It’s NOT Too Late To Reinvent Yourself, Do This NOW with Julie Wainwright

This is a transcript of a YouTube podcast episode (Lori Harder hosting Julie Wainwright) focused on reinvention, risk-taking, and building companies. Early content covers midlife choices about rebirth versus stagnation, Wainwright's risk tolerance shaped by artist parents and a childhood of informal risk (motorcycles, go-karts), and major family hardship (mother misdiagnosed then diagnosed with multiple sclerosis) that created early responsibility. The transcript then traces Wainwright's career: brand management at Clorox, moving to early software startups (taking a large pay cut), leadership roles turning around Berkeley Systems, and later high-profile experiences including Pets.com (shutdown during the dot-com crash) and founding The RealReal (inspiration in 2010, early consignment/luxury marketplace strategy, launching from her house and first sales in June). The tone is candid, reflective, and advisory, emphasizing resilience, timing, and the particular challenges women face raising venture-scale businesses.
Chapters
Being in your 40s is scary because you do feel like I should have made it by now. I should be this. You know, there's all these tapes you run in your head.
It is a lot because you just think you're supposed to be somewhere else. And so much is changing. You're faced with a big choice of how you're going to live out the second half of your life. Like, if you're disappointed with things, are you going to continue on and be sad and depressed and think that this is it, or are you going to give yourself a rebirth?
Those are the only choices.
Julia, welcome to the earn your happy podcast.
Oh, thanks, Lori. Thanks for having me on.
I'm excited to talk to you.
Oh, I'm so excited to chat. You are a wealth of knowledge and you've done so, so many different things. I actually had so much fun reading through your bio and just studying for having you on the podcast. And one of my favorite things that I'm already, like, getting to learn about you and sense about you and that I feel like I want this whole podcast to be around is your ability to take risks.
Your.
What sounds like having a lot of amazing audacity and just, you know, the different things that I wrote down. You have won entrepreneurs most daring. I feel like that's, like, one of the best awards ever. Fast Company's most creative. And you also got retail innovation of the year like this. Let's just. Let's dissect the brain within that. But I want to ask you, do you think that you were born with more risk tolerance than others, or where do you think that came from?
Well, I mean, both of my parents were artists, and my father made his living as an artist. He had his own art and design studio. And that, by its nature, is a creative endeavor. Even though it's a business. It was a business. You know, he did work for Bayer and Kohler and Chevrolet and the old Studebaker, so big firms. So I think that mentality of creating is absolutely part of my DNA. And I mean, I grew up in a time where we all had motorcycles. When I was a kid, I had. That was like one of our. My dad's, like, oh, here we're all gonna ride dirt bikes. And then I would drive it over to my girlfriend's house, and her dad was an undertaker, and he would say he had the local funeral home. He'd say, those are my best customers.
Like, oh, my gosh. And I'd take off on it.
So I think it's a combination of the Art background and then having motorcycles. We had go karts. We. You know, we were always doing things that probably wouldn't do. Now, for a person who's, you know, we. My brother was riding one when he was 10. Unless they were out in a track with a helmet. I don't even remember us wearing helmets, which is insane. Um, but the other thing, which I. When, you know, looking back at my career, which I find interesting, I had to make my own way. I didn't. Basically, when I got out of college, my parents were like, okay, you're done. Have fun. Make your money. And if anything, I was the one helping out my sisters with money. And at one point, my father got into a situation. And so when I look back, I'm like, I was taking these risks, but I didn't have a safety net. So that's a little insane. You know, It's a little insane. I just finished Barry Diller's book, which is great, called who Knew? And he's a consummate risk taker. But he makes it clear throughout the entire book he never had to worry about money. And I was always worried about money. But I think also the value of my parents was they always said to me, you're smart. You can figure things out. And I think the combination of having creative parents who love, especially my dad, loved to have fun, he loved to play, and then having that embedded in me as a child. I mean, very early on, they would say, you know, what do you think? You're smart. You can figure things out. And I think those two things, because when I look back, I'm like, wow, it could have gone terribly wrong.
