The Longest Shutdown Ever | Ep. 036 Lemonade Stand ๐Ÿ‹

5 Nov 2025 ยท 1 h 39 min

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Lemonade Stand Podcast Episode Notes

Episode Information

  • Title: The Longest Shutdown Ever | Ep. 036 Lemonade Stand ๐Ÿ‹
  • Recorded On: October 4th, 2025
  • Hosts: Aiden, Atrioc, DougDoug
  • Guest: Harley Finkelstein, President of Shopify
  • Summary: Discussion on the historical government shutdown, interviews with Shopify's president, and the state of business, tech, and politics.

Segments

  1. Intro (0:00)
  2. Shutdown Watch (1:55)
  3. SNAP (11:30)
  4. China Tariffs (24:01)
  5. New York Elections / Zohran Mamdani (28:20)
  6. California's Prop 50 vote (40:09)
  7. Quince Promo (41:17)
  8. Air Traffic Controllers (43:28)
  9. Interview with President of Shopify (46:05)
  10. Post Interview Discussion (1:27:21)
  11. Outro (1:38:12)

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Key Highlights

  1. Government Shutdown
  2. Historical Context: Currently experiencing the longest government shutdown in U.S. history, lasting over 35 days.
  3. Democratic Stipulations: Democrats demand three conditions before passing a budget resolution:
  4. Continued funding for ACA (Affordable Care Act) subsidies.
  5. Reversing Medicaid cuts.
  6. Addressing unilateral spending cuts made by the Trump administration.
  7. Republican Stance: Republicans have been largely unyielding and have not engaged meaningfully in negotiations.
  1. SNAP Benefits
  2. Impact of Shutdown: Funding for SNAP (food assistance program) is at risk due to the shutdown, affecting millions of Americans.
  3. Federal Judge Ruling: A federal judge ordered the Trump administration to allocate funds for SNAP, which is not being complied with.
  4. Repercussions: The failure to fund SNAP leads to delayed payments for beneficiaries, causing strain on food banks and low-income families.
  1. New York Elections
  2. Zohran Mamdani's Lead: Current indications suggest that Mamdani is likely to win the New York mayoral election.
  3. Campaign Promises: Key promises include universal childcare, freezing rent for certain apartments, and increasing taxes on wealthy residents.
  1. Interview with Harley Finkelstein (Shopify President)
  2. Shopify's Growth: Discussion on Shopify's recent earnings call indicating a strong growth trajectory with a 32% year-over-year increase in revenue.
  3. Role of AI: Discussion on how AI tools like Shopify's Sidekick are democratizing entrepreneurship by providing support usually reserved for larger companies.
  4. Canadian Entrepreneurship: Finkelstein expresses optimism for the Canadian economic landscape, citing Shopify's growth as an example of successful entrepreneurship amidst traditional industry dominance.
  1. Closing Remarks
  2. Future Outlook: The episode closes with discussions about the potential future of entrepreneurship and the importance of providing tools and resources to individuals looking to start their businesses.

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Key Takeaways

  • The ongoing government shutdown continues to impact various sectors, including healthcare and food assistance.
  • The potential effects of SNAP funding cuts could exacerbate issues for vulnerable populations.
  • New York's mayoral election and the outcomes of local policies may create ripple effects in economic support and community welfare.
  • Shopifyโ€™s growth and innovative use of technology reflect a shift towards more accessible entrepreneurship, particularly in Canada.
  • The optimism expressed by Finkelstein highlights a burgeoning entrepreneurial spirit that could reshape the Canadian business landscape.

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Conclusion This episode of Lemonade Stand dives deep into pressing issues regarding the U.S. government shutdown, the impact on social services, and the exciting developments in entrepreneurship with insights from Harley Finkelstein. The discussions draw connections between policy, business, and technology, showcasing the dynamic landscape of modern business in a changing world.

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Transcript

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0:00Ladies and gentlemen, welcome to the stand. just the stand this time just the stand it's just cleaner we dropped doug we dropped the lemonade it's just the stand when it's us two our co-host and compatriot doug doug is out this week he's already in japan scouting the place out for our eventual arrival and uh we have a lot a lot a lot of news going on right now including the world's but the world i guess america's largest shutdown in history it's still the world the entire world it's the longest shutdown ever experienced there's never been one longer don't start doing it ironically because you will do it for real i've already fallen into that i'm online streaming i'm doing this regularly he actually invented such a great emphasis um and speaking of him he had an insane 60 minutes interview last night we'll that for a bit.

0:54And then also in New York, as we are recording right now, live Zoran Mamdani is leading this mayoral election and may, I mean, it's seeming pretty clear he's going to take it. So we'll talk about all that. Yeah. And we're going to round out this episode with something new. We've been discussing doing shorter, like non full episode call-in interviews for a while. And we have a Harley Finkelstein, who was a guest, a guest of ours that we've already recorded before this uh that'll be at the end of the episode and our discussion of that interview after he's the president of shopify which just released its quarter three earnings recently became the largest company in canada by market cap and it's just an interesting interview to get to you know speak to somebody who runs a business it is that you like scooter over here from the yard set like talking about god knows what and then interview ceos yeah yeah that's my job That is my job.

1:53What a deranged world we live in. But, Brandon, we are on day 35 of the government shutdown. World record! And it is the longest government shutdown in U.S. history, breaking the record of the 34-day shutdown that was also during Trump's first term. And I think there's a few... I wanted to do a short recap. We did an episode at the beginning of the shutdown where we discussed the reasons why this has been the case. And basically, the budget resolution that is necessary to pass in order to continue funding the government is being held up by the Democrats are putting their foot down. They won't vote on a budget resolution until they get three things.

2:33They have three stipulations at the moment. One is that the ACA Affordable Care Act, AKA Obamacare subsidies that allow a lot of people to buy or afford their coverage are expiring in December of this year. And that has a huge increase to the premiums of a ton of people's healthcare across the country. I think it's like tens of millions. You can go back to the episode where we talked about the first time. That is a bad idea. And also, second, reversing the Medicaid cuts that were passed in the big, beautiful bill earlier this year. We love the BBB. That we also discussed on an earlier episode.

3:13And then three, a point that goes unmentioned a little more often is Trump throughout the year has, or Trump's administration, has chosen to make unilateral decisions about cuts to agency spending. Right. Breaking from previously passed budgets by Congress. So Congress has laid out some sort of budget plan that would fund some sort of agency or organization within the government. And Trump throughout this year has made the decision to cut funding to certain areas, fire employees through organizations like Doge or through himself. Remember Doge? What an era. Wow. Way back when we were talking about that a lot.

4:00It actually does feel like much longer ago than it is. Yeah, but it's not actually. It was the beginning of the year. But the Democrats, I think, fairly have a problem with the way these cuts have been handled in that there, if it is the responsibility of Congress to pass and approve budgets, and then the executive branch chooses to make its own decisions about how cuts can be made to those budgets, then you're overriding the decision-making power of Congress. What was the point of the whole legislative process and voting if it just gets overruled by the executive? I think that's a fair point.

4:36And it also means that if there's any commitment in the negotiation of this budget resolution now, if there's no agreement about no longer doing this in the future, that means any decision you come to, it doesn't even really matter in the future. I mean, we talk about this, the similar thing is, you know, we come back to that TikTok example, but it's like a lot of people went through a lot of effort to get through that through the House and the Senate and the judiciary and everyone vote on it. And then it didn't matter. He just wrote a, he wrote an executive order and it changed. So it's like this.

5:04and nobody wants to fight that one nobody cares about nobody cares about that one to fight it but i think if you worked in that part of the government it's like well what what the what the fuck is the point what are we doing what are we doing uh so those are the three stipulations that uh democrats have have chosen to put their foot down in a situation where they don't have a lot of like political support or credibility right now sure and there for them this is a move to show some spine hopefully gain back some support and they have very little to lose and then And on the other side of things, the Republicans have throughout the month seemingly refused to negotiate.

5:40I've seen basically no news. I don't know if this is different for you. I've seen basically nothing about progress on the negotiation front. I have seen that this week, some quotes about people becoming optimistic, but no concrete progress as to a resolution to end the shutdown. Yeah, I will say like we talked about this when it was way earlier in the shutdown, that the thing that usually stops this train is people stop showing up for work on critical roles like air traffic control. They all play D &D? They all play. Yeah, they all go play D &D. They put on fursuits like you, Aiden. Sorry, I'm just so stupid.

6:23I just make such dumb fucking jokes. I feel bad.

6:29But it's happening. It is happening now. That prediction that you made has come, I mean, incredible look at the past, has come to pass. People are calling in sick. They are, you know, they're taking their PTO. They're not showing up. Airlines are, I talked to someone whose mother is an air traffic controller, and he was giving me exact details on what's going on. They are changing the flights so that flights can no longer be within five miles of each other. They'd be within 20 because they're stressed about having understaffed people. So they're reducing the chance of risk by making flights farther apart.

7:04I mean, they're, they're, they're adapting. They're offering people, they can't give them money, but they're offering them paid credits for like pre-worked hours. And you can take time off in the future. So if you work eight hours now, you can get an eight hour show off in the future. And a lot of people, this woman who's older, has told me that the older generation are all taking all the credits and working extra hours. And the millennials are calling it sick. That's what she said. It's a little generation bias, but. that that's what we're seeing. And so, you know, we've already seen some shutdowns at LAX and some major airports.

7:37And I assume that's going to continue to spread. So there, there is that pressure, but I will agree with you that like, I don't remember that well, the last shutdown, but I remember it having more of at least the pretense of negotiations during that, that weren't, this one feels like nobody's bothered. Yeah. There was a loose idea. This is all vibes, right? Yeah, this is a vice base. Because it's hard to remember how exactly I felt at the time and what the news cycle day-to-day was like at the time. But this is the first one where I have a feeling of, oh, we're not even trying to figure this out.

8:09Like, that's what it feels like. That is what I feel like. It feels like both sides concretely think the other one will cave and they have nothing to gain by negotiating, really. Maybe that's more the Republican stance than the Democrat stance, but I listened to Trump's 60 Minutes interview last night. They asked him this question and he essentially said like, they're going to cave. That's his, that is his plan. It's two part plan. He said that, or we're going to get rid of the filibuster and then just force this thing through. Yeah. So I wanted to talk about that quickly. I had a misunderstanding of the filibuster before this.

