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All freshly baked with real butter with.
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Banana, chocolate and strawberry flavors. That sounds amazing. Can I have a bite?
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I'm sorry but no.
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Beginning of my career, great training which I got at the Clorox company and brand management after that. I'm a risk taker. I've embraced technology from an early age.
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Julie Wainwright. She was the CEO of one of the first dot coms to go public. And the next day her entire life collapsed. Pets.com shut down. Her husband filed for divorce and the world watched her fall alone.
B
For me, the key thing was I knew the world had changed. Now it's 2011 and the only big player was Amazon. I need to map out what Amazon can't and can do. And one of those opportunities was the luxury market. Then I moved really, really fast.
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And then at 53, she came back with no funding, no team and no second chances. She built the RealReal, a luxury resale empire that reshaped e commerce. She was told she was too old. She proved them all wrong. This is the most brutally honest conversation she's ever had. AI tools we outsource our thinking and we outsource our writing. What do you think is going to happen in 30 years from now?
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Entry level jobs are read in certain areas are being replaced by ChatGPT. Means people on a senior level have to know where you're going. Operating out of fear is always losing. You have to trust in yourself because fear based decisions have failure written all over them.
A
So Julie, thank you for coming on. If you had to describe your career, how would you describe your career?
B
Oh, you know, I was looking. I was thinking about that the other day. I would say two things and they're a little conflicting. I've always wanted to understand how business Operates from multi functions. So I've. Number one, when I was very young, right out of college, I wanted to get great training. All right? Beginning of my career, great training, which I got at the Clorox company and brand management. And then I would say after that, I love. I'm a risk taker in my career and I've embraced technology from an early age. So I understood that what I was seeing in early software development was the future, and I was willing to take risks in companies that were incredibly nascent.
A
Those are. First of all, I didn't even expect you to go right into, like lessons for the audience. But I appreciate you for doing that. I think that those three ideas alone are probably some of the most useful ideas for somebody that's definitely getting started in their career. Just trying to figure out what to do, right. Risk taking, which is very important at any stage. But definitely early on, the fact that you embrace technology, of course that's something that will never go away. But also you mentioned something that's interesting. You mentioned that you got the training. Now why is that interesting to me? That is interesting to me because I think that too many people, especially in 2025, they glorify entrepreneurship and they jump into entrepreneurship and they skip the training part. So they love technology, they love risk, But I feel like everybody just wants to fast forward their life so quickly that they skip all the training, they skip putting in the reps, and I think that's the wrong way to do it. When you started and you sort of first jumped into the workforce, for lack of a better description, how important were some of the things that you learned then that allowed you to succeed multiple times later on in your career?
B
Oh, my gosh. All right. So first of all, I did. I mean, look, I really wanted to get good training and I knew I wanted to go into brand management at a packaged goods company because I wanted to run a P and L. All right? So I knew that for various reasons, including people I knew doing the work. So then it became, well, let's go to a company that has the best training. Here's what I didn't know that has served me like crazy. One of the things that Clorox did, it probably had the. By the way, looking back, probably had the wrong model for where that company was because it wasn't even a billion dollars. It had been spun off by Procter and Gamble and it had to find its own diversification outside the bleach world. But they had structures the size of a Proctor and Gamble company because it was all their management, they didn't rethink how they needed to operate. But I got the benefits of Proctor and Gamble training and everything. Moved by the written word at Clorox, yes, you had to meet people and explain it the doc. But in fact, almost everything you did moved by the written word, which meant your arguing. And they had a very highly stylized way of writing, which also meant when someone looked at it, they understood if it was an analysis paper right away or a recommendation or a research paper. They understood the difference just on the format. And the formats were pretty much baked in so that people knew where to look. Like here's. But what they taught everyone was I call it the Wall Street Journal way of write them. You tell them what you're going to tell them right away. You have a top line sentence, then you support that. So you're like, here's the findings, here's the support for the findings. Here are the conclusions, here's the next steps. Very clear. Now, what that did is it structures your thinking. And by the way, you had to write it in order of priority. So you didn't get this dump. You know, you didn't get this dump of information. What you got is here are the five top things you need to think about. And they're by. By nature, they had to be in priority. Here's what it means for the business, and here's what I'm recommending as next steps. They trained you from day one to write like that. And what I didn't realize until I left, all right, And I left young because I started young. I was one of the youngest people they ever hired. One of the. I was the second undergraduate they ever hired. But what I didn't realize is they were training my thinking. They were giving me a lens, an analytical lens for everything I did. And to this day, that's how I think. I would say one of my strengths is I'm incredibly good at distilling a lot of information down to the key findings of what we need to do and what the implications are and understanding the high order bit. And it all started with Clorox. Now, interestingly enough, I saw you this interestingly enough when I read about how Bezos runs his company. Now, he required a lot of pages of work, but he was also required everything to move by written word. And then you have to defend it. I don't think he was trained that way. But the truth is, if you can't write well, you probably aren't thinking well. And I believe that wholeheartedly. So if you can't construct an argument in business and understand, analyze things. You're most likely not thinking properly about the business. Now that training was invaluable and I brought it forward. I trained my execs, even my at, all the way up till my last execs. They could have 20 years of experience and they still were a mess, to be honest. Their thinking was not that they were. Their thoughts weren't as organized as they should have been. All right, so they needed to organize their thoughts in order to move forward in the business, especially when you have a high growth business. And that all started at Clorox. There was, I don't think, I don't even know if they do it anymore. It was brilliant training. It was brilliant.
A
You know, this is definitely an aside, but I know you'll have an opinion on this. Have you thought of the repercussions of everybody? You know, I just mentioned when we first kicked this off about how I think people jump into entrepreneurship and they don't take the training seriously. And I think that's already a mistake. But that compounded with the fact that now with AI tools, we outsource our thinking and we outsource our writing. What do you think is going to happen in 30 years from now?
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Well, all right, so here's the problem.
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I have opinions about this because I find myself getting dumber when I use ChatGPT to write for me as opposed to me writing myself once or twice or three times a week.
