Building a meaningful career | Jason Shah (Airbnb, Amazon, Microsoft, Alchemy)

[00:00] pushback is, you know, it, [00:02] I couldn't imagine a word more viscerally that makes you feel like, [00:07] you're sort of physically going against what somebody else wants. [00:11] And it gears people into a mindset of then, well, how should I push back? It starts from a place that I need to disagree. I need to say no. [00:19] It's a very negative mindset. [00:21] purely based on the word that has come to label [00:24] A behavior that [00:25] that alternatively could be about [00:27] how do I shift the direction on something or how do I help the business actually succeed [00:32] when I disagree with somebody about something. And that's a very different mindset. [00:36] And so the two things that I've seen be most successful, [00:39] would be, I think number one, is actually understanding what a goal is or what somebody's kind of issue is with something, and then actually aligning those things in some way. [01:09] I was lucky to work with Jason while I was at Airbnb, and when I started working on this podcast, I knew that I wanted to have Jason on. He was actually my very first guest on this podcast when I was pre-recording some episodes. But as you'll hear in our chat, we decided to take another crack at it for reasons you'll soon understand. In this episode, we cover what it's like to be a PM in Web3 and how that's changed as Crypto Winter has returned,

[01:39] too well, including how to keep morale up and people focused when so much is changing around you. We also get into a ton of killer advice on leadership, hiring, pushing back on your CEO, working backwards, career advancement, and a lot more juicy stuff. Jason is a gem, and I am really excited to share this episode with you. With that, I bring you Jason Shaw. [02:02] This episode is brought to you by Coda. Coda is an all-in-one doc that combines the best documents, spreadsheets, and apps in one place. I actually use Coda every single day. It's my home base for organizing my newsletter writing. It's where I plan my content calendar, capture my research, and write the first drafts of each and every post. It's also where I curate my private knowledge repository for paid newsletter subscribers. And it's also how I manage the workflow for this very podcast. [02:32] We've seen Koda evolve from being a tool that makes teams more productive to one that also helps bring the best practices across the tech industry to life with an incredibly rich collection of templates and guides in the Koda doc gallery, including resources from many guests on this podcast, including Shreyas, Gokul, and Shashir, the CEO of Koda. [03:02] to use. If you're ping-ponging between lots of documents and spreadsheets, make your life better and start using Coda. You can take advantage of a special limited time offer just for startups. Head over to coda.io slash Lenny to sign up and get a thousand dollar credit on your first statement. That's coda.io slash Lenny to sign up and get a thousand dollars in credit on your account.

[03:32] I'm John Cutler from podcast sponsor Amplitude. Hey, John. Hey, Lenny. Excited to be here. John, give us a behind-the-scenes at Amplitude. When most people think of Amplitude, they think of product analytics. But now you're getting into experimentation and even just launched a CDP. What's the thought process there? Well, we've always thought of Amplitude as being about supporting the full product loop. Think collect data, inform bets, ship experiments, and learn. That's the heart of growth to us. So the big aha was seeing how many customers were using Amplitude to analyze experiments, [04:02] for outreach and send data to other destinations. Experiment in CDP came out of listening to and observing our customers. And supporting growth and learning has always been Amplitude's core focus, right? Yeah. So Amplitude tries to meet customers where they are. We just launch starter templates and have a great scholarship program for startups. There's never been a more important time for growth. Absolutely agree. Thanks for joining us, John, and head to Amplitude.com to get started. [04:28] Jason, welcome to the podcast. Thanks so much, Lonnie. Really excited to chat with you today. Something listeners don't know that we know is that we actually recorded an episode between you and I back in April. [04:43] It was actually my very first episode that I ever did for this podcast, and it was [04:47] before I launched, it was kind of like a pre-launch launch episode. And interestingly enough, by the time the podcast launched and it was going to go out, well, let me also add that we chatted mostly about Web3, forgot that detail. So most of our chat was about Web3 and the state of Web3 and PMing in Web3. And by the time the podcast was supposed to come out, Web3, things have changed in the world of Web3. And so it kind of felt a little stale and out of touch. And so we decided, let's do it again. And how do you feel about that?