8:40I thought the filibuster was exclusively when you delay the progress of a bill by continuously debating or talking about it. But they've been voting on the budget resolution over and over and over, the stopgap bill. I think they voted maybe 12 times as of today, and they just keep not passing it, right? They don't have the 60-vote majority that they need to progress the budget bill, which still is a filibuster if you just continuously vote no on the same bill to impede its progress. And it's funny. I'm not surprised by this at all, right? But it's whatever party in power has the short term view of let's get rid of the filibuster to create progress here, because this was something the Democrats were seriously discussing.

9:28I think maybe two years ago, three years ago, there was a push for the Democrats to end the filibuster for because they would politically benefit from from it at the time. And now it's twisted in the other direction where, you know, all of the Republicans that were obviously against it at that time are now, a lot of them are coming out in support of it. Sorry, this is not a, I don't think this is a unilateral thing where I think people in both parties understand the long-term consequence of eliminating the filibuster. So there's not like this entire support for this direction. But now it's being brought up at a, you know, whichever party happens to be in power and is being impeded brings up the idea of getting rid of it.

10:11But I will say not all Republicans in that Senate majority leader, John Thune of the Republicans flatly said, no, no, we're not going to do this. No, this plan like to to the question asked that Trump was proposing. And Trump was asked about John Thune saying that in the interview and basically said he was like he did like this. Well, I think that's wrong. Like, he seemed like annoyed. Like, so I don't know what kind of pressure he could put on John Thune to get that changed or that there's two different views because he also, and I'm not alarmist here, but Trump talks about, you know, the reason you don't want to do that, as you said, is that in the future, the shoe will be on the other foot.

10:55Someone else will have power. Yeah. They'll be able to use it against you. But Trump talks like that is never, he's like that. He doesn't have any. If you, if you're fully on the train right now, you don't think it's going to happen. But John Thune thinks that's real. Like he is operating under his longer term political view that eventually they'll have someone else in the Senate. But Trump does not seem to operate that way. He doesn't have any fear of that, which I thought was interesting, if not slightly alarming. The other thing we talked about is the systems that start to break around the one plus month mark.

11:28Right. And one of those things is SNAP or food stamps. Oh, yeah. And those benefits have been probably the biggest headline coming into the beginning of this month because the funding for that program through the Department of Agriculture is limited by the shutdown right now. And there was a ruling. This is a little confusing for me to follow. I read a bunch of articles over the last few days. I was hoping you could illuminate for me. I've tried to parse it as best as possible. Per usual, I would say Trump's responses on any given day make this a little harder to follow. Just a little bit of inconsistency in the messaging.

12:07But basically, it was committed that a certain amount of emergency funds available through the Department of Agriculture that are still there, that total to about 4.6 billion are going to be used to partially fund SNAP, which costs about eight to nine billion per month. And also 42 or 41 million Americans are on this program. 12 % of the American population is on SNAP in some form or another. I didn't know that. I mean, I know this going into this call or this fucking podcast. But I didn't know it when I first heard this stat in this shutdown. That is an absurd number. Yeah. That is, I did not know that at all.

12:56And not everybody receives the same amount of benefits. It varies by your income. It varies by how big your family is. So there's a range in how much you get paid out. I think the average amount that each person is receiving is something like$130,$140, I want to say. It might be a little higher than that. but so there was a commitment of that amount of funding going towards snap. And then a federal judge, there's two federal judge rulings. One of them, McConnell jr ruled that Trump has to fill the gap. No, I don't think so. That would be crazy. Trump has to use excess funds that are lying around that is available to, to him to help fund the remainder of snap okay and uh the initial reaction to that is you know tell us tell us how like i'll comply with this if you give us a pathway to like finding this amount of money it's a little confusing tariff bin um there's always money in the there's a there's always money there's always a spare five billion in the tariff bin uh and this is this is where it got confusing for me is where this money is actually from, whether or not they actually wanted to commit to it.

14:14And what are the trade-offs of that money being used? Because there's a bunch of arguments about, well, if you take this money from somewhere, then is it shorting some other program that's also limited right now? Are you withholding it just as a leverage point to use against the Democrats. And they had until Monday to comply with this demand to fully fund SNAP. And the weird thing is the initial response from Trump was basically that give us a pathway to do this and we'll do it. But then on Monday, they said, I'm actually not funding SNAP. This is on the Democrats. I'm not going to provide this extra money, which leaves the program half funded for the month and also delayed in the funding.

15:07So anybody waiting on their SNAP payments that would normally be receiving it at the beginning period of November has a delay in when they're going to receive it and also a decrease in the amount that they're getting. And the way SNAP is distributed is through the states who like define eligibility. and it's on the states to figure out the change in eligibility for money with this reduced budget that they have. So the process is very wonky right now. It's very difficult to figure out who's still going to receive money when they get it and how much they get because the program is not being fully funded, apparently because Trump is choosing not to use excess funds to fill the stopgap on what remains of the Department of Agriculture's budget.

15:52Yeah, I'm reading now. A federal judge directed the Trump administration late last month to use available emergency funds to keep SNAP benefits going. The White House said on Monday it will not be tapping into these other funds, calling it an unacceptable risk. So that is, I mean, that, I was under the impression that the judge's order had funded SNAP, but it's not the case. It was initially supposed to be the case, and it seemed like that was going to be the case. and then I forget if this was, I'm sorry, if this was this morning or yesterday, but Trump more recently came out in truth social and said, snap benefits, which increased by billions and billions of dollars, which billions and billions is all capitalized for some reason.

16:36Oh yeah. Many fold during crooked Joe Biden's disastrous term in office. I want to jump in on that line because I didn't look into this. So there was a graph that I saw of snap benefits and spending wildly up since like 2021. And I always want to know what the cause of that was. I looked into it. And the truth is, look, I'm a government spending, let's watch out kind of guy in general. But the actual math of it is just that there's a higher number of people enrolled in SNAP, which means more people need food assistance, like 12 % more. And then the vast majority of the increased spending is because food prices have gone up so dramatically.

17:11That is the vast majority is 12 % more people. And then like, you know, 70, 80 % higher food costs than things they're buying. and that combined to a dramatic increase in the amount we're spending on Snap. So it's just, you know, it's more people with more expensive food, but they're not like, the system's not being abused in some way. I thought it might have been like fraud or something, but it literally is just. I think hearing a lot of people's anecdotal experience of, you know, what it means to not have this money available to them is really heartbreaking, just at an individual level. An interesting side of this outside of just, you know, I'm struggling and I no longer get my Snap benefits and I'm unable to like put the food I need on the table, which is the standard thing we're probably all thinking of when we hear about something like this, is the opposite of maybe a small owned like grocery store or just places that sell foods or accept Snap as payment.

18:07Somebody in our Discord floor said, I'm a grocery store worker here. Grocery stores are not getting money or purchases from Snap customers. So the store is just making less money, which means less money for payroll and other expenses. So far, they're just cutting overtime hours, but we might see them cutting hours in general. So as this is maintained for longer and longer, right? The knock-on effects for all this stuff is crazy. Exactly. All of these programs that are cut, right? It inhibits the ability for people to keep people employed, and then that has cascading effects of what those employees are able to make due on.

18:38It's the same thing with the millions of furloughed workers who can't buy or spend in the way they would if they had a stable income. that stuff leads to other businesses that relied on their income cutting hiring. You know what I'm saying? There's knock-on effects I think we're only beginning to assess. And my understanding from reading about it is had this shutdown stopped immediately day 30 and they paid everybody back pay, the effects are relatively minimal. But as every day this continues on, those ripple effects start increasing exponentially. So it really is, there's a strong pressure to get it done.

19:13And I am frustrated. I also am frustrated, you know, this is a bit of a, this is a bit populist, honestly. I don't even want to say it, but I, I honest, I felt angry watching that 60 minutes interview because

19:32this is small. It's not a big deal. Yeah. There's just so much fucking gold. Every time, every fucking time I see a clip of this guy, there's more gold. it keeps getting exponential and it feels like almost like a comic book level of cartoonish level of dissonance between you can watch a clip about people on snap and then you watch someone with more gold and a 300 million dollar ballroom in the i i don't know i i it's frustrating i wonder everything's fine it's frustrating it's a frustrating thing to say uh but but you know what's funny is like i i have to assume i have to assume that that there's a electoral price for that there is so far in the polling at least like this is there are people who voted for him for different reasons that are not seeing so this is not a good look there was an interesting that uh the daily had done an episode this morning about the shutdown consequences related to snap and they're interviewing people at a food bank who would normally be snap beneficiaries right yeah and this is another thing is like food banks are where else people go for help in times like this but those systems are being strained further they don't have enough resources.

21:00Yeah. Food banks are out there. Like they're all time, maybe since the great recession, but the all time in recent years, utilization people are, there's lines. There's, you know, yeah, exactly. Exactly. And, and hearing, uh, there was a very specific woman there in West Virginia and she's talking about how she feels disconnected from Trump as somebody who voted for him now, because he was supposed to be this guy who represented and fought for people struggling in these situations. And this is, this is the working class person that was hoping that this guy would turn, turn things around for. And I know there's a portion of people who listening, who think that idea is ridiculous to begin with.

21:40And that person's like stupid for believing that, but you need to understand, like, that's the primary, you know, that's the primary block of people that were really getting behind this guy is like economic circumstances were dire for so many people and he is, for whatever reason, the guy who's going to turn that around. And now she said it in the interview where she's like, I feel like all he is doing is catering to rich people and forgetting about us, forgetting about the people who voted for him. And I don't have a poll who, I can't give you this outlook on how pervasive that sentiment is, right?

22:17But that's one person who's looking this situation in the eye at large the feedback from these people is not like the republicans or the democrats specifically are at fault here the collective reaction is more like government government do your fucking job uh and and that that was her opinion is like i this person who is struggling is being left in the dust by the guy i voted for and i wonder how much that's catching on if at all because of situations like these like how many more people feel that way when they're under this much stress to be able to put food on the table. Again, I mean, same as you.