B
So there's multiple ways to look at this. When I thought about it in terms of what's happening now, all right, in terms of entry level jobs already in certain areas, customer service, public relations, marketing, communications in general are being replaced by chatgpt, some form of it, which means that the people on a senior level have to direct that and have to know where you're going. And then you combine that with still many people working remotely and what used to be a platform for learning, meaning that you would write, you know, you get assignments as a junior employee and your boss then critiques it and moves it forward. And you watch how your boss interacts with other people to move your ideas forward or to give feedback that is going to be lost. So I'm worried about this band of younger employees not having the training. So what that means is there's going to have to be really good structured training for them because they aren't going to be able to learn it on the job, number one. Number two, any kind of AI is only going to be as good as the brain's directing it. And if you don't have the rigor in thinking, it's going to lead to a whole new level of mediocrity. And that is ultimately going to consolidate power in those who can think. And that's a little scary. It's going to create lots of opportunities for people who maybe were held back through structure or either societal structure or corporate structure or both. But it also is going to allow it's going to consolidate power. Now it's already, I mean, it's sort of happening anyway when you look at people that understand how to interpret data and move forward are actually moving forward faster than people that are actually cranking the data or showing people the data. But it is scary. I think about it. Same thing in banking. A lot of the banking jobs, the entry level, a lot of these entry level jobs can be done better with AI tools. But then without having an ability to train people up to the next level, people are going to get the displacement is going to be scary. You just realized your business needed to hire someone yesterday. How can you find amazing candidates fast? Easy. Just use Indeed. Stop struggling to get your job posts seen on other job sites with Indeed sponsored Jobs. Your post jumps to the top of the page for your relevant candidates so you can reach the people you want faster. According to Indeed data, sponsored jobs posted directly on indeed have 45% more applications than non sponsored jobs. Don't wait any longer. Speed up your hiring right now with Indeed and listeners of this show will get a $75 sponsored job credit. To get your jobs more visibility at indeed.com podkatz13 just go to indeed.com p o d k a t z 13 right now and support our show by saying you heard about Indeed on this podcast. Terms and conditions apply. Hiring Indeed is all you need. Mmm. Mmm. Ooh, whatcha eating? The new Banana split cookie from AM pm. All freshly baked with real butter with banana, chocolate and strawberry flavors. Ah, that sounds amazing. Can I have a bite?
A
Um, sorry but no.
B
But you can't split the banana split. Not even a little. Not even a crumb. What if no, please mine when it's.
A
Too legit to split. That's cravenience.
B
Get a 3 pack for 99 cents.
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With our app ampm. Too much good stuff plus tax where applicable. Prices and participation may vary. Terms and conditions apply.
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A
So, tell me about. Tell me about. I know at one point in your career, somebody told you you were unemployable.
B
Oh, that was a lot. Was after 20 years. Yeah.
A
Yes. So why. So just, you know, looking back, obviously, that's hilarious. Why at one point in your life were you unemployable? Based on what they said, it was.
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A combination of having a failure. I had one failure. Again, I'm a risk taker. That was pets.com. it was very. So it was a very public failure. I wasn't the founder, but I was the CEO and I took it on in a very early stage of the company's formation and then took it public and then shut it down because I couldn't close the next round and gave money back to shareholders. And it was incredibly public. And people. Then it was like 2000, 2001. So the world was sort of in a slump, I would say. After that, I did other jobs that weren't that compelling. And that person, basically, he didn't say because of your age. But it was also my age, and I had a big failure and I was pretty much unemployable. And he was right, to be honest. I mean, it was like, you know, he was right. And no one. I think no one had been that honest with me before. So that was true. I didn't want to hear it. But that's why I made a decision. I had to start my own company or do something, come up with a radical plan B that was incredibly unattractive to me at the time.
A
Was there? Was there? You know, when you think about how successful you've been now, obviously, and it's true, actually, that you weren't employed. Maybe you are unemployable. Maybe that's a blessing. Maybe it is a blessing when you're unemployable, because almost all entrepreneurs that I speak to, they all say, I could never have a job. I could never have a job I love well.
B
But I had been. I had worked my way up and had been a CEO of a company called Berkeley Systems that the founder wanted to sell and made money off of that. And a company called reel.com, which was the first site to sell movies online and had run that, and the founder that wanted to sell it and that was sold and made money off of that. And so this is my third CEO gig. And it imploded. And after that, it's like, sorry, failure, you're done. And I'm like, and up until then, I'd done pretty well. But, you know, it was like, enough. It didn't matter. It didn't matter. And what's worse, though, it's not even worse. What he said to me, that was honest and true. What was worse is I bought into it, you know, So I bought into this failure mentality. So that was. I had to shake that before I could move forward. But I bought it, man. And so, you know, I ate what the. You know, what the populace was. Was pushing down my throat. I took it. And it's because I felt terrible after that for multiple reasons, but I'm like, you know. And at some point, which is, you know, do you ever see. I know this maybe isn't your favorite movie and it's an older one, but do you ever see Moonstruck?
A
No, I haven't. Tell me.
B
Oh, it's such. Oh, it's such a good movie. You need to see it. But Cher's in it and Nicholas Cage is in it. And at some point, Cher just turns around and slaps her character, turns around and slaps Nicholas Cage on the face and says, get over it. And it's like, I had to do that to myself. I had to slap myself in the face and say, get over it. Come on. Life is for living. Not sitting there, living in the past and in my head about what a failure I was. I literally had to walk myself through all the successes I'd had, and was I really a failure or was it timing? And it's like. And am I going to just live in that space? So I would say my biggest problem was I bought the narrative. Until I didn't, but I did buy it. I bought that narrative.
A
I have to bet on myself and I have to, like, I can't. I'm not done yet. So what is that point? Because, I mean, when you started RealReal, and this is what your whole book is about. So I'll just. Time to Get Real. That's the name of the book. You can get that anywhere. You get books, I think starting June 10th and beyond. Go on Amazon, wherever you want to get it. We'll put some links in the show notes as well. But this is. This is sort of your. This is your story about how you owe you. Career, success, career, success, career, success, career, not so much a success. But then you pick yourself back up and you bet on yourself again. I think There's a lesson in there, because that's not easy after a failure like that. I think a lot of people would have a really hard time saying, I'm gonna trust myself to build something significant. But you did. So how did you do that? What was the mental model that you went through, the exercise?
