Lenny's Podcast: Product | Career | Growth - Brandon Chu on building product at Shopify, how writing changed the trajectory of his career, the habits that make you a great PM, pros and cons of being a platform PM, how Shopify got through Covid

Episode Date: June 27, 2022

Brandon Chu is VP of Product at Shopify, where he leads the app platform ecosystem, new initiatives group, and M&A investments. Brandon helped scale Shopify’s PM team from five to hundreds, and worked his way up from an IC Senior PM. Prior to Shopify, he was a Director of PM at FreshBooks and, before that, a founder. Brandon might be best known for his writing on the art and science of product management as part of a collection on Medium he calls “The Black Box of Product Management.”—Thank you to our sponsors for making this episode possible:• Stytch: https://stytch.com/• Persona: https://withpersona.com/lenny• PostHog: https://posthog.com/lenny—In this episode, we cover:1) Brandon’s path to VP of Product at Shopify.2) What has Brandon found to be the most important skill set for super-successful PMs?3) What is it like to build product at Shopify?4) How did Shopify adjust after the shock to e-commerce during Covid?5) How did Shopify build a one-click team offsite flight/hotel/activity booking platform?6) How did Brandon motivate himself to start, and keep, writing?7) As a PM, why is writing one of the highest-ROI uses of your time?8) What’s Brandon’s favorite piece of writing?9) What are the biggest surprises, pros, and cons about being a platform PM?—Where to find Brandon:• Twitter: https://twitter.com/brandonmchu• LinkedIn: https://www.linkedin.com/in/brandonmchu/• Brandon’s writing: https://blackboxofpm.com/• Making Good Decisions as a Product Manager: https://blackboxofpm.com/making-good-decisions-as-a-product-manager-c66ddacc9e2b This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

If you're a product manager, you've almost certainly come across one of Brandon Chew's Medium Posts. His writing about all aspects of the job is some of the best writing out there on the skills of being a PM and has informed a lot of my thinking on both product management and writing. Brandon is currently a VP of product at Shopify where he's been for seven years and in our conversation, we talk about what it's like to build product at Shopify, what Shopify has learned about being effective working remotely, having done it from day one. The importance of writing on one's career and how to get started, the benefits of becoming a platform PM, the manager track versus the IC track, and a bunch of other stuff.

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You can also enrich that information to automatically see if the person exists on various watch lists. Just go to with persona.com slash Lenny to get started. Brandon, thank you so much for joining me. Hey, Lenny. Thanks for having me. I'm curious. When you were younger, what did you want to be when you grew up? An astronaut. Say more. I've always just had a longing for space.

Like, I have a vision in my mind, and I still think I'm going to do this. Like, one day I'm going to see like the whole earth in one view. And it's going to make me feel, this is going to sound weird, but make me feel really small, which I think will make me feel connected. And so, yeah, even since I was like 16, I've been saving $2,000 a year in a separate account that I just like, you know, invest in the market. because I calculated that it would cost like half a million dollars by the time I was 55. And I think it's going to actually work out like timing-wise because it's like the cost is coming close.

This is an amazing story. That's like a very PME way of approaching it, just like start putting my way. I guess so. Plan for going to go into space, hoping that tech would catch up. This is going to be a great podcast V2 when you're on your way to space. Yeah, we'll do it for sure. I'll bring my Starlink up there. I just got an email from Starlink that you can now move your Starlink around and get internet as you move.

Oh, that's amazing. So they're going to have a mount on Teslas and you just plug it into your Tesla and just, yeah. Exactly. It's all coming together. Okay, so you wanted to be an astronaut, eventually got into product. I'd love to hear. I like that segue. I got into product initially and then just kind of your journey to where we are today, which is VP of product at Shopify. So way back in university, I kind of grew up actually in the era where people really wanted to work on Wall Street still. So I actually came up through like the finance ranks and stuff like that. And I worked in industry at craft foods of all places. for about four years. But how I kind of broke into product management is I got really bored of that really quickly.

And I started moonlighting and bootstrapping a startup on the side. And it was called Tunesi. And it helped YouTube musicians at the time, which were blowing up. This is kind of when Justin Dever was becoming famous by doing like webcam, cover music and stuff like that. And we helped YouTube musicians monetize their fan bases by offering fan experiences at their tour stops. And so this is really early. This is before YouTube even had like a music category. And so my co-founder and I, neither of us were technical, but we were pretty good at pitching.

And so we kind of entered a lot of startup competitions and we got some funding and some office space. And we quit our jobs like literally the weekend after we won that. And then fast forward three and a half, four years. We never really made a really big company out of it. But we kind of soft landed, sold the company. And I'd say that's my first foray because my job as a co-founder there was really into work with that engineering and design. And it was through that experience that I learned everything about product.

And I got a lot more technical too. I was able to do a little bit on the front end. And so from that, after the acquisition and the integration, I parlayed that into product management career, basically. So I joined a growth stage startup in Canada in Toronto called FreshBooks, which is still around today. They're like a series D company now. And I kind of learned the chops of product management there

because the folks there were like X Microsoft 15 years, you know, really technical, process-oriented and framework-heavy product management. I had my just scrappy entrepreneurial experience. So I kind of hardened my PM skills through that over about four years. And then I joined Shopify the week of the IPO, actually. So that's almost seven years ago. And it was like one of the largest companies I'd ever worked at, at 500 people even then, you know, at least because I'd been in startups prior. So I thought maybe the story's over. But, you know, As I met Toby through my interview process, I realized that that was definitely not true, and it obviously is not true now.