22:52It's tough to give specifics, but I did look into it. I mean, he recently had, I don't know if this was YouGov or Newsweek, but it's his lowest poll of both terms. He just recently went under his polling at January 2021, which is right before he left office. This is after January 6th and after losing the election and during the height of COVID when America was pretty pissed. So he's 1 % lower than that on terms of approval, or I mean, 1 % higher in terms of disapproval. So it seems like there's the impact. I will say the feedback that I saw when I was reading some of the individual stories like you're talking about was โ€“ the thing they mentioned that I didn't really think about was that he talked so much in the election about domestic issues, about America, about internal, about pulling back from โ€“ But he has spent so much of his time, especially recently, traveling and focusing on foreign issues, talking about foreign issues.

23:53And this, you know, for me, I think a president kind of has to do both. But this came up a lot. People were mentioning that they felt he was not focusing enough domestically. And I do want to mention, because there was a big thing this past week with the negotiations in China. He did a trip, a whirlwind trip of Asia, meeting a lot of leaders there, and got us a truce in our Chinese trade war. I was going to give you an update on that. So how's Doug's mug sitting? How are they looking? The 100 % tariff is off. The mugs are coming, and there's still a tariff. Yeah, I was going to ask, are we back to, are we down to zero?

24:28What number have we fallen back to? We're not down to zero. I think it's, depending on the product, it's between 30 % and 47%. And I think we're back to something like May, May or June. like you know after after uh the liberation day but before a lot of the escalation it's basically a big de-escalation and i have a lot of thoughts on this because um to be honest if i have to give credit i'm not a ton of credit but it's better a better outcome than it could have been by a lot it is a de-escalation it is a walking back on both sides america walked back you know one of BIT's recent escalation, which was an expansion of the semiconductor sanctions, which were like not just the companies in China, but any company doing business with China was like the secondary sanctions.

25:18That was what escalated and caused Xi Jinping to break out the rare earth card. They both walked back that, but it is a one year truce before they make an actual deal. It's basically like, we'll walk back to May and we're going to figure this out in a year. So the real question is it's a race now between america and its allies to build a rare earth mineral uh pipeline in a year that doesn't feel versus uh china to uh make who's gonna make more progress also on rare earths or them on semiconductors on on chips that is the race uh and scott bessen was out on tv talking about how you know this was a mistake by china and we're going to use these 18 to 24 months and we're going to warp speed and we're going to build this stuff out but he also in the same interview was like china's been building this for 25 years so i don't i see a big disconnect between like you know china moves pretty fast and they spent 25 years in this we're not gonna realistically get close in a in a two-year spam but in the short term in the one you just don't believe in your country you're so wishy-washy it's not that long period of time i don't think there's something uniquely special but i it feels hella optimistic i'll be honest with you so some people have said completely different things people said this is the greatest trump said there's a 12 out of 10 deal i some people say he got totally dog walked and i've seen both and honestly it falls somewhere in the middle in that like he got them back to buying soybeans i like on a scale of dog walks to 12 out of 10 it feels more like a cautious i don't know a cautious four in my mind where it's like they're buying the soybeans um they're they're getting rid of the rare earth restrictions we can buy it for defense you could stockpile it which would be a smart thing to do but nothing's solved and a year is not a long time in the scales we're talking about a year is going to come up really quickly and i think we're going to be in the same squeeze on rare earth minerals That's what I think.

27:18That's the update on that. I don't know if you have any more. No, no. I hadn't followed what the results of the summit were. I will say two things. They had a good handshake battle. Trump and Xi, they both did a little pull and stood firm. And then Trump did make Xi Jinping laugh in a way that I have never seen. And I've watched Xi Jinping clips for coming on five years now for my show. What did he do? I don't know. I wonder if he could pull it up, Perry. Trump, like, they're all across the table. Trump pulls out something, he shows it to him, and Xi Jinping smiles and laughs like I've never seen.

27:54Like a giddy kid. Maybe it was like a first edition Charizard. I don't know what it was, bro. He was all smiles, which is, I don't know, a little charm offensive, I guess. I want to know what was on that so bad. I want to know so badly. I don't want to know what was on it so bad. I've been Googling. They don't reveal it. I wonder what he said or did. New York? Or what else? You want to talk about? Well, yeah. We could talk about New York. As of recording right now, the election isn't over. But it is looking like Momdani is going to win. Imagine he doesn't win somehow. It's the Cuomo comeback tomorrow.

28:38We look like fools. Cuomo's massive in-person last-minute voters is going to come swoop in. and take this. No, it looks like mom Donnie is going to win. I think at this stage it was very expected that he was going to win. I mean, he is the democratic candidate in New York city. And I think from a campaign perspective, it seems like he has a lot of boots on the ground support. The number of people canvassing for him was pretty ridiculous. I think it was like over 90 ,000 people he said were canvassing. So yeah, Yeah, personally, exciting to see it finally come to a conclusion. I've been seeing so much Momdani media and Cuomo stuff on my timelines.

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29:21Like it's funny that like a city's mayoral election could spend so much time occupying my feed as somebody who lives literally across the country. Yeah, on the other side of the country. but I do think this is exciting in the sense of, I really want to know how this plays out. I want to see how he fulfills the base promises that he's campaigned on, which primarily have to do with a commitment to free buses, the five grocery stores that he wants to open the freezing of a rent on a subset of apartments in New York city and universal child and universal childcare. I think those are the four things though.

30:04Those are the things that he really hammers home. He proposed a tax on the city's wealthiest residents and an increase in the city's corporate tax. This is a proposal. I mean, who knows if that that's a core part of it, but my main thing with this, it's like, this is a it's kind of a big moment, especially if this does confirm any win. It's like, it's going to be so bad if this episode comes out. It's a blowout and he lost by 40 points or something. But, you know, I think we've mentioned this, but, you know, my first initial thought is even if there was a couple of small things that I've disagreed with Mom Donnie on.

30:39First of all, he's running against fucking Cuomo. I feel like people who I've seen, you know, I listen to a wide range of political economic opinions. People I've seen criticize him, I feel like are not being honest enough about who the fuck Cuomo is. and what a low bar that is. Dude, Trump endorsed him. Yeah, that was another thing. Dude, Trump gave him, I think, honestly, the kiss of death. New York is a majority blue state and Trump last night gives him an endorsement. He got to vote for Cuomo. That is not, I could not have helped in any way. and you know i think i'm i'm excited about this cuomo himself said this like this is a war for the future the democratic party but he said it in a way where he thought he was the he's not the guy he's not the guy like he's if that's the case then i'm glad you lost i think saying like even in the world where mom donnie utterly fails at everything he's promising right either he delivers everything and for some reason it works out badly or he fails to deliver what he's promising and people don't stand behind him.

31:54It's not like Cuomo was going to be the guy who guides the Democratic Party into the light. He is the old time version of everything that people hate about the party right now, no matter who the opponent is. 100%. And the idea that he is going to be the one to move the city or the party into the future is insane to me. And that's, I don't think, I think it shows in that even the people standing behind him. Like Channel 5 just did a video where they went to a Cuomo rally of support. And every person there basically is like, I just can't, Mom Donnie can't win. And they don't like Cuomo. They have no like for Cuomo.

32:35There's no guy who's stepping up to the plate and is like, Cuomo's my guy. He's going to be the best. I haven't even, even in all of the video headlines, I haven't seen the guy. I don't know if that guy exists. I don't think so either. I have not seen it as well. Yeah. Yeah. And so I think that's what's exciting about Zoran more than anything. I agree with you. Whether or not any individual policy plan works out, I think it sounds simple, but he's young and not corrupt. Do you understand how that's the refreshing part? The bar's so low. The bar's so low. The bar's so low. Can I? And it's exciting to see.

33:18I think there's a, there's a support for him that maybe, you know, maybe I'm consuming, maybe it's the media that I watch. Right. But there seems to be a genuine excitement and support for a politician in a way that you just do not see right now there. I think that's why I'm excited and why I don't, I really don't want him to fail. Like I have faith. I think I have faith in like, he's someone I would have voted for, right? But the idea of someone like this stepping up to the plate finally, winning, and then not succeeding, I think is going to be so demotivating because people are just looking for like a trickle of somebody to hope for.

34:01And he is that guy right now. I would say, can I show my screen real quick? There is a book that I read called The Confidence Map by Peter Atwater. He talks about how confidence distills into broader society, not on an individual level, but as groups. Okay. And he talks about this way you can, uh, people are broadly seeing the world. So on the bottom axis, you have certainty from low to high on the right. Let's say you have control, how much control you feel. So basically how confident you are in what the future will look like, and then how confident you are that you can make a change to that, like have control over that.

34:35And he says, basically recently, especially young people, especially people that are probably prime Zoran voters, people have felt under this middle line of control, whether or not they're confident what the future will look like. I mean, maybe you'll feel like here, which is the worst spot to be. They have no idea what the future is going to look like and they feel like they have no control over it. But even if they feel like they know how it's going to turn out, they feel like they have no voice. Yeah. And he says, historically, when this happens, when enough people are in these areas, they almost have like a fuck it moment.

35:02They have like a fight or flight type fuck it where they jump above this line, usually to right here, no matter what. and that's what this feels like to me from um from people in the democratic party people people people are just like they want to feel like they have some agency or some control or some ability to have a voice and change and cuomo is not fucking that cuomo is the is the epitome of everything that is not of just running it down mid in the same old way it is running it down mid it is and i think they're willing to take risks basically the risk is the the biggest risk is doing nothing i think in their mind and that is why he's getting such support and so uh i what i say is you sound worried on whether or not you know some of these things work out i believe based on sort of this map it almost doesn't matter he's a he's a beginning of a broader trend do you know what i'm saying it's like it's like saying like the tea party if that didn't work out then that would have stopped.

36:03It's not about that. It is about like they, they wanted Jeb Bush and Romney out of the party. They want to take control and they did it in their own Trumpy and way on the Republican side. It's going to happen here where it's just a new group of people who have had no voice would like a fucking voice. And I think it's going to, I think it's, I think you're seeing it too with, you know, we talked about Graham Plattner, you know, Graham Plattner, uh, I think understandably got some criticism and some flashback, some pushback from, uh, revelations about his tattoo and things he said on Reddit, but the polling, especially among younger people didn't budge.

