Turning Ideas into Billion Dollar Businesses (with Julie Wainwright)

Summary

Podcast Summary: The Stacking Benjamins Show – "Turning Ideas into Billion Dollar Businesses" with Julie Wainwright

Release Date: July 2, 2025

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Introduction

In the episode titled "Turning Ideas into Billion Dollar Businesses," hosts Joe Saul-Sehy and OG welcome Julie Wainwright, the founder of The RealReal, a pioneering luxury consignment store. Recognized by Forbes, CNBC, and Fast Company, Julie shares her entrepreneurial journey, insights on building a billion-dollar business, and the lessons learned from her ventures, including the infamous pets.com.

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Julie Wainwright’s Entrepreneurial Journey

Early Career and Education

Julie Wainwright's path to entrepreneurship wasn't a straight line. Born in Kalamazoo and raised in South Bend and Mishawaka, Indiana, Julie ventured into the workforce early. She recalls working at a UAW plant fabricating Monte Carlo rear bumpers, where she honed her problem-solving skills amidst innovative yet challenging conditions.

“I learned so much because the plant was under pretty innovative...reconfiguring everything with technology and it wasn't going well.” [16:03]

After a stint at John Deere as a farm-out buyer, Julie joined Clorox, where her potential was recognized by a consumer psychology professor, leading to her hiring at the company.

Transition to Entrepreneurship

At 25, Julie made a bold move by leaving Clorox to join a nascent personal computer software company—a decision that would lay the groundwork for her entrepreneurial spirit. This experience taught her the importance of betting on oneself and navigating the uncertainties of startup life.

“I knew this is the future and I want to be part of it.” [22:16]

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Building The RealReal

Redefining the Consignment Model

Julie founded The RealReal to transform the perception of consignment stores from being smelly and sketchy to upscale, transparent, and luxurious. Her strategy focused on:

1. Maintaining Brand Integrity: Ensuring that pre-owned luxury items retained their allure and prestige.
2. Consumer Experience: Creating a beautiful environment with gemologists evaluating items transparently.
3. Visual Transformation: Showcasing pre-owned items on models and through high-quality editorial content to emphasize their beauty and relevance.

“Don't break the romance of the brand...respect both the product and the person selling it.” [35:06]

Strategic Partnerships

Early partnerships with high-end retailers like Saks and Neiman Marcus provided The RealReal with crucial exposure. Although certain partnerships, such as with Chanel, posed challenges due to Chanel's apprehension towards the secondary market, these collaborations were instrumental in establishing credibility and market presence.

“Having that initial relationship for nine months...helped people understand what we were doing.” [39:16]

Later, partnerships with global luxury brands like Stella McCartney underscored the company's commitment to sustainability and the circular economy, further elevating its industry standing.

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Overcoming Entrepreneurial Challenges

Navigating Market Turbulence

Julie candidly discusses her experience with pets.com, highlighting the volatility of the dot-com era. Despite early funding from prominent investors like Amazon, pets.com succumbed to the market's downturn, underscoring the importance of timing and financial strategy in startups.

“We had to raise money, cut costs, lay off employees...turning point was realizing we couldn’t navigate the financing drought.” [30:07]

Personal Resilience and Learning from Failure

The shutdown of pets.com was a pivotal moment for Julie, leading to personal and professional introspection. She emphasizes the significance of shedding public perceptions of failure and focusing on moving forward.

“I took on this cloak of failure until I didn't...I need to stop wearing other people's expectations.” [32:30]

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Lessons on Entrepreneurship and Business Strategy

Risk Management and Control

Julie distinguishes between embracing risk and seeking control. While her upbringing around motorcycles instilled a comfort with taking calculated risks, she acknowledges that many entrepreneurs strive to control outcomes to mitigate uncertainties.

“Betting on yourself is easier than cleaning up somebody else's mess.” [11:49]

The Importance of Diversification

Drawing parallels from investment strategies, Julie underscores the necessity of diversification to mitigate risks, a lesson she connects to her business experiences. This principle not only applies to financial portfolios but also to business growth and scaling.

“Don’t break the romance of the brand and respect both the product and the person selling it.” [37:41]

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Investment Insights and Diversification

Case Studies on Diversification

Julie and the hosts delve into the significance of diversification in investment portfolios, using examples like Nvidia and VF Corp. They discuss how concentrated investments can lead to substantial gains but also pose significant risks, as demonstrated by the contrasting fortunes of different foundations tied to these companies.

“Lack of diversification just creates greater standard deviation.” [60:47]

Balancing Passion and Prudence

The conversation highlights the delicate balance between investing in what one is passionate about and adhering to prudent diversification strategies to ensure long-term financial stability.

“Owning stock in the companies is the way to go... it's a concentrated but active investment.” [52:01]

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Conclusion and Key Takeaways

Julie Wainwright's journey from a determined young professional to the founder of a billion-dollar luxury consignment empire offers invaluable lessons in resilience, strategic partnerships, and the importance of maintaining brand integrity. Her experiences underscore the critical balance between innovation and risk management, providing aspiring entrepreneurs with a roadmap to navigate the complex landscape of building a successful business.

“If you can do it, you can do it. If you have a good idea, you will.” [15:38]

Julie’s story is a testament to the power of perseverance, strategic thinking, and the unwavering belief in one’s vision.

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Notable Quotes with Timestamps:

• “I learned so much because the plant was under pretty innovative...reconfiguring everything with technology and it wasn't going well.” [16:03]
• “Don't break the romance of the brand...respect both the product and the person selling it.” [35:06]
• “Betting on yourself is easier than cleaning up somebody else's mess.” [11:49]
• “I took on this cloak of failure until I didn't...I need to stop wearing other people's expectations.” [32:30]
• “If you can do it, you can do it. If you have a good idea, you will.” [15:38]

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This episode offers a deep dive into the intricacies of scaling a business, leveraging strategic partnerships, and the emotional resilience required to overcome entrepreneurial setbacks. Julie Wainwright’s insights provide listeners with both inspiration and practical advice for turning innovative ideas into prosperous ventures.

Transcript

[Joe Saul-Sehy]

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[Doug]

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[Sherman]

Hello there, Peabody here. And this is the Wayback Machine. We're traveling through time.

[Joe Saul-Sehy]

And this is my boy, Sherman.

[Sherman]

Speak, Sherman.

[JJ]

Hello.

[Sherman]

Good boy. Live from Joe's mom's basement, it's the Stacking Benjamin Show.

[Julie Wainwright]

Foreign.

[Sherman]

Doug and how do you take a good idea and turn it into a billion dollar business? We'll tell you how because we'll ask today's guest, the founder of the real, real Julie Wainwright. Plus, in our headline, do you have too much in that one stock? You sure do. And so do some people way smarter than you. Well, I mean, I mean, don't get me wrong, we still think you're really, really smart.

[Joe Saul-Sehy]

Smart.

[Sherman]

And don't worry, we'll help you find a way out. And don't even ask. Yes, it's already on the menu. You're about to win a helping of my incredible trivia. And now, two guys who believe your financial future is brighter than your phone screen at 2:00am Seriously, turn it off. It's Joe and. Oh, JJ Juja G.

[Joe Saul-Sehy]

Hey there, Stackers. Super happy you're here with us today. Sit back and relax because you are in for for some Wednesday goodness or whatever day you happen to be listening. Because if you've ever had an idea, you want to make sure that that idea becomes much, much, much, much bigger than you ever imagined. Well, as Doug so eloquently said, Julie Wainwright joining us today. Mr. OG how are you? You're joining us today as usual.

[JJ]

Yes, I'm contractually obligated to join you today, but I want to be here. I'M I'm here because I want to be here. Also because of the contract.

[Joe Saul-Sehy]

Have you ever had one of those million dollar ideas where you're like, man could have done that?

[JJ]

So many soap on a rope, the Internet, adding guacamole, so many ideas.

