be fine. And I had a support system and I was smart; I could get another job. But I had confidence in the vision because I have been a true student of women’s self-image, because fashion is fundamentally, for me, not about fashion. This business is not about fashion. This business is about how women feel about themselves and how fashion is a conduit to enabling them to feel the way that they want to feel about themselves. So, I understood how things like social media were affecting the fashion industry and would completely change the fashion industry forever. I understood the behaviors that gave me confidence that rental was going to work. Because Rent the Runway, in my opinion, already existed before Rent the Runway. It existed by nature of how women consumed fast fashion. When women in 2008 were going into an H&M store or a Zara store, and they were buying tons and tons of new things to wear out to work and dates and various things, and they would wear those things once or twice, and then they would throw them away. They were renting the runway from those stores. Those stores weren’t offering them the ability to rent, but they were essentially utilizing cheap prices and high variety as a way to actually put their closet on rotation. I saw that that shift in behavior happened before we introduced the runway. I knew that at department stores, the reason why the dress business with such a negative margin business for them is because women would wear dresses, they would buy them, wear dresses to special events, keep the tags on and then return them. They were renting the runway from those stores and creating negative margin businesses for that category. So when you have an idea and you’re an entrepreneur, really assess what gives you the true confidence, what data do you have about the way the world is changing, about how people already are behaving that could tip the scales in your favor? So, another point of confidence that I had was 2008 was pre-Instagram, but it was post-Facebook. And Facebook had introduced by that time the idea of posting photos on a newsfeed. And people were starting to post photos on their Facebook newsfeed all the time. And I saw that that put increasing pressure on women to have variety in their wardrobes because they couldn’t post themselves in the same look day in and day out. They needed different looks. And that was fueling fast fashion. And that was yet another reason why people might consider a service like Red Throat Eye. So I would just encourage people, when they have an idea, to really question themselves as to what really does give them the confidence. Because if there aren’t other real pieces of data that validate that your idea has legs, you could just be running against the wrong problem set.

Adam: That’s great advice. The importance of challenging yourself every step of the way. Being flexible, being adaptive, a fatal flaw as an entrepreneur is stubbornness. And that can be a fatal flaw when you start your business starting with the wrong idea. It could be a fatal flaw if you have a great idea, but you execute it the wrong way because you’re stubborn in your execution.

Jennifer: I actually genuinely think that potentially one of the worst things that a human can be is stubborn. You cannot truly build real relationships in your life if you’re a stubborn person. You have to understand how to adapt in a relationship and how to grow and how to be a different kind of person over time. How do you become a better mom? How do you become a better wife? How do you become a better leader? Like, you can’t be stubborn to where you once were. And I just would say to people that if they see that quality in themselves, to me, no more than anything, that’s going to be the thing that gets in their way.

Adam: And you’ve had to deal with plenty of challenges along the way. A big one was COVID, which was a potentially fatal blow to your business. You were able to overcome it. We’re here now talking and you shared how you’re on this turnaround path. What were the keys to leading through the crisis? What advice do you have for anyone listening to this conversation on how to lead through the difficult moments that they face?

Jennifer: I think the thing that got me through COVID was that I fundamentally have always believed in this longer-term vision of what we were building and the mission that we had to help women achieve their best lives and help them feel confident every single day. And so having a mission is so important when things get tough because it’s your why, you’re going to still continue. But as a leader, leading through a crisis like COVID where revenue fundamentally disappeared for us was about continuous forward momentum. and dealing with one problem at a time. COVID was such a disastrous situation for a business like Rent the Runway that had I taken the time to sit down and think through all of the negative contingencies and try to map everything out at the very beginning without the information, first of all, you would have psyched yourself out. You would have made yourself terrified. Thank God that you just are dealing with the first issue, then you solve that, you deal with the second issue, you move forward, you take another step, you deal with the next problem. You have to just continuously keep moving. And that forward momentum is sometimes enough to propel you to that next phase. There was no real magic to it beyond belief in the long-term vision or mission. And then the forward momentum of what’s my biggest problem, let me solve that, check that off the list. Let me now move to my next biggest problem and solve that, and check that off the list. And I love this company, and I love this team. And so it felt like I needed to save the company that so many hundreds and thousands of people have dedicated their time and their heart to.

