#192 David Segal: Yearly Planning, Daily Action

This episode discusses the intersections between personal growth and entrepreneurship, focusing on the importance of routine and psychological resilience in achieving long-term success.

1. Routine and Consistency: The importance of maintaining routines to manage stress and enhance productivity.
2. Psychological Resilience: Entrepreneurship requires enduring highs and lows, and managing one's psychology is crucial.
3. Mindfulness and Self-Care: Engaging in mindfulness and self-care practices can significantly impact mental health and business success.
4. Impact of Entrepreneurship on Personal Life: Entrepreneurship is not just a career choice but a lifestyle that deeply intertwines with personal growth and identity.
5. Learning from Failures: The journey of entrepreneurship is riddled with failures that provide critical lessons and opportunities for growth.

1: Introduction

A brief overview of the episode’s focus on yearly planning and daily action, with a special emphasis on the psychological aspects of entrepreneurship.

• Shane Parrish: "Welcome to The Knowledge Project, a podcast about mastering the best of what other people have already figured out."

2: Building and Exiting David’s Tea

Discussion on the founding, growth, and eventual exit from David’s Tea, reflecting on the emotional and professional challenges faced.

• David Segal: "The journey involved many ups and downs, and eventually stepping away was both a relief and a challenge."

3: Starting Firebelly Tea

Exploration of the motivations and differences in approach between David’s Tea and Firebelly Tea, focusing on product quality and customer experience.

• David Segal: "Firebelly Tea was about creating a product that I truly believed in, without the compromises of my previous venture."

4: The Psychological Demands of Entrepreneurship

Insights into the psychological resilience required in entrepreneurship, including managing stress and expectations.

• David Segal: "Managing your own psychology is a crucial part of entrepreneurship."

5: Personal Growth and Future Plans

Reflections on personal growth, future aspirations, and the continuous journey of learning and adapting.

• David Segal: "I am constantly learning and adapting, which is essential for personal growth and business success."

1. Establish a Routine: Start your day with a routine that includes exercise and mindfulness to set a positive tone.
2. Embrace Failure as a Lesson: View failures as opportunities to learn and grow rather than setbacks.
3. Maintain Psychological Resilience: Develop strategies to manage stress and maintain mental health.
4. Focus on Quality: Whether in products or personal habits, focus on quality over quantity.
5. Plan for the Long Term: Set long-term goals but focus on the daily actions needed to achieve them.

Working in a business and working on a business are two different things. Without the former, nothing gets done; without the latter, the wrong things get done. David Segal has a unique way of managing that tension, and this episode, he reveals all his business operating secrets and explains how he failed along the way.

Shane and Segal discuss what entrepreneurship really is, where motivation comes from, and what Segal learned building a $200 million tea business. Shane and David also dive deep into the dark side of success and the radical depression that can strike when you get a big payday, life and business lessons they learned from Warren Buffett, and the value of time management.

David Segal is the co-founder of Firebelly Tea. He’s also best known as “the David” of DAVIDsTEA. During his time at DAVIDsTEA, Segal grew the company from a single store to a $200 million retail giant. Segal left DAVIDsTEA in 2016 and started Mad Radish—a quick service restaurant concept. Mad Radish is all about providing healthy, gourmet fast foods. In 2021, Segal started Firebelly tea to create exceptional loose leaf teas tailored to modern living.

People

• Shane Parrish, David Segal

Companies

• David's Tea, Firebelly Tea

Books

• Mention of various books on entrepreneurship and psychology (not specified)

Guest Name(s):

• David Segal

Content Warnings:

• None

David Segal

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 when you had 6 hours of sleep and you're not feeling great and you're feeling sluggish.

And that's actually when you need to do it.

Shane Parrish

Welcome to the Knowledge project, a podcast about mastering the best of what other people have already figured out so you can apply their insights to your life. I'm your host, Shane Parrish. A quick favor to ask before we start. Most people listening on apple podcasts or Spotify haven't yet hit the follow button. If you can hit the follow button now, I would appreciate it.

The more people who follow the show, the better the guests we can get. Thank you and enjoy the conversation. If you'd like access to the episode before everyone else. My thoughts and reflections at the end of episodes, member only episodes, hand edited transcripts or you just want to support the show you love? Join at FS blog membership check out the show notes for a link today.

My guest is David Segal. David started David's tea and grew it to over 200 million in annual sales before stepping away. David and I first met the summer of 2020 on a lake and quickly realized we had a lot in common. We started running together a few times a week, chatting about business and life. Those runs helped me during COVID more than he could.

Now many people like to dream about what they would do if they didn't need the money, and for Dave, the answer was to start fire belly tea with his good friend Harley Finkelstein. However, as you'll hear, he's doing a few things differently than he did at David State. We discussed the lowest point in his life and how he overcame it, starting and growing a business to 200 million. The emptiness he felt after walking away from David's tea and then watching it flounder, starting fire bellied tea, and what he's doing differently, and so much more. Before I met Dave, I wasn't really a tea drinker.

I mean, I dabbled occasionally with tea bags. You find in grocery stores, but never really found it tasted that great. In fact, I remember telling him it always tasted a bit like there were some faint chemicals in it. And I remember where we were, we were written under a bridge and he stopped and he looked at me and he just sort of grabbed my shoulder and stopped me from running and he said, you've been drinking the wrong tea, my friend. And it turns out what I was tasting was a combination of poor quality tea preservatives and additives that are in most teas.

The next day, there was a slew of tea on my doorstep and I've been drinking it ever since. In fact, my kids and I now make a pot of fire bellies after dinner mint nearly every night as we wind down, not only does it help them sleep better, but it's a great ritual for us to connect and chat. A little bit about the day. You'll walk away from this conversation inspired by Dave's stories, learning a lot about the real messiness of running a business in the weeds and wanting to try some fireballing. To that end, Dave was kind enough to offer all fs listeners feel 15% off all orders at Firebelly.

Just go to firebellytea.com and use the discount code. Shane 15 it's time to listen and learn.

