“$100M dollar brands are being built for boring products” - Harley Finkelstein of Shopify

Summary

Podcast Title: My First Million
Host/Author: Hubspot Media
Episode: “$100M Dollar Brands Are Being Built for Boring Products” featuring Harley Finkelstein of Shopify
Release Date: June 12, 2025

---

Introduction

In this episode of My First Million, hosts Sam Parr and Shaan Puri engage in a lively and insightful discussion with Harley Finkelstein, the Chief Operating Officer of Shopify. The conversation delves into the intriguing concept of building multimillion-dollar brands around seemingly mundane or "boring" products. Harley shares compelling stories, business strategies, and personal insights that highlight how redefining and reimagining everyday items can lead to monumental success.

---

Reimagining Everyday Products: The Touchland Story

Timestamp: [00:32] - [03:20]

Harley kicks off the conversation with a fascinating case study on Touchland, a company that transformed the humble hand sanitizer into a luxury item. Originally distributing hand sanitizer in Africa to combat sanitation issues, the founder envisioned making the product "sexy."

• Key Points:

  • Traditional hand sanitizers like Purell are purely utilitarian with unpleasant smells and basic packaging.
  • Touchland raised $67,000 on Kickstarter, leading to a first-year sales of approximately $1 million.
  • The onset of COVID-19 exponentially increased demand, culminating in an acquisition offer of $880 million by 2025.
  • Touchland’s success underscores the potential of elevating basic products through aesthetic and sensory enhancements, effectively creating a new market category.

• Notable Quote:

  • Harley Finkelstein: “How do you take an ugly thing or just a commodity utilitarian product, apply high fashion to it, and create your own category.” ([03:00])

---

From Boring to Sexy: Trends in Modern Branding

Timestamp: [03:20] - [10:19]

The hosts and Harley explore the broader trend of transforming mundane products into desirable commodities. Sean Evans highlights recent examples like Dyson's Pencil Vac, which garnered millions of views for a seemingly ordinary vacuum cleaner.

• Key Points:

  • Dyson Pencil Vac: Demonstrated how a standard product can gain massive attention through innovative design and effective media storytelling.
  • Ember Mug: A Shopify success story that adds functionality (temperature control) to a common item (mug), showcasing the power of incremental innovation.
  • Investor Insights: Harley discusses the importance of founders who obsess over their products, similar to Cat Cole of AG1, who grew her business by expanding the market rather than just claiming a larger piece of the existing market.

• Notable Quotes:

  • Sean Evans: “Millions of views on this demo for a vacuum cleaner. It's incredible how media storytelling can elevate a basic product.” ([03:42])
  • Harley Finkelstein: “People gift this hand sanitizer because it’s now a desirable item, unlike the purely utilitarian Purell.” ([03:53])

---

Shopify's Evolution and Strategic Focus

Timestamp: [10:19] - [25:24]

Harley and Sean delve into Shopify's growth trajectory, company phases, and strategic decisions that have shaped its path to becoming a $100 billion company.

• Key Points:

  • Company Phases:
    • Swiss Army Knife Phase (0-150 employees): Early-stage where team members wear multiple hats.
    • Triple Threat Phase (Post-Series A/B): Employees specialize while maintaining versatility.
    • Spiky Objects Phase (8,000 employees): Focus on individual strengths and high-impact roles.
  • Recalibration Post-COVID:
    • Shopify faced challenges during the pandemic surge and subsequent market downturn.
    • The company reduced its workforce from 14,000 to 8,000 to streamline operations and focus on core missions.
  • Founder-Led Leadership:
    • Emphasis on CEO Toby’s technical expertise, strategic intuition, and ability to spot and nurture talent.
    • Importance of having a leadership team that aligns with the company's vision and mission to foster growth and innovation.

• Notable Quotes:

  • Sean Evans: “We went public at an early stage because we thought it would be the best way to be independent longer term.” ([34:00])
  • Harley Finkelstein: “When you add a simple friction on hiring, like substantiating why AI can't do a job, you see incredible results.” ([50:37])

---

The Power of Founder-Led Companies and Culture

Timestamp: [16:26] - [31:30]

The discussion highlights the unique advantages of founder-led companies, using Shopify as a prime example. Sean emphasizes the irreplaceable value of passion, personality, and unwavering commitment from founders.

• Key Points:

  • Founder-Led Dynamics:
    • Leaders like Toby and Sean bring personal passion and commitment that are difficult to replicate.
    • Toby’s deep technical knowledge and strategic foresight drive Shopify’s continuous innovation.
  • Cultural Impact:
    • Shopify’s mission to "increase the amount of entrepreneurs on the planet" attracts like-minded individuals who are themselves entrepreneurs at heart.
    • The company culture prioritizes personal growth, high expectations, and relentless pursuit of excellence.
  • Leadership Styles:
    • Toby’s assertive and decisive nature (Enneagram Type 8) complements Sean’s driven and ambitious personality (Enneagram Type 3), fostering a balanced and dynamic leadership team.

• Notable Quotes:

  • Sean Evans: “Shopify's mission is very simple: increase the amount of entrepreneurs on the planet.” ([19:58])
  • Harley Finkelstein: “Knowing your team’s Enneagram types can be an effective tool for enhancing team dynamics and productivity.” ([30:09])

---

Navigating Market Challenges and Remaining Independent

Timestamp: [34:00] - [37:57]

Harley and Sean discuss Shopify’s strategic decisions to remain independent and avoid acquisition, focusing on long-term stability and mission alignment.

• Key Points:

  • Avoiding Acquisition Offers:
    • Shopify conscientiously avoided engaging with corporate development teams to maintain independence.
    • The decision to go public early was rooted in a desire to control the company's destiny without external interference.
  • Financial Strategies:
    • Shopify executed a small secondary sale during its Series B to secure personal financial stability for key team members.
    • Emphasis on protecting family and personal finances to ensure peace of mind and focus on the company's growth.

• Notable Quotes:

  • Sean Evans: “We wanted to build a 100-year independent company and knew acquisition offers could distract us from that goal.” ([34:00])
  • Harley Finkelstein: “Reinvesting profits by buying Shopify stock has compounded my earnings effectively.” ([57:30])

---

Embracing Technology and AI: Shopify’s Forward-Thinking Approach

Timestamp: [47:05] - [50:37]

The conversation shifts to Shopify’s integration of Artificial Intelligence and how the company leverages AI to enhance operations and decision-making.

• Key Points:

  • AI Integration:
    • Shopify emphasizes reflexive use of AI, making it an inherent part of daily operations rather than an ancillary tool.
    • Implementation of friction systems, such as requiring justification for hiring positions that AI could potentially fill.
  • Practical Applications:
    • Sean uses ChatGPT to analyze personal health data and refine business communication strategies.
    • AI assists in preparing for earnings calls by aggregating and presenting key data points effectively.
  • Future Outlook:
    • Shopify aims to be ubiquitous in commerce, expanding into platforms like Roblox, Pinterest, and potentially ChatGPT, ensuring merchants can sell wherever consumers are present.

• Notable Quotes:

  • Sean Evans: “Shopify runs some of the largest flash sales on the planet, enabling massive throughput like 30,000 transactions a minute.” ([43:43])
  • Harley Finkelstein: “Creating friction in hiring processes pushes employees to recognize where AI can replace human roles.” ([50:37])

---

Personal Insights and Health Practices of Leaders

Timestamp: [51:02] - [59:07]

Harley invites Sean to share his personal health and longevity practices, offering a glimpse into the disciplined lifestyle that complements Shopify’s high-performance culture.

• Key Points:

  • Longevity Practices:
    • Sean engages in annual comprehensive health scans with Prenova to monitor potential health risks like cancer and heart disease.
    • Incorporates biohacking and longevity protocols to maintain optimal health and performance.
  • Mental and Physical Challenges:
    • Participates in physically demanding activities like the 29029 program to push personal limits and maintain physical fitness.
    • Uses experiences and challenges to enhance personal growth and resilience, mirroring the company’s ethos.
  • Investment in Health Technology:
    • Sean and his wife invested in Prenova, reflecting a belief in the transformative potential of health technologies.

• Notable Quotes:

  • Sean Evans: “My life’s work gets to be more amplified today than it did 10 years ago because of Shopify’s scale.” ([39:15])
  • Sam Parr: “You’re worth over $134 billion company, yet you remain incredibly relatable.” ([55:37])

---

Conclusion: The Relatable Billionaire

The episode wraps up with reflections on Sean’s relatability despite Shopify’s immense success. Both hosts and Harley express admiration for Sean’s ability to remain grounded and personable, even as he oversees a company valued at over $130 billion.

• Key Points:

  • Relatability:
    • Sean’s approachability and down-to-earth nature make him a relatable figure despite his high-profile position.
    • The blend of personal anecdotes and business insights creates a narrative that resonates with listeners.
  • Continuous Growth:
    • Emphasis on personal and professional development as ongoing processes, regardless of the company’s size or valuation.
    • Encouragement for entrepreneurs to embrace adaptability and relentless pursuit of improvement.