So, yeah, it's been seven years there, various PM roles, areas of the product, and then eventually really started to build some domain expertise around platform, management, and developer ecosystems, and kind of grew my career there into that domain, became a product director, and then a VP of product. And then in classic Shopify form, I completely threw it all the way and started something a little different inside the company 18 months ago. So now I lead what we call product acceleration, which is the team that does all of Shopify's, investments, and M&A. Amazing. So I was looking at your LinkedIn and just hearing this story, especially the Shopify piece, it's a pretty incredible

trajectory. And I imagine a lot of people listening to this may be like, shit, how do I follow a similar path? How do I do it? Brandon did. Do you have any advice about what it was that helped you, either habits, skills, behaviors that helped you get to where you today that maybe newer PMs could learn from? I think, like, what I learned over the arc of my career is that, especially when it comes to product management specifically, it's a lot of the hard skills that PMs are known for. So like organizational, analytical, good communication, even technical skills, they're sort of table stakes and commodities to be an entry level PM. And to be clear, like, it's not easy to be a PM. it's not an entry-level job.

And so, you know, that is no knock on that. I'm saying to grow beyond that, though, I think, like, domain expertise can take you a little bit further, like if you're an amazing payments PM or you have some really, you know, nuanced knowledge and whatever, 3D modeling or something like that. But I think ultimately to have, like, the highest trajectory and what certainly, you know, was a tailwind for my career was,

you guys have to lean into those founder skills. And so things like being a great storyteller, how to get the most set of people around you, foster creative and motivated teams, and know how to make really, really hard, high conviction decisions that actually can't be solved. Like, you've got to take a leave of faith and how to do that and bring teams through that type of ambiguity. And then how to leave by example and have accountability when you make those choices. So I found that ultimately those really became the things that were limiters for some careers I observed. And then were definitely propellants for a lot of the people that made it to high level of leadership.

Awesome. And I know you wrote a. a lot about a lot of these things, which we'll talk about your writing, which I'm a huge fan of and have been a fan of for a long time. But before we get into those, I want to chat a little bit about Shopify and your experience at Shopify and just understanding the product culture at Shopify. As an outsider, Shopify feels like an incredibly strong product culture. And I know a lot of amazing PMs that work there. And even outside PMs, just generally amazing people. What would you say are some of the defining characteristics of how teams built product at Shopify?

maybe that are different from how other companies approach product? Shopify has an incredibly strong product culture. Whether it's uniquely different, I can't know for sure. But I would say, like, I'd start with it. It's a highly technical company. That's not unique, but it's just something that, you know, should be known about Shopify. When I joined, like, all project management was just in GitHub, just commenting on poll requests. And even marketers in order to, like, augment or upload a blog post, you'd have to, like, commit and deploy it.

So there was no breaks given for folks that, you know, they didn't want to touch code and stuff like that. I think it was very much, and this all stems from Toby, you know, a very well-renowned developer in the Rails core community. And it all kind of flowed from him. And so because of that, I think everyone in the company had their hands really deep in the product, like regardless of what function you are. And which brings me kind of the second thing, I think is really awesome of which Shopify when it comes to how the product org works. It's that we don't actually put the product org on a pedestal as like the only people that can have an opinion about the product or should be listened to when we think about what should be built. There's sort of an understanding of shop by that like everyone at the company from engineers to support to sales, like everyone's responsible for product thinking. And it's not just, you know, the area for a small group of PMs.

And so that's some of the foundations of it. And all, again, all stems from Toby. I'd say the last one is that this comes from the fact that we have like Canadian roots. And I say that actually in a way that's almost opposite of the stereotype when it comes to tech anyway. Like there has been a lot of failed tech companies in Canada and no company that's ever truly being global. And so ambition and a founder mentality has been something that we've architected the culture of the product team around. And so 30 to 40% of the PM team are ex-founders, either through, failed startups or through acquisition.

And, you know, this is really important to us, you know, for obvious reasons about just versatility and grit and growth mindset. But then also, like, we are building a platform for other entrepreneurs, whether they're merchants on our platform or developers to build their own stuff. And so we have a lot of empathy for our customers through that. And so the way this is all kind of coalesce is like, you know, the one-liner job description we give to PMs as they come in is sort of your job is to help teams ship the right thing at the right time and the right way. And it really comes down to like two main concepts there.

It's like help teams. So it's like servant leadership. You're not necessarily the CEO of the product or a dictator. Like everyone's responsible for product thinking and you're there to help the team get to ultimately the right thing. And that is what you are accountable for. I love that definition. In practice, do you give PMs a little bit more sway over decisions or do you try to keep it completely equal amongst functions? Actually, I think it depends on the level So I think, like, as you go to more, it's more like the junior PMs and the ICs, like, there is a much bigger emphasis on balanced decision making between all the crafts, like user experience and engineering, of course. And then it's more when you get to, like, director level or above. Like, that's when there is more emphasis put on where the PM wants to lead because ultimately it becomes like a pure strategic function at that point.