[05:15] I appreciate that, Lenny. I'm honored that you would have me back. I'm going to count it as the personal record of two times on Lenny's podcast, even if the world only knows it as one. [05:25] That's a wow. Good one. Okay. First ever guest and first two time return guest. Amazing. Okay. To set a little context for folks on your background, your career, could you just give us like a 60 second overview of your, of your background and your career and how you kind of got to what you're, to what you're doing today? [05:44] Yeah, for sure. Thanks again for having me, Lenny. So, [05:47] My career has all been about solving important problems in a unique way. [05:51] I think the latter part is the youngest child in me who has to be special and do things different than other people. [05:57] And the former is about making sure that my time is spent well since we're all limited there. So I actually got started in a sense. [06:03] in tech. [06:04] When I was 15, I started my first company, much like a lot of teenagers. It was around test prep and getting people ready for college and getting people ready. [06:13] It was my first exposure to using technology at scale to help people, and I just found it addictive. [06:19] ever since. And so I ran that company for seven years through school, was lucky to do a small acquisition to a partner of ours that we had worked with throughout the, [06:28] And then I was just hooked. [06:29] And I moved to San Francisco without a job. I was really arrogant. I said, I'll never work for anybody else. And then lo and behold, [06:36] Giver comes along. I'm super excited about it. I've been working on a product actually in the same space. [06:40] And so that was actually my first formal product management role. And I stayed at Yammer, stayed through the Microsoft acquisition back in 2012.

[06:49] Lo and behold, I was at the world's largest productivity company at Microsoft and I'm [06:54] Most people there, in my opinion, were wildly unproductive and I wasn't shipping a lot. I got the itch again. So I started another company called Do.com and ran that for about four years. [07:03] And then eventually, we found a better fit with Amazon. They were growing their AWS offering SaaS products. So we partnered with them to kind of do a small [07:13] acquihire and help build the team out and the product there for [07:16] over a year. [07:17] And then again, to be honest, I got bored and excited about what Airbnb was doing and the mission around belonging. That's where I was lucky to meet you and so many other really wonderful product leaders and just human beings in general at their core. [07:30] And then to keep things brief for now, you know, I got to work on a lot of really exciting products and businesses there. But. [07:35] Eventually got the itch for Web3 after being a kind of observer from afar, investor, and I wanted to be a builder. And so in Web3 specifically, and to me, it's a new vision of a better version of the Internet. And I'm really excited about that. So I've been with Alchemy, which is a blockchain infrastructure company for the last year. [07:54] Really excited about all the opportunities I've gotten to work on products that have been part of most people's everyday lives. And I'm hopeful that we'll get to do that with Web3 and Alchemy as well. Amazing. I just realized as you're chatting there, do.com, I'm pretty sure I used that back in the day. I think I just realized that. I hope so. That would be a new I'll add that to my second podcast achievement is if I got Lenny to use a product that I worked on, especially a startup.

[08:24] with Web3. We're not going to spend most of the time on Web3, but just thought it'd be good to chat about some of these things, partly because you guest authored the sixth most popular [08:33] post on my newsletter of all time, currently number six, and it was about how to be a PM in Web3. Basically, it's called Product Manager's Guide to Web3. [08:41] And so a few questions there I wanted to touch on. One is just like, how would you describe the current state of Web3? We're recording this at the end of July, and so we'll see when this comes out. But I'm just curious, like from someone working within it, kind of going through the boom and the busts, not the busts, the winter that we're kind of in a little bit right now. [08:59] Yeah. How do you feel about it right now? [09:01] Yeah, for sure. So, [09:03] As much as I'm a techno optimist, I'm also a realist. And with that being said, [09:09] I genuinely believe Web3 is in the strongest position that it's ever been in. I think it's important to remember that the term Web3 has fairly existed in kind of popular lexicon for barely a year. We've definitely had crypto for more than a decade now as crypto. [09:23] technology arguably as a financial instrument of some sort but [09:27] Specifically, the number of companies that I'm seeing be formed, the number of products that are starting to actually achieve some form of early product market fit. [09:35] some products that are starting to scale. There's definitely been obviously a huge drop in price. There's definitely been some huge scandals in terms of financial mismanagement and the contagion from that. [09:46] But I think it's been my experience that a lot of new technologies don't move up in a straight line and, [09:52] Web3 is especially challenging here because so many things have been financialized from the outset.