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Harley Finkelstein

I want to start with what's the biggest lesson you've learned over the past. Year and why, 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.

David Segal

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, 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. The podcast is called Big Shot, and they talk about the swings, the ups, the downs of their career. But it's in montages, right? 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 broaden my scope and my perspective and look at it over the course of time and really try and only make major evaluations when Im in a good place mentally and only on a longer period of time, maybe once a year, to take stock of where I am versus where I would like to be. Yeah. And be able to take a broader lens and not feel the lows as much as I sometimes do.

Or the highs. I mean, it's hard not to feel the highs, right? Cause they feel so good. So it's nice to celebrate, but you celebrate with the high five and then you go back to work. How do you learn how to do that, though?

Harley Finkelstein

Like managing your psychology? That's such an important journey for every entrepreneur, for every person. But nobody really teaches us how to go about doing that. 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.

David Segal

It's 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. Tea is this product that has been around 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.

And I like the connection tea gives me to history, and not only the feeling that it gives me a great green tea or a great herbal tea in the evening, but I think that's part of being able to manage. Your psychology is routines and rituals. I think another piece of it for me is mindfulness and meditation has played a big role in my life. I've been doing it now for well over five years. Uh, I do it consistently, and it really.

It makes a huge difference. It calms my nervous system down. It allows me to get a bit of distance. I mean, it's remarkable what ten minutes of breathing can do. Yeah.

And I exercise a lot and. And I try and take care of myself. Uh, and I try and have a good time, you know, life short. And. And I think it's important to celebrate, um, Friday nights.

I like to remind myself, uh, just how much I have and how lucky I am and really, really take in, really appreciate my life and take in all the good in my life. I think that's really important. When Monday comes around, it's like war, right? You're in the trenches, you're driving hard. You're driving with a sense of urgency.

I'm trying to build. I'm trying to build companies. My wife will always say, isn't there something good going on? And it's like, well, there is. Just the good comes on Friday night, when I'm in the moment and I'm trying to build, I need to focus on how to improve.

And so I become hyper critical of myself. I sort of let that sense of urgency take over and let the feeling of we're not doing enough set in. And then, within reason, try to temper that so that you don't come off too strong with your team around you and you don't end up trying to move something forward that, frankly, just needs time in order to progress. Sometimes that's the case, right? Sometimes the best action is no action.

But then Friday nights, it's really important, I think, to sit back, enjoy, smile, give your kids a kiss, think about how fortunate we are, and really appreciate. Your life, you step back and step away. I have a saying that you sort of reminded me of when you were talking, which is a lack of patience changes the outcome. And sometimes when you try to get something faster than it naturally should happen, you actually end up in a worse place. 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. Talk to me about the annual thing versus daily. How do you use that? You do action daily.

Harley Finkelstein

How do you set that and measure progress and consistency while keeping your eye on the annual timeframe? 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, in 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?

David Segal

I think I usually ask myself, without consciously doing this, two things. One, 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 really start to pound the table and get people moving. And there's a lot of those. 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 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, 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. So it's like daily. You want to focus on the micro things that move the needle, but totally, as you step back, you focus on the more macro stuff.

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 trust, but verify. Here's a great example.

Like what is Air Canada or 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. 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. 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. And those small transactions often require urgency. 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. I just loved it. I loved the product knowledge. I loved learning about the shoes.

But my sense of urgency in making sure every customer was helped before they walk out of the store. Now, I got paid on commission. I was 16 years old. I think I made $12 an hour at the time, and minimum wage was five. 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 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. Can you make somebody care, or do you hire people that naturally care?

I had a mentor that used to talk about this. He'd call it will versus skill. Sometimes they have skill, but they don't have the 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, right? You develop a love for what you do over time. So sometimes I think it is about patience. I don't know that anybody can teach you how to have a spark and a sense of urgency, but I do think you can cultivate someone's spark and their sense of urgency. But ultimately it's on the person themselves to really tap into what makes them get up in the morning and want to achieve.

Harley Finkelstein

You mentioned details. One of the commonalities I find between exceptional people who've done exceptional things is they're always in the weeds, and yet there's this sort of cultural backlash against being in the details, and everybody sort of wants to manage with abstraction. Right. Talk to me about learning about the details and being in the weeds and why that's important to you. 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.

David Segal

Having said that, it is a balance. One of the things I learned building David's tee was the difference between running a militia versus running an army. When you have a small company and you're running them, it's like a militia, right? 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 say, turn left, and everyone hears you.

The militias, there's five of you, right? Or ten 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. If you 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.

When you don't allow the people in 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. 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. Where did your drive come from? Like, what were you like as a kid? It seems very abnormal that a 16 year old at foot locker would be so driven and motivated. I 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 finally, my father's like, this is crazy. The kid's never gonna 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 his family, with our hoses out there, spraying the back lung. And sure enough, we have a skating rink, you know, and I was a bit like that as a kid. I mean, I wanted to work before I was allowed to work.

I had a paper route 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 to 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 on my face, and I was like, that's it. That's, 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. What were you like in school?

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, 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, and she brought out the best of me. By my fourth year, I became an honor student, and I started to work a lot harder. Is that because you wanted to impress her? I think if I wanted to hang out with her, I had to go to the library. So she was in the library.

So, yeah, I wanted to see her. I wanted to be with her. 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. So, you know, she mattered more to me than partying, so I ended up hanging out with her more often, and she brought out some better habits than me.

Harley Finkelstein

What did your kitchen smell like on, like, Friday nights? Growing up, I mean, I had a. Very regular upper middle class, middle class upbringing. My mom had a few different jobs, was a teacher. She taught deaf kids for a while.

David Segal

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 seven, last patient was at six. 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 a lot of steak. And I had a nice upbringing. I mean, I had a nice family around me, but entrepreneurship and business wasn't really that. 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 CEO's 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. Trey, once you learn more about your extended family and its history of entrepreneurship and making fortunes, losing fortunes, remaking them, did you feel like you fit in more? The way the stories, as I got older, the way the stories were told to me was like an episode of succession. My family built a business called peerless clothing, and it was filled with this one being mad at that one and not talking to this one and feeling slighted.