And that is your only job. Your only job is to say, like, we need to go there and, like, my ass is online for us going there. And so, you know, that is something I think we matured into. There was obviously lots of tension as we grew of like, hey, you know, we used to collaborate, but now you're saying like, we have to do this thing. And it's like, well, actually, the company, the context changed, my role changed. And we have to do something. And it has to be someone's job to make that choice.

So it's a bit of both is the answer. Awesome. Spending a little more time on decision making in general at Shopify. Is there kind of like a framework or a specific process? process you guys use to make bigger decisions? What we do have is like an annual planning cycle, basically. We call like investment plans. And it's for fairly large swaths of the organization.

I'm talking like 20% chunks of all of Shopify, consolidated under a VP here and there, to put forward a vision for what that team's going to accomplish that year, whether that is like a directional change or even specific outcomes in some cases. And we spend time aligning with both. you know, Toby, the rest of the C-level exec team, even sometimes the board on what that is and, you know, what headcount may go with that and whatnot. But that's sort of like the main arc of planning. Like what happens after that is just chaos. Because chaos, like all the teams underneath and like I said, you know, one fifth of shop five may be moving towards one investment

plan. That's at this scale like almost 2,500 people, right? So they're all now chaotically moving towards those end goals and iterating through ideas, good and bad. And so this is actually where Shopify is a really hard place too, because we do this because we recognize a couple things. One is like, it's important that we set broad direction so everyone can put their energy towards the right place. But we also want a place where, you know, we're hiring smart people so that they can figure out what to do.

And we also know that in software and in tech and in this world, things change so rapidly. So don't even kid yourself that we're going to plan out everything we're going to have to do for the next year to get there. And so we set this directional kind of outcome and vision-based kind of North Star for where we want to go. Then product directors start to basically shoot their shot and say, like, this is how my group can contribute to those things. Here's what we're going to try to commit to in the next quarter, basically.

And it's through that almost like back and forth, the Truss Battery thing that I was talking about plays in again. Like they're selling it to their peers, you know, the engineering directors, they're selling it to the VPs, they're selling it to the broad team as well to get momentum behind it and to say like, you know what this feels right? Let's start doing that. But what's really amazing and also difficult to watch out by though is like we're pretty good at never falling in the sunk cost fallacy. So we'll throw it all away anytime if the world changes. Right. And so that's why it's actually a really tricky place for a lot of folks because there

are cases and it's happened to me many times where it's just like, you know, you're building three, six months into something and like, It's just not important anymore or the world changed. And so that's kind of how, like, you know, the sausage gets made. And like, it really comes down to, like, giving teams, the agency, giving product folks, you know, at certain levels, the responsibility to make a bet. And then having the humility to understand that, like, stopper's hard, the world changes. And that we always have to ask ourselves, this is the most important thing that we can do right now. It's so important.

A lot of companies just, like, want to avoid upsetting people, want to avoid creating chaos. And it's so important to always be rethinking, even if it's like we just put a plan together. Maybe we should change it because things have changed. And so I'm not surprised Shopify is really good at this. To give an example, like during COVID, this cultural resilience we had to change was so vital because all of a sudden these grandiose ideas and visions we had for 2020 didn't matter. And what mattered was like, oh shit, retail businesses are going from 100% to zero. It's like zero percent revenue overnight.

And how do we help a brick and mortar store across the street now do like order online and pick up in store? Right. Like how do we do that? How do we like throw away everything? This is what matters now. Let's try to ship three things in the next month that matter. And like that's very jarring, I think, unless you have a culture that just understands

that can happen any day. And it kind of gets excited by that. I'd love to actually hear whatever you could share on the COVID period of Shopify and just what folks did to work through that. Yeah, I mean, we threw all the roadmaps. We asked ourselves like, hey, like our customers, like their livelihoods are at risk right now. And this is like, you know, when no one knew it would actually be a tail win for e-commerce, right? We didn't know the severity of COVID.

Like it could have been a really, really bad pandemic from a death rate perspective. So like no one's better. And like, oh, everyone's going to stay home for two years and everyone's going to buy stuff online, right? Everyone's like, okay, all our customers are going to go to zero unless we help them. figure out how to actually survive through this. And so, you know, of course, online only merchants or merchants are well established online have that infrastructure. There wasn't supply chain issues yet. So, like, they're good. The focus then turned, of course, all of these both hybrid brick and mortar online customers and customers that were only brick and order. And so we did all those things like,

you know, some restaurants and grocery stores on the platform. How do we help them do exactly that, like buy online, pick up at the curb? How do we help them launch, like buy gift cards now at a discount so that basically you can as a consumer help these companies stay afloat like if you recall back in 2020 like that was a huge thing like buy gift cards at the restaurant you like because if you don't it might not exist I did that a bunch I remember yeah and so these things exist on shop buy in apps because they were never really like you know mission critical but now it became really mission critical so all of a sudden we're like trying to gear 500 people to work 500 people to

awards like, you know, ship gift cards, which sounds like a really small feature, but it's pretty hard when you have, you know, millions of merchants and hundreds of millions of consumers using your platform every day, you know, ship it in two weeks. And so it became more time, truly. And like, yes, Toby got way more involved as did Craig Miller or CPO at the time. And, you know, we went down from trying to ship maybe the 40 things that quarter to like free. And nothing else mattered. And that became sort of the rhythm of the company for almost that entire year. Wow. How long did that kind of wartime period last internally?