B
Well, a couple things happened. One is I went inside to a venture capital firm after that dissolved for a while just to help with some of their businesses, which, by the way, none of their businesses really wanted my help. But they're like, well, they wanted me to help them and they believed in me. But their business are like, well, she just failed, so why are we talking to her? But. But then I saw the companies they were investing in and the entrepreneurs they were investing in, and, you know, they were fine. They weren't. And I mean, they're fine, but were they brilliant? Were they any smarter than me? No. All right. In fact, if anything, their lack of experience was going to make them less capable. So seeing what people were rewarding made me take a look at myself. Now, this is going to sound nuts, but I'm going to put it out there because it's true. I grew up in South Bend, Indiana, and if you grew up in Indiana when I did, and I think still now, you really had to love sports, because either that you had to. Notre Dame is there, which is the major university, but Indiana, when I was there, is known for great basketball teams and great football teams, all right. At the college level. So when you look at basketball or you look at baseball, they weren't as much known for baseball. Those guys lose almost more than they win. And they play so many games that if they brought that failure mentality into the next game, they would fail again. And then even something simple. I remember sitting at a Giants game with a friend in San Francisco, and the guy gets. And she was a real stat hedge. Like, I don't. For what end? I don't know. I don't know why she had to write down the stat because, like. But she would write the stats down and, like, she kept all the bat. Like, maybe she's on the spectrum. Who knows? But anyway, she was down there recording the stats, and I thought, you know what? That great batter with a 0.375 batting ratio, who's great, fails 63% of the time. And you're like, okay, I got it. I mean, all this information was coming. And then also, I just got sick of living in a bad state of mind. I'm like, this isn't my personality. I Got sick of myself. I took stock. I looked outside myself, I looked to sports. And I thought, I'm going to do it one more time and give myself. I only had two years worth of capital before I was going to be in trouble, and I mean really bad trouble. But I had a house, so I was gonna. I put that on the market just in case I ran out of money. And I was gonna, like, okay, I. You know what I've had. I'm the oldest of four. My mother was ill almost all my life, and so I've had to figure stuff out on my life. And I'm like, I gotta figure this out. And. And it worked out, but I would say I let it go too long with a negative thought of myself and my success. It also didn't help that when I. When pets failed, I also was. My husband asked me for a divorce the very same day. So it's like, are you serious? Yeah, yeah, yeah, yeah. It was sad. I mean, it was horrible.
A
Was there a reason? Was it. What? That's insane.
B
Well, I mean, was there a reason? I would say the marriage was under stress anyway, but.
A
That'S horrible. That's horrible. Time.
B
Yeah, it was horrible. But later on when he came back, he came back much later to talk about it with me. He said he became fearful. There's that word again. Fear. And felt like all he could do was run away. So me going through my trauma created fear in him and he didn't know how to deal with it. And my trauma of shutting down the company and. And he didn't know how to deal with it, so he decided to run away. And he said, and by the way, he's a therapist by training. And he said it was a horrific thing to see in himself that he never thought he could get over, which to me is ultimately much sadder and harder than me going through it and getting through it. Being stuck in that space where you don't trust yourself to be. To do the right thing when things are tough, that's a. That's a bad trait. Honestly, to not. You have. I mean, yes, friends are important and people you love are important. What they say to you. But at the end of the day, if you don't trust yourself to make the right decision, I don't. I don't know. You can't. No one else can fix that for you.
A
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B
No, I wasn't. So you know what I did? I had been an employee. Yeah. So I think for me the key thing was I knew the world had changed. Now it's 2011 and 2010 and E commerce no longer took. I loved E commerce by the way. Reel.com was one of the first E commerce companies ever. That was the site that sold movies online. Pets.com was also incredibly early. Reel.com had a good outcome. In fact, it's sort of funny. Hollywood. Reel.com sold movies. They sold cassette tapes. Because that's and then they sold DVDs. All right, they were. And we couldn't switch to rental because it was a different. We'd have to build a new type of software. So even though there were rumors that Netflix was forming out there, we couldn't have competed with them because the platforms were so expensive to code then because you had to code everything. There was no plug and play and you had to have servers in a server farm and you had to have warm servers and just huge capital expenditure both on human capital and physical hardware. And there was no cloud. So anyway, what, oh, where was I go with that? So all of that was so exciting though. And it was exciting to create a consumer brand and make it easy to transact. When I decided I was going to do something again, everything had gotten easier. You know, you didn't have to build every line, you didn't have to write every line of code to create a commerce site. The cloud wasn't really going them. But even, even the cost of servers and coming. It wasn't like you needed a $5 million server farm to, you know, to handle 10,000 people. I mean, when I was doing it in those days, you still had a little badge that said you were safe to transact. And half the people wanted to call you on the phone and give you your credit card. Like that's more secure, you know, was that world. And I thought, I love commerce, it's very exciting. I want to get into E commerce. And the only big player really was Amazon. So it's like, okay, I need to map out what Amazon can't and can do. And that was my. And I did a whole matrix. I ran it past a couple bankers and they're like, yeah, we agree. And then I had this beautiful four quadrant thing. Like here's what they're good at, here's what they're not, here's where their holes are, here's where the opportunities. And I had no ideas that mapped to those opportunities. And one of those opportunities was the luxury market. That Amazon would never be able to make a dent in the luxury market. It just wasn't in their DNA. And that's not how luxury markets, luxury market customers shopped. So that was going along. And then I did see a friend in a go. We were shopping. Most people, most women I know have good shopping buddies. And I was shopping with one of my good friends and she, and we were in one of her favorite boutiques that had a little bit of consignment in the back and that's where she spent her money. And she bought brands that weren't normally in that store. She brought Prada, Gucci, Louis Vuitton. And I was shocked because she had a lot of money. She was a venture capitalist. She. I'd never seen her go into a consignment store. She said she never would, and yet she was buying consignment. And I'm like, that's it. That's the luxury market. That's untapped. So then I looked at what ebay was doing. I'm like. And I'm like, they aren't doing it right. They're like, Amazon. They're like Amazon for everything. Not, you know, for previously owned things and size. The luxury market once again. And that was it. As soon as I got it, I ran as fast as I could. The owner of the shop was a former tech person. So I called her to set up a meeting, talk about doing it together, you know, because she was a tech person, she already had sources of product coming in. By the time she called back, I had a name. I had raised a little bit of money. I had my first employee identified who hadn't joined the company yet. And I was on a roll, so. And then she wasn't that interested anyway. She's like, oh, I don't know. And I'm like, no, this is ripe for the Internet. And so then I moved really, really fast because here's the other thing. And maybe you've seen this in your life, but I've seen it time and time again in Silicon Valley when. Which has been most of my. Almost all of my career. When you have a good idea, you can bet on it. Someone else is channeling. It's almost like you're tapping into something bigger than you. Someone else is channeling that idea too. And I mean, just like when pets dot com. There were seven other companies being formed that were in the pet space back in 1998. But it happens time and time again. So right when I was doing that, I'm like, I better execute. I better move and execute fast because somebody else has this idea. Because ideas are great, but they're really nothing if you don't execute. And it's how you execute that can make the difference between an idea moving forward and being a phenomenal success or not. There was one company called Thread Flip that actually raised more money than I did, that came out when I did and raised more money at a better valuation than I was getting. That could have been a real competitor. But the guy did not execute. And I was thrilled. I was just thrilled. Put A lot of money into building the platform, not building the supply and the supply. It's all about supply. So again, what's your high order bet? Right? And honestly, when you're in a competitive race like that, you don't have time to learn that on the job. You have to think that way. You have to think that way from the beginning because if you aren't, somebody else is going to eat your lunch. Let's say you get something out there that is half baked, but it's directionally sound. It's just not on the mark. You don't have that long in a competitive world to get it right on the mark because someone else might be able to do it better and faster. I see it over and over again.