36:36In fact, it increased in some areas because they see it as he is an outside, like this almost makes him more likable because they want change. I think that, I think it's a struggle to regain agency in some way. That's what it feels like. I'm absolutely absolutely I yeah I guess my fear I do think this could be a marker of who is able to gain seats in democratic positions no matter what like is you know regardless of his like long-term success this symbolizes a change that may be happening in the long run for the democratic party. I think my fear of him not being successful doesn't even come from specifics of the policies that he advocates for.

37:25I think it's this overhanging. I've talked about this way more on the Patreon. It's this feeling that I find difficult to shake right now of there being so much like institutionalized rot that even if you come in with the best outlook and the best approach, your ability to create the change that you're looking to create feels so limited. Maybe I'm in the bottom corner of that right now. Like I don't have the agency or I don't think any person that steps into a mayoral position has, you know, no matter what they do, can fight back against the greater trends that are pushing our country or our cities or the world in what feels like a negative direction right now.

38:18That's my most like pessimistic, fearful POV. That's hard for me to shake. I don't want that to be the like thing I spread into the world and have everybody believe around me. I don't think that's good. And I think outcomes like this where 90 ,000 people get out in canvas and fight for a guy they're excited about because they want to create change. That is what I want. That is what I think is good. but you know that's it you have the the mind fear fear is the mind killer i agree wholeheartedly but i would say like you know if he is part of a broader movement that is exciting as a bigger trend on its own and if one person in one this is a big position of power but it's not a massive position of power you know even if he can't make massive change i i see it as a tide you know like a bigger a bigger shift in a direction of um people i would see just generally younger people just claiming more power like finding some way to claw into this gate kept uh system the of of boomers that i feel like it's exactly that's awesome but i feel like i feel like there's like they hold on way past expiration date i guess what you're talking about with graham is an example right it's like controversy aside i'll do anything except vote for nancy pelosi exactly like who's who's confirmed not running now i think but it's just the idea of like this old establishment like should probably be in a crypt in a pyramid politician just cannot be my guy anymore it just can't yeah it just can't and so that on it on that level alone i'm i'm excited for honestly i really i really think there's a broader movement and he's spearheading and i really give him credit for that yeah of like getting people excited about and seeing the fact that they could be represented in politics again.

40:09I think another nationally relevant vote that's going to be finishing tonight, you already voted, I'm getting out and voting, is Prop 50 in California. We covered this a little bit too, but California is changing the laws around the way redistricting works in the hopes of adding five more Democratic seats to the House of Representatives. And this is being done, to be honest, to combat an issue at the national level. I wouldn't say this is to the benefit of explicitly California. The idea is that other Republican states, Texas leading the charge, are changing the way they're redistricting to shore up seats for the midterms.

40:53And California is part of this national effort to try and combat that. And voting yes on 50 will, if you agree with utilizing our state to combat that. That's why you would vote yes on it. Yeah, we talked about it on the show. I mean, it's a dangerous, scary race to the bottom, but it is a reality that we're fighting. And it is, yeah, it is a response.

41:44I did want to end this before we get into our interview with Harley. With one more note on the shutdown. I think we've talked about, you know, planes and air traffic controllers a lot because it's probably the number one thing. I see people bring up when the subject of shutdowns comes around. And somebody in our Discord did have a response about this. They said, I just graduated from the Air Traffic Control Academy like four months ago. I got sent to Long Island and I'm currently still working without pay. I'm not actually on the floor yet, but still training for the New York airspace. I got my first zero check a few weeks ago.

42:17Is this, I mean, it's funny. It's like, is he literally receiving a check with zero dollars on it? That's crazy. And it sounds like we might get another one. Luckily, I have enough in savings plus family support for rent, but I know a lot of people who are not as stable. In our facility, more experienced controllers who have more money are lending out rent money to newer hires who don't have as much savings yet. Other than the no money, the biggest thing I have to do is to log every hour I am working plus any extra overtime pay I should be getting. The ATC union heads have said that you have to do this because whatever back pay you do will almost certainly not actually be correct to what you are owed.

42:54Turns out the people who run the books are also furloughed. so just an example of what they're dealing with on that side of things i'd also just anecdotally it of the friends who are flying right now literally every single one i've talked to has experienced delays on their last trips like in the last week yeah it's like coming up i'm i'm honestly a tiny bit nervous i'm a tiny bit i'm just picturing the most overworked old air traffic controller of all time falling asleep at their desk every day i just keep thinking about that scene from Breaking Bad, if I'm being real with you. Like, I think about it every time.

43:29Don't put that in my head. Yeah, I'm sorry. Don't put that in my head. But anyway, we have an interview. Yeah, we are interviewing the president of Shopify because they just put out their Q3 earnings. We ask him a bunch of different questions around, you know, what does an earnings call actually mean? What does it mean for the company, their past success, also the future of business in Canada, you know, how he balances his company's outlook on AI with the realities of how, you know, viewers like you engage with it. So let us know if you enjoy that. We have a little postmortem afterwards. And, you know, so hold your typing while you're watching it.

44:10Yeah, we might bring up some of the thoughts that you have while you're listening to it afterwards. Check it out though. Thanks, Harley for coming on and thanks for watching. Thank you for joining us. We really appreciate it. This is the first time we've done a call-in interview, which we've been talking about doing for a while. I'm the first. Wow. Amazing. I love that. Yeah, you get to be the first one. Yeah, if it goes good or bad. I guess it's all my fault. If I never see another remote guest, then I know, oh man, I really screwed this thing up. Very cool. Awesome. But I know your guys' Q3 earnings came out this morning.

44:50And we, I mean, we wanted to start just by having you maybe walk us through the high level of what you wanted to share about that. And then we had a couple questions about the earnings, Shopify in general, and your feeling on making such a big business in Canada specifically. Yeah, I want to set the stage a little Before you answer, just for our audience who may not know, I mean, Harley here is the CEO of Shopify, which is - President, president, president, Shopify. President, president, Shopify. This is already not going very well. And it's the largest company in Canada, not just the largest tech company, but the largest company in general by MarketCap.

45:28And you had a big earnings report today. And again, you know, for me personally, I think both of us, I'm interested to hear, first of all, what that's like. This is an insight we haven't got to hear before. This is a big day. What does that mean to an average person? What does the earnings day mean? Oh, I mean, look, I mean, to our investors that have owned our stock, you know, since the IPO, this is, I think, the 42nd, maybe 43rd earnings call we've had. We've been public for about 10 years, and there's four per year. So I think this is number 42 or 43. We went in public May 2015 on the New York Stock Exchange and the Toronto Stock Exchange.

46:05From an investor perspective, it's their opportunity to hear how it's going. What are we excited about? How have we performed? I think it's also, you know, I think ultimately publicly traded companies, what is critical is to be like any company can go public. The key though is to be a trusted publicly traded company. I think the way you become a trusted publicly traded company is it's actually very simple. It's you do what you say you're going to do. And so I think the earnings calls that happen four times a year are a bit of a check-in with the investors and the analysts that cover our stock.

46:39I don't know how many analysts cover our stock. I think it's probably in the 30s or 40s. It's a way for them to say, yeah, Shopify did what they said they were going to do or did not do what they said they were going to do. So I think from a Wall Street perspective or a capital markets perspective, it's a check-in. But from my perspective, it's just this amazing opportunity to tell our story, to update our story to the world, to people that are merchants, our partners, the media, our investors, people that are just generally interested in tech and entrepreneurship. And so, I mean, the high level numbers are, you know, we're really, really strong.

47:15We, you know, we are GMV, which is the sales on the platform, we're at 32 % year on year. Our revenue was up 32 % year on year. And our free cash show was, was, was 18%. But actually just given, you know, who I'm talking to now and in the audience that I know you folks, you know, think a lot about, like one of the things that I think is most interesting is that we put in a number today that every 26 seconds, a brand new entrepreneur gets their first sale on Shopify. So we've been talking for three minutes now. So, you know, a bunch of new entrepreneurs got their first sale. Why does that matter?

47:48It matters because, and we can get into this if you want, but I believe right now we are living in like this golden age of entrepreneurship. And part of one of the tenants of that golden age, I think is that the velocity of business growth is unlike anything any of us have ever seen. So what I mean by that is, you know, someone that just got their first sale right now, maybe their identity changed. Like they, you know, they, they went from being an aspiring entrepreneur to being a real entrepreneur. I mean, when you get that first sale from someone who's not your mom, like it, it, it's, it's, I mean, you guys probably remember that, like that first deal you got, that first sponsorship you got that first, you know, I, I sort of, I sold t-shirts all throughout college.

48:27I remember that first purchase order I got from McGill University. It was like, it was a life-changing thing, not because of the money, but because now I wasn't just aspiring. I actually was an entrepreneur. The cool part is doing that in 2025 means that someone who's starting right now may be the largest in their category in five years or 10 years. Like that velocity that, you know, I mentioned on the call, Estee Lauder is now, you know, coming to Shopify and I mentioned Michael Kors and I mentioned these incredible brands that keep coming. You know, Shopify, these big enterprise brands are on running or Birkenstock.

49:00These brands are in some cases a hundred years old, but what's also fascinating is that some of the biggest stores on Shopify today, like Viore or Aloe Yoga or Gymshark, these are like the biggest brands in their category. And I mean, Gymshark is maybe 10 years old. It was started by Ben Francis in a dorm room outside of London, England. And now Jim shark is ubiquitous. It's competing with Nike. So just from a, uh, you know, a perspective, uh, from being this, being on the show, that's why I think, uh, earnings are cool because I get to tell these stories and it's like a, it's, it's a, it's a storytelling opportunity.