I'd say the edge came off a little bit, I think, like mid-2020. Like, it wasn't that long ago, actually, maybe about a year ago, that it started like, I would say it never really left wartime per se. But it sort of became like everyone sort of adjusted to it. And so many other things were happening because we had often. is before, and we made the decision very early in the pandemic to say, like, we're never going to have offices again. We're a digital by default company, higher anywhere in the world.

Let's make sure we have really great infrastructure. And so there are so many things happening inside the company that just changed overnight. Shopify, the experience, the culture of the company changed overnight. And so it's hard to say when it stopped. It just evolved. I wanted to actually ask about that. And so I'm glad you brought that up the fact that Shopify's been very remote for friendly for a long time. I imagine it's rooted in the fact that it was founded in Ottawa,

and it's probably hard to hire the scale of people that you're all hiring out of Ottawa. And I imagine there was an advantage to having a lot of that experience working remotely in this new modern world. And I also imagine it wasn't like easy still. But what I'm curious about is what sorts of things have you learned about working remotely that you can share that other companies can maybe learn from from Shopify's experience? You know, funny enough that in person still matters. It does. And that doesn't mean we're rolling back at all, the fact that we're remote only. But what we've done is we've actually instituted with something we call bursts.

So bursts at Shopify are the ability for your team, you know, generally like maybe once a quarter or whatnot, to just come together to do really high-velocity creative work together, to hang out together. And so we've gone like pretty far on this where we actually have like in-house built web and mobile apps that allow teams to like one-click. say I have like 20 people. We want to do a burst in Laguna Beach and then click the button and then like flights get booked, hotels get booked. Food is taken care of. No one has to pay like any, like there's no expenses that go back and forth.

The app itself helps you check into those places. And we have really cool experiences. And like in France and Ireland, I'll leave a little bit to the imagination. But it's really cool. So, you know, we started allowing. kind of that as the world opened up for travel and like now teams are doing it all the time. I'm going next week actually to one with our team. Can you just do a personal burst?

I just want to go to Bahamas first. You could try. I mean, we've done other things too. Like, you know, because you spoke of Bahamas. Like I actually worked out of the Caribbean for five weeks in March. And because we also had a policy that we instituted that said for 90 days out of the year, you can work in any country you want. And so what we tried to do with a remote only world is like we tried to turn all the

weaknesses on its head. and to say like, okay, well, we can't see each other every day, but let's remember all the ways that, you know, that's sucked from a commute perspective. And like, even when you were together, if you were just working in your desk and never even talking to each other, that wasn't great. So why don't we just like optimize for the stuff that was amazing about it

and make it super easy and fun? And that's what bursts became. And then, hey, we don't want, you know, we have amazing infrastructure now. We can work with global teams 24-7, 365. Why are we forcing people to like stay in a look? I mean, the reality is the 90A thing is mostly because of like a tax thing. But ultimately, like, we have the infrastructure that people can just log in from wherever.

And so why not lean into it? Yeah, this is really interesting. I love that your answer to how to work remotely better is get together more often, which I hear a lot from companies. But I love that you've built this infrastructure to enable it. I'd love to hear a bit more of how this product works. Is it all in-house? Any advice, I guess, for anyone trying to build something like this? I hate saying that it is all in-house because that is not easily accessible for mid-sized or below companies.

But basically, you initiate an event called a burst. You can choose what type of thing like you're trying to do, whether it's like a pure work thing or you want to have a little bit of activity and social aspects of it. There's different locations, depending on how many people are going that are available to you. There's a booking system. If you choose to do something, you know, a little more low-key and just meet in, let's say, a major city, then we actually allow you to access our old offices. So the leases then go away. So we had to use these offices for something. And these offices have now completely been retrofitted. They're beautiful. And they are like, you know, amazing. I wouldn't even say co-working spaces. There's community spaces now that you go in and you can use them and like you have everything. Like there's food there like there used to be. There's, you know, there's. know, boardrooms and whatever you want to have your little offsite or whatever maybe.

And then there's like a rating system after how was the burst there. There's a whole team that manages the logistics of all these things. So that it's very just like we don't have, you know, managers all over the company trying to like figure out flight plans and stuff like that. And yeah, it's great. And we also get the data to be able to see like, hey, what teams haven't been together in a very long time and like, ask the lead like, hey, why is that? Like, is it because everything's good?