A
What was the activity or the thing that moved the needle the most towards that competitive mark that allowed you to.
B
Oh, it was the structure of the business. So I set it up from the beginning, from the beginning where we were going to do all the work for the consigner we were going to do, we were going to price the goods, not allow people to price. Because my, at the beginning we didn't have this advantage. But I knew very shortly when you have tens of thousands of people and now there's millions of people looking at items, you will know the prices, they will tell you the price. Right? Because it'll sell or won't sell. So, all right, so service. Go to people's homes to pick up the goods. You don't want all goods, you only want luxury goods. So what you pickup is important, number one. Number two, we had to control the pricing because people would never price their things to market. Number three, we weren't going for the best price. We were going for a price within a 90 day window where that item would move. Because I already knew that. I didn't want to keep building all these warehouses to house goods. We were a way station, not a warehouse. So the last thing you wanted were goods piling up and you have to keep renting space because things weren't moving. That means you have a pricing problem. And then the last thing was to have excellent authentication to build trust with the consumer. So all of those things were the premise of the building. Oh, and put a big umbrella across all of that structure. Supply and consignors matter more than consumers. The consumers will follow the supply. It's all about the product you have in. So if you pick up the right product, it'll be so easy to sell it through. And if you pick up the wrong product, it's going to sit there and you've got a big problem. It won't be just a pricing problem, which meant that we weren't going in the overstock mode, because if it didn't sell the first time, it's probably not going to sell easily the second time. So all of those things were the premises of the building a business. And it came to me very quick. Now look, I have been working for years, so I already knew I didn't want to build up inventory. I didn't knew I didn't want a big warehouse. I already understood the consumer dynamics and the consigner dynamics. And I already talked a little at the beginning that Clorox trained me on how to focus on the high order bid. So I knew it was all about supply and getting the best supply in and the consumers would follow. Thread Flip Guy, I think, raised their second round and went out of business. Then after that and the real, real it was never easy to raise money, but I mean the business just went 10 million, 25 million, 50 million, 100 million, 250 million, 500 million, 750, a billion. I mean we just kept growing, growing, growing and raising capital to support it. And it really was getting it set up. So at that time, Thread Flip was gone, which could have been a real competitor. They had a hybrid model you can post or we'll pick up, but they never really. It was too messy. They couldn't figure it out. I don't know what went wrong. From my perspective as an outside viewer, it looked like the CEO was focused on building a great platform, not getting the right product in.
A
Everything about product, everything about product, it's.
B
All about your product always. Then there was Thredup, who was the low end doing everything we were for like $39 sale, which didn't make sense to me and was. And I figured at some point they're going to want to say they're going to move up. But I knew they couldn't. If you start low, you can't go high. If you start high, sometimes you can go low, but you better be careful. But you can definitely not go high if you start low. So I knew that was going to fail. And then there was a couple other sort of weird ones that people like. They did. One with the tagline was everyone wants their wants to be a star in their closet to be a star. And it's like nobody, none of the people that we dealt with wanted people to know they were consigning and they didn't want to. But it was an influencer model. And I remember meeting with one of VCs, like, no, this woman's brilliant and this is her model. And look, she's already at like 3 million. I'm like, oh my God. So I met with her. I'm like, this won't work. But they were convinced that it was the me generation that would work. And then there were others that came and went. But the truth is, by the time they were going, we already had a huge moat around the business that actually got better and better because as the company matured, machine learning and already AI, which is not new, but using our own installed base, we're getting more efficient on identifying products and putting product right through the right swing lane and authenticating it and doing other things in the op centers to make it more and more efficient. But honestly, it's all about the choices you make. And it's hard when you raise VC money because venture capitalists are a unique group of people. They see a lot. They're great at early stage businesses, better than anyone else. You should never have a PE guy on your board when you're, when you're growing like that because they don't know. They know how taking value out not. We have one exception, a guy named Mike Cuman from Great Hill who's brilliant. But other PE people are kind of nightmares. And they, they, they understand value abstraction, net value creation. But VC people are really, really good at what they know. But I would say in this case, my vision was so clear that they would say, oh, try this. I'd be like, no. And so I would shut them down, which kind of pissed them off.
A
That conviction is what it takes. Sometimes you need that.
