
Julie Wainwright was told she was “unemployable” at 52. Instead, she built a billion-dollar business.
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Hey everyone, welcome to Her Money. I'm Jean Chatky. If you have ever hit a major bump in your career or your life and thought, well, that's it. I'm done. This episode is for you. Julie Wainwright, my guest on a recent episode of youf Money Map, the show I host for Limra's alliance for Lifetime Income, was once told she was unemployable at age 52. And yet she went on to launch the RealReal, a luxury consignment platform that didn't just disrupt the fashion industry, it became a billion dollar business and a must visit for me. Julie's story is about what happens when you refuse to be defined by failure. In her new book, Time to Get How I Built a Billion Dollar Business that Rocked the Fashion Industry, she shares the messy, unfiltered truth about entrepreneurship starting over and leading with purpose, even when the odds and sometimes the venture capitalists are stacked against you. We'll talk about bouncing back from personal heartbreak and professional setbacks, how age can actually be your superpower, and why you should take a calculated risk on yourself no matter where you are in life. And as always, for more guidance on how to create retirement income you can't outlive, head to protectedincome.org where you can also sign up for their newsletter@protectedincome.org subscribe here's my conversation with Julie Wainwright. Julie, welcome to the show.
B
Hi. Thanks for having me.
C
Oh, thank you so much for being here. Congrats on the new book. It has been described at A look at the messy realities of leadership. What inspired you to write it and how do you think it's different from a typical CEO success story?
B
Well, first of all, it was fun to recap what happened at the RealReal and I've been getting I get so many questions about the business and also about how I overcame what happened@pets.com I decided to put it in a book that I would like to read, which is something that is honest and has sort of warts and all. If I would have read this book before I started the RealReal, I would have made different choices. So I wanted to write something that told the story but also gave practical advice along the way and show where I made mistakes and give people other alternatives, other considerations. We're going to take a quick break.
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B
So let's just go back. That was 25 years ago. This is the 25th year of the dot com bust, as people call it, and pets.com was one of the first companies to shut down. There were I think 1100 other companies after that that had to close their doors. I actually made the decision to shut the company down when it had a net positive work to get money back to shareholders because I didn't believe I was going to be able to get my next round of financing and we needed another hundred million dollars to get to profitability. And back then, way back then, There were about 200 million people on the Internet. So it was so early, by the way, I don't think it was smart of me to shut the business down. In hindsight, although the investors did appreciate it because the early investors still made money. But why I don't think it was smart is no one can predict the future. I really should have taken it as far as I could take it. Now it turns out I was right that the financing market did collapse. But I could have been wrong. There's no crystal ball here. Anyway, Once that happened, pets.com became a poster child for a dot com crash. And it was something that loomed large in my career, really until I had another success, which took years, but it was hard for me to get another job. This is, by the way, after I had two successful exits as a CEO. So I had one failure and it was incredibly hard to get another job in tech. And because the Pets.com Puppet and the company was referenced regularly as a.com implosion symbol, it actually sort of was like a dark cloud around me. And I didn't fully recognize it until a recruiter basically laid it out for me that you mentioned it for my. He really believed my career was over.
C
There's so many interesting data points in everything that you just said. The fact that the original shareholders made money, the fact that if you look at Chewy today, you could see that pets.com had you held on and continued to run the business as you were, would have been a success. It turned out that that was not the only thing that happened to you during that period of time. Your husband asked for a divorce and you. You called it a long winter. How did you get through it, both personally and professionally?
B
It was really hard, I would say, for a long time. I let those two events define me and felt terrible about it. And because there was also public sort of score when I'd go out, you know, people said, aren't you the person who was the CEO of Pepsi.com and they were angry about it because it was a symbol, maybe lost money, who knows. But it altered my personality because I became more introverted. The other thing that's unfortunate, when you're in your 40s and I was 42 when I got a divorce. Such an odd time to get a divorce because we hadn't had kids and we had sort of talked about it, but not really. It wasn't a priority. But then all of a sudden you feel like, well, that's gone. That option's gone as a family anyway. And most people are settling into their marriage, not having their marriage blow up. Maybe that happens another 10 years in their 50s or some in their 60s. But it was a weird time to have that happen. My. I didn't put it in the book, but my mother also died, like, within a year, which was, on one level, a blessing because she was very ill. But it's still a psychic blow.