• Notable Quotes:

  • Sean Evans: “There is no magic number. It’s just different problems at different scales.” ([38:31])
  • Sam Parr: “If you could achieve my approachability to market cap ratio, you’re winning.” ([56:59])

---

Key Takeaways

1. Transforming Commodities: Elevating basic products through design and sensory enhancements can create new market categories and drive significant revenue growth.
2. Founder-Led Growth: Passionate and visionary leadership is crucial for scaling companies while maintaining mission focus and fostering innovation.
3. Strategic Independence: Maintaining independence through early public offerings and avoiding acquisition distractions can ensure long-term stability and alignment with company goals.
4. AI Integration: Reflexive and strategic use of AI can enhance operational efficiency, decision-making, and overall business performance.
5. Personal Discipline: Leaders’ personal health and growth practices contribute to their effectiveness and the company’s success, highlighting the importance of holistic development.

---

Final Thoughts

This episode provides a comprehensive look into how Shopify, under the leadership of Harley Finkelstein and inspired by Sean Evans’ insights, navigates the complexities of scaling a billion-dollar company. By reimagining everyday products, maintaining strategic independence, and embracing cutting-edge technologies, Shopify exemplifies the potential of building extraordinary brands from seemingly ordinary foundations. Listeners gain valuable lessons on entrepreneurship, leadership, and the relentless pursuit of excellence.

Transcript

[Harley Finkelstein]

This is serious podcasting over here, Sean.

[Sean Evans]

The last time I did this, actually, I literally pulled up the date of it. It was in 2020, I think you were in like a wife beater. And then you went to the bathroom and I heard you flush the toilet. I'm serious, dude. That's how far we've come here.

[Harley Finkelstein]

Hey, we haven't come that far. These things that still might be. It might happen today I feel like.

[Sean Evans]

I can rule the world. I know I could be what I want to. I put my all in it. Like, no days off on a road. Let's travel.

[Harley Finkelstein]

I have a Shopify crazy business story for you guys. Go to your Internet browser real quick and go to touchland.com. harley, you might know Touchland.

[Sean Evans]

Oh, yeah, of course. I, I, in fact, I've given out them as like at events, but their.

[Sam Parr]

Headline doesn't make sense. It's sensory essentials that bring delight to everyday moments of care. I is that.

[Sean Evans]

It's hand sanitizer perfume.

[Harley Finkelstein]

It's hand sanitizer. So here, check this out. This story is pretty crazy. This person starts out, she's distributing, like, hand sanitizer in Africa where, you know, like, sanitation, super important. People get really sick because, you know, they don't have clean water to be doing, blah, blah, blah. And she gets this idea, like, what if I made hand sanitizer sexy? Because at the time, Purell, it was all like, Purell. Exactly. And if you, if you think about Purell, Sam, what does it smell like?

[Sam Parr]

Alcohol. It's like something you get at the hospital or a teacher from a teacher.

[Sean Evans]

Exactly. Horrible smell.

[Harley Finkelstein]

It smells like tequila. The form factor is not like, nothing you, nothing to brag about, nothing to show off. It was a very pure utility product. And what she did was she just reimagined it basically as a luxury product. So she took hand sanitizer. She was like, I'm make it smell good. I'm going to make it look good. I don't know if you've seen the, like, the cases of it. It's basically like, clear.

[Sean Evans]

It's beautiful. It's like this like, sort of like almost Jony, I've designed like case.

[Harley Finkelstein]

Exactly, exactly, exactly. It's if, if Apple decided to like, go into the hand sanitizer market.

[Sean Evans]

Collaborations, right? Like hello Kitty Disney. I mean, this is like a whole different level of, of, of of vision around hand sanitizer.

[Harley Finkelstein]

So she, she comes up with this idea. She goes on Kickstarter and she raises like $67,000. She's like, okay, great. $67,000. I could do a first run first year. I think she does like a million dollars in sales. Covid happens and obviously people care about hand sanitizer way more during COVID Business just explodes recently. This is now 2025. It was just acquired for $880 million. This hand sanitizer company. And I love this story, it says.

[Sam Parr]

It was going to do this year is going to do 130 million in revenue and $55 million in EBITDA.

[Sean Evans]

Wow.

[Harley Finkelstein]

Exactly. And credible. And they're on Shopify. There you go. There's your plug.

[Sam Parr]

Well, thank you.

[Sean Evans]

Thank you for plugging.

[Harley Finkelstein]

Dude, isn't this a crazy story? And how cool is this? Basically this, this concept of like how do you take an ugly thing or like just a commodity utilitarian product, but then apply like high fashion to it, apply luxury to it and create your own category. You know, it sells for more. It's the only hand sanitizer people gift to each other. Like you were saying, you gift it. My wife saw it and she's like, oh, I just got that as a gift for like our kids teacher on their last day of school. You would never like gift Purell to somebody unless you're trying to tell them something.

[Sean Evans]

I have a. You know, one of the cool. So we have a few million stores on Shopify. We're about 12% of all like us e commerce right now. One of the things that I'm seeing a lot of right now are these what I think would be considered to be fairly. You know, this is going to sound pejorative, but it's not like boring products becoming very sexy. And then I don't know if you guys saw this but like literally a week ago Dyson came out with this thing called the Pencil Vac. Have you guys seen this?

[Sam Parr]

Yeah.

[Sean Evans]

Anyways, like so like Dyson like the, the guy, the man, the founder, he actually did it like this press conference. It's on YouTube now. I just checked.

[Sam Parr]

He's amazing. Have you guys.

[Sean Evans]

Totally amazing.

[Harley Finkelstein]

Isn't it like a seven minute demo and he just came and dropped the mic.

[Sean Evans]

I think it's even left. I think it's like five minutes. But exactly, but, but there's like millions of views on this demo for a fucking vacuum cleaner. And actually what I thought about like one, he. He's been. Dyson's not a new company. They've been around for a very long time. But like this idea that he took something fairly boring made it way better and now he's able to Actually leverage modern media like YouTube to actually story. I bet a bunch of people like are actually going to buy their first Dyson product because of this video they never did before.

[Sam Parr]

Have you guys ever read about him? Sean, have you read about James Dyson dude?

[Harley Finkelstein]

You and David Sana won't stop talking about James Dyson dude.

[Sam Parr]

Like I, I started reading his book. He's just like the man, but he's basically, it sounds ridiculous. He's Steve Jobs of vacuum. He was Steve Jobs before Steve Jobs. But he was like, he's like this type of person where he's like the inside wiring needs to be beautiful. He's like that type of guy. But he took, I, I, I'm really interested in this idea of people who take non serious things. Very serious. So vacuum, hand dryers, whatever. And I think it's so freaking cool. And he is like that type of guy where he was like building the first prototype for like two or three years to the point where he was, I think he went bank bankrupt. But he still kind of kept at it.

[Sean Evans]

Amazing. But you could sort of look across a bunch of different, like I'm having my coffee now, like my Ember mug. Right. Like this idea of adding a small heater to a mug I think is like, seems kind of boring. Ember is a great Shopify store. So I've been following them since pretty much day one. I mean that's a huge company now, both in wholesale but also consumer.

[Sam Parr]

That's one of those ideas that I.

[Harley Finkelstein]

Thought that just go ahead and log in and just start reading out all the numbers for these brands.

[Sean Evans]

Yeah, I'm not going to do anything like that. But what I will say there's, you know, actually let me, let me show you. I'm going to give me one second. You guys know my best friend David Siegel. I think you've had him on the show. Founder of David's Tea Made. You know, took his company public.

[Harley Finkelstein]

He's awesome.

[Sean Evans]

Many hundred millions of dollars. Him and I have this like tea business on the side. We started during the pandemic called Fire Belly Tea. Anyways, like we tinker like you guys do on weekends, we have this idea. It's literally, I'm showing you a prototype right here. You can kind of see it. It is literally like our way. We think that Duraflame needs to be disrupted.

[Sam Parr]

That's a great idea.

[Sean Evans]

So like we talked about the time.

[Harley Finkelstein]

You'Re on the podcast.

[Sean Evans]

Exactly. So we had this idea in 2020 and actually so now David and I have, we have A working prototype. It's actually. You can read it. It's literally made from Canadian softwood. It's 100% kiln dried. We have branding, it's called flint, which we think is a cool name for it. But you look across all these different categories of things that most of us as consumers take for granted, and there's always this, like, 10x version of it. Like, my wife's really into. She could hate me saying this. She's really into karaoke. If you've ever gone and tried to buy a karaoke machine, there are companies that rent them to you because they're so big and clunky. Like, someone should go and, like, disrupt the karaoke machine business. Like, that, to me, is such a brilliant idea. Or, you know, tools, like, you move into a new house and you kind of need, like, you know, random tools. Most of these tool companies you buy, like at, you know, Home Depot, they're clunky, don't look good. There's actually a couple, like, beautifully designed, almost. Almost like the touchland version of tools selling on Shopify. People misunderstand TAM to their detriment. Total addressable market. Everyone kind of looks at TAM as being this thing which is like, what is the. Like, there's. There's a pie and I'm going to take a bigger piece.