It was basically three brothers. The oldest one started it with the dad. The middle one came in with the elder one and was kind of the inside guy, the elder one, then, once he had made it, decided to go to Japan. And in those days when he went to Japan, it was like bon voyage, right? We're in the forties and fifties right now.

And so my grandfather got brought in. He was a tall salesman type guy, and the business was not doing well at that time, and they brought it back together. And peerless clothing for people listening was they manufacture. They're still around today. It's quite a large business, and they manufacture clothing for Pierre Cardin, Hugo Boss, and Calvin Klein.

And anyway, my grandfather ended up. The middle brother died, and there was a fight over shares and long story short, the son of my grandfather's eldest brother, who was adopted, came in and ran the business and actually did an incredible job with it and took it to a whole new level and was quite a successful businessman and philanthropy. And then from that, a cousin of mine, my dad's first cousin went off and started a company called Le Chateau, which for years he basically brought the Carnaby street look to Canada. So I became very close with him once I went to McGill. Didn't really know him that well before that.

And later in life, he ended up backing me in David's tea and we built it together. But, yeah, I sort of learned about these stories and I would say in my late teens, sort of as I was getting ready to go to McGill. And then I would hear stories about my great grandparents who came over with nothing and were peddlers in the countryside of Quebec. And one of my grandmothers father built up a big woolens business and then lost it all in the Great Depression, buying on margin like everybody else and then made it back. 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 kind of thing.

So I did grow up with these stories later in life, but my entrepreneurial 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. Talk to me about David's tea. Where did. So I'm guessing after university, you followed Emily to Boston.

No. So Emily didn't get into Boston till much later. We had a lot of ups and downs together. Emily didn't get into her PhD program at first and was gonna go do something else and then decided to wait and reapply 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 Proctor Gamble, I developed. So because I had worked, I worked in the buying department in Le Chateau 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. 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 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. 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 buy clothing, you actually do it in two steps.

First, you evaluate 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, but when it does get tried on it, it sells well. The fit's great, but the look may be off. It was a little bit ahead of its time. We were talking 2005, but when you think about e commerce businesses today, this is exactly what we do. We monitor 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. Everybody you tell that to. And I'm sure many of your listeners are like, oh, it sounds interesting.

Well, interesting is a great word in a classroom, but it's a terrible word in business. You want to hear things like, when can you deliver? And I was really good at getting these meetings with buyers at Macy's or Victoria's 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. It was a nice to have, not a must have, and it just wasn't going anywhere.

And I'm 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. 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 seventies 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, 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 in investments. If I'm going to be an investor, I should learn. The tea thing kind of clicked for me.

I always liked tea. Certainly growing up, I was never a coffee guy. And I remember being in a tea shop in Montreal off of St. Denis, which is this really cool street, sort of asian inspired teahouse. And we went in, and I started to think to myself, I'm like, wow, there's no size, no color like there is in fashion.

It doesn't go bad like a turkey sandwich. It's leaves in a cup. So the margins are good. You can operate out of small spaces, and we call anything you put in hot and cold water. That's not coffee tea in North America.

So it's like cooking, right? The combinations of what you can create are endless. This is a Warren Buffett business. We should do tea. And we sort of looked around for one to invest, and I got more and more into it.

I started to develop a love for the product. Finally, I think either I turn to my cousin or he turned to me, and I said, look, let's just do it ourselves. I'll build it and you'll back me. And it was a great combination of youth and experience. The way I like to describe it is, without him, I probably would have 1015 stores today, and without me, he'd have zero.

So it really worked out well. And away we went. We opened a store on Queen street, and it didn't work at first. I mean, it sort of worked, but it really took a bit of time. I remember the summer I got married, which is about a year.

We had four stores. It was about eight months after we started, a year after we started, and it wasn't going that great. I mean, we weren't doing well enough that summer for the business to survive, and I was really worried about it. But then we just kept getting better and better at it, and it finally caught and people started to get into it. And I think what we did that was very different is we took a commodity and we uncommoditized it.

When you think about tea, it's this incredible drink that's the second biggest drink in the world, next to water. It's just ironically, in North America, we're not that into it, but it's this timeless ritual that everyone has a tea story from when they were younger. Somewhere in their family, someone drank tea. And with David C. We created this sensory experience in the store where you come in and you're smelling tea and you're tasting tea and you're talking about tea and it became this very unique experience.

And I think that's one of the reasons it worked. And, yeah, it really grew from there. How many stores did you guys end up with? When I sold my stake in David's tea in 2016, we had 200 stores, about 200 million in sales, about $30 million in EBITDA. It was a pretty nice business.

Harley Finkelstein

How does it feel now to watch that flounder? Not great. And I actually tried to buy it back at one point with Bain Capital. Ive moved on. I mean, I wish Davids tea well.

David Segal

And im very excited about what were doing with firebelly tea, which is my new tea company. While I was developing Davids tea, I always had a private stash. Whats sold at David's tea were these heavily flavored teas and thats just what the market wanted. But my palate developed because I would drink it every day, all the time and I would travel these incredible tea regions and I would meet with our tea blenders and, and I'd learn kind of how to create an amazing tea and the right combinations of different ingredients. And when I left, I started to realize, wow, you know, I love tea.

I love creating teas and I love creating the products that go around with it. And I would curate these tea collections from my friends. I mean, Harley, who's the president of Shopify and a close friend, I got him really into tea because when I first met him, he's like, you know, I'm drinking way too much coffee. I'm not sleeping well. I get the jitters, I get headaches.

Im like, well, why arent you drinking green tea in the afternoon? Hes like, oh, I never thought of that. Im like, oh, my God, green tea is amazing. Hes like, wow, its kind of bitter, right? Im like, well, yeah, because most people drink the equivalent of folgers for coffee, right?

Coffee went through these phases where we went from first wave to second wave to third wave, and people got fancier and fancier in the types of coffee they drank. And tea in many ways. Hasnt. David's team made some headways and certainly had slightly better product. But I think the really good stuff is still new to most people.