49:37There's a lot to unpack there. I mean, first of all, I'll tell you, my mom still doesn't watch this show. So I'm trying to get that first. Oh, wow. I'm still aspiring. Uh, look, one of the angles I'd love to take it, if you don't mind, because I think you have an insight into the commerce here that we won't have. Your revenues is up, you said, your free cash flow is up and you're a consumer facing business at the end of the day, which means you're seeing a resiliency in the consumer that some other businesses aren't seeing. And I want to know if that's unique to Shopify or if you're seeing better signs in the economy than some of what we're hearing or feeling from your mother should watch because what a great that's a great question ask that is a deep macro you know consumer confidence question uh your mom definitely should watch uh lemonade's dent okay um so let's let's let's kind of level set here or give me her number i can call her and tell her this was all a ploy to get your mom's phone number exactly i wasn't trying to you know that sounds a little weird uh okay so uh level set so uh this quarter Q3 2025, we saw about$92 billion of products sold on Shopify.

50:47So I had mentioned we were up 32 % year on year. That's I think Shopify's ninth consecutive quarter where our GMV growth was above 20%. So when you kind of look below the hood on that GMV number, what you actually see is millions of stores that are selling on Shopify every single day. Some very large ones, Mattel, I mentioned, you know, Alo Yoga. There's obviously, you know, most of your, most of consumers' favorite brands are on Shopify. My favorite brand is James Purse. I'm wearing his t-shirt. My favorite sneakers are Tom Sachs. Those are them right there. Those are sold on Shopify also. So most of the, you know, if you're listening to this, the brands that you have a relationship with, a connection to as a consumer, most of those, all of them are on Shopify.

51:33The way that we measure consumer confidence, which is sort of what you're asking is, We measure it at checkout. Like, you know, what are we seeing on the checkout? And on Shopify, what we're seeing is that consumers are, they keep buying, they keep returning. And generally the demand has been really resilient. But there is something that I think is, is you're kind of picking on here, which is worth mentioning, which is that it does feel a little bit that consumers are being more selective, meaning like they're buying from brands that they have a connection to, that they love, that means stunning to them.

52:07This isn't just a black t-shirt. This is a James Purse black t-shirt. I've gotten a chance to know James personally. Like this guy is obsessed with making like black t-shirts. That's all he thinks about. Um, and generally those brands that, that where consumers have a relationship with, where consumers are voting with their wallets to buy from are on Shopify. So that's not to say that the entire economy, every area is going really well, but generally the people that are, The consumers that are buying on Shopify stores tend to have tend to vote with their wallets to buy from those brands. And for those selective consumers, you know, they continue to buy.

52:44I think in a time where the labor market feels so uncertain, a lot of people are either getting laid off or struggling to find a new job if they're looking for a new one. or even within the context of the shutdown in the US, if you're employed by the federal government right now, you might be looking at 30 plus days with no pay. You're kind of describing a scenario where while other parts of demand in the consumer market might be falling or struggling, you guys are providing something unique in how people can select what they buy. So you guys are still going strong? Well, so, yeah, so the answer is yes to that.

53:27But actually, I think what you're describing also is sort of the two sides of our business. One is, I just mentioned, you know, like the merchants on Shopify tend to be brands and retailers that we all love. Like, you know, I don't know what your favorite stores are. Mine are like Kith, for example, or Aloe or Viore. Those are doing really well. Those are all Shopify stores. That's not to say that, you know, Walmart is seeing the same sales that we are because, you know, the demographic that people buy from Walmart is different than those that are buying Aloe Yoga yoga pants or a Viore sweatshirt or a pair of Tekovas boots, which I think Tekovas makes the most beautiful cowboy boots.

54:05So that's on the consumer side. On the merchant side, you know, we've been leading this company now. I've been at this for 16 years, almost half my life. I'm a little bit less than half my life. I'm 41 years old. I've been in Shopify now for 16 years. What we've seen is whether it's 2008 or it's some choppiness like around the pandemic is that what people tend to do when they worry about either losing their job or they've already lost their job, or maybe they have a reduction of hours is often they turn to entrepreneurship in those moments to either supplement their income or actually to like replace their income if they've lost it.

54:41So actually, if you look at the general health of the economy and you overlay sort of business creation, not just in Canada or the U.S., but on a global level, entrepreneurship tends to work really well when people are unsure about their future. In fact, my father's an immigrant. My family, we're an immigrant family. My father immigrated to Canada in 1956 from Hungary. He was just a kid. But my grandfather, when he came here, he became an entrepreneur. He began to sell eggs at a farmer's market in Montreal. My grandfather did not call himself an entrepreneur per se. It's just like he had no choice.

55:17He had no options. And so entrepreneurship, even though, you know, what you guys talk about in a lemonade stand, what I talk about is entrepreneurship in a little bit of a glorified way that it's like the greatest way for humans to self-actualize. It's a creative pursuit. In actuality, you know, the core reason people became entrepreneurs historically was they had no choice, right? It was forced entrepreneurship rather than I think what the three of us are doing, which is more of passion driven entrepreneurship. We're choosing to do this thing called entrepreneurship, to create a show, a podcast, to run a company, to start a company.

55:51And so generally, even though it seems almost, you know, it seems like it would be the opposite, like almost like it's like, you know, it's almost a paradox. But like when people are struggling, they tend to turn to entrepreneurship as a way to struggle less. I really appreciate that perspective. And I thank you for being candid on it. I do want to press a little bit. And again, this is I know this is a difficult question to discern, especially from your position. But based on what you said about the consumer side, and again, this is not something that you created. This is something that we're just seeing.

56:23It sounds a bit like what we're hearing about. Kind of a K-shaped economy. So the K-shape or the tale of two worlds, right, is often what you hear about. And that is true, that absolutely, that some people are doing really well right now and some people are really struggling right now. um and and the ones at least again i as i mentioned earlier like consumer confidence from my perspective is measured at checkout but you know given that we you know given that we're seeing these types of growth rates given that we're seeing almost a hundred billion dollars transacted on shopify for the quarter which is up over 30 percent generally what we're seeing is that consumers on shopify which tend to be higher income consumers are definitely still buying there's one one aspect of that i didn't want to dig into though which is that So I looked at the earnings and again, all the numbers are excellent, but there was an area which, which had a growth that I think was, it was transaction and loan losses.

57:18So that those were up from 58 million to one 48 million. I don't know exactly what that means. Does that tie back into like buy now, pay later? Or is that, is there, is there a part of the consumer that is taking on more, would you say debt as part of this? No, I mean, basically we have these guardrails effectively. So we have this amazing program called Shopify Capital. Shopify Capital exists because most small businesses, I mean, so the business cannot go to the bank and say, we need money. Partially the reason that banks do not underwrite these types of businesses is because they just don't know how they're going to do, right?

57:51It's just, they don't have enough data. But we have a lot of data on these merchants. And so we're able to do like, we were able to do cash advances for these merchants. And we kind of have these guardrails in place where we believe within these guardrails, in this payback period, we can lend. So as long as they're in that guardrail, we're happy to lend. And they always are. Sometimes it will tick up a little bit higher for a particular quarter on the payback or lack thereof. But generally, as long as we're within this category or this band of what we call acceptable payback rates, we're going to continue doing that as well.

58:27It's not something that gets a lot of attention because people think about Shopify as like e-commerce or point of sale in a physical retail store or a Gentic, some of the partnerships we're doing now with OpenAI, which we're happy to talk about too. But it's a part of a business that I'm very proud of because for a lot of these merchants, they do not have other sources to get a cash advance from or for cash flow. And so we're able to say, based on your history on Shopify, we're able to extend a cash advance at this amount and, and we, you know, you pay it back as money comes back in. Okay. I understand.

58:59I mean, I would actually, you mentioned AI there. Our third co-host is normally the absolute AI bull, you know, he would love to be obsessed. Yeah. He's obsessed, but you know, I'll try to channel him for a second. Please. Yeah. I think it's interesting to hear from a CEO's perspective, especially at a tech company. What, um, what are the, the positive cases of you, AI that you're seeing or how it's helping unlock certain parts of your business. We'd be interested in seeing that. We hear both sides from a lot of people on this show and I'm interested. You hear downsides? Absolutely. Absolutely.

59:32And to be honest, that's the second part, you know, to the, to the question. Cause I assume you have like a pretty positive outlook, which I think is fair, especially from your position. But I think from the bulk of our, maybe not just our audience, but even the sea of, I would say, 20 to 30 year olds who are not, you know, not becoming entrepreneurs and not becoming, you know, not becoming a business owner. People who are just trying to get to their next job or figure out what their next day is like. AI is viewed very negatively right now. They don't see a positive effect in their life and in any real short-term future either.

1:00:12So with that context in mind of how I would say that average person views it, especially in that younger cohort, how does that balance with the benefits of it that we've also talked about on this show? I would add to that. I would just say, you know, I wouldn't say universally negative, but I'd say there's a sense of they don't see the upside yet. Yeah, everyone's a little uncomfortable. It's trepidation. Yeah, it's a little bit trepidation. And I'd love to hear. I get it. Look, I'm a consummate optimist. I think you have to be to be an entrepreneur generally because the reason I didn't become a dentist is because I think this idea of building something, no offense to all the dentists out there, but just not my style.

1:00:53I mean, I say dentist because it's a little bit more of a predictable career. Yeah, of course. So I think you have to be an optimist. Let me take it from a couple of different angles. We can talk about agentic commerce, which is like using chat GBT or using perplexity to have a conversation and have kind of a personal shopper with you, which we announced we're doing with OpenAI, but that doesn't answer the question you're asking. I'll give you this really good example. One of my mentors, one of my friends that's older than me that I really look up to and get a lot of advice from is a guy named Mickey Drexler.

1:01:25Mickey Drexler is probably as close to retail royalty as it comes. He was the CEO of The Gap for many years, 20 years. He also created Old Navy. He helped create J.Crew. he was on the board of Apple for, I think, 20 years or so as well, working very closely with Steve Jobs. So I got to know Mickey really well. And I asked Mickey about the merchandising team inside of the Gap, like the people that took product photography, that were product descriptions, that decided what goes where and how does he make it look? And so people want to buy it, what's called merchandising. And I think Mickey had said that at the peak of the Gap, there was like 300 or 400 people working, working inside of the merchandising department, um, at the gap.

1:02:07Okay. If you're a small business on Shopify or elsewhere, you can't go and hire 300, 300 people. You don't have the money. You can barely hire one person. Maybe, maybe it's your solo entrepreneur. Um, Shopify has a product. This is not a Shopify pitch, but just run with me for a second here. Shopify has a product called sidekick. Okay. Shopify sidekick is effectively this. Um, it's effectively, you know, every superhero has a sidekick. We think every entrepreneur needs a sidekick. It is effectively your assistant that works with you. That knows everything about your business and knows everything about Shopify.