C
Oh, it's awful. Yeah.
B
So you had all these things piling on. What I did to get back to my center was. Well, I never stopped exercising, so that gave me an opportunity to get rid of excess energy. But being around creative people, artists, a lot of artists, I joined a couple arts organizations. Being out in nature helped. And to be honest, time helped because I got tired of being in a funk, you know? So I just had to say, this is not how I want to live the rest of my life. I wish I would have snapped out of it sooner. I didn't. But once I did, there was no going back.
C
It's so interesting, Kathleen said in the comments, when it rains, it pours. And she's certainly right. I got divorced at 40. My father died right around that time. A lot of different negative things sort of hit all at once. And so I understand what you're talking about. But you did rebound, and you rebounded in such a big way. At a Decade later, age 53, you launched the RealReal from your home. Why? And what did those early days look like?
B
So this is funny because actually, I started at my home, but I rented a small warehouse, about 2,500 square feet, about a month before we launched, because I couldn't really pick, pack, and ship from my house. It was definitely a starter warehouse. I mean, when I wrote about it in the book, and this is true, you walked in. The entry level had, like. It felt like plastic carpet. Like, it crunched like you're walking on cereal or something when you walked in. It wasn't in a good neighborhood. And so I put black plastic bags, like garbage bags on the windows and had them taped up with duct tape. And there was a sandwich shop next door that every morning would cook bacon, so it sort of smelled like bacon inside. Anyway, we didn't launch from. There was, like, one employee that time, and we did launch from this warehouse in San Rafael. And honestly, it was exhilarating. It really was, despite the fact that it was, I mean, literally gross. People would walk in to interview, and they'd take a look around and walk back out. It was also a railroad car. So the office was at the front. The photography studio was the next little room. But the photographer had to step into the toilet to take pictures. Oh, my God. And then there was a little alcove where we kept the handbags and shoes and the accountant's desk and huge container store containers. So it would get hot and they would start leaning because it was hot, and they didn't have any structure holding them up. And then the back end was for garments and boxes and pick, pack and ship with a roller door out. So it worked. It did what it was supposed to do. But there's something about getting that gritty and getting down to the basics that felt very pure and real. And honestly, I was financing it, so it was also what I could afford at the time and the risk I was willing to take. Having said that, our first sale, we sold everything out really quickly and did $30,000 the first day. And I was. Then I'm like, this is it. We're on to something. I knew it right away.
C
You did this at a point. You're in your 50s, a lot of people are winding down their careers or just thinking about starting to wind down, and you are just gearing back up again. Did you find ageism biases against people who thought, you know, what are you doing?
B
Well, look, I decided to raise venture capital. So I would say I'm not sure what got me the most. The fact that a lot of the people I was meeting with, I was old enough to be their mother, or the fact that I had had pets.com in my background. Probably the combo was fairly detrimental. And the first person that invested was a woman because she understood the business and was already using the business. I didn't even attempt to raise venture Capital funds for one year after the launch, and we were already at $10 million in sales then. And I knew where we were going. But it was. I knew that, yes, I was a woman over 50, but I also had pets.com in my background. No one was going to give me seed funding except people I knew, and they did. But after that, I needed capital to go forward. And luckily, I met a woman named Maha Ibram at Canem who understood the business, understood what we were trying to do, and loved the business.
C
As you speak to other women entrepreneurs who face those very same challenges when it comes to raising capital or even just starting their own businesses, hanging out their own shingles, what would you tell them about going into it at that point in your life?
B
So, first of all, there's many good things about it. If you're healthy and have high energy, which I was and am still, you can let most of the things that might rattle you in your 20s or 30s or even 40s slip away. So I would say you have more knowledge. Hopefully you're, you know, you're not dealing with roller coaster life. You know, you understand how to maneuver through the good and the bad in life. Chances are you're much more strategic, you're much more to the point. So your focus is clearer about what you need to do. And hopefully you have a good sense of humor by then. Because no matter what business you start, you really need a good sense of humor because things always go wrong and you won't let the things that go wrong actually deter you from the possibility of what can go right. And that is a, in my experience, a learned behavior. I know men are more confident in many ways than women when they start it, but even then, no one's that confident when they start a business. But once you recognize what you can control, how you can problem solve, what you can do to move forward and you know how to look for what success looks like, the other stuff that goes wrong every day and things always go wrong, you can just like, okay, it went wrong, we'll fix it, or this is fixable and you can just move forward. The maturity is really great. And then hopefully, although women do have a bigger burden than most, hopefully you don't have parents, sick parents that you need to take care of and hopefully your children are self sufficient. I would say the beauty is if you know what you want to do and you've got the energy to do it and the inclination, age shouldn't come into it. I think you just have to, your values have to be aligned with what you want to do. Is it the right time in your life? But I did find it easier in my 50s than I did probably in my 20s. I know for a fact in my 20s, 20s and 30s. We're going to take a quick break.
C
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B
I think the biggest mistake I made is once my venture board got off so we took the company public. The venture people that came into the company, some people had had their money in their eight years. They wanted to get off the board so they could sell their stock without being under SEC regulations. So I recommended other board members that were approved and those board members, Board members had never experienced a high growth company before, had no idea what an entrepreneurial journey is like, were not necessarily. One of them had a technical background, but most of them didn't have a technical background and therefore they had a different way of thinking that was more conventional, that didn't map to the business or the way the business was doing business because we were not a conventional company and they had never seen a high growth situation. Like I said, there were two people on the board that had. One wasn't really operational, the other one was and was useful. But then there were four other people including the last money and Guy who had no idea and he didn't get his money out the last money and Guy didn't resign like a smart person and sell his stock. So these people were new. And then we had Covid hit. So it set up this disconnect between what I had to do as the CEO and by the way, it didn't even occur to me that we were so misaligned that they had no idea of anything that I just laid out. They really had never experienced it. So it's almost like we were speaking a different language. Because if I would say, you know, this, this, this, they wouldn't hear it that way because they never even understood it. And I think the other thing is the realreal was and still is incredibly analytically driven with great databases and really driven through a lot of analysis and everything was measured that is not normal. And other more traditional older school ways of business, they're just not data and technology driven. So you know, it was just, it really we were speaking a different language. And where that didn't serve me was when the stock fell and the one board member, the PE guys who didn't get off the board to sell his stock got nervous and thought he could solve the problems. He came after me and I didn't even know it was happening. And they were on. They were all happy to go along with them because things look pretty crazy during COVID and the next year out. So I would say I set myself up to fail. Now look, if we wouldn't have had Covid, my bet is it wouldn't have happened, but, you know, things never go that well. So I would say values weren't aligned on the board. Experience risks weren't aligned. And I was naive and not understanding that. We didn't even speak the same language.
C
Let me just pause you that right there. You were fired from this company that you started, which must have been devastating.
B
Oh, it was absolutely devastating. Now, I say in the book, I didn't help myself because people just don't like to see a woman get mad and have anger. And I did. I lost it in a board meeting. And I was relentless. So I didn't help myself because I couldn't believe lies were being told about me. And I was just trying to work the company through. So that was unfortunate. It was devastating. What was worse was the person they put in after me, who was, in my opinion, completely unqualified and never run a public company again, was more of an old school person. And he. He didn't last long. The good news is he didn't last long. And the person who was the first employee who was the president of the company is now the CEO. And she's great, and that's who my heir apparent with the board's approval. But she was so capable. She had everything except the cfo, HR and sales reporting to her. So she was running operations. And it's just amazing. That's Rachi Levesque. But look, I think, you know, people get fired from companies all the time. Women sadly get fired. Very few women founders live to say another day. But look, I took it from an idea in my kitchen to over a billion dollars, and I took it public as one of the. I think I was the 23rd woman ever to take a company public and created a new industry and raised the awareness of sustainability. And I obviously didn't do it alone. I had a great team. But, you know, there you go, things happen. And luckily, the person that the board put in did get asked to leave, otherwise the company would be in trouble, in my opinion.
C
Now you get asked the question, when do you plan to retire? And you have called that an odd question. Why do you think it's the wrong question to be asking?
B
Well, I just. It's like something from the 50s. It's something that, like, you just think of, oh, I'm gonna go join a country club and play golf or something. I don't understand it. And to be honest, my father had his own business and he never retired until he stopped working about two years before he passed away in his 80s. So it feels senseless. I mean, Retired to what? The truth is, if you're curious and you're engaged in life and you love business, which is really fun and exciting for me, I don't really understand it. I think there's. This is sort of a natural thing. I remember, you know, in my 20s, I thought people in the 40s were old. And in my 60s, I think people in the, you know, the 90s are old. I bet you if I live till 90, I'll think I'm not old at all. So I do think there's just a generational gap. No one my age asked me when I want to retire, but I would say almost every single journalist that talks to me is just shocked that I'm working. And, you know, the question always comes up, don't you have enough money? I mean, for me, it's like, if I didn't love doing something, I would try to figure out something else I'd love doing. But, you know, working is, for me, it's. It's creating.
C
It's exciting part of creating the real, real for you. And I know a little bit of this story, but I'm hoping you'll share. It was emptying out your 401k to start this business. And I've heard that story so many times I can't even tell you. But often I, I hear it from people in their 30s and not from people who are, you know, closer to the age at which we might want to stop working, if that is going to be a thing. How was that for you? What made you decide, this is the road I'm going to go down? Would you recommend that other people make the same bet on themselves?
B
I would never recommend what people do with their money. But I'll tell you why I did what I did. So first of all, when I started the company, I had two years of income in the bank. That's it. Because I had gone through a messy divorce and hadn't made a lot of money between there, so I had two years to live on, which meant I didn't have money to invest in the company. So. Because I didn't know how long it would take and I didn't know if it failed, would I have to then sell my house? And I, you know, you didn't. I didn't want my back up against the wall and all things. And I had a 401k. So I made the decision to. I, I mean, I took it down to like $50,000 to take that money out to put it in the company, because especially after that very first day when we sold 30,000 items, I understood that I had a supply problem, meaning I needed more product in, I didn't have a demand problem, and that this could be a huge hit. And I also realized that venture capital would not come knocking at my door. And as much as I'd knocked, I'd probably get all no's until I could prove the business model. So I knew I had to invest in the company to get it to a good run rate with some predictability. Even though 10 million is sort of nothing, but it's in one year, it's a good proof point. So it was either that or lose. So when we talk about it, it's sort of my heart palpitates. It didn't feel risky. It felt like a calculated risk. When I look back at it, it was pretty risky. But it worked out. It all worked out. My accountant and my. I had a. I mean, I didn't have a lot of money, but I had a. Still had a money manager. They were like, okay. Everyone was taking a deep breath anyway, so it did work out. I wouldn't recommend it. But on the other hand, if you really do believe in yourself and you need capital, then I would say take calculated risks. This was a calculated risk.
C
Risk. As you look into your future, what's next? Is there. Is there another company that you're starting from your kitchen table? Now, the last thing in your bio is not something that people are going to shy away from.
B
I'll tell you what I'm doing right now. So I don't know what's next, but I'm sitting on a couple boards. One's a public company and one is moca, which is the Museum of Contemporary Art. And for Los Angeles, which I'd like to. But I would say every single day I meet with entrepreneurs, almost all females, and I'm helping them or coaching them, talking to them. They're sharing their stories. Tomorrow I'm doing a site visit on an entrepreneur's business. I'm an investor in an early stage venture capital firm called Shaki. Also Mastery, which is another really fascinating venture fund. That's more Venture has some pen Graycroft. So these are all people that supported me, by the way. And another fund called Volition, which is later stage. So I'm helping entrepreneurs move forward, seeing lots of deals, having great meetings. It's very enriching. And then I've been out giving talks and no surprise, most of the people that show up are women and most of them really want to be entrepreneurs. And we can have Honest conversations and safe places. So that's really enriching. So that's where I'm at right now. I don't want to go too far in the future because this is new. Having this kind of, I would say a role where you're in service is new, and it's gratifying.
C
The women entrepreneurs in your office, if you could leave them and leave us with three pieces of advice, what would they be?
B
Give yourself a lot of rope. Give yourself some grace, because things will go right and wrong. So do not beat yourself up, because other people will do that. Learn to treat every experience as a learning experience. Be careful the people you hire. Make sure you have value. Sync. So values and what you hold, its value and experience are really important. So when I've made recommendations for, like, even the board, I would say our values were misaligned. So values are really important. And the last thing is it's not over till it's over. So let's say you fail. You may get up, you may not want to try something for a while. You've got time until you're in the grave. You've got time to try and try again. And oh, one last thing, really, I just hope people laugh a lot when they make mistakes because honestly, that humor gets you through so many things, and most things, when you look at it, are sort of absurd. Let me just tell you one story, just to tell you. The pricing's always hard and people pay a certain amount and they want. This is for used things, and they want something. And I remember someone who shouldn't have answered a customer service line. The woman was really upset about the price of her used shoes. And she's the customer service person who wasn't. She was another employee said, lady, you're talking about used shoes. You realize that? And it was terrible to say to someone because she was emotional. I had to hold up cue cards. But when we got off, she was upset about used shoes, which are sort of funny when you think about it, but you don't want to let the customer know that. All I know is there's more humor in things and you don't beat yourself up.
C
Julie, if we've got people who are looking for more information on you or on the book, where can they find that?
B
So the book Time to Get Real is available at Barnes and Noble, Amazon and some bookstores. For me, I am on Instagram @realreal, Julie, and you can email me at juliehopbc.com that's spelled S H, a k t I v c dot com and that is an early stage seed investment company that I'm helping with and an investor in.
C
I love it so much. Thank you so much. Whether you are continuing to work late in life or thinking of starting your own business, or you just want tips on improving your financial security as you age, be sure to check out the resources available on LIMRA's alliance for Lifetime Income website. It's protectedincome.org Julie, thank you so much for doing this.
B
Oh thank you.
C
If you love today's episode, please take a moment to leave us a five star review on Apple Podcast. Your feedback means the world to me. And if you're ready to keep the money conversation going, HerMoney has three amazing programs designed to help you feel more confident and in control of your money. There's Finance Fix. It's our four week coaching program that helps you rethink your spending, find hidden savings, and make smarter choices for the future. Our Pre Retirement program runs for six weeks and walks you through building a retirement strategy that's personalized for your next chapter. Finally, there's Investing Fix, our investing club for women. It meets every other week on Zoom. It is a supportive space to learn, ask questions, grow your investing confidence and build your portfolio. And your first month is absolutely free. These programs are truly helping level the playing field for women financially. I'd love for you to join us. Hermoney is produced by Haley Pascalides and our music is provided by Video Helper. Thanks so much for listening and we'll talk soon.
Episode: Your Money Map Replay: Julie Wainwright on Reinvention, Risk, and Building The RealReal After 50
Date: November 28, 2025
Guest: Julie Wainwright, founder of The RealReal
This episode explores the remarkable story of Julie Wainwright, who, after suffering a public and personal series of setbacks—including the high-profile collapse of Pets.com and a divorce at age 42—reinvented herself and went on to build The RealReal, a billion-dollar luxury consignment platform, in her 50s. Host Jean Chatzky and Julie dive into the messy, unfiltered truth of entrepreneurship, the reality of risk-taking later in life, ageism and gender bias, and the value of resilience. Julie shares practical insights and advice from her new book, Time to Get Real, and reflects candidly on leadership, boardroom politics, and staying purpose-driven amid adversity.
“I had one failure and it was incredibly hard to get another job in tech... It actually sort of was like a dark cloud around me.”
— Julie Wainwright (09:10)
“Being around creative people, artists… Being out in nature helped. And to be honest, time helped.”
— Julie Wainwright (11:53)
“Our first sale, we sold everything out really quickly and did $30,000 the first day. …I knew it right away.”
— Julie Wainwright (14:10)
“If you know what you want to do and you’ve got the energy to do it and the inclination, age shouldn’t come into it.”
— Julie Wainwright (17:52)
“I took it from an idea in my kitchen to over a billion dollars, and I took it public as one of the…I think I was the 23rd woman ever to take a company public and created a new industry and raised the awareness of sustainability.”
— Julie Wainwright (26:42)
“Retired to what? The truth is, if you’re curious and you’re engaged in life and you love business… I don’t really understand it.”
— Julie Wainwright (27:54)
“Give yourself some grace, because things will go right and wrong. …Do not beat yourself up, because other people will do that.”
— Julie Wainwright (33:44)
“It’s not over till it’s over. …If you fail… you’ve got time until you’re in the grave. You’ve got time to try and try again.”
— Julie Wainwright (34:22)
Frank, funny, and fiercely practical, this conversation with Julie Wainwright is a masterclass in resilience, late-in-life reinvention, and the power of calculated risk. Julie dispels myths about age and entrepreneurship, shares invaluable leadership wisdom from her highest highs and lowest lows, and encourages women to give themselves permission to evolve, make mistakes, and keep moving forward—no matter when or how often life knocks them down.