B
Well, I know, but you know, they're also used to being the smartest people in the room. And so that, you know, I could piss them off. But at the end of the day, the early investors weren't really pissed off that much. Cause I went public and they got their money out. But, you know, it was so clear. It was the weirdest thing, Scott. I saw that business. I, I saw all the ways we needed to compete. I saw really what was. In a flash. I went home after that meeting, after that shopping meeting, even though it was a pure shopping experience, I wrote the whole plan out, the whole structure. And it was like I was. And it was. And I just knew it was going to work. Even though it was always hard. It was always, always hard. I'm like, nope, it's going to work. I never wavered. Now that didn't mean that I Didn't have to take in new information. But you know, venture capitalists say more no's than they say yeses for a reason. And I got so many no's and so many people saying oh no. And I'm like, oh, this is gonna work, don't worry, come back. I'm like, don't worry, it's gonna work. I'm gonna figure it out. It's gonna work. So many. But all entrepreneurs have obstacles, of course.
A
But they also have an incredible amount of self belief. I think that is the X factor.
B
I know it is, it is, but it's also, it could be, it could be crazy thinking too. It could be a name. You have to know. It's. It's a hard line, you know, because I do think. I love entrepreneurs, but I think we're kind of flawed people. But which in a good way. But I love them. I love their conviction, I love their rigor. The really good ones are really rigorous thinkers. I love their bravado, I love their bullshit. You know, all those things that are really important, you know. But they could be delusional too. I'm sure you've met. I met them, I met a lot of them recently.
A
I have.
B
I've met a lot of them recently.
A
I have. But, but at the same time, that delusion, listen, it will be misguided for a period of time, but if they stick with that delusion long enough, eventually they'll figure it out. Not delusion. And not delusion in the sense like, like, you know, like, like a Sam Bankman fried in ftx or like an Elizabeth Holmes in Theranos. Not that kind of delusion. Delusion in the sense that you are building something ethically and you're building something real, but the dream and the vision is so audacious that only you can see it and everyone else thinks you're nuts.
B
That's what I, I know, but it's a hard, it's a fine line. So you know, you know, I'm sure Elizabeth Holmes board members thought, well, we know from what we have, anyway, if you've read the story and you believe the story, they believed her for a long, long time. But you know, when I and I didn't know him by any means, but I was around him at different conferences and I and some of my friends knew him very, very well. Steve Jobs really believed he could bend reality. And you know what? He did?
A
He did. I love that. The reality distortion field. I everything about that I fully believe. Andreessa Mike and he speaks about the World being very malleable, being able to bend to your will. And I believe that.
B
Well, I think, yes. And I think that's where evil can come in. You have to be careful about. But I agree with that. I mean we're seeing it sort of what's going on right now in politics. I mean things are happening that we never thought was possible and that wouldn't have happened without a person that strong willed and what they're doing. But I do, let's just take that from on business side though. If you think about it and you see it all the time and I saw it even with a friend of mine who had a co director on a project and I'm like, you can't have a co director because you don't have the same vision. If you don't have a clean vision and if you don't know where you're going, other people will come in and influence you on where you're going. Absolutely where you're going. And you need that vision for a company, for a movie, for a play, for anything you're writing. If you don't know, if you don't have a point of view, you will fail. You will absolutely fail. And let's, you know, we were talking about people that are impacted by social media. It's the same thing if you're just following other people's point of view and being like, oh, I'll try this because this influencer, I, this it's like you're just going to be like you don't know yourself. If you don't know yourself and what you're working on and what your values are, you're at some point that structure, you don't have a structure to build on. It's so important to know yourself, know your values, know what you're building, know why you're building it and to have that clear vision, it is so important. I don't care what project it is. And that is, that's the other thing. I mean I did not have a co founder when I did the RealReal and honestly I think it made it easier, maybe harder because I was a woman, a woman trying to raise capital and women only get about 2% of funding. And I was also a woman who started a business at the age of 52 so that was almost unheard of. But I mean I did it so that means other people can do it. I, but I think my vision was so clear that if I would have tried. And you always think about this. I mean, let's just put it this way, maybe you don't. Women always think about, do I need a male co founder to raise money? Because the stats go in your favor. It goes up from 2% funding to maybe, if you have a male Co founder, 15%. So your success rate goes up in normal. If you have a male co founder and I thought about it and I thought, you know what, I can't because it would be in name only. And you give someone the title co founder, at some point they're gonna think they are the co founder and they're gonna have to have equal shares and you're gonna be doing all the work and it's gonna fall apart. But I thought about it, I thought it might make funding easier. And for a while, women were. Women's groups were going around telling women that, you know, it's a lot easier if you have a male by your side when you're out raising money. And don't be surprised if all the questions are directed toward the man and not you. And don't take it personally.
A
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B
So it really comes down to putting processes in place that are scalable. And in order to do that you have to break them down into smaller pieces and make sure that you can automate as much as possible. But it really becomes drives the scalability and it also in a weird way drives the innovation at some level because you know, humans I haven't seen and obviously that isn't necessarily true because you know, you have McDonald's franchises, they're multi daily, that are all powered by humans. But when you think about what we were trying to do, it had to be and there's still, I think even now there's about 3,000 employees at the RealReal. But you needed processes to drive the scaling and that had to be technology driven with human oversight for the processes, otherwise it could never have scaled. And then it became tricky because here's the interesting thing, when you do something that's never been done before is you need people that have experience, but those people have to think differently. And there's very few people I've met in my life that have deep experience in one area and you move them over to a high growth technology business that still needs that experience but needs them to think differently. And it's hard for them to make that shift in thinking because what they know and what they've, especially when you get into ops centers and operations centers, what they're skilled in, let's say it's 70% transferable and they can make a big difference. But the 30% is where you're going to get innovation and probably further scalability. And that's a creative problem solving mindset that isn't necessarily found in people who came from organizations that didn't require that. And so that's where it becomes. Once you get to that certain size, you want people that are good thinkers. They're still scrappy, they're creative problem solvers, but they have to have. You don't want them learning how to run an op center on your dollar. You want them to know how to run it, but still have these other skill sets. And that's where it becomes tricky, finding people that are sort of extraordinary thinkers in their field that also still want to join an organization that they can make a big impact on but isn't maybe in their mind secure. So that's the tricky bit. The people become. You always have to have the processes set up to scale and it's broken down into smaller bits that can be further scaled. And you need to know what can scale in the future too. So here's where we are now, here's what we can do later and build toward that. But then the humans driving that are the trickiest part because there aren't that many people that have 20 years of experience that are still great creative problem solvers because they haven't had to be. Or if they're in a company for a long time in order for them to succeed, they developed other skill sets. And those skill sets are more political in nature than job in nature. And that political skill set doesn't work in a fast growth business. It requires. And what I mean, you know, because if you're in a lower growth business but you're still ambitious, you don't. You get ahead by doing your job, but you get ahead on who you know and how you network and who you suck up and who you suck up to. How good you look up, maybe not how good you're doing down. And you see it time and time again. People become the hardest challenge always at that point. And you know, you see it in a lot of turnover. I used to have big debates with my board and they'd be like, well, what that company does should. I'm like, look, we're in the, we're solving hard problems. I'll give you an example. I had a board member who was an investor. The company was also an investor in another E commerce company that was big, slightly ahead of us in size and doing very well though. And they were having the same challenges we were with having ops people run it, getting a new great. I said, well they're having, I'm talking to them, they're having the same problem. He goes, well, that doesn't mean you can't solve it. No I'm just saying it's a hard problem to solve. So when you get to that, because you know, you're not coming into a steady state business, you know, you're coming into a dynamic business now. All business. You know, every business I met people like, I'm an. How do they call them anyway? There's a word corporate people use to say they're an entrepreneur in their business. And you know what? 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A
You know, you are. So I learned this. You are one of 23 women in history that did the company public as the founder CEO, which is incredible. Congratulations. It's phenomenal.