1:02:38And in Q3 alone this past quarter, um, over 750 ,000 shops use sidekick for the first time. Now, a lot of these shops are small businesses and what they did, what they use sidekick for was they ran, they did analytics with sidekick. They did media help figure out like how to do replies to merchants. So, you know, if a consumer sends you an email, says, where's my package? Sidekick can actually write a reply and send it right to the consumer, right back to the consumer. It helps you, you know, you can upload a random photograph and it'll take a bunch of different photographs and it's a bunch of photographs back to you as if they were professionally done.

1:03:18If you're not sure what the product description should be, Sidekick will write it for you. If you don't know what depth, what geography a particular product is selling psychic and do that as well. That all comes like baked into Shopify for 39 bucks a month. So I showed this feature to Mickey and he was blown away by it. Not blown away because like it did things that he couldn't enter the gap. He was blown away by it because what used to take 300 people is now available for 39 bucks a month to anybody that uses Shopify. that is like people talk about leveling the playing field the people talk about the democratization of all these sort of you know buzzy terms come around but that's what it is that's what ai can do it means that you can be sitting at your mom's kitchen table and within your shopify admin you have this incredible assistant that is effectively your co-founder that can help you make better decisions faster and you don't have to go and hire more people if that doesn't get you optimistic stick about where things are going, I don't know what to say.

1:04:21I think there's two ways to look at it. One is, oh my God, I'm going to get disrupted. You've heard this. This is trite now, but people are not going to lose their job to AI. People are going to lose their job to someone who knows how to use AI, to another person who's really good at using AI. Rather than simply adopting AI, my advice to anyone listening who's an entrepreneur or small business owner is begin to use it reflexively. Begin to teach it everything you, you know, if you give, if you read an article or you give a talk or, or frankly, you have a conversation with someone that's compelling, take some notes and feed it into, you know, your chat GBT or your perplexity or your anthropic and be like, Hey, this is a really interesting conversation.

1:05:00Remember this for next time. And the next time you have something like that feed in and begin to build some context so that you actually have this like superhero assistant with you all the time. And I think when you look at it through that lens, you begin to realize that it's not that, it's not that Ben Francis and Jim Shark had an unfair advantage. It's that when you combine someone who's an incredible entrepreneur with this state of the art technology that didn't exist 10 years ago, the velocity of business growth for small businesses is unlike anything our parents or grandparents could have even dreamed of.

1:05:33I'm so dead. So sad. Doug wasn't here for that. You would have loved that, that speech particularly. I have a, I mean, I, first of all yeah thank you for that answer i i i think shopify from my outside perspective is sitting in a unique spot in this changing dynamic where i do think you do give an opportunity for people who want to dive into this new world face first i think you're you're you're democratizing something and now i feel like i'm defending ai no no no i don't want to be i don't want to be that guy genuinely these are good answers in the sense that i i think you've democratized you're helping democratize the tools of what allow people to become successful if they want to pursue that thing which you know in the past in the grand history of the world was not available to so many people exactly i can appreciate and not to say that everyone's participating but yeah more people are yeah that's right you know yeah i feel similarly about youtube years ago in a way that like right it democratized no more gatekeepers someone like me to create i couldn't create no one that's right no more gatekeepers give me a show exactly and now look what you guys have built you built something incredible and more importantly think of how many people watch lemonade standard like i want to have my own version of that and now they can do it also there is this virtuous flywheel that is happening now and it's allowing more people to not like do stuff they don't want to do but actually find their life's work which frankly our grandparents like the concept of life's work they weren't entitled to that or didn't they couldn't do it because they were just trying to put food on the table so so let's say i am you know you're selling me i guess i'm on board yeah I'm a, I'm a natural skeptic, uh, on a macro level, especially fascinating because you have an entrepreneurship podcast.

1:07:11No, it doesn't make my brain. It doesn't make it. Yeah. But the math is not mathing here. I, uh, I, you know, I think I'm actually, I'm a long-term optimist, but I, I get nervous in the short term lately. So I want to ask you some questions because I think you know more about the environment specifically, you mentioned, you know, this, this AI package that you're selling$39. People are finding great use from it. There's been a challenge, maybe not with your company, but with other companies to find revenue with some of these AI solutions. Specifically, I want to ask, you mentioned a deal with OpenAI.

1:07:42I'm seeing every three days, OpenAI is another big, massive deal, another multi-billion dollar deal with someone, whether it's Amazon or whether it's NVIDIA or AMD or Google. And there's questions about their ability to fund that through revenue. I don't know. I want to know the optimistic. I want to know a better stance of what you're seeing? Is this, it sounds like it's delivering real return for your customers, maybe as you know, on a, on a, just a personal level, what, what are the things, are the things that you're not, or, or, or is there risks you're seeing? That's more of my question is like an optimist POV, is there risks you're seeing?

1:08:13Well, look, I think so just to be clear, just to kind of set the stage, you know, the idea is agentic commerce is effectively, you know, someone once said to me that if you want to see where technology is going, look to see what like rich people do. and all of that kind of goes down to the long tail of demographics. I grew up with very little money. I've been, you know, I've been supporting myself and my family since I was 16 years old. So the idea of having a personal shopper, like I didn't, I don't even know anyone that ever had a personal shopper. Okay. But I know that people with means historically have had personal shoppers.

1:08:44Right. So I think what agentic shopping really is, agentic commerce really is, is allowing everybody to have their own personal shopper that has a full understanding of your preferences, your pricing preferences, the brands you love. And, you know, just think of this idea of like saying to, you know, to chat GBT something like, what is the best shirt to keep me cool when I'm running? And then all of a sudden it goes and searches across every Shopify store, millions of stores and products. And this is the one based on everything I know about you, based on all our search history, you should buy this.

1:09:21That is really cool. The reason that's really cool is because right now, typically what you would do is you would go to a search engine and you type in best shirt for running and you get whoever paid the most amount of money for that particular keyword, right? So now not only are you going to get results from not necessarily the, like, you may not get the biggest companies. You're going to get results that are relevant to you. You're going to find new brands that you may love, maybe a local brand, because the chat knows that you prefer to shop locally. So you find someone in Montreal for me that you're like, you know, I did this thing called 29029, which is like this Everesting race, a very cool race.

1:09:57And I wanted to buy hiking shoes. And so I was doing research. And I found a company called Norda, N-O-R-D-A. Never heard of them before, Montreal-based. It turns out, in my view, they make the very best hiking shoes. I found them because of social media and a little bit of research on a Gentic. But if I would have gone to a search engine, I never would have found them because it's a small company in Montreal. They're like, you know, a couple dozen people out of a small warehouse, you know, a small manufacturing facility. So this idea of agentic is really cool because I can say I'm having a birthday party for my daughter.

1:10:29I have two daughters, six years old and nine years old. She's really into unicorns and she's really into rainbows. And tell me everything I need to know for this birthday party. And the agentic agents, the agentic chat will say, here's everything you need. And I can one click buy all of them from across a whole bunch of stores. That is amazing. It's amazing for me, the consumer. It's also amazing for the brands that show up because now they're showing up in places they otherwise would not. Well, yeah, we, we have talked about this benefit on the show before a while ago. And I think much, I have a question, much like search engines early on it.

1:11:05I think we all probably have a universal experience of search engines, maybe 10 years ago had a better experience in finding a good, maybe not as specific or as niche as you've described. I don't think it was ever as effective as the example that you gave, but I do feel like search engines have been compromised by sponsored ads for products over time. It's become more challenging to find something like a product or a restaurant that you might want to look up than it used to be. Do you have any fear or, or, uh, any protections of how this same way of searching for things will not be compromised by like companies looking to advertise in the same way.

1:11:47Like, maybe this is the greatest feature for the next three years, but then 10, 15 years from now, my AI results are inundated with sponsor searches. Look, I don't have the answer to that. I don't have a crystal ball in terms of what other companies will do. What I do think though is like, look, social commerce seems type of thing, right? Like the reason we follow, I follow you guys on Instagram is because, you know, you guys are influencers. I know you might hate that term. And I'm like, what are they into? I don't actually know if you guys are getting paid or not. I'm just going to trust you that because I think you guys are good guys, you care a lot about entrepreneurs, you care about your audience, you care about your followers.

1:12:20If you're endorsing something, I'm going to take the leap of faith and say, you probably actually really like the product. I certainly, everything I talk about on social, like I'm not getting paid for this. I mean, you sold me on those black shirts. Your passion sold me. And I'm not getting a commission for these black shirts. And hiking shoes. I'm also not getting a commission. But the reason that you're interested is because you have no reason to think that I'm trying to sell you. I'm just telling you what I really, really like. So I do think, though, that agentic commerce has the opportunity to be more objective, to have more context.

1:12:53I think the other reason that I'm hopeful is because if I've done a bunch of research on on running and then I'm looking to go hiking, and the agent in the chat says, actually, on running is a brand new pair of hiking boots. we know you like on running because you've researched it before, that actually feels like it knows what I want. I quite like that result. I actually think some of the personalized ads that I get are really quite relevant. I mean, years ago, I used to love riding a boosted board, this motorized skateboard. I always thought about like, how are they targeting me? I was like, I like technology and I like skateboards.

1:13:27And like the Venn diagram overlap is like boosted board. I love, you know, another one is, I don't know if you guys are into like water sports, But Flightboard has like this e-foil, which I think is like a surfboard. Really, really cool. So sometimes the results that I'm getting, even if they're sponsored, I actually quite like. But I do believe that the agentic shopping model will have more objectivity and hopefully will, you know, introduce me to brands I never would have found otherwise. And I have no reason to believe otherwise. Oh, yeah. You mentioned Montreal a couple of times and we talked about the status as Canada's largest company in the intro.