[Joe Saul-Sehy]

So, so, so little time. Julie Wainwright is going to talk about that and all the frustrations she had, all the roadblocks that are in her way and how she got through those. So a fantastic episode. If you like kind of built this stuff. The real real, if you're not familiar with the real real, it's a luxury goods consignment store. Not only did she found a fantastic business, she's been featured in Forbes CNBC Entrepreneur, Fast company, Business of fashion. She's been recognized on Forbes 50 over 50 lists alongside people like Shonda Rhymes. Shonda Rhymes, by the way, that woman creates just shows and more shows and more shows. She's a disruptor in luxury, tech and sustainability. She's here, coming down to mom's basement. Sweet, super excited that we get to talk to her. But to have great people like Julie, we need to keep on keeping on. And that means we got a couple sponsors that make sure that you don't pay a dime for our wonderful Wednesday mentors like Julie. So sit back here for a couple seconds. We're going to hear from them. And then we have Julie Wainwright coming down to the basement. Well, as you know, Stackers, we talk a lot about finding careers and finding work that you love. I think that's the basis of a great time on this earth. To me it's way, way, way better than just figuring out how can I just check out and do nothing. And science actually backs that. So if you're feeling stuck in your career and worried that your team can tell, well, jumpstart your growth with ido you. Their online courses draw from design and innovative company IDO's award winning methods and you can dive in whenever you're ready. There's never a bad time to transform your professional life. If you've ever felt overwhelmed by all that AI hype that we've talked about here on the show, you know it's important, but you're struggling with how to use it in your day to day work. Well, IDO use AI and design thinking programs are designed for leaders like you. People want to stay ahead but keep problem solving human centered. It's practical, it's hands on and it's built for real world impact. In fact, I'm beginning an IDO U AI course as we Speak. IDOU has a whole suite of AI and design thinking programs that show you how to combine AI tools with human centered design to boost creativity, speed up insights and solve problems in new ways. And remember Stackers. IDEO is focused on design and how people actually learn. So IDO use courses are designed to seamlessly transition from theory to practice, ensuring that you can apply those new skills right away and spark immediate progress. Classes start soon, so enroll today. For a limited time, IDO U is offering stackers 15% off site wide. 15% off. Go to idou.comsb that's idou.comsb for 15% off. Idou.comsb this episode is brought to you by Navy Federal Credit Union. Navy Federal can help you find and finance the right vehicle with ease. With Navy Federal's car buying service, powered by Truecar, you can find the vehicle that's right for you as you search through inventory, compare models and you could get an amazing rate when you finance with Navy federal. Visit navy federal.org truecar to learn more. Navy Federal Credit Union, our members are the mission. Navy Federal is insured by NCUA Credit and collateral subject to approval. And we're super happy to have her at the card table. Julie Wainwright's here. How are you?

[Julie Wainwright]

Oh, I'm super. This is fun. This is a good Friday. Let's do it.

[Joe Saul-Sehy]

It is. It is a fantastic day. Although you're letting people in on this because it's Wednesday, Julie. You got to remember it's Wednesday.

[Julie Wainwright]

It's Wednesday. It's Wednesday. Sorry.

[Joe Saul-Sehy]

The miracle of podcasting. Yeah. Hey, how old were you when you created the Real Real?

[Julie Wainwright]

Well, the press got it wrong. They said 53. I was 52. Oh, exactly. So much younger.

[Joe Saul-Sehy]

I know. I don't want to be dated like that. Come on.

[Julie Wainwright]

I know.

[Joe Saul-Sehy]

But there's this myth that it's young people, people in their 20s that are creating companies, Julie. And it's funny because I see a bunch of entrepreneurs that are in their 40s and 50s. Were you afraid, though, to start a company at 52 years old?

[Julie Wainwright]

No, not at all. It was easier than anything before. You know, I think in technology, I know for a fact, because the real real was a technology based company.

[Joe Saul-Sehy]

Sure.

[Julie Wainwright]

It's very surprising for someone put biotech aside because older entrepreneurs do start biotech companies, but in the tech world, and even the consumer tech world, I mean, you're usually, you're not over 30. So it was unusual when I met with people when I was pitching for money because most of the people I met with could have been like, if I had kids, could have been my son or almost my son. You know, it's all men, almost my son. And they all wanted to talk about pets.com. and then I would have to do the math and realize they were probably in grade school when pets.com was happening.

[Joe Saul-Sehy]

Not even old enough to know what could have happened with pets.com.

[Julie Wainwright]

Well, I mean, look, that was the beginning of the Internet. It was one of the first after Amazon, one of the first E commerce companies ever. So they. It's not something that was in their psyche. They were too young.

[Joe Saul-Sehy]

I want to get into pets.com in a minute. And it's funny because that was during my career. I remember getting fired in early 2000 by a client because I think. I think their returns. And this is back when I was a financial planner, their returns in their accounts across the board were only like 52%.

[Julie Wainwright]

Oh, my gosh.

[Joe Saul-Sehy]

And they fired me because 52 was so. But you remember those days.

[Julie Wainwright]

I do.

[Joe Saul-Sehy]

Those are pretty heady days.

[Julie Wainwright]

And then they were minus 50 for a few weeks.

[Joe Saul-Sehy]

It was so funny. After they fired me in 2002, you know, the. The bottom of the bottom. I wanted to call them up and do the Dr. Phil. How's that working for you? Not being diversified, but let's go back. Where did you grow up?

[Julie Wainwright]

I grew up in South Bend and then Mishawaka, Indiana.

[Joe Saul-Sehy]

But before that you were in Kalamazoo, right?

[Julie Wainwright]

I was born in Kalamazoo.

[Joe Saul-Sehy]

I'm from Kalamazoo. My parents. I don't know how well you know Kalamazoo. My grandparents had a fruit farm on the west end of Long Lake.

[Julie Wainwright]

We rented a house on Long Lake that, you know, if you read the book. When I opened the story of me walking off the dock. That was Long Lake.

[Joe Saul-Sehy]

That was Long Lake, yeah. So can you. Can you tell that story because you're three years old?

[Julie Wainwright]

Well, first of all, I didn't remember it because I was three years old. My dad told me this story. So he used to work for Shakespeare Rod and Reel when he first got out of art school. Cause they couldn't get a job as an artist and he was running their pr. But he'd come home from work and he would get in somebody's ski boat because we didn't have it. But he'd wear his suit and go around the. He had trick skis. So he'd go around the lake doing stunts, you know, in a tie and a shirt. And, you know, he probably rolled up tied down, but, you know, Barefoot, with his pant legs. Well, but he was in a suit. And he saw me walking off, literally walking off the dock. And my mother wasn't around at that time. I was the only child. I had every doll I ever owned. And he saw those dolls float away. And by the time he got back to the dock, he was convinced I was drowned and dead. And he looked under, and I had pulled myself up and was, like, looking at him. So I don't even know. You know, obviously I don't remember it, but, you know, he basically wanted to say, look, you saved yourself at three. I think you've got everything you need inside of yourself if you have to save yourself again. But what a story, huh?

[Joe Saul-Sehy]

Well, it's a dramatic story. And it's funny that your dad's in a suit and tie. I mean, a guy who knows marketing very well. You write that you came by marketing kind of honestly because of all the lessons you got, all the training ahead of time. You grew up riding motorcycles. Your dad liked to ski with a suit and tie. It feels like to some degree, Julie, like, taking risk was a part of your life. And yet, when I talk to some entrepreneurs, they're like, the reason I like being an entrepreneur is because I don't really love risk. I want to be in charge because I don't want to risk somebody else making the wrong call.

[Julie Wainwright]

Oh, that's a control issue, isn't it? That's all about control. That's not a bad reason either.

[Joe Saul-Sehy]

Well, that's what I was going to ask is, which is it? Do you like risk? Is that why you. You're an entrepreneur, or is it because you don't like risk?