B
Wait, there's been more now I think there's been eight more after me. But thank you. But not a lot. Not a lot.
A
So we are still under 40. Just to be safe, we're under 40 in history, right? So I just want you to tell that I want you to tell sort of as like a last story. Think it's an incredible story. I want you to. I'll tell you what. I think the audience would appreciate if you could unpack. First, the importance of planning the exit. When you first start building the company, what do you think about then? And then secondly, how do you actually execute? How did you actually execute? How did you decide when it was time to go public? How did you. How did you navigate that process? And then why did you personally leave after the company was public? So that.
B
Okay, well, that's a lot. All right, let's start.
A
All right, I know that. I know. Listen, I know that that could be a whole hour. But.
B
But let's just start. Why? When you take people's money, you have to give them an exit number one. Number two, the real world had no natural buyer. All right? So that meant we had to ipo. There was no natural buyer for the company. All right? So that was already my. When we decided to get ready, I knew my magic number for going public was we had to be getting toward a billion dollars in top line revenue. You have to discount that quite a bit because you only report. You report that number, but you report 35% of it. And the business had to be repeatable and predictable. Both things had to be true. It was looking really good. Around 500 million. All right. @ that time, I also knew that men would never get our business. They didn't. They never got it. Wall street wouldn't get it. Most of investors are men. You'd have to go on the Roadshow, most bankers are men, although there are exceptions. But, you know, so what does that mean? We're going to have to show what that business is. That was the impetus behind the first store in soho. First we ran a pop up to see what we didn't know and see if it was a good idea. Once we gleaned information from that pop up again in soho, soho's close to the financial district. We figured people could experience the realreal and the value of the product. The products were so good in the op centers. We wanted to bring that forward for consumers to experience it, to enhance the brand. But we also wanted bankers to see what happens in a store. Cause then it would be undeniable. New York City was important by the financial part of New York City was also important, hence the store in soho. Then it was talking to the board, getting agreement on what the triggers would be. And then, I mean the markets can be very volatile. So also being keenly aware of other things going on and everyone sort of just like now was worried that Trump would do a tweet, closed the window. Now it's sort of, you know, now it's created his own chaos and churn. The other thing bankers were worried about was wework. And, and first of all, the, when I took the company public, we were still losing money, but we had a plan to get to profitability and the business was highly predictable. Put Covid aside. Covid wasn't even in our headset that that was going to put a big dink change in everything. But we are going to do that. And so then it became, well, wework is losing so much money and companies that aren't profitable are going to lose complete credibility if they go public. So you've got to get out ahead of the curve of them. And everyone was really worried about that because they were losing so much money and they just thought they could actually close the win. All you need is one company that can't get out or gets out and then really fails either of those things happening and the window will shut. It's very volatile. It's very hard for companies that aren't profitable. So we said, okay, all right. So then we rushed to go out. Now what I wish we would have done, which we didn't do, and I went back to the. And then everyone, the board, then you go through the process. But what I wanted to do and the board was against me and I still think I was right and I should have pushed harder. I really, even though I'd taken a company public before, it was a long time ago and the world had changed. So I would say I was a relatively inexperienced CEO for a public company. We had a CFO that had never taken a company public and he hired an investor relations guy that had never done it either. So I wanted a new CFO and a better IR person. And they're like, no, because he's been. And you know, we don't have time for that. They didn't even disagree that I needed someone more qualified. They just said we don't have time to bring someone up to speed. The business is not intuitive. And that wasn't. I, I should have, I knew that a long time ago that I probably should have made that move and I didn't. And it did cause some problems in the on the path to profit and path to going public anyway. Then we go public and I mean I'm not going to go into what happened with in the book but a lot of drama ensued with weird stuff happening with the company. Could have been Chanel, could have been anyone but like police invading our luxury consignment office. All this stuff like boom, boom, boom. All right, so reported the first quarter better than expected. And by the way, here's how it works. This is always good because I always hear people say, oh, they beat their first quarter. Well of course you beat your first quarter because first of all every analyst sees your first quarter numbers and all the assumptions before you go public. So you're not gonna blow that. Otherwise you don't know what you're doing. You're gonna make sure they're conservative, but not so conservative you look like you're low balling and your business better be predictable. Anyway, so we hit anyway we hit our first quarter. That was good. We're gonna have. We ended the year well. But the stock was floating all around cause of a lot of interaction that a lot of shenanigans going on behind the scenes that that were perpetrated by others outside of our control which are in the book. A lot of shenanigans. And anyway, which I enjoyed writing about because I did get to name names then we're all excited going into 2020 and the business is up 40% versus year ago. And then Covid hits complete shutdown, the business goes down 40 points. And the real real is a company that went to your house and picked up things we are not. That company is not a self posting site. And guess what? Could not pick up anything at all. And again I think I explained, I don't know, we talked ahead of time. But we had optimal pricing for optimal product movement. So you didn't build up tons of inventory. So most 90% of all product moved in the first 90 days, which meant that when demand picked back up, which it did, oddly enough, for shoes, jewelry and handbags, which is kind of nuts on the shoe side, and a little bit of clothes. But it picked back up about six weeks into Covid. But we couldn't pick up product. So all of a sudden you've got product selling through and no product coming in. So it created. Anyway, it's a longer story. I could go on and on about that, how we solved it anyway then. So we've come out of COVID got a new CFO I'm thrilled about, by the way. I love this guy. And he comes on and he's like, things are looking up. So I think we did a billion. Like a billion and something in 2019. We went over a billion dollars. We shrunk. We ended 2020 like 965 million top line. But we were back on top by 2021. We're feeling like, okay, management change. It was sort of a mess with my team. And my CTO was from Sweden, wanted to go back to Sweden during it. And it was a kind of a nightmare. The former CFO who was going to be let go, tried to get a coup against me. It was a nightmare before it was going to be like that.