[09:56] Whereas generally speaking, you'll see startups or new technologies mature over many years, whether it's the Internet itself, artificial intelligence, QR codes, all sorts of things that kind of have gone through different periods of adoption. And so. [10:09] I think we're seeing things like kind of record Ethereum transactions happening, new layer two technologies launching all the time that are going to help scale layer one blockchains. B'Elanna has announced its phone that's going to be the first sort of Web3 native phone out there. So there's so many new exciting product developments and users entering the space that. [10:28] As much as prices have come down, I'm really optimistic about the state of Web3. [10:32] What I think about a little bit is going through this shift in excitement about Web3 as a PM within a company working in this space. I imagine it tests some of the core skills of a PM, like keeping people focused, prioritizing effectively, keeping morale up if people are getting like, oh, man, all my crypto is going down. I'm curious how you've been able to leverage those skills and what you've learned going through this experience, keeping people focused, morale up, prioritizing effectively, those sorts of things. [10:59] Yeah, it's a great question. It's really important, right? Because we've seen in this space that [11:04] There are these cycles, and I think that morale and ability to keep [11:09] building are the determinants of long-term success. And if everybody kind of takes the ball and goes home, that uncertain future won't necessarily materialize. So in my opinion, I think that the only way to maintain morale is to make progress. [11:23] I think that [11:24] No speech, no sort of extrinsic, you know, motivators like we're going to give everybody.

[11:31] some free crypto to keep them motivated about it or something like that really works. I think people get really excited when they see progress. So [11:38] For example, at Alchemy, we see more developers than we've ever had on the platform today. And then we're shipping. We just launched Solana support. People are like, this is real. We're like actually doing things, building things. [11:49] We just had our team out at ETHCC, which is a big conference in Paris for [11:53] the Ethereum community. And it was wild. The number of people that were there, products being built, [11:58] like pretty much every crypto conference has a hackathon and so it keeps the spirit of building so alive and so i think it [12:05] at alchemy and just in other situations that I've been in as a leader over time. I think it's all about [12:10] focus on progress and moving forward and [12:12] We saw this at Airbnb when the business had a drawdown in revenue. I know you covered this with Sanchun recently, right? It was 85%, 90% revenue. [12:21] And he didn't know when it was going to turn around, right? It's not just like, [12:25] oh yeah, this will come back in six months and we can just keep plowing forward. [12:28] But I think what worked was making progress and actually focusing on product and your customers and, [12:34] Ultimately, if you hire the right people who are motivated for the right reasons, I think that recipe keeps people highly motivated and highly effective at building for when things do eventually turn around.

[13:04] in Web3? And then, I don't know, where do you see the evolution of product management in Web3? [13:09] I actually... [13:10] I'm seeing things change a lot and [13:13] You know, one thing in Web3, if one learns nothing, is the ability to admit when they're wrong or when things change. [13:19] And so I think that that's exactly what I'm seeing. So basically, I'm specifically noticing, [13:24] A lot of teams hiring people, [13:26] product leaders more product managers [13:29] those product managers are actually now working kind of in increasingly in sort of more traditional [13:34] product management fashion in addition to some of the differences that we discussed in the post around the community management and a role in marketing and things like this. [13:42] But specifically, Uniswap just made a big hire. [13:45] Out of Meta, I saw that Gemini also did the same. We're seeing OpenSea hire a lot of talent along these lines too, even through the ups and downs that their business has seen. And at all levels, whether it's kind of product manager, senior product manager, director, VP, or CPO, you're seeing it across the board. [14:03] I think that's partially happening because you're seeing a maturation of products, right? And so maybe you can start early with, [14:09] A few engineers, a community manager get the ball rolling, but eventually... [14:14] The product is more mature, the complexity has grown, the role of a product manager is far more useful and they can differentiate. [14:21] I also think the market is getting increasingly competitive. So there's many NFT marketplaces. There's many layer one and layer two blockchains. As a result, [14:30] I think product is always a competitive advantage, right? If it's working, it improves strategy,