[Sam Parr]

Like, it's a stat. It's a static number.

[Sean Evans]

Yeah, it's. It's very much like zero sum. And funny enough, you know, Sequoia has said this publicly, so I think I could say it now, but, like, the reason Sequoia did Invest in Shopify 15, 16 years ago was they looked at the Tam of retail SMBs on the planet and they effectively forecasted if Shopify would have a meaningful percentage of that market, how big of a company we could be. What they missed was that. That we're actually growing the pie itself. Right. There's like this positive sum that someone who's starting, you know, I don't know the person behind Touchland, Sean, but. But presumably, like, this person didn't necessarily like what she wasn't in, or he wasn't in this industry previously. Maybe it wasn't even entrepreneur.

[Sam Parr]

But that's the story you told yourself when you were doing it. Because when you're doing it, I mean, you got.

[Sean Evans]

No, you can't. That's the. You almost cannot do it. You actually have to almost imagine, like, you know, let's just use Flynn for a second. By the way, this is not for sale yet. Like, this is just a prototype. So you can't go buy it. But let's just like you. What you would do for Flint is you'd say, okay, what is the. What are the products on the market? The biggest one is Duraflame. How much does Duraflame sell a year?

[Sam Parr]

What's the answer of that?

[Sean Evans]

You know, I think it's something. I think it's like, we. Last time we chat was like half a billion dollars, and it was like Home Depot, Lowe's, these sort of home hardware stores. But then one of the things David and I were thinking about is, like, why are these not sold in convenience stores? Right? Like, why do I have to go to Home Depot for it? Why? If I'm picking up, like my weekend beer at a bodega or a 7 11, I should also pick my. My Flint as well. So what you. You have to almost do as an entrepreneur is you really have to kind of like, broaden out the horizon of, like, what is the potential? Cat Cole and I were just speaking last week. Cat Cole, who's the CEO of AG1. They're doing $600 million a year with AG1. With one single skew. There is no way Chris is the founder of AG1. There's no way that Chris thought about that. Like, you know, like, basically, they didn't just grow their. Their piece of the pie. They could. They grew the piece of in, like, Infinitely. And I think that's. Those are the best entrepreneurs for me.

[Harley Finkelstein]

All right, this episode is brought to you by HubSpot. They're doing a big conference. This is their big one they do called Inbound. They have a ton of great speakers that are coming to San Francisco September 3rd to September 5th. And it's got a pretty incredible lineup. They have comedians like Amy Poehler. They have Dario from Anthropic Dwarkesh, Sean Evans from Hot Ones. And if you're somebody who's in marketing or sales or AI and you just want to know what's going on, what's coming next, it's a great event to go to. And, hey, guess what? I'm going to be there. You can go to inbound.com register to get your ticket to Inbound 2025 again, September 3rd through 5th in San Francisco. Hope to see you there.

[Sam Parr]

Have you guys heard? Sean, did you ever meet Eric Ryan? I think he spoke at the Hustlecon that you spoke at.

[Harley Finkelstein]

I didn't meet him, but I. No, you never invited me to speak at Hustlecon. I was just an attendee. But I did attend the I Also.

[Sean Evans]

Was invited to speak at hustlecon just to say the thing. Yeah.

[Harley Finkelstein]

And we've actually decided to create our own called super hustlecon. People who actually hustle harder than hustlecon.

[Sean Evans]

Yeah.

[Sam Parr]

Instead of just the opposite.

[Harley Finkelstein]

But, yeah, I remember him speaking, and he was brilliant. So for people who don't know Eric Ryan, he did what Method soap. So he basically went into a boring soap category and made it sexy and made it, like, kept ingredients, you understand, on the back of the bottle. That was like the big trend.

[Sam Parr]

But the bottle was, like, pretty.

[Harley Finkelstein]

The bottle was pretty. And the. And the photography was pretty. Like they would do like a photo shoot instead of it being like, you know, those like, pharmaceutical commercials where they show a cartoon germ and he's getting sprayed. It was like two really hot people who are like, kind of like dating, but they haven't really defined their relationship yet, but they're cleaning up their house together. And like, that's what the. That was the. The photography on the website.

[Sean Evans]

Moyes did that too. Right? Moyes did it with. With Native and sold for $100 million to. To Proctor Gamble.

[Sam Parr]

Yes. Eric actually did it with Olivitamins. He also did it with a Welly band aids. And he has a new thing that he's doing it with, but I don't know what the new thing is.

[Sean Evans]

I mean, I have, like, you look at. Just shopping. You look at ritual riches, vitamins or seed, which is probiotics. There's a company that I think is really cool. They're called Prose P R O S E. They do personalized shampoo based on hair type. They're doing about 100 million. This is public information. They put it out there. $100 million in annual revenue. 80% of his recurring customers. So you basically, like, send them a follicle of hair, they analyze and they send you a shampoo specific for what you need. I think, like that personalization stuff for shampoo even, obviously, like, I don't know if you guys take supplements. I take like eight a day. I wish. You know, I can basically just take one pill that has exactly what I need specifically for me.

[Sam Parr]

Do those eight a day actually do anything?

[Sean Evans]

It's a little bit of, you know, correlation versus causation. My. All of my lipids are getting better and I think there's definitely some correlation to it. Although as part of my taking all these supplements, I'm also working out more and I'm eating much better and I'm drinking far less, you know, wine with. With on weekends. And so I can't necessarily draw a direct, you know, causality to it, but certainly I do think that. And, and honestly, it's not that big of an inconvenience. If it helps me by 5% or 10%, I'll do it. I'm also, I do every. Every year for my birthday, I do something called Prenova. Do you guys know Prenova?

[Sam Parr]

Yeah.

[Harley Finkelstein]

Yeah.

[Sean Evans]

I've been doing it since I was. For last six years. Every. My birthday in November, every year go.

[Harley Finkelstein]

To New York for a pretty bad birthday one year. You gotta be careful.

[Sean Evans]

I mean, that's the, the issue. The issue with that is obviously false false positives, which I have just decided. I think entrepreneurs and founders tend to be on. On this side of the. Of the equation, which is I prefer a false positive than a false negative.

[Sam Parr]

Right. Have you. Maybe you could answer this? You're actually the only person I've asked this publicly, but I've never got a good answer. How can you be a billionaire today and be unhealthy? Like, how can you be a fat billionaire today?

[Sean Evans]

I would get rid of the billionaire. I think if you are. If forget the billionaire thing for a second because I don't think that you don't need to be a billionaire to do that.

[Sam Parr]

Do you know any fat billionaires?

[Sean Evans]

I do, but I don't want to say anyone's name. Of course, you probably know them also, but I. Maybe, maybe they're the thyroid issue. I do believe that if you have the means and you can have, you know, if you can have like house, you know, housekeepers, for example, or you can have a chef at home. It's like you have a chef at home. No one's going to their chef and saying, make me super unhealthy food. Usually if you hire a chef, you say, I want to eat really well. Here's what I really like. So there's almost no excuse. Same with a personal trainer. It is very difficult to go to the gym. It is much easier to go to, you know, the gym if you have a trainer waiting for you that you're paying for you or someone showing up at your house. So I do think that is easier for you to be in better shape if you have means.

[Harley Finkelstein]

See, this is why I'm an outlier. I defy all the rules. I have a personal trainer who comes to my house. I'll find a way to. The will finds a way.

[Sean Evans]

But Sean, it's bullshit.

[Harley Finkelstein]

I want to doordash something. I'll door. I'll find a way.

[Sean Evans]

So if you didn't have the trainer come to the house. You'd be in weight. I suspect you'd be way worse off than you.

[Sam Parr]

Yeah. And also, you have gotten way healthier over the last half years.

[Sean Evans]

That's right, yeah. You know, when I had my first child, Bailey is now. My daughter's 8. When I had my first child. So Dave Siegel again, bring it up again. Like, Dave's a couple years older than me. He's had kids before I did. He basically said to me when I was having Bailey, he's like, look, if you can afford to have a nanny. He actually described, articulated as. He said, it's gonna be a marriage saver. And I didn't really understand what it meant. And what he meant was like, just everything, everything is easier as a new parent at home. I was, you know, shoplay was already publicly traded. I work 70 hours a week. He's like, just, if you can afford a nanny, you should do this. And I didn't really know what he meant by the whole, it's a marriage saver. In hindsight, I now do because, like, some of the stresses that I think some people have, you just. They don't go away. They're just less. You lessen them when you have certain, like, like luxuries in your life. And I, I don't. I do. I mean, I grew up without money, so I didn't grow up in that. In that world. I don't take that for granted. But I do see how it gets these, these things, These things get easier.