A
This is entrepreneurship.
B
It was a nightmare. So then I. But listen, I had the last investor in the company, never got off the board. I had a whole new board because they had gotten off once we went public to sell their stock. So I had a whole new board made a big mistake on recommending those board members because I didn't consider values. I consider. And I have to tell you, here's the fascinating thing about this. This is going to sound sexist, but I think it's true. And someone told me this way too late. Women tend to hire board members that they believe will benefit the company in their area. They need help or their area. They could actually an expertise. Men tend to hire board members that support them and will give them the vote and take care of them. All right? So when I give advice now, I go, think like a man, not dead. Because they're like. I think. I go, no, just get board members on this. Support you. You know what you're doing. Screw the other things. I didn't do that. But I didn't hire. I didn't. You don't hire. I didn't recommend board members that had a Shared value with the company values or my value. And I had one guy, last guy in, who was the PE Guy who didn't get his money out. So I get the new CFO in, and he's like. And he was great. Name was Robert. Robert's like, julie, something's going on. I think that guy's out to get you. I'm telling you, something's going on. There's a troika. There's a troika. And I'm thinking, the guy's paranoid. I don't know him that well. I'm like, oh, man. And I never think like that, like, someone's out to get me. So I'm thinking, oh, my God, he must be real. And I'm. But he's getting in my head. He's talking about it. He's like, no, no, no. Because, you know, he's out selling the new budget, and I wasn't in all of this. He goes, something's going on. And he wasn't paranoid. He was astute. So my theory is. So the net of it is I got fired. I was told I was fired because I didn't hit my numbers during COVID I did tell the one PE guy who I'm sure was out to get me that led a campaign against me, but I have no proof. But I. You know. You know. You know when you know. Even though I have no proof, I better. No proof. I did tell him to f off in a board meeting because he was lying, which caused the other people in the board going, you can't talk to a board member like that. I go, well, I can when he's lying. And that didn't go over well. And let's just say it didn't go over well.
A
Oh, my goodness.
B
So it ended up being. I don't have a political bone in my body, and honestly, I was just working my butt off to keep the company, keep the wheels on. The guy who I thought was paranoid was astute. He ended up leaving a year later, and according to him, did something similar to what I did because he didn't believe in the new CEO and told him off. I don't know if he did or not. I wasn't there. The new guy they brought on had never been a CEO before, had worked with a former board member, was unemployed. And anyway, he was fired. And the person who was my heir apparent, who I would have loved to have helped her move forward, they promoted to CEO in October, and the company's in good hands. But here's the interesting thing. About the real, real. If I left a company that had tremendous potential, a great competitive moat that had a path to profitability, and the only thing that could have ruined it was bad management. And it looked like that was what was going to happen, but now the wheels are back on.
A
Good. So there is a good ending to this story, even if it was a stressful. You don't do easy. You do not do easy stuff. You do not do easy stuff. And nothing has. Nothing has come easy. But at the end of the day, it's all worked out.
B
You know what? That I should put that when I'm looking back, I don't do easy things. And it has all worked out. And here's the other thing is like a more political person would have played the game and really done it. And I've thought about that because getting fired from your own company was horrible. And I thought, you know what? I can't. I still, I couldn't because I know what I said was honest and I can't, you know, and people that were in the room with me said if it would have been a man, men in the room with me on my team when that happened, said if it was a man, no one would have reacted that way. But the truth is I was always about making the company great. And I thought there were competing interests in the room based on that guy not getting his money out. And it could have gone that way. But luckily then, luckily it all worked out, Scott. It all worked out.
A
Where can people connect with you? Where can people get your book? Your story is fascinating. I mean, in all seriousness, we could probably talk for another three hours and just like, you know, just, just start to unpack all the crazy shit that you've gone through over your career. But there's so many lessons, there's so much wisdom. So I really want people to, to get an opportunity to read through the story, to sort of consume more of your content. So where do you want to send them?
B
So it really. Amazon or Barnes and Noble time to get real audio version. If you hate my voice, don't download it. I audition to read my own voice and to do my own story. And I won my audition. That's funny too, because Amazon's audio company picked up the rights for the audio version and I had to audition and they basically said, she'll do, but we think an actor would be better. So. And they might have been right. But I read it. So if you don't like my voice, buy the real book.
A
You have a fine book reading voice. You're Good.
B
Oh. Anyway, I had a great director. The audio version will be ready. I also am helping entrepreneurs with two other women called the Armchair Entrepreneurs. We're starting a podcast. We're trying to get at least 10 of them in the can that we feel good about before we release it. But the Armchair Entrepreneurs, where we're helping entrepreneurs, there's three of us. I'm in the tech person. There's a fashion person, and a packaged goods person. So it's sort of fun. And I'm on. I'm on LinkedIn. But you're right. So now when I look back, I'm gonna say, I don't do anything easy.
A
You don't.
B
But it. But it all works out. But it all works out if you wanted to.
A
First of all, good luck on the podcast. I'm excited to watch it. You're gonna be a lot of fun. You're gonna be an excellent podcaster, just because you have so many stories and so much experience, but you're a fun person to chat with. So I think it's gonna go very, very well. I will be a subscriber. I'll be a listener, because I'll learn. But outside of that, I want you to. You know, you've given over a lot of wisdom based on just your career, some great stories, and I hope that people in the audience that are listening, that are entrepreneurs, woman entrepreneurs, founders, people that are just highly ambitious, can sort of learn from a lot of the things that you've gone through so that, you know, they can emulate some of your success, but also, hopefully not go through as much tough stuff as you.