And that's what fire belly has become about. It's in curating these collections for Harley and other ones of my friends. I brought some to you and got you into it a little bit. As we develop getting people into these amazing teas, and all of a sudden, Harley's drinking green tea in the afternoon. No more headaches, no more jitters, because the caffeine in tea is very different.

There's l theanine in tea as well. Whereas with coffee, you get that big spike and crash. You don't really get that in the same way with tea. You get more of a sustained energy. L theanine modulates the impact of the caffeine in your bloodstream, on your body, and it really creates a nice calm energy and a nice focus.

And then you have herbal teas in the evening that are fantastic. And whether it's you want help sleeping or with digestion, whether it's ginger. And so the teaspoon that we create with fire belly, we don't use any of these flavorings, which is kind of the secret in the tea business. If you go label hunting at the grocery store, everything has either natural flavor, artificial flavor, and it's not that it'll kill you, but a natural flavor just means it was derived from a plant or animal source. But it ends up in a laboratory where about 90% of what goes into these flavors are preservatives and additives that go unlisted on the label.

We have these all the time. They're not necessarily bad for you, but they create kind of a monotone flavor. It's like watermelon chewing gum. Right, right. You get that burst of flavor, but then it dissipates.

It's very similar with flavored teas when they're using flavorings. Whereas instead of using vanilla flavoring at fire belly, we use real Madagascar vanilla. We use really high quality ginger, really high quality turmeric. And it makes a difference in the quality of the tea. I think fire Belly became this brand where I got to create the teas I love and share my private stash with the world.

And then you can't put a Ferrari engine in a winnebago, so we had to create the accessories to go with it. And so we created a stop infusion travel mug. I mean, you think about accessories. It's all designed for coffee drinkers, but I wanted to put tea drinkers first. So we created this travel mug where you can stop and start the infusion with really high quality loose leaf tea.

You can make hotter iced tea. It's 100% leak proof. It's powder coated metal. I mean, I get obsessive about all these small details, so I'm having a lot of fun with it and building up my sort of chapter two, act two, and tea with fire belly. I never really drank tea until I met you.

Harley Finkelstein

And then now it's become, like, this nightly ritual with my kids, which is kind of weird when you think about it, right? Like, one of my kids favorite tea is after dinner mint that you guys make. And he just loves this. Like, he'll have four or five cups at night, you know, while he's doing homework, and he's sort of like, he'll make a teapot. Yeah, he's 13.

David Segal

My kids, too, they get into it, right? Cause there's so many different caffeine free teaspoons, so many different flavor profiles, whether it's a sweet ginger or a chocolate tea or a really nice peppermint eucalyptus tea, apple chamomile. There's so many different combinations. So kids can get into it, too. That's what drove me to create fire bellies that everyone.

I would show really high quality, loose leaf tea to and demonstrate how nice a tea ritual is, would continue on with it. I mean, they'd get into it, and I'd be like, wow, I want to share this with everyone. I really want it to be something special. I mean, this isn't something you can find at the grocery store, right? It's much higher quality tea than people are used to.

And I think, why not? Tea should have its time. It's so big in Europe and other places in the world. It's just North America that, for some reason is a bit late to the party. And I just think once they realize how amazing high quality tea is, it has its place in our daily ritual.

Harley Finkelstein

The world is completely different now than it was when you started David tea. Very much so, yes. So what are the differences you see in the tea space? What lessons can you take from David's tea? And where's it harder now and different to contrast it?

David Segal

When I started David's tea, there was no instagram, there was no shopify. You had server rooms. And if you want to build a website, you called a website guy. That's how we used to build websites. You found a friend of a friend who is usually a kid who knew how to build a website in HTML.

A physical retail store was much more about distribution than it was discovery. I mean, it was about both. But nowadays, you don't need a store to distribute, right? E commerce was a tiny, tiny percentage of the business back then. It's exploded on the scenes now.

So it was very different. I think the space is much more competitive now. There's a lot of products out there that claim lots and lots of benefits. But I think some of the fundamentals of building a business haven't changed. So everybody loves to talk about what's changing and disrupting, but I think it's also important to look at what doesn't change, and having a great quality product doesn't change.

And I like to put my energy into that. And one of the things I love about tea is that it's so timeless. Tea has been around for hundreds and hundreds of years and drank in cultures all over the world for different reasons. It has proven benefits versus some of these other products that come on the market, that make claims that have not been studied. It's obviously harder to compete with the fad du jour, but I want to build a 100 year company.

I want to build something that people can trust, and that isn't going to waver in some of the principles that it stands for. What we love about loose leaf tea is it's higher quality product. You get the whole leaf. You get to watch it expand. You get the full health benefits.

It becomes this pause in your day. And I think that's just, that's what we're about. We're about, we tend to attract people who are type a. I mean, they're not necessarily entrepreneurs, but they're entrepreneurial in what they do. I think it's for people who are on the go, who need a moment to themselves or a social moment with friends.

I mean, it's Tuesday night. You don't always want to have alcohol, right? Like, sometimes you just want to have a, hey, can I make you a tea? Like, have a great tea and a great conversation. So I don't think those principles changed in terms of David's tea.

I mean, David's tea was a fashion brand. It was about smell. Like people were discovering, wow, you can have tea with vanilla, and you can have tea with almond, and it turns pink in your cup. And there's one that's strawberry. And this was very new, right?

And it was all about, you know, smelling it, and it was just such a new phenomenon. We went from Earl Grey and mint and chamomile into all these plethora of flavors. And I think with fire belly, it's a little bit different. We're saying, look, we don't do things that you can only do with flavoring. Like we don't do peach tea because you can't make a peach tea without flavoring, but we do really high quality freeze dried berries.

And what has changed about business is there's more of an opportunity to take a niche and really get 1000 true fans with it. I think it's easier with modern day media to talk to niche audiences. And so we want to be really good at servicing a customer base who really cares about having an incredible team ritual, really high quality product, and really just focus on what we do best. And I think that's a little bit different than how it used to be. I think it's easier to find your audience at scale than it was.

