Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20Product: How AI Changes Product Design | Does the Design Phase Become Irrelevant in a World of Vibe Coding | The Five Pillars of Truly Great Product Design with Carl Rivera, Chief Design Officer at Shopify About this episode Carl Rivera is the Chief Design Officer at Shopify, where he previously led both Merchant Services and the Shop App as VP of Product. Before joining Shopify through its acquisition of Tictail, Carl was the co-founder and CEO of Tictail, the "Tumblr for e-commerce," where he built one of the most beloved design-forward commerce platforms of its era. AGENDA: 05:05 Biggest Lessons from Selling My Company to Shopify 09:55 Where Does Shopify Suck at Product: Lessons from that? 17:37 What makes Truly Great product Design: The Five Pillars 31:02 The Future of Design in an AI-Driven World 36:00 Do We Skip the Design Phase in AI: Figma's Evolving Role in Design 40:09 Remote Work vs. In-Person Collaboration: Where Remote Loses? 42:43 What Happens to the Vibe Coding Market 47:06 Product Management and Team Dynamics 59:48 Does AI Favour Incumbents or Startups
Transcript 13,936 words · 2 speakers
Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Harry Stebbings? This is 20 Product with me, Harry Stebbings. Now, 20 Product is the monthly show where we sit down with the best product and design leaders of our time. Today is a very special show. I was first joined by this guest over nine years ago, when he was the founder of Tic Tail, a company that Shopify later acquired. Today, he's the Chief Design Officer at Shopify, and I think Carl is one of the most thoughtful product and design leaders in tech today, and this was such a special discussion to make happen. But before we dive into the show today, on this show, we care about velocity. Most teams lose it in code review, not in writing code. Now, CodeRabbit fixes that. The second a PR opens, it leaves clear, line-by-line comments, calls out what the change might
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2:10 Harry Stebbings? Speed, you get code you can trust. The average developer saves five hours a week with Warp. That's almost half a day. Try Warp for free at warp.dev/20vc. And to get Pro for only $5 for your first month, use the code 20vc, that's 20vc. You have now arrived at your destination. Carl, I cannot believe this dude. You were episode number 10. We have now done 3000. It was actually 10 years ago. So, thank you so much for joining me again today, my friend.
2:46 Speaker 01 Yeah, we were both young and here we are, grumpy old man.
2:49 Harry Stebbings? Dude, we were both so young, but I was speaking to your co-founder before TikTok, before this show. And he said we had to start here. He said Oliver David's trademark, how does it influence your mindset? I had absolutely no idea and I have no idea what he means. So can you enlighten us?
3:09 Speaker 01 Oliver David belongs to the murky parts of my career. I was running an agency together with Kai Robin, who I then started TikTok together with. And we did a bunch of stupid things. The one thing we did was that we landed this job to basically like produce a huge event in Stockholm with a bunch of artists, like Swedish house mafia, a bunch of artists playing. And we were supposed to find like an event photographer to like document this whole experience. And we were like 18 and super young and cocky and kind of thought we knew how to do everything. So we're like, F that, like we don't need an event photographer. We're gonna document this whole thing ourselves. But the people paying us insisted that we had a professional photographer. So we made up this, this name, which was my second name Oliver and Kai's second name David.
3:53 Speaker 01 And we're like, well, we have this incredible photographer that's coming in. Oliver David's gonna shoot the whole event. And, and we had all of these like, we had to meet all of the artists in the green room. And we had to like get perfect shots of them when they were playing. And then we had to like go around with like this big set of Japanese journalists and show them around and take photos for them. And, and our photos were published in like these like Japanese lifestyle magazines under the name Oliver David. So that was my very short stint as a professional photographer.
4:22 Harry Stebbings? And it, it taught you that if you're not sure, just lie.
4:26 Speaker 01 Totally. Well, if it did help me anything, it was just like, just go, like, just go with it. Like, something great will come out and it's like, I don't know, trust your instinct and take risks. That was always kind of the engine.
4:38 Harry Stebbings? I told you this before, I'm just so happy that my research uncovered something that you forgot. That is like the ultimate compliment to me and to our team.
4:49 Speaker 01 Well, you gave me the hint. I was trying to Google this name. I was like, who is this? And then like, oh.
4:54 Harry Stebbings? Last night, I saw your comment on the G sheet last night and it was like, I don't know who this is. And I'm like, Kai, have you done me a fucking bad one? But listen, dude, there's, there's two paths where we're going to take this. We're going to take this in like the incredible story of Tic-Tail, product and lessons learned. And then also more in terms of tactical and granular today and how we think about the future of product and design. If we start on the founding of Tic-Tail, can you talk to me about the founding moment and from zero to launch there?
5:21 Speaker 01 Tic-Tail was the opposite of what we learn in lean startup and whatever. We were four guys that worked on this product non-stop, day and night, from early morning to late into the night for a year and a half. But just like a month or a month and a half before we were supposed to launch, we were able to book the largest e-commerce conference in the Nordics, the Nordic e-commerce conference. And we were like, let's launch on the conference. In fact, we know exactly when I'm going to be on stage. Let's turn our website into a timer that ticks down second for second, such that it reaches zero right when I go on stage. And let that just refresh the website and launch the product to the world. And so I was there talking about Tic-Tail.
6:02 Speaker 01 And for those of you who don't remember, which I assume is most, the goal of Tic-Tail was to build the easiest, most fun to use e-commerce platform in the world, kind of Tumblr for e-commerce. And so I go on to stage and the seconds are ticking down, start to talk, it reaches zero, the website refreshes and boom, like you can now sign up for our service. And then right there on stage, I kind of like go through the signup flow, go through like the onboarding flow, launch Tic-Tail Store number one to the world. And that was the start of this incredible startup adventure.
6:34 Harry Stebbings? Okay, I want to just unpack before we move on there. You said to me before that you were four kids with no real e-commerce experience, building from scratch.
6:42 Speaker 01 Yeah.
6:42 Harry Stebbings? Do you think having no experience in a category is a gift or a curse from a product perspective?
6:48 Speaker 01 I think being extremely naive and being extremely ambitious are like two of the most essential ingredients in building an exciting startup. And I think having no experience to the certain category that you're approaching can help create like a certain naivety. I will say that's different from having no operating experience or no clue of how you do anything at all whatsoever. And I think we managed to have kind of all of those different things going for us. Like we, we didn't have category exposure. We also didn't really have any idea of like how to build or run a company. But you kind of figure it out step by step.
7:25 Harry Stebbings? Eighteen months to launch, so to speak. That's a long time. With the benefit of hindsight, from a product perspective, again, do you recommend founders ship early and ship fast or wait for more perfect and then do the big reveal like you did?
7:39 Speaker 01 I'm super torn, to be honest. Like, obviously, it's great to ship early and ship fast. But I also do find that companies are like over MVPing products today and being lean to the point where you're no longer learning anything that's real. And I find this, if you think about like products that inspire you, it's actually really hard to come up with good examples because everyone are doing the bare minimum that it takes to get the learning. And I think the amount of quality software that exists in the world today is kind of strange and kind of depressing in a way. In that world where startups are trying so hard to narrow in on this like really tiny slice of what's going to set them apart, building a product where the journey is really
8:22 Speaker 01 considered, where you have a beautiful end to end flow, where every interaction is dialed in, is actually like a true competitive advantage.