B
Did, because, honestly, you know, it's. I'm so glad I'm still learning, but it's not easy.
A
It's not easy. Last question. I ask everyone the same question. You know, you've had an incredible career. You've taught a lot already. If you wanted to leave the audience with some words of wisdom. And I always frame it from the perspective of if you could only pass on one piece of advice to your kids, but just think about the most important piece of advice that you've learned over your life. Be it for business, for entrepreneurship, for just life in general, what would that piece of advice be and why?
B
Operating out of fear is always losing. It's always losing. So I'd say whatever you can do to understand yourself, to understand why you're not doing something or why you're doing it, and if you're doing it because you're afraid of something, it will never work. Even if it looks like it's going to work. It will never work and that's good advice for every part of your relationship. You have to go forward trusting yourself and trusting the process because fear based decisions have failure written all over them.
A
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Podcast Summary: Success Story with Scott D. Clary
Episode: Julie Wainwright - The RealReal Founder | How She Rebuilt After Pets.com Failed and Built a Billion-Dollar Empire
Release Date: August 8, 2025
In this compelling episode of the Success Story Podcast, host Scott D. Clary delves deep into the entrepreneurial journey of Julie Wainwright, the visionary founder of The RealReal. The conversation navigates through Julie's early successes, her public failure with Pets.com, and her triumphant rise to building a billion-dollar luxury resale empire.
Julie begins by reflecting on the foundational experiences that shaped her career.
Julie Wainwright [03:37]:
"I've always wanted to understand how business operates from multi functions. I loved technology from an early age and was willing to take risks in companies that were incredibly nascent."
Her tenure at the Clorox Company provided her with rigorous training in brand management, instilling an analytical lens that would prove invaluable in her later ventures.
Julie Wainwright [04:55]:
"They trained you to write like that, and what I didn't realize until I left was they were training my thinking. They were giving me a lens, an analytical lens for everything I did."
Scott emphasizes the importance of Julie's structured thinking and analytical skills, underscoring how crucial training and disciplined thought processes are for sustained success.
Julie candidly shares her experiences surrounding the collapse of Pets.com, a high-profile venture during the dot-com bubble.
Julie Wainwright [15:04]:
"It was a very public failure. I wasn't the founder, but I was the CEO and I took it on in a very early stage of the company's formation and then took it public and then shut it down because I couldn't close the next round and gave money back to shareholders."
This failure not only impacted her professionally but also personally, leading to her husband's divorce. However, Julie emphasizes the pivotal moment of self-realization that propelled her to rebuild.
Julie Wainwright [18:04]:
"I had to slap myself in the face and say, get over it. Come on. Life is for living. Not sitting there, living in the past and in my head about what a failure I was."
Undeterred by past setbacks, Julie embarked on creating The RealReal, identifying a niche in the luxury resale market that Amazon couldn’t effectively penetrate.
Julie Wainwright [26:47]:
"I needed to map out what Amazon can't and can do. One of those opportunities was the luxury market. Then I moved really, really fast."
Her strategic approach focused on supply over demand, ensuring that The RealReal curated high-quality luxury items, authenticated them meticulously, and maintained optimal pricing to facilitate quick turnover.
Julie Wainwright [33:33]:
"Supply and consignors matter more than consumers. The consumers will follow the supply."
This methodology not only differentiated The RealReal from competitors like ThreadFlip and Thredup but also established a robust foundation for scalable growth.
Julie discusses the complexities of scaling a business to a billion-dollar valuation, emphasizing the importance of scalable processes and innovative thinking.
Julie Wainwright [48:25]:
"It really comes down to putting processes in place that are scalable. In order to do that, you have to break them down into smaller pieces and make sure that you can automate as much as possible."
She highlights the challenge of finding and retaining creative problem solvers who can drive innovation within a high-growth environment.
Julie Wainwright [40:44]:
"The really good ones are really rigorous thinkers. I love their bravado, I love their bullshit. But they could be delusional too."
Julie also touches upon the delicate balance between maintaining strong leadership and navigating corporate politics, especially when steering a company through rapid expansion and external challenges like the COVID-19 pandemic.
A significant portion of the discussion revolves around Julie's strategic decision to take The RealReal public, detailing the meticulous planning and execution required.
Julie Wainwright [57:23]:
"When you take people's money, you have to give them an exit number one. Number two, the real world had no natural buyer. So that meant we had to IPO."
Julie outlines the criteria she set for the IPO, including reaching a billion dollars in top-line revenue and ensuring the business was repeatable and predictable. She candidly shares the internal challenges and boardroom dynamics that ensued post-IPO, ultimately leading to her departure from the company.
Julie Wainwright [67:32]:
"I got fired. I was told I was fired because I didn't hit my numbers during COVID."
Despite the tumultuous exit, Julie reflects on the enduring potential of The RealReal and the importance of aligning board members with company values to safeguard against mismanagement.
As the conversation winds down, Julie imparts profound advice drawn from her experiences:
Julie Wainwright [73:01]:
"Operating out of fear is always losing. It's always losing. So I'd say whatever you can do to understand yourself, to understand why you're not doing something or why you're doing it, and if you're doing it because you're afraid of something, it will never work."
Scott acknowledges the depth of Julie's insights, encouraging listeners—especially entrepreneurs and women in business—to learn from her journey to navigate their own challenges successfully.
Scott D. Clary [72:31]:
"It's not easy. Nothing has come easy. But at the end of the day, it's all worked out."
Listeners are encouraged to explore Julie's journey further through her book, "Time to Get Real", available on Amazon and Barnes & Noble. Additionally, Julie is expanding her influence by co-hosting The Armchair Entrepreneurs podcast with other female entrepreneurs, aiming to inspire and support the next generation of business leaders.
Julie Wainwright [70:27]:
"She bought the real book."
Key Takeaways:
This episode offers a treasure trove of insights for entrepreneurs, highlighting the importance of resilience, strategic thinking, and unwavering self-belief in the face of adversity. Julie Wainwright's story is a testament to the power of vision and the relentless pursuit of success.