And like, you know, people are busy. Maybe something about it. or something like that and they can't get around, or is it a prompt that, hey, maybe your energy is low as a team and it's time to get together. So that's the benefit, I think, of having built that app and that infrastructure is that we get to really understand how it's actually helping. This episode is brought to you by PostHog. PostHawk offers a suite of product analysis tools, including funnels, heat maps, session recording, and experimentation, all in one easy-to-use platform. Post-Hawk is open-source so you can host it on your own infrastructure, which means that you have

control over who has access to your data and makes regulatory compliance a breeze because you don't need to send user info to third parties. Post Hogg's app system works seamlessly with your data warehouse, both for importing and exporting data, which enables you to bring your data into one place and easily understand user behavior across a range of touchpoints. If you'd like to learn more, check them out at post hoc.com slash Lenny. Just one last technical question about this product is it's so cool. Is there an API that just books flights, or does it just send you to kayak and you book these flights?

I don't know the exact answer, but I would imagine. So we also use trip actions inside of Shopify, and I'm pretty sure they have an API. So probably we've done something directly with them. So they've handled all the, like, really complex stuff, but we probably use them for the booking action itself. Okay, sweet. This is super interesting. I've never heard of this. I want to transition to talk a little bit about your writing.

So your writing is how I originally discovered you. It's in the top, I don't know, 1% of most useful, actionable, interesting writing on the craft or product management. I still refer to it often. I share it with people all the time. And it does a lot because it's a little older at this point and you've kind of slowed down the writing. I'm curious when you're in that writing phase. A lot of people want to write. A lot of people know that it's good for many reasons, but a lot of people don't do it.

What would you say worked well for you when you were in that period to get you to actually get stuff written? also just create time for writing. Yeah, well, first of all, thank you. That's like super generous. I think like, you know, if you say I'm in the top 1% then Lenny, you're definitely in the top 0.1 or 0.01%. And also thank you for being generous saying like I've slowed down a bit. Like the reality is I haven't been anything since 2010. So, you know, when I reflect on it, I think I wrote those in a time where I was figuring out a lot of stuff while I was executing and I wanted to like crystallize

in my mind some mental models and frameworks that had been forming somewhat intuitively. Like the funny thing about those posts when I reflect on them and I rarely read them but every once in a while, you know, someone shares an excerpt and I end up kind of rereading and be like, do I even believe this still? But, you know, when people read them,

they think like, oh, they're learning from someone who's figured it out for a while and, you know, now they're sharing it later in their career or something. but the reality is, and maybe this resonates with you, it's like, I figured out everything in those posts at the exact moment I wrote them. It was the writing process itself that actually allowed me to solidify those mental models and this frameworks in my mind. And so I wasn't, you know, ahead of the game in any way. It was just, I think I really wanted to, like, disambiguate the chaos in my mind about what my job was. And it took me to really interesting places.

And I think it was also coupled with two things, which was like I had a really good career trajectory. at the same time. So I could actually observe, like, I wasn't too mired in like being a PM1 for five years and then moving. I was like moving through things really quickly. So I was able to contrast things because it was literally like, oh, wait, three months ago, it was that. Now how do I change? And that, of course, is not just me, but it's also because shop I grew so much during that time. Right. Like, we grew seven years ago, it was, I came at just under 500 people, were over 12,000 people today. And so it was a really formative time for the whole company and definitely myself. And in terms of just like writing well and shipping quality posts and stuff like that.

Like, you know, I'm sure this resonates with you. You just got to put in the work. You got to put a lot of hours. Like, I'd put, you know, 40 hours into a post. Do it on the weekends. Or like, I brain dumped a first draft of it in two hours and it would do 38 hours of editing. Right? Or getting feedback from people or drawing some shitty diagrams that I put in there.

But it was that process. And I think, like, it was such an amazing thing to learn how to do is to like just sit and write for five hours and reread the thing and actually also get feedback from people. Like, don't be so afraid to share raw early thoughts and for it to kind of not make sense. But then when you give to someone an objective and they read it, they'll be like, you really learn things about how you put a narrative together in your mind versus how someone actually reacts to it. And so, you know, that fearlessness to get a lot of feedback, I think, was something I developed through those years. Everything you said is 100% resonates with my approach.

there's a quote I often think about it might be Hemingway or might be misattributed to Hemingway that I don't know what I think until I've written it down. And that's exactly how I feel. Like it's a forcing function to help you actually figure out something. And that's exactly how I started. And it's a release too because when you write it down,

it actually you just kind of release it from your mind. It's not floating around there because I'm scared to lose it or something like that. And you kind of just like, now you clear your mind and you can actually think you build on top of that knowledge into something else. That's exactly how I felt when I first started writing. I just want to get these things out of my head before I forget them, partly to help crystallize something that I can actually hold on to that won't fade away. Okay. How many posts have you written now? I think probably 300. 300. How are you still motivated to or where do you even find things to write about now?

