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David Segal

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2024-04-16
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2024-04-16
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  1. Sitting in this basement apartment while most of my friends are starting to accelerate their careers and my wife was my girlfriend at the time was like, okay, enough. Like, you know, you don't make any income. You need a job. So I decided to call it quits, which is with a heavy heart. And I approached my dad's cousin who had started Le Chateau, this clothing business that had become very big in Canada. And he was looking to take a step back from that business. He was in his 70s at the time. And he said, look, I'll start a little private equity shop and you'll come help me. And I said, great. And I think he paid me like $40,000. I mean, a nominal salary. And I figured you sort of fake it till you make it. I bought a book. I bought what Warren Buffett looks for an investments. You know, if I'm going to be an investor, I should learn. The tea thing kind of clicked for me. You know, I always liked tea, certainly growing up.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  2. But when it does try get tried on it, it sells. Well, you know, the fit's great, but the look may be off. It was a little bit ahead of its time. We were talking 2005, right? But when you think about e-commerce businesses today, this is exactly what we do, right? We've monitored traffic and conversion. And then we had ways of capturing the fitting room being this point of interaction with the customer. You can capture feedback. Interesting idea, right? Everybody you tell that to, and I'm sure many of your listeners are like, oh, it sounds interesting. Well, like interesting is a great word in a classroom, but it's a terrible word in business. You know, you want to hear things like when can you deliver? And we would, I was really good at getting these meetings with buyers at Macy's or Victoria Secret or The Gap. I'd write these handwritten letters to Les Wexner of limited brands, and I'd get a response and we'd have all kinds of meetings, but it didn't progress enough. You know, it was nice to have, not a must-have. And it just wasn't going anywhere. And I'm.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  3. You're deciding what to buy in a season. You're hoping it sells, but you're deciding in advance what you think people are going to like. So often what large clothing companies will do is they'll test. So if you have a hundred store company, let's say, you'll buy for five or ten stores and see how it goes there before you take the inventory risk of buying for the rest of the stores. And you'd have these buying meetings where they're evaluating these tests and they'd evaluate whether something sold or it didn't sell. But they had no idea why it was selling or why it wasn't. Everybody would speculate on that. So I developed a system for the fitting rooms. And the idea being when you try on, when you buy clothing, you actually do it in two steps. First, you evaluate the look of something on your, sorry, the look of something on the rack, then you evaluate the fit of that item on your body, right? What we thought is, hey, if we can capture the conversion rate at the fitting room, we'll be able to tell you if something's being tried on a lot, but it's not converting out of the fitting room, you might want to check the fit. And vice versa, if something's not being tried on a lot.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  4. No. So Emily didn't get into Boston until much later. We had a lot of ups and downs together. Emily didn't get into her PhD program at first and was going to go do something else and then decided to wait and reapply it to McGill PhD and then got in. So we were in Montreal after we both graduated McGill. We were living together in a tiny basement apartment in Montreal. And I started a concept called Fitting Room Central. While most of my friends went off to Goldman Sachs or Procter Gamble, I developed, so because I had worked, I worked in the buying department at Le Ch ⁇ teau for a few summers and I sold, as I was telling you, running shoes and clothing a little bit as well. So I understood that business, certainly at a base level. And I developed a concept called Fitting Room Central because when buyers would buy clothing, remember when you're in clothing or anything with inventory, your biggest risk is your inventory buy, right?