You know, because I didn't have a safety net. If I fell, it would.
It.
You know, I would follow through. So, you know, that was pure hutzvah. It was just pure guts, I guess.
What would you say, looking back? Can you pinpoint maybe, you know, I. I think as like, ages, like, 12 to, I don't know, even, like, 17. What were some things that you felt, if you can remember, that were, like, confidence builders for yourself, where you're like, oh, I can. I can, like, rely on myself. I can count on myself.
Well, I mean, Laurie, I had a situation when I was 8, and it got worse when I was 16, but my mother ended up. I'm the oldest of four, and my mother ended up in the hospital, and they said she was dying when I was eight. She didn't die. She was misdiagnosed. But then she got really bad when I was 16. But at the age of 8, my father looked at me and said, I'm going to really need to rely on you. I was the oldest of four. Wow. So then the next child was four. So I was eight. Then there was a four year old and there was a two year old, and then there was a newborn. Wow. And I think that taking on that responsibility at an early age. And then When I was 16, my mother was properly diagnosed after a series of really troubling health incidents where they couldn't figure it out. And she had multiple sclerosis. Hmm. And then sadly, it got, you know, her life got progressively worse because she had such a bad attack. She had an intermittent form of it, but she had such a bad incident that it got worse. So I would say having that hardship at a young age, where you felt like you had to step up, also informed my teenage years and high school years. I mean, high school was hard because we did move school systems. And so, you know, I had the whole mean girl situation, but I also had a couple really good friends that I'm still friends with, but I really did have a serious mean girl situation. And one of my old high school boyfriends, when my father died, came to his funeral. My father died about five years ago, so I hadn't seen him for ages. And he said to me, do you remember? And he was on. He was like the star football player at the time. He said, do you remember how none of the girls would talk to you?
And I said, yes.
You're like, yeah, I'm still traumatized.
He said that none of the cheerleaders would talk to him. And I'm like, oh, I'm sorry. That really was a hardship.
So, you know, but having. All right, if you just put those three things together, being told you're smart at a young age and taking on a big responsibility, you know, and feeling the weight of it, even at when you're eight forward. And then. And I was smart in school, so I did well in school. I think that even got me through the mean girl stuff because I thought, you know what? Honestly, on some level, I felt sorry for them because they didn't know me. I mean, I was like, I came into a new school system when I was a freshman and high school, and I. And I didn't have any history. And it. I mean, it was really bad at times, but I'm like, well, they don't know me. And luckily I had some grounding before that, and I had responsibilities at home. And then I was dating the star.
Football player, so we made all that Mean girl stuff.
Worse, you know?
Yeah, absolutely.
So wait, I have one more high school story which is sort of funny. Not funny, but it, it was actually a positive. So when I was a sophomore, I was homecoming queen, which made everything else worse. Right? So you have all that drama going on, but there was one kid who's now or I or was ended up being a judge in Chicago.
I don't want to give his name.
Because I did talk to him about it at one point and he came up to me in a very sort of matter of fact way and he said, you know, you're cute, but let's face it, you're not beautiful. So let's make sure you keep those grades up.
Like he was acting like my dad or something. And he was my age. His name was Stuart.
I won't give his last name.
And when you think about, I still remember, I remember that so clear.
And I remember I burst out laughing. It didn't affect me negatively.
I'm like, okay, Stuart, I got this. I'll keep that. I'll keep going. I'll keep learning.
Keep.
Can you imagine though, some kid, I.
Told him to that he goes, oh.
My God, it was such a pompous ass in high school anyway, remember it? Oh, he did remember, remember. Because I think probably something in his high school brain thought that first of.
All, I did laugh, so at least you know, I didn't cry, thank goodness.
And you know, something in his high school brain was like, probably thought it.
Was wrong even after it came out.
Of his mouth, you know. But yeah, those things all inform me, I would say.
All these little. It's interesting though, because all of these things could have happened to someone else and they, they may not have obviously turned them into what you turn them into. So where do you think you started to look at them? And like, did you extract the lessons right away? Were you like, okay, this is happening for me? Or at what point did you realize, like, wow, all of those things actually did happen for me?