So I have an endless list of things I want to write about. And partly these ideas come from founders and PMs that are constantly sending me questions that they have. And the way I see it is until nobody has any more questions to ask about starting company, building a product, driving growth, I'm going to have things to write about. And it feels like that's an endless supply. The bigger challenges, it gets hard and harder because the easier stuff is getting knocked out. And so that's the bigger challenges. Things remaining are more things that take more time, more research, more Ging and things like that. But at this point, yeah, I've been doing it for over three years and still got plenty of ideas. And there's no better motivator than somebody paying you for your content

and in charge. Well, it's a symbiotic relationship, right? All those questions and feedback from your subscribers and whatnot is fodder for the next thing that you're going to give. And I think that's an amazing relationship. That's exactly right. I wanted to ask you, do you think every PM slash leader should spend time writing? Who should? Who should? What's you feeling on that? I think yes. Even if it's not. to be like publicly shared or whatnot. I think ultimately like especially in a increasingly digital world and increasingly remote world, you've got to be able to articulate yourself. Again, like even going back to that process of writing and what it does for how you understand what you're saying,

you owe your team, your peers, your stakeholders, that level of clarity. So even if you're right it and throw it away, you've created the clarity in your mind and you can articulate it as such and people deserve that. And I think that if you're going to be a really good PM, you have to have that skill. What impact have you seen as a result of your writing that you've done? Oh, it's like honestly been the most important thing I've ever done in my career, unbelievably.

It has had probably two really interesting effects. One is that as Shopify grew and like, you know, when we were going through hyperscale, you probably recognize this from your Airbnb days as well, but like people are falling from the sky. Every day, there's 20 new people showing up. and like, you know, you having been there already, like now you've got to figure out what all these people are doing

and give them all these types of things and like how do you even teach them like the culture and the ways that you work and stuff like this. And so one amazing, and like just the context, like I'm really old at shop by now. I'm like 99.1% tenure. So I'm like ancient at the company. Is there a stat that shows up?

Is there like a little dashboard? There is in our little internal wiki thing. So I'm literally ancient in the company. And so one of the amazing effects that the, the writing had was that people that would join my team already knew how I thought. It was pre-onboarded, a lot of the PMs that would join my team because, like, you know, obviously they're going to look for who their leads is and Google that a bit. And they see a posting and be like, you know, this is this person legit or not or whatever.

And so I didn't really even have to onboard many people in so many ways. Like they kind of knew like how I thought about the world. And also even when I was in Shopify and writing those posts, There's so much noise in shopping. It's a very chaotic place. There's so many exciting things happening that it is very hard to like tell 200-person PM org, like, stop, pay attention to this idea. Right. So I actually found that writing externally and getting momentum externally was a better way to influence internally what was happening.

Like to the effect that like Toby would read my post here and there. And he'd be like, great post. And I'd be like, hey, daddy loves me. But no, but seriously. You know, it would help build my trust battery with Toby. because of the way that those posts gain traction and whatnot. So it has had an incredible, incredible impact on my personal career. And also I think, like, it has brought a lot of really great people to Shopify.

Like literally every week, I new PM messages me and says, like, hey, I just joined, you know, your post had a lot of influence on me or whatever. And like, you know, I'd love to meet up and blah, blah, blah. But, like, that has, it's been amazing. And it's so rewarding. Another small example, this wasn't in the Black Box project management, like, general. Canon or whatever per se, but I was working on the integration product with Facebook Messenger via Shopify. And like as part of our launch, I wrote just to get more, because we're a very small company

of them. So we're using any angle we can. So I'm writing on my personal blog about this thing that we launched. And David Marcus, who's now like leading, you know, their blockchain crypto stuff, but he was CEO of PayPal for a while. And then he came in to lead like all the Facebook's payment stuff and Messenger. Oh, sorry, to lead messenger. And he shared a, he shared a on his Facebook and on Twitter, and then that blew up. And, you know, all of a sudden the CPU of Shopify, like Craig or whatever, now starts thinking I'm legit, even though, you know, because someone like, you know, of his caliber was also like sharing these things about a product that we built and whatnot. So like, it was just like, it was really interesting how these little things had an impact

on how people perceive you and thus how much impact and momentum you can create inside a company. if you think about it, say you spend 40 hours on that post, what R.O. Why, that is, spending like a week or two writing something and the impact that could have on your perception within the company on your future career opportunities and even just people joining the company that are going to work for you. They're like, oh my God, I'm going to work for Brandon Chu. I'm so excited. I mean, I'd say like even if you never got picked up, the R.O.I. is already huge because it just, again, helps you refine how you talk about the work and decisions. But that's, aside, like, it accelerated my career probably a decade.

That's a really good point. You should not be focused on this needs to go viral for this to be worth the time. Because I find that the more you think about that, the less, well, it does because that becomes the wrong intent. Yeah. Well, that's, you know, to be perfectly transparent about it, like, it is a factor in why it's not right. It had gained so much traction and I was so, like, I had become an exact now at Shopify and I was so busy at them. I was like, I don't have the time to make this thing as good as it was. And, And I'm not even going to put another post out because I just, I don't want to disappoint people. Like, that's a real thing.

I think you're probably better conditioned to this. Like having written 300 posts now, I think, like, you know, you're a machine. But for me, it was like I would put one every couple months maximum or something like that. And so when I lost the time, I had kids and all these types of things, like, it seemed insurmountable to prioritize. I wanted to ask, what's your favorite thing that you've written? Which piece is your favorite? I don't know if I have a favorite, but the one that always just like, I'd say has overall had the most traction or just like constantly, even to today,

people still tweet about it or message me about whatever, was the one about making good decisions as a PM. Basically, the short of it is like the first thing it argues is that the most important thing to figure out when you're dealing with any decision is actually like figuring out how important that decision is, right, since we're faced with hundreds of decisions in any given moment around the product or whatever and that we're only human and we can only prioritize a few you know, you've got to figure out the importance of them so you can prioritize. And so it talks about things like, is the decision reversible or not?