[Sam Parr]

I heard an interesting story about. Actually last week. I was with a person I'm not going to name, but he's like a. He's a billionaire and he's an. He's a big time investor. And he was telling stories about how he. We were talking about Shopify. I was actually talking about how I met with. Met with you. And I was like, man, Harley's so charismatic. Like, it totally got me bought into Shopify even more. And he was saying, he's like, yeah, man, I've met with Harley a bunch of times. I know him well. I've met with Toby a bunch of times. He goes, and I've actually met with Stripe a bunch of times, the Collison Brothers. And they're an amazing company. And he was like, I think they're roughly worth the same right now. But he was like, I think Shopify is going to be worth 10 times more than Stripe. And I was like, why? And he said, whenever I'm with the Cowson Brothers, we Talk all about like interesting philosophical things and like what their like hobbies are and things like that. And whenever I'm with Toby, the only thing he ever talks to me about is Shopify. That's all he ever wants to talk about. He won't. He will only talk about Shopify. And because of that, I think that obsession, even when your company is worth $150 billion or whatever it is that still comes into play, it's not just market factors or the market forces is.

[Sean Evans]

This is the beauty of this founder led thing. I mean I, you know, I think the Collinson brothers obviously are this great example of founder led as well. They're obviously private, so you don't know the exact valuation of it. But I do think that this, this era of founder led companies, people that just really give a shit, there's no way to replicate that or to emulate the give a shit.

[Sam Parr]

And I don't want to like, I actually wanted to spend some of the time episode where I was like, actually Harley, I like I know you a bit now but like Toby is like, he's still mysterious to me because I've never met him but he seems like, like I think he has this one quote where he goes, my wife says I'm an immigrant to the human condition.

[Sean Evans]

Yeah, that sounds, that, that seems stupid. I mean and to his credit because he is so self aware, he truly like he incredibly self aware. He knows what he's really good at. I mean that's. If you think about Shopify. I think I said this at Sam when we were meeting but like you think of the phases of companies. Like at the beginning of the first phase of a company, everyone needs to be a Swiss army knife. Like everyone do everything. And then the second phase, it's like more like what I call like triple threat phase where like every.

[Sam Parr]

Is there like a. Could you put a threshold onto that? Like a number of people or something?

[Sean Evans]

Yeah, I would say like for us it was like zero to, I don't know, Dunbar's number. You know that concept, Dunbar's number 50 or 150. Yeah, 150. Something like that. Which is like it comes from tribal times where that's how many people any human can remember at any one given time. So I would say like 0 to like 150 or so. It's like that, you know, Swiss army knife in those days at Shopify I did bd, I did sales support partnership, I built the App Store and partnerships program. I was also the lawyer. I mean I was a general counsel. I Wasn't really a good lawyer. I'd only practiced for a few months, but, like, Better Call Saul, yeah, I did. I didn't have a. We didn't have a CFO at the time or anything like that. So it's like Swiss army knife time. And then I think eventually you can almost market for us around, like, the Series A or Series B, where now, like, we're more people. People can sort of slot into the right roles. Meaning, like, you don't do one thing, but you do a couple things real quite, quite well. That was sort of. I was chief operating officer, and so I looked after a couple big organizations. We built a sales organization. We began to think about different eras of product post pandemic. So like 20, 21, 22. A couple things had to change for us. One is we were bloated. We had like 14,000 people. That didn't work. We brought it down to what we are now, which is around 8,000 people. And we quite like our size right now. We had a couple businesses that were not the right business for us to be in. One of them was shipping and fulfillment. We ended up selling at the Flex port. So we began to think about, like, side quests and main quests. Like, what are our side quests? Let's get rid of them. Let's focus on main quests. But the third thing that happened sort of in this new phase of Shopify, this new shape of Shopify is these, like, spiky objects. And what that really meant was we basically brought in a new, new team, new leadership team. And part of that process was Toby and I sort of thinking about, like, what are the things that we think we. We truly should be spending our time on, meaning the highest value for Shopify. And that meant that, like, we kind of rearranged the company not necessarily around these, like, traditional roles of, like, you do this and. But rather, like, based on our strengths. And as part of that, you know, Toby's not on the earnings calls anymore because it just. I got that. I can do that. I think I can do that at a. At a. At a really great level. I think I can eventually be world class. Those earnings calls, I'm going to focus on that, and Toby is going to run product for Shopify. That has been ultimately one of the greatest transitions. I think this is my 16th year at Shopify. It's Toby's 20th, and we've been public now for about a decade. But you can get there right away. You have to almost go through these phases in order to figure out what your spiky object is.

[Harley Finkelstein]

That's pretty cool. It also, it's pretty rare. I think if you look at how many CEOs are the best storyteller in their company, it's actually not most, but they don't want to give that up. And so I think even in there, you didn't even mention it. But there's a sort of almost like a very telling thing that he had. No. Didn't have the ego to say no. I need to be the front man. Also, I need to be the lead singer, even though I'm actually the best drummer.

[Sean Evans]

So Toby refers to me as the lead singer of the band. Like, I think a lot of companies throw around this idea of mission. Shopify's mission is very simple. Like, increase the amount of entrepreneurs on the planet. That's it. And we increase it by. By adding more entrepreneurs to Shopify who otherwise were aspiring previously.

[Sam Parr]

Dude, how do you hire people if that's your mission? That's a hard thing to like. Like all your employees would be fucking quitting.

[Sean Evans]

Well, actually, the best part is we end up hiring mostly entrepreneurs. People that have had some. That entrepreneurship in some way has deeply affected their life. For me, my. My. My. My grandparents are Holocaust survivors. They. After the Holocaust, they went to Hungary in the 50s. Hungary got really bad. Hungarian revolution happened. Canada let in 40,000 Hungarian immigrants in 1956. My grandfather came here with my father and his siblings. They came to Canada. My grandfather ended up selling eggs at a farmer's market his whole life. That egg stall, it's called Le Capitaine, still stands today. It's like 5km from where I'm standing right now. So entrepreneurship for me is deeply personal because it allowed my family to survive and also create the life that allows me to be here. My version of that is when I moved. I grew up in South Florida. I moved to Montreal to go to McGill when I was 17 in 2001, and my dad was no longer in our lives. I had to support myself and my mom and my sisters. And so I started a T shirt company. That T shirt company would eventually become an online T shirt company. And I would become one of the first merchants to use Shopify. That's kind of how I got here. But. And Toby comes to it in a very different way. He's an immigrant, lives in Germany, meets someone, a wonderful woman who becomes his wife named Fiona. He moves to Canada, can't get a job as new immigrant, wants to start a snowboard shop and finds it incredibly difficult to do so, writes a piece of code to sell these snowboards which would then become Shopify.

[Harley Finkelstein]

You know, our buddy George Mack has this great phrase where he says people only remember you're weird. Meaning any behavior that's standard that you do might be very useful, but it's not very memorable. And so, you know, Sam was asking about Toby just now and you know, I think like he said, he's a bit of a mysterious character. He's not somebody who's out there doing a bunch of podcasts and public things. I'm curious, what are some stories of his weird like, you know, what's a behavior or a thing that he does that's non standard?

[Sean Evans]

There are a couple things that I think define, you know, his leadership really well at Shopify. One fundamentally is that he spends a lot of his time using like all the newest tech constantly. He's constantly reading the newest white paper on a new LLM that just came out like this. And I don't think that's uncommon. I think you'd see that with Patrick or Zuck. But there is a category of these like super technical founders that did not exist historically. At least if they did, they weren't running hundred billion dollar or trillion dollar companies. Toby's in this group of people that are super technical that know more about the, the, the code base than anyone else on the planet. The other thing that I think is, is important is one of the things he does every year is basically, you know, during Christmas break he spends his time running effectively the priorities for the company. And January 1st, every single year, I don't know, for the last decade or so, the whole company gets an email and it's incredibly specific direction of like, what are we going to build this year? And it's not based on necessarily like, you know, servit. It's based on his deep intuition of how the product needs to evolve. And in some cases, you know, it's, it's, you know, Shopify runs some of the largest flash sales on the planet like for supreme or Taylor Swift or these, these massive, you know, crazy throughput that 30,000 transactions a minute type stuff. So sometimes it's like, you know, we have to be able to like to, to have this type of throughput and other times it's look, the future of retail is not going to be just online, it's going to be everywhere. And Shopify has to make it super easy to sell across every surface area. I announced two weeks ago we're doing it with Roblox inside of like basically the Roblox universe. That now we're embedding commerce in into there as well. Toby didn't say go do like Roblox. What he did say was make sure that everywhere where consumers are spending their time, there is a way for our existing merchants to easily turn on that channel. And it turns out like in something like Roblox, I forget what the DA use are but like it's, it's ridiculous. I think there's like 700 million monthly users in the Metaverse. I think the largest chunk of those are on are in Roblox. It's like 100, $100 billion industry today. It's going to be like 930 billion in 10 by 2030, I think. So we're like effect. So that's the type of stuff that he does is that he, he doesn't necessarily like some CEOs will go and talk to customers. He does that also. But ultimately what he's I think incredibly good at is the intuition on that. The second thing is I think he spots talent really well. He finds these people across Shopify that are unobvious people and he gives them the room to do their very, very best work. And that ability to completely ignore an org chart and rather focus on impact. And like, hey, that person I saw like, you know, he's in GitHub, he's looking at their commit and he's like, I like the way they wrote that. I'm actually gonna elevate that person and let them do something. You know, something much bigger, much more creative. And then probably the last one, I would say that we're kind of talking about it earlier is that I think what he's done for me is he sees a better version of me than even I see from me. I see pretty good version for me. I've always been someone who's somewhat, you know, fairly confident in my ability to get better at stuff. But he basically always shows me that there is a new gear for me. And he's like, you don't even know that that gear exists yet. But like you think you're in the fourth gear, there's a fifth gear. And he's like. And his expectation of me, and frankly I think the entire team is that we requalify for our job every year. And it's one thing to expect that your team is going to requalify, frankly. He also believes he has to re qualify every year. And the pressure that he, that he hasn't put more pressure on anyone else, that he puts on himself, that I think is an amazing thing.