[14:36] It improves execution and improves team collaboration. [14:39] And so maybe that was less of a difference maker before where these teams didn't need that competitive advantage. [14:46] as much because [14:48] Maybe they launched a token and the token was mooning. And so a bunch of people were adopting the product. But that only lasts so long and first principles still come forward. [14:55] come into focus whether it's one day or one month from now and so [14:59] So I'm definitely seeing it shift. [15:01] It's definitely making a huge positive difference in the cases that I've observed. [15:05] And my hunch is we're only going to continue to observe this because with more user adoption comes new challenges. And for all these players that are growing and getting some form of adoption, the product complexity is only going to grow and having somebody to help lead teams, help prioritize between all the different products that they could build or strategies they could pursue. [15:24] is going to only increase in importance. [15:26] I know we're PM people talking about the value of PM, but something I find is that [15:32] people that are kind of anti having a PM or don't see why they need a PM. In my experience, I just haven't worked with a great product manager, because in my experience, you find a great PM, they just make everything better. [15:43] And so it's not surprising to hear what you're [15:45] sharing, which is people are kind of discovering the value of bringing on a product manager, even if it's mostly engineering work. And so that's promising, and I wonder if that's just a natural evolution of a new [15:56] a new space where people are like, "Oh, I don't need PMs in this one." And then, "Oh, okay. I see. All these things aren't happening. I need someone to help. Who can do that for us? Maybe it's a PM."

[16:06] Yeah, that's a great observation. I think that combination of having a direct need for something that emerges [16:12] as well as if somebody's had either a bad experience or not even had any experience with somebody who can play this role, which is quite common in Web3, especially because a lot of folks are relatively early in their career, given the [16:24] kind of accessibility of the space and the, [16:27] I think, frankly, the more adept understanding of the space naturally that a lot of people have when they're earlier in their career and less set in their ways. And so that's a great point. And as a result, the better PSVC and Web3, hopefully the value will prove itself out over time. [16:40] Hopefully they do well so people don't keep getting burned out by bad pants. We're rooting for all the... [16:46] All PMs, but definitely Web3 PMs too. Yeah. What surprised you most about working in Web3 as a PM? I mean, I think that the biggest surprise to me, despite what we were just talking about, was how big some products have gotten. [17:00] without [17:01] have the traditional either product manager role or without the playbooks that we're so used to from the last 20 years. [17:09] of the internet and so for example you know uniswap has done more daily volume on certain days than coinbase and you just swap is about 100 people versus 5 000 plus at coinbase right so that's astounding to me i think a lot of these nft collections and communities that have grown [17:25] You know, I met with a lot of these at NFT NYC recently. [17:29] And a lot of them, aside from the price speculation and things like this, [17:32] have actually built you know the board a bi club is actually building a metaverse project that does look better than some of the digital games that i've used in the past of second life and things like this like obviously a lot of time has passed and so there's a greater foundation of technology to build off of and they're working with a partner on that product as well but there's a ton of progress being made without some of the traditional product structure or individuals so again i think

[18:02] products can get. [18:04] without the product playbooks and resources that somebody who's worked in the internet space from the last 10 or 20 years is so used to. [18:11] Awesome. Okay, we're going to move on from a three and chat a bit about some of your other career accomplishments and companies you've worked at. So you worked at, you mentioned Yammer, Microsoft, Amazon, Airbnb. I'm curious which of those companies has most informed the way you work. [18:25] approach product and build [18:26] product and run teams because they're all so different in how they operate. And I'm always curious, what companies like the formative experience for you that's like, here's how I like to build product most? And I know it's always a combination, but how do you think about that? Yeah, it's definitely a combination, but I would say if I had to pick [18:42] Amazon, even though I was only there for about a year after the acquisition. [18:47] I say that because of this blend between product and business thinking that is especially present [18:54] there and so people say google is an engineering culture people said facebook is a product culture [19:00] Airbnb or Pinterest, sometimes a design culture or things like this. And I think that Amazon was a place where [19:07] You couldn't divorce business and product. You couldn't be a product manager without thinking about revenue growth, without thinking about go to market. And I really like that because as a startup founder doing product in a bigger industry, [19:19] Company. [19:20] it gave me the chance to [19:22] exercise a lot of those skills. [19:24] And it's very similar, actually, to how I feel at Alchemy now, where [19:26] I remember my first month there, people ask me, how's it going? I'm like, I feel like an athlete. I feel alive again. I can do... [19:32] M&A one day, I can be doing product another minute. I could be figuring out, oh, we need to hire our first lawyer, right? Onboarding plans for employees the next minute.