Does it affect a lot of users in a material way or not? Stuff like that ways to kind of like prioritize them, basically. And then it kind of argues that, okay, given the fact that we only have limited time and that the most important decisions are so much more important than the other 98, 99 of them, you should basically spend all your time on those very few important decisions. And for all other decisions, you should literally just go with whatever your gut is, or delegated. Because it's just like, you're only human. And like, your gut is going to be right, a decent amount of time too.

And so, like, just make those fast so that you can keep the team velocity high. You never want to be a blocker. That's the other tension. And then spend all your time on these, like, few critical decisions. Would you say that's still generally the way you work? looking back at that post? Yeah, definitely is still the way of work. You probably do it too much in terms of use my judgment.

It's like, ah, that isn't important. Because I think over time, too, you get weathered down about, like, what's actually like super dire versus not. And like, you know, once you've had a few battle scars of things that you thought were like going to ruin everything, your career, your reputation, blah, blah, blah. And then like, actually nothing happened. You just start to raise the bar about what's actually important. I love it.

We're definitely going to link to that in the description for this episode. Is there a post that you wish you had written or want to write if you have the time? I've been wanting to write literally for three years. It'll probably be really long, but just like a huge post about being a platform PM, as opposed to a product being. And there's so many interesting differences in the ways that you have to think about prioritization. And like I even told a story about like, you know, it's a big cultural change to that you have to. affect people way beyond your team. Now you have to also work and you have to us to work

multi-party. So like you're building a, let's say, developer platform that they're building apps. Okay, now there's multiple stakeholders. So like the developers building these apps that are going to be consumed by these businesses, these merchants. And these apps also may all be presented to end buyers. There's now three constituents. And there's all these crazy things around like policy, data sharing, just like tension between like which side gets economically rewarded for doing what. Like there's a lot of really interesting things. And so one day I hope to write something about that. And that's even on just like the pure strategy and kind of economic view of it.

But then there's also a super fascinating product design and engineering problems of just like, okay, you have this web app or whatever and you want apps to exist in it. Well, how are they going to exist in it? Right. Okay, you can, are you just going to let them put their link in there and then it opens up a new tab into that other product? That's kind of lame. That's basically like a Facebook comment.

of a link, or are you going to allow the actual, you know, third-party product to exist inside of your product? And how are you going to do that is going to be an eye frame? Well, that's kind of janky. If it's going to be deeper, then now we're talking about like direct data integration. We're talking about maybe your app serving UI on behalf of that app, but then some of the data comes from the third-party server. And like, it gets really, really interesting in terms of user experience and whatnot. And people, it's actually quite common in our life that we don't think about it. So, you know, when you long press on an app on your iPhone and it has a short cut list of things you can do quicker, right? Like, okay, say if you long press your email app,

it'll probably say, like, create new email as one of them. Like, that's an extension. That's iOS saying, hey, Gmail app, I'm going to give you the ability to actually deep link this experience into your app through our operating system, right? Someone actually had to design that idea, that user experience, and we just take it for granted because that's how it works, right? But there's so many crazy decisions there about like, well, if you go too far,

you give Google too much control there and they could do some really messed up stuff. Or if you don't go far enough, then it's really just lame, right? It's not actually powerful. And so this is a really interesting domain. I'm glad you touched on this because this is exactly where I wanted to go next.

Cool. I want to chat about like the PM career track, but maybe before we get into that, I know you haven't written this post, but for someone, that's designing a platform or an ecosystem, is there any kind of just guiding frameworks or rules of thumb that you've come to

to help you make some of these decisions that you talked about? I actually say the first thing is like as a PM, your psychology has to really change around your own validation. So like usually you can build a product, ship it, customers tell you if it's good or not. The cycles for platform work are five to 10 times longer. You're, you know, maybe changing something on the infrastructure level,

then opening up an API and then doing an alpha period for the API where developers now build on that and test things. And then you move into a beta. And then finally, two years later, some end customer actually uses that app for this. And you're not designing actually the end user's experience. You're designing a canvas for developers to build their own creative ideas on. And it's just a very different type of work.

And so, like, you know, I would say, like, that's the first thing psychologically is, like, be prepared for, those are much longer cycles surround yourself with people on your teams that find ways to, you know, enjoy that process and also find ways to celebrate rewards along the way. Like we would, no rewards, but celebrate shipping things along the way. Like when that API went into Alpha, you know, there's no press release. But how do you make the team feel amazing about that work? Right?

You have to tell the big narrative about like, this is going to change, you know, how merchants actually get different apps in these areas. or whatnot, and like, here's some of the crazy things that we were seeing in the early adoption, et cetera. So that's, like, my main thing on psychology. I'd say in terms of preparing yourself, you really have to think about, before you can get into, like, the technical or design execution of any particular platform area, really think about the principles behind the platform that you're building.