8:30 Harry Stebbings? We have a very successful show every Thursday with Rory O'Driscoll and Jason Lampkin, and we discuss the news. And often we discuss your Harveys, your A bridges, your Lovables, companies that have raised a lot of money at very high valuations and sometimes have a lot to show for it, sometimes less so. And Rory said something really interesting. He said that the new way to win in AI is to land in a space, shout the loudest, and then build from there, but get attention first and then just build manically.
8:59 Speaker 01 Yeah.
8:59 Harry Stebbings? Do you agree with that? And have we got to a stage where actually, marketing comes before product and attention is everything?
9:07 Speaker 01 I believe that there's no right way. Like, I think companies or people and podcasters like really are trying to find like, what's the right way? What's the truth? And obviously, like, if you want to like over-market something on social media before it exists, fake it till you make it, land it, have a few users and then try to keep up with their user needs. That's certainly a way to go about it. Like, you can certainly do this and you will probably, some of you will probably figure out that path that makes you successful. I think it comes down to just like, what's the type of company that you want to build? What's the DNA of your business and what do you want to be known for, recognized for? And I think personally, I just have come to a place where I gravitate towards software that's like highly opinionated,
9:48 Speaker 01 where the builders have high conviction and want to create like end-to-end journeys that are like just cared for and like really dialed in.
9:55 Harry Stebbings? In what way do you think Shopify is highly opinionated?
9:59 Speaker 01 What's interesting about Shopify is that once you get to a certain scale, the company stops operating in one way. Like startups need to operate in one way because it's sort of this like you have tens of people working on the product. You're going to align to an operating structure and rhythm that makes sense for those like tens of people. Shopify is 10,000 people. And so we are actually not a company. We're many different companies that are kind of combined into one that are driving towards different objectives, that have different maturity levels and need different things. And so at any given time inside of Shopify, you'll find teams that are working in a kind of lean startup, ship daily, just iterate, iterate, iterate until you find the right things.
10:38 Speaker 01 Maybe over-market a few things that don't quite exist and like land the ship, build the flight while it's in flight sort of. And on the other side, we have other products and teams where we will be working on something for well over a year before we put it into the hands of our users. Because we know that what we're putting out is an e-commerce primitive that will literally change how thousands of companies run their day-to-day operations. And the cost of being wrong is really, really high then. You kind of need to be able to say, we've landed this in a way that we think we can stick to and stay with for the next decade.
11:15 Harry Stebbings? Where have you been opinionated and wrong, do you think, in the Shopify product?
11:19 Speaker 01 I think one such area for Shop might have been in developing the Shop app. For a long time, we were very, very focused on GMV being the primary metric. That's total amount of sales being the primary metric that we were driving the experience to. And of course, it's an important metric. We want to create a service that is ultimately like a net gain for our merchants. But I think it made us miss steps around the duencer journey and the engagement of Shop app. Where in fact, Shop app is as much a shopping companion as it is a discovery surface and a marketplace. And it kind of made us move so much towards the discovery side that we perhaps under-invested
12:01 Speaker 01 in the customer utility and the stickiness of the product itself.
12:06 Harry Stebbings? What do you do when a companion goes against a merchant? And what I mean by that is if you think about, say, me, I love Gymshark. And I think their customers are yours. Great, I buy shorts on Gymshark. I would probably benefit from also being shown a Lululemon top.
12:22 Speaker 01 Yeah.
12:23 Harry Stebbings? That is not in the interests of Gymshark, but it is in the interests of being a better companion. How do you think about that duality?
12:30 Speaker 01 I think it's important for companies to have principles that they adhere to when it comes to those types of considerations. And I think it's important to realize that you'll need a little bit of both. So for example, if you browse Gymshark and you browse a Gymshark store inside of Shop. We're pretty hardcore about not promoting other competing brands, any other brands on that surface. We think of their store inside of Shop app as sort of like they had their own app in the app store. It just came packed with like hundreds of millions of buyers. And so there are surfaces that we think of as like merchant-owned surfaces inside of the Shop app. But if you're browsing the feed and you're kind of like just going through like this feed of like merchant and product recommendations, then you're really shopping on a shop surface.
13:14 Speaker 01 And the job of shop there is really to just adhere to your interest and figure out what do you need right now? And what, based on your, what we know about you, what's the best thing that we can recommend to you? So for us, it's sort of like understanding what is the job that we're employed to do depending on the surface and having a strong kind of point of view on that.
13:32 Harry Stebbings? I totally get you. One is walking down the street with lots of stores available and the other is once in store, you don't provide others.
13:38 Speaker 01 Which is one of the things that makes shop a little bit unique in that like, we're not quite a marketplace. A marketplace, you go and you have merchants everywhere and they're all competing for your attention. We think of ourselves much more like a mall. You know, when you go into a mall, there's a certain kind of managed experience. The mall smells a certain way, the temperature is dialed in, it's like they're catered a little bit of like what you see. But when you go into a store inside of a mall, the merchant takes over. They have their own merchandising, they have their own staff, they speak their own language. It looks just the way they want it to look. And that's the difference, right? Like shop is a mall where like you can go into each of these stores and it becomes the merchant's experience.
14:15 Harry Stebbings? Sorry, we are gonna have some structure, but I am just so intrigued. You said about the many different teams. How do you structure product teams within Shopify? Given the many different teams, how big are they? How are they resourced? What does the reporting structure look like? Help me understand that.
14:29 Speaker 01 So at the highest level, we have areas, you would call them. And the areas are kind of like the businesses of Shopify. So think of areas being like financial services holds all of our banking, our lending products. You have POS, which is how we sell in person. You have Commerce Loop, which is like checkout and online store. You have shipping and taxes, which is how you fulfill and pay taxes with all taxes for the products that you sell. And so you have these areas and they're really like large scaled up companies in their own right. And each of these areas have leadership teams that kind of consider what's the future of my area? Where are we going? And of course, inside of these areas, there are multiple teams that then kind of like oversee kind of the different problems that come up in those areas.
15:13 Speaker 01 And so there is that sort of like organizational structure. But Shopify is an unapologetically top-down company. And so while these areas sort of have their own mandates and they have autonomy to go after their their own objectives. There's also a much bigger push towards sort of like company-wide missions and company-wide mandates. That we will be pulling these different areas together in different ways at different times. And having them form sort of virtual teams to go after certain objectives that are important. To us at any given moment.
15:43 Harry Stebbings? When you say unapologetically top down, what does that mean to you? Does that mean dictatorship?
15:48 Speaker 01 No, not at all. It's really this notion that like, we actually believe, or I believe, I should say, that we can go much faster as a company if we all go in the same direction. And that's what you get from being top down. It's like when you're 10,000 people, if you're a bottoms up company, which, you know, by the way, is the popular way to run startups for most companies. Every company comes into work and they kind of figure out what would be the best thing for us to do today. And they start going that direction. But if you have hundreds of team doing that, it's going to go like this. It's going to be a star that's pulling in every direction. And what ultimately will end up happening is that you have this strange bifurcation of experiences where one company will have three different chat services. And, and, and it's hard for them to really kind of like take big steps forward in a unified aligned way.
16:33 Speaker 01 What we have instead is that we kind of have Toby, our founder and CEO, who can come in and say, for this year, these are the themes that are most important to us. And within those themes, these are projects that I really want to see happen. And we are going to all be heading in this direction. And then we have these like rituals and processes where we check in on all of the teams and all of our progress to make sure that that's actually what's happening. That's actually what's being kind of carried out throughout the company.