[Julie Wainwright]

I don't know if that was it. Look, I do think at some point betting on yourself is easier than cleaning up somebody else's mess. How's that? Especially if you have a good idea. But, you know, we always viewed those things as having fun. You know, we had motorcycles. We had go karts, we water skied. When we were. We left Long Lake in Kalamazoo, but we'd go on fishing vacations. We were water skiing, snow skiing. And I mean, I didn't even know how odd it was till I pulled up on my motorcycle. It was little one. They were like. Because he liked dirt bikes, so we would race dirt bikes. But he also wanted them to be licensable. So it was like a 120 Kawasaki 120, where it was.

[Joe Saul-Sehy]

I had one of those.

[Julie Wainwright]

You did?

[Joe Saul-Sehy]

I did.

[Julie Wainwright]

See, they're fast. They're fast and they're easy, and for a kid, you know, they're not hard to maneuver. That was the other thing. So he wanted something. But I remember pulling up at my girlfriend's place. This is in Osceola, Indiana, of all things. We went to high school together. Her dad had a funeral home. And her dad walked out and he said, I want you to tell your dad these are my best customers. Come on these bikes. So, you know, and then I was.

[Joe Saul-Sehy]

Like, that's not the happy thing that you initially think, right?

[Julie Wainwright]

Can you imagine? I'm like, well, all right. And then the other thing I thought was funny, my father in particular was very social, so we always took vacations with other families. And there was one family in particular because they had a son my brother's age, a daughter my sister's age, and my parents loved him. And no one for me or the youngest, but they said their mom wouldn't let them come over when my dad was just home because he was too crazy with the motorcycles. And so these kids grew up sort of afraid of everything. And we grew up not afraid of those things.

[Joe Saul-Sehy]

As you're talking, it just kind of reminds me of when I first learned to ride road bicycles. And I had this friend that was teaching me, like, how to attack the hills and how to kind of stay out of the way of traffic. And I asked this guy, Robert, I said, robert, what if you get hit by a car? And he said, it's not if, it's when. And what's kind of horrible is a few years later, he did get hit by a car. He was in the hospital for about a week. It was. It wasn't great. But what strikes me is I feel like that about entrepreneurship. As I read your words, like, I think entrepreneurs are going to get, quote, hit by the car at some point.

[Julie Wainwright]

It isn't never. It's not, you know, what if you're doing something? I mean, when I was creating the real rail, I was creating something no one had ever seen before and was clearly a threat to the existing luxury brands and still is. There were a lot of obstacles. There were also obstacles because it was a business to consumer business that was disrupting ebay. And most of every. Almost every venture capital firm has an ex ebay exec in there that thinks ebay doesn't need to be unsettled or disrupted. And, you know, raising money as a female is hard. In fact, this woman said, you know, it's really bad. I was talking, she asked questions. I was giving a lecture. And she said, well, look, it's really hard. Women get less than 2% capital. And she went on and on and on and I'm like, and when I was raising money, we got 2.1%, it doesn't matter. And I said, I also was 52 years old. I raised money every six months for the next 11 years. And at least the first round I had pets.com, which was considered a big failure hovering on my shoulder. So I was a female with a big failure who was old. And if I can do it, you can do it. If you have a good idea, you will. Although it is hard right now because there haven't been a lot of outcomes. So VCs are under a lot of pressure.

[Joe Saul-Sehy]

Yeah. Let's go back to early in your career. You finish it Purdue. And the Purdue story by itself is a whole, whole story that I'll let people find out on their own.

[Julie Wainwright]

No, come on, we have to talk a little bit about it. No one talks about it. I dropped out and riveted Monte Carlo rear bumpers in a UAW plant.

[Joe Saul-Sehy]

Yeah. Yeah. You drop out of college and then you end up going back later.

[Julie Wainwright]

Yeah. I missed a semester and luckily for me, the manager, the GM of the plant was that I was going to get married and the guy, it was his father. So I learned so much because the plant was under pretty innovative. Well actually complete renewal. So they were reconfiguring everything with technology and it wasn't going well. So I learned a lot about troubleshooting and problem solving on the spot. And yet you know, they still to ship those cars, they still to get those bumpers. At that time this plant was only a bumper plant and then they were shipped off to a place that would go into assembly.

[Joe Saul-Sehy]

I would imagine a lot too because a lot of the people I'm sure that you worked around didn't have that process management experience like you had which life.

[Julie Wainwright]

No one on the line had it. And then later on when I went back to Purdue, I had the next summer job I had was working at John Deere as a farm out buyer. So again I was, you know, Midwest. You're back in the manufacturing world. And that was great. They're great experiences. And you know, you learned so much understanding process and how technology impacts process even then because shop floor systems were evolving, technology was evolving. There was less accidents in the plants due to safety measures and new technology, even though it was so long ago, was pretty incredible.

[Joe Saul-Sehy]

You have to been though thrilled when you get the job out of college working for a big company like clorox.

[Julie Wainwright]

I was over the moon.

[Joe Saul-Sehy]

Yeah.

[Julie Wainwright]

And I'll tell you two reasons. One is my consumer psychology professor called and said, I've got this wonder kid here that you guys have to meet. And then, well, there's three reasons. And then the. At the time, the CEO had graduated from Purdue undergraduate. So he's like, oh, a Purdue wonderkid in consumer psychology. So he wanted to meet me. And then secondly, they had hired one undergraduate, and that guy's name was Steve. And Steve was doing phenomenally well because I was the second undergraduate they ever hired. So he was a big success and they didn't have to pay him as much, as opposed to an MBA student. So if he wouldn't have worked out, it wouldn't have mattered that one call from the professor wouldn't have mattered. The.

[Joe Saul-Sehy]

Forget it.

[Julie Wainwright]

Right. So luckily he did really well, which opened the door for a few more of us to come in.

[Joe Saul-Sehy]

But still, I feel like when I got to the part of your story where you leave Clorox, a lot of our stackers, you know, they're in good jobs, jobs that they tolerate but not that they love. And they might be thinking about entrepreneurship or thinking about the next thing. It felt to me reading your words. I want to know what you felt when you decided to leave Clorox to go explore a much, much smaller company. It's like going from this mothership that's not going to go anywhere to, you know, maybe this new company you go to works, maybe it doesn't.

[Julie Wainwright]

Well, all right. It was the beginning of the personal computer software industry. And I didn't know if I was joining a good company. And I mean, it was good for. I had a good run and it was really well run. But I did know that going into an experience when I really thought that was the future personal computer software, I had never used. That's not true. At Purdue, you had to learn how to program. So I was down there with the punch cards. It's just all, gosh, just something you had to do. And then we worked on terminals too, you know, like, I always called them dumb terminals. But when I graduated, you had to take computer science, and that meant writing code and down there. And you didn't want to drop those damn cards.

[Joe Saul-Sehy]

Oh, yeah. Then you've got a programming mess.

[Julie Wainwright]

Yeah. And then also the people that were down there all the time, even back then didn't shower a lot, you know, and I came down in my little skirts and high heels.

[Joe Saul-Sehy]

It smells like the computer department.

[Julie Wainwright]

I just remember it being cold and Dark down there, because it really was in the basement at Purdue. I even remember the building. So I had had experience, and we were using terminals to access data at Clorox and running all kinds of analysis off of that. But it was crude. It was like a tertile analysis or a quintile analysis by market looking at shelf movement data. So, you know, we had to learn how to use data and run those. But that really wasn't transforming things. And then when this guy from the finance department smuggled in this Apple II computer and showed me how I could stop hand calculating P and LS and doing what ifs by hand and set up the program, I'm like, this is the future. So I get a call to join a company that was probably 4 million in revenue. But remember, I was young. I was 25. And here's the thing I think is interesting. I remember this so well. I was making $50,000 a year at Clorox at 25, and I thought, I'm making too much money for my age. And I didn't see any women above me in brand management at all, because when they got to a certain level, they went into hr.

[Joe Saul-Sehy]

Julie, I'd just like to put this into context for everybody, because I did a little bit of the, you know, the rule of 72 that's like today making around $300,000.

[Julie Wainwright]

Oh, it felt like a lot. It was a lot of money.

[Joe Saul-Sehy]

Yeah.

