Inside Etsy’s product, growth, and marketplace evolution | Tim Holley (VP of Product)

Tim Holley (00:00:00):
When the CDC mandated face masks in early April 2020, that's when essentially we went to sleep one day with our typical April traffic, typical April sales, and then it was Black Friday overnight. And in part, because nobody knew where to find face masks. Our sellers are incredibly astute business people. And if you had been making wedding dresses, and you know how to sew, and you've got material, and you've got a bit of time, making a mask is quite a simple task. And so we just saw this huge surge of demand, and then supply rising to meet it. 
(00:00:37):
And we did something that as far as I know, we've never done in Etsy's past, which is we put out a call to our sellers to say, "Now's the time. Now's the time to make face masks if you can." And so it felt like this is our time to shine, to really help sellers continue to make sales, to help buyers find this critical item that they were looking for. 
(00:00:57):
And then from there, things kept going, and we really worked hard to make sure that the story was not just about face masks for our buyers, that they understood that Etsy's a place for so many different categories and so many different items.
Lenny (00:01:12):
Welcome to Lenny's Podcast, where I interview world-class product leaders and growth experts to learn from their hard win experiences, building and growing today's most successful products. 
(00:01:20):
Today my guest is Tim Holley. Tim is VP of product at Etsy, where he's been for over 10 years, and has helped grow Etsy from around 500 million in GMV to over 13 billion in GMV. This episode is for anyone working on marketplace, or looking for ideas to increase growth, or looking for advice on how to change your internal culture. We get into the big cultural transition that Etsy went through that took them to the next level. Lots of examples of product changes that helped them with conversion, acquisition, and retention. Plus how Etsy organizes their teams, thinks about supply versus demand dynamics, how Etsy got started with growing their initial supply, and also their initial demand. Plus a bunch of frameworks and hiring advice, and so much more. Enjoy this episode with Tim Holley after a short word from our sponsors.
(00:02:07):
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(00:04:24):
Tim, thank you so much for being here. Welcome to the podcast.
Tim Holley (00:04:28):
Thank you for having me on, Lenny, really appreciate it. Looking forward to it.
Lenny (00:04:30):
I'm looking forward to it even more. So you've been at Etsy for I think over 10 years, although I did notice that you left for a year and ended up leading product at SoulCycle. So first of all, what is that about? What happened there?
Tim Holley (00:04:43):
Yeah, at the time, I'd been at Etsy for over six years, and I just had the itch. I wanted to go work on a different product, build different things, experience different industry. Along, had a theory that working on the proactive side of healthcare, meaning fitness and wellness, is how you achieve better outcomes. And it felt like SoulCycle was a really interesting way to do that. Pretty well-known brand, high street presence in many cities. Could you affect change through that? 
(00:05:12):
Ultimately realized it wasn't a place that I wanted to spend a ton of time and energy. And so through a lot of soul-searching, grown, I know I found my way back to Etsy, really anchoring on three things. One, working on a product that you care about that adds value to other people's lives. And so what we do every day at Etsy is we help our sellers make sales, and that's really meaningful for the vast majority of them. It's reaching an audience that they wouldn't be able to reach. And so that feels like a really great thing to get up every morning and work on. 
(00:05:46):
And so that's maybe the business and the product side, and the other side is people. It might sound a little twee, but just working with people who you can learn from and who you respect, and ultimately can have fun working with, it matters a ton. We spend a lot of time of our days and our lives at work, and so doing it with people who you really value, it's awesome. 
(00:06:05):
I have one memory that we used to have an engineer who used to be a standup comedian, and so that really pushed the boundaries of what a standup meant every day. And it was always a little fun, a little exciting. You never quite knew what you were going to get. And so just little things like that, they make the work life really, really great.
Lenny (00:06:25):
That's hilarious. I never thought it that way. I feel like every standup needs a standup comedian in their standup. Sounds like that should be part of agile. We should need to change the manifesto. 
(00:06:35):
So I've always seen the Etsy journey from the outside, and so there's a few things that I've always wanted to dig into. One is I just remember this New York Times story back in the day when your current CEO Josh Silverman joined, and it felt like a huge moment in the history of Etsy, where it feels like it just kind of transitioned from this touchy feely, everyone loves each other moment to just like, "Hey guys, we got to build a real business here that's sustainable." And it feels like many startups have to go through that transition where it's like, "Nothing's ever going to change. It's going to be so we're all family here," to just, "Things have to change. This isn't working." I'm curious what that was like living through that. 
Tim Holley (00:07:15):
Yeah, I mean the first thing I'll say is it was a hard transition, and I was personally fortunate in the sense that the transition you're speaking of in 2017 also happened to coincide with rounds of layoffs. And I was super fortunate that I didn't lose my job, so I don't want to presuppose that my version of hard is the same as another person's version of hard.
(00:07:38):
But I think a lot of us, and myself included, we had a lot of our identity tied up in Etsy and what we're doing, a really deep passion for the mission of the business and what we're trying to achieve. I just mentioned helping small independent sellers. And just to be clear, that hasn't gone away. I think that that's something we've been really successful at pulling through as a line that was true 10 years ago and is still true today. But it was a time when we were really forced to rethink a lot of how we worked and what we worked on. 
(00:08:12):
Just to use a small example, we had had a pretty entrenched consensus-based culture, where we would really debate a lot of decisions and a lot of features. And on the one hand, I think that that does lead to good outcomes, right? Thoughtful products that have a lot of viewpoints really baked into the core of the thinking. 
(00:08:33):
On the other hand, not fast. When you have your identity tied up in the company and what you do, and then you're kind of being asked or you realize that you need to change how you're working, it can feel pretty existential. It's really cutting to the core of who you are and things that you hold really true. 
(00:08:53):
The reality is it's a business, and we needed to get faster at launching features, improving the experience, and ultimately, having a predictable way to drive GMS, gross merchandise sales, which is our north star KPI. And so it definitely took some time to work through that, but we got to a good place, and the results over the last few years to some degree speak for themselves. But it was a testing and trying time for sure.
Lenny (00:09:20):
I'm always curious how these changes play out and what works in making change. Is there something that you remember that Josh did well or that leaders did well to help that transition? 
Tim Holley (00:09:29):
One thing that is just such a standout is having... And I mentioned GMS as our north star KPI, just having that, being absolutely front and center, being the drumbeat that we talk about in every meeting, the measuring stick that we measure the success of launches against. And maybe it's a bit surprising, but we didn't have that type of clarity in the past.
(00:09:51):
And so rallying everyone around that. And you might not pay into it directly. You might pay into it through one or two levels of abstraction, but you're still clearly aligned with what the company's trying to achieve. And that was something that was a really stark difference, and I think that helped.
(00:10:09):
It helped the prioritization discussion a lot. If you can't really articulate why this thing matters to driving GMS and the type of timeframe that we're talking about, be it a quarter or 12 months out, and different projects will contribute in different ways. But that was just one huge standout, and that's been a drumbeat over the years that let's continue to stay focused on that as a metric. 
(00:10:32):
The other thing to me is bringing an outside in perspective, really benchmarking against your competitors and your competitive set. Don't get me wrong, I think Etsy is a unique marketplace. Our sellers are independent sellers. They sell unique items. The reality though is that our buyers are shopping all over the internet. They're shopping on High Street, they're shopping in different places. And so we have to be aware of the broader context of where they're spending their dollars helps us make better decisions over time.
(00:11:04):
And so on the one hand, there is no one-to-one direct competitor to Etsy. But there are other businesses and other brands that are competing for eyeballs or wallets that we need to be aware of. And bringing that into the discussion was a really helpful one that helped ground us in the overall dynamics of what buyers are doing,, where they're spending their money, and how they think about us.
Lenny (00:11:28):
Is there anything else you took away as a leader from watching that shift, that you bring to making change, transitioning people to working in a different way?
Tim Holley (00:11:36):
Definitely focus on a clear KPI that the teams can rally around. That's one. The other is... And I respect Josh immensely on his ability to tell a really clear narrative and use that consistently over time. The old adage of you need to say something three times before people understand it. I would wager you need to say it another three times before they internalize it.
[NEW_PARAGRAPH]And having that be part of the day-to-day conversation, it seems like such a small thing, but it adds up to having clarity on goal, the KPI point, and then clarity on why, the narrative point. If you can marry those two things, I think that's an incredibly powerful combination.
Lenny (00:12:15):
While we're on this topic, I'm curious what Etsy's values are. I imagine you've codified a few, we call them core values at are Airbnbs or something like that at Etsy. And if so, I'm curious what they are.
Tim Holley (00:12:26):
We call them guiding principles at Etsy. We have a few of them, and I won't go through all of them, but just to give you a flavor, one of them is around digging deeper, and that really speaks to aiming to really understand the why behind a change, to really push on the insights that we're learning through qual or quant research, or other inputs that we might be looking at in order to make the best decision possible with the information we have at the time. 
(00:12:52):
Another example of a principle is minimizing waste. It aligns with how we think about product development, which is, we want to know, is the work we're doing adding value to the customer and the business? And so something that isn't working out a lot of times in product development we're wrong. And so being able to say, "No, this is no longer valuable, we need to move on to the next thing," has been something that's served us really well.
(00:13:17):
Ultimately, we are quite a small team. There's just over 2,000 people in the business, and if you then scale back to engineering and product, we're not big. And so we have to be really diligent about how we're investing our time and our resources in order to be successful.
Lenny (00:13:31):
Awesome. Okay, so another big moment as an outsider that it feels like Etsy went through is during Covid. There's this huge transition to e-commerce, and I think Etsy was a big beneficiary of that. People wanting to buy more stuff online, go to stores less. And it feels like it was a huge accelerant for the business. I'm curious just what that experience was like leading the product team through that.
Tim Holley (00:13:51):
It was quite wild, I'll say that. And to be more specific, as many or all of us did in probably the world of tech at least, we went home not knowing what the next weeks or weeks as we thought would bring, turns out years. But when the CDC mandated face masks in, I think it was early April 2020, that's when essentially we went to sleep one day with our typical April traffic, typical April sales, and then it was Black Friday overnight.
(00:14:26):
And in part because nobody knew where to find face masks. Our sellers are incredibly astute business people. And if you had been making wedding dresses, and you know how to sew, and you've got material, and you've got a bit of time, making a mask is quite a simple task. And so we just saw this huge surge of demand, and then supply rising to meet it.
(00:14:47):
And we did something that far as I know we've never done an Etsy's past, which is we put out a call to our sellers to say, "Now's the time. Now's the time to make face masks if you can." And so it felt like this is our time to shine, to really help sellers continue to make sales, to help buyers find this critical item that they were looking for.
(00:15:08):
So it was a very, very exciting couple of weeks while we were kind of adapting to that change. And we were just really... Every day there would be standups. "What's happening? What do we need to change?"
(00:15:20):
I remember distinctly, we were worried about certain sellers not being able to meet the demand that they were seeing. And so we did the old-fashioned thing, of not personally, but we called them and we said, "How are you guys doing? What can we do to help?" And some people said, "We've got this, don't worry. This is squarely in our wheelhouse. We can absolutely meet the supply." And others said, "Actually, we need a little bit of help. We need to take a pause for a moment while we catch up with all these orders, and then we can come back to taking more."
[NEW_PARAGRAPH]And so just getting back to good old-fashioned know your customer, what do they need from you at that moment was just a really kind of powerful thing that took away from that time. 
(00:16:03):
And then from there, things kept going, and we really worked hard to make sure that the story was not just about face masks for our buyers, that they understood that Etsy's a place for so many different categories and so many different items. And that was then the next phase of the challenge. We got a huge influx of new or reactivated buyers. How do we keep them around? How do we make sure that the product does a little bit more work to retain them, and can really have hooks that bring them back time and again? And so that was kind of the journey that we then went on mid-2020, to probably the subsequent 18 months or so.
Lenny (00:16:39):
Is there anything you learned as a leader working in leading teams through that time? It must've been a pretty surreal experience, a lot of stress, people worrying about their own health.
Tim Holley (00:16:46):
I was one of the fortunate ones back then. No kids, worked in an industry that was clearly critical at the time. So I am in awe of how parents worked through that time. So stressful yes, but not to the extent that other people experienced the stress of Covid. 
(00:17:05):
We just tried a lot of stuff. I remember early on, I think we had maybe even daily, but at least three times a week coffee chats with the team, just like, "How are you guys doing? What's going on?" And at a certain point we realized all we're talking about is exactly the same things. Nobody wants to be on more calls and more video video chats. And so we just continued to evolve, and really try to keep a pulse on what the team needs.
(00:17:29):
And that, like I said, given context of being parents or whatever, differed pretty dramatically person to person. So definitely wasn't a one size fits all solution. That's more on the people side.
(00:17:40):
I think on the product side, as I mentioned, we were really starting to get focused on driving retention, or maybe said slightly differently, driving frequency. And that was a newer topic for us. We've long at Etsy been a really, and maybe rose-tinted glasses speaking a little bit, but a really great experiment, A/B testing driven culture. And so when you think about things like retention, you can absolutely test, course I'm not saying you can't, but you're looking at a different time horizon. Instead of someone making a purchase in that visit or in a week, you're looking at do they come back in 30 days, in 60 days, in 90 days?
(00:18:19):
And so that forced us out of our comfort zone to some degree in terms of how we understand, how we measure change, how long we're willing to wait to see it show up. Back to the incrementality point on minimizing waste, is this actually adding value to the business? And so those were great challenges to tackle, of course on a pretty heightened degree of intensity and focus from the business. But that was an exciting time.
Lenny (00:18:46):
Okay. So speaking of that, I want to chat about the marketplace and the marketplace you've built and things you've learned from building. I think it's one of the, I don't know, maybe top 10 marketplace businesses in the world, somewhere in there. And first of all, I'm curious just broadly, what have you learned is really important to just building a really successful thriving marketplace? And then I'll dig into more details. But just broadly, is there anything that comes to mind?
Tim Holley (00:19:09):
This narrative is still there, but I think we really focused heavily on the seller side, so the supply side of the business early on. And we really immersed ourselves in who sellers are, what they need, and how what they need maybe differs from what the solutions that they can find elsewhere.
(00:19:30):
Back in the day, we were doing studio visits with sellers. We were going to their workshops, we were going to their homes. We were seeing how they make items, we were seeing how they package and ship them out. We were bringing them into the office when we were running hack weeks to say, "Hey, we've got this crazy idea. Is this interesting?" So trying to involve them in the product development process to the extent that it was reasonable or feasible. 
(00:19:57):
And so I think that served us really well. We have a very deep and rich understanding of our sellers. And then the next phase and the more recent phase has been, how do we create a world-class buyer experience that ultimately drives sales for our sellers? Because when you have over 100 million items, all of which are unique, you've got a different challenge than when you have 10,000 SKUs that you could kind of find anywhere or on many retailers.
(00:20:22):
And so topics like structured data, topics like how do we help you gain confidence? Buyer this thing will meet your needs from a seller who you may never have heard of. They don't have a brand that you you've ever encountered before. And so we have some kind of somewhat unique challenges on that front where we need to lean into themes that other marketplaces absolutely touch on. 
(00:20:45):
For example, customer reviews play a big role in our experience, but they play a heightened role given the things I mentioned, right? Unique inventory from a seller that is maybe an independent person who is a single entrepreneur, it's one person. 
Lenny (00:21:04):
So you mentioned that initially, the focus was on sellers, which is really interesting because a lot of marketplaces, first of all need to figure out which side do we focus on? Who do we cater to most? And the way you described it is initially it was how do we make sure the sellers that are joining at Etsy are most well-served? And then later on it became more of a focus on the buyer side?
Tim Holley (00:21:22):
Yeah, I guess I'm painting it as a linear approach. It certainly was not. Because if you've got supply without demand, then you don't really have a marketplace. If you've got demand and no supply to meet it, then you also don't have a marketplace. So there's this flip-flop between, do you have enough supply to satiate the demand you have? And playing that out is certainly, I feel like art, not necessarily strictly science.
Lenny (00:21:48):
Yeah. So I'm curious how you all think about that actually. So at Airbnb, there's always this thinking of, who do we prioritize if we have to make a decision? is it host or guest? And it's shifted over the years at Airbnb. How do you all think about that as a, "Here's who we're going to prioritize if we really have to make a decision"?
Tim Holley (00:22:06):
And maybe to your point, that's also evolved at Etsy. And the place we're in at the moment is the job of a marketplace, even pre the technology definition of a marketplace is a seller will go there to make sales. And if they're not making sales, they probably won't go to that marketplace. And so we really see it as paramount that we have a qualified set of buyers who are looking for the items, the type of items our sellers are selling, and that we can help them make a purchase decision, and therefore a seller maker sale. 
(00:22:41):
That doesn't mean that every single team is working on building features for buyers because it doesn't work. Not least because you have a limited piece of real estate marketplace. And if you have too many teams working on it at one time, you'll end up getting in each other's way, and you won't be that productive. And so of course, we have a team that's laser focused on improving the seller experience. How do they list their inventory? How do they manage their sales? How do they fulfill their items? As one example.
(00:23:08):
But really back to the GMS is the north star, GMS represents a buyer buying from a seller. So it doesn't necessarily say build only for one of your audiences or one of your customers, but it says that that's really the job to be done here is helping facilitate that transaction.
Lenny (00:23:24):
That's exactly the same transition Airbnb went through. Initially it was focus on hosts, make sure hosts are the happiest people, and do everything we need to make them happy. And then eventually the business is the customers buying the product, and you have to make sure that they're the happy people. And sometimes you have to push hosts to do things they're not as excited to do for the good of the guest side.
Tim Holley (00:23:47):
And I think it's also the fact that we as the marketplace, and I'm curious if this was true at Airbnb as well, but we have the insight into information, into data, that an individual seller won't. And so we can help them make hopefully better decisions that lead to sales, leveraging the insights that we have. 
(00:24:06):
If you put an item on sale during this time period, chances are it's going to resonate with buyers, and you might get an incremental sale. And so trying to be really data-driven in how we help and guide sellers to take actions that we really believe will be valuable for them and their business, because simply, they're either a small business owner and so they don't have time to do that level of digging. Or it's simply not accessible to them because they have the worldview of their business, and we're looking at the entirety of the marketplace.
Lenny (00:24:37):
Maybe on this thread going a little nerdier, how do you think about supply constraint versus demand constraint? Is that something that comes up? I imagine maybe it's per category.
Tim Holley (00:24:45):
At the high level, we have 100 million items. So if you take that number at face value, you would think we do not have a supply constraint. We want to drive buyers to that supply. When you dig in maybe a more category, subcategory, sub subcategory level, that's where we do start to see pockets where, maybe we want to increase the type and the amount of inventory we have in wall decor. Seeing something behind you, that might not be the right example. But that's where we then start to focus and say, are there areas where we want to lean in?
(00:25:21):
Ultimately, really thinking about, how do we help buyers choose? Because that's when you have 100 million items and even in a sub subcategory or for a specific search query, you still generally have a lot of results to choose from. How do you distinguish one item or one seller from another, based on the needs that you have? When is it going to arrive? How much does it cost? Is it this size or that size? So really trying to lean into those types of things. And again, to some degree that's econ 101. But given the scale we're at, it is a pretty unique challenge.
Lenny (00:25:55):
What are ways you encourage your sellers to offer the things that you think you're lacking?
Tim Holley (00:26:01):
Back to that data-driven point, right? If we can clearly articulate that if you show more photos, you will help buyers understand your item in new ways, in deeper ways, then you're more likely to make a sale. That's maybe a somewhat reductive example, but those are the types of things where we generally know either through the data that we observe based on activity on the marketplace, and/or through the research we're doing, that this will be valuable. The challenge is often, we have so many things that we want our sellers to do. What's the most important thing for them to do right now? 
(00:26:37):
And that maybe changes somewhat seasonally. We're slowly starting to get towards the holiday season. And that just has a heightened purchase. It's a heightened time of purchasing. And contrast that with when it's around Mother's Day, maybe different type of inventory works really well. And so we need different inputs from our sellers. Because ultimately, they're business people. They have limited time in the day, and they want to spend time making. So how can we make sure that the time they spend on Etsy, managing their inventory, offering customer support is as valuable as possible?
Lenny (00:27:09):
So essentially in product messaging and recommendations that you're showing to the sellers is the way you communicate to them?
Tim Holley (00:27:16):
Yeah. And to some degree, we use the buyer experience to kind of signal what matters, right? When we're clearly highlighting photos, then that's obviously a very overly simple example.
Lenny (00:27:29):
Sellers [inaudible 00:27:30] here's what the search experience is highlighting.
Tim Holley (00:27:33):
As an example, yeah. And then really thinking about some of the signals or the snippets of information that we highlight. What goes into that? We know that great customer service a seller, they'll be responding to... We call them convos, but messages on our platform. They'll be responding really quickly. And that's something that we then highlight in the experience, and that if you're meeting that criteria, then we can start to signal to a buyer that, yes, this person offers really excellent customer service, and we can set your expectations accordingly.
Lenny (00:28:06):
Awesome. Yeah, we saw the same thing at Airbnb. One of the things that I worked on, that was one of the bigger shifts in the marketplace was shifting Airbnb to an instant buying experience. And many hosts didn't want that, because they really wanted to vet the guest and make sure they are happy with them. But it ended up being so important to conversion that we just encouraged them to turn it on. 
(00:28:25):
And one of the ways that worked best is exactly what you shared, where in the search experience, when someone came and searched, we just defaulted the search results to only show you instantly bookable listings. And hosts started to realize, "Oh shit, this is where things are going. I think I got to really take this seriously." And that worked really well.
Tim Holley (00:28:42):
Yeah, interesting. 
Lenny (00:28:43):
Pulling that thread a little bit more, I'm curious what you've seen as some of the bigger conversion wins on the buyer's side in terms of experiments you've run that have had some of the bigger impact.
Tim Holley (00:28:53):
I won't say we're consistently, because that suggests that we don't know what we're doing we do. We're often surprised by what works in an outsized way and what we think is going to be a knock it out of the park success, ends up being of minimal value. But coming back to maybe some of the themes alluded to earlier, reviews have long been really important. 
(00:29:13):
And when you're reviewing an item like I said, that's unique, that's from an independent seller, the type of information that another buyer is looking for is maybe a little different than other marketplaces, or even platforms that they might be shopping on.
(00:29:27):
And so really trying to lean into, well, what does it look like in a buyer's hand, in a buyer's home? Maybe that gives the next purchaser a bit more confidence that it's the right size, it's the right color, whatever it might be. And so that's long been a track that has been very fruitful for us, and continues to be something that we iterate on, that we focus on.
Lenny (00:29:47):
Just I understand, that essentially it's recommending to sellers, "Here's the photos you should have on your list."
Tim Holley (00:29:52):
Rather, collecting from buyers. So a seller will give us the photos that they're going to take, and then we can augment those with the, we call them buyer review photos. But ultimately, the experience the purchaser is having either through photo or video is super, super valuable.
Lenny (00:30:12):
Great. Okay, cool. So adding specific photos that you find help buyers convert. Keep going.
Tim Holley (00:30:18):
And then the other side is really leaning into maybe more the behavioral economic tactics of just helping buyers make decisions. Signals and nudges is how you'll see it referred to in literature. And we've seen great success in elevating little snippets of information that really help a buyer understand, "There is actually only one of these. Well, that's good information to know." It's something that then fits into their decision-making process that might've otherwise been buried.
(00:30:48):
And so really leaning into the quick summaries, the easy glanceable information that enables a buyer to gain enough confidence to say, "Yep, out of these 100 million items or the results for this search query, this is the one that I feel best about buying." We've seen lots of success on that track as well. 
Lenny (00:31:10):
That was a track at Airbnb as well. One of the ways they did this is they called it a rare gem, which is something that's available right now, that's very popular, and they created this kind of iconography for it. And engineers on the team ended up for Halloween dressing up as a rare gem. It became a whole thing at the company. And what's funny about Airbnb is every home is a one of a kind. There's only one left always, and there's always jokes about, "We should always be one left, you better book now."
Tim Holley (00:31:36):
I believe it was introduced... I don't believe. I know it was introduced as issue or a bug. But we ended up showing four stars and the fifth star when it was a half star, got rendered as a horse emoji. And so for a second there on Etsy, we had four stars and a horse showing up for some of our review ratings. And that spawned a huge amount of internal fun. And then back to your point around Halloween, we had a few teams being four stars and a horse. It was pretty interesting. 
Lenny (00:32:15):
Was it like five people were four people were a star and there's a horse person?
Tim Holley (00:32:18):
Yeah, exactly.
Lenny (00:32:21):
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(00:33:27):
So going down this track a little bit more, one of the biggest wins for Airbnb's search experience was this very small idea of just, what if you open each listing in the search results in a new tab, and ended up converting 1%, like increasing conversion by 1%? Is there anything like that that you remember that you've done of just like, "Holy moly, that was so simple, but such a big win"?
Tim Holley (00:33:47):
Yeah, we have similar learnings around that exact example. Oftentimes I think about effort and reward. So it might be a smallish GMS win or conversion rate win, but it was a one line text change. And we've seen those where we add a small snippet of, maybe we feel like it's almost marketing copy, and it ends up having an outsized impact. 
(00:34:13):
We had one example where we added some text to the cart experience, and we just saw huge uplift that we really, really didn't expect. It was more us communicating our values as a business, and it was something that really seemed to resonate with our buyers. And so that drove conversion. We've got examples where it's a one line copy change, and it's quite shocking the impact that that can have.
Lenny (00:34:37):
I'm curious what that change actually was, the text change that had that much impact, if you can recall.
Tim Holley (00:34:42):
We've long and continued to invest in sustainability, and the text change was in our cart where we call out Etsy offsets carbon emissions from every delivery. And just adding that simple line of text was something that, like I said, really resonated with our buyers and the type of customer that comes to Etsy, and really drove conversion.
Lenny (00:35:03):
I had Ronny Kohavi on the podcast who's one of the lead experts on experimentation, and he had the stat that 80% of experiments fail at each company on average. Does that sound about right in terms of how you guys find experiments working out? 
Tim Holley (00:35:18):
Yeah.
Lenny (00:35:18):
Awesome. Okay. What is your just general philosophy and experimentation? Does everything run as an experiment? Do things sometimes not run an experiment? How do you think about that at Etsy?
Tim Holley (00:35:28):
Right now, the vast majority of our changes do. And to be perfectly candid, I think that's one of our growth edges as a product org, and maybe even as a company, is bringing in different ways to validate changes. Because to some degree, or maybe the way I think about experimentation, that's the highest bar. That proves with near absolute certainty that there's a causal relationship between the change you made and the KPI that you want to move.
[NEW_PARAGRAPH]But I think that it maybe misses the point in some changes or some areas where you are working towards a bigger net new thing or this specific change won't really be indicative of the greater whole you're building towards.
(00:36:14):
So like I said, I mentioned earlier, we've long been a very A/B testing driven organization, not least because Etsy's background and history has deep, deep roots in an incredible engineering culture. And so that's really tried and true. So the vast majority of things are tested in that way. 
(00:36:33):
We're expanding how we think about looking at cohorts over time. I mentioned retention earlier, that to some degree, it necessitates a different type of test. When we look at our SEO work, you can't think about it in exactly the same ways.
(00:36:46):
But the through line is, is the change that we're making adding value? And that's what we want to try to understand. A/B testing is a great way to do that. There are others, some of which we're starting to employ, others that we we'll continue to investigate and think about how we can leverage.
Lenny (00:37:02):
Is there an example of anything? And if there's not, that's totally cool, of something that you shipped that was maybe negative on an experiment results, or you just didn't want to write as an experiment.
Tim Holley (00:37:12):
When we're collecting inputs from sellers, we just simply don't feel it's appropriate to not either show or honor. We talk about a tried and true practice of sales and discounting. If a seller offers something on sale, then we need to show that. We are really curious about how that actually drives buyer behavior. And there's ways that we can kind of construct pre-post analysis and things like that to try to understand the impact. But ultimately, those are the kind of areas where we err on the side looking at our data in different ways. And so we have maybe a slightly different degree of confidence in the value, but we're still confident that it does help the marketplace as a whole.
Lenny (00:37:55):
That's a great example. Yeah, I'm not sure what I do there. That is tricky. So we've been talking about conversion. I'm curious in terms of acquisition, what you've seen work. And just generally, how do people find Etsy? How do you drive top of funnel for Etsy?
Tim Holley (00:38:06):
Yes. There's two sides to Etsy, right? There's the seller and the buyer. Getting in the Wayback Machine, on the seller side, we would be at craft fairs like Renegade and other places where our sellers were selling in person and really letting them know that Etsy exists. And so that was very boots on the ground, let's get out and try to acquire sellers into the marketplace. Some of that predates me to some degree. We were probably doing it on the tail end when I joined.
(00:38:37):
And then we have a lot of great word of mouth through our sellers. A seller probably knows other people who are similarly inclined to be incredible craftspeople, who want to sell their items. And so we've seen some success with our... We have a Teams platform where sellers can come together, ask each other questions, and the word of mouth type of growth through that.
(00:38:56):
On the buyer side, we really leveraged the fact that we have a ton of inventory. And to some degree, it ends up being quite a long tail of inventory where we can meet really niche and specific needs. And so that lends itself really well to thinking about SEO, lends itself really well to thinking about Google Shopping, where someone is not on Etsy, but is often looking for something either somewhat or very specific. And we can really meet their needs in a really meaningful way by showing them not only just a single item, but maybe that and then other options that they might find that are of a similar vein, in a similar, sub categories in some cases. And so those have been long tried and true areas that we've invested in, and we've seen really great success in driving new buyers to Etsy.
Lenny (00:39:44):
I've researched and written about that story of how Etsy started with sellers and craft fairs. And so that's a really classic story. And I think there's also an element of the early sellers drove the early buyers, because they're just advertising their listing page, "Here's where you could go buying," which is a really unfair rare, opportunity to grow the marketplace by just focusing on sellers.
Tim Holley (00:40:04):
I mean, yes, and a seller is a buyer. And so if they're making something that they've poured their heart into, chances are they will value that exact same behavior in someone else. And so if they're selling an item, they're looking for other things in maybe not their exact category, but in adjacent categories, and they become buyers. So it is a nice dynamic when that starts to work.
Lenny (00:40:29):
Yeah. So many natural advantages to getting this marketplace off the ground. How cool is that? You mentioned word of mouth as a big part of how Etsy started spreading. I imagine even today there's a lot of just, "Hey, you should check out Etsy." Is there anything you've done that accelerates word of mouth or build on word of mouth, referrals comes to mind? Is there anything along those lines?
Tim Holley (00:40:46):
Yeah, we dabbled with referral programs a while ago, probably eight some years ago. What we saw, it was a different time. And so I think we maybe didn't value a new buyer, for example, in the way we do today. Because to some degree, you're unlocking future value. They make a single purchase, and then the bet is over time they'll go on to make subsequent purchases. We didn't necessarily have that as deep an understanding then as we do now. So our buyer referral program ultimately wasn't a huge success.
(00:41:15):
But on the seller side, this was back in the days of Dropbox referral program being a huge, huge driver of their growth, and the whole get concept that was really prevalent back then. And on the seller side, one of the things that we really leaned into was, on Etsy, for those who aren't familiar, it costs 20 cents to list an item.
(00:41:36):
And that may seem like a very small financial outlay to get started, but it's a little bit of a barrier. And the more we can do to remove those, the higher chance that someone will either become a seller or list more items.
(00:41:51):
So we really leaned into that as the currency for the seller referral program. And coming back to what I said around Teams, that was a really great way to supercharge some of that activity that was either happening, but more of it could happen, or really helping a seller understand, "Oh yeah, there is a hook here. If I offer this person, I refer them, they'll get some listing credits. It'll be easier for them to open their shop. And then when I need to list more items, I also have credits that I can apply." So that was one small area. I wouldn't say it was a huge driver of growth. But in certain markets, in certain pockets, we saw it work pretty well.
Lenny (00:42:27):
Awesome. That also helps with fraud, which is a huge problem with referral programs where the credit is just, you can list on Etsy. It's not like you can steal a lot of money away from the business. So that's clever.
Tim Holley (00:42:39):
Yeah.
Lenny (00:42:40):
Okay. I want to talk about one other part of the funnel, retention. Is there anything you've learned that has been really effective to help with the retention?
Tim Holley (00:42:46):
We have long had features that are retentive in their nature. Things like, on Etsy, we call them favorites. That might be liking or a similar action on other places. But how do we think about the habit loop of if you take an action, what's the trigger and then what's the reward? 
[NEW_PARAGRAPH]And so using a favorite as an example, you favorite an item. That's a pretty strong ish... Of course, adding it to your cart or maybe purchasing it, that's the strongest of signals, but you've shown intent. 
(00:43:21):
So what can we do with that information? We can then say, "The seller put it on sale. You should come back and check it out. This is selling out. There's only one of this item left. You showed some intent, you might want to come back and get it." And that's just one example of trying to close those loops.
(00:43:35):
And that's where we've worked on things like, we call it the updates feed, essentially a feed of activity that you've taken, that we're demonstrating how it's changed, what's new, and then pulling in the tried and true tactic of push notifications to make you aware of that, such that you're using your phone all the time. You see that show up. That's a pretty great notification to get right. "The thing that I really liked is now on sale. I want to check that out."
(00:44:00):
And so those are examples where really leaning into that habit loop framework has helped us understand, we've got a lot of this activity. How do we close the loop? How do we make it really valuable for our buyers?
Lenny (00:44:11):
Zooming out a little bit, it's kind of wild that Etsy can exist in a world of eBay and Amazon. And I'm just curious what it is that you think the founders and the team did early on to carve out this space of, I know you could buy things from people, you can buy things on Amazon really quickly, to create a world where Etsy builds this massive business that continues to thrive. What do you think was done so well to carve out the space?
Tim Holley (00:44:36):
I think that to some degree, resolves down to... And maybe that's a little too extreme, but a key component is the brand. The brand stands for something in people's minds. And that helps understand you're not going to get the same inventory on Etsy. You shouldn't expect the same inventory on Etsy as you might be looking for on eBay. It doesn't make sense to our buyers. The items that our sellers sell are unique. 
(00:45:07):
And so I think that as the core nugget, combined with how we think about policies, and our way to some degree, maintain the integrity of the marketplace, those two things combined do set us apart. And I think if you ask many people, certainly here in the US, what they think of Etsy, a very specific image will be conjured up. That may be one that we want to evolve and build on, but it feels quite distinct. 
(00:45:37):
And it's not the same as eBay and it's not the same as Amazon. And I think there's real deep value in that. And I wasn't here at the very beginning, but it's certainly something that was there at the very beginning of Etsy, that is still a through line to where we are today.
Lenny (00:45:53):
That makes absolute sense to me. On the other hand, I also don't know how that happens. Is there anything that you think about, of how the team did that and how they built that brand? What are some of the important elements? Is that a specific aesthetic? Is it a certain type of supply that you stuck to? What do you think was so important to building that brand?
Tim Holley (00:46:12):
I think it is the supply. If you think about the marketplace, the vast majority of content is maybe what we might consider UGC. It's either the item is from the seller. Or as was mentioning before, the buyer review is from the buyer. And so just being really clear about what's okay to sell and what's not okay, I think does really differentiate us. 
(00:46:38):
I also think over the years, our brand, and our aesthetic, and how we position ourselves has evolved, will continue to evolve as it should. But to the point where we are now, the statement we have is keep commerce human. And that feels really simple, super pithy, easy to remember, but has lineage when you go all the way back to where we started in terms of really valuing the unique, valuing the handmade. And so that does permeate decision making, how we show up, the type of features we work on, the things we would prioritize. Maybe never say never, but an item getting dropped off by a drone and a person never touches it, that doesn't feel very Etsy. That's not something that we might lean into.
Lenny (00:47:22):
It's interesting how many parallels Etsy has to Airbnb, because Airbnb is the same general idea. People's homes, people making things. And then also, I think the tagline for Airbnb early on was travel like a human. So it was actually a really similar concept.
Tim Holley (00:47:35):
Yeah.
Lenny (00:47:36):
Which touches on a question I wanted to talk about, which is many marketplaces as they grow, become supply constrained. And then there's this pressure to add different types of supply. In Airbnb's case, it was, "We should add hotels, we should add property management, vacation rental companies on here. We should have everything people want to book, because we're losing business. They could book anything here, they should be able to." But the tension is, then we become like everyone else. And then what is Airbnb in that case? 
(00:48:04):
And I think you went through that experience where there was a lot of cheap products from overseas, and it was kind of being flooded. Is that true, I guess? And then just how do you think about that limit, and where you draw that line?
Tim Holley (00:48:17):
Yeah, I think it does come back to some degree to the brand and the policy point from just before. And we take enforcing our policies really seriously. It's not an easy job at our scale, and that means we need to continue to invest and continue to make sure that only the best items, the most relevant items are on Etsy. That job is never done. The team that that works super, super hard, and is always looking for new signals to understand what maybe doesn't meet our criteria.
(00:48:49):
Generally speaking, supply is something that we have in spades for the most part. Back to the point we talked about earlier, one of the things that we grappled with was around, how can we help sellers scale? They sell great inventory, but maybe they just don't have enough of it, or they can't meet the demand, because they're making everything by hand.
(00:49:10):
So one of the things that there was an evolution, was leaning into what today we call production assistance. And the way I think about that is you still need to understand the provenance of your item. If you are saying, "I have this design, I'm just going to throw it over the fence to a manufacturer that I've never met, that I don't know. I don't understand their processes, I may not agree with them," that doesn't meet our criteria. You need to understand how it's being made, who is making it, have a relationship with the person who's helping you scale your business. But that's something that we saw from people who maybe gravitate more towards being designers than being able to actually make the thing. They have this excellent idea, they just can't see it come to life.
[NEW_PARAGRAPH]And so they need some help. And that was something we leaned into to be able to, like I said, help sellers that maybe weren't able to make a thing and sell it on Etsy. Or for sellers who were reaching the limits of what they could supply, really take it to the next level, and make more items such that they could make more sales.
Lenny (00:50:10):
So it sounds like essentially, this is just evolving definition of what a supplies allowed on Etsy, a team that stays on top of that. Imagine there was just a hard decision at one point of just, "We will limit supply, and here's the supply that we want on the platform. Everything else we're going to take off."
Tim Holley (00:50:25):
We would limit the type of items, the number of those items, that as we talked about, there's a lot of them. But really having that clear definition. In some cases, it's easy. Some things, they violate legal definitions. And those things, that's the easy stuff to think about. It's where it's a little more gray, that it gets a little trickier.
Lenny (00:50:47):
That reminds me, so my wife is actually a designer, and she produces these hilarious charts about life stuff. And people take her designs and just sell them on every platform on Zazzle, and probably Etsy, but everywhere. And she's always trying to hunt them down and get them to take them off. But it's such a pain for a small designer. It's not an Etsy problem, it's just a general internet problem.
Tim Holley (00:51:08):
Yeah. And back to the, we have teams hard at work thinking about IP, and how to police it, how to enforce it. 
Lenny (00:51:16):
It's tough.
Tim Holley (00:51:17):
Not a domain I will suggest I'm an expert in, really, really tricky stuff, but we've got to be beyond that.
Lenny (00:51:23):
Yeah. Another I think problem that's sort of unique to Etsy, something that I think people call the graduation problem. Which is where you join Etsy, things start to grow, you become really successful. And then you're like, "Why am I paying Etsy all these fees? Why don't I just make my own website and just sell it directly, and not pay any fees?" And I think you guys went through that. And so if that's true, is there anything you've learned about just how to avoid getting people to want to leave?
Tim Holley (00:51:48):
I think the core thought there is, our fees are generally low and highly competitive. So from that perspective, there's a reason to stay on Etsy. What we've seen and what we know, our sellers are really smart business people. And so if they can distribute their products through another channel, that might be their own website, another marketplace in person. Probably going to try to do that. They want to make more sales. Not all, but many of them are wired to want to grow their business.
(00:52:21):
And so really understanding the role that we play in that construct of distribution channels to make it a little reductive is really helpful to understand. And to some degree, we want to be the place that not only they make sales on, but they love to sell on, because our tools are really catered to the needs that they have.
(00:52:42):
So there is some degree of stickiness. I mentioned Teams earlier. There are places where sellers go to congregate, share ideas, share grievances in some cases, but ultimately support each other. And so there are reasons to stick around. I'm sure there certainly sellers who scale out of Etsy who realize, "I want to build my own website," to the example you cited. The reality is that's neither cheap nor fast. It's hard work. It's hard work to build, hard work to maintain, expensive to drive traffic to. And so that may be a part of the way they want to take their business, but oftentimes, Etsy still does play a role in how they're thinking, about where they make sales, and ultimately where they're going to see growth from.
Lenny (00:53:24):
The cool thing that I saw online about you, is that you built a marketplace essentially within Etsy called Etsy Studio. And I'm not sure if that's around anymore, but I'm curious what the story there was, and what you learned from that experience, and current status.
Tim Holley (00:53:40):
Yeah, well researched. Because no, it is no longer around. The white space we saw with studio was essentially saying, on the one hand you've got Pinterest fails, right? You've got all these great inspiring items or projects on Pinterest, and then you have people who've no idea how to make them, and they get so frustrated.
(00:54:01):
And then on the other hand, you've got a marketplace like Michael's, or these other places where you might go for craft supplies. They have stuff, but they don't necessarily have inspiration. And how can we play in that intersection of the idea and the items and the tutorials to see that idea come to life?
(00:54:21):
So the genesis of the idea, felt from a brand perspective, super aligned. We stand for creativity, we stand for makers. And so we saw it as a big opportunity. The launch happened to coincide with the pivot in 2017, to really focusing on the core marketplace or refocusing on the core marketplace, maybe I should say. 
(00:54:41):
And so it became clear that when we laid out what we're optimizing for, which is driving sales in the short term, marketing dollars being as ROI positive as possible, having teams focused on the core marketplace, it didn't check any of those boxes. And so really, really tough decision and hard to manage through, but that was ultimately the right call for the business to say, "This no longer makes sense given the new constraints that we're operating in, given the new goals that we have."
Lenny (00:55:10):
Makes sense. Also something that happened to Airbnb a lot, trying new things that they didn't work out, had to move on. 
Tim Holley (00:55:15):
Yep.
Lenny (00:55:16):
That's how it goes. 
Tim Holley (00:55:17):
Yep.
Lenny (00:55:18):
Shifting a little bit to just product leadership and writing the product team, and just a few more questions, what's something that you've found to be really important to having a productive, well run, well executing product team?
Tim Holley (00:55:31):
Yeah. One of the things that's certainly not completely novel but I think we have a pretty unique interpretation of is how we collaborate between functions. You'll often hear the three legs of the stool where you've got product and engine design,, and we've evolved that to five legs of the stool. And I fully recognize that a five legged stool probably is not a very stable thing, but go with the analogy for a second-
Lenny (00:55:56):
I think it's even more stable. Is that the most stable stool or is it less stable with five legs?
Tim Holley (00:56:00):
You probably need a really flat surface. 
Lenny (00:56:02):
That makes sense.
Tim Holley (00:56:03):
Regardless, of course we've got product eng design and we've got our insights partners. So research and analytics, and we've got our marketing partners really working in a tight team to build the best products possible. And so I think that we can continue to get better absolutely, at how we make decisions and how we bring the various viewpoints together. So to some degree it's not the easiest path, but it's the best path I think, where you're really incorporating different viewpoints, different constraints, different considerations into the features and the products that we're building. And treating that as the core leadership team I think is really valuable.
(00:56:45):
And maybe that's partly because generally, we don't subscribe to this idea of PM as the mini CEO. You're up there directing from on high that we're going to build that feature and we're going to do that. And that's just not the type of culture that we have, and generally speaking from what I've seen, doesn't lead to good decisions or the best features or product being built. And so collaboration is something we really value and that we try to live through how we structure our teams, how we make our decisions. Is it perfect? Like I said, absolutely not. I think it's the way that we've found being really successful building product.
Lenny (00:57:21):
Do you give the PM just a little more say in decision making and ask? Because with five people in the leadership team, you talked about how back in the day, it was like too consensus driven maybe, and I wonder how you navigate that with five decision makers.
Tim Holley (00:57:35):
Yeah, we're always looking to clarify, or re-clarify, or restate who ultimately is accountable. And in many cases it is the PM, right? You are the one who Nick, our CPO like to say you don't have to have the best ideas, but you have to choose the best ideas. And so really figuring out how you're selecting what you're going to build and then living with the consequences.
(00:58:00):
Of course ideally, successful. In many cases, back to your 80% stat that 80% of experiments don't work, owning what's next, right? Okay, did we learn from that? If we did, what are we going to do about it? That definitely does fall to the PM. It doesn't give you the permission to ignore other viewpoints or make decisions in a vacuum. It's certainly not that. But ultimately, when we need to move forward, it is the PM that is on the hook for those things.
Lenny (00:58:26):
Awesome. So essentially, the PM can make the call if there's an unclear consensus?
Tim Holley (00:58:33):
And given so many places are, but we're so heavily led by the insights either qual or quant. The decision in many instances is clear. When it's not, that's when we need the product person to step forward and say, "We're going in this direction." Don't know if it's going to work out, but we'll certainly learn and we'll move forward.
Lenny (00:58:50):
Awesome. And then just to go on this topic a little bit more, your teams are cross-functional dedicated teams. I imagine it sounds like there's these five leads for each team. Is that roughly how you organize?
Tim Holley (00:59:01):
Yeah. And the fifth leg, if you will, of marketing, that might be product marketing in some cases, that might be brand marketing in others. And so there's kind of different flavors of marketing that we pull in, based on the specific needs of the project. But that's generally speaking how we try to structure our teams from kind of the group level all the way down to the individual squad. We can't always have a dedicated research, and a dedicated analyst, and a dedicated product marketer to every single team. So it's certainly not perfect, but that's where we aspire to having at least coverage on those roles.
Lenny (00:59:37):
Got it. So most teams have dedicated marketing person or a product marketing person. That's crazy. That's really rare, but interesting.
Tim Holley (00:59:43):
Some teams-
Lenny (00:59:43):
Some teams that I imagine are most in need of marketing support. Got it. Are you able to just paint a rough picture of the way the teams are laid out at Etsy? I imagine there's a buyer side and a seller side. How does that look for people to make sense-
Tim Holley (00:59:57):
Yeah. The way that we think about the structure right now, and the org design should ideally follow strategy. And if your strategy is always evolving, then your org design is always evolving. We call it the product stack. And so we've got our core customer teams, who are unsurprisingly thinking about buyers and sellers. And so they're the ones on the front lines with the customers.
(01:00:26):
Then we have, we call them our partner teams, and so they are working directly with the end customer. So think an organization like payments where they have clearly a way to capture payment from a buyer to remit funds to a seller, so they're really on the front lines with the customer. They also have other constraints working with the payment networks, and card providers, and things like that, so they just have a slightly different model. So core customer, partner teams, enablement teams that are really in service of helping deliver the best possible experience. That might be through our recommender systems or through our design system, in order to make developing that little bit easier, a little bit faster, a little bit more standardized in some cases. And then the foundation of it all sits with infrastructure, and the teams that you might expect that are much more technical in nature, that really, without that, we wouldn't have a website.
Lenny (01:01:20):
When you're hiring a product manager, is there anything that you found to be really important or interesting, or maybe a unique insight into hiring teams?
Tim Holley (01:01:28):
The three things that I come back to time and again, is one, the collaboration piece that we talked about earlier. Not only a willingness, but a real excitement to do that. It's not everyone's bag. I get that. Some people just want to be in a make fast decisions and move forward place. We aim to make fast decisions, but you need to consult. That's one.
(01:01:49):
Two is being decisive. We have tons of data, but it's not always clear exactly what to do with that, or we're using a new input. Maybe back to the point mentioned earlier of looking at competitive insights, let's make a decision, let's move forward. Let's ideally learn. Even if we're not making progress against our goals, we're at a minimum learning. 
(01:02:10):
And then the third point is just curiosity. Because we're a relatively small organization with... Everyone says, "If only we had more people," but we are quite small. 
(01:02:20):
So there is a lot of change. There's a lot of new priorities that crop up, and that means there's a lot of opportunity for the right folks, right? If I want to be in this space, and only this space, and this is my specific domain, and I just want to be in it forever more, that might be a little more challenging, because you might be asked to work on something net new. And so just having that curiosity mindset of saying, or maybe said differently growth mindset of, "Okay, there's something to learn from the thing I'm being asked to do, let me really lean into that."
(01:02:47):
And to some degree, I'm not describing anything that's atypical of great product people overall. But I think we have either a slightly different flavor or we need it in a slightly different way here at Etsy.
Lenny (01:02:59):
Awesome. Last question, before we get to our very exciting lightning round. Is there a framework or a process that you find really useful, that you find yourself coming back to, that you think listeners would potentially find really valuable?
Tim Holley (01:03:11):
I won't pretend to know whether listeners find it valuable. But the thing that I do a lot, that we do as my team, that others do to some degree is a simple exercise of weekly focus. What are you focused on this week? And then reflecting on, did you get done the things you were focused on last week? Seems super simple, but just the exercise of thinking about what matters, writing it down, and having a little bit of social proof or articulating it out to others creates some degree of accountability, is something that is very, very easy and simple to do.