16:59 Harry Stebbings? Where have you most disagreed with Toby?
17:01 Speaker 01 Oh my God. Well, over the shop years, I think we had many points of like, kind of like finding alignment of what felt like the most important and exciting future for us. I've learned a lot from Toby and Toby's point of view and outlook is very much to build platforms and to build into the ecosystem. And I think I came from a place where I wanted to have much more managed and controlled experiences. So they just the amount that we open up to merchants and to developers of taking shop and building other things on top of it, or turning it into their own, were areas where I felt way more uncomfortable.
17:37 Harry Stebbings? Do you lose design control with the transition from managed environment to platform and ecosystem?
17:43 Speaker 01 Absolutely you do, right? And you just have to find a way to be comfortable with that. And you can nudge it in the right direction by having good design systems and guidelines and so forth. But you have to give up control or else you're withholding creativity.
17:56 Harry Stebbings? How has your view on what good design is changed over time?
18:02 Speaker 01 Not that much. I have always been of the belief that good design means all of the things. Like, it's not just like, oh, it's a great information architecture or UX. Like, it's that and it's phenomenal finish. And it's that and it's really, really, really like low latency. Products that just are snappy to move, that have motion, that makes it feel more like a journey than kind of a reload. You don't feel like you belong to any certain screen that you land on. You're like just always in motion. Down to the like, the small delightful moments that you don't even count on. The feedback on touch or how a button animates after you click it. And I think having that sort of like, hey, it's everything.
18:47 Speaker 01 Like, there are no speed limits. We can just go further. Has always been kind of part of my design philosophy. And now technology allows you to push it further.
18:56 Harry Stebbings? You said earlier, we have pretty shit technology in terms of quality. I, I, I agree with you. And that's what I love, especially from a design perspective, Antoine Martin at Ammo. I don't know if you know Antoine, but from a design perspective, the way that he creates products with his team. It's just so fundamentally different to the traditional UIs that we see today. Do you feel that we have this homogeneity around design? And it's like, oh, you're doing this type of app or this type of product. This is it. And we lack that creative hallucination.
19:27 Speaker 01 You know, there's a great Paul Rand quote, which is, don't try to be different, just try to be good. I think it's Paul Rand. And I do think there's a lot to that, that like even inside of the existing form factors and what companies understand to be good interface today. We're basically like batting an average six out of 10. There's so much more to do without having to reinvent fundamentally how a nav structure works or so forth. And then I think there's like really exciting to look at concept car concepts. Like Ammo and other things where like you're really turning things upside down. And I'm open to that and I'm into that, but I don't think it's the goal. Like that, that is not the goal of like, we're an A, like a design forward company. The, the goal of a design forward company is to think of.
20:12 Speaker 01 Each of the things that you want to achieve as an app, as an experience and dial it up to a ten. Everything, how fast it is, how easy it is, how emotive it is, like the emotional experience that you take away from using that product and how it makes you feel like you're not just using a utility, you're using something that gets you, that like adapts to you and your behaviours, that's personalised. And it's all of those things.
20:36 Harry Stebbings? Does design ever go counter utility and is that a trade off you're willing to make?
20:43 Speaker 01 Design absolutely often goes counter utility. Sometimes I think deliberate friction can be a good thing. It slows things down. It allows you to actually experience what's going on, understand that this is like a high intent action or this is part of the experience that you're meant to pay extra attention to. And that, I think that's good. But sometimes design just gets in the way, that we try too hard. You're putting too much weight on the user to overcome the interface and completely learn a new pattern.
21:13 Harry Stebbings? When did you try too hard on design, do you think, within Shopify? And what did you learn?
21:18 Speaker 01 In the transition to the current form factor of shop, we had many, many misses. We really tried to find the balance between being a marketplace and having a discovery engine without losing our core of being a customer utility and a shopping companion. I tend to think that everything in the world, companies, products, people are kind of like pendulums. You swing too hard in one way and you kind of miss the green zone and you go way off to the edge and you have to swing it all the way back. And hopefully it starts to sway closer to the green zone, but it's still always swaying. And it was like that, you know, like the first attempt at marketplace, we downgraded the tracking experience, the order management experience way too much.
22:00 Speaker 01 We put a bunch of products, but we didn't have the recommendation system to back it up on the first page. So it became like this hodgepodge experience of shit, like a yard sale, no one cared about. And it was sort of that thing of like lean startup, ship fast and fix things. And it was just not the right thing. We alienated users. We didn't understand what the core proposition of. Our product was and you had to dial it in and come back to the point that shop is a mall, not a marketplace. And the curation of the feed, those should be algorithmic, should be merchant first. Then we shifted from having these product tiles to these beautiful curated merchant cards
22:39 Speaker 01 that show brands, not products, and invited you into their stores rather than trying to get you to a quick conversion on a product that was relevant to you.
22:48 Harry Stebbings? What did you learn from that then, from a product perspective?
22:51 Speaker 01 I always relearned to challenge the conventional truths. And I think a conventional truth in e-commerce is that whenever you can cut the funnel, cut the funnel. Like whenever you can remove a step, remove it. And so we did that, then we kind of go from like, you know, you have discovery, show the right thing. So you click in on the product and you convert and that's like a shorter journey. But for the role that we play in the minds of consumers and the role that we want to be playing in the world of e-commerce, the extra step, which is a long step, by the way, of getting to know the merchants and really like getting to understand not just the product that hooked you, but their entire collection of products, their merchandising, their story, was the step that made shop be special.
23:33 Speaker 01 And that was the thing that like we could never optimize away, even if it shortened the funnel.
23:38 Harry Stebbings? Can I ask you, when we think then about quality design stay and the lack of quality design stay, does that not get worse with AI and homogeneity around design only increasing?
23:50 Speaker 01 AI will multiply the amount of products that exist. And as part of that, there will be more shit products. AI will also give superpowers to companies with greater ambitions, with the interest and appetite to dial in outstanding experiences and create better products, more magical experiences than what we can even fathom right now. And so I think it's like any kind of like power curve, it's just going to split it in two where you get more shit, but also more magical and amazing experiences. And I choose to focus on the latter.
24:29 Harry Stebbings? Do you worry that discovery becomes challenging with the plethora or excess supply that you see created in market?
24:37 Speaker 01 I have for a while before AI worried that the distribution has largely settled and innovation is favoured by the larger companies again. Like when I started TikTok, so like we launched in 2012, we've like really had our moment like 2014. It still felt like this time in the market where there was a lot of like free distribution to be had for social, for advertising, for different viral mechanics, a lot of it using existing networks like Facebook to tap into them and accelerate growth. Most of those avenues got shut down or became way more expensive. And I think this shift happened where the companies that held and own distribution,
25:20 Speaker 01 companies like Meta, like Google, but also companies like Shopify started to favour where they were already established, they already had a huge user base, and they started to become just better at innovating, at creating new products, at bringing to life new experiences. And I find that to still be the thing, right? Where product discovery has been expensive for a while and it's created an environment, I think, where it's been harder for startups to cut through and most of them get picked up earlier and just integrated into larger platforms that already own the distribution.
25:53 Harry Stebbings? Do you think AI favours startups or incumbents more?
25:57 Speaker 01 Perhaps controversially, it favours incumbents more.
25:59 Harry Stebbings? Well, being at Shopify, that may not be controversial.
26:03 Harry Stebbings? Why do you believe it favours incumbents more, dude?