1:14:06I want to know if you could give us some insight into business and economics in Canada right now. Yeah, the main thing that I had in mind here was... Not to talk about t-shirts. when you guys had uh when you guys became the largest company by market cap this year we had looked earlier in the year i'd looked at this list and i saw shopify at number two and i was like wow it's the second biggest company in canada that's that's insane and then uh looking at it more recently i was going through the list and i was like oh my god bank bank bank energy company energy company bank so with i i wanted to get a feel for your optimism for uh entrepreneurship in Canada specifically, because I think Canada has been in a rough economic spot a lot in the past few years from talking to friends, from looking at election results, all of these things.

1:15:01And I wanted to get your optimistic take on this, which I heard you're pretty bullish on Canada as a place to start a business. And I wanted to get your feelings on that. Sure. Well, first of all, you know, let's just sort of contextualize. If you look at the top 10 largest companies by market cap, um, in Canada, other than Shopify, the second youngest one is TD bank 1956. I think that's number two. That's crazy. Okay. So, uh, I am optimistic. Um, I was born in Canada, but I did not grow up here. I grew up in South Florida. Um, so I say that only to provide some insight into like, I'm choosing to live here.

1:15:44Right. I can live at this stage anywhere in the world. My wife and I, Toby and I were both living in Ottawa for the last 20 years or so. I moved to Ottawa for law school. He moved to Ottawa because he met a girl who was now his wife. We both found ourselves in Ottawa and we lived there for the last 20 years. And then sort of post-pandemic, we both decided we wanted to leave Ottawa. He wants to come to Toronto. And I was thinking about like Miami, New York. I mean, it's been a lot of time in New York City. I ended up picking Montreal because frankly, it's my favorite city on the planet. It's my wife's favorite city on the planning.

1:16:14We both went to McGill for undergrad. So I very intentionally selected to stay in Canada and very intentionally selected Montreal, which I just think is like the most entrepreneurial, cultural, interesting city I've ever been to. And I've been there now for two years. We've been living in Montreal for two years. It is one of the best decisions I've ever made. What they call the joie de vivre, like the joy of life quotient there is unlike anything I've experience anywhere in North America. Okay. So why am I opting to Canada? Well, first of all, I do think though that there is, I like the culture here, but that's not really the reason why I've stayed here.

1:16:53I think Canada suffers this tall poppy syndrome. People talk about it, but I don't think we fully realize it. If you look at companies that are built here, traditionally the path that these companies take, particularly technology companies, is they raise some money from venture capital lists or private equity funds, or in some cases, angel investors, which means they're basically committing that at some point they're going to have some sort of exit, either an IPO or they're going to get acquired. They tend to take the acquired route more than the IPO route. That's the reason why you don't see a lot of Canadian publicly traded technology companies.

1:17:30And the ones that do go public, the examples we have are like RIM, like Blackberry and Nortel. In fact, one of the things I lament the most is if you walk into any bookstore in Canada and you ask the clerk to show you some books on RIM or Nortel, it's like a row of the demise of Blackberry losing the signal. It's like all, it's like, this is a cautionary. There's not a single book that talks about what Blackberry did, which is it created the smartphone industry or what Nortel did. There's no books on Alain Bouchard who created Couchtard. There's no books on Sam Brothman who created Seagrams. There's, you know, the story of Chip Wilson and Lululemon is often not a very positive one, even though, you know, what Chip built, you can say what he wanted about Chip, but what he built is incredibly inspiring.

1:18:15I mean, he created a new category. So I think this tall poppy syndrome here, it does not serve us and is not helpful. And there's a couple of things I think we can fix here. One, I think is at the government level. I mean, you know, you mentioned that, you know, that I care a lot of this topic. I was very vocal last few weeks. The Canadian budget comes out today, but I wrote a memo about how to how basically to improve shred SRED. Shred is a program the federal government has where they give a$5 billion with a B every year at a technology companies that are doing R &D research. It turns out that 80 % of people that are filing applications to get shred use a consultant because it's so complicated.

1:18:55So what's the result of that? 30%, 20 to 30 % of the$5 billion it gets out. It goes to the consultants. Right, yeah. So like, that doesn't make sense. So we, you know. Think about the consultants. Good thing about the pool. Hold on, hold on. We don't want to leave the consultants in the street. I mean, sorry about the consultants, but like consultants should add value. That to me, I mean, it's adding value, but it shouldn't be value-add that should exist. The second thing is education. I don't think we're teaching students to like consider entrepreneurship as a viable career option, which to me is so sad.

1:19:27Like, you know, you get this list in fourth grade. It's like doctor, lawyer, accountant, magician, singer, actor, but entrepreneurship is never on the list. So I think that's part of it. And maybe kind of the last one is we have to just celebrate like our own. We have to become champions for all of us. Like, you know, I just met you guys today, but I've been talking to Lemonade Stand for a while. I think what you're doing is really compelling. And anyone that talks to me about like small business podcasts or shows that create great content i bring you up as an example of someone that i think a group that's doing things really well they do that well in the u.s they like you know they sell each other all the time we don't have to be like the americans but this idea of grow big but if you grow too big your head gets chopped off a la you know tall poppy i don't think it's working for us here's the good news i've had more engagement i've personally had more engagement with the government in the last six months than I have in the last six years.

1:20:25They seem to want to listen. We'll see what happens in terms of the results. The second thing is I see companies like ADA and League and Wealthsimple and Lightspeed and Super.com and Clio in Vancouver. And I'm seeing all these incredible Canadian companies that are getting really big and there's an appetite to stay independent, not get acquired. So I'm really excited by that. And third, if you think about funding the best investors on the planet from Silicon Valley to London, New York, California, wherever they're from, they're agnostic to geography. They're investing in the best companies. And a lot of those investment dollars are coming here to Canada.

1:21:02I mean, Wealthsimple, I think, just raised a couple of$8 billion valuation. Clio is at a billion dollar valuation. Like we're beginning to see kind of this new version of Canadian capitalism. And I think it's exciting and it's driven by entrepreneurs. That's really cool to hear. I'm Canadian myself. So I think this is a story that you don't hear from Canada very often, which is that there's a lot of light at the end of the tunnel right now of a positive future to look towards. I think that's really - Shopify plays the role of role model because of our size. That's cool. We take that seriously, but I don't necessarily, like I want Shopify to keep growing bigger.

1:21:41I also want to create, like I want that top 10 list. Okay, so we talked to top 10 in Canada. Now look at the top 10 list in the U S the top 10 list in the U S by market cap. I think most of those companies, maybe other than Apple have been created in the last 20, 25 years. I mean, Google, maybe it's 25 years ago, but like in the last 50 years, I'm pretty sure the entire list of the top 10 by market cap value valued companies in the U S have all been created in the last 50 years. Whereas there's only one in Canada. Yeah. That's, that's, that's, what do you think? I mean, I'm honestly curious. I think that's, I think, I think it's exciting.

1:22:17Cause you think about it from a Canadian, I'm not Canadian, but if you think about it from a Canadian movie, you'll never be, you know, it would be exciting to have new high growth companies in the, in the country and not have them be acquired elsewhere and not be growing in a different country. Like that, that is a positive momentum that I think is cool. What do you think? Look, success begets success. More success gets more success. you mentioned the role model effect and what do you think was different about shopify because i'm wondering why yeah i mean why didn't you go yeah because i i figured you must have faced pressure along the way maybe not an acquisition necessarily or i'm sure there were acquisition offers at some point but uh but what sort of pressures did you guys face to take the company to the u.s and why why say no along the way i mean early on a few a few venture capitalists a few vc firms had said hey, we want to invest in Shopify, but the qualification has to be you guys have to come to the US.

1:23:15But honestly, we just said no. We were building in Ottawa. We were focused. Access to talent was amazing. There was no reason to do it. What was different? I don't think we just never had the overhang of pessimism or the overhang of tall poppy syndrome. I grew up in the US. Toby grew up in Germany, and we were both building in Ottawa, Canada. I just don't think it ever crossed our mind that we would have some sort of, we would have less of an advantage being here. And now like, you know, we've millions of stores on Shopify. I'm pretty sure most of the merchants on Shopify don't even know where we're based and they don't care because what they're buying from Shopify is software, incredible, well-built, well-crafted, scalable, easy to use software.

1:23:58And you know, most people that use, I don't know, like mouthful, but like most people use Spotify don't know that they're based in Sweden. And most people that use like a lot of these sound cloud don't know they're based in Germany and they don't care. Consumers and users of our products, what they care about is, are you building something that is truly valuable? So I got, I got to run, but I just want to kind of lend, you know, and, and, and a one more thing, which is like, I think what you guys are doing and talking about and distilling and, and explaining and making small business creation and entrepreneurship just more, I don't know, accessible is exactly what we're doing also.

1:24:35In many ways, that's, I think, what we have in common is we, you know, I think one of the greatest creations of humans was the lemonade stand. Why? Because it got children, kids, to think about this idea of going to their kitchen and making this thing and then going outside and selling it. And they learned about profit margins, they learned about revenue, they learned about change, they learned about, like, the lemonade stand, I know that, you know, it's part of the brand, but at a very fundamental level, we need to create more lemonade stands at different stages of our lives to so that more people consider entrepreneurship i think the world becomes a lot more interesting if all of us are crafting things that we want to exist in the world and then consumers are voting with their wallets to buy those things so um thank you for for giving me some time thank you it's a lot yeah thank you for coming on we really appreciate it and uh yeah we'll hopefully get a chance to speak with you again have a good rest of your day and you guys should keep doing you guys should keep NBC.

1:25:29I did Fox business. I did a bunch of investor and animals called. I mean, lemonade's down. That's perfect. We're in the media circuit. Amazing. Thanks, guys. Thanks, Arlie. How are you going? Bye. We're really important.

1:25:41All right. All right. I can read between the lines. We're really important. I can see the feedback matrix before it already happens. You see the code? I know. I see the code. I see the code on the walls. And I think I just wanted to kind of post more it with you because i think there's a fair because what i'm gathering from harley is that he is really excited about the success of their business like i looked into his background before we did this interview a bit and he has been he started selling stuff he became the entrepreneur he talks about when he was 17 literally he started a business and started selling shirts at school and And I think from his perspective, right, we do exist at a time where things are being economically squeezed and it's forcing people to look for opportunity and find new things for themselves to do.