You weren't able to do that in 2007. Right. In the same way, I think that really changes how you think about the. Business and you're in physical locations. Macy's and Erewhon.

We're in Erewhon, which is a really hot grocery store right now in LA. It's, you know, we don't want to be in some of the more mainstream grocers, but erewhon really is a special place. Yeah, we're in Bloomingdale's. We do some of our gift assortment in crate and barrel. Yeah.

And it's mostly direct to consumer. So why those places? Tea makes the perfect gift. Right. So we tend to perform well in, we took our best sellers and put it in Erewhon.

I think era one has a more discerning customer and appreciates really high quality loose leaf tea. So I think erawon works for us and we've been, you know, we've been one of the top performers in our category so far. And I think Bloomingdale's and crate, you know, they're gift. You go there for Christmas to buy Christmas gifts and t makes a great Christmas gift. And so all of these great gift boxes with our accessories and our teas together, and it sort of works really well there in November and December, when you think about it, you can give tea to anyone.

You can give it to your mother. You can give it romantically, you can give it to a coworker. It really does make a great gift. I mean, the message you're sending the person is, here's something that's good for your health and well being. Here's something that can be a break from your day, or it can be social with your family, your friends, your colleagues.

It's a funny thing. Everyone has tea in their cupboard, but it just sort of sits at the back and gathers dust. And that was one of the things with firebelly. We wanted to make sure that it was well designed. We originally put it in these boxes that are like books on a bookshelf, and we did that.

We want it to be on your counter front and center, and it should look good, too. And so we've approached it from that angle, but we haven't approached it as a fashion product. I mean, with David's tee, that was a big thing, right? Like, it's spring, summer, winter, fall. It's like our new fall collection.

Our new spring collection. It's pumpkin. This. Well, no, we don't really think about tea that way. Like, real tea drinkers drink tea every day.

It's fantastic. Fire belly is a brand for tea drinkers, for people that really love it, and that's what we're servicing. What failures have you had that you cherish the most up until this point? It's funny, I don't often think about my failures. They just become part of who I am as I go forward.

But if you're afraid to fail, forget it. Go get a job. Failure takes on many forms, right? There's failure in that. It just like I failed, it didn't work.

I was a failure. And that happened to me when I started that fitting room company right out of college. And it straight up did not work. I had to hang my head down and lick my wounds and move on. And as is often the case in life, you have to go down in order to go up a lot of the time.

And I had to do that in that case. And it humbles you, I think. And I wore that one in a big way, especially at a time in life where everybody's trying to flex in their advancement in their career as young professionals. Here I was with this major failure right out of the gate. And failure can also be in the form of it's taking too long, I think.

We often don't think of that as failure, but mad Radish, which is a healthy fast food concept I have in Canada, we had figured it out for the lunch market, and we were accelerating in five day a week office stores. And then the pandemic came, and we almost went out of business, and we were failing in a big way. And I had invested way more money than I thought I would have to, and it had taken far longer than I thought it would, but it wasn't working. And I almost stopped, and we almost said, you know what? Let's sell it for $0.10 on the dollar and move on.

But we didn't, and we stuck with it. And now it's in a much better place. And we got better at the dinner menu. We developed a two day part menu, so we got really good at the nuances of that business. We did that through failures.

We kept failing. We failed on menu development. We failed on real estate. We took bad stores. We figured out what not to do, to the point where here we are today.

I'm very fortunate. I have a couple of partners in that business, one of whom is the CEO of the company, who's doing an incredible job. I was the CEO of the business. And then when I started Fire belly, and I realized t is really where I wanted to go back to, he took over. He was our head of operations, and he's done an incredible job.

Now the business is starting to grow again, and we've become, I think, the number one player in Canada for healthy fast food. And I'm really excited about the growth there. But we failed. We failed and we failed and we failed and we failed until finally we started to succeed. It's a great expression, a story told by one of our guests on big shot.

His name is Peter Mays, an activist investor. He was Nelson Peltz's partner. He tells a story about going around and trying to market his first company and getting a valuation that was far below what they wanted. And they're yelling at the investment bankers. We just did this whole roadshow.

What do you mean it's not worth x? And the guy goes, kid, you can't make chicken salad out of chicken shit. And sometimes that's actually what you have to do. You have to make chicken salad out of chicken shit. And that takes time, and you have to fail.

You have to be honest about the fact that you have chicken shit right now and really work on somehow turning it into chicken salad. So I've had to do that a lot. I mean, and even David's tea, it was a success, but a big success. But then it faltered several times along the way. And then when I left, it fell apart.

I sold my stake in it in 2016, and today it's worth a fraction of what it was. And the market moved on and the company missed it. And it's not easy. Business is really hard. And that's why you have to be ready to keep showing up.

And you really have to love the journey of it more than the end result. Because if all you want is that moment where you make the big score, or that moment you think you're going to have, where you spike the ball and you have that big score, well, I actually went through one of the biggest depressions in my life. After I sold my steak in David's tea, I thought that's what I was playing for. I thought I was playing for this big success where the other side of the rainbow? And it was great.

I mean, I had financial independence for the first time in my life, but I lost my sense of purpose, and I had no plan. I didn't think about the day after David's tea. I was so busy trying to build it. And we actually don't talk about this a lot in entrepreneurship, which is the struggle is so difficult to get to a place where you're successful. But what happens once you're successful?

And what if you do sell your company? And now what? And how do you derive meaning in your life? I mean, you're not just going to go play shuffleboard when you're 35 years old. I went to a dark place in my life, and I didn't know what to do with myself.

And it took me a while to reinvent myself and sort of tap back into the kid I was that loved entrepreneurship and building businesses, and I had to tap back into that. And that was a journey on its own. And in many ways, not preparing for life after David's tea was a failure. Did you recognize that you were depressed? How?

Oh, yeah, I was really depressed. Like, I went through, I don't talk about this often, but I was in a really bad spot. And it was a weird thing. I felt guilty about it because, wow, what right do I have to be depressed? I just had the dream that everybody plays for, which is an exit in a major company and financial independence.