[Julie Wainwright]

But I thought I could get used to this money. And I'm 25, and I don't want to be the people I see above me. And then a personal computer technology company interviews me and offers me a job, and I'm like, this is. I don't know. But they could pay me 25k. So. And I thought, I don't know what this is going to do, but I know this is the future and I want to be part of it. And there was no way to evaluate if that company was going to win, because at that time, there were three or four personal computer software companies. There just weren't that many. It was an opportunity of a lifetime to join the personal computer software industry.

[Joe Saul-Sehy]

Just what a huge move for your entire career. And to have that kind of. I. I don't know, to have the resilience to be able to jump off and make that.

[Julie Wainwright]

That's youth. That is youth. That's where you think you're invincible. And if you mess up, you can always figure it out later.

[Joe Saul-Sehy]

Yeah, but you did it again at 52, though.

[Julie Wainwright]

Well, I didn't have any choice. Because no one was going to hire me. I was on a path of figure out, start my own company or look, and this is a perfectly honorable thing I'm going to say my. My plan B, which to me was bad, and I'll tell you why. It had more emotional negativity. My plan B was go to Arizona, become a real estate agent, and dodge rattlesnakes. And I actually love parts of Arizona, but I hate the heat. You know, that intense heat. And they have snakes, and I really hate snakes.

[Joe Saul-Sehy]

Arizona, Send your hate mail to Julie. Not to me.

[Julie Wainwright]

No.

[JJ]

No.

[Julie Wainwright]

I love Sedona. I think it's a beautiful state. I love Sedona. I love Gorgeous. But it's beautiful. It's one of my favorite. It's beautiful. But I didn't want to be in Phoenix selling real estate and then going for hikes where you run into rattlesnakes. I just thought, this is my future. It was either make this company work or, you know, it wasn't going to be good. And I gave myself a couple of years, so my back was against the wall the second time.

[Joe Saul-Sehy]

I like this idea mentally, of leveraging yourself by saying, it's going to suck if I don't do this. If I don't do this, my life is going to be hell. So you're talking yourself into it.

[Julie Wainwright]

I feel, yes, I was. But it was also, you know, at 52, you've got less years in front of you than you, you know, And I don't know, I just felt like it was time. And I also took stock. I knew what I wanted. I knew I wanted to get into E Commerce. I knew I could do it better than anyone. You know, maybe not Jeff Bezos, but I knew I would do a great job. And I just had to come up with an idea. So I would say it was a calculated risk that paid off. But the downside was not good. I mean, the downside for me was not good.

[Joe Saul-Sehy]

Yeah, you were at Berkeley Systems.

[Julie Wainwright]

I was the CEO. I was promoted to the CEO there.

[Joe Saul-Sehy]

So were you the person that said, let's make you don't know Jack? One of my favorite games of all time.

[Julie Wainwright]

God, that was so much fun. I would say that was a combination of me first getting them focused because they were trying to do too much in too many categories. So working with the founder, whose name is Wes Boyd, to get the development team focused, because when I walked in, they were doing still screensavers and they were doing edutainment and they were doing this. But their real core strength was entertainment. So paring down and getting them focused on one category and then opening our minds up to, there are many ways to get this type of product built. And this young guy and Broderbund had done this way back when they had an affiliate program and we were talking about a hybrid program. What if someone came to us with a great game idea? We combine that great game idea with great technology, marketing and distribution. So another company came to us with the game. It was called Jellyvision. But they had it in a hyper stack. It seemed fresh and alive and it felt like something we could get behind. I knew I could market it. So I would say my role there was keeping the company financially solvent, keeping them focused. And then I do take responsibility for launching that superbly, even though I was the CEO and really making it a huge hit. But tech is a collaborative world. If the founder, who was incredibly talented as an engineer and had a lot of foresight, if he would have said, no, I hate this, we wouldn't have done it. You have to respect people's point of view and their talent. So he was really talented and he was also the founder of the company. I was really the gun to hire to make sure that we could pay the bills and keep it going.

[Joe Saul-Sehy]

But for you guys to recognize just how different that game was, how the writing was so fresh, the so much fun. Hilarious. Cookie Masterson, my goodness, that's a character that I just, you know, you feel like is your best buddy because he's so quirky and weird.

[Julie Wainwright]

But it wasn't. Wait, I dipsed it. This is really a good lesson. You know, it wasn't graphic intensive, right? It was. It was audio intensive. And it was a little smarmy. A little smarmy.

[Joe Saul-Sehy]

A little.

[Julie Wainwright]

All right, a lot. But it was also fresh. And so I kept thinking, how am I going to get this sold? How am I going to introduce this game? Because you're not running television advertising. And we had brick and mortar distribution. Then there was a big chain, an important chain, called CompUSA. And I went to them and I said, what I'd like to do, if you'll let me do it, is set up in your key cities, a demo. We had this really fun demo that would run with speakers on a pile of games where the game is basically the announcer. It was an announcer driven game which invited you to take and so bought speakers and then turned that off and got all the gamers that came in to play the game. People were laughing through all this excitement and that was solving a problem because no One had seen a game like that at that time, it won Game of the Year. At that time, you had oppressed discs. We were also. We had restructured the company. We didn't have a lot of cash, so we got 100,000 out, sold out before Christmas. And it just went and went and went and became a, I think, I don't know, about 30 or $40 million game overnight. But, you know, you have to. Whenever you introduce a new concept, you've got to figure out, how do you change people's perceptions. No one had seen a game like this and it wouldn't translate at that time. People were reading reviews of games.

[Joe Saul-Sehy]

Yeah.

[Julie Wainwright]

And this would not translate because it was something people hadn't seen before.

[Joe Saul-Sehy]

Yeah, you're doing a trivia thing where instead it's this quirky, to your point, smarmy. You feel like you're a game show contestant. And it's the weirdness that hits you no matter how the noise it makes when you press the button for people haven't played, you don't know jack. You got to go. You got to go find that. Well, let's get to you go from there. What [e-mail]? you know, for our younger stackers, you describe pets.com as chewy but better. And you said, you might be biased, but you were doing what chewy does then. But even better. But what [e-mail]?

[Julie Wainwright]

Well, all right. When pets.com got funded, it was funded by a company called Hummer Wemblatt, a venture capital group, and Amazon. All right, those were the two big funders. And other people came in. When we made the announcement of getting funded, the thinking was, well, if Amazon's behind this, because they had also put money in another company called drugstore.com, which went belly up. But if Amazon is behind it, along with a reputable VC firm, no other pets companies are going to get funded. Well, seven more got funded after that, so that's number one. That just shows you how frothy the market was then. We just ran like hell to execute, raised, I'm going to say, $100 million and went public early. You could argue too early. But we were the last company to go public. And the reason we were the last company to go public is Amazon in 1999 had lost almost $1 billion in Q4, and they announced their earnings, which shocked the financial world. In Q1, when we were on the roadshow and all of a sudden our financing meeting started evaporating. The bankers would tell us and told me no one's going to buy that you'll ever get to profitability if Amazon is getting bigger. But losing this amount of money every single quarter, it literally wiped out every company. No business to consumer company could get fined. It was the beginning of the collapse.

[Joe Saul-Sehy]

So you couldn't even get a meeting?

[Julie Wainwright]

No, no, we got meetings. We got out. But it wasn't with enthusiasm. You know, we got out. We were not oversubscribed, so we got out. We did raise money. The financial strategy at the time was go public if you can, and then do a secondary follow on within nine months. That wasn't going to happen for the company. So I cut costs, right? We raise all this money, I go back, I cut costs, I have layoffs. And we try to figure out how we can get to profitability faster, which you can't because these businesses are businesses of scale. And at that point, you had to build every piece of software. We had our own op centers. And then I ended up shutting the company down and giving money back to shareholders. Even though we had a net positive worth, we didn't take it to bankruptcy, which, by the way, was a mistake. Big mistake. And the reason I did shut it down was I didn't think we were going to get out of this financing drought. But I could have been wrong. Turns out I was right. But it was. I could have been wrong. And there were other companies going through that financing drought. One of them that's pretty famous right now called Netflix.