[Sam Parr]

Does someone like him evolve into this Jedi Master type of guy? Or when you had 20 people or 10 people or whatever it was, was it clear that this guy's special?

[Sean Evans]

You know, I think a lot of people end up starting companies and working like, you know, spending their lives working with people that they probably would have been friends with in high school. Toby and I are totally different. I'm very. I'm like power extroverted. I love being around people. So remember I came to Shopify as a merchant first. I moved to Ottawa in 2005 to go to law school, not to become a lawyer. A mentor of my T shirt company, my T shirt business that I had in College at McGill here in Montreal had gone, became, you know, pretty good teacher business. I was able to pay for my tuition and my rent and help. My mom and my two sisters were going to private school that I was helping to pay for, that I. That I was paying for. I was paying my mother's rent at that point. A mentor of mine convinced me to go to law school, not to become a lawyer. But he thought of. He looked at law school as being like finishing school for entrepreneurship. And he was, he was a lawyer. He was teaching law at the University of Ottawa. He said, come to Ottawa, go to law school here. You're never going to practice law, but I think it's going to make you a much better entrepreneur. You'll learn, you know, how to crit, how to write better, how to think better, how to articulate yourself better. So I moved to Ottawa, have no friends, never even been to Ottawa before. It's the capital of Canada. Never been there before. Get there, and I'm like, where are the entrepreneurs? Those are my homies. Those are the people I always hang out with. And I met Toby through that. And at the time he was just transitioning from snowboards to software. And this is before I ended becoming an early Merchant. Even in 2005, he was thinking about what the future of the Internet might look like.

[Sam Parr]

So do you remember? Can you give us a bunch of those quotes?

[Sean Evans]

Yeah, I remember him. I remember him saying, like, for example, one of the things that, that, like, payments should have been into, should have been built into browsers. And I'm like, what? He's like, yes. Like the people that made browsers completely fuck this up. Payments should. Should be natively integrated, not through a third party, but natively built in to browser. That makes total sense. Identity should be built into browser entirely. So he was thinking about all the deficiencies of the modern web and then trying to effectively adjust Shopify's product to make those things much easier. The other thing I think that, that he had done that I thought was incredibly inspiring as someone that, you know, praised the altar of entrepreneurship was at that point, there were a couple companies doing E commerce. There was a company called Magento which ended up getting acquired by Adobe. There was a company called Demandware that ended up getting acquired by Salesforce. There was a company called ATG that ended up getting acquired by Oracle. And there's a company called Hybris that ended up getting acquired by SAP. And those were sort of the players there. There were some other ones too, like Yahoo stores, but like, no one is really doing like major GMV or volume on those. And I remember him sort of thinking that, telling me that the problem with all of these companies is that they're built for existing entrepreneurs, that there's never been anything built for aspiring entrepreneurs. Meaning if you have an idea in the shower in the morning, you can then go to your desk and get it going right away. And what if we were able to give the smallest of entrepreneurs of companies of ideas, the same tools that traditionally only the biggest companies could have? What would happen then? Well, the end result is that you, like, we now have. There's now been a trillion dollars transacted on over. Over a trillion dollars transacted on Shopify. And yes, we have some very large stores, but the majority of those of that GMV is the long tail small businesses and those homegrown success stories. Companies like Fashion Nova or Gymshark or all of these companies that started at their mom's kitchen table that grew super, super large. So those are a couple of the things in the early days that completely changed my perspective on one, how to think about building. But remember also, like, my own experience was sitting in law school, hitting the launch button on my online store, my T shirt shop, and all of a sudden I was getting sales from like, Ireland. And I'm like, for $29 a month, I think it was $24 a month at the time. Like, that was a dramatic insight for me that, okay, if you couple ambition and incredible product technology, you can actually change the entire, like, trajectory of entrepreneurship on the planet at a huge scale.

[Sam Parr]

Where has he been wrong? Where's the weakness? Where's the, the human side of this?

[Sean Evans]

Yeah, so he's.

[Sam Parr]

It sounds amazing.

[Sean Evans]

Are you guys familiar with the Enneagram?

[Harley Finkelstein]

Yeah.

[Sean Evans]

Okay, so the Enneagram is sort of. There's a lot of these personality things. The Enneagram is The only one, frankly, that I think is worth any. Worth any, any, Any review. But. So he is an 8.

[Harley Finkelstein]

The challenger. Characterized by a strong desire for control, independence and justice. They're assertive, decisive, and driven by a need to protect themselves and others. They're often natural leaders, confident and willing to take charge.

[Sean Evans]

Now go to 3.

[Harley Finkelstein]

The Achiever. Self assured. What is it? Self assured. Attractive. There you go. Charming, ambitious, competent, energetic. At their best, they are a role model who inspires others. But they have basic fears of being worthless. Basic desire to feel valuable.

[Sean Evans]

Oh, that hits, man, that hits. So, first of all, for anyone listening, if you are working in a team with a bunch of different personalities, it's a really effective thing to do to actually figure out what they are. On the Enneagram, we've looked at. I mean, I've looked at every one of them. We've had coaches on staff at Shopify for over a decade. This is the one that I think is the most valuable. So knowing that Toby being a challenger, me being an achiever, he is really tough. I mean, when I bring him an idea, he will beat the shit out of it to a level that I have, that I have not even considered yet. So it is not easy to work for him, but it is incredibly meaningful because what you end up with is outsized personal growth. He won't say 20 words when two will do. He'll say two. And if. If the two are correct and even though they may not be the most polite way to say it, he doesn't care. He is. He is seeking the best result like that. That is why he should be. You know, I will work at the company as long as they'll have me, and as long as he's there, because I believe he is the. The. He is the CEO that Shopify requires. No one will care more about that. But that doesn't make it easy, right? And like, I know other companies, I talked to my peers, other companies are like, yeah, you know, like, there is not a softness, but there was a collegiality to their culture. That doesn't happen in Shopify. It's not. It's not that we're not collegial. It's just like, that's not what we're trying to achieve.

[Harley Finkelstein]

This episode is brought to you by HubSpot Media. They have a cool new podcast that's for AI called the Next Wave. It's by Matt Wolfe and Nathan Lands. And they're basically talking about all the new tools that are coming out, how the landscape is changing, what's going on with AI tech. So if you want to be up to date on AI tech, it's a cool podcast. You could check out, listen to the Next Wave wherever you get your podcast. Did you guys ever have acquisition offers? You talked about how Magento sold and these other guys sold. Was there ever a moment, everybody sold where you guys had an offer or a discussion that you had to take seriously and you had a fork in the road moment? You obviously ended up independent. But was that always? Was that the only way this could have gone?

[Sean Evans]

If you look at the history of IPOs, particularly in tech, you will notice that Shopify from a market cap perspective went public at a much earlier stage than most companies did. What I will tell you is we first of all did not return phone calls from corp dev teams early on specifically because we didn't want to get into that headspace, that line of thinking. That wasn't what we were interested in. We wanted to build a 100 year independent company and we knew that those phone calls may result in us having meetings and talking about and thinking about it. And like we just didn't want that in our minds. It just, that feels like a real distraction. In fact, you guys know this too because you both invest in a lot of companies. Once you take that phone call from a corp dev person at a big company, you begin to inadvertently or advertently start a process in your mind of beginning to think about what if, what if the number is right, what if the terms are good, what if they have a, you know, what if there's a space for me at this company where I can, you know, the pitch that a lot of these companies make these big, you know, m and A conglomerates they make is like, well, you can do what you're doing at your current company, but you can do it here with more scale. So ultimately we didn't want to necessarily have that even in our minds. So we didn't return those phone calls first thing. Second thing is we went public at a very early stage because one, we thought it would be the best way for us to be independent longer term. And two, we felt the company was ready for it. Like the product was ready, the business ready, the team was ready. That's not really the case anymore. I mean, other than two companies I'm very close to, the one is Klaviyo, you know, Andrew, who's founder of Klaviyo, went public last year and then Fiji, who was at the time CEO of Instacart, is on our board, went public as well, so you've had a couple IPOs, but generally companies are. And in the case of, you know, most of these companies, they're much larger. They're in the tens of billions of dollars of market cap before they actually go public. So our. We just didn't want to get acquired and we wanted to be independent.

[Sam Parr]

But were there ever times where you were like, I would like to. I would like to take this deal. This would be nice?

[Sean Evans]

No, there. Truly, there was not. We did a very small secondary on. I think it was the series B, which allowed me basically to buy a house, a down payment on a house.