Adam: And Jenn, that sounds like a simple formula, but it’s such profound advice. And it’s advice that any of us can apply to our lives every day.

Jennifer: I think that our ambitious people tend to overthink things. And overthinking is often to your detriment. If I would have overthought COVID, I would have overthought myself out of a job. I would have left immediately and swung to whatever was going to be the safest next role for myself and for my team. It’s the opposite of what we’re taught. We’re taught to be thinkers. We go to school and you’re taught to be so strategic and think everything through and think every decision through, but sometimes just go based on your gut. I knew that Rent the Runway needed to exist. I knew that Rent the Runway, that I needed to save the company. How was I going to do that? Through action, through just dealing with the big problem in front of me, like understanding what was a big problem, what was a small problem and only focusing on the big problems and just continuously doing it. And that is a choice. One of our core values of this company, and one of the core values that really has guided my life, is happiness and positivity is a choice. Life is hard. Building a company is really, really, really hard. And you can choose to wake up every day and overthink all of the hard stuff and how difficult it is and the slug and whatever. Or you can choose to move forward, be positive, choose to have a good attitude about how you’re going to experience that day, and just do it. I literally think it’s about a mindset shift, and that mindset shift for me, I’m not telling you that like there weren’t times during COVID where I was super depressed and that things were extremely emotionally difficult for me. It was because I was in such fear that this company that I love so much and that I built alongside all these people that I love so much would die. So I was in fear. But at a certain point, I recognized this fear is doing nothing for me. And I have to actually just change my mindset. Stop the woe is me. It freaking sucks that there was a once in a hundred-year pandemic that affected my business more than it affected 99% of businesses out there. Okay, fine. Let me feel sorry for myself for a minute and then let me move on. Because miring it is not doing anything for my own happiness, let alone it’s not doing anything for the company. So I think COVID and like being in the depths of fear and despair at the beginning of COVID, was what enabled this massive mindset shift for me of, you know what, let me just focus on the next best move and just be super action oriented and stop overthinking and just go. Half of what you do is gonna be wrong anyway, so why overthink it? Make a decision, analyze that decision, and understand whether it was a good decision or bad, and iterate on it in one way or the other, and use your gut. I know enough about this consumer, this industry, this business at this point that my gut is more right than it’s wrong. And I’ve learned how to really listen to it and be very confident in my decision-making ability.

Adam: I love it. Jenn, what do you believe are the key characteristics of the very best leaders, and what can anyone do to become a better leader?