[Joe Saul-Sehy]

Never heard of it, no idea what is that company?

[Julie Wainwright]

So it was just, you know, it was in it too, but they navigated through it. They had had a few more years behind them because they. When real.com was going, real.com was the other company I ran. Came in as the CEO, not the founder. And that site sold movies, didn't rent, sold movies. When people bought movies and DVDs or cassettes before that, and that sold to Hollywood Video with their intent of shutting, slowing down the Internet, which is pretty funny. So anyways, he navigated. The question is, could I have navigated the brand and done, you know, I don't know. I didn't try. I was trying to be so fiscally responsible that I'm not sure that was the right decision. Now, my current investors would not have supported us going forward. So they weren't up for more money. They were seeing other companies go through some pretty bad times. But yes. So I had to shut Pets. I chose to shut Pets down. Not sure it was the right decision. Right after that, Webvan shut down, which Lost a billion, like 1.1 or 1.2.

[Joe Saul-Sehy]

It lost a ton more money than pets.com lost.

[Julie Wainwright]

I know, but you know, that was also the precursor to DoorDash or Instacart. So there was all these building blocks being laid. The foundation was being laid. But you need, for those businesses to succeed, you need capital. Just like, you know, and Amazon went through a hard time where, after 1999, where it could have fallen, but they, you know, they thread the needle.

[Joe Saul-Sehy]

One of my favorite lines comes from this period of heartbreak that you have. In fact, you write that your husband left the day you were shutting the company down. Talk about a gut punch. But one of my favorite lines, Julie, is this line. I let it define me until I didn't. What does that mean?

[Julie Wainwright]

Exactly what it says. I took on this cloak of failure until I realized it wasn't my cloak, it was public perception, it wasn't mine to wear. And so I lived in this state where I was beating myself up, second guessing myself, considering what I would do next, how I'd navigate. I mean, I had, it wasn't just shutting the company down, people. I had weird things happen at my house. I had odd things happening at social events that were really horrific to me personally. But they were all about me running pets.com and at some point you just say, f you, this is my life. I need to stop this and stop wearing other people's expectations because I'm losing my life and I need to move forward. So, yes, that's what that means. And once I got there, it was no going back. I mean, it was like, okay, we're done with that. We're done.

[Joe Saul-Sehy]

Well, look at now because I, you know, I talk to people about the fact that I'm going to be talking to you and you're known as the queen of the real real. And pets.com is way back there. And the real real is this cool thing, this whole genre defining thing that you created, which is incredible. But let's talk about the real real, which is really there's so we could talk for 15 hours about the, the real real and so many business lessons. But you know, stereotypical consignment store, right? Smelly, dark, like sketchy. I love you. Talk about walking into a pawn shop that supposedly deals in luxury goods and oh, and it just felt so slimy.

[Julie Wainwright]

It was so gross even bringing that up. It's like I relive it. It was so. And demeaning, you know, just like, oh, this Cartier watch is out of style. And it was like five years old.

[Joe Saul-Sehy]

Yes, but how do you redefine that genre with the realreal?

[Julie Wainwright]

Like you did look, it was calculated. And I would say there's multiple things. We had to change people's perception of wearing pre owned things. And my point of view on doing that was don't break the romance of the brand. These brands are beautiful. They need to be shown even as a secondary market in their beauty, not on the back of a closet door. So you need to show that they're relevant. And showing them relevant means showing that they're still cool, they're beautiful. Putting them on models that are out, mixing previously owned with new. So putting out in front of people this idea that it doesn't matter if it's pre owned because it's still beautiful, it's high integrity, high quality. And that was done visually and we did do home parties too at the beginning. But it really comes down to visually changing the way the product is shown, both on the site but also doing editorial to focus on that. That was intentional. We had to change perceptions. You know, you think about if you're going to get anything evaluated for let's just talk about the jewelry or fine watches. You don't want. You want to know what you want transparency, you want a beautiful environment. You don't want pressure to consign. So putting a gemologist front and center that evaluates things in front of you in a beautiful office and then gives you a written document says we'll stick with this for six months, not maybe the price will go down tomorrow, which is what. And that's honoring. In that case, you're also honoring the consigner and the fact that parting with jewelry can be. Sometimes it's a bigger decision than may be addressed in most cases. And they're also beautiful items. So it should be in a beautiful place. So I would say just thinking about it, not as a secondary market, but as a consumer experience and changing perceptions. And I knew it, I knew it had to happen and I knew what it wanted to feel like. And certainly everything I did testing out the competition reinforced it would, I hate to say it would be so easy to compete with these people because they weren't people that engendered confidence.

[Joe Saul-Sehy]

Well, and by showing it in a confident light, I mean a luxury good, you need to be the confidence is the good. The fact that I have a real Rolex and not a one, a cheap knockoff Rolex is all about confidence. I feel like to retain the value of what you're selling, that's what you had to do as an entrepreneur, right?

[Julie Wainwright]

Absolutely. I always say don't break the romance of the brand and respect both the product, which is what you just said, and also the person selling it and the person buying it. And these are considered purchases. But, you know, it came down to changing perceptions. Overall, I think the Rolex is a good example. The men's watch market for a long time has had a very vibrant secondary market. And they had Sotheby's or Christie's, the big auction houses, glamorizing that and glorifying it. So there was something to be learned there too. You know, when you affiliate with Sotheby's and you buy a Philippe Patik or a Rolex or you buy Steve McQueen's watch, it has a history, it's beautiful. It has integrity. So bringing that into more of a mass market without losing the allure and the prestige, that was the goal. And we did pretty well, I think.

[Joe Saul-Sehy]

Pretty well. Julie's an understatement. But let's end with one last question. A lot of people think that being an entrepreneur is this solo thing, right? And yet in your book, you talk a lot about the people that you have to surround yourself with, making sure you've got the right who's. But also partnerships were really important in your success. But partnering and trying to partner with some of these big department stores, some of these big brands, and you mentioned Sotheby's. Talk to me about the strategy of partnering and how that factored into the RealReals success.

[Julie Wainwright]

Early on, we did a deal with Saks and with Neiman Marcus. I mean, ended because Chanel put demands on us through them. That ended fairly quickly.

[Joe Saul-Sehy]

Why is Chanel so intimidated by you?

[Julie Wainwright]

Well, you'd have to. I think it's all in the court documents. How about that? We'll just say that it's all in the court documents.

[Joe Saul-Sehy]

Fair enough.

[Julie Wainwright]

They do not like a secondary market. End of story. But having that initial relationship for nine months and the exposure did benefit the company because we were only about 100 million then, it helped people understand what we were doing. And it also helped, didn't hurt Neiman's or Sachs, because people would. Then it would sort of like an open to buy. They'd sell their things in the closet. They'd go, oh, I have a lot more money than I thought. Now I'm going to buy something new. So it was reinforcing this circularity of what happens when people shop and the fact that if you buy things that have good quality, they do have a resale value. It worked for them, it worked for us. And then yes, it was an important relationship at the beginning. It ended prematurely, but it still benefited the company.

[Joe Saul-Sehy]

But did you go hunting for those? Like, was that, I'm imagining a whiteboard and you're, you go, okay, we got.

[Julie Wainwright]

To go after Neiman Marcus. No, there aren't. Well, there, I mean, you know, now there's less. But there was Barney's, Neiman's and Sachs really, that had that kind of luxury. Barney said they could do it themselves and of course they couldn't. Neiman's was the one that was like, oh, well, this is worth trying. Sachs put, stuck their toe in the water.

[Joe Saul-Sehy]

Did you call them initially though, Julie?