But I was. I was very upset. I had some health issues, and it's hard to know whether the health issues were from the depression or the stress of building it, or just what came first, the health issues of the depression. But no, I had to develop better habits in my lifestyle. I had to develop a better perspective on life.

There was a lot of stress. There was a fair amount of internal fighting in the company between my original partners, the private equity group. It wasn't an environment where everyone was just focused on the customer and adding value for the customer. And there was a bit too much internal conflict, which is one of the reasons I felt it was time for me to move on. And I think I never had a chance to process all that and deal with that.

And I had to really understand when it no longer becomes about the money, you really have to think about what you're doing and why you're doing it, you take away that factor that it allows you to drown out all the other things in life that are really important. Meaning and being able to really appreciate the journey. And I didn't really understand those pieces in my life early on. It just became a singular focus where, how can I build this and make money? What would you say to somebody who's depressed right now?

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.

I don't know where I heard this story, but I think it was a guy who had survived the internment camps during the war where they were being tortured. And he said that it was the people who lost hope that didn't make it. It was the people that had hope, but not expectations that did. Right. So they knew they'd get out of there, but they didn't have an expectation on when.

And I think depression is like that as well. You have to get up and go for that run, even though you don't want to do that. 20 minutes sit, breathing, exercise, even though you don't want to work on your eating habits or your rituals, whatever they may be. It's all kinds of different rituals in your life. It's important to develop.

I'm using the word ritual loosely here. Routines, habits, whatever you want to call them. When you're in a dark place, they're even more important. 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 when you had 6 hours of sleep and you're not feeling great and you're feeling sluggish. And that's actually when you need to do it. The doing is what matters.

Life. Life just is like that. And I learned that from my father, you know, I mean, he got up early and stayed late and put in the work. And there is no substitute for the work. Doesn't matter how smart you are.

You have to put in the work. It's so interesting. Cause the parallels between sort of depression and being successful at your job, your career, life, they map each other, right? Which is like, you have to do it when you don't feel like it. And that's when it matters the most.

Harley Finkelstein

And you sort of have to have that will, because everybody loses the battle with willpower. So the routines, the rituals, they carry you through when you don't feel like doing it, it's like, I don't feel like going on the peloton today, but I do it every day, so I have to get on and go and. Make every day day one. You know, we have a habit of beating ourselves up, right? Like, the idea of being compassionate with yourself is really important.

David Segal

You miss a day. So what? Like, in meditation? In meditation, it's, you know, come back to the breath. Come back to the breath.

And we call it rabbit holes. You go down a rabbit hole where you have these almost blackout moments where your mind just carries you in a thought. When you first start meditating. Most people, when they first start meditating, they do the same thing. They sit down for 20 minutes, but don't do that.

Sit down for three minutes or four minutes or five minutes. Build up. You're building a muscle. You're building that focus muscle. But when we have these blackout moments in meditation where our mind wanders and we don't even know where it goes, and then all of a sudden we come back and we're like, oh, yeah, I wasn't focused on my breathing.

Whatever visceral exercise I had, we have a tendency to beat ourselves up. You're like, oh, I can't believe I. You know, you do it mentally and we're human. You're going to make mistakes. Like, you don't have to always get it right.

You're allowed to slip up, but just keep restarting. There is no moment in life where everything's just perfect. Like, life is dynamic, it's not static. Right? You're always renegotiating with yourself, and it is an ever changing thing.

And I think it's just, how do you work on bringing the right attitudes into it each and every day? I want to go back to 2016. You get this fairly big payday. What are the lessons that you wish you knew then about money, that you know now? First of all, money doesn't buy meaning, number one, you have to.

Money can help facilitate a lot of things, but you have to know who you are and what you want. That's really, really important, and that has nothing to do with money. Buying nice things is going to be fleeting. I think we all know this intuitively, and yet so many people do this. And I'm not saying don't buy nice things, it's always nice to buy nice things.

But it's important to understand that in and of itself is not going to give you meaning. A really nice car, a nice watch, or a nice house or whatever. It's going to be cool for a minute. Eventually it's going to go away. I think I once heard this from a friend.

The secret to life is something to do, someone to love, and something to look forward to. Money can help facilitate parts of that. Especially, there's something to look forward to, but you have to tap in the deeper meaning on what gets you excited on an ongoing basis. For me, it's building businesses. But I wish coming out of that experience of making money and becoming financially independent, I wish I'd taken a little bit more time to think about how I wanted to do that and where I wanted to do that.

I think I was a bit too. I felt I needed to get back in the game very quickly. I think I set an artificial timeline. I think sometimes we set these artificial timelines with ourselves, and at least in my case, it was my ego. I felt I had to be back in or I was going to be a one hit wonder.

And I mean, all that's B's. I mean, there is no one way. There is no one story. I'm now in my early forties, and we love telling ourselves the stories of people that validate our narratives, right? Like, so I'm like, oh, Sam Walton didn't start until he was in his forties.

Or like, you know, Warren Buffett made most of his money after 55. I mean, all of these things are just ways of telling ourselves that we have more life ahead of us. And the truth is we do. And there is no one way. You can always find a story that validates your narrative.

I think in some ways, that's kind of healthy, now that I think about it. Now I think you want to continue to reinvent yourself and not think of yourself as too old or now I have these two businesses that are growing, and I'm like, oh, I need to grow them fast because I only have this many good years. I'm entering my prime. And it's like, well, are you? Who's to say?

There are endless stories of people that do it in their fifties, sixties, seventies, some in their eighties? I think all of that, everybody's unique. And I think it's really important to forget about if you're playing for validation from others or you're playing for external success, you're never going to have the full fulfillment that you get from your achievements in life. And I don't know that I've entirely overcome that external validation. I don't think I have, but I certainly work towards it and really focus a lot more on internal validation.

I think coming out of David's t, I wish I had. Coming out of a big financial score, but having not done a lot of the work to understand myself and what I really wanted out of life, I wish I had been more prepared for that. First thing I would have done, I would have gotten a nice office. I didn't have that. I stopped and I didn't have any.