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  5. The way the stories as I got older, the way the stories were told to me was like an episode of succession. You know, my family built a business called peerless clothing. And one of my grandmother's father built up a big woollen's business and then lost it all in the Great Depression buying on margin like everybody else and then made it back. And my grandmother used to tell stories about going to school in a carriage and then having to quit school the next day and walk to the factory, you know, kind of thing. So I did grow up with these stories later in life. But my entrepreneur drive came in before that. I think those stories just validated it for me and had me even more excited for my entrepreneurial career ahead.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  6. And business wasn't really that, you know, it was interesting. I had this extended family in Montreal who had been very successful in business and I had this rich history that I really wasn't in touch with at the time. Education was certainly strongly encouraged, but I didn't have access to CEOs and to type A business people in my life early in my life. I started to meet them later in my life. Once I went to Montreal and went to McGill and started to meet some of my extended family.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  7. I mean, I had a very regular upper middle class, middle class upbringing. My mom had a few different jobs. She was a teacher. She taught deaf kids for a while. Then she became an artist. My dad was a psychologist and started working at the hospitals and then had his own private practice. He worked very, very hard. I certainly learned my work ethic from my dad. He was up at 545 every day. First patient was at 7. Last patient was at 6. Never took a lunch break. We always had Friday nights weren't dramatically different than Wednesday nights. Because my dad didn't really travel for business, we always had family dinners. And they were really nice growing up. I mean, I was very lucky I had my grandparents in my life. They would, I guess, come over on Friday nights, and we'd often barbecue a lot of steak. And this is before red meat, we knew red meat wasn't so great for you. And so big steak family. We do love steak. And I had a nice upring. Yeah. I mean, I had a nice family around me, but entrepreneurs.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  8. I think if I wanted to hang out with her, I had to go to the library. So, you know, I mean, she was in the library. So, yeah, I mean, I wanted to see her. I wanted to be with her. So I kind of just followed her. And she didn't, you know, she didn't, I used to go out a lot and probably party too much, but she wasn't into that. you know, she mattered more to me than party. So I ended up hanging out with her more often and she brought out some better habits to me.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  9. I didn't take school all that seriously until later on. I mean, I knew I had to do well enough to get into a good university. But for me, university, I was excited to go socialize and have a great time. It wasn't until I met my wife where I really got it together. I mean, I got into a great program. I went to McGill University, but she studied hard. I mean, she became a neuropsychologist Harvard educated. You know, she brought out the best of me by my fourth year. I became an honor student and I started to work a lot harder.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  10. Allowed to work. I had a paper rooted at a very young age. I went on and I worked at Wendy's. I was the fry guy. I think the breaking point for me was I had to take out the garbage and I was a small little 14 year old. So you had to throw it over the fence, right, to get it into the bin. They had the guard for the animals and sort of fence around the garbage bins. And I couldn't quite get it over the fence. And so it sort of teetered on the top of the wall and then kind of came down to my face. And I was like, that's it. I'm out of here. And I think I was probably the youngest person they hired at athletes world, which is like the foot locker. I wrote my resumes. I banged on a lot of doors. And that was just who I was.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  11. Loved it. I loved working from a very, very young age. I was a bit, my wife says this about my son, and I think I was the same way. I was a man of action with no plan. I remember I really wanted a skating rink in our backyard. We had like this tiny little backyard. And my parents are like, no. So I was really stubborn. I'd go and I'd start taking little, you know, like the sour cream container. I'd wash it out and put water in it and start dumping it on the lawn and dumping it on the lawn. And my parents are watching me do this. And they're thinking, what is he doing? But I kept doing it and I kept doing it. And for hours on end, I'm dumping one little sour cream container worth of water on the back lawn. And my finally, my father's like, this is crazy. The kid's never going to build a rink this way. And, you know, but then they started helping me. And then my brother started helping. And then here we are as this family with our hoses out there spraying the back lung. And sure enough, we have skating rink, you know, and I was a bit like that as a kid. I mean, I wanted to work before I was.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  12. As a leader, you want to have your finger on the pulse and understand what's going on at the lowest level of your company where customers are interacting with your team or your products, but you also don't want to micromanage to the point where the people who you've empowered to do the job aren't able to do it and be celebrated for their own successes or learn from their own failures.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  13. Don't have the right processes and procedures. So, I think what you stand for as a company should never change. But how you do things as a company should never stop changing. And I do think as a company scales, it's really important to understand how to put in place the right processes and procedures, not to stifle creativity or to stifle the people. You want to empower the people on the front lines and make sure that they can still make independent decisions. I mean, we've all experienced as a customer. There's nothing worse than hearing, I'm sorry, that's our policy. You know, when you don't allow the people on the front to think for themselves and they become robotic about how they deal with people, that's oftentimes the beginning of the end. But you do want to have processes and procedures to be able to facilitate the flow of information to and from the front lines effectively so that you are able to connect to the weeds without sort of jumping in and not allowing people to spread their wings and fly. And I think it's a delicate balance, right?