[Julie Wainwright]

Oh, of course, of course. Knocking on doors. And then when we got to 500 million, I went overseas and started meeting with Kering, which has, you know, Gucci and St. Laurent and then LVMH, which is Louis Vuitton and Christian Dior and Celine, et cetera, and trying to get a partnership going there. And the only one that worked was Stella McCartney. But it was great. That was a great one. I think it's still going on with the company. That was a great partnership. And she understands sustainability and fashion. That's her whole brand. And she understands the circular economy and she likes shopping secondhand. So when they said yes, still a luxury brand, saying yes, they wanted to work with us to promote the circular economy. It really helped elevate our company and put a couple shockwaves through the industry.

[Joe Saul-Sehy]

So much more here. Stackers Hiring when to Fire People, Looking at Finding investors. So, so much more. Julie's book is called Time to Get Real How I Built a Billion Dollar Business that Rocked the Fashion Industry and it certainly did the fight with Chanel. Just, just, just one of those, one of those stories and it's available everywhere. Julie.

[Julie Wainwright]

Yes, I'm excited about it. Amazon just voted it as one of the best business and leadership books of the year.

[Joe Saul-Sehy]

It is a roller coaster ride. Stackers. Julie, thanks so much for mentoring our stackers today. I super appreciate you and appreciate the work that you did here.

[Julie Wainwright]

Oh, thanks for having me on. I appreciate it.

[Sherman]

Hey there, Stackers. I'm Joe's mom's neighbor, Doug and I can't stay long. It's Margot Robbie's birthday and I've promised to pick her up and take her to dinner. Kinda, I mean I it call called her publicist and by that I mean the receptionist. But good news, the fourth time I called and pretended to be her brother, they put me through to her assistant. When she said Margot's booked, I totally flipped out. I mean, booking her was that easy. So it appears Margot is coming to Texarkana to have dinner with me. Margot, of course, lit up the screen last year as the face of Barbie, a woman who's had some serious makeovers over the year and now is a hot property. Much of this is due to the man who was president and COO of Mattel, Richard Dickinson. Richard has now gone on to run another company, this time in fashion that used to dominate mall sales in the 80s and 90s but has faded lately. What company is Richard Dickinson CEO of Now? I'll be back right after I figure out what Margot Robbie's favorite band is. I'm going to see if they'll come and play for us. Margo's going to love it.

[Joe Saul-Sehy]

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[Doug]

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[JJ]

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[Sherman]

Hey there stackers. I'm music lover and guy who who didn't know how much bands charged Joe's mom's neighbor Doug. So it turns out Beyonce charges way more than mom would loan me. So I guess we're gonna hit up the local dive bar Fat Jacks after dinner at the Sizzler. Margot will still love that, don't you think? In honor of Margot Robbie's birthday, here was today's Barbie related trivia question. The president and COO of Mattel during Barbie's resurgence was Richard Dickinson, also of more cowbell fame.

[Julie Wainwright]

Right?

[Sherman]

Same guy, isn't it?

[Joe Saul-Sehy]

The Richard Dickinson. I'm sure he walked into the new company and said yes, the Richard Dickinson.

[Sherman]

Yes, he is now at the helm of one of America's biggest fast fashion companies. A collection of brands that used to rock mall and strip mall sales. They're still around, but not nearly as hot as they used to be. What brand has Dickinson been trying to revive? If you said Gap, which includes other brands like Old Navy and Banana Republic, you'd be correct. Nice work. I'll tell Margot how smart you are when she gets here. And now back to two guys who could be models for Ken and Ken's nerdy banker friend Joe and og.

[Joe Saul-Sehy]

I think I'd be Ken.

[Sherman]

I let you two sort it out. Fight. Fight. Fight. Fight.

[Joe Saul-Sehy]

A great piece a few months ago in Fast Company magazine, by the way, about Dickinson. The piece rights turning around Barbie was hard, but the issue with Barbie was she was a lightning rod. People either loved her or they hated her. She's like either what women stood for or not what women stood for. I remember when Autumn was playing with Barbie. Cheryl's sister wouldn't let her daughter play with Barbie. She's like, I don't want any Barbie in my house. And now of course Cheryl's sister was the first one line for the Barbie movie starring Margot Roby and it's like all about Barbie. Barbie's fantastic. Dickinson and company. There's a great piece there. And they said the problem with the Gap is different because where Barbie was still a lightning rod, people just don't give a about the Gap anymore. They're just like, yeah, Old Navy. It's where I go pick up school closer my kid, you know, the interesting thing was I went and looked this up. The last five quarters in a row, same store sales for locations open at least one year have increased five quarters in a row. So Dickinson now finding a way to turn that around. Although the piece that I was reading is about how tariffs for Gap, along with a lot of retailers are problematic. But, but going back to this, OG Companies find a way, right? I mean, this whole piece that I'm reading about Gap in the tariffs, Richard Dickinson and everybody else going, hey, how do we make sure that we keep this?

[JJ]

All they're doing is trying to solve that problem.

[Joe Saul-Sehy]

So owning, owning the stock in the company and we're not saying own stock and G, we're saying owning stock in the companies is the way to go. All right, let's do a headline.

[Julie Wainwright]

Hello, darlings.

[JJ]

And now it's time for your favorite part of the show, our Stacking Benjamin's Headlines.

[Joe Saul-Sehy]

Our headline today comes to us from the Jason's Week. We should keep track. OG of which writer gets the headline spot the most. But Jason, I think, might be fighting for it because jason, voice of intelligence over at the Wall Street Journal, Jason says even sophisticated institutions sometimes fall into the trap of putting an unhealthy number of investing eggs in one basket. Jason begins this piece by saying if you need to ask whether you have too much money in that one investment, the answer, it's probably yes, is yes. Just do I have too much? Yes. Yes, you have too much. Even after the latest bout of tariff turmoil, stocks have mostly recovered their April losses at the time that we recorded this, by the way, which is a little bit early. So things might have changed in the last few days. So readers, friends and family are asking me questions like, is it a bad Idea to have 85% of my portfolio in Nvidia? Should I own some stocks other than Apple? If Bitcoin's 90% of my assets, should I scale back for something like 99.95% of people? The answer is yes. This is interesting, OG because he goes on to talk about how Warren Buffett and Charlie Munger have repeatedly said that diversification is the win. You look at Berkshire Hathaway's assets, the company that they managed for years and years and years together. It's a diversified collection of companies like they they practice diversification as a way to make more money or at least avoid huge, huge, huge losses all at one time.

[JJ]

Is it that Diversified, though. I don't know.

[Joe Saul-Sehy]

Insurance companies, Dairy Queen, Coca Cola, real estate, brokerage firms. Like, it's. It's kind of all over the place.

[JJ]

Yeah. I think his advice around diversification is a really great way not to get poor. If you look at the largest wealth creation from stock ownership, it's not from being diversified. And this is the thing that I think that's really difficult for most people to have this juxtaposed thinking. If you look at Elon Musk or Jeff Bezos or Larry Ellison or any of these people, they made all of their money by being super concentrated. But those are like lightning in a bottle. That's the stuff that you see. That is the one out of X,000, 100,000 million that were successful. Right. So you see that one success story. You don't see the other ones that weren't successful. But there's a case to be made for leaning into the thing that you're really good at. And if you're, for example, an entrepreneur. Most of my just personally, most of my net worth is in the value of the businesses that we have. It's not in. I mean, I have ETFs, and I have my 401k and I have stuff like that. But the vast majority of my net worth is in the businesses. It's very concentrated. But I'm also operating those businesses, if that makes sense. So I'm not a passive investor.

[Joe Saul-Sehy]

Sure. Zweig actually talks about this even in a broader context. OG he says few stocks have performed better in recent years than Nvidia. Consider what's happening at the Jen Sung and Lori Wang foundation, created by Nvidia's founder and CEO, Jensen Wang, and his wife. As of December 31, 2019, its assets consisted of 378 million in Nvidia stock. Let me go back to that. December 31, 2019, 2019, it was $378 million. Pretty good foundation over the four years after that. Right. Nvidia goes on a tear. 378 million to $3.4 billion. Even after they've donated over 170 million in grants, according to their tax filings. Yeah, Nvidia did 745% over that period.