[Harley Finkelstein]

And what's your philosophy? Are you like a de risker over time or are you like, fuck it, all the eggs in this basket? Like, what's your philosophy around that? Because it's tricky, right?

[Sean Evans]

Like, even if you believe money isn't so money's. So my. So you. I mentioned my dad wasn't around when I went to gone to college. My dad, you know, he was. I love my dad. He's a great guy. But my dad really never made it as an entrepreneur. And growing up, money felt emotional to me that some weeks we had and some weeks we didn't. We never. We never, you know, we always had food on the table, for example. But there were times where I remember as a kid, often my mom would come sit me down and say, hey, like, we're gonna have to, you know, tighten our belts this month. That tightening of the belt happened a lot during my childhood. And so when we went public, yeah, for the first time, I had real money. I was able to, you know, I was on a 10B51, which in Canada we call an ASTP, an automatic share distribution plan. So I was able to take a lot. But I mean, I don't think there's any better investment for me, my family, than. Than Shopify. But I've taken money off the table so that I feel like my family is secure, my children are secure. We're never gonna have to tighten our belts. And that. That's not a flex that. That truly makes me feel I'm able to do better work because I know that I have a nest egg that is protected.

[Harley Finkelstein]

What was the hardest. What was the hardest moment at Shopify was there? What was rock bottom? What was the low?

[Sean Evans]

Covid was really, really hard. Maybe not for the reasons that, you know, you guys, I mean, remember, Shopify went from something like.

[Sam Parr]

I don't know.

[Sean Evans]

Maybe pre Covid we were $30 billion company. We, like overnight have your revenue.

[Sam Parr]

I think in 2019 you were at 1.6 billion and then 2020 you were about 3 billion.

[Sean Evans]

That's a big jump. And it was a big jump in everything. What happened during the pandemic was, I mean E commerce as a percentage of total retail was sitting at around 15% in the US so 15% of all retail was online. And then effectively you had this pull forward during the pandemic where we jumped very quickly to 20 something percent.

[Sam Parr]

Sean, to answer your question, what was the hardest time in Shopify? You know, we almost didn't make it. We grew from 1.5 to unrevened.

[Sean Evans]

Can I finish my fucking story, guys? So, so there, there was, there, there was this manic like period inside of Shopify. Like all of a sudden all these, this pull forward, for example, like everyone all of a sudden need to go online. All these laggards that were just physical retailers eventually came online. And I think at that point it was like just, just get shit done. And then 2022 happened and like the market started going the other way. And like we kind of found ourselves with a much larger team. We found ourselves with a lot of side quests. Shopify also, for the first time ever, I think we were not profitable. So I think that sort of post Covid hangover was, was really tough for us. And that's kind of where like, I think, you know, you asked me about these different phases. That's where I think sort of the next phase came into play, which is, okay, like, do we need to figure out, like, what do we care about? What is the right team size? What are our focus areas? Do we have the right people leading the company? And that was sort of this, like we recalibrated everything. That was really hard. I wasn't sure I knew Shopify would make it. I wasn't sure if I was going to make it.

[Sam Parr]

Was there ever a time where you thought that Shopify wasn't going to make.

[Sean Evans]

It pre IPO for sure. I mean post IPO things, you know, we went public at a time where we sort of knew what the next 10 years would look like. We were profitable, we were making money. We were, you know, we were subscribing to this whole like, you know, you know, grow, grow top line and also grow bottom line. But pre pandemic there was, sorry, pre, pre IPO there. I mean that was hard, right? Like, I mean we were bootstrapped for a while. There were times where we didn't know if we can cover payroll. But you know, I think you have to be a little bit, you know, crazy naive.

[Sam Parr]

Sean and I, you know, my last company, we were going to do about 20 or 17 million the year we sold, but I sold early in the year. Sean has a business that is in, like, you know, he's got his hands at a bunch of things that are. That are potentially in the. In the similar range. I don't want to speak for him, but I don't think either of us have experienced this, like, 50, $100 million range where I'm like, oh, then I could just, like, manage, like, three amazing people who do most of the work. I'm in the phase now with my business where I'm like, everything is fucking hard. Like, if someone. If someone quits, I gotta go do the work. And so what I wanna know is.

[Sean Evans]

Like, does that go away?

[Sam Parr]

Does it get more fun?

[Sean Evans]

No. No, it doesn't. But actually, like, I don't think any of this gets easier. You just have different problems. It's like the. But it's like the magic number. We all have this magic number early on as entrepreneurs, especially if you grew up the way that I know, you know, Sean, Sam, and I grew up the way that, like, we all have this number in our mind. We're like, when I get that I can think, I can basically extrapolate my passive income from it, and that's going to pay all my expenses, and I can do. And then you hit the number, you're like, it's like. It's bullshit. It's complete bullshit. There is no magic number. Just like, there is no stage of a company whereby you are cruising. It's just different problems, right? So the problems that I have with, like, at 7,000 people and $100 billion market cap are very different than what it had with, like, 70 people.

[Sam Parr]

Which problems do you enjoy more?

[Sean Evans]

This is my favorite stage of Shopify because as going back to the whole spiky object, the thing that I think I can add, the way I can add the most value to Shopify is through storytelling. And I believe now the microphone that I have because of Shopify, size allows me to do it at this point, crazy scale. And I think for that, it means that, like, my life's work gets to be more amplified today than it did 10 years ago.

[Sam Parr]

I remember you be. You've always been lyrical and good at talking. You are now much better. You are always. You're always good. Now you are, like, really great. Do you have, like a. Do you have, like, a writer? Like, is there someone who's gonna watch this. And be like, this bit hit.

[Sean Evans]

No, you guys asked me for notes. You guys asked me for notes this morning. I had to, like, literally sit down and write you notes myself. No, there's.

[Sam Parr]

Yeah, we didn't use that name up.

[Sean Evans]

Yeah, exactly. I don't even think. I don't even know what I wrote to. Wait, what?

[Harley Finkelstein]

I DM'd him this morning. And I was just like, hey, saw that, you know, whatever. Excited for the pod today. And I was like, you know, the best episodes tend to be where the guests come in with, you know, these three or four bullet points. I gave him some guidelines. Like, you know, I was like, no. I said, I noticed you hadn't filled out the prep doc. We usually send a guest, like a prep doc, and they fill it out, and then it gives us kind of like a, you know, some options of where you can go in the conversation. And he goes, prep doc, dude, let's just hang. And I was like, oh, yeah. Oh, I gotta be. I gotta be cool. Okay, my bad.

[Sean Evans]

Yeah, so. So, I mean, I had. I have a team of people that help me with things, like, when I'm preparing for. But no, this is me. There's no notes. There's no but you should, like.

[Harley Finkelstein]

I actually heard a couple of stories recently that have really inspired me. Okay, I'm gonna give you a little. Like, there's a framework that I think most people underestimate. Okay. So there's a story in sports that LeBron James sends a million dollars a year on this body. The numbers is actually kind of irrelevant, but the idea is directionally correct. LeBron James spends a lot of money on his body, and he has certain, you know, treatments and coaches and, like, protocols that he follows that the average athlete is not following. In fact, we went to an NBA team, and I said, how many of you guys have chefs? And less than half of that team in the NBA raised their hand. I was like, this is insane. I couldn't believe the owner would even allow that. But, like, for LeBron, every meal is dialed. Every. You know, every hour of the day is either recovery. It's. It's building, or it's, you know, it's playing. And so LeBron does that in his field. I then talked to somebody who knows Peter Thiel very well, and I go, you know, it's weird because Peter, he's not, like, a smooth talker, right? He's actually, like, stutters a bunch. He stumbles. But when Peter Thiel goes on tour and he does it, like, every, you know, seven to Ten years he's got this message, and boom, he'll get, like, a ton of pr. His message is very effective. So he's not very efficient with his words, but he's very effective. And, you know, if you remember, he did one where it was universities are a bubble. Yeah, right. And he went on a whole tour of that, and then he launched the Thiel Fellowship underneath it. And he did one which was competition is for losers. And he has these, like, slogans, almost like marketing slogans. Accomplish for losers. Then he launched Zero to One, his book that was all about how to build a monopoly. And he did one with When Trump first ran. And he was like, you know, and for founders went ahead, we wanted flying cars, but all we got was 140 characters.

[Sean Evans]

Yeah.

[Harley Finkelstein]

Now, Peter did not write that line. In fact, what my friend told me is that Peter actually kind of, like, has a guy who follows him around that's listening to all of Peter's thoughts and then sort of workshopping his bits. Like a comedian would, like a. Like a politician speechwriters would. And they actually, like, craft the message and they write it out, and they basically get him prepped for media. He's not showing up and just winging it. And. Because maybe he's not that great at winging it. David Rubenstein does the same thing that.