Jennifer: One of the things that I’ve learned is that. And I’ve learned this not only from my own leadership of Rent the Runway and seeing other leaders contribute to this company over the last 15 years in really amazing ways, but I’ve learned it from sitting on public boards, from being involved in private companies and helping to guide those private companies, advising companies. There are so many different versions of what a great CEO and what a great leader look like. All of those versions correspond authentically to who that person uniquely is. So, how can I be the best leader based on who I am authentically as a person? What are my greatest strengths, and how am I accentuating those strengths in terms of how I prioritize my time? My contributions to Rent the Runway have to be based on what my greatest strengths are. not just based on what is required as a CEO. So I happen to be someone where my greatest strengths are about recognition and building of talent. I have great EQ, and I can understand when someone is awesome at what they do, and I can put them in the right role to set themselves and set the business up for success. So I have a superpower related to talent. I have a great strength related to customer vision and industry vision, so I understand kind of the strategy of where we want to go, and that really corresponds to our product strategy and our marketing strategy. And I’m a great relationship person, so I can be effective when it comes to conversations with our brand partners, when it comes to business development conversations, partnerships, sales, investors, et cetera. But those three strains leave out a whole host of other strains that we need at this business to be successful. And so are there other leaders that, you know, could be great leaders for Rent the Runway? Yes, of course. They would just build different teams around themselves. So what I’ve learned is that having enough self-awareness as a leader to understand what it is that you’re really, really great at, and lean into that. Don’t be ashamed of leaning into that. Don’t be ashamed of calling it out for your team members around you and saying, here are the things that I’m great at and I want to spend my time doing, and this is the kind of CEO that I’m going to be, and here are the things that I’m not great at. And so one thing for me is that I was such a people person, and I love team building. And part of my EQ related to people is I need to spend time with people in order to understand them, in order to really understand their talent and what they’re able to contribute. And so I knew about myself that I’m the sort of CEO who can only be my best self in an in-person environment. For me, when you put someone behind a Zoom screen and everyone’s just a box, one of my superpowers goes away. Now there are other CEOs where that’s not one of their superpowers to begin with. They can totally lead their team remotely, and they should do that. But it’s like, I know about myself that I’m not going to be able to build the best team for the company unless I’m harnessing this skill set that I have, this power that I have. And it’s related to actually building relationships with people in person. So number one thing that is required to be a great leader is just self-awareness and deep introspectio,n and respect for your own strengths. They’re going to be totally different from mine. And knowing that you should build a team around those strengths.

Adam: Jenn, what can anyone listening to this conversation do to become more successful personally and professionally?

Jennifer: Go after it. People wait too long to go after the life that they want to have. And it’s evidenced in so many ways, small ways and big ways, but I see it in people not speaking up in a meeting, not actually expressing their idea, not going after the partner that they really want, not asking someone out on the date, people just being too hesitant about their own life. Like, you only have one life. What’s the goal? The goal is to lead a happy life. How are you going to lead a happy life? by being around people you love and doing things that you love. And you’re not going to be able to get there unless you go after it. Great things don’t just happen. I don’t think that anything just falls into your place. Everything has to be pursued. Love needs to be pursued. Relationships need to be pursued. Your dream career needs to be pursued. Your friendships need to be pursued. Everything. And being aggressive about going after what you want and realizing that like, it may, might take some time to get there, but like the pursuit is everything. That’s what life is all about. Stop waiting for the perfect moment. There’s never the perfect moment. You’ll never be ready. No entrepreneur that is successful was ever qualified to run their company at the beginning. No one. Everyone was just going after some harebrained, crazy idea. Jump into the deep end of the pool and go after it. And we have this core value around the runway that’s called dream big and go after it. I think that we in our culture have really learned how to dream big. I think everyone does have a big dream for their life, but it’s not about dreaming big. It’s about going after it and making it happen. And it’s really to that point of what’s the next best move. And how could you make that big move? How can you spend your time on getting to whatever is going to make you happy? You have nothing to lose. No one has anything to lose. The thing that you have to lose is wasting a single day of your life being around people that you don’t care for, doing things that you don’t care for. You’ve got to go for it. And I bring this philosophy to everything; it’s not just about your career. It’s about having this big dream for your life and then actually making it happen. I believe that I have manifested the life that I want for myself by being very clear about what it is and then going after it.

Adam: You only have one life, it’s yours. Get in the driver’s seat, take control, take ownership, get started. Never too early, never too late. No better time than right now. Jenn, thank you for all the great advice, and thank you for being a part of Thirty Minute Mentors.

Jennifer: Thank you so much for having me. I really appreciate it.

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Adam Mendler

Adam Mendler is a nationally recognized authority on leadership and is the creator and host of Thirty Minute Mentors, where he regularly elicits insights from America's top CEOs, founders, athletes, celebrities, and political and military leaders. Adam draws upon his unique background and lessons learned from time spent with America’s top leaders in delivering perspective-shifting insights as a keynote speaker to businesses, universities, and non-profit organizations. A Los Angeles native and lifelong Angels fan, Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders.

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