I had nowhere to go in the mornings. I went from having this big office with 100 plus people who, with my name on the door, and I'd walk in and I was important, right? And then the next day, I'm out and I'm waking up, and now what? And no one's running up to me anymore, and I'm not in this nice office. So I think the first thing I would have done, I would have gotten a really nice office.

I think I would have consulted with a lot more people that had been through that experience of having sold their company. I wasn't very thoughtful about that. And I. In retrospect, I mean, I became. It took me a little longer, and I became more thoughtful about it over time.

But by the time I became more thoughtful about it, I'd already jumped into other things. And those, of course, take up your entire focus, because once you're in the game of building a business again, you're trying to manage the swings of the game, and you're trying to go on a run where you grow. And so you go right back into it, into the doing versus the reflecting. You mentioned Warren Buffett. I know you're a fan.

Harley Finkelstein

What are some of the lessons you've taken away from him over the years? The first one is, I wish I had this superpower. Here's a guy who can make very few decisions, but make them with so much conviction, and then live in Omaha, Nebraska, and go sit in a fishing boat while the world goes on around him. I mean, talk about being able to overcome the action bias. I just think that's incredible.

David Segal

I mean, a lot of things we're talking about here today where, how do you get to a place where you have internal validation and you kind of don't care what others think? I mean, very few of us can say that we don't care about what others think. I think he's one of them. He really is one of them. I first read about Warren Buffett at the start of David's tea.

I was telling you the story. I think it was buffetology. Actually, I think his daughter in law wrote it. So that was. I mean, we're going back now 20 years, right?

Since that time, I've seen him go through waves where the world thought he was a dinosaur, right? Like when he bought Kraft and when the tech was really booming, everybody's like, or bitcoin was super hot, right? Everyone's like, oh, this guy's a dinosaur. He's out. He doesn't know anything.

Well, turns out he's not. Then he turns around, he buys the japanese trading houses at $0.10 on the dollar, and he makes another brilliant move. And you're just like, wow, he's done it again. I mean, I think before 2008, it was another period in 2006, 2007 leading up to it, where he looked like a dinosaur, and then, bang, he's saving the financial world in America and making these investments in Goldman Sachs. So I think what I admire about the guy is we have all these sayings in life, like, play the long game or learn how to sit with something.

It's really hard to do those things. It's all easier said than done. I think he's managed to be able to do them. And I also. The other thing I admire about Warren Buffett is being able to express complex things in simple terms.

It's like the Mark Twain saying, I'm sorry I wrote you such a long letter, I didn't have the time to write you a short one. When I was going to McGill, I went into management, and I realized very early on that I didn't know how to write. I was a terrible writer. It's sort of a lost art form, and I wanted to learn how to write. So I went into english lit at McGill, and I ended up minoring in english lit.

It was serendipitous because I met my wife in english lit, but I also learned how to write. I wrote for the McGill daily newspaper, and I really wanted to turn what was a weakness for me into a strength, and I became an above average writer. I'm no Mark Twain, but I'd like to think I can write a decently persuasive email or letter, and I think that's a really important skill set. And where that comes in particularly helpful is how do you express a complex idea in simple terms? No one does this better than Warren Buffett.

I mean, you read his annual shareholder letters, and he does such a good job taking, I mean, something as complicated as the energy industry or the railroad business and distilling it into a few timeless principles. And he does this with investing as a whole. Right. He teaches us how to have a perspective on investment, on investing that will sustain you through a lifetime. I wish I had his patience.

I never will. It's just not who I am. I think one of the differentiating factors for him is how rarely he actually moves on something and makes decisions. He sits on things longer than most, and I think that's a rare quality. How do you fit everything in?

Harley Finkelstein

I mean, you have an incredible wife, you have three kids, two businesses that you're running. Yeah. And a podcast that's growing. A podcast that's growing. I think a couple of things.

David Segal

I think getting up early is really important. I don't really know many extremely successful people who don't get up early. I like to work out in the mornings. I like to turn my phone off at a certain point in the evening. And I know this is going to sound really weird, but I actually, I bought this thing that I can put my phone in that locks it.

It's like a little cubby for my phone. And I put it in now around 09:00 930, and it's locked. And of course, at first I was like, wow, what if my parents a bit older? What if something happens or I need it? And I said, well, you know, my wife has a phone, I have my computer.

It's not like there's other ways I can check if I need to, but this allows me from sort of. I used to go on social and just sort of numb out, and a half hour would go by and I'm like, what am I doing? I just wasted a half hour of my life numbing out on social with my kids. Can I be present reading my son Harry Potter, who's seven years old and just starting to get into that. Can I take one of my daughters out for a tea and be able to just listen to them talk about their science fair or their gymnastics or whatever it is they're into?

It doesn't take much. I'm not religious at all, but I think there's enormous wisdom in the concept of the Sabbath. I think it's just an incredible concept. Right? What is that?

So the Sabbath is a Jewish. It's called Shabbat. It's in Judaism. It's this idea of from Friday night sundown to Saturday night sundown, you don't work. Now, what does that mean?

Today? I've sort of evolved it to my own personal, like I say, I'm not religious, but I think there are principles in there that are very. That have helped me a lot. So I still will work on a Saturday morning sometimes, but I won't. I won't.

I like to come at it with a different mindset. For some reason I found a way to take the edge off on the Friday night to Saturday night. And I think of that as my relaxed time. And if I'm working, it'll be more reading or taking notes or reflective emails on my laptop. I don't, you know, there's working in the business and working on the business.

I like to take my weekends if I'm going to work, to work on the business and not in the business. I really make sure I take time for my kids and my wife on the weekends. I mean, I make it a point to go out with my wife for a date night at least once a week. Usually on the weekends we go for dinner together. We take a fair amount of trips.

I think that's also really important. I like to get away. But yeah, I sort of have started to bring a different mindset from my Friday night to Saturday night. And then Sunday you start to ramp up again, right? Like you sort of gear up for the battle.