So an example and then a contrast with Shopify, it's like, in Amazon's platform, I'm making this up, but I assume that, you know, a pretty big important intro principle is that if there's ever like a toss up between deciding between the seller and a buyer, the consumer, we're going to side with the consumer, right? That's why every time you refund something on Amazon, you get it. Anytime you got a complaint, send you another one, right? Like, they made that trade up to be a consumer-focused platform, and obviously that's been amazing for them. But you also get the contrasting stories of sellers that are really pissed off at Amazon that have like ruined their businesses and whatnot. Okay, so, you know, not to hate on that. But that's just, that's a second order effect of that decision. In Shopify's case,

we are here to support entrepreneurs and businesses in making their dreams come true and creating independence. And that is sometimes at the cost of developers on our platform. And so sometimes we may make like a data policy change saying like, hey, it's more important that the merchant has access to this data, you know, cross apps. And, you know, it's important that actually you push that data back in Shopify so that you don't hold that data back from so that this other app can't use it. And now we're sending the same end customer to marketing texts when they've already opted out of marketing texts or something like that. And so this is where you know, you have to understand those principles and the stack rank of the constituents there to be able to make good policy and design choices. And I think it's something that if you're not conscious of early as a platform PM, you will blow up some stuff or there will be some bad instances that come up.

Or you'll get blocked, you know, by the CEO or whatever on the day before it launches, which has happened to. Oh, no. This sounds like a very hard place to be in an organization, building a platform, building an ecosystem like this. You went into the platform world pretty early when you got to Shopify. And I know a lot of PMs think about should I go platform? should I go, user-facing product. Do you have any advice for folks that are trying to decide which path to take? And is it even like a one-way door? Is it easy to kind of go to a different direction later? That's a really tough question. I think if you have any particular interest in like the types of

problems that you solve, like, you know, I give you a little snapshot of the things you think about as a platform PM. If that stuff gets you really interested, then follow that guy. I don't think it's either or I don't think one is better than the other. I think they're completely different types of a problem domains. I don't think it's also a one-to-way door. I'd say like, you know, even if you do primarily user-facing and consumer-facing side of the product, you're going to be consuming things on some platform somewhere, whether it's an internal API or a third party or whatnot. So you're going to experience platforms good and bad, right? And so you'll learn about it. And then alternatively, on the platform side, you're going to be designing the canvas and you're going to see what gets built

there. And you're going to learn, like, what are good and bad bounds of, you're going to learn, you're not a single user experience, but a universe of user experiences that are possible, like if you create a UI kit or something like that, like you're going to see the good and the bad that comes out of that UI kit being given to the third party of ecosystem, and you'll learn about consumer. And so, you know,

I also think oscillating between them is an amazing experience too because, you know, there are really long cycles in platform work. And sometimes it's nice to like ship and iterate and grow week over week and talk to your users about every single few. feature that you're shipping every other week. And like, that's so fun in different ways. And so I think having both is actually the right goal, both experiences. To zoom out a little bit and

as a final question, if you could suggest just one thing for PMs to do to help them level up in their career and just do better, what would that be? I mean, everyone has so many different backgrounds, but I'd say like overall, based on most PMs that I've met, I'd say, look, it is hard to do when you are PM somewhere, but like do a legitimate side hustle, found a company on the side, and learn everything else. You know, because I think like sometimes you're in this silo of your feature, your area or whatnot, and you forget, you know, what it means to sell something to a customer, what it means to support a product, what it means to like ship something and get destroyed because it doesn't even work or something like that.

And so I think it humbles you a bit. It reminds you of like how hard it is to build software and how many people it takes to do that well. And especially if you're non-technical, you know, like really lean into it and build something simple. Learn how to build something simple for yourself. Demy the technology. You know, that experience will take you far.

Like I love telling people like that literally don't even know, like what HTML is or something like that, which I was one of those people that like, From right now, over the weekend, you could build a clone of Twitter using like a tutorial on Ruby on Rails or something like that. You can do it. You may not know everything that's actually happening, right? But you could actually get that deployed and it'll work and it'll blow your mind that you did that. And I think like once people break through that wall when they're non-technical, I think like the momentum builds from there.

And so, you know, the side hustle and then also break technical walls or obscurity. is what I would recommend. Awesome. I love that advice. It's kind of like a microcosm of create your own little business and do all the things and break out of your little box that you're in maybe as a PM. Where can folks find you online and how can listeners be useful to you? You can find me online, I guess, on Twitter at Brandon M. Chu.

And be useful to me. I mean like, I mean, the simplest answer for me, I guess is like I'm a pretty active angel investor. You know, I've invested in like 60 companies over the last five, six years. So if you're interested in an occasional, helpful angel investors that hit me up, which may be a little bit too busy. But really, like, you know, the honest sense is I don't need anything.

I think, like, you know, if anyone was listening and they want to help me out, just go help some stranger in the world that needs it. I'd rather you do that. I think, like, I've been so lucky in life that I don't want anything. Awesome. Thank you so much, Brandon. Thanks, Lenny. It's been a blast.

That was awesome. Thank you for listening. If you enjoy the chat, don't forget to subscribe to the podcast. You could also learn more at Lenny'spodcast.com. I'll see in the next episode. Thank you.