26:06 Speaker 01 Because I believe that distribution matters a great deal. We're all building on largely the same models. The areas where you actually can have like true network effects is access to unavailable data or consumer network effects. Both of these typically sit inside of incumbents sooner than startups. And so really the ability then is that startups are able to go after more narrow problems that incumbents are too slow to act on. And I just find that there's enough high quality incumbents in the market right now that there are fewer of those opportunities. Not to say there aren't any, just fewer. And I think that as a general kind of market trend, I believe that the incumbents are favored right now.
26:47 Harry Stebbings? Do you think the incumbents are structured to take advantage of the benefits that they actually have? I agree with you when you say about distribution, existing customer bases, trusted brand, loyalty with customer bases. But I look at a lot of them in terms of their data handling, their data quality. I just don't think that they're structured to take advantage of the immensely powerful assets that they do have. Do you agree or do you disagree? And what will separate successful versus not successful incumbents?
27:16 Speaker 01 Yeah, exactly. I think it's a case by case thing here. Like when you say incumbents, there's a lot built into that word. I think we like for years have been trained to know an incumbent as a shit company that's large. That's basically like the definition. And I just don't know that that's the case right now. Cause you have a bunch of companies that came up in an era of modern company building. I'll use Shopify as an example, but you can pick others like Stripe is a great example. And they actually have like management teams that are on it. They have founders that are super active leaders of the businesses. They're hungry, they're paranoid. These are starting to be the incumbents of the market, but they're not sleeping at the wheel.
27:58 Speaker 01 And so I think it largely comes down to like, okay, so which industry are you trying to disrupt? And who's the category leader of that industry? Is it like a sleepy CEO who is like trying to figure out how to make it another five years? Or is it someone that's hungry and paranoid and looking to reimagine and transform the company to live for another chapter?
28:18 Harry Stebbings? I remember when I had Glenn Coates on the show, who I love. I know he's a friend of yours. What a fucking great dude. But he was like, ah dude, like I'm not head of product in any way. I'm not CPO in any way, but hell no. Toby is CPO, he's head of product. Do you agree with that? And how do you analyze Toby's product instincts?
28:38 Speaker 01 It's not even a question of whether we agree with it or not. This is as close to a fact as we can possibly get on anything. I came to Shopify and I thought that I would be here through my original earn out. Three years. I'm a startup founder, an entrepreneur. I want to like go through this thing, land the team, make sure that they're off to a great start. Launch this thing that turned out to be shop and then just take another swing at it. And I'm going now, I'm getting close to seven years at Shopify and I'm not going anywhere. And the reason I'm here is Toby, because like what excites me about Shopify is that we get the distribution. We get the consumer network effects, but it doesn't seem to come at the cost of pace or conviction. And we're allowed to take these big leaps and take these bold bets.
29:23 Speaker 01 I don't agree with every bet. And sure, at some points I would have rather seen the company go in a different direction. But the trade off of saying, hey, I am actually aligned to eighty percent of his thinking. The trade off of disagreeing to the remaining twenty percent is so worth it in that I get to be part of a mission that I've been pursuing since two thousand and eleven. In a company that is so well positioned and so poised to go after it. And that is going after it in such a high conviction way. But I also always say that like Toby is the reason I'm here. And this I probably shouldn't say on a podcast, but he's the reason I'm here. And he's the reason that I one day leave. And I say that in a very loving way in that I also appreciate that at some point there might be a rift where we think so differently about the future
30:06 Speaker 01 that it's hard for me to do the best job that I can do supporting that vision.
30:11 Harry Stebbings? Seven years working alongside him, if you isolated one skill of his that makes him the multi hundred billion dollar founder that he is today. What would you say it is?
30:20 Speaker 01 It's how long term he is. You know, companies and startups like to have these like words they use. They all use the same words and it's like we're ambition led and we're long term. And we're building a generational company and blah, blah. And I said those words and I actually believed them. But then you come into an environment like Shopify and you realize they mean something else to Toby or who is acting on them in a different way. He is so long term and so faithful to the mission. And he is so willing to ignore short term gains to drive towards this global summit that he has inside. And the ability to think in those timeframes just makes him make decisions differently.
31:02 Harry Stebbings? When you think about how AI changes org structures, how does AI change the org structure of a company? I mean, your chief design officer, which is a fascinating title in itself. How does the future company structure look in an AI-first world?
31:16 Speaker 01 Well, I'll speak to it specifically for design. And what I think is happening is that you'll have a much more fluid org that is less calcified. Like, we've had this, again, default assumptions of what startups are meant to look like. And it looks something like trifectas all the way down. It's like turtles all the way down. In every level, there's like, oh, here's the big area and you have engineering, product, design, maybe data. And here's the smaller area, product, engineering, design, maybe data. And here's the area under that. And it goes all the way through the org. And I think it makes no sense at all anymore. As a designer, I believe that you are now empowered to create the opportunity space and to imagine the future, what can be, for an area that spans across the org
32:01 Speaker 01 and that produces work that can carry you for six months. And I believe that the time it takes for you to catch up on the context and to actually learn a new category is much, much faster than it's ever been before. And you think about the combination of those two. Like, you can catch up and learn a new area much faster and you can cover much more ground. The takeaway for me is like a much more centralized design team that really gets deployed not so much on surfaces or on problem areas, but that span across user journeys and span across multiple different teams.
32:38 Harry Stebbings? Is that as effective? Are centralized design teams able to provide the granularity, the nuance that a specific team would have with all the historical data and customer experiences they would have if they were only applied to that team?
32:52 Speaker 01 I think it's much more effective because I believe that the experiences that you create are no longer bound to the scope of a surface. Just think about even how you interface with like a chat G P T like in one conversation, you're going in multiple different directions. One, you're asking about the weather and then you're asking about the political climate in Argentina. It's the same thread on the same surface. And I think all interfaces are going to skew in this direction. Where like inside of the same journey, inside of the same form factor, you will want to get more jobs done at the same time. And then the other side of this that also supports this argument is that I also don't think you will need a designer for all things. Like so much of this is going to just come from vibe coding and vibe designing.
33:32 Speaker 01 I think many of the surfaces that you have a designers waste their time on today can be done just as well by a product manager with a good eye on engineering leader.
33:42 Harry Stebbings? Where do you think designers waste their time today, where they won't in the future?
33:46 Speaker 01 I'll use a dumb example, but like configuring the toggles on a settings page is really not the job that a designer needs to do. You don't need the Figma for it. Like if you have a good design system, if you have great components and you have a product manager that can think. Then you'll basically be able to say, hey, I want to create a settings page that allows you to configure the markets you sell in and the price points and blah, blah, blah, blah. And you'll have cursor or whichever tool you use build that for you. And I don't know that the design that comes out of that is going to be much worse or better than what a very good UI designer would be able to produce. And so really what I think is going to happen for design is that you'll have designers that go further down in the stack
34:31 Speaker 01 and really focuses on the design systems and the components that allows any other person to produce better design, right? If you're going to rely more on A I for the outputs, the inputs have never mattered more. So you need to like really double down on your design systems and the foundations. And then I think the other role for designers is to break all of those same systems and paint outside of the lines to create unexpected experiences where you're not doing the obvious, but you're doing the unobvious but correct and creating an experience that is like memorable, that stands out, that makes Shopify feel different than any other commerce platform out there.
35:07 Harry Stebbings? I totally agree with you in terms of like configuring the settings page. And you said a really interesting word there. You said vibe designing. Can you talk to me about how we see vibe designing entering teams and the product development process? And whether that removes the initial design phase of Figma itself?
35:26 Speaker 01 Yeah, it's interesting. I asked on my X account the other day if everyone could just share what they have in their doc right now without changing anything. And what's cool, right? Is that like for all of these designers that answered, all of them had cursor open, like effectively all of them had cursor open. And and we're seeing at Shopify, more than half of all of the design reviews I'm in are now vibe coded prototypes. They've been entirely constructed and built using our Polaris components to build it into a real prototype using real data and all of that. And so it's this huge shift and and I thought someone had a really great take on it. I can't remember who right now. Which is that Figma actually went from being the first step to being the last step.
36:05 Speaker 01 So now you have this process where you vibe design, the kind of journey, the flows, the interactions. And because you're instructing the design through code, through writing, it doesn't get to be pixel perfect. The interactions aren't quite dialed in. So once you get to something that looks like 80% complete, you kind of take that out. Then you start to like fine tune the last few details in a Figma, or if you want to go further in like an origami or something like that. And you bring it to that like 10 out of 10 level. But the bulk work is happening in a different workflow now.
36:39 Harry Stebbings? That's so interesting. Can I ask, when you look at the internal tooling, one, do you mandate any tools?
36:46 Speaker 01 No, we don't mandate any tools. The only tool that we mandate is the internal tooling of Shopify, which is called GSD, which is how we account for time, projects, tie them into missions. Make sure that everyone's moving in the same direction. That's the only mandated tool of the company.
37:01 Harry Stebbings? And then when you look at the tooling that they do use for vibe designing, what is it? Is it Cursor? Is it anthropic code? Is it lovable, Rappler? What does that look like?
37:12 Speaker 01 Inside of Shopify, the cursor is by far the most used tool in the design group.
37:16 Harry Stebbings? How price sensitive are you, do you think, to price changes in Cursor?
37:21 Speaker 01 I think Faran had a great take on this, our head of engineering, which is that the price is really not the right thing to look at. You should really focus on the increase in productivity and an increase in output. And so I think we are like fairly elastic on the pricing piece, but very, very obsessed with like the productivity piece.
37:43 Harry Stebbings? What have you seen in the productivity since?
37:46 Speaker 01 On the design side, I would say that we're probably moving at the same pace still as before. But the conversations and level of detail that we're able to get into is far higher. Five X the difference. And, and, and I expect that we will also see an increase in velocity as we become better to say, these screens aren't in the hot path. We're fine to sort of have a PM do a six out of 10, seven out of 10 like execution against this surface. And so that we can have like the design group really double down on the experiences that leave an impression that defines the product experience. And that's where I think we can see a true velocity change. But right now it's, it's really in the richness of conversations and explorations.
38:30 Speaker 01 And ultimately, I think that will translate into just more ambitious products.
38:34 Harry Stebbings? What do we do today in the design process that you think in five years' time we will look at and go, that was crazy?
38:41 Speaker 01 I find that the biggest thing that bothers me in the tooling right now, and I'll say that this applies to design, but also even in how like Shopify integrates AI through Sidekick, is how stuck you become in a modality. And what I mean by that is that if I start vibe coding a design, if I start open up cursor right now, and I'll start like designing something by prompting it, right? Like by just explaining what I want and becoming more and more detailed. But at some point I want to take a part of it and I want to pull it out and I want to have the ability to draw, to change things by hand. Then that's a completely different workflow that sits in a completely different application. And this is true even in, you know, if you look at Figma, like Figma design and Figma make are sort of like bifurcated experiences that they sit apart.
39:26 Speaker 01 And of course, this is largely due to the technical limitations of the current paradigm. But it's still the thing that it feels the most strange to me that like, I have to choose a path at the start of my process and I'm stuck to that path through the whole thing. Whereas I think people, whatever they do, they want to change between typing, talking, drawing. If you go into a room with a team, you'll be doing stuff on the whiteboard and then you'll be like turning your computer and show what you have on the screen and then you'll be talking a little bit and then maybe someone writes like, we use all of these different modalities to get to the level of detail of what we're trying to convey. And I think that's lacking in the tools today.
40:04 Harry Stebbings? You said there about the communication that you have between teams that are turning around, the whiteboarding. Do you believe you can be as effective as design teams and product teams when doing it remotely?
40:15 Speaker 01 No, is the, is the short answer. The way we overcome this at Shopify is by bringing teams together intentionally. So we will have teams come together, sometimes for a week at a time, to be in a room together, to really get to the depth of a problem, to really get all of the nuance that comes from considering ambiguity. But then, you know, at some point, you said all the things that needed to be said. And there's also something that's extremely valuable of coming back to your own environment in a hyper-focused setting where you can just go to work. And there's not a bunch of people and distractions and meetings that are being called left and right, that is like breaking your flow. And
40:58 Speaker 01 so we're trying to find the balance. And ultimately, I think it depends, as everything else, a little bit on what's the project, what's the maturity of the team, what's the stage?
41:07 Harry Stebbings? If you were CEO, Carl, would you have it as in person? I speak to many of the best CEOs in the world. Every single one behind the scenes says, remote just does not work as well. Everyone's back in person. I force everyone to be, it is like a universal consensus. If you were CEO, would you be in person?
41:25 Speaker 01 If I started a new company, I believe I would start it in person and I would have an agreement that at some level, say 150 people, we're all going to turn remote. Because I think that there's this thing that eventually the access to talent just becomes so attractive in being a remote company. And ultimately, I believe hybrid is the worst. The worst thing is the thing where like you have half of the team in person. They have an enormous information advantage. They figure out their own rituals and ways of communicating and collaborating. The other half of the team sits somewhere else. You try to come together through weekly meetings. Half of the group are tiles on the screen. It just doesn't work. And so ultimately, I think companies need to pick one of the lanes.
42:09 Speaker 01 And too many companies are ending up in both. What I think is happening is that after a certain scale, you just get so attracted to some of the talent, talent specific to the category you're going after, to the problems you're trying to solve. And they're not going to be wherever you happen to start a company, even when you start in SF or New York. And you're going to want to bring those people on. Why shouldn't you? And then you have a choice. You're hybrid or you're remote. And between those two choices, I choose remote.
42:35 Harry Stebbings? Super interesting. I actually agree with you in terms of I'll do in person until 1:50 and then I would absolutely do remote where you have to, just for access to talent. So I agree with you that if you started a new company, would you do it in Europe or in the US? And if in the US, where?
42:49 Speaker 01 Well, so I'm never going back to Europe to live. I'm American. I became American in January. I love this country. I love everything that it's brought for me and my family. The opportunities it's given me. I love the people. I love living in New York. I love that New York doesn't feel like it quite belongs to anyone. Like every person you meet, it's very rare you meet someone that actually came from New York, in New York City. I think there's a real value in closing doors as well. We especially, startup people are trained to be like maximize for optionality, like optionality, optionality, optionality. But the way that you should treat your life and how you should think about work should sometimes be different. And the way I think about life is that it's good sometimes to make decisions that you don't challenge all the time. And I made a decision that this is home.
43:34 Speaker 01 And it just removes this fan. It's like turning off the kitchen fan, like a noise in the background that goes away. And all of a sudden, you start living differently. You start making decisions on a different timeline. And that's been super valuable for me and how I approach building a family here. Of all of the places in the US, there's only really one place where I would want to live, and it's New York.
43:54 Harry Stebbings? What door did you close that you most regret closing?
43:57 Speaker 01 I don't have regrets like that. I can't say that I've closed the door that I regret closing.
44:02 Harry Stebbings? I got asked this one the other day and it was really good. It made me think, what would you do if you weren't scared? And so for me, when I thought about that, it would be move to Silicon Valley. I'm scared to move to Silicon Valley. It sounds awful, Carl, but like we'll win in Europe and we're a big fish in a small pond. And I think we're great and yeah, we'll win. But I'm scared to lose and I'm scared to lose in the valley. I'm scared to get my ass handed to me by Sequoia and the Colossus in the valley.
44:28 Speaker 01 Yeah.
44:28 Harry Stebbings? That's what I'd do if I wasn't scared.
44:30 Speaker 01 You should do it. That's what you should do.
44:32 Harry Stebbings? If you weren't scared, what would you do?
44:35 Speaker 01 Perhaps a little bit of a non-answer, but it's the thing that comes to mind. It's actually kind of what I'm doing right now with you. When I did TicTale, I was like a very public persona. I like was always out in the news. I was posting. I was doing podcasts. I was like putting myself out there. And TicTale was a great company and I'm so grateful for the journey. But it didn't land where I wanted it to land. It didn't become the success that I was driving towards. And then I came into Shopify and I sort of went into hiding a little bit. And I was like, well, I I'm tired of like saying that things are going to be great and that products are going to be huge and that I'm going to win. I just want to build products that are huge and win in different ways and like do it in the quiet, like do it away from the spotlight.
45:18 Speaker 01 And I've done that now for for seven years and I took on this new role to be CDO for for Shopify just a little while ago. As part of that role, I felt that it was important for me to start putting myself out there again. Because I have a mandate and I have an agenda that I want to drive towards. I have a vision. For I think design is going to change how we approach product development. And I want that to be said. I want that to be stated. But it felt really scary. It feels really scary. I have a note like right like in front of my computer that says something that like. Share something every day. Because the mountain I need to climb every time I post something to Twitter or to X or go on a podcast like this. It became this super scary nervous thing, a cloud that that was really hard for me to get through.
46:02 Speaker 01 And and and so these are my first trembling step out into the open again.
46:06 Harry Stebbings? You know, the biggest mistake founders make when they speak about personal brands to me, they go, it's just not me. It's not who I am. It's not how I feel comfortable. And I always laugh and I say, do you think it was me as an 18 year old in a bedroom? It's like going to the gym. You feel very uncomfortable on a treadmill. And the 50th time on the treadmill, you're actually pretty good. And it's just about repetition and consistency.
46:30 Speaker 01 Yeah, that was the thing for me of the post that's not on my screen, make yourself heard. I just need to get the reps in and eventually it will start coming easier and it will feel less awkward. And like I will feel less nervous about putting myself out there this way. But overcoming that after the tick tail journey was a hurdle for me.
46:47 Harry Stebbings? Shopify's value accretion has been amazing and the market cap today is incredibly deserved, but awesome. But it also means for the senior folks, you're not exactly there for the money anymore. Does not being there for the money change the way that you build product, design product and work?
47:06 Speaker 01 It does and it doesn't. The right answer is that it should never have affected how I built products during tick tail. I think that in my startup years, the most inspired work I did was before I had like the constructs of racing the next round in the back of my head. And you were just building product for the sake of it. Ironically, those were the products that grew the fastest and had the biggest impact. That's really the environment of Shopify that I appreciate so much that we are such a high conviction company and we are truly driving towards long-term goals rather than like next quarter earnings. But I think it's less of like being in a financially secure spot and more about being
47:49 Speaker 01 in a company environment that encourages that type of thinking.
47:55 Harry Stebbings? How do you think it does that? Is that just Toby saying, hey, you can do that?
48:00 Speaker 01 Yeah, it's basically Toby saying it, but not in those kind of words. It's more Toby getting extremely frustrated when he comes into product reviews, where he feels that the team has skewed too far into short-term thinking and local optimizations.
48:16 Harry Stebbings? How do you do product reviews and what have been your biggest lessons in what makes great ones?
48:22 Speaker 01 Shopify has a product review cadence that's very special and different in that Toby reviews actually all of the projects every month, or so every month he reviews half of them. And then the next month he reviews the other half, such that on a two-month rolling cadence, he will have reviewed every project in the whole company. And it's this huge apparatus where we come together once a month for three days, live in person, the whole executive team, but then the area leaders are coming in as they present their work. And we just go through project for project and it will go as late into the night as is required. And it's this thing that allows us to make sure that all of the work that we're doing is aligned to the mission of the company and the priorities that we consider to be the most important right now.
49:04 Speaker 01 Now, of course, between those reviews, we have a bunch of smaller product reviews that are with me or other executives. And my general outlook on these is that the way to do it is by removing all of the abstractions. I actually feel quite strongly about this. And so what I enforce with teams is that I never want to see a presentation, a slideshow, in any of the meetings. I never want to receive a pre-read. I don't want any of the storytelling at the start. I'm basically of the view that every abstraction, every insert of narratives that confuse the story brings us further away from the truth. And so what I want to do is to say, let's look at prototypes, if we have them. Let's look at real code, if we have it.
49:49 Speaker 01 If we need to use data to make a case, let's look at it inside of Looker Studio, which is the I-platform we use, or Shopify. Such that we actually look at the real data and can modify it and manipulate it if we have further questions. And let's remove all of the ways in which we can form an impression that is not the experience that our customers are going to have. And because the insight is this, right? Like, there's no customer in the history of customers that got the pre-read, that got the explanation before they opened up a product of how it's going to work, or why it's not going to work due to certain other things or reasons. And so we can get to all of those questions and the team can provide all of those answers.
50:32 Speaker 01 But we get there by actually reviewing the real work as close to the metal as possible.
50:37 Harry Stebbings? Where do most product reviews fall down in your mind, having seen a variety of different types and styles?
50:43 Speaker 01 It is when teams have gotten too stuck on the background and all of the things that led them to where they are today. Teams got too excited about the philosophy of the work that they didn't actually get into the work enough. You know, I'm not here to debate frameworks or to, you know, understand the competitive environment. I'm here to really get into the core of the experience.
51:09 Harry Stebbings? What product did you let run for too long that you should have shut down sooner?
51:14 Speaker 01 I'll give you two examples. One that is still around, but where I should have closed out the way we were approaching it in the current, you know, setting and reset. And it was the concept of KYC. And so I had just taken over lead product leadership for merchant services, which is sort of the other half of the product organization from what Glenn was responsible for. And it's like all of the add-on services, all of the payment services, the banking services, retail, shipping, taxes, accounting, all of this stuff. And I was looking at unified KYC, which is know your customer. And it was this idea that we have many different financial services and they have different underwriters. So you sign up for payments and it's powered by Stripe, but then you sign up for, you know, financial services or banking and it's, you know, powered by someone else and.
52:00 Speaker 01 We have different services that need different underwriting with different providers. But our merchants don't really think about this or experience this. They want to give KYC to Shopify once and make sure that we kind of figure out how to then distribute this data to the right providers at the right time. And I come into this new area and this feels like a fairly straightforward problem. But the team is giving me kind of a timeline that I can't agree to. And it's this hard thing, like you step into an area that you don't know that well yet. You haven't had the reps, you haven't been through all of the kind of ins and outs of the problem. But your gut is telling you that this timeline is not right. Like there's something here that someone overcomplicated and turned into too smart of a solution. And that's often the area where teams fail, right?