[Sean Evans]

You know, I know David. David actually has even a larger team because he does the show and he does the TV show, and he obviously with Carla and stuff. So I don't necessarily have. Have a writer per se. I do have people that kind of remind me of, like, hey, like, remember that, like, this is kind of the direction. I'll give you the best example. Earnings calls. I meet with my. My Jeff Hoffmeister, Amazing, amazing cfo. I met with Jeff and our IR team, and I'm like, all right, what are the three or four things that, like, that we want to. We want to say? And then I basically take it and. And I. I, you know, hardly arise it. I make it sound like me.

[Sam Parr]

So can you give an example? So an example is like, we want to get. We want to be on Roblox or something.

[Sean Evans]

On the Roblox thing. It's really about the fact that Shopify is no longer just an E commerce company or the commerce Everywhere company. Okay, Right. And that's what's important. So I'm using Roblox as effectively a proxy for explaining that you may not necessarily, you know, want to sell in Roblox if you're selling hand sanitizer, but if you if you're selling another product and your audience spends time in Roblox or. Or in some sort of in a metaverse, you may want to access it by being on Shopify. You are default selling everywhere.

[Harley Finkelstein]

Right, Right. The story isn't we're on Roblox. The story is we're now the E. Commerce. We're now the commerce everywhere.

[Sean Evans]

We're also on Pinterest and Instagram. There's literally a Spotify, a Shopify for Spotify channel, where you can actually, if you're Beyonce and you have an artist profile like the size of Beyonce, you can sell Sacred, which is her cosmetic line on Shopify, inside of her artist profile.

[Sam Parr]

And rumors are you're going to be on ChatGPT.

[Sean Evans]

That's rumors. Yeah, we're not gonna go there today, but exactly. We want to be wherever you effectively have consumers. So earnings was three weeks ago. And I love earnings. I go, I do my earnings call, I then do my analyst calls and then I do my media tour. In this case, I did tbtn, which I think those guys are killing it. I did cnbc. I did some Bloomberg stuff. I noticed that there were a bunch of other companies that. Because I listen to earnings calls a couple days before and a couple days after, just to kind of hear the tonality of the reporters and the journalists, but also of the executives. And Sebastian from, I think. Is it Klarna or something? He basically came out. I think it was Sebastian, and he said, hey, after his earnings call, the whole thing was done by AI that actually was. It wasn't even him. It was basically an AI emulating his voice. And that's who did his earnings call. And it made a splash. There were a couple articles about it. And so I listened to it. I was like, yeah, that's like a 5 out of 10. And maybe you can say it's a 600 or 7 out of 10 because he saved a lot of time and so is effective. But there was zero, in my view, there was zero personality to it. And then I watched a bunch of other kind of quote unquote, professional executives that were. That did their earnings calls, like the P and G guys, for example, or the folks over at Best Buy. And I listen to their earnings calls and I'm like, yeah, they sound like they're reading a script. If you go back, you don't have to do this, but if you go back and listen to Shopify's earnings calls, you'll hear things like, okay, I know what I just said, and I know you think that's surprising. I'm going to repeat it again because it's really important. And I'll use voice inflection and I'll use repetition, and it doesn't. And what I've. And what I hear back from. It's like theater. What I hear back from both analysts and investors is that they find our earnings calls to be so much more interesting because what they actually hear is our personality. They hear the passion in my voice for we give a shit about this stuff too. And so I think that there's probably a right balance where you have people around you that are giving you sort of the macro things. But like, if I start talking like Peter Thiel, it's not authentic and therefore I don't think it'll be as effective. And so I think there's a balance that I'm trying to find. And so I've been. I've done 40 earnings calls now. The balance I have is tell me what are the most important things that we need to hit and then let me kind of find my own way of negotiating it into the call.

[Harley Finkelstein]

Right. I like that you, like, studied the game film of the other earnings calls.

[Sean Evans]

That.

[Harley Finkelstein]

That was what I was looking for. That like kind of that extra that you go to that others, others may.

[Sean Evans]

There are people that. I mean, Benioff's fantastic at it.

[Harley Finkelstein]

Do you. So Toby came out with this like, memo that was like, hey, it is a baseline expectation.

[Sean Evans]

He didn't come out with it. It was leaked. But yes.

[Harley Finkelstein]

Yeah, it was leaked.

[Sean Evans]

Someone leaked it.

[Harley Finkelstein]

I always assumed those are like intentionally leaked. I would have intentionally leaked that if that was him.

[Sean Evans]

I think in hindsight, some of these things, when they do get leaked, you're like, you know, better for worse kind of thing.

[Harley Finkelstein]

But yes, but the point is in it, he was basically like, yo, AI is an expectation based on expectation. You got to learn these tools. The way to. The way to get good at them is to use them a bunch and you got to start solving problems using this was the general, general ethos. I'm curious, you personally, Harley, day to day, what's your AI usage? Are you like, you know, a lot? A little just chatgpt, other tools. Like what are you actually personally just using either professionally or personally in your personal life?

[Sean Evans]

Two things. One is, I mean, I use ChatGPT. I really like the fact that now it's like, I like the history side of it. So, for example, like back to sort of longevity, every time I get a blood test, I upload it to chat gbt. In a folder called Longevity and Health. And so now I can ask questions. Although I do find if I say, like, I had a bullet test last week. I uploaded my new one. I said, compare this to my last one and it compared it to one from three, like, like a long time ago. And I was able to spot it. So it's not a hundred percent, but I like using that quite a bit too. I. I gave a keynote at Summit last week. I literally fed my entire keynote script into Chat dbt and I said, hey, and what parts of these do you think are confusing, if any? Like, where am I? Where am I losing the thread here? So I think that I use ChatGPT and particularly O3, the O3 model on a daily basis. Sort of like, you know, on my, like, I have two screens here. So based on my screen next to me, I always have that open. I really like Claude for other projects. So for investing, for example, you know, Lindsay, my wife, and I do a little bit of investing. We own some apartment buildings. So I have a file for real estate, which is every time I get an update from the property management company, I feed it and I find Claude is much better for analyzing existing documents. I find that ChatGPT is much better for sort of reaching out into the public sphere, like the web and bringing things in together. Those are the two I use the most. And then back to sort of the earnings calls. One of the things we did was we basically made all of Shopify legible and we built like about a dozen MCPs inside of Shopify. So usually in preparation for an earnings call, I will go to. Let's say I want to talk about like, Shopify Capital. I'll go, let's say I want to talk about, like, we launched it in the uk. So let's say I want to go, I want to talk about that. In the earnings call, I'll go to the capital leader and say, hey, give me a couple of the highlights for uk. It's a new one for us. I want to talk about how it's going this time. I just went to the vault and literally went into like, cap the capital program because everything is legible. I was able to pull most of the data on my own. The personal jury. Jury still out. Whether or not I miss. Because when I talk to the leader of capital, I get some of the nuances and I'm like, oh, you just said this sort of thing and like, actually I'm going to take that and run with that. Even though it wasn't. You didn't intentionally mean to leak it to me or tell it to me. Whereas using basically like the Shopify vault, which is where I'm able to access all this data through the mcps, I find that I'm basically getting a lot of headline stuff. But I do want to make one point. One of the things that got missed on Toby's memo now, or the email now is that there was a term he used that I'm surprised more people haven't picked up on, which is like AI, like being reflexive. And part of what he's trying to get the company to do is to be reflexive about the usage of AI so that rather than sort of make it a sort of I have a project and now like I'm working on my own. Oh, you know what? I should also use AI and see what I can get from ChatGPT or Claude or Anthropic or something like that or complexity. This idea of making it reflexively part of our day to day work is really what he was trying to do. And in fact so much so that he created this like this new friction which is before you can go and hire someone on your team, you first have to substantiate to shopify to the hiring manager to the talent team why AI cannot do it better. And one of the things we're noticing there is by actually creating this like friction of saying like, before you go and hire, you must first do it. What ends up happening is people, by the end of substantiating why they need to hire someone that AI can't do, realize that they actually should have. AI can do a bunch of that as well. That is very different than what you're hearing, I think in most companies, which is, let's just use AI as part of our, you know, if I have to design something in figma or in canva, I'm going to use AI to help with that. That this idea of it being reflexive is sort of what we're trying to do.

[Harley Finkelstein]

I like that a lot. That's cool. That's a great little nuance and sort of tactic. I like these sort of either incentives or systems where you do one thing, but it has all these downstream impacts. Right now people are talking about the US like, oh, the deficit's so crazy. And Buffett has always said this thing. He's like, oh, simple, I could solve the deficit in two minutes. Here you go. If we run a deficit over 3%, nobody gets to keep their job in Congress.

[Sean Evans]

That's right.

[Harley Finkelstein]

Watch, watch what happens.

[Sean Evans]

I mean, that is you get to do that at companies. I mean, back to like the phase of the company, at the phase of size and scale of our company, we get to do stuff at this crazy scale. So simply by adding, you know, a simple friction on hiring that says first substantiated, you actually see incredible results. Then you can evaluate, you can literally say, like, okay, well, how is hiring changed since that that email was leaked? How is hiring change since we added that friction thing? It's very difficult to actually see the efficacy of all these things when you're 10 people.

[Harley Finkelstein]

All right, this episode is brought to you by Mercury. They are the finance platform of Choice for over 200,000 companies. Shouldn't be surprised because I use it myself for not one, not two, but I have eight different Mercury accounts. I have seven for different companies that I'm a part of. And then I have my own personal account because now they have personal banking, which is a really cool feature. I highly, highly recommend it. Like I said, I use it myself. And the reason why is because the way that Mercury works is beautiful. It's very intuitive and you could tell that it's actually made by a startup founder. It's an entrepreneur. You could tell it's made by somebody who used other banking products in the past and didn't like all the different rough edges and annoyances and decided to actually fix it himself. And really, any type of entrepreneur you are, let's say you're an agency. Well, one of the things every agency has to do is be able to send invoices easily create them, send them to customers, and stay current on your balances with all your customers. Well, you can do that inside market Mercury. And so I think that Mercury is great. Highly recommend you check it out. And thank you for sponsoring the show. For more information, check out mercury.com Mercury is a financial technology company, not a bank. Check show notes for details. Well, you look really healthy and you have a lot of energy. I'm curious, you said you got curious and kind of interested in biohacking slash longevity. You're on a kick right now. What's got your interest? What are you doing that's maybe you feel is either interesting or working for you or you're enjoying it. Just give us kind of like a quick health dump.

[Sean Evans]

So I sort of divided into two buckets, which is like I'm going to die of one of two ways. I'm going to either die because of cancer or I'm going to die because of heart attack. And so the cancer thing, it's not Easy. But Prenova does a lot of that heavy lifting for me, or at least I'm 41 now, so I'm now getting to the point where I'm taking a lot more seriously. So once a year, and there's. Prenova's not the only one. I like it a lot. I like it so much that I actually invested in the company. My wife and I invest in the company a couple of years ago. I think the way they do it, I think the way the technology is moving, the fact that here's a very simple thing. A lot of people don't like going into these full body MRIs because they get claustrophobic. So a small, you know, I guess part of the product of Prenova is you put on these glasses that have these mirrors and the mirrors go backwards into a screen. And I watch like the most, you know, fun loving light show that I can find. For me, that's Seinfeld. So I'm also some. I'm not claustrophobic, but I don't, I don't, I don't. Wouldn't want to stay in something like that for a long time. Dude.

[Harley Finkelstein]

When I went in, I watched Top Gun. I was like, oh, what's a movie I should have watched? But I never did. I just watched.

[Sean Evans]

I'm like, I do not want to be stressed out. I don't want to be scared.

[Sam Parr]

I watched a zodiac killer documentary on Netflix. It was great.

[Sean Evans]

I mean, that speaks volumes about both your personalities. I watched like personality test and so, so I. So that sort of takes you on the cancer side. On the cardiovascular stuff. I just said clearly a clearly scanned, which basically looks at blockages. So. So what I'm trying to do, what I did initially was I just got a baseline of like, where am I at right now? The reason I like Prenova each year is because I basically can look over time how things are changing. If I have like a benign cyst on my, on my liver, is it growing year over year now at least I can monitor that stuff too. So to me, those are the two main buckets. And then I just try to do these, like these misogies is like one thing every year that scares the out of me. And the thing I really like right now is called 29029 and Jesse Isler, Jesse Itzler's thing, Jesse's. He's done an amazing job. Him and Mark, who's his partner, co founder, they've created this incredible thing that effectively allows you to climb Everest. But you can do it from like Colorado, in my case, I do it in Quebec, I do it in Mont Tremblant, you can do it in Vermont. But they created this incredible thing that allows you not to have to travel to Everest, Mount Everest, and you actually can do it. And so I've been doing this, this was my second year doing it. And I, and I like doing it not just because of the like high five. It's cool to, to, to climb, to emulate climbing Everest. But I like the idea of getting really scared that I'm going to fail at it. And therefore I train much harder. And so my workouts actually are much better because I'm so scared of failing at this. 29. It has a 29 thing.

[Harley Finkelstein]

Yeah, yeah.

[Sam Parr]

Dude. How, how many. Last question. How many, how many companies in the world are bigger than Shopify? You guys are worth it looks like 1:53 today or something or once. Whatever. 130. You've been as high 34, 200.

[Sean Evans]

Down by $20 billion.

[Harley Finkelstein]

Just one of casual.

[Sam Parr]

Casual. What's crazy is like you're worth, you're worth 134.56 billion. Like change that five six to like a five, five and like that's like life changing, you know what I mean?

[Sean Evans]

It's crazy for sure. No, it's wild. I, look, let me, let me, let me. One more, call it for. If you were listening to this and you are a company that actually like, you know, you understand your business well, you see great growth potential. Like this idea of, of avoiding the public markets is insanely silly to me. It's been an incredible 40 quarters in now. It's been like an incredible journey for us. It makes us a better company. It allows, I think the people that use Shopify find more confident. I mean now we have companies like Hunter Douglas and Mattel and Birkenstocks using Shopify. I think one of the things they love about it as a product is that like being publicly traded provides some sense of stability.

[Sam Parr]

Well, what I was going to say was I looked it up up on ChatGPT. So there are probably 120 companies in the world bigger than you. Which means of all the companies that have ever been started, of all the companies that are out there right now and probably in the history, given that like today's companies are bigger than everyone else, you are in like the top 150. It's pretty astounding. And I think that like if there was a ratio of like somehow most relatable or like for some reason when I talk to you, I'M like, he's just one of us. He's like, one of us almost.

[Sean Evans]

That's my friends.

[Harley Finkelstein]

He's not one of us, damn it.

[Sam Parr]

And then I, like, see this, and then I see the stats, and I'm like, he's so good at his job that he's tricked me into thinking that he's relatable.

[Sean Evans]

You know, me personally, we've. Look, I think I said this at the beginning, right? I. I was guess.118.

[Sam Parr]

We are not the same, my friend. We are not.

[Sean Evans]

We are the same. And now you've had over 750 of them.

[Sam Parr]

We are not the same. And.

[Sean Evans]

And.

[Sam Parr]

But if there were a ratio of, like, I feel like I could do whatever he's done to approachability to market cap ratio, you are. You get the gold medal.

[Sean Evans]

I think that's the sweetest thing you've ever said to me, Sam.

[Harley Finkelstein]

You know. You know what's one of the best things I did after that first podcast is basically every year for the last five years, I take about 20% of whatever my profits are out of my Shopify store, and I just buy Shopify stock.

[Sean Evans]

Oh, wow.

[Harley Finkelstein]

And that alone, I think, has compounded as good or better as my actual econ brand, because now my earnings are growing, whereas, like, if I just reinvested it in the business, not every business you can reinvest 100% of your profits back into. And so just that one little habit has been very, very helpful for me.

[Sean Evans]

Well, that means a lot to me. It's actually cruelly neat. I get to. We're doing this thing called chocolate milestones. Like, basically, it's our version of the Emmys or the Oscars for actors or the Grammys for musicians. We give these milestone awards. You guys have probably seen them around. This is the 10,001. So we get for 10,000 orders, 100,000 and a million.

[Harley Finkelstein]

I got a bone to pick. Y' all are so slow. I got my milestone, but I'm already on the next order of magnitude like this. Yeah, it's so slow how you guys said these out.

[Sean Evans]

I mean, these are heavy. We had to, like, share them out and stuff. There's a lot of people. But anyways, so I get to. I deliver a bunch of these.

[Sam Parr]

Excuse.

[Sean Evans]

They're heavy, so you need to get to a million first. And I'll deliver your million one, John. But I meet these people when I deliver them, and often what I hear is not only, like, obviously they built their business on Shopify, but many of them, you know, like, they They're. They're also shareholders, which I think is an unbelievable endorsement. As, like, you know, it's one thing to use the product and build your business on it, but then also to you invest your, you know, your. Your hard earned money into.

[Harley Finkelstein]

Be clear, not an endorsement, just a recovery of fees is what I was looking for.

[Sam Parr]

Okay?

[Harley Finkelstein]

I'm paying you guys this money. I'm gonna get it back in the day.

[Sean Evans]

You made it. You made it sound way less romantic than I did. Just exactly.

[Harley Finkelstein]

Let's be real here, dude. Thanks for coming on, man.

[Sean Evans]

Dude, this is great. You guys are the best. I feel like I could rule the world. I know I could be what I want to. I put my all in it. Like my days off on a roller best travel, never looking back.

[Sam Parr]

All right, so when my employees join Hampton, we have them do a whole bunch of onboarding stuff. But the most important thing that they do is they go through this thing I made called Copy that. Copy that is a thing that I made that teaches people how to write better. And the reason this is important is because at work or even just in life, we communicate mostly via text. Right now, whether we're emailing, slacking, blogging, texting, whatever, most of the ways that we're communicating is by the written word. And so I made this thing called Copy that that's guaranteed to make you write better. You can check it out. Copy that dot com. I post every single person who leaves a review, whether it's good or bad. I post it on the website, and you're going to see a trend, which is that this is a very, very, very simple exercise. Something that's so simple that they laugh at. They think, how is this going to actually impact us and make us write better? But I promise you, it does. You got to try it@copy that.com. i guarantee it's going to change the way you write. Again, Copy that dot com.