1:26:39and a lot of people are choosing to start a business in some way or another. And I do believe that in the history of things, people have been gatekept from that because of the amount of capital, your lack of tools, your lack of network, your lack of ability to easily sell things. You only have access to the town that you're in and how much you can carry on your back or in your cart to the market or something like that, right? Sure. But he has made or he has helped build a company and a tool that democratizes the availability of that opportunity. And for the people we were talking about getting, getting squeezed, like the economic squeeze, uh, he's, he's making the juicero.

1:27:22This is, that's an unfair comparison actually, cause it's a failed company. But the idea is like all of the, the maximum number of people that would want to pursue the option of entrepreneurship are available. They can pursue it because of the availability of a tool like his. And that's what he's psyched about. I think we had similar reactions to some of the things he was saying. I think we can see the reaction in real time as he's saying, it's like he's walking into oncoming traffic and we're, I get it. I'm like Harley. No, there's a rake. There's another rake, Harley. And it's, but, but I, I, I think in a lot of ways, I agree with a lot of what he's excited about.

1:27:59That's what I want to say is like, it's your squeezing example is like, I don't think this guy is the guy squeezing. Do you know what I'm saying? yeah he he's adapting to a world that is being squoze and he's giving people opportunity like i don't think i don't blame this guy i know there's a tendal sense to be like oh it's the ceo and he's you know what i'm saying but he's the president he's the president keep calling him you keep calling him the ceo that's a different guy it's a different guy should be one role he's a president i want you to know that so get it figure it out uh so i i like i seems like a nice guy and i and And in some ways, I do agree with some of what he's saying.

1:28:38And I think for some people, that is a, I mean, actually, it's factually a provable path that worked quite well. Shopify has helped some people. But I did want him, I wanted him to reconcile with the idea that no matter what, not everyone can become an entrepreneur. It's just not possible. That was the main thing I'm trying to get at there. And he is the president of a company that relies on this flow of entrepreneurship. so he's not gonna like i in his position there's no reason to not feel positive about the position that he's in and and the and the service that their company is offering and i don't discredit him for that and i don't i think the main thing when i was parsing through how i felt about what he's saying is i don't think he was saying entrepreneurship is the solution for every single person's economic strife.

1:29:29He was saying that for those who have the desire to pursue it, the tools and resources are available to you to pursue. But it did remind me a lot of that diary of a CEO debate with Gary Stevenson and the other guy where other guy just keeps saying like, you have more tools and resources to start your own business than ever. And Gary is like, they just can't all do that man and if you always tell everybody that that is their way out then people have a really depressing outlook on how their economic situation is all their fault because they just didn't become an entrepreneur and i don't think he's saying that i do not i want to be so clear i do not think he's saying that like i want to steal madame a bit in in that like he's not a politician right that he is just providing his service to people that do have that worldview exactly and so and i am the parts i like the most with the canada parts because i do think it is somewhat admirable to stay in a country like canada and help build a business there when there i think he understated the amount of uh pressure there is to do that elsewhere can i give you a like a just a personal anecdote about this is i really did i looked earlier this year the biggest companies in canada and i was very surprised to see oh my god shopify is the second biggest one right now next to all these giant Canadian banks and energy companies.

1:30:55Right. And I noticed what he said, I didn't have the exact year, but I'm like, all of these companies are old as shit and work in some ancient business. It doesn't feel like anything like flashy or innovative is really like filling out this list. But the fact that Shopify can exist there, I do think matters to people who have business ideas in Canada. Like they're, I think Canada, part of the reason it's in the economic situation it is from what I know is that they rely heavily on these old like commodity industries of like, you know, it's timber, it's oil, it's, and, and, and banking and by proxy real estate.

1:31:35And that's the economic opportunity in the country. And when you have a company like this, that's providing, you know, kind of a novel new service and breaking out and becoming the biggest globally competitive sir like it's yeah it yeah the people need that hope and and representation in that way it's funny to talk about representation in this context right but just even opening the list as a canadian gave me some hope i was like oh my god you can do it and having that bit of hope means a lot to a lot of people i'm not saying it's a policy solution to problems. And I think that's the important thing, right?

1:32:14He's not a politician. He's not writing the policy prescription for lack of affordability in Toronto. He's not that guy. He's not that guy. He's the guy offering a tool to those who wish to pursue starting their own business. I think I have a pretty wildly different worldview from that guy in general, but I had no problem hearing. I think I was, you know, the optimism is interesting to hear. and he, I don't blame him for these problems. I guess I just don't. I don't. No. Yeah. No, I don't think so either. I was excited about what he had to say about Canada the most, the fact that he has that outlook and there seems to be a growth of like new companies in the space.

1:32:56The tall poppy syndrome thing is interesting because I - You hear that about the Nordics a lot. Yeah, I mean, you hear it about everywhere outside of the US. I think this is the way that this is, all my Australian friends talk about this, all my Scandinavian friends talk about this. European friends in general, Canada also similarly, I think Canada, because of its proximity to the U S I has, I have always felt is the least like this, but I also didn't grow up. Like I didn't go to high school in Canada. Right. And I didn't go to college in Canada. So maybe I'm just the window of that is not there for me.

1:33:28Uh, so it's interesting to hear it from him and really point that out as a culture of why people don't want to push new innovative ideas there uh i've you know i it sounds like the tide is turning a bit and i think that's interesting and cool uh but i i think when he was wrapping up and he's talking about the lemonade stand thing i can already i can feel the collective eye roll i can feel it i i understand i mean part of it is like i you know that reflects a certain unfamiliarity with the show. You know what I'm saying? The idea that we're telling everybody to get out there and open their own limit.

1:34:11That's, that's the name of the show. That's fair. You know, for me it's a balance because I genuinely like hearing from people in vastly different circumstances and locations for me. Like this guy, I've always wanted to ask the CEO what's going on in their head during earning seasons. I've always wanted to ask that for a big tech company. I think that's interesting. And he, he didn't shy away when I asked him about rising loan laws. You know, you answered the question. No, I respect that. So for me, it's a balancing act where I don't, I can hear it and I have an internal eye roll, but I don't want to roll.

1:34:46I don't want to be an asshole. I don't want to be like, I think I'm saying I, I, I want, I basically want the audience to be able to hear it and understand that your worldview can stay the same. You don't have to challenge. You can just take the parts you want to hear or learn from. And I think that's fine. I think hearing him out at the end is like, what is he actually trying to say? Right. He's just, and what do you want him to say? You know what I, that's the question I would say is like, is he really going to get up there and honestly say, yeah, fucking, you know what I'm saying? He's not going to do that.

1:35:16He's not going to be like, it's fucking dog shit out there. It's fucking dog shit out there. Canada probably doomed, bro. He's not going to say that. And so like, I have your expectations somewhat said he's a, he's a, he's a, he's people in that position generally have to be like constant sources of momentum. Do you know what I'm saying? They have to constantly be like, they have to almost gas themselves up to keep things moving and going because that's, that is what their job is. Yeah. I think you kind of need to be that guy to be in that position. It's just not. Yeah. So I think take that for what it is.

1:35:50Um, I'm glad we did the call. It was interesting. Yeah. I liked, I liked talking to him. It's he has an energy for, for the work and it's fun to hear it from a company that I've actually like engaged with and use so much too. It's like, I, yeah, they make a good product. It is a useful, good product. That is interesting for you to try that, that AI thing too, because I can't judge that stuff as he's saying it. Like it sounds useful. You know, it's nuanced. It's fucking new. It's just so fucking horse shit. Everything's got to be gotten. Why is it all nuanced? Fuck. I want, I want everything. I wish, God, I wish it was black and white.

1:36:26I got, I wish, uh, as a, as a wrap up on the interview, I think this is an opportunity that we will have more. And I'd be open to hearing more questions from people that they want asked. We will have the opportunity to ask people in similar circumstances, more questions in the future. And I just want them to be ideally just well thought out in what the person is able to realistically tell us. Cause it's like, he doesn't have the answer to how do we transform society so that everyone is better off in the wake of AI. And I just didn't ask him and he's got it. He was just waiting to say it and he never got asked.

1:37:08Yeah. Yeah, I agree. I mean, listen, you know, I think we're circling the same thing, but especially with regards to AI, it's like the things that that line of logic would lead down is, is some way of redistributing the. I think people not working in Amazon warehouses is a great thing. One of my friends is working Amazon driver. He fucking hates it. He talks about how miserable he is all the time. That job doesn't need to exist as a human thing. But the benefits that accrue from having a job have to exist. And so he's not the guy to figure that out. And I agree with you that we should... If you're genuinely curious and have questions for someone like that, let us know.

1:37:53I think that's a good question for a politician. like the next politician we have on. That's, that's what I want to ask them because that's who's responsible for that. For that outcome. It's like, yeah, I don't want to shoot out on the spot on lemonade stand. Anyway, interesting guys. That's the end of our show. We'll try something different today. Different, different direction. And we'll, we'll see how it goes. Yeah. So the response, I will see you guys next week in Japan.

From the publisher

On this week's show... Aiden asks about Canada, Atrioc watches 60 Minutes, and DougDoug isn't here....so we talked to Harley Finkelstein, President of Shopify, instead.

We launched a Patreon! - https://www.patreon.com/lemonadestand for bonus episodes, discord access, a book club, and many more ways to interact with the show!

Episode: 036

Recorded on: October 4th, 2025

Clips Channel: https://www.youtube.com/channel/UCurXaZAZPKtl8EgH1ymuZgg

Follow us

TikTok - https://www.tiktok.com/@thelemonadecast

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The C-suite

Aiden - https://x.com/aidencalvin

Atrioc - https://x.com/Atrioc

DougDoug - https://x.com/DougDougFood

Edited by Aedish - https://x.com/aedishedits

Produced by Perry - https://x.com/perry_jh

Segments

0:00 Intro

1:55 Shutdown Watch

11:30 SNAP

24:01 China Tariffs

28:20 New York Elections / Zohran Mamdani

40:09 California's Prop 50 vote

41:17 Quince Promo

43:28 Air Traffic Controllers

46:05 Interview with President of Shopify

1:27:21 Post Interview discussion

1:38:12 Outro

New takes on Business, Tech, and Politics. Squeezed fresh every Wednesday.

#lemonadestand #dougdoug #atrioc #aiden
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