[JJ]

So I think that if you're in a position that you're starting to accumulate wealth, so you're coming out of school, you've got your first job, you're starting your retirement plan, and you are putting Money in your 401k, should you put it all in one stock or should you be putting it all into or should you be diversifying in a bunch of ETFs? I think you put in a bunch of ETFs. I think that you don't have the expertise, time, energy, any of that stuff to pick winners. And also it's impossible to do successfully long term if you're in a position where, and this is where I think it gets confusing, if you're in a position where you get awarded stock or you've been in a position where your net worth has grown because of some one particular event, you own a business that's done really well. You have stock options in a company that has taken off and now you look at your balance sheet and you go, I've got this great balance sheet, but it's highly concentrated in one thing. I think the hard part for an investor is to look at that and say the right thing is to diversify it. Even if it's going to cost me some pretty substantial taxes to do that because I can't guarantee that that over performance is going to continue in advance if you're an investor or if you're an employee of Nvidia. And I think I read an article that they've made some five figure number of people millionaires in their company. Tens of thousands of people have turned into millionaires because of RSUs and stock credits. So using Nvidia as an example, or any other company for that matter, if you look at your balance sheet and you go, yeah, I've got my 401, I'm putting my 10% in, I'm maxing it out, I've got my HSA, Roth, IRA doing the thing, but my balance sheet is 90% company stock. Because I got lucky. I happened to join the company at the right time. I helped it be successful. You know, I did my part. My company has grown so substantially that now I've got this $5 million net worth with 4 million of it being in company stock. Or you know, I've got a million dollar net worth, 800,000 is my company because it just went public. The hard part is, and this is the difficult thing for an investor in that is like they see that recent bias, they see that recent history and go, why would I want to sell this? I mean, it's up tenfold in five years, man. Like, come on, I don't want to sell it.

[Joe Saul-Sehy]

We see something else too that Jason points out OG on that over performance.

[JJ]

Does not continue into infinity. It just doesn't happen.

[Joe Saul-Sehy]

I love his.

[JJ]

What does Jason say?

[Joe Saul-Sehy]

I love his other reason. I mean the one is, I don't want to sell it because it's done so good.

[JJ]

It's done so great.

[Joe Saul-Sehy]

It's the good one. And then you wait too long. He said. The other problem is we all think we have superior skills when most of us don't. And when you go on a good run where the company. You don't credit enough of that to, the company, hit a great, phenomenal patch. You just happen to be at the same place with a company that's making money. Like the fact that you stumbled into it. No, it's. You're a freaking genius. And you know what? I want to just keep patting myself on the back instead of realizing that I might not be as skilled as I think I am.

[JJ]

Huge market forces are in play in a lot of those things, too, that go beyond, you know, if you're a tech worker, your coding capabilities. I mean, hell, even Zuckerberg would point out the fact that he is his fortune in Facebook. And the movie, if you watched it, would say that he kind of stole it. But his fortune happened to line up with how all of this worked. Malcolm Gladwell's book about outliers, when he talks about how the timing of all of that worked in terms of. He's talking about birthdays and that sort of interesting thing. It so happens that all of the tech founders were all kind of born around the same time. They were born at a time where, when they came of age, as they were transitioning into being a young adult, supercomputers at the time, regular PCs were more able to be, you know, they were able to be in rich people's houses. They were born at a time where 10 years earlier, they would have aged out of that. They would have been in college when that stuff happened. It's about your own life, and you guys are profoundly older than I am. So this is probably just really just kind of land a little for you. I know that you guys went to school during time when there wasn't a profound amount of Internet or email. Think about the transition, the difference even just in our. And I say you're much older, but just in the little bit of age gap that you and I have or the three of us have in terms of what normal was. I remember Lissa telling me about Bluetooth. She's like, no, no, no. I read about this. She was in college. She goes, I read about this. She's like, you're gonna have your device. And I had, like, a Palm Pilot, you know, because it was super cool. Back in the late 90s early 2000. She's like, no, no, no. You'll be able to take this device and like, hold it next to the printer and it'll print. I go, come on. No. She goes, no, no. I said, yeah. Like WI fi. She goes, no, it's not WI fi. It's a different thing. It only works, like low, like really close. And I'm like, that doesn't make any. Who would use that? Doesn't make any sense at all. That sounds ridiculous. And now when your AirPods don't work, you're freaking out, why is my phone not working? You're like, oh, sorry, Bluetooth off. It's like a common thing. But move that generationally by five years and you don't have that experience. And I see that with my kids too. So to your point and to Jason's point, I think you're not as good as you think you are. Some of it is, hey, you got hired in 2016 to work at this company and didn't graduate college in 2008 when there weren't any jobs. Because the guy and gals who graduated in 2008 worked a different career path. That wasn't this. Not through any fault of their own. That was just what was going on.

[Joe Saul-Sehy]

He goes on to talk about other foundations. He talks about the Lilly Foundation. Once zeppbound got big people that don't know zepbound is like Oz Epic. And so a Lilly foundation, mostly Eli Lilly stock, but other charities. And these charities, by the way, are filled with really smart people running them, right? So Ford, Gates, Kresge, they all took this concentrated position and they diversified them once they got to a certain point going, listen, we had a great run. Gates is an example of Microsoft had a great run. But now our goal is to spread this wealth out.

[JJ]

The vast majority of his net worth.

[Joe Saul-Sehy]

Is still majority of his, but the foundation, the foundation has been diversifying aggressively as he does very well. Jason juxtaposes what's going on with this weighing foundation, which is Nvidia, and another foundation which is the Barbie foundation, not the same Barbie we were talking about earlier. This is B A R B Y, which is the founder of VF Corp. They make clothing and footwear. Over the 10 years ending December 31, 2019, VF Corp. Generated a stellar 21.9 annualized return every year, going up to almost 22%, far outpacing the S&P 513.6. I mean, that's a big, big, big third more money every year at that point. The investment portfolio of the J. Barbie 8 FBO 10 acre foundation was almost completely VF shares. The assets were 3.3 billion, with 3.1 billion in VF alone. So here's what we got. We got 3.3 billion, of which 3.1 billion is in one stock. And this is in December of 2019 versus that Nvidia foundation which had $378 million at the same time. Subsequently, VF stocks unraveled, losing about 78% by the year end of 2023. And now the Barbie foundation is tiny comparatively, while the Nvidia foundation is huge. And to your point, the the big aha here is lack of diversification just creates greater standard deviation.

[Sherman]

I mean, for me, the big aha was that's what you get for starting out making barbecues like Australian barbecues.

[Joe Saul-Sehy]

Is that what they make?

[Sherman]

I think that was their origins. Shrimp. They put shrimp on the barbie, right?

[Joe Saul-Sehy]

Oh, I knew there was something going on there.

[Sherman]

I I don't know any other way to do that. Logic puzzle.

[Joe Saul-Sehy]

And then he goes back, guys and talks about the winners always rotate too. He said it was back in March 27th of 2000. You know what company surpassed Microsoft to become the world's most valuable company back in March 27th of 2000? Cisco Systems.

[JJ]

Oh, Cisco, yeah, yeah.

[Joe Saul-Sehy]

GE, Cisco, everybody who says no, no no, hold it forever. That single stock. It is possible og to be in the stock for too long. Great piece. We will link to this on our show notes Jason's week with another home run and of course more goodness about all these financial planning topics at our newsletter, the201, stacking benjamins.com 201 gets you there. That is always free and you get an email delivered hot and fresh from us to you in your inbox every week. All right Doug, onto the back porch. What's happening on the community today, my friend?

[Sherman]

Joe, we've got a fast. Fantastic fast. Fantastic fast. I'll do it as fast as I can, but this one actually is worth savoring a little bit. It's a great review from J. Mez Phillips.

[Joe Saul-Sehy]

Oh thanks Jmez Phillips.

[Sherman]

Jmez says enjoy the show but disagree on one point from the 5:28 episode. I have been listening to your podcast for many years now and enjoy every episode. As a former CFP from a prior life, I find your advice spot on. I have recommended your show to many of my family and friends and I am pretty sure my wife is sick and tired of hearing me start sentences with I heard this thing on Stacking Benjamins today Jamez, I gotta tell you, she's sick and tired of a lot of stuff you're doing. I also enjoy the comic relief. That means you, Doug. And yes, the trivia is very entertaining. However, I do take exception with your recent back porch where you said children should refer to adults as Mr. And.

[Joe Saul-Sehy]

Mrs. Oh, that was in a different part of the show. And by the way, so many people talking about this. Yes, lots of discussion. You know, it's funny. We talk about the 4% rule. Decumulation, international investing, food waste, and everybody wants to talk about whether you should call adult their first name or not.

[Sherman]

So get this. He tells a great story about this. He says, when I met my now in laws at 17 years of age in 1985, they demanded that I call them by their first names. No one called them Mr. Or Mrs. And we were the same way with our daughter's friends when they came. Excuse me. When they were young, five years old, they all called us James and Allison unless they were uncomfortable doing so. Respect is shown by how you act, not how you address someone. Joe, you can call me James. OG, you can call me Mr. Phillips.

[Joe Saul-Sehy]

Did he really write that?

[Sherman]

He really wrote that. He says, have fun and keep making podcasts. You're helping and entertaining people. Two great things.

[Joe Saul-Sehy]

That's fabulous. Thank you so much for that. And thanks for the kind words. That's fantastic way to end our Wednesday. Thank you for referring people because, you know, if you got people in your life that are taking out the 4% and they could take out at a million dollars, $15,000 a year more, they.

[JJ]

Can take you on vacation.

[Sherman]

Yeah, I was going to say you get a cut of that. Like if you're the one to tell the. Share with them. I heard this thing on Sacking Benjamin's. I think you should get a cut of the extra point seven.

[Joe Saul-Sehy]

I think there's a case to be made. There ought to be a law. There ought to be.

[Sherman]

You know what they say?

[Joe Saul-Sehy]

All of them. Well, here's what they don't say. Doug says. Doug gives us our to do list at the end of every show, and this is no exception. Doug, what's our three things we need to remember and put on our to do list?

[Sherman]

Well, Joe, first, take some advice from Julie Wainwright. The only way is through. So get moving on your idea and turn it into reality. Second, that one stock. Yeah, you do own too much of it. But the big lesson, Big thanks to Og for explaining that Margot's assistant saying she's booked that night, might actually have a Negative connotation. So maybe I should cancel the reservation. Or better. Oh, better yet. Hey, ma, want to go listen to some tunes at Fat Jacks with me? Thanks to Julie Wainwright for joining us today. You'll find her new book, Time to get How I Built a Billion Dollar Business that Rocked the Fashion Industry. Wherever books are sold. And because I like you, I'll have my people include links in our show [e-mail] this show is the property of SP Podcasts, LLC, Copyright 2025, and is created by Joe Saul Sehive. Joe gets help from a few of our neighborhood friends. You'll find out about our awesome [e-mail] along with the show notes and how you can find us on YouTube and all the usual social media site spots. Come say hello.

[Joe Saul-Sehy]

Oh, yeah.

[Sherman]

And before I go, not only should you not take advice from these nerds, don't take advice from people you don't know. This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I'm Joe's mom's neighbor, Doug, and we'll see you next time. Back here at the Stacking Benjamin show.

[JJ]

We are a little ahead of recording, and so we haven't had Father's Day yet. Do you guys. When you guys think about Father's Day, do you think, like, I want to spend time with all of my family and kids, or do you think it's Father's Day? I shouldn't have to.

[Sherman]

I feel like there's a right answer here, but are you leading us onto something?

[JJ]

Which one of those. Because I feel like on Mother's Day, my wife's like, look, it's Mother's Day. You spend time with the kids. And then on Father's Day, she's like, hey, it's Father's Day. You should spend time with the kids. And I'm like, wait a second.

[Joe Saul-Sehy]

What's the double standard here? What is going on?

[JJ]

Where do you guys drop in on this? I mean, it's a little bit different because your kids are older. You don't see.

[Sherman]

Yeah, I want to spend time with my kids.

[JJ]

Yeah, you want to.

[Sherman]

I absolutely do.

[JJ]

I do, too, actually.

[Sherman]

You have to say that. They listen, they're in the next room.

[JJ]

We. So the boys have gotten into golf a little bit, and they're not, you know, they're working through it. They have some really good shots. They have some magically awful ones they need to work on pace of play. Like, they just do a lot of, like, Practice swings. And I'm like, just hit the ball.

[Sherman]

Alex and William, It'll be like that for the next 70 years.

[JJ]

Well, not pace of play. If they play, I mean, I just go and hit. Like, I don't. There's no warmup. But anyway, so this past week, we were playing. We played nine holes. About halfway through, they're getting frustrated with the fact that, you know, some shots are good, some shots are bad, and, you know, I'm just kind of drumming my fingers. Like, what are we. What are we doing, guys? Let's go. Come on.

[Julie Wainwright]

Quit.

[JJ]

Quit arguing. Hit the ball. And so I decided that they should play me for dish duty as a scramble.

[Sherman]

Ah, that's a good idea.

[JJ]

This was just reinvigorated their golf game because they were working together on a scramble against Dad.

[Sherman]

I like it.

[JJ]

So they scrambled and got a stroke. So there are four holes to play. They won the first one, we tied the second, and then they won the third hole. There was no way for me to win. And I said, well, would you like to play double or nothing?

[Sherman]

Oh, no, don't. You just. You completely just gut punched him, didn't you?

[JJ]

Well, they were like, wait, what does that mean? And so I explained. I said, well, it means that either I do twice as many dishes, or if I win, we're even. Steven, there's nobody wins or loses. That's the bet. I said, you guys talk about it. I'm going to the next tee box. So they were driving together in their cart, and so we get up there, and I said, what do you guys want to do? I said, yeah, yeah, yeah, let's do it. So we get both. We. You. You'll do dishes for us both twice. I go, yeah, if you win and you get a stroke. So you just have to beat me. You have to tie my score. First one tees off. It just shanks it, right? Like, okay, no problem. I got you, brother. Next one tees off. It's a little right. Then it's my turn. And the clouds parted. The wind started gusting from behind me, and for the first time all day, I hit a golf ball dead straight on the screws. With a 500 mile an hour wind off two sprinkler heads, a bird picked it up and carried it further.

[Joe Saul-Sehy]

It rolled down the cart path for.

[JJ]

It didn't hit the cart path. It was dead straight. It took one big hop onto the green, and I watched my kids melt as they're like, no. I did three putt, though, sadly, for a par, and they made a Six. So that was a valuable lesson that they learned, which was, take your money and run. When you're up at the casino, you have to leave.

[Joe Saul-Sehy]

If you got the Nvidia and it's way up, sell.

[JJ]

Sell your stock. So I'm going to do that again this Father's Day, I think, and see if I can Khan Matt us more money.

[Sherman]

It reminds me of a time I was golfing, I was solo, and I got paired up with three other people. They all knew him, knew each other. It was Jesus, Moses, and this other guy. Oh, no, they all knew each other. Moses gets up, and, I mean, he crushed the drive, but it went. Of course. We were on a really tall grass, like heather. Super tall. And he hits it into the tall grass, but he just raises his arms, and the grass just parts, and the ball just rolled forever. And he gets up pretty close to the green, and Jesus is like, great shot, Moses. I see what you did there. Then Jesus gets up, and he crushes one at the water. But what's the ball do when it gets to the water? It just, like, bounces right across like it was solid surface, just walked on water. And Moses is like, okay, all right. Yep, that's pretty good. And then the third guy gets up, and he really, like. He shanks one super high into the right, into the trees that were right next to the tee box. But a bird picks it up, carries it all the way over, drops it pretty close, but it didn't. Didn't roll to the cup. But then a squirrel comes along and just, like, nudges it in with his nose, and it goes in the cup for a hole in one. And Jesus goes, nice shot, Dad.