[19:41] And it wasn't as siloed as sometimes a product role can be. [19:45] I think Amazon, I went there to learn and understand. That was my biggest goal was this is an incredible company that's gone into, you know, the Whole Foods acquisition happened when I was there. And I was wondering. [19:54] How does the same company kind of win in retail, win with AWS, they'll create studios. And I think the Amazon culture ultimately, more than anything else around ownership, being vocally self-critical, is right a lot is one of the leadership principles. All these things combined, I think. [20:10] created a really unique culture. So, [20:12] I would say Amazon's. [20:14] had the biggest impact on me. And there have been certain lessons that I've taken from, like you said, all these places. But Amazon was by far the place that I think left the biggest mark on my [20:24] view on product and leadership. That's quite amazing that you were there for a year and that's the one that's most informed and impacted you. Do you feel like people should try to go work at Amazon as a training ground, as a PM? Is that something you encourage PMs to try to do? [20:36] In general, like I certainly had a positive experience, but I think that [20:41] as you know, and as I'm sure you've advised countless people, it's so context dependent. Is it [20:46] Are you learning the zero to one? Are you learning the one to scale? [20:50] What's your aspiration? You know, somebody trying to start a company eventually, or are they trying to work the ranks of the product leadership trajectory? [20:58] And so I definitely enjoyed it a lot. And I think to your point, [21:01] There's often a [21:02] nonlinear sort of correlation between factors that we traditionally think [21:06] are linked, right? So my time there was one of the shortest, but my learnings were some of the greatest because it was really intentional and maybe because of the sort of,

[21:14] moment in time and what I wanted to get out of it. The same way for what it's worth while we're [21:20] When I went to Yammer, I also interviewed with kind of this was the era of like TaskRabbit. I talked to Square. [21:26] And I remember people always say, well, what stage do you want to join? Seed, Series A, Series B? [21:31] And the crazy thing is that Yammer was it was already past 100 people. It grew to 500 by the time the acquisition. [21:37] And it felt almost like the culture was so tight knit. It felt like a seed stage company at some points, even though eventually it kind of felt like a, well, [21:45] Once it was acquired from Microsoft, we'll just say it didn't feel like [21:48] a seed stage company anymore. But it felt smaller than a lot of the actual smaller companies that I was at. So I think that's something I've noticed a lot is that a lot of the proxies don't necessarily match the internal realities in certain cases. You mentioned you picked up a bunch of tactics and kind of like lessons from some of these companies. What's like one concrete process or tactic that you took it away from either Amazon or one of these other companies that's that stuck with you that you like to kind of share with folks? Yeah, definitely. I mean, I think one that Amazon [22:18] us. [22:19] And for those that don't know, the idea is you try to define [22:22] effectively an ideal end state, which funny enough is very similar to some of what [22:26] we both experienced at Airbnb and took away. [22:29] And usually the mechanism for doing this is what's called a PRFAQ. [22:33] And that's a press release and frequently asked questions. And [22:37] It forces a certain degree of clarity to have to actually write a press release about the product that you're going to eventually launch. Every employee goes through actually like a business writing class. After they started Amazon, they give you a little...

[22:49] card with five tips that you're supposed to keep on your desk about [22:53] concision and specificity in the words you use. [22:56] For example, you should never write the word great in an Amazon press release. You should write user-friendly in XYZ way and we'll save customers time 20 minutes each day through this. It's intended to be very concrete in a way that avoids some of the fluffiness itself. [23:12] that. [23:13] Frankly, it's funny when people try to move from slides to docs, they really just import the same mindsets that they use in slides, but just with more words. And so I think the working backwards process of establishing the long term goal using a mechanism like a press release where and the FAQs where every word matters. [23:31] And even the FAQs for what it's worth, there's a section for external FAQs that you would include, for example, as an appendix, but also internal FAQs that are meant to de-risk launch or raise the elephant in the room or dogs not barking, as Amazon likes to call it often. [23:47] That was a really helpful process that [23:49] felt very true to me as a way I like to live my life as well, and then also very applicable. [23:55] The tidbit about not using the word "grate" is so interesting. Is there anything else there that you could share about? Basically, it's just like how to write effectively and [24:04] communicate and launch. Is there any other tidbits along those lines? Yeah, that's a good question. In addition to not using the word great and words like it that are either subjective in what they mean or unclear in what they actually mean, definitely using numbers, you know, more than adjectives. [24:18] Strict concision, I would go over these documents specifically.