But Monday to Friday it's intense. Like I'm an intense guy. I just am. There's no way to. For better, for worse is who I am.

And I go at it hard and I wear my heart on my sleeve and I work very, very hard. I'm present with my family during the week but for very short periods of time. And I'm certainly more present on the weekends and on holidays. Like I was saying, there's no substitute for the work. You have to operate with a certain level of intensity in order to get things done.

And I work late into the night. I work up until about eight or 09:00. I'll usually either read a bit or watch a bit of tv with my wife, read to one of my kids before bed and go to bed and try and get as much sleep so I can get up and do it all over again. Do you think that's sort of the biggest missed opportunity that people have is when they stay up late? Because you go to bed early, you wake up early.

Harley Finkelstein

But it's that like, you know, I don't know, 930 to 1130, you don't really get anything done. You end up scrolling, watching tv. But if you get up, if you. Go to bed at 930 and you get up at five, you're like ready to go, you're in thousand percent. I think that's the biggest, least productive, most dangerous time for our mental state of the day.

David Segal

And usually I find it's, it's also the time of day where I'm the most worried about my future, about the business I'm usually the most down on. I'm in a depressive state and I'm sort of like, ah, it's not working. Things aren't going my well, I wish this, I wish that. And I'm sort of down on myself. And it's important to be like more and more I try and distance myself and be able to be the observer rather than the participant in that and being like, okay, well, you're just tired.

Like, you're just tired. You know, with kids, when you're like, okay, you're tired. It's no different with adults, right? Like, you're just tired. Like, go to bed.

Call it. It's over, days over. You know, tomorrow's another day, go to bed. I feel that what's missing most in life right now? That's a tough question.

I cheated before this interview and looked at your notes and I saw that question and I wasn't sure how to answer it and I'm still not. I think it's a really difficult question to answer. I think the answer is nothing. There are lots of things that I want, but there are few things that I truly need that I don't have right now. I think what's missing is just more.

More life, more embracing the journey, more being able to take it all in without feeling less than like a failure. More being able to just appreciate all the good that's in life versus constantly perseverating on what's difficult or missing or bad. Life is short and it should be celebrated, it should be elevated. And I think there are lots of things I want to do and accomplish. I definitely sit down once a year and I write out goals and I write out one year goals and three year goals and ten year goals.

But then I kind of like to say to myself, and let's say I achieve none of them because you always have that sort of fear. Like, what if it doesn't work? What if I'm not that good at this? And what if I can't? And so what?

I got three healthy kids, I got a great marriage, I've made enough money, I've. And so what? And I know that sitting here, it's easy for me to say that a lot, but it's all relative, right? You have to remember that it's all relative. Like there's always somebody who has more and there's always somebody who has less.

And that's true no matter where you are. But the truth is, I was just as happy in that base room apartment in Montreal as I am now. So much has changed in my life. But at the same time, the real changes, the real things that brought true happiness, were the personal developments, were my ability to connect with my wife on a deeper level, where my ability to truly enjoy and appreciate my kids. I think we're all kind of playing for that no regret, old age rocking chair moment.

At least I sort of use that as a yardstick. Be like, well, is this going to matter in my rocking chair? And, of course, life has many twists and turns, and who's to say you'll ever be in a rocking chair? I mean, I think it's just more the sentiment than the reality, but I think that thinking about the question, what's missing in your life? The answer is always perspective.

You have to decide what narrative you want to live. You don't get to choose. A lot of things in life are completely out of your control, but how you think about things and the narrative that you go through life with is in your control. Everybody could say, well, your pain's not as big as my pain, or your hardships aren't as big as my hardships, but it's all relative. I mean, pain is pain, and hardship is hardship.

And, yes, some are worse than others, but by and large, we all have things that we need to overcome. And I just think that, really, it's doing the hard work to try. And how can you continue to sharpen your perspective and your narratives? You can celebrate life and get the most out of it. I like that.

Harley Finkelstein

Cause you're choosing where to focus, right? You choose your focus. You really do. And that's something. It needs to be practiced.

David Segal

It's not something you can't just tomorrow. I think it's hard to wake up tomorrow and be like, I'm gonna have a positive mindset about everything. Well, you're not. If you've gone through your life having a negative mindset about everything, you're not gonna be able to do that in one day and probably not in one year and probably not in five years, frankly. But how do you take one step forward in that journey towards having a better perspective and being able to enjoy life more and celebrate all the good that's in your life and not just focus on all the things that are not what you want to be?

Harley Finkelstein

We always end with the same question, I guess. Think of it as the rocking chair question. The rocking chair question, which is, what is success? For you, what do you want to be sitting there looking back on? And you'd be like, that's success.

David Segal

When I was a little boy, my father used to say to me, he'd say, david, you're like an eight cylinder engine operating on two cylinders. And I didn't really know what he meant by that. I didn't know the world. I didn't know it was out there. I didn't know all the possibilities.

But the more I go through life, the more I realize that for me is very important. I don't want to ever look back and feel like I didn't use all eight cylinders. And I think that applies to everybody. I don't want to feel that I didn't tap into my full potential. I don't know what that is right now.

I can't tell you. We all have a certain level that we're going to reach. Not everyone's Michael Jordan, and not everyone's going to be the Warren Buffett or the CEO or the president or whatever. And I don't think that matters. I actually think what's far more important is did I self actualize all eight cylinders that I was able to self actualize?

Did I tap into my full engine? Hopefully one day on my rocking chair, as the rocking chair question, I'm able to say I did that. I didn't shortchange myself. I didn't not show up for myself. Thank you so much.

Harley Finkelstein

This has been awesome. Thanks, Shane. This is great. Appreciate it. Thanks for having me.

Shane Parrish

Recently I've started to record my reflections and thoughts about the interview. After the interview, I sit down, highlight the key moments that stood out for me, and I also talk about other connections to episodes and sort of what's got me pondering that I maybe haven't quite figured out. This is available to supporting members of the Knowledge project. You can go to FS blog membership, check out the show notes for a link, and you can sign up today. And my reflections will just be available in your private podcast feed.

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