You know, when you're young and your mother's ill, that take took a lot of your psyche. You couldn't really have time for the other type of things. And then I would say the you2 things. A lot of other things. My father did start his own business. He loved his work, loved it. And that informed me. I loved learning. This is another thing. I do remember coming home in grade school and saying, you know, kids don't like smart kids. And my mom and dad sat me down and said, well, what are you going to do about It I said I'm going to keep learning, it's fun. So I loved learning. He loved his work and I think that was enough because look, there was a lot of drama with her illness and then and it. And it wasn't well understood. So we did have this very negative thing happening in the background. And then she became quite really self medicated with alcohol. So like everything sort of got grim and you know, to think that she was dying. So I would say I didn't really have much of a mother from the age of about 10 on because of her health issues, but I had a strong father and that all I knew that I knew that going from forward and also, you know, when you're a kid and you're looking around and this was a long time ago, but we're sort of getting sadly reversing on these things. And you see your father loving his job and you see your mother's friends not loving their life necessarily and not having their own money or having their own careers. And when you get older you realize some of their husbands were having affairs with other people in the neighborhood. You know, when you're in your teens, those things come out sometimes and then you see sort of these women who had never worked and charted their own way having a really hard time because they have to make hard decisions, stay with someone who cheated on them, but then they don't have a skill set, they're still raising their children. And all of that was apparent to me and my teens. So I would say I knew I wanted to work, I loved again, I had a person in my life, my father, who loved his work and found it very fulfilling and creative. I also saw life was tenuous with my mother's illness. Can you imagine at 28 years old having four children, the one who was, you know, basically nine months old and saying, you know, being told you're dying. I mean this happens obviously every day. But you know, their, their life was mi. Oh, the other thing is my dad had just started his own business that he was a year older than her and started it about six months before she went into the hospital. So here. So he's trying to get his business going, his wife is. Comes out of the hospital, but still isn't right. And I would say all of that so soup just gave. And watching women who didn't have their own work and didn't have their own life, all of that pushed me to be who I was. And really. And the, the safety net thing when I look back is pretty odd because if I wouldn't have figured things out. Like, I was told I could. I, you know, who knows what would have happened? And look, you know, it's still hard for women, and it's still hard for women to get ahead. So I think I just. Just said, like, nobody's gonna stop me. It was just like, you know, resilience and wasn't fear, though, but it really was resilience and also loving. I loved the tech world. I mean, I love it. I. I joined it early, and when you were in good companies doing something super cool and solving really good problems, you felt it was exciting, it was new, it was evolving so quickly. Everyone was on a learning curve, and because it was such a young industry, it provided tons of opportunities. And not until I got to my late 40s did I go, oh, looks like my ride's over. I had a good ride. But, you know, that's when I had to figure things out, really figure things out.
But I love your timeline, too. Like, there's, you know, I'm in my mid-40s right now, and so many women are like, I should be further ahead. I should be this, I should be that. I'm like, I. I get it. And also, I feel like we're just gathering all the life experiences now to start doing some really big things in our lives or to start thinking about them. So I absolutely love your timeline, which we'll talk about. But let's go. I would love for you to think back to what was the first big risk that you took in your career that maybe you didn't even realize was a big risk? Because you do have a much higher risk tolerance because of the things you.
Went through and how you were raised.
But what would you say to the outside world was the first big, like, leap or risk that you went for?
Well, I'll tell you the one that was told to me that I was really making a dumb move. All right? And. And I started my career at Clorox in brand management, and I was the second undergraduate they had ever hired. And it was a great learning curve. But my form, this is a little.
Bit of a lot.
But my former boss's wife, I had a great boss. My first boss was a guy named Tom LeFever at Clorox, and he left after about three years to join a startup. His wife then called me about another startup called Software Publishing, which was one of the first software companies. I was probably 24, 25, maybe 25. And they asked me to take a salary cut, a big one. Almost half of my salary cut. And it was like a commute of about 45 miles. So. And I thought, this is the future. I'm going to do it. And I went into the general manager's office at. Because I resigned to HR and my boss, but then the general manager of the division I worked at at Clarkson to meet me. And he had one of those scary doors that you read about with Matt Lauer, you know, where you press a button. There's no door handles. He had one of those best. So he would press a button and the door shut. There were no. There was no way you were leaving. Well, that. Because he controlled the door. So he had one of those. And he. I walk in. First time I'd ever met with him alone, without my boss in the meeting, because we certainly met with him regularly. But he said, you know, you're making the biggest mistake of your life. And he said, I can raise the price of Clorox liquid bleached by half a penny and make more revenue than that company will ever make. And he then said, I'm never going to work with people that are as smart as I met at Clorox ever again. And he also said, and you decided to take a cut. So they. Obviously, I've been like, oh, yeah, I'm taking a cut, and you're taking a cut in salary to do this. And he said, you know, when you leave here, there's no coming back. And I remember looking at him and saying, but I'm. I can make these mistakes. I'm young. Wow. And. But I also. I mean, I was hyper aware of what I was leaving, but I was also hyper aware that when I looked up above me at the time, and, you know, this was a long time ago, there were no women above me. There was no one that looked like me. In jobs of one person who had been a brand manager, that was great. There were a lot of brand managers that were women, but no one made it past that. And that's. That was my next move because I'd already been promoted and so twice. So then it was. The next job would be a brand manager. Now, they bring people in at that level, but here they had a program anyway. And when my most brilliant brand manager I'd ever met, when she was ready for a promotion out of that job, they put her in hr. And I'm like, that's not what I want to do. I want to run a pnl. But I did go down there. I never even worried about this company succeeding. This small company. It got to a. Did go public. I got to about $600 million. And they introduced the first presentation package, which was Harvard graphics, which PowerPoint then copied. All right, so they did. We did some really, really cool things. But, you know, I did leave the safety of a large company with a great training program to jump into this other world. Um, I would say, even so I was cognizant of it, But I did think, I can make mistakes. I'm young. Mm.
I mean, that's a pretty. From every story that you've told, there was just massive self awareness and also self trust, which is huge. So you were talking about that in your 40s, like, you had a nice ride with all of these different companies and all the experience that you got. So tell me about that moment of deciding to go on your own and what that was.
So I had been the CEO of a company called Pets.com that I shut down during the dot com boom and had had so much negative press, personally, the company got negative press. I still get asked about it because we had this sock puppet, the pets.com sock puppet, which I have one of the original ones here in my house still and, like, right around the corner. Anyway, the world was. I mean, it was harsh, and they were harsh on any company that started then and failed. But pets.com became the lightning rod. And I believe, because we had a brand with a. With a, you know, this little mascot that was sort of taking over, and the world had changed, where founders were now considered not just people that the venture capitalists wanted to get behind. Usually they wanted to replace a founder with a professional CEO type. And I'd been a CEO twice before pets.com so I was the CEO faster than most people. One was with a company called Berkeley Systems that had the flying toaster in the game. You don't know jack. And that was sold. The next was a movie site, a precursor to Netflix, that only sold movies called real r e l.com that was sold. Then I went on to pets.com and that was shut down. So I would say no one in the industry wanted to hire a person who had a big failure behind them on pets. Someone that the press would talk about, like, oh, look where this person ended up. And there was an age discrimination. And then, really, venture capital firms had decided that companies without their founders were going. Were floundering. And we're going to work to make the founder a better CEO than bring in a professional leader if the founder wanted to do it. All of those things combined meant I was unemployable. And so then. And. And a Recruiter told me that to my face, you're like, no one's going to give you a job anymore, so get over it, you know? And so then I had to figure out really what I was going to do. And I was. I mean, I was working a little bit, I would say at the age of 52 is when I'm like, I got to figure this out because I. I'm going to run out. And I'd had a divorce by then, so I'm going to run out of money, you know. And it was then I figured that I would place a bet on myself. I would give myself two years to see if I could make it successful. But I also put my house on the market, which was my biggest asset. I only had two years of cash in the bank. Wow. But my house was paid for, so I'm like, I'm going to put the house on the market and figure it out.
So you kind of put yourself in a no safety net situation once again.
I know.
We know you operate good in that, though. You know, I can relate to that. Pretty. And you resonate. Oh, yes, yes, yes.
And that's not where you want to.
Be where you want to be, but it sure can be powerful. Sometimes it's really easy to get comfortable in what, you know, like, it. Sometimes, you know, there's this like, level of discomfort that you are so used to, but because you're just sort of comfortable, you can stay there forever. So it gets interesting. Like having to almost, almost recreate for yourself discomfort to like grow again, you know. So I. I love that story. Okay, so we have two years. You have two years on the clock. And what are the questions you start asking yourself around what you're going to start next and what is coming to you?
So I knew I wanted to do another E Commerce business because I loved it. I absolutely loved it. And then it was analyzing what Amazon could do and couldn't do and putting together a matrix. And I had lots of ideas. I kept exploring them. And one of them, which I was convinced I'll never do is luxury. But I also thought, I'll never do a luxury brand. I not going to create my own luxury brand.
Right.
So, all right, so this whole, like, shock realization was August of 2010. Then now it's November. I'm shopping with a girlfriend in the boutique. I have no ideas. I'm not panicked yet. I should have been. But I figured, no, something will come. Something I'll figure. You know, I still. But I really, I should have been panic and, And I would have advised someone if I was advising them.
You should be panic now. You should be. Anyway, I'm shopping with a girlfriend and.
It'S a little boutique down in Menlo Park. It was full price. In the front, they sold shoes called Head Over Heels. In the back, it had this beautifully merchandise area called the Vault. And it was all consignment and it was all luxury brands. And that's where my friend shopped. Her name's Ann Winblad. So here's Ann who, who, if people have ever heard of her, she's very wealthy venture capitalist, very successful, and she goes right to the beautiful things at a great price. I'd never seen her walk in a consignment store before, ever. So when she completed her transactions, we got out. I started questioning her because I'm like, you know, have you ever shopped in consignment store? No. Would you ever shop on ebay? No. She said, I would never do that. Too many fakes. I don't want to deal with someone on price haggling either. Have you ever consigned? No, it's too hard. I'm like, well, you just bought consignment. How do you feel about that? She goes, I got a great deal. Are you kidding me? And that's it. I'm like, that's my luxury entrant. And I thought. So I kept questioning her, and sadly she drove, so she had to hear me all the way back.
It was quite a ways to get home.
And. And then I called the owner of the store the next day, who was a female who had been in tech before, and decided, oh, she wanted a brick and mortar store and she was raising a daughter. So she didn't get back to me for quite a while. She couldn't. You know, was also going into the holidays, but between that time in November and March, the beginning of March, I had a name, I had a business. I actually went to a friend and took out a second mortgage on my house. I had some money to get started, and I'm like, I'm going to do this. I'm going to, like, make it happen. But it was that light bulb going on, and I'm like, this is great. And the structure is the structure of the real, real. Now for the consigner, we're going to make it easy. So here's my friend who had never. Anne, who had never consigned before. She had boxes of luxury product in her house. Wow. And she'd sometimes give them to her sister, but mostly her sister. They Were different sizes, what, you know, different taste. And so, you know, went to her, went to friends, started getting consignment. She said it was way too hard. I'm like, well, then we're going to pick it up, right? And also we're not taking everything. We're not going to be. We are going to be luxury focused. So we're going to take it up. We're going to take the brands that have the highest resale value so that I knew we're going to have a service for the consigner. And this had never been done before. All right, with basically a sales team. Number two, I knew we had to set the price because the Internet marketplace is always going to be smarter than the individual and the individual pricing is never going to have the same information that you will on a corporate aggregated level. So I knew we were going to set the price based on sell, you know, the best price for the consigner, but also fastest sell through. I knew we were going to have a sales team for the consumer. I knew we had to authenticate and we had to get started right away with that. It had to be an authentic product we're selling. And I knew we'd take returns. So that was the structure of the business, which meant I need, I needed a warehouse. And also I knew we had to make consignment cool, which, by the way, people forget the realreal was the one to make it cool. And we did that intentionally. But I also knew I'm not cool, so I couldn't make it cool. I needed a really good merchant that knew how to make things look contemporary, to mix what was now whatever style was, to make it look like it. Whatever you're buying from a consigned business like us, you could mix it in and make it look contemporary, make it look on trend, put these things together. And that was Rati Levesque, who's now CEO. So she was the first employee and she had a brick and mortar store. She was in her mid, early 20s, maybe late, late, late, probably 24, 25, I don't know. She was young and she was getting ready. She shut her stores down to her one store to join me as the merchant. But we did everything and we started in my house. I moved all the furniture to the side. I had to move my. The guy who I was living with to the side. That didn't work out very well. He ended up failing. I mean, that was probably, that was definitely for the better anyway. But we started in my house and then I Got a our first warehouse before we shipped our first product which was in June. So it went from getting the inspiration in November, finding a way to get funding and then I was raising money by the way, so I had even more money by June and shipping in mid June. And it was Rachi and I and like an intern and I think that was it to get started and then a friend who would drop in and just help us. Oh I know it was insane and but I, I knew our first sale was. I knew once we had our first sale everything sold out in like 20 minutes. It was gone. And we only had 30 items on the site. It was just gone. Gone.
Wow. So what do you think? You know, women are always told to think big, but what do you think? What do you think that you did within that or what do you think are the moves that women need to be thinking of with their business?
Like how much women would think big? You know, there's an article circulating that I got a copy chat GPT when asked how many women that they know about obviously. So this was through chat GBT have have with that are not celebrities have built a business over a billion dollars. There's only 11. It found 11 of us. Wow. All right, come on, that is bad. And some of the people were co founders though they weren't a single founder. So if you think about that, it's like come. I mean now if you add celebrities in it's much bigger. But if you do it the, you know, the way where people don't really know who you are. So here's what I think. Women need to do it. First of all, you have to want to build this because it takes and your values have to be aligned. The beauty of doing it when I did it at my age, sadly I'd been through a divorce. But you know that that urge to get married and have children was sort of past me, you know, so that that period is hard on women. Now I was and my mother sadly had passed. All right. So I didn't have my parents to take care of. I did later with my dad, but it was pretty self sufficient in the end. So I had this time. And by the way, we didn't have children when I was married. I went through that whole time in my 40s, like should I, should I not what? And because we got a divorce when I was 42 and I'm like this is the worst. You know, so it. So I had to figure that out. But then once I was comfortable, like no, I'm not going to be A single mom on purpose. I didn't have those outside pulls that are real and really important. So my, and I didn't have a safety net so I had to figure something out. But I was also all in. So my, my values were aligned, my timing was align the beauty of being healthy in your late 40s and 50s. I was more mature, I was more focused, I had more things to draw from and I had contacts in the venture capital world. In order for me to leverage those contacts, I had to think big. I couldn't bring them a small business idea that wasn't fundable. You know, so then it comes down, what market are you serving? Is it big enough? Can you build $1 billion business now? Right now it's a I crazy here and people are raising billions of dollars. But that's not normal. Normally it's like you go there, you get a lot of rejections. You're. If you're lucky, you raise a million in seed or 2 million in seed and then maybe you get around for 10 million. But it's all hard won. But no one's going to give you money if your idea isn't big enough. And I was comfortable in the venture capital world, raising, developing a pitch and raising and I why don't women do it? There's systemic reasons, there's, there's timing reasons, there's natural bias, I think against them. I think it's harder. And if it was, if it was equal, then women, there wouldn't be 10 of us that have done it. You know, this is probably a us bias, but if it was equal there would be more women wanting to. But I think it's cultural, it's societal and I also think there's not enough stories out there. So people need to sort of see themselves, you know, and feel like, oh, if that person can do it, I can do it. You know, the more stories you have out there, which is something that you can, you're bringing forth that people can overcome this. Sometimes you just need to hear you can do it and then you can say, okay, because look, I didn't go to Harvard, I didn't go to MIT. I'm not like a bro, you know, and I raised money in my 50s and I did it in my 50s. So. And I took a company public from an idea in my kitchen to going public, which something like Only less than 2% of all companies do that. So. But I'm not, I mean yes, I'm special because on, you know, luckily I had some things in my childhood, but people have all that inside of them.
Yeah. I think we need to find the stories, because if you can't see it, you literally can't be it, because it's not within your, like, realm. And honestly, I, um. I'm just so resonating with your story, and I'm trying to figure out what has made me also raise money and start a company, because that was not in my world. But it became possible to me when I started hanging out with different men, who then also introduced me to different groups of women. But I had to sit at the tables and, like, learn and hear. And I think what's really powerful about your story is, you know, you were talking about you were one of the only women in a lot of the places that you were at. And I think women get intimidated by that, and. Except you got let in on conversations that have now allowed you to, like, negotiate different things or understand what that looks like to raise money from, you know, VCs. And I think we just. Like you said, it's getting stories like this out there. Having to be able to have access to those conversations is what will change the game. And I think I. I think we're just at the very beginning where the women doing it, like, we want to help those other women, but we're still trying to make our companies work. And so it's like, we. We equally, as women, have a really responsibility. It's like, we. We're supposed to be successful in these companies. We've never really done yet or, like, had a lot of help in, and also bring the conversation back to the other women at camp, you know, like. And, like, bring them into it so you couldn't be more right with, like, it's. We have to be having these conversations so other women can see it. Otherwise, it just feels too scary to even ask questions about. And I get that. That's how I felt for a really, really long time. But I love, love, love your story because you were in your. You're in your late 40s and 50s when you started asking this. And so I think so many women. There's still just this incredible amount of time to go and start something that you love and that you can do and that you can pour yourself into. I also.
I do want to give. I mean, remember I talked about Anne Winblad, who I was shopping with? Look, I was at the company Berkeley Systems, and I was VP of Sales and marketing. When I came in, that company just look like it was gonna fail. All right? And you just. That would have been my first big failure. And also I had done a stint with software publishing and another company. And I lived overseas for six years, which was amazing, and ran international, which is a whole nother fabulous thing opportunity that I embraced when it came to me. I'm like, I've got a password, I'll do it. But what that meant was it took me out of the US and what was happening in the US and sort of the heartbeat of companies, and I wasn't networking. So now I get back to the States and I get this opportunity at a company called Berkeley Systems. And it was unbeknownst to the board, and whenblatt was on the board, it was about ready to fail big time. And I did. What happened was this is back when you had to sell into retail software. It wasn't downloadable. They had shoved a lot of product in the channel that had no pull through. So even though they had reported a great quarter, I think something like 80% of it was coming back the first quarter of the next year. And that was my first time. That was right when I started the job, which put them in a serious cash flow situation. And the good news, I had a great CFO to work with. And the founder was a tech guy, really smart, visionary tech guy. But he had didn't know what to do and the company's failing. So I worked with the CFO and we put together a plan. I presented to the board of here's how we can turn this company around and here's the steps that we need to take. Then they're like, okay, the next next day I get a call. Well, we had our meeting and by the way, the founder and his wife, which was kind of weird, were both on the board and, and the investors. Well, we had our meeting and we want you to run it, and you're now the president. Do you want to do it?
And I'm like, okay, okay.
And I was so kind of shocked because I thought, what are they? I mean, who knew what they were going to do? Because I basically said all these mistakes were made, you know, in this last year. Here's how we get out of it. Here's what we need to focus on going forward. And. And then they called me like, okay, you're president. And I, when I was driving home that night and I was still married, instead of taking my turn, I almost went. It's like, if anyone knows California Highway 80. And I was on the East Bay. I almost went to Sacramento before I realized that. I'm like, because I'm thinking, I'm driving. I'm like, you know, am I ready for this? Can I do it? And I get home, and this is before cell phones. My husband's like, where have you been?
I'm like, I don't know. I don't know where I've been. I was almost. I was like, almost two hours.
I was thinking. I was.
I was just thinking. And driving. The American thing we do.
Yeah.
Anyway, I, um. But my life got easier doing that, turning that company around. It was. And. But they. They. Including the founder and Ann gave me that opportunity, and then I started to raise money for the company for the next round, and then they made me CEO. And that, you know, stepping. Offered the opportunity, stepped up for the opportunity, and then found it to be easier because I knew what decisions needed to be made, and I didn't have to convince the founder. The founder. I had to, like, talk to him about it. But it was, like, my decision, and it was absolutely better. Absolutely.
Okay. What I love about that story is you literally created the perfect position for yourself by being brave enough to take a risk to, like, pitch and say, this is where you're going wrong. This is how to save it. Like, a lot of people wouldn't have necessarily thought that or done that. And you propelled your career forward in something that you were great at. Like, you literally got to stand up and show what you could be great at and therefore create a position for yourself. Where do you think women go wrong in, like, trying to get to the next level or scaling their business?
Well, scaling is a whole different story. But I think that, look, there's so much pushback, and if you. If you get sucked into the negative part of being an entrepreneur, which is always hard, and I think lonely. I mean, people don't talk about that a lot, but it's lonely being an entrepreneur. And you think you're faced with problems that no one's had before, or they're uniquely your problems. You really need to sort it out. And there's not a lot of female entrepreneurs. There's not a lot of entrepreneurs, but there certainly aren't a lot of women entrepreneurs. So, you know, I think where they get stuck is a lot of. They spend too much time caving into the opposition, which is monumental. It could be bias against funding. It could be the bro culture. It could be their other women friends are like, why is she doing this? You know, like, there. Maybe she's getting some shade from her other friends. If she's had some success, you never know. But there's enough negativity that it can take you down. And it's also exhausting. I mean, it can be physically exhausting if you're really trying to build something. It. It can also. I'm not talking about. There's so many positives, but, you know, it can be exhausting because, I mean, I would come home and I write about this in my book, Time to Get Real. We should get that in there. But I would come home from Pick Pack and shipping in our little warehouse and answer customer service calls and fall asleep and wake up with, like, pencils, pens stuck in my face because I'd fall asleep on my counter doing that. So you need a lot of energy to start a company. Scaling's a different thing. Then you need the right people, the right market, because some markets you can't scale in. So you need to really make sure there's an right market, the right positioning. Then you need great people, great processes, and usually capital. But all those other things are before the capital. Those all have to be aligned. And then there's timing, because the world could change, and your business plan, your business that was so great could be obsolete. I mean, that's happening now with AI. Either people change or they die. So, you know, all of those things have to be right. That's a lot. But clearly people get it right all the time. But it's like, you know, my story with pets.com, the company that actually wanted me to run pets.com also founded a company called Home Grocer, and they did Napster. So what are those? What happened? If you fast forward 20 years, you've got Chewy.com, you've got Instacart, all right, which is Home Grocer and Web and combined. And you've got Apple Music, which looks a lot like Napster did at the beginning, even though the. The money's worked out. So all of those things. So what was their problem? Timing. So timing has to be right. What was my problem with pets.com? timing. You know, and so that's. Those are a lot of variables. That's why the other thing is, which I had to learn if you fail. And I really had to learn this because everything was, you know, go, go, go, until I did have the failure with Pets and I internalized it. Like, what did I do wrong? You know, you have to brush yourself up and get up again. You have to analyze what's right and what's wrong. And you can't let the negatives, um, the ne. My negative of feeling really did overshadow me when I even look at pictures back then. And I also got a divorce at the same time. But I look at pictures and I'm like, who is that person? That person's, like, internalized this too much. So, you know, I think you have to move. You have to figure out a way to brush yourself up and keep going. And that's not easy. I mean, it's really hard. And it's hard. I don't care. Whatever age you are, it's just hard. Now, I'm going to say, here's what I think. If people have kids, especially young women, putting them in sports, where you have a lot of opportunity to win and fail.