[24:22] countless times. [24:23] And there's a phrase I can't remember. It's either Mark Twain or another famous writer who said, kill your darlings, right? Cut, cut, cut and just remove. And so I think I found that really useful in emails I write or documents I write to this day is just going over because not because you're saving ink by cutting words, but because it forces clarity of thought. [24:53] are far more intentional. [24:55] And in the case of great, [24:56] If you say something is great because we're going to deliver something in two hours versus Amazon's great because the selection is very wide. [25:03] the implications on strategy are completely different. And so that's one of the benefits of being very specific and very concrete in language. [25:11] I didn't intend to go too deep into this topic, but no one's ever covered this working backwards process on this podcast, so it's kind of interesting to talk about it a little bit more, maybe. How does it actually work? So you sit there and you actually write out a press release that would go out when you launch this thing. Is there... [25:26] There's like a template used. Is there anything you could share for folks that want to try this out? [25:31] and or point them to a resource that will help them down this road? Yeah, definitely. That's a great question. So there definitely is a template. And so it's a combination of [25:39] an internal training where you have to write one of these documents, you review kind of good, bad, medium versions of this. It's generally used if there's, let's say, a proposal for a new product or even a proposal to buy a company. This helps, you know, really help.

[25:54] simulate what it's going to be like. [25:56] With respect to a template, [25:58] What I recall is it was often sort of an introduction where you get kind of right to the point. You say what you're announcing. [26:03] then usually you would describe the problem in one paragraph and in very clear language. Again, all the writing is this way. Then the solution, you briefly describe the product. After that, there's always a customer quote. And this is an example of this customer obsession that Amazon is so famous for that, [26:20] Many companies like to say or emulate, but I think it really... [26:24] kind of may not be true if you evaluate the mechanisms that they use for example product specs [26:30] that either don't have customer data or don't have quotes from customers, things like this. And so there's a customer quote. You have to literally put yourself [26:37] into the shoes of [26:39] Let's say you were launching Prime, you know, put yourself in the shoes of, [26:43] you know lenny from san francisco what exactly is he going to say when he has access to this and how's it different than his life today and what are the words that he's going to use you can't use great i use great i mean [26:54] If great is one of your favorite words, maybe you could stretch it. But I think if you were in a room with your peers at Amazon, they might, you know, put some red pen through any greats that are used there. So. [27:03] I found that really helpful and it also helps force out of this box that product managers, product leaders tend to get into of thinking that they are always the customer. [27:14] And being a little sort of intellectually lazy where I'm like, yeah, I would like Prime. So let me write the quote I would like. But maybe I'm only, you know, a small segment within our total customer addressable market. Right. So.

[27:27] Anyhow, there's a customer quote, then there's one leadership quote. Similarly, this achieves a complementary goal. Like, how does this fit into our strategy? [27:34] in a way that you would express to the public, but is still true to what the internal... [27:39] sensitivities and mechanisms would be. [27:41] And then a call to action towards the end and not just download here. Right. But, you know, this will be available to customers next month. They can go, you know, access these portals within these Whole Foods stores at this date. [27:52] And it, again, forces clarity of thought with respect to not only the rollout plan, [27:57] But taking a step back and when you read it, do you feel like you would actually want this product? Would you use it? So I found that really helpful as a structure. Can you just summarize those again real quick? For sure. So the structure of the PRFA2 docs was generally an introduction where you announce the product, problem, solution, customer quote, leadership quote, and a call to action. [28:17] So interesting how similar that is to like a one pager potentially. The other thought I had while you're chatting, so the Airbnb approach is work back from the ideal, like Brian talks about it, like the 11 star experience versus the Amazon approach, which it doesn't need to be the ideal, it just needs to be like an awesome launch. So that's an interesting difference, both effective in different ways. I think people tend to, when they hear that both companies have some sort of working backwards, [28:42] process of thought, let's say working backwards on one hand and then 11 star experience on the other. [28:46] listening to how you describe it, I will almost frame it as working backwards from sort of like a moment in time or launch, like you said with Amazon. [28:54] versus working backwards from a quality standard in some sense of an 11 star experience.

[28:58] Going in a slightly different direction, one of the things I wanted to chat about is you worked at all these different companies and they have different types of leadership and different approaches to leadership. And so I'm curious, what have you learned about effective leadership, watching all these awesome operators work? And what kind of separates them in your experience from folks that maybe aren't as effective? Yeah, it's a great question. And to briefly recap, right, I've gotten to see somebody like David Sachs, who had been the CEO of PayPal and then the founder of Yammer and gone on to do many more things since then. [29:28] I've gotten to see sort of [29:30] Jeff Bezos at a distance. