0:00As tech companies scaled, somewhere along the line, this HR ratio of a pod popped into being. Every time you hire six engineers, you add a designer, you add a PM. Hiring so many PMs infantilizes the engineers and the designers who are perfectly capable of making good decisions but just never had to because there was always a PM to babysit them. Something you wrote online that [music] surprised a lot of people and whatn not product team was built on the somewhat simple premise. We regret that product management exists. Not a thing you probably hear from a lot of
0:28CPOS. We articulate it that way to force ourselves to remember that you don't hire a PM just for the sake of hiring one. You hire one where there's really specific need.
0:35It [music] is better to not assume we need a PM in every place.
0:38The only argument for why you would want product management to be a specialist function is really it's a trade not a qualification. It's something you get good at by doing. It's a muscle. But the flip side of that is the more you abstract your engineers and your designers from doing the same thing, their muscle gets underdeveloped. He also wrote this brutal quote. In the last 2 years, 31,832 people applied to be a product manager at whatnot. We hired one. What does he look for in the folks that you hire?
1:06I can tell you what's definitely trending down. Folks who spend a lot of their time in their interviews talking about driving alignment and stakeholder management because there's definitely a group of PMs whose specialty wasn't technical, it was politics.
1:18You're very excited about this move to IC work. PM's moving away from this big org management world. If you were really successful as a PM, you got promoted into being a director. We took all of our A players and then promoted them out of doing things. Why [music] wouldn't you want Messi playing for your team rather than trying to have the academy coming along all the time?
1:37Today, my guest is Tom Verilli. Tom is chief product officer at Whatnot, former longtime chief product officer at Twitch, and former director of product growth at Twitter. He's also someone I've been wanting to get on this podcast for so long. Tom has a lot of hot takes and really unique and important insights on the future of the product role, [music] what he's seeing the best PMs doing differently these days, and what he's looking for when he's hiring product people for his team. Now, if you're not familiar with whatnot, it's a live stream shopping platform. It's the fastest growing US marketplace business
2:07of all time. At one point, Tom shares how he bought a fresh lobster from a fisherman on the platform. Before we get into it, don't forget to check out lenny'spass.com [music] for a free year of the hottest and most beautifully crafted AI products in the world available exclusively to Lenny's newsletter subscribers. With that, I bring you Tom Verilli. Tom, thank you so much for being here and welcome to the podcast.
2:33Thank you so much, dude. It feels kind of surreal after years of watching.
2:37I hear that. I hear that when people come on the podcast. Here you are. giving you first time long time.
2:42[laughter] That's right. Um I want to start with something that you wrote online that surprised a lot of people and I think will surprise a lot of people uh coming from a longtime chief product officer, longtime product builder, someone that's built a lot of very successful products and teams. What you wrote is since its earliest inception, the whatnot product team has built was built on the somewhat simple premise. We regret that product management exists. Yes sir. Not a thing
3:11you probably hear from a lot of CPOS.
3:12No. Talk about why you feel this way. Talk about how you got to this place. Talk about what this means.
3:19Sure. I mean I always try and start with like history in order to understand kind of things. And one of the things when you come to product management is if you go all the way back like product management didn't exist, right? It was like the business and you know very often founder or CEO types talking directly to engineering and design about what we needed to build and then executing it together. And you know internet businesses it turns out scaled a lot faster than any other businesses in history. And so at some point scale
3:48meant delegating the specifics of execution to somebody or trusting somebody else to work out what comes next because there's just too many things on for somebody to sit with. But if you think about most startups or you think about how that evolution worked, that was rarely a specialist role where somebody was working it out, it was usually you said less things to the engineer where you had to describe in less detail what you were trying to get done to to a designer because they understood or they they'd been involved.
4:15And this idea that we need this kind of specialist decision-making class of humans in tech is really a more modern function uh than it is a like pure necessity. You know, the way I would think about it and the way that whatnot is always treated is like it would actually be way better if engineering and design had the context that they needed to just make great decisions there if they were so in touch with users and what they needed that they could kind of make the same decisions that a product manager is. The only argument as far as I'm aware for why you
4:45would want product management to be a specialist function is really it's a trade, not a qualification. And and what I mean by that is it's something you get good at by doing. It's a muscle for one of a better term. And as every private trainer has ever told me, muscles are built by reps. And so the more you do it, the better you get at it. But the the flip side of that is the more you abstract your engineers and your designers from doing the same thing, their muscle gets underdeveloped. And so I think product management plays a
5:13really important role. And I think, you know, you can deploy product management to have really important leverage on particular things that need to go really well. Um, and in a lot of ways doing that lets design and engineering be the best they can be at their craft in those situations. But wherever possible it's kind of optimal to not have a product manager uh and instead have design and engineering going through those those kind of steps and making sure that their muscles are well repped. Do you feel like product management was very helpful
5:43early on and was important and then it kind of went through a period of wow there's way too many PMs that are not that amazing and now there's kind of this coming back to okay what is actually an amazing PM and maybe we need fewer of them.
5:54Yeah. Uh the funny thing is I think if you talk to most engineers or even designers they will remember the great PMs that they've worked with mostly because they've worked with so many bad ones. Uh, and I don't mean that as a disheartening pjorative for folks, but I think it's more, you know, if you're being kind of really really self-critical as a function. Does the average PM add a ton of value to folks around them in the way that having really high quality product management can, you know, disseminate clarity and
6:23absorb ambiguity in the ways that they can or like help people make really timely decisions. And I think a lot of it is this function of like as tech companies scaled and we ended up hiring so many engineers somewhere along the line um and I don't want to pin it on like HR but somewhere along the line this kind of HR ratio of like a pod popped into being you know every time you hire six engineers you add a designer you add a PM you add an EM and and the you know the nucleus exists and then when you're now serving billion DAU
6:52products you got a lot of engineers and so now all of a sudden you got a lot of product managers and In most cases, you probably don't need a PM for notifications infrastructure, right?
7:04Engineers are perfectly capable of understanding how that works. And in a lot of ways, you know, as we just described, hiring so many PMs infantilizes the engineers and the designers who are perfectly capable of making good decisions, but just never had to because there was always a PM to babysit them.
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8:31Something that I find people run into eventually when they think this way that I want to get your take on is engineers and designers don't necessarily want to be doing the work of a PM because a lot of the work of a PM is kind of annoying and not fun. And you know, there's a glamour part like making decision.
8:44Definitely less glamorous than people think. Yeah.
8:46Yes. Exactly. How do you think about that? just like over especially as a company scales engineers having to be in alignment meetings having to write docs aligning everyone and taking note you know all these like kind of minutiae part of PM and also just the big like they also want to you know engineers want to build engineers want to code designers want to design how do you think about that element of they may not actually want to be doing that work I think this is where like specialization works both ways right it is useful to have folks who are well honed in making decisions it's totally
9:16reasonable as well for someone to say listen uh I'm an infrastructure lead and I want to think a lot about scale and I do not want to have to spend my time debating you know alignment or getting those minutiae right and certain skill sets don't necessarily translate super well right if you're really good at building big mental models in your head of how infrastructure should scale you may not have the skill set of listening to a customer and actually understanding the core problem as opposed to the thing that they said which again just a thing that we've built over time so uh my supposition of we regret isn't to say
9:45that we don't want product managers to do this we recognize in those situations that you do need to kind of help other functions specialize. But I think it's we we articulate it that way to kind of force ourselves to remember that you don't hire a PM just for the sake of hiring one. You hire one where there's really specific need. And I think what goes with it, Lenny, is like you have to build the culture of the organization around that. So for example when we say you know we regret product management exists uh every time we write documents
10:13about how we ship or what we're doing we're very kind of clear that anyone can bring you know change forward that we can have DRI of new product development that is an engineer or is a designer but that everybody goes through that same level of function of like you've got to go through product review you've got to actually do the work because it is real work and if people don't want to do that if they kind of want to do something else we can always move product management And so rather than mapping PMs to teams where you kind of assume that the PM
10:42will always do that, we tend to map them to kind of problems or kind of like core projects and that means that there will be a year more where there isn't a PM attached to a particular engineering team even though there's lots of ongoing product work to do. What I love about this is we often hear uh people at likeoriented products talk like this uh like developer tools where we don't need PMS.
11:03Why do we need PMs? uh and it's often comes from companies like linear and anthra like companies that are building developer tools where you could see why engineers are enough and so it's really interesting to hear from your perspective because you've built very consumerry products very very consumerry products that require what you think are very strong PM skills so it means a lot even more so coming from you that you find that PMs aren't as necessary as people may think in building something great yeah I think there was like two parts
11:32that that drove it um and I've certainly Like a lot of what I'm kind of talking about here are things that I've definitely learned over time. You know, I I spent seven years at Twitch prior to time at whatnot. And that was very Amazon to pizza team, you know, ratio driven. I I started in the valley at Twitter and that was simile very like you always had this kind of very tight alignment and there was god there was a lot of alignment meetings. So you can imagine why engineers didn't want to be in them. And it's kind of evolved over time to understand that like actually a lot of that is just a function of like
12:01management not being able to see what's going on. And so you you hire more folks and you build more layers and your systems beget systems. And and I think what's really changing is people are realizing that like it's not true anymore that the only way to get leverage is just to hire more PMs underneath you and and be more senior.
12:19That you know we've got a better understanding of what's happening in businesses now. It's easier to kind of like converse directly with the codebase and talk to engineers than it ever has been. And so you don't actually have to get into this like all scale thing. And I don't really think consumer or enterprise is the cutting point anymore. I think it's more kind of the culture of the organization itself.
12:38How much of this shift in your mind is AI driven because AI now enables nonPMs to do PME work and how much of it was like pre prei and then I want to talk about just what this actually looks like in your team. But let me ask that question first.
12:51I don't think it's explicitly because of AI but I do think AI makes it a lot easier. I think it's two things. I think uh AI certainly means that there's an enormous amount of leverage for an IC.
13:02Now, I don't know how much other people feel this, but I was talking to a couple of our senior leads the other day and we feel that we're so capable of doing things now with AI that you almost feel a bunch of pressure of the stuff you're not doing because you know that if you carved out a couple more hours, you could you could move at a lot of stuff.
13:17Um it's certainly easier to move fast with AI tooling if you've got wellhoned judgment. you know, you can pull data now on a hex thread that is basically what it would take a week, two weeks with an Amazon L7, you know, data scientist in 2017. And so, if you're empowered and have good judgment, you can basically make really quick decisions and just kind of keep people moving, which is extraordinary. But more than just AI, I think it's also a lot of those kind of like ratio, you know, like
13:46kind of pushes also came with a bunch of other cultural pushes like, you know, hire great people and get out of their way. bottoms up road maps and and all of those pieces where I think there's been a bit of a cultural shift in tech over the last little while which is like actually top down's pretty good because folks at the top generally speaking can make quick decisions and remove all of this alignment debate. They have probably more macro context than most folks and assuming that they are genuinely in touch with ground truth and are good enough. It's actually a really
14:15efficient model to be able to kind of have senior leadership involved in a lot of those decisions, which means you it's not just the tooling that makes them efficient, but you can have one very senior PM across more things and they can be more efficient than having, you know, three relatively entry-level PMs, but certainly AI makes all of that a lot easier. yet. So just to kind of coming back to the broad premise which I think is very important to clarify uh this point about uh regretting product management exists isn't saying we don't
14:43want or think PMs are useful. It's that uh it is better to not assume we need a PM in every place and uh it is great to enable other functions to do the PM work. Uh, and also just PMs kind of take away the reps from people being able to do the things that PMs do. And if they can do that work, they can actually execute better, build better products.
15:03You I think it's also better for PMs to not be mapped specifically to a team than it is to say, we go where the work is. You will build more and better reps. You're going to work out more muscle groups by like moving around on the things you work on as opposed to saying I'm attached to whatever this EM owns.
15:19So, let's let's follow that thread. Uh, what does your what does the team look like? What does the PM/enge design team look like at whatnot? What what does this org look like in this world view?
15:28Yeah, we've um we've just passed 20 PMs.
15:30We have uh kind of I think 21 22 PMs uh in the building today, which um for those following what trajectory is is pretty small considering uh the volume of of GMV that our sellers move. We're very loosely organized into three groups kind of buyer, seller, and what we would call kind of trust and risk. So the folks looking after our standards, you know, payments, kind of safety, etc. And then within those kind of like broad groups, we basically reassign the PMs
16:00pretty regularly. So people have like loose, you know, alignment. Um, you might be like broadly a growth PM or broadly kind of like work on discovery.
16:08Um, but even amongst those groups, it kind of gets allocated and moved around pretty quickly. And that's because the way that we do planning is like every 6 months, you know, the CEO, myself, some other folks and senior leads will sit down and just define what what needs to be true over the next six months. What do we have to get done as a company? Um both in terms of like outcomes and critical projects and then we sit down and we go through that list and say who's who's the DRI, who's accountable for that. And that's mostly how we end up allocating PM work. And so quite
16:36regularly you'll have something you know we've just finished a planning cycle literally this morning and you'll quite regularly go through those and you'll get to the end and say cool there's this thing that's like second or third priority in a bunch of different teams road maps that feels really important who owns that we actually don't have an owner for that and we'll go and grab PM and be like congratulations this is the thing we need you to deliver over the next six months it's rarely you need to build a feature that works exactly this way that does this thing it's a little
17:04more high level than that But like how do you go and work out what needs to be true and then you map the human beings that you think can kind of guide that?
17:12Not every name is a PM name, but overwhelmingly when you go through that planning process, it tends to be PMs and it tends to be kind of PMs who have the right skill set visa be what it is. Whether it's more financial, whether it's more kind of like, you know, algorithmic and recommendations based, whether or not it's like core user feature.
17:28Let me follow that actual specific thread at the end there around what you look for in product managers that you hire. So he also wrote this uh brutal quote in the last two years 31,832 people applied to be a product manager at whatnot. We hired one.
17:48Pretty great. Um so there's a few things here I want to talk about. One is just what is you look for in the folks that you hire especially these days. What do you find? What's kind of like trending up in what you find you need in really successful PMs and whatnot and what's maybe trending down? I can tell you what's definitely trending down. It's uh folks who spend a lot of their time in their interviews talking about those like alignment meetings and driving alignment and stakeholder management and and those pieces because uh there's definitely a group of PMs and I
18:17certainly used to be one of them earlier in my career whose specialty wasn't technical or customer oriented. It was politics. And so folks who tend to kind of like naturally lean towards like driving alignment, building building relationships, I you know, tell me about a time when you failed like, oh, I didn't keep the CEO up to date with something and that led to a pivot is definitely kind of a thing that is a bit of an antiattern that trends down. What we tend to find kind of really jumps in a PM kind of interview is over the
18:46course of of your interviews or your case study, can we see both the macro thinking and the micro thinking? I think the system works something like this.
18:53And I can describe an end state, but can I, you know, almost exude impatience on like and here's how I would validate that very quickly. Here's where I would push to get that done. And are you specific about the things that you've built, right? There's an awful lot of folks who've worked at, you know, Fang, Rubber, or pick any scale company where they babysat things that existed and they've maybe, you know, polished the edges of it as opposed to the idea of saying we were given this problem and I had to go and come up with something
19:22unique and novel or I had to kind of really iterate our way through a complicated change. But I made decisions along the way and we moved because I think it's it's easy in a very large organization with inertia to kind of go along with what's happening and not necessarily be an agent of change or be a decision maker which is ultimately what you need PM to do.
19:41There's something you said there that I just had Elizabeth Stone on the podcast.
19:44she's CPT out at Netflix and asked her what's the trait she most that is also most trending up and she said exactly what you said um initially which was the systems thinking thinking big picture thinking about the bigger uh business and her and her advice there to work on this and I want to ask you if you have any other advice here say someone hears this you're like oh wow I got to work on my systems thinking skills uh her advice is uh take one click back from your problem and think about okay for my manager how do they think about this problem and how does that impact the rest of the business um thoughts on is
20:14how somebody might develop the skill and get better at systems thinking.
20:17I mean I think the skill is exactly the right way to say it. I think you can get good at it from just a mental exercise.
20:21So like you can do it in small ways. One of the things I ask a lot in product review when someone says hey we want to run an experiment is okay what do we do if it's green? What do we do if it's red? And if folks are like actually I don't know how my strategy would change like cool we haven't really thought about that. So like stop and go and do the mental exercise of how it would work. And then I think it's the same thing of you can build quick local solutions if you have done the mental exercise in your head of say well what would happen if we had a thousand times more usage of this than we expected or
20:50what are the unexpected knock on effects that this could have and how do you just start doing all of that in your head before you get pen on paper before you get code on the system and I think it it helps actually unblock people to move faster too because I think the other thing that PMs are often slowed down by is like oh risk Oh, legal might, finance might, another team might. And I think one of the monikers we use internally is know then go as in just like think through all the
21:19things that could go wrong. Understand where scale will break. Understand the things that might happen and then make the like move on anyway because if you've thought through all the things that could happen at scale, you're probably going to preempt a bunch of them. So, uh, I really like Elizabeth's quote there, but mine is like just do the mental exercise of just like playing out if it gets really widely adopted. If it happens, if there is something that goes wrong, what will it be? You don't have to solve all of them. You've just got to think through all of them and then you end up solving more than you think.
21:47I love that. So, it's essentially don't just focus on uh will this be an impactful experiment and think about what comes next and what comes next. If this is true, like okay, it's I moved it. um particularly in a higher growth environment, you're not really looking for a 5% stat win, you're looking for something that kind of like totally moves the business um and that has kind of compounding effect over time. And so you just got to think through what that what that is. Something else you said that uh is changing in how PMs operate that you're very excited about is this
22:16move to IC work. PM's moving away from this kind of big org management world to actually doing the work. Talk about that and what that means for the role of product management. And I I mentioned a little bit earlier, but there was this thing in the, you know, in the ratio land where like what you did if you were really successful as a PM is you got promoted into being a director and then all of a sudden it was like don't be hands-on anymore. Your go go goal is just to coach and guide. And so we took all of our A players and then promoted
22:44them out of doing things. Uh and they spent all of their time in alignment and they spent all of their time kind of like coaching and tweaking what their team was doing. and you get this really yo-yo development process where somebody does all this work, it goes through review, it gets told no, and you're just kind of going back and forward in in reviews. You can see my scar tissue coming through. Um, uh, on our team, uh, everybody is like there are managers, there's like I think four or five people across the team who manage other PMs.
23:11All of them would spend 90 plus% of their time doing IC work. I'm still probably 50% of my time doing IC work personally. And I think there's kind of a couple real advantages of it. The first um is if you are a kind of ZP product where you've got a decade plus maybe 15 years of experience building things hopefully your instincts as to what's going to work are not fairly well honed at this point you can just make decisions more quickly than people you can have real impact very very quickly
23:40and it's really great for the organization to have somebody who can do that as opposed to the idea of like working through three layers of you know we we divide the problem up against amongst a couple PMs those folks need to get into alignment. There's different engineering teams debating stuff, you just tend to go. So that's wonderful. I think the second thing is there's two ways that that ends up driving leverage.
24:02One is a VP in theory can you know handle the workload of multiple kind of like more junior PMs just because as I said they're more efficient and that means that you see more of the board at any given point in time and so you're far more likely to make the intuitively correct decision for how should we tune the discovery algorithm visav people who ship slowly which is you know an evergreen thing in in ecom. Well, if you're thinking about how we, you know, manage uh sellers who ship slowly and you know about the power of kind of like
24:32discovery, you can in either case make the kind of correct decision. You know, one of the things that I remember plaguing Twitch for a long time and I was probably one of the people more at fault of it than ever was the discovery team and the ads team were always at war for impressions, right? Like where do ads go in the feed? What's the impact to discovery metrics? what's the impact to kind of ad dollars? One of the first things I did when I got to Twitch was just put ads in discovery and make sure that it's the same PM who's accountable for both because they're going to make
25:00the natural trade-off that say the goal is GMV generated from the feed. One of them is through organic, one of them is through kind of like a paid substitution solve. And when you put the same person across multiple things, they tend to organically align those things and you just cut out months and months and months of back and forth and the politics that tends to kind of take it from being company first to career first. And so having uh VPs mostly in IC land, having directors mostly doing IC
25:29work, even having me having to grapple with IC work keeps everybody connected to the ground floor of what's actually true as opposed to what seems true in a review, but also means that you're more likely to make the kind of intuitively correct decision early just because why wouldn't you want, you know, Messi playing for your your team when you rather than trying to kind of have the the academy coming along all the time. I love this. So when you talk about IC work for PM, what does IC work for PM in this context mean? Does it mean shipping
25:58code, building or is it like running a team, writing owning a road map, writing the strategy dock? Imagine it's the second bucket. Uh whatever is required to kind of like most effectively ship is the short answer. Um have I personally shipped some production code at whatnot?
26:13Uh do I think that's really the best use of my time? Not really. You know, I'm I'm certain that quietly somebody reworked most of my code in order to be sure that the linting was correct and the localization worked and all of the nuance that decades of software engineering has taught you that you know me and Claude code did not get right.
26:30But I do think it starts with like are you literally in the support tickets? Do you know what customer problems we're having? Have you pulled all of the data yourself so that you actually understand it? Have you sat with engineering and design? You know, have you queried the codebase directly in order to understand how things work? and then have you written the spec are you then running your stand up and we go I think all of that is just like core individual IC work there's a lot of people that have worked their way up the ladder a product become a VP and it doesn't feel exciting
26:58to go back to being an IC some people like clearly you love it you enjoy it a lot of people are like I thought I was done with this I could just work through people I could think big picture how do you feel about that what do you what would you say to folks in the in that bucket uh I think there are probably still a load of organizations where that is really valuable and that they will go. My recruiting tends to be the folks who are, "Oh my god, I used to love product management and I'm so sick of sitting in alignment meetings and and I'm out there pitching CPOS and VPs of product to be like,
27:26don't you miss actually doing things? Do you want to come back?" And I think it's okay for us to acknowledge that there will be a bifurcation across the industry. I do think that there are organizations that are sufficiently large that maybe everyone being hands-on isn't right. I also think you know I mentioned earlier that like you have to have a matching culture to kind of go with this kind of environment where that's the expectation you know where people are like I don't want to talk about it I want to just you know let's go and do that thing and in a lot of
27:55ways you know every every startup is a reflection of their founders and so that naturally tends to be you know how do they think and how do they want to run the organization but I've actually found that for in a lot of the cases you go and talk to somebody who's spent the last five six years as a as a senior director at, you know, Meta who spends their entire time in alignment meetings and they miss actually talking to customers and talking to engineers and shipping things.
28:18What makes me think about it, I imagine you've seen this list of all of these chief technology officers that have gone to become just engineers at Anthropic. I pulled up this list as you were talking.
28:28The CTO of Workday is just a member of technical staff at Anthropic. CO CTO of Instagram, Box is CTO, uh, Super.com CTO. They're just like engineers now at Anthropic. Yep. uh if this my greatest desire that the whatnot product bench basically looks like that um all of these people with like great skills and great understanding and actually end up coming and building as IC's.
28:52What about the like the the comp of this path you know that's people's dream move up to VP make millions of dollars is there a world where you can still do that and be an IC? I actually think it's easier uh spicy take, but like you go and take the uh comp required to have five L5s reporting to one L7 and then four L7s reporting to one VP and now total the comp of that product or and turn around and say, what if I had three
29:19people? Why can't I pay them all, you know, D2 VP money, particularly if they're having the level of impact uh that those folks are having there? Like why not? And just to fully understand why this is happening, why this should happen, what I'm hearing, there's kind of many combinations. One is AI is enabling this, which is great. Perfect timing.
29:38Uh what are the other motivations to do this? Is it just the product ends up being better? Is it fewer people? Uh I certainly think the product ends up being better. Like one of the things that folks have been telling us for a long time is, yeah, that won't scale.
29:52Like, oh, leadership isn't going to be able to stay hands-on with what's going on. you're going to need to go and hire tons more layers. And what we found is that's actually not true, right? It requires a different muscle. You have to make an effort to make sure you genuinely understand, you know, like ground truth. An example we use all the time is we'll be talking in a growth meeting and someone will say, "Oh, yeah, but that was fraud." You know, turn around and be like, "How do you know that was fraud?" Oh, it's labeled in the data set as fraud. Okay. Do you know how it gets labeled? I assume someone in ops
30:22does it. Okay. Do you know the SOP or how they label that? No. Okay. Okay, so you don't know it's fraud. Uh, and if you push, you know, a really experienced product director like that, they're going to go, "Good point. I don't. I'm going to go find out." And then you invariably end up strengthening the system that agents are using to kind of, you know, data label because suddenly there's a very smart person who's very invested in like understanding how we do that and helping guide it. And so just that attitude that says like we're going
30:50to do fewer things. We're going to make sure we execute the hell out of them and we're going to kind of push our best people to be in the weeds everywhere means that you fix lots of things as you go and you don't end up kind of just making loads of trade-offs. And I think there's a general belief that like it's too easy otherwise for growth to hide all sins. Like you get bigger and you just end up scaling and everybody's kind of like working off of averages. So culturally I think you got to be really committed to like let's you know whole ass few things as I tend to say
31:18sometimes. Shout out Ron Swanson.
31:22uh and then push your best people to be really in the weeds of stuff. And actually what you find over time is you end up being more efficient by doing that because you actually understand how things work the first time and you make the best decisions. And then listen AI huge leverage for all of this. I I can't think of how much time I spent as a junior PM asking my engineers how hard something would be and you know distracting actual velocity in order to help scope future stuff. So now I can sit and you know talk to Claude and
31:49understand roughly LOE's. Um I can sit there and go through and be like it feels like there's some car crash of modals that must be hitting new users as they open up the app. And you can literally just go through and be like let's let's load up the feed and talk to me about the logic of who sees what in what order and when does this thing fire and you can get answers really quickly.
32:07And having as I said before folks with enough tenure and enough reps that they can see that and say you know what that's bad. Let's just make a good decision and change the ordering of those. I've saved now a kickoff meeting, an alignment meeting, a week writing PRDS, experiment time, all of that by just having somebody who's kind of empowered to go and make a decision. So, coming back to people that are trying to get a job as a PM, uh whether you're new, let's actually hold off on new people, but people that are say
32:35managers, senior folks that are just like, "Wow, the market has really shifted." The a big thing we're hearing right now is you need to be comfortable with moving back into IC, giving up your fancy title. Is there anything more along those lines of just people looking for a job, struggling to find a job? Any other advice for them? Start doing IC work in the role you're in would be my push. Like get back to the basics of like make sure that you're taking on kind of practical work because I just think it's like good to make sure that
33:04you're keeping those muscles, you know, well honed. I think it also starts with like pushing internally for those things. Like I I would bet that if you started bringing that level of productivity back into the role that you're in, probably helps you where you are in addition to kind of help you where you might move to. But I think there's a lot of chatter online obviously about like PMs or engineers now. And I think that's all well and good like it's a great muscle to go and go and hone. As I said, I've I've pushed some production code because I wanted to go through the exercise of understanding
33:32it. But I think there's also before you get to like building things, it's like how quickly can you get back into the muscle of scoping the correct thing, understanding the problem, being able to define what good looks like, and like take advantage of the scale and the scope that you've got that you can see more and bring more to things. Like I think most folks who've sat in a, you know, a director plus role will know the pain of sitting there and watching a junior PM yo-yo back and forth on the same PRD back to review where you kind
34:00of know what the answer is.
34:03Somewhere along the way, we decided that, you know, lead a horse to water as opposed to kind of help them understand the answer and then keep moving. And I think there's like something in our coaching styles that we can get back to of like help somebody understand what good looks like relatively quickly as opposed to just endless review yo-yo. Uh this point you make about PMs not uh shipping to production, I so agree with this. My mind changed on this recently with a previous podcast guest um with this point that PMS already like the leverage PMs have so much more leverage
34:32if they're not sitting there trying to ship to production. They can enabling the team to ship better and faster and making sure the things that are shipping are better is a much better use of PM's time than sitting there shipping stuff.
34:41I mean this sounds really silly mate but like it takes me substantially longer to go through the minutiae of like getting g get commit and all of the kind of like pieces that are second nature to engineer aligned than it does to actually work out what the problem is and be able to describe it. So yes like good practice to try and you know make sure you're doing something uh for example I don't want to judge if our dev tools have gotten easier or not based on what someone tells me. I'm going to go and try it and be like yep that was easier than last time I did it. But I do think you can get an awful long way
35:10understanding the codebase and then talking to somebody who can actually execute well. You know, otherwise you're just going to get you're going to fall foul of like a thousand classic traps that every other engineer learned how not to do when they were in L4. So following that thread a little bit, what are some of the ways that AI has enabled you and or your team to move faster and be more productive? uh other than prototyping which is the very uh clear benefit of AI for PMs and product teams what else what are maybe in the top three of like wow this has really
35:39unlocked our productivity and and and the quality of what we do I mean the first one I think by a country mile is data science you know we use hex threads internally or whatnot I'm sure there are other kind of like comparable products but I think it's almost hard to remember time as a PM before you had tooling like that where you could genuinely start pulling very nuanced cohort reports of data where you could kind of grab an individual user where you've heard a report actually understand you know like let's pull logs help me understand
36:08exactly what this user did and saw how many other users look like this you know what would impact be and then all of a sudden you can build pretty meaningful sensitivity models or like forecasts of what might happen regression models etc really really really quickly which is like incredibly powerful um the other thing that we found is it helps us move much more quickly with shipping things because you can spot regressions and weird knock- on effects of two products intermixing more quickly than you used to be able to. And I think in, you know,
36:37really large complicated systems, that's always one of the things that ends up slowing you down of like release trains and all of that versus like if you build the right AI tooling, you can spot regressions really quickly, which basically lets people just kind of like go. So, I don't know what the future of data science looks like, but I think uh as a product manager, I've spent less time in the last year talking to a data scientist than I ever have in my career, even though I've probably spent 10 times more time in data and understanding actually how the product's working than I have ever have in my career. So, that
37:06one I think is really powerful. Second one I've already mentioned, which is like stop bothering engineers with how does the codebase work and actually just go and talk to Claude and understand it, which is really helpful. You know, I used to say early on in my career that the goal was always to be understand your systems at the boxes and lines level of, you know, which system drives which thing. And now there's no excuse not to understand that or a nuance layer. But the other one, and this might be very specific to whatnot, so I don't know that this will help everyone, but
37:34one of the things that I've been lucky to do in my career is basically worked on live products for a decade now. And so it's always been really cool to be able to ship a product and then watch a customer use it and watch them kind of figure it out. So like uh I think people have just gotten this experience with like listen labs and and you know others in that cohort of watching people use your product. But I've always been able to sit and watch people use a thing for the first time and go through that new user comprehension gap. What's really cool with a bunch of the AI tooling
38:03right now is as they're describing, oh, I'm having a problem, you can literally be watching the codebase live and work out, is that actually a bug that's happening right now, right now, or is that a comprehension gap where it doesn't work as expected and suddenly you've got this video artifact of someone using your product. You can be analyzing the codebase in real time and you can be just talking kind of through AI to the codebase to understand what's actually happening. And it's this it's like you know a feedback loop on steroids because all of a sudden you
38:33know exactly what's going on customer side, code side and observe side as as like a viewer uh in real time which is really cool.
38:40That sounds uh both awesome and very stressful to be building products that are that live in real time. I think about um Netflix where they invest in live now and that's just like all you've done for 10 years and how big of a deal that was for them. I know the scale is different but honestly my second week at whatnot um I remember sitting in a room watching so uh uh whatn not for those not familiar uh kind of commerce largely auction platform that live commerce platform um and there's varieties of different ways to run an auction but one of them is
39:10what's called sudden death which is like when the timer ends it ends right otherwise the classic auction environment somebody bids in the last 5 seconds it adds 10 seconds back on the clock uh and a seller can decide what auction model they want and I was sitting there watching a seller who was these are taking too long. I wish this 7-second timer was actually 3 seconds because I want to move more product. And the I I watched two engineers in the office look at each other and be like, "That's a config. We could totally do that." And so they went and updated it in real time and then jumped in the chat of a show and just said, "Refresh your
39:38app." And then all of a sudden, bang, it was operating that way. And I was like, "Cool. I'm I'm with my people. I'm in like the right place." Because that's the level of like responsiveness that you can get uh in a live environment.
39:49And obviously AI means that that's really easy for lots of people to take on. Not that I would touch production code uh in that kind of way because that's a disastrous idea. Uh but the qualified humans, it's a wonderful one.
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41:09banking services provided through choice financial group and column NA members FDIC. Coming back to this data science point, uh I I I had a I have a friend who's a data scientist and he said it's a rough time for data scientists because of this exact thing and to add a little more color. Uh basically their time used to be asked to do some data analysis, do some work with the data, come back, here's the results, here's I'm confident in this conclusion. Now their time is
41:37basically uh seeing like halfass data science work from non-data scientists and and just like show me is this right and then they're and half the time it's wrong and they're like what the hell is my job now? It sucks. Yeah. Listen uh I have a lot of empathy for that because I've certainly seen it. another plug for why having fewer more senior PMs is helpful because there are folks who've seen more of those reps and understand.
42:01But I also think a lot of the time that uh lack of clarity comes from the other thing which is organizations have historically underinvested in data engineering and data structures and and good data labeling and whether or not you've got your kind of um not just your taxonomies right, but whether or not you really understand whe whether or not your data systems and structures are set up well. And so what we found is a lot of our best data scientists are pushing in that direction of like uh are we actually you know correctly updating uh all of the ways in which our tracking
42:29and attribution works so that it's less easy for people to kind of like misunderstand those. And then yeah uh using an AI tool to find piece of data much like using an AI tool to write code doesn't absolve you of responsibility to make sure that that was good analysis good code. It's just tends to be leveraged for those people who are naturally inclined that way. So thinking about these different functions, data science, user research, design, engineering, PM. Uh what I'm hearing so far is we'll need probably fewer PMs, we'll need fewer data scientists. Are
42:58there any other roles that you think they'll that are kind of trending down in terms of we'll need and are there any roles trending up? Like wow, we're going to need a lot more of this kind of person. Well, funnily enough, like as I say, I haven't spoken to a data science in a while. We've certainly still hired plenty because I do think that kind of uh all that tracking and attribution and measurement really really powerful. Um I also think one of the flip sides of we say we need fewer. It's like fewer of for the same output
43:27doesn't necessarily mean fewer of in macro because if you are using these systems right you can just grow more quickly. You can build more things. You can take on more stuff. So, you know, I would be surprised actually if we ended up with like net fewer I think it's more like net fewer visav customer impact for both. Um certainly I think kind of like trending up over time within these roles are these kind of like and I I don't
43:57remember the exact label that people used to use but this idea of like um tech leads that are kind of like a hybrid EM where you're running a very small team kind of running at things because the same way that we'd say you know the cost of trying something has come down the idea that says you can have kind of core focus which is a thing we're very big on we've also found incubating a lot of smaller teams to kind of go over and sit in the corner and just try and build this thing. Go and you know it's not quite prototyping, but it's like go and take a swing at a thing that we've historically thought
44:26was too hard is getting cheaper and increasingly has very high leverage. So the idea of like engineering manager light for one of a better term uh is a thing that I'm definitely think that we'll see more and more of. It's like not quite the technical member of staff although that must be lovely. Um, but certainly not the kind of like full-blown EM role, I think is one that that definitely will come about more often.
44:49So maybe just to close the loop on this part of the conversation, there's this, you know, trend towards everyone's kind of a builder. PMs are shipping a little bit, being a little more engineer, engineers are taking on more of the PM work. How do you think this just kind of maybe plays out over the next couple years in terms of what product teams look like broadly? Is it still PM, engineers, a designer, data scientist somewhere? Is there how do you kind of envision the the canonical product team over the coming years?
45:16Great question. Uh and I don't know that I know what it looks like everywhere. I think what it'll look like at whatnot is it probably still looks mostly like it has historically which is you know there are reasons that you would have a specialist designer, specialist engineers, specialist product management. I think those kind of very concrete teams will largely be reserved for like very specific projects or like things that we have high confidence or conviction that we need to solve or we're pretty high confidence conviction that we have a path forward on a scene
45:46and we want to make good progress. And I think at the edges around that, there's going to be a lot more free space for people to play on like, hey, I'm reasonably sure I can go and make a meaningful improvement to this thing.
45:57And it doesn't matter if you are a designer, an engineer, a product manager, a data scientist, you can and you should, right? If you're sitting there on a Friday afternoon and you can't focus on the POD you're writing, but you're pretty sure you can go and fix something, go for it. Um, and so I think it probably doesn't morph in the more formal sense, but I do think there's just a lot more free space for people who are wellversed in the customer problems, wellversed in the codebase, and understand some of that macro context will just be empowered to
46:26do more and more things. Two, two and a half years ago, I had this post I put out where I said why PMs are the best positioned role in tech to thrive in an AI world. And I feel like even though the beginning of our conversation was like uh we should live in a world where we regret PM exists, I feel like we agree on this idea that the skills that seem to matter most and are going to be most valuable whether it's a PM doing them or an engineer or designer is very PMY skills I'll share a few examples in this from this post like what what do we
46:56who is really good at this stuff these these things identifying what to build distilling and communicating requirements prioritizing everyone's ideas for the highest ROI opportunities uh giving giving feedback and design to improve impact, developing go to market strategy, understanding business strategy like to me this is what PMs do and it feels like that's becoming more and more important. So I guess the question to you is you agree with this idea that the PM skills seem to be the most valuable now as AI takes on the building.
47:21Definitely agree or also props for bringing the receipts even with a time stamp my friend. Well done. Mhm.
47:27Um I think what I my only build on that would be to say I think those core PM skills aren't necessarily the things that we have rewarded PMS for over the last 5 years versus storytelling alignment strategy. And so I do think you're 100% correct that like can I genuinely understand the customer? Can I genuinely understand the business? Can I genuinely understand the tech? and can I translate the three together for you know optimal efficiency is the point of
47:56leverage when doing things gets cheaper trying things is cheaper etc um so absolutely agree that product skills are probably the most durable my build would just be there's a lot of people who have the title PM who haven't spent a lot of time building those skills in the last 5 years but have gotten really good at communicating frameworks to leadership uh and so I just kind of push us back as a function into like that core work.
48:23Yeah. Marty Kagan calls this product theater. A lot of people just do the things that PM should be doing.
48:28And listen, I'm guilty of this. We we rewarded it for so long.
48:33Uh that like it doesn't surprise me that that product theater is is a core skill set for a lot of folks. I just think that there's not a lot of place to hide in that anymore.
48:41And this comes back to that 32,000 people applied for jobs. I imagine a lot of that is just people who think they're PMs or have the title PM but don't have but are exactly what you described. They just focus a lot on alignment, writing docs, meetings, things like that and not actual building understanding what it takes to build a successful product.
48:58Yeah. The number of people who do really well in a product interview Lenny and then you give them a case study. So everyone who gets hired at whatnot in any role has to do an actual hands-on case study. But the number of people who present incredibly well and then you give them a prompt and some data and ask them to come back with a POV on something and then we make them verbally defend it. How quickly the thinking decays from folks who are good at the theater but not the specifics uh is kind of really telling I think. Okay. So kind of going uh beyond the hiring step, say
49:26you hire somebody, what are some things you've learned about how to get the most out of the people you hire? you mentioned this kind of uh contrarian take that you don't agree with this hire great people get out of their way. So I want to hear more about that and just is there anything else you've learned about just uh elements to building a very successful worldass product team? I mean nuance required in my like hire people and get out of the way is wrong I will say um but couple pieces to build off of
49:54it. I think in general the hire great people and get out of their way became this kind of like macro saying for let them work out what the road map is. Let them work out what the problems are. Just like completely devolve, you know, like what's going on.
50:10And I think the real answer is obviously the better people you hire, the more you can kind of like totally trust that they know what they're doing. But we tend to live in a verify then trust land as opposed to a like totally trust or even trust but verify which is like I'm probably in a better position than any of my kind of directs to understand how all of the different pieces of our system buyer or seller kind of trust fit together. They're almost certainly in a better position than me to understand the nuance of like how any of those
50:40individual features work. You know if somebody quizzed me today on exactly all the waitings in the whatnot discovery model I would definitely be wrong. visav any of the engineers on that team, visav any of the you know the PMs on that team. Good. But like it's actually kind of incumbent on me to learn that and understand that over time because I'm asking them to make decisions and I am proving things that they're doing. And so time spent actually working alongside those teams like in the trenches trying
51:08to solve something really really powerful. One of the things that I saw earliest when I joined whatnot that I've seen kind of Grant who's our founder CEO do is he'll sit in a review and be like I don't think this is right and then he'll pause and say I'm going to clear the rest of my day. Let's sit and figure it out. And he'll actually end up sitting with the team and going through you know again easier with AI data tools. Let's literally pull up the tickets. Let's literally pull up the code. let's like go through the data line by line and understand what's
51:38actually happening so that we can make a decision there. And it means he's very up to date with what's going on. Kind of very culturally sets the tone for the team that like we're just seeking truth.
51:50And it makes it very much a like us versus you. Like reviews got very into like listen for yes for a little while there where all you're trying to do as a PM is just get a green light so that you can go back to your P your engineers and say I have some credibility. I can get, you know, the CPO to approve what we're building as opposed to this idea that says we're just trying to find out the right answer and in theory everyone wants us to come up with the right answer. So, you know, we use planning to to align the company on like what are
52:19the really important things we have to solve. That's mostly a resourcing discussion, right? Like if we pick the right things, stack rank them all, ultimately I'm most accountable for making sure that we have the right resources in the right places to hit things. But like I don't know if those are the right places if all I do is delegate to the team to go figure it out and I'm not actually periodically very deep with them on like exactly how does that work you know how do our like you know referrals work literally what is
52:48the logic that fraud might use in order to invalidate one oh based on address signals how do we calculate address signals is that like a Google normalized thing or is that like you know free text that's put in and if you don't actually push yourself down to sit alongside your IC engineers and your IC designers and your ICPMs. You don't actually know that stuff. So, you can't make good macro decisions without the micro. So, increasingly, I think, you know, I I
53:16push myself to I try and be T-shaped. I can go very very deep when required, but I'm mostly broad across pieces. And I think the idea of just like hiring people and then like not asking any more questions and delegating all of the detail just isn't really the most successful model for getting the most out of an organization.
53:32With a very product-minded founder, CPO classically is a very challenging role for people because you're basically this person between a very opinionated founder and the team building it. Uh what have you found works in creating a you know environment where you are happy in that role? Yeah, I mean kind of funnily that's been most of my career actually. I worked for three founder founders in a row who are all kind of very product minded. Um and whatnot I've got two which is a blessing actually.
54:02In general uh I try not to kind of double up if you know Grant or Logan our our founders are on a thing probably doesn't need me. Like what's the advantage of an extra layer? Um, you know, I think jokingly one of the PMs on the team has referred to it as the two dads problem where you've just got like two people issuing kind of like conflicting instructions or somebody wants to review and then you do all this work to present it to me and then you go back and it gets a different thing. So my first thing is like if Grant or Logan are on it, I check that they're watching
54:32it, they're accountable for it and I step out. So there'll be long periods of time where like fully half my team can be working on something and I couldn't tell you day-to-day where it is because you know it's with Grant, it's with Logan and that's totally fine. I don't have to be across all of the things they're doing. We just need to make sure that there is somebody doing that bar raising. So we spend a much time doing that alignment. I think the second one is like ultimately if you are a product leader in a founder company, you have to understand it's not your company, it's theirs and you just find the right
55:00balance of like you know hey are you open to feedback on this? Have you made up your mind? You know, are you open to a push on this? And you just find that rhythm kind of working with folks. Generally speaking, you know, there there's a reason that founderled companies do so well in our industry.
55:15You know, the insight required and the kind of customer intuition to make the thing in the first place and work tends to be really important. Um, and then I just view my job as, you know, making sure that we've got coverage on the places where our founders are.
55:27Awesome. So a couple things you've learned here for building and this I think in consumer this is especially important is uh counterintuitively to how maybe people think things should work you're finding that the best teams companies products end up coming from top down founder almost you know micromanagement is a is a dirty word to a lot of people but it's basically being in the weeds is uh in spite of how people may feel this actually ends up being leading to better stuff there topown works well if leadership is good
55:57enough to be in the weeds and be specifically correct. I think where it falls apart is where you don't actually know ground truth and then you attempt to manage people from above and that's where I think the term micromanagement comes from. Otherwise, if you're working from the same data and you have it, I don't know a junior engineer or a entry- level designer who isn't stoked to sit there and work alongside the CPO or the CEO and ship something because you're just unblocked. There's no alignment meetings. There's nothing to do. I also find that like you can give way better
56:26feedback if you're literally in the detail. And I think the nuance is just like how do you make sure you can do that in enough places. There's never been a better time to be in to attempt to be in the detail on things because you can literally query it in real time. I think that's such an important nuance here. The story told is so um powerful.
56:44This idea of grant just okay I'm going to clear my day. I'm going to spend time going deep on this stuff. that feels like a very necessary ingredient for someone at the top to be making micro decisions because to your point if they don't have all the details they don't they're not making a decision out of real data and we can do that because you know as I said we we plan what we're doing and then we allocate and then we're dividing and conquering so like he's probably trying to nail three or four most important things at a time and you know he's the CEO he's going to call the ball and say these are the four things I own right now and I'm gonna be
57:13like great I'll be over here then and then within those Like what am I doing with the rest of my day that is more important than nailing the five things I've said will get done this half. Like if it's anything other than maybe hiring, standing meetings, any of that stuff, you can just clear it and set the tone for the team that like until we understand it, we can't do anything else. Say somebody is looking for a CPR role or a first PM role, kind of similar, basically working for a
57:41founder. uh what would be your advice for them to land in a place where they're happy and not just super frustrated by by this kind of middle layer where they just don't actually have any agency. Yeah, I mean I think the first thing you've got to work out is like why do you want it, right?
57:56There's this idea that like the CPO's job you get to decide all of the road maps and all those things and I've got bad news for you that's like not strictly true. But I think it also comes down to like spending some time with that person to work out like how do we jam on a topic? How do they like to get pushed? How do they not? And then you spend a lot of your time calibrating. So like before I joined whatnot, I think Grant and I had like five or six different coffees where we talked about like how do you get, you know, this type of team to move? How do you work on those things? And then I obviously went
58:25through a series of interviews and actually came down to kind of LA where Grant and Logan were based at the time and spent a whole day with them just like in a room going through a couple different problems, talking through different things in the road map, just like really getting into it. And I tried through that to kind of be my most ordinary self as opposed to like interview self if that makes sense because you kind of got to ask yourself, do I really want to spend my whole time like having this discussion and this debate? But like I like being a CPO or
58:54kind of a product lead because in a lot of ways what I'm doing is I'm like helping translate that vision and that intuition into reality. And then you know there is an art to learning how to push somebody without kind of competing with them. And I think a lot of the times I've seen the CPO CEO relationship go badly and ends up with like the CPO is competing with the CEO for vision and they end up at like loggerheads and I think you know that's not your job.
59:17I want to ask more about that this art of pushing back and and you know nudging things in direction. Is there kind of one trick or one tip you might share with folks to get to be good at because a lot of people deal with exacts and they're always trying to you know get them to agree to what they want.
59:32I think the first thing is like don't treat it as a trick. I mean, you're not trying to get an answer and a yes.
59:38You're trying to kind of seek truth is like my first statement. And so, I wouldn't say it's especially common that we start out of alignment, but I do think, you know, part of your role if you're one of the more senior product folks in the room and the the CEO or, you know, if you're a director and and it's the CPO in the room is like pushing the team in a way that you don't really expect or you don't really understand is like start from a place of curiosity.
1:00:01Does that person have more context than you or is there a thing that you're not aware of that is guiding it? So I often try and start with like can you can am I hearing you right that this is your prior?
1:00:12Is there a you know piece of context or something that I don't have that helps inform that prior? Cool. Make sure everybody's on that same baseline. And you know I coach my PMs to do this with me all the time too of like if I'm coming at you from an angle you don't expect pause and make sure that you understand why. And then after that you know I try and do a couple different things. You're obviously just people are people, right? They have good days, they have bad days. Sometimes it can be as simple as like, is your mind made up on this or are you open to input? If the answer is like, no, I'm pretty set that
1:00:40this is the answer, shut up. Like, don't pick a fight for the purposes of picking a fight. If the answer is like, actually, yes, you're welcome to push me, but I'd need to see data. If I don't have any data in the room, if it's just my opinion, then I the terms of the debate are pretty clear. If I have fresh data, bring it. uh if I really believe a thing and I don't have data, question why um or go get it and then go back to them with the data. But if the answer is like if it's nobody's got data, it's
1:01:09just two opinions, the CEO's opinion is going to win. And like that's okay.
1:01:14Check your ego at the door, get to the answer. But if you've got data, bring it. And then sometimes it's like just make sure that you're debating for the right reasons. I think it's, you know, easy in your PM theater that you're describing of like wanting to make sure that you set the framing and the tone and there are genuinely times in our industry where like nomenclature matters and exactly what word is used can be really important, but a lot of the time it doesn't.
1:01:39There's a concept that I heard uh come up a bunch when I talk to people who work with you. Uh the phrase was uh play the accordion. [laughter] Explain. So I mentioned earlier I'm not huge on frameworks but I do think uh there's a mental model which is quite useful that goes to the thing that you and I discussed earlier on like uh think through a problem mental do the mental work even if you're not shipping at all which is like obviously the magic of code is that you can kind of ship things and iterate really quickly and get data
1:02:07as you go and I think one of the the trappings that comes with that is uh you're just iterating forward and throwing spaghetti at a wall and you don't really know what direction you're going in. I think there's a second failure mode which is people sit down and write out these long road maps and strategic vision docs of what we'll do over the next two three years that kind of loses the comparative advantage we have over every other industry which is learning like AB tests mean that you can update your understanding of a problem and therefore change your direction as
1:02:36you go. So uh the point of the analogy of play the accordion if you think about like a piano accordion before you can play a note you got to stretch it all the way out bring the air in. So, like what is it we're trying to get done here? But you don't make music until you press the key and push it all the way back into V1. And then when you go to play the the next kind of like progression, you pull it all the way out again. Okay, given what we just learned, what do we do? And then you go and build the next thing again. And like you've got to get used to this motion that says
1:03:05like this isn't creating value. Like pulling it out doesn't actually do anything. Uh all the value is created here. But until you are going through this motion constantly of saying, "Well, re-evaluate what we understand. How does this change what we're doing?" You're probably not playing the right thing. And I know I'm probably bastardizing.
1:03:22Somewhere in the in the comments, there's going to be a musician who points out to me that this is actually also one of the ways you make music, but I found it just a generally very valuable like memory device for PMs to be like, you've got to constantly be zooming out and pushing back in and zooming out and and pushing back in.
1:03:38Yeah, that is [laughter] such a fun analogy because you know it's like the even though you make music expanding it, it's like inward uh or it's like learning from the Yeah.
1:03:49What do we learn? How do you communicate to everyone? Back to shipping.
1:03:52It's like a different kind of music.
1:03:53Internal music, external uh experiment.
1:03:55Yeah. Because genuinely there are people who are really big on road maps and there are people who are really big on iteration. I think the honest answer is you got to do both. You can't overindex on either. So the lesson here is uh run experiments and but then make sure you think about the implication of the of the result at the bigger picture and then what are we trying to do? Have a plan like I think the system works this way.
1:04:17I I have this belief that if we change the way that discovery algorithms work for XYZ reasons it will have this impact. What's the smallest thing I can do to to prove that? Okay, it worked. Great. No change to plan. V2. Oh that didn't work. V3 is going to have to be different. And you just kind of want to always be going through that motion.
1:04:36People not watching in YouTube. Uh Tom is moving his handsiculating wild.
1:04:42What's like a what's what's like a context where you have said to someone, "Hey, go play the accordion or we're playing the accordion." Like like what are they usually doing wrong?
1:04:50It tends to be that you're shipping something with in a very local sense without necessarily understanding uh impact. So uh an example right now is you know the core of most marketplaces is listings, right? Like if you try and think about Amazon.com without listings, there's basically nothing there. It's a bunch of, you know, it's a left rail or right rail and some videos. Um, in video commerce and live commerce, whatnot, you don't really historically need listings.
1:05:15If I want to sell you a pair of AirPods, I could literally hold them up to screen and show you them and describe them and say they're AirPods. I'm going to start them at a dollar. And as a buyer, you now have all the information you need in order to kind of like make a purchase decision, which is great. And so you may not have to invest in making listings the way that someone else does. And that's probably net good for a seller because it takes like three and a half minutes to make a listing. Uh and it takes zero minutes to describe a thing
1:05:44and hold it up. Uh but you then zoom out and say, "Oh new buyers are going to come to live commerce and expect search to function.
1:05:54If I don't know what you're selling until after you've sold it, there's no possible way that I can put somebody in the right stream for earpods because they didn't we didn't know you have them and I therefore can't direct people to it. And so you go through this exercise of like we don't need to fix it. It works. And then you're like, okay, great. What does that have implications for other things? Okay, then what would we do? Oh, we're going to make everyone make listings. And you're like, zoom back out again. If every seller is now spending three minutes for every listing that they're making, the number of things they can sell per hour is now
1:06:24dramatically dramatically lower, which means it's bad for sellers. Okay, we can't do that again. And so you just you have to keep stretching through the like what are the longerterm implications or what are the knock-on effects of things we're building. That is extremely helpful. What's interesting about whatnot is it's there's like this spectrum of like whatnot and then there's this whole trend of agentic commerce where agents are going to be buying the things for you and just working with each other create a whole new agentic economy and this is like the opposite humans live talking to each
1:06:53other buying from each other. Uh thoughts on that on that trend and and how may how that might impact you guys?
1:07:00Uh, listen, I for one welcome our agentic overlords for things like I don't want to have to think about light bulbs, air filters, any of the programmatic stuff that I need to run my life, right? Um, I'm also pretty great with it for like really high intent things. I need a particular cable for my computer. I'm looking for, you know, outdoor lights for my house. Things where there are really taxing searches. I think about this, you know, got to go to a wedding which means I need black shoes but
1:07:29delivered by Thursday because if they don't get here before Thursday they're a no good for me kind of things like absolutely but most of commerce in America isn't actually high intent like how many years are we into ecom now like 30 years into ecom and e-commerce has never exceeded 20% of retail spend in America right the vast vast vast majority of retail shopping in the United States is still people going in person and buying things uh in the UK somewhere. It's like 7525.
1:07:58And it turns out actually that a lot of shopping is low intent. I I'm going to the mall. I might be because I've got a wedding coming up and I don't have anything to wear and I'm going to wander around and see what people have available because I don't actually know specifically what I want. And actually the value of stores is that that person who runs that shoe store has agency and taste and she curates a selection of shoes. She has, you know, a level of customer service. She has a window
1:08:28display which can show me the types of things she has. And I can wander around the mall and actually work out what it is I want to buy or be educated by it.
1:08:36And as it turns out, it's quite pleasant. Like there's a reason that the mall is a social thing. And so I think you know that Agentic is going to be huge. Retail is a 7.5 trillion dollar industry in the US though. So I don't think it's a like winner takes all thing. What I think live commerce does is it's the first time that we've ever managed to kind of like bring together scale and convenience of the internet and also that same kind of like social cultural experience uh of physical
1:09:05shopping because you know at at Twitch we used to basically assume that if it's less than a thousand people in the stream it's non-economic because you're you're operating on CPMs. So but you can go into a stream on whatnot and see 30 50 people in that stream and you you imagine for a moment that you're running a shoe store at a mall and you had 50 people in your store, you'd never close.
1:09:25Like, you would literally never shut down the store because that's so much more foot traffic than you can ever imagine being in a store because commerce has totally different economics to entertainment and CPMs aren't the thing that you have to worry about. So, I think it's not really in kind of like competition with aic. I think it's a completely different kind of like customer need.
1:09:45Amazing. There's room for everyone. I want to end maybe with a question about Twitter. So, you were a Twitter.
1:09:51Yes, sir. uh a PM at Twitter working on growth. I feel like everybody that worked at Twitter as a PM was just scarred from the experience of Twitter. Everyone said do not do things this way.
1:10:01What's uh what's something that stuck with you from that experience? What did you learn? What did you unlearn?
1:10:05It is funny. I uh I have said to a friend before that asking someone who was at Twitter in like the 2015 16 era is a little bit like a therapist asking somebody to tell them about their childhood. It's like you know the trauma that you're you're bringing up.
1:10:18Yeah. For those who not familiar with that law, I think we had nine heads of product in the two years that I was there. It was that level of kind of chaos. I think my favorite quote was from someone on the partnership team who said it felt like Carasa lived in the events. That was like how often drama was going on about the place. Um I think Lenny I probably took two overwhelming things away from from my time at Twitter and other than like some incredible friends and I will say that the the product diaspora from that era of Twitter is pretty incredible and and
1:10:45everywhere. The first one is like if you truly find product market fit, like if you manage to bottle lightning, doesn't matter how badly you screw up the organization uh of it, like it's huge.
1:10:57And like Twitter genuinely had that level of product market fit that you could emotionally feel how much people loved your product. And it's a really powerful litmus test to learn relatively early in your career. That's what PMF is. Not like, hey, the graphs look okay, right? There's like a level of further that goes in. Um, I think maybe on the flip side of like less positive is like what I definitely learned is like most of the time you hear it's really complex. It it isn't. Leadership is just
1:11:24weak. So, you know, the two years that I was there, everyone knew we were going to have to lift the 140 character limit, right? There was working group after working group. Like the project beyond 140 was like everywhere because we knew for example that like uh people in Japan tweeted six times more often than people uh in western markets and it was largely when we spoke to them because kanji let you say heaps more uh in the same number of characters than uh you know a romance
1:11:53language did. We knew that was the inevitable end state, but there's obviously a bunch of like work that was needed and trade-offs and just no one wanted to make the call. And so there was just like yet another design sprint, yet another cycle. And it was another year and a half after I left. I think it was maybe even almost two years after I left before someone actually did it. And it turns out, you know, nobody died. The soul of a place didn't fall apart. I imagine the same discussion went on for editing tweets, which took another two and a half years. Like sometimes things
1:12:22aren't actually that complicated. It's just weekly to Yeah, it's funny how far it's come now. You can write an entire blog post on Twitter like articles is a big bet.
1:12:32On the product market fit piece. I think even more important there is the network effects of a Twitter which you spent a lot of time thinking about building marketplaces. Like to me watching Elon basically change everything. I forget who tweeted this but just like everything changed the brand, the name, the website, uh number of people working there, everything.
1:12:48Yeah. people, the team, like what what was the thing that that stayed the same?
1:12:52And it was basically the network effects of Twitter.
1:12:55It's the place to be. So, everyone's there. And that's hard to break. And even in spite of how much you tried to mess it all up, uh it's still kicking.
1:13:03That's bottle lightning. Genuinely, you can tell.
1:13:06Yeah. Okay. I'm going to take us to a recurring corner of the podcast. Fail corner. Why I like doing this is because people see you see see people like you coming on the podcast had have this illustrious career everything's going great constantly or just killing it and they don't see the things that don't work out and the times that uh you failed and in their life things often go wrong. So uh so the question for you is just what's an example of a time in your career where things failed something you
1:13:35build some career move you made that didn't work out and then what what did you learn from that experience?
1:13:40Honestly, mate, and it's it's very nice of you to say nice things, but I feel like I fail more often than I succeed across the course of my career. Genuinely, uh to the to the blog you referenced right at the start, I published in the in the back of that the actual document we use internally to talk about how we build and it starts with like batting 500 is like the goal.
1:13:58So, like you're hoping to be right as often as you're wrong. So there's probably just too many specific examples of of times I've screwed up in my career. But there probably is a really common thread to it and I think it's probably an easy trap for for any PM to fall into which is like um averages mean nothing to the individual is probably the thing that I've like really scarred by. uh in any sizable population, it's really attractive to go and look at like average utility or average adoption of something and then you find that like
1:14:26you know only 3% of people use something and you're like cool we can probably get rid of that feature. It's not used widely but if you don't go a layer deeper and be like actually for like you know it's only 3% of something but there's a group of people for whom that's 100% of what they do. this is their core use case and for expediency's sake because somebody doesn't want to maintain a feature anymore you're just going to deprecate it and then it turns out you like blow up the use case of that group of humans and then to your last point about network effects the
1:14:55ongoing spiral effect of that can be enormous you know I I think about it a lot in e-commerce of like this is somebody's business right if we're just not reliable we're like deprecating a feature it's kind of like a westfield mold just turning off the power in the leadup to Christmas without thinking about it. And so like there are real downstream impacts to people's businesses that often come from just like a lack of nuance in understanding metrics, particularly averages. Like they they just lie to you all the time.
1:15:22And I think, you know, I've probably screwed up in all of the ways in my career, but most of the time I've made genuinely like I'm disappointed in myself levels of decisions. It's typically that I've relied on averages without thinking about the individual use cases that that are hidden underneath. Makes me think about uh Jeff Bezos has a quote, "When you have data and an anecdote, trust the anecdote?"
1:15:41Yeah, that's exactly right.
1:15:46Well, Tom, we've gone through everything I wanted to talk about. Is there anything else that you wanted to share?
1:15:51Anything you want to leave listeners with before we get to a very exciting lightning round?
1:15:55I think all I'd add, mate, and I've really enjoyed the discussion, so thank you. Is like I don't think there is one way to do product management, and I don't think there is one way that AI will shape the industry. So like we're pretty confident that for what not the product we're building and the culture of the company that we have that you know this model of like fewer PMs who are more senior with like a lot more autonomy is right for us. Uh I don't pretend to you know presume that that will be true for the entire industry but I do think there has never been a better time to go back to
1:16:25the roots of like the actual product work and getting out of that theater and I think that probably is true everywhere. um even if you are still you know there are people who are wonderful people managers and really derive their satisfaction from doing that and growing and coaching and I'm sure there'll be loads of places where that's still valuable. So uh assume that at least half of what I've said is wrong in the same basis that half of the things I've probably ever shipped are not correct.
1:16:47That's why I love these conversations and why I think this work that we do together is important is we are living through the wildest time in our careers. So much is changing. so much is being rethought as you've described and it feels like the only way we can make our way through this successfully is to learn from how other people are approaching it. See what they've learned, see what they've has not worked.
1:17:07Take bits that resonate, ignore the bits that seem bombastic or not applicable.
1:17:12Exactly. Because like no one knows exactly where uh Elizabeth Stone had this great way of putting it. We're in this kind of there's there's a storming phase and the norming phase and we're in this storming phase of holy Like I remember in my PM career as I started writing and stuff everyone was always asking me how has product management changed over the last decade. I'm like it hasn't changed. It's the same basically but it feels like now it actually significantly changed.
1:17:34Although to your point earlier actually the core things and also not all be the same.
1:17:39Yeah. Yeah. So so that's why these are so useful just for people to see here's how a team is operating and what they've learned and here's things to try and it may not work for you but this is how we learn from each other. With that, we have reached a very exciting lightning round. I've got five questions for you.
1:17:55All right, here we go. What are two or three books that you find yourself recommending most to other people?
1:18:01Okay. Uh, not to be cliched, but The Hard Thing About Hard Things, I still think is the best book written about product management. Um, just from a like breadth of things that you have to go through and try and do and screw up a lot. Slightly left field. Um, but the best book anyone's ever recommended to me to read, which I now recommend to others, um, is The Purpose-Driven Church by a pastor called Rick Warren. Uh, Emtt Sheer, the CEO at Twitch, used to basically make sure that people read it.
1:18:27It's this wild examination of why people emotionally invest in something and how to engineer emotional investment into it from a group of people. Uh, it's literally a like how to go and build a church uh, guide book written in the '90s. Uh, definitely worth a read if you're in a community product uh, of any form. Uh, and the last one is if you're looking for kind of like fiction or fantasy, which is where I tend to go in the evening, uh, Babel by RF Qual.
1:18:52I love when books have never been mentioned before get added to the cannon of recommended books.
1:18:57Favorite recent movie or TV show that you've really enjoyed?
1:19:01Uh, Star City on Apple TV. Uh, if you liked For Mankind, it's kind of like the flip of that, but it's the Soviet side. It's like watching the Americans and, uh, For All Mankind mixed together. favorite product that you have recently discovered that you really like. Uh, this is a very deep cut, so I will apologize to most listeners. Um, uh, hopefully you've detected the accent.
1:19:24I'm told constantly that my Australian accent is going, but one of the things that I love is every time I go home, I realize actually a bunch of the government services apps in Australia have become phenomenal. You ever had that kind of concept where you're like, I wish the government has all my data or I wish there was just like one place where I could with one click get my driver's license renewed. I could like transfer titles and do all of the admin that slows you down in life. Services New South Wales actually nailed bizarre to me that I would ever come on a podcast and say actually a government run app in Australia of all places is
1:19:53it? But I was home recently and had to do all of my life admin and it's incredible. Wow. Uh something I heard recently about Australia, while we're in that topic, real quick tangent from lightning round is uh with a solar panel buildout that has happened there, there's more uh electricity available in Australia than they can use. Yep.
1:20:11And they're giving people huge in Australia.
1:20:14So it's like uh they're giving people free electricity in the middle of the day because there's so much available and they're like use all your stuff in the middle of the day because this is otherwise it's going to go to waste. There is a pitch somewhere that says if AI actually needs loads of electricity in order to be data centers, Australia's entire 21st century economy should be power.
1:20:30Incredible. That's like such good news that we are finding ways to generate uh so much energy from solar panels.
1:20:37A small piece of regulation 20 years ago that said if you're building a new property, you got to put solar panels on the roof. And it turns out it works great.
1:20:43Oh my god, I love this. I love this optimism of the future because you know the way through, not not the problem.
1:20:51here. Here. Okay, two more questions. Do you have a favorite life motto that you often come back to in work or in life?
1:20:59Uh in my uni days or uh back in college for American translation, uh I used to have a party trick if I'd memorized if by Roger Kipling because I thought it was like deep and really meaningful. Um but I think if if I'm being really honest, uh I'll figure it out is probably the closest. You know, like it turns out most things are not as hard as people think. Like we'll work it out.
1:21:18I'll figure it out. If you're willing to devote the required time, money, effort, energy, you can solve almost anything. Uh, and if you're not, then it's probably not that big of a problem.
1:21:28Final question. I imagine people ask you this a lot, but I'm also just curious. What's something you bought on whatnot in the past month or so? That was just awesome, delightful, surprising.
1:21:38The most fun thing I've bought recently, I'm not joking, is a live lobster. So, um, recently one of the things that's really taken off on whatnot is our like, um, fresh and specialty foods kind of category. And so, there's this wonderful seller who goes by EFish Co.
1:21:54who has a seafood store down on the dock in San Diego. And every morning as the boats come in, he literally goes out and live streams all of the crates of seafood coming in off the boats and then he auctions them off live on whatnot and and ships next day to your door. So, uh, I got a a California spintail lobster shipped direct to my door, courtesy of a live stream.
1:22:13And how does this work? They put an ice ship it next ice kind of like container and it's a UPS overnight on my door the next day. And that is my agent commerce is going to be great, but not all-encompassing because I no intention of buying a spiny California lobster that morning.
1:22:29Unless your agent decides you eating lobster today. And we I got to be honest with you, it was delicious.
1:22:34Amazing. I did not know you could buy stuff like that. Tom, where can folks find you online if they want to follow your writing? Uh, slashhiring, talk about what you're hiring for, and finally, how can listeners be useful to you? If you're looking for me online, I'm TD Robo, TD R O BBO on Twitter, which is or X, I guess, uh, which is where I, uh, do most of my musing. Uh, it's a mix of product management, uh, and yelling about Warriors games. So, apologies in advance. Uh, and then on LinkedIn is the other place I've put most of my kind of like work writing. I
1:23:02will say it's, uh, I I try for quality over volume. So don't expect uh daily daily drops from me on either side.
1:23:09Just bangers. Just bangers once a year.
1:23:11That was the nicest thing anyone said about being ages. Uh just just dropping casual bangers. And how can folks be be helpful honestly? Uh would always welcome feedback around whatnot uh and how people are finding it and what more we can do better. So like hit me up on either of those platforms with you know hot takes uh feedback or thoughts.
1:23:28And then uh you're hiring PMs even in spite of the many strong opinions about product management. Maybe just talk about that and where folks can apply it.
1:23:34Sure. Uh listen, we are constantly looking for PMs. The the intent of kind of like explaining how many people applied versus hired was not to discourage uh people. It was more along the lines of like the proliferation of product management doesn't itself naturally lend to the people with the skill set that you and I have spent the better part of 90 minutes talking about right now. But you know, we hired two people yesterday. I'm very excited for them to come start. Um and we've always got a variety of of PM roles open. the whatnot if you just kind of Google whatnot jobs um the the right kind of
1:24:03application process will will pop up there or I've found that you know the valley is small enough and product management is not that kind of obscure that you can probably find one of the 20 or so humans who work at whatnot and and reach out to them but we're looking at a variety of things right now payments very high on on our list of what we're doing as well as logistics so if anyone is really excited to come work on the future of shipping uh lobsters overnight uh it turns out there's quite a lot of nuance product happen there amazing Tom, thank you so much for being here.
1:24:31It was a pleasure, mate. Thanks for having me.
1:24:33Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennispodcast.com. [music] See you in the next episode.