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  14. Well, I mean, it goes back to what we were just talking about, which is, you never want to have ivory tower syndrome, where you run a business and you're not connected to your customers, where you're sitting in an ivory tower somewhere issuing decrees. Having said that, it is a balance. One of the things I learned building David's tea was the difference between running a militia versus running an army. When you have a small company and you're running, it's like a militia, right? you know, you got five stores and you want to run a sale or you want to do some kind of marketing campaign or whatever it is that you're trying, whatever initiative that you're taking on. And you have a meeting and you say, okay, let's do it. And it's super easy because, you know, you say turn left and everyone hears you. The malicious, there's five of you, right? Or 10 of you or whatever. And everybody turns left. But when the company grows, you become like an army. And when you say turn left, you get broken telephone.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  15. A mentor that used to talk about this, he called it will versus skill. Sometimes they have skill, but they don't have a will. And sometimes it's vice versa. You get people who really care and work really, really hard but can't really move the needle because they just don't have the skill. You can teach skill more than you can will. I do believe that you caring about your work is something that no one can teach you what to do. But I think sometimes you develop the bug for it.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  16. The people on the front lines operating with urgency to add value to the customer and do that over and over again. And I think that's where the urgency really plays in is sort of creating that culture where people care about their work and care about the customers that they're dealing with enough to service them quickly and efficiently.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  17. But really, that's what it is. I mean, it's a series of small transactions that add up, but you need to continually get good at those small transactions. Those small transactions often require urgency. You know, I used to sell running shoes in high school. I loved it. I worked at a company called Athletes World, which is the equivalent of Foot Locker. And I just loved it. I love the product knowledge. I love learning about the shoes. My sense of urgency in making sure every customer was helped before they walk out of the store. Now I got paid on commission and I was 16 years old and I think I made $12 an hour at the time and minimum wage was like five. So I thought I was rolling in the dough, right? But I operated with urgency. There was no customer that left the store without me talking to them. I was all over it. And I outsold everyone. I was more into it. I cared about it more. I spoke to more customers in a day than they would. But that's what a business is. It's how do you get...

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  18. Tot 100%, right? I mean, any successful entrepreneur will tell you this, you got to be in the details. I mean, over time as the business grows, you develop a team that you trust to be in the details. But even then, it's Trespa Verify. Here's a great example. Like what is Air Canada, Delta Airlines or American Airlines? It's not the CEO. Nobody thinks about the CEO when they think of these airlines. When people say, oh, that airline's the worst, right? I mean, no one really likes airlines. Well, what are they really saying to you? They're not saying, most of them couldn't even tell you who the CEO is or the management team are. They're saying that that individual person that I dealt with at the customer service counter, was not nice to me or didn't leave me with a great feeling or didn't help me with what I needed helped in that moment. You know, the business happens at the transactional level, any business. That's where it happens, where the money is exchanged for the goods. And I think often the bigger the company gets, we kind of forget that.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  19. You to offer better service, better product, become better at what you do. Those are the small things, right? And those things, I think you do want to have an incredible sense of urgency around. The bigger things like, you know, should we be selling this product or that product or presenting the brand this way or that way? I think those things you want to analyze more on a monthly basis or quarterly basis or in some cases an annual basis.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  20. Is this something that I can recover from easily? Meaning, if I'm wrong about this, what's the impact of it? Two, what's the risk of doing nothing and waiting for more information? More often than not, the answer is, wait and get more information, certainly on big decisions like to go in a different direction with the product, to deviate in a big way from your marketing efforts. Usually there it's try and get more information, try and get more information, try and get more information. Things like you're out of stock and you got to pressure a supplier to ship it faster, that's where the sense of urgency comes in and you're really, you know, you start to pound the table and get people moving. And there's a lot of those, right? There's a lot of little decisions in a day where if we can do a little bit more to ship that extra order, handle that last customer service request, those add up. So those small things where a sense of urgency allows you.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  21. When you're building a business, the amount of decisions you have to make is coming at you a mile a minute. It can be like trying to drink through a fire hose. I think you develop an intuitive sense of it. I don't know that I consciously sit there and think of every decision and ask myself, is this a monthly decision, a daily decision, a weekly decision? I think I usually ask myself without consciously doing this two things. One,

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  22. Absolutely. I mean, certainly in businesses that I'm building, I like to truly measure progress on an annual basis. I think that's the time to do it. Did you get better this year versus last year? Did the business grow this year versus last year? You may not be at the place you want to be, but did you progress? And I've been in situations where I had to say, no, you didn't progress. And I was in a business early in my career where I had to wave the white flag and say, I failed.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  23. No, we don't talk about that at all, certainly not in school, right? Look, I mean, it's really hard to do. I'd love to sit here and tell you that I've mastered it. And I'd like to think I've gotten better at it. I think taking care of yourself matters. One of the reasons I love tea so much is I think it plays into that lifestyle. It's, you know, in a world where there's so many highlight reels and different products that will make you think you're going to walk through walls and promise you the moon. T is this product that has been around, is as old as the hills. I mean, it's been part of humanity for so long. It's drank in regions of the world where people live the longest. It's been studied for decades, not years, but decades by some of the top institutions in the world.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  24. Feel the lows as much as I sometimes do, or the highs. I mean, it's hard not to feel the highs, right? Because they feel so good. So it's nice to celebrate. But you celebrate with the high five and then you go back to work.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  25. About the swings, the ups, the downs of their career, but it's in montages, right? Like it's like watching a Hollywood movie, something that is actually two minutes is actually five to ten years. And it feels like a lot longer when you're in it living it. And so I really, over the past year, have really put a lot of emphasis in trying to manage my own psychology and get better at when I have a crappy day or a crappy week or a crappy month, not having an action bias or making big decisions or just being able to kind of broaden my scope and my perspective and look at it over the course of time and really try and only make major evaluations when I'm in a good place mentally and only on a more longer period of time, maybe once a year to sort of take stock of where I am versus where I would like to be. Yeah, and be able to take a broader lens and not

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  26. Really, that entrepreneurship is in many ways a personal journey disguised as a business pursuit. And what I mean by that is so much of it is managing your own psychology. Everybody talks about playing the long game, right? But it's easier said than done. There are so many swings to the game when you're building businesses. The lows are so low. The highs are so high as well. And it's learning how to be able to tolerate those lows. So I started this podcast with Harley Finkelstein's president of Shopify, a really good friend of both of ours. We interview these, we're both Jewish, and we interview these old Jewish guys who don't have a social media presence. All of them are over 70, and they've had these incredible careers and had enormous impact, not just building businesses and becoming incredibly successful, but also in giving back to their communities and their philanthropic efforts, a podcast called Big Shot. And they talk.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT

  27. There is no shortcut for the work, period. There's no magic pill, there's no magic elixir. It's about habits. You have to do things even when you don't want to do them. You have to get up and go for that run, even though you don't want to. I mean, it's really easy when you've had 10 hours of sleep and the sun is shining and it's warm outside. It's really easy to go for that run or put on that smile or whatever it is. That's where it's easy. Where it's hard is it's when it, you know, you had six hours of sleep and you're not feeling great and you're feeling sluggish. And that's actually when you need to do it.

    2024-04-16 · The Knowledge Project with Shane Parrish · David Segal: Building a $200m Business · IDENTIFIED FROM THE TRANSCRIPT