52:44 Speaker 01 They're trying to be too smart about the problem, trying to anticipate all of these strange corner cases. Where in fact, a simple system can scale into a complex system, but a complex system can never be simple, right? And I should have trusted my instinct. This is the thing I take away from most of my product carrier, that a lot of times the thing you feel, but you can't quite explain why. It's the gut that you should follow. You should really, like, I really believe that teams and people should trust their instincts and follow their gut much more than they do. But it's this insecurity that you assume that like the other person must know more than me. Or there's context here that I don't understand that forces it to be this way. But projects that become too complex at the onset, they can never succeed. Because complexity breeds complexity.
53:29 Speaker 01 And so as you work six months, it's like renovating a house. Like if the timeline is two years, you know it's going to take four years to renovate it. Like at some point, you just know that like when the timeline stretches past a certain point, the timelines will just keep expanding. And so what I should have done here is to actually said, you know what? You guys are a great team, super talented, but either we need to figure out how we can bring this timeline down to something that feels much more approachable. Or I need to have a different team look at this and have a different take. We avoid doing these things in teams and in companies because it feels like such a statement about the quality of the team.
54:07 Harry Stebbings? So you let it run?
54:08 Speaker 01 I let it run. I let it run. It didn't launch. And it became the thing I, you know, I worded and it became a timeline that just kept expanding, that kept leading to new, different problems and, and new approaches.
54:20 Harry Stebbings? Is that your fault or is that the team's fault?
54:23 Speaker 01 Well, I think it's my fault at a leadership level and it's the team's fault at an execution level. Like, you know, we're all at fault here. And I honestly think it's a great team and a high quality team. And they, you know, eventually were able to kind of get to a solution that we could all agree to and hold to. But just if you get a very bad prognosis from a doctor, it's like completely sociable, socially acceptable that you'll go to a different doctor to ask for a second opinion. I think you should just accept that this is how many more companies should be running their product processes. Sometimes teams just get so stuck on a specific way of doing something that it's really hard for them to see the full opportunity space or to take different approaches to things.
55:05 Speaker 01 And I believe very strongly that all problems are people problems. It's actually very seldom it's about like, oh, the brief wasn't right or the feedback came at the wrong time. It's mostly about like a configuration of people that could or could not take on a certain configuration of a problem. And more often than not, it's about them just saying, you know what, we have so many different problems to go and solve. Let's shake things up, have some of these people go look at a different problem, bring in some new fresh eyes, take a different approach and think about this opportunity differently.
55:38 Harry Stebbings? Can I ask you, what role within a product org do you think we have today that we won't have moving forwards? It changes so much. We've mentioned before how it changes the design process, the vibe coding, the product owners. What role do we have today that we won't have anymore?
55:53 Speaker 01 I think that for the foremost experts, for any role, there will always be job opportunities, but far fewer of them. And I think the general shape of the job market will move people towards being more generalists than specialists. You basically have like specialization. If you become like the best in the world, you'll always have a job market. But specialization, any point towards the middle, it's just going to go away. And it will favor generalists that can cover more ground and think more broadly about product problems. And so for instance, I announced when I took on the Chief Design Officer role in Shopify, that we're dropping UX from the designer type. And we're only going to be designers working at Shopify.
56:36 Speaker 01 And part of this for me was to articulate to our teams and to the market that we expect more of every person now. We're not going to have people that think about just the user flow or the interactions or any of that. We want you to be able to cover information, architecture, UX, Polish and prototyping all inside of one person. But when I started my career, those are four different roles. And so you have that job compression happening. And each of these tasks aren't going away, but they're being compressed into a single role.
57:09 Harry Stebbings? How does the role of the PM change? I'm always told, dude, that PMs are the CEOs of the product.
57:14 Speaker 01 Yeah.
57:14 Harry Stebbings? Does that continue? Do they still exist with the bundling of these different skills? How does that change?
57:21 Speaker 01 I think PMs will continue to exist. I think that you can have PMs manage larger teams and be more orchestrators. But ultimately, I don't like the thing like PMs are the CEOs of their teams. Because I think PMs serve the context they're in. And their job is to keep a team aligned to the direction of the company. And this idea of a CEO suggests this responsibility to actually consider an entirely blank canvas and build it in a completely independent way. I actually think their job is quite different or opposite, which is to really consider everything around them
58:02 Speaker 01 and make sure that all of the different teams are connected at the right places and are collaborating in the best ways. And in this way, you know, a PM, a large part of the role is project management. And it doesn't sound as fun and it doesn't sound as sexy, but it is a really important part of the role. I think in teams, depending on which people you have there, the aiming, the strategy, the visioning for the future can come from product, it can come from engineering, it can come from design or data, it can come from anyone. And I've seen all flavors of it. But I think it's incorrect to assume that that should always be owned by the product leader.
58:38 Harry Stebbings? What part of your role do you dislike most but continue to do regardless?
58:43 Speaker 01 It's sometimes very clear for me where we need to go and how we're going to get there. And very often, I just want to bring everyone into one meeting, basically say it once, and then have everyone be on their way. But we're in this time of change, and of course, it's breeding a lot of insecurity for everyone about the future of the business, the future for their roles, the future of like kind of their their personal identities, like what it means to be a crafter today. And I wish I could tell everyone all at once that as long as you're curious, ambitious, continue to learn new tools, you're going to be fine. But it's all going to come down to the quality of the work that we produce and put out there. So let's put our fears to the side and just be on our way.
59:28 Speaker 01 And and and I think that I do a poor job of reminding people of this and re-articulating it because it's something that is so intuitive for me, but that I have come to learn, needs constant reminding for others.
59:43 Harry Stebbings? Final one before we do a quick five, dude, I could talk to you all day, but you sent uncertainty there. There's a lot of uncertainty about the security of revenues that a lot of companies are seeing. Will it last? Is it sustainable? How do you think about whether the revenues that we're seeing a lot of these AI application layer companies have, whether they are frivolous spends by intrigued customer bases or sustainable revenues which can be tied to for the long term?
1:00:08 Speaker 01 My outlook on AI is that unlike many other disruptive technologies, AI is truly, clearly here to last and truly clearly have immediate business benefits. But because of that, we tend to kind of skim over the fact that AI is also in a hype cycle. And we are in something that is and feels a little bit like an AI bubble. And just like dot com is bigger today than it was, you know, during the dot com bubble, it didn't mean that we wouldn't have a crash or correction along the way. In fact, there will be many ones like that. And my general outlook right now, if I just think about my own spend, is that I'll sign up for anything that comes my way, just to play with it for a couple of days. I don't know that I'm going to be a Retained user six months from now, but if I was a betting man, I would say no.
1:00:52 Speaker 01 And I think the other thing that's happening is that we're seeing increasing consolidation in the market. Where these kind of core foundation models needing to live up to the very rich valuations that they already have. Are sort of pushed to take on more and more scope and bring about more and more capabilities. And they own distribution and have all of these sort of benefits that that I do all of these other utilities inside of them already. That that I worry perhaps for startups that a lot of the things that they offer. That are these sort of like niche carve out experiences for a category will be replaced by the broad based foundation models. And that many of these companies that have seen a very rapid rise. Will discover that customers think they're better served elsewhere.
1:01:37 Harry Stebbings? I want to move into a quick fire. I can't believe, by the way, I still am like shit 10 years ago, me and you were here. You know what? I was actually semi tempted to listen to the episode last night. And then I was like, just don't, because I occasionally listen when people send me stuff. And I was so bad that I just can't even listen. I'm so embarrassed. And so I couldn't listen yesterday to it, but I could talk to you all day, dude. So I'm going to say a short statement. You give me your immediate thoughts. What have you changed your mind on most in the last 12 months?
1:02:09 Speaker 01 It will be a personal answer, but I think I changed my outlook on spirituality the most. I've lived my whole life a very secular person, an atheist of sorts. And I'm starting to feel curious and excited about inviting some spiritual practice more into my life. And also I think it's as a grounding for for my kids. And I think a lot right now, I think so much about the environment, not that I want to live in, but that I want to provide for my kids. And I find that giving them something that's bigger than the context we exist in to hold on to feels like the right thing for me.
1:02:47 Harry Stebbings? What's your biggest advice to a new parent today? My brother's just had a baby for the first time, so I'm a new uncle. What advice would you give to a new parent?
1:02:55 Speaker 01 My best advice is to go for number two and go for it sooner than you think. It's so overwhelming to have your first kid. Your life gets turned upside down and so many people have the immediate reaction of like, whoa, this is wonderful, but it's a lot. But the thing that happens is that it actually isn't that much more work to have two kids than to have one. My wife jokes that it's like pulling up another chair to a dinner party. Like you're doing a lot of the same things, you're just doing now for two people. And what you fail to appreciate when you're in the thick of it with your first child is having kids that are close in ages, how much time you save later when they go off to a room to play together for hours without any kind of adult supervision.
1:03:39 Speaker 01 And it turns out it's the biggest time save you'll get, plus it's a wonderful thing.
1:03:44 Harry Stebbings? You've been with your wife for many years now, very successful, loving marriage. What's your biggest advice to me on partner selection?
1:03:53 Speaker 01 My biggest advice on partner selection is less about the traits in a person, but the appreciation that a relationship is really hard work. And I find that this is the greatest thing that's missing when I have friends that are kind of in the dating scene right now, because it's so fast to go through so many different potential partners. If I think about my relationship to my wife Baba, the first year we had together, we fought non-stop, all the time, about everything. I don't know exactly how we kind of managed through it, but we did. And it set up this foundation, we're on the other side of it. We understood each other so well. And I worry for a lot of friends again today that
1:04:35 Speaker 01 a bunch of these like people that they see could have been the right person for them, but it takes work. It takes so much work. And I think people are just hoping that they'll find like a special someone that checks all of the boxes without any of the kind of effort it takes to get to know each other and understand each other's issues and insecurities and all of that.
1:04:56 Harry Stebbings? The framework that I have is three things and you can tell me if I'm right or wrong. Number one is like physical attraction. Are you physically attracted to them?
1:05:03 Speaker 01 Yeah.
1:05:03 Harry Stebbings? Number two is intellectual capability. Do they, are they interesting, smart? You can have good conversations with them. They don't need to be a genius, but like, are they interesting enough intellectually? And then third is like laughter. Do you joke and have fun together? And if you have those three, fantastic.
1:05:22 Speaker 01 Yeah, those are great, great things to be on the look for.
1:05:27 Harry Stebbings? Okay, listen dude, I'm loving that little detour. What's the most significant life hack that you've found recently? I know you're an Oura Ring user. I know you cycle. What's the most recent significant life hack?
1:05:41 Speaker 01 So I've become much more stringent with my phone. My sleep was terrible. I didn't get sleep. Like every day I woke up and my Oura Ring told me that, hey, you basically didn't sleep tonight. And so now I've set a like really strict schedule, which is basically like I work eight thirty AM till five PM. I then go down, I have dinner with the kids. I put them to bed at seven. They're asleep by seven thirty. I then go back into my office. So when I go down to have dinner with the kids, I leave my phone in my office. So I'm like, there's no phone then. And then I come back into my office, work for an hour and a half, and then I have the sauna beyond. So then I, when I leave my office again, I leave my phone in the office. And then I go down, I do a sauna, I do cold plunge, sauna again, and then I read.
1:06:26 Speaker 01 And then I go to bed without a phone in the bedroom. And it gives me sort of an hour and a half to like read and wind down and not like think about work. And then I go to bed and, and it's been the thing that has just changed how I sleep.
1:06:39 Harry Stebbings? Does your wife mind?
1:06:41 Speaker 01 Oh, we have the same routine. We're doing this together. So she also like puts in the extra hour or so of work. After the kids fall asleep, we do this at the same time. And then we both leave our phones in the office. We go down, we sauna together, cold plunge. And then we sit in the, in the room and, and read together.
1:06:56 Harry Stebbings? Oh, that is amazing. Do you sleep much better on the back of the sauna and the cold plunge or on the back of the phone deprivation?
1:07:03 Speaker 01 I think it is the phone deprivation because what I would do is that I would like right before I went to bed, I would go through all of the work things again. And then the whole night, my brain would just be processing. I don't think it did very like, I don't think I'm very productive at work when I'm in bed right before I fall asleep. Like, I don't think I'm actually like contributing much to the business. But I know that I'm a much better team player, partner, leader. When I get like a good amount of sleep in the night and I wake up focused.
1:07:32 Harry Stebbings? Which brand do you most respect for their design principles and opinion?
1:07:37 Speaker 01 Bit of a cop out answer, but it's very nice and cool, inspiring to see the Swedish brand Teenage Engineering that have really owned and cultivated such a unique and clear form factor that is truly uniquely theirs and that they see through from the interfaces, the website that they've created, all the way down to every hardware detail on each other keyboards.
1:08:03 Harry Stebbings? Final one, why are Scandies so good at design in a way that most other nations aren't?
1:08:13 Speaker 01 I think it comes back to just a deep appreciation of craftsmanship and the pride in doing something well for the sake of doing it well. It's a country where the output isn't the growth of the thing you created or how popular it became. It's really valued in how well you practiced your craft.
1:08:34 Harry Stebbings? I once went out with a Swedish girl who taught me that there is a saying in Sweden, which is like, it's good not to stand out, like it's good to remain mediocre.
1:08:42 Speaker 01 Yeah, it's the law of Janta. It's the worst part of Sweden and part of the reason why I could never move back there. But it's, it's, it's basically the notion that no one is allowed to be better than anyone else. And it's, it's similar to a tall poppy syndrome and, and it creates these terrible social dynamics where trying to become the best is like kind of almost very un-Swedish thing to do.
1:09:05 Harry Stebbings? Dude, I've loved this. I so appreciate you. This has been fantastic. 10 years. I, I hope we don't wait 10 years for it to happen again.
1:09:13 Speaker 01 Let's do it again sooner.
1:09:14 Harry Stebbings? Thank you so much, dude. You're a star.
1:09:16 Speaker 01 Awesome. It's great to see you again, Harry.
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Previous 20VC: Sequoia's Leadership Transition | Michael Burry Shorts NVIDIA and Palantir | Gamma Raises $100M at $2BN | Has Defensibility Died in a World of AI | Datadog Surges as Duolingo Plummets: What is Happening Next 20VC: Andrew NG on The Biggest Bottlenecks in AI | How LLMs Can Be Used as a Geopolitical Weapon | Do Margins Matter in a World of AI? | Is Defensibility Dead in a World of AI? | Will AI Deliver Masa Son's Predictions of 5% GDP Growth? Page updated September 29, 2026 · transcript and summary are machine-generated