[NEW_PARAGRAPH]And if you do it consistently, you start to see some really great patterns of, "Those types of focus areas take me longer than I think. I should budget more time." Or, "These are the type of things that crop up. At this time of year, I might need to start thinking about making some space for them." So I've just found that to be really, really, really helpful in the day-to-day.
Lenny (01:04:06):
I love that. How do you operationalize that? Is it like a Slack channel people post these in, is it a Docs?
Tim Holley (01:04:11):
Yeah. In our buyer experience product channel, on Mondays, everyone's kind of sharing what they're focused on. How last week panned out, was it done? Is it still in progress? Things like that. It's very, very lo-fi, but it worked pretty well.
Lenny (01:04:25):
So it's kind of like a standup that happens once a week, and it's higher level essentially is what it sounds like?
Tim Holley (01:04:30):
Exactly, exactly. Trying to think about the priorities and not tasks. And that is a blurry line. I fully recognize that. But anchoring in those I think is certainly for me, personally more helpful.
Lenny (01:04:41):
And is the comedian person in these and sharing funny things in the standup-
Tim Holley (01:04:46):
No, unfortunately, or fortunately, he's now actually a comedian.
Lenny (01:05:52):
Are you serious he became a full time comedian? That’s amazing. And with that, we've reached our very exciting lightning round. Are you ready?
Tim Holley (01:04:58):
Hit me.
Lenny (01:04:59):
What are two or three books that you've recommended most to other people?
Tim Holley (01:05:03):
Couple that come to mind Team of Teams by Stanley McChrystal has been, I think is just A, really fascinating read, and B, helped me think a lot about how you trust teams and how you think about disseminating decision-making to the right folks, tech language, push decisions to the edges. But thinking about it in the context that he describes there is really fascinating, and it just shows that it can work even in the most egregious world of military, which you think is top-down command and control, shows that there's a different way to approach problems.
Lenny (01:05:42):
I was actually a fan favorite at Airbnb also.
Tim Holley (01:05:45):
Oh, cool. Other is back all the way to the top to what I love to do. Surfing and being outdoors. Let My People Go Surfing by Yvon Chouinard, the Patagonia founder. Incredibly fascinating read of someone who just had a deep, deep passion, turned it into a business, struggled, iterated, came out the other side really successful. So the business side, but also just how they think about treating their employees and the culture that they've built I think is to me personally, really inspiring. There's a theme here around trust and how you engage with people to make their day-to-day work lives, is really fulfilling. So that's another favorite.
And then in a super different direction, Power Broker by Robert Caro. That is an absolute tone. It is huge. It took me probably an entire year to read because I'm an extremely slow reader and/or I fell asleep a lot. But it is so fascinating, especially living in New York, of how one human had such an incredibly outsized and probably terrible impact on the city. Access to waterfronts, really thinking about communities and tearing them apart. Just such a fascinating read.
Lenny (01:06:56):
I have that book, and I've never read it. It's very long and intimidating. I think it might be back there, maybe in a different-
Tim Holley (01:07:01):
I would chunk it out. Do a couple of chapters at a time, otherwise it feels insurmountable.
Lenny (01:07:07):
It's like infinite Infinite Jest where you're intimidated. Amazing. Okay, next question. Favorite recent movie or TV show?
Tim Holley (01:07:15)
So my wife and I talk about this a lot. I think we're Western Files, if that's a thing. I'm from Europe and so it's a whole new world, different world for me. We've loved Yellowstone and all of the, I guess they're prequels. They've been just really, really fun to watch for people who are curious about that culture and that world.
Lenny (01:07:35):
Awesome. It's also been hard to find where to even watch it. It's on the weirdest channels.
Tim Holley (01:07:39):
It is one of those where the old world of, we cut all our cords and we only needed Netflix. Suddenly you need all these really random providers of content that you're like, "I have to subscribe to that now to watch this show?"
Lenny (01:07:51):
Don't understand where this even is. Just take my money. Favorite interview question you like to ask candidates?
Tim Holley (01:07:58)
I'm a big fan of case studies, live case studies. I think you learn a whole boatload about how someone thinks on the fly, how they react to constraints. So we use those. I've used those a ton. We use them pretty heavily in product interviews. So I love those modulated for the type of business you're in, what you're actually trying to understand.
[NEW_PARAGRAPH]The other one I like to ask is around something that people have taught themselves, tried to get at a growth mindset. I think Julia, who was on the podcast a while ago, said something similar. But you get a ton of insight into someone. Ideally, you get a bit of passion and you often get something to go research. She's like, "I don't know anything about that topic. I want to learn a little more."
Lenny (01:08:40)
What is a favorite product that you've recently discovered that you love?
Tim Holley (01:08:44):
You as a new parent maybe resonates when... So it's not new, because our kids too. But when I was looking, being in product, of course you want to track data. And so I was looking for apps that would be good at doing that, and they nearly all look like hideous medical charts where I just don't want to engage with that. 
I found this one app, I think it's called Nara Baby or Nara something. Super simple, allows both parents to enter information. Probably grandparents too. We only tested it with two people. Seamlessly syncs. Really easy to use. So at 4:00 AM when you can't see and you just want to say, "I fed the baby," you can do that really easily. Just really, really simple, fit for purpose product. So that resonated with me.
Lenny (01:09:31):
I'm going to be downloading that right now. I've been using Huckleberry, which is both awesome and not awesome, and so awesome tip. Great. What is a favorite life motto that you like to repeat often or share with other people, either in work or in life?
Tim Holley (01:09:44):
One of the things I talk about maybe internally more than anything else, but all or nothing. Go all in. Go do the thing. In German [German 01:10:08]. I grew up in Germany, so that's something I say to myself a lot is if you're going to do it, do it properly. I think those are often helpful words to live by.
Lenny (01:10:04):
I love that. Final question, what's a favorite item you recently discovered on Etsy?
Tim Holley (01:10:10):
I recently bought an engraved whiskey decanter for my wife and myself, or for the home. Super beautiful, so cool. Got it personalized with our names. Just such a cool, cool item, that I wasn't expecting to find that kind of thing. I'm not even sure exactly how you engrave a whiskey decanter, but it was really cool. And the other thing, I'm always on the lookout for greeting cards. If anyone has great greeting card seller recommendations, I'm all ears. I love giving out physical greetings cards to folks, so that's another always on Etsy favorite of mine.
Lenny (01:10:51):
Tim, we've talked about growth, culture, surfing, cabins, leadership. Thank you so much for being here. I'm downloading the Nara app right now as we speak. Two final questions. Where can folks find you online if they want to reach out and maybe learn more, and how can listeners be useful to you?
Tim Holley (01:11:06):
Yeah, yeah, find me on LinkedIn. That's probably... Well, not probably, is my most professional platform. Instagram, like I said, is a farce. And being useful. Yeah, send me things that you're excited about in the Etsy product. Send me feedback. We're always really keen to learn how folks are experiencing the things that we build.
Lenny (01:11:26)
Amazing. Tim, thank you so much for being here.
Tim Holley (01:11:28)
Thank you for having me, Lenny. Appreciate it.
Lenny (01:11:30)
Bye everyone. 
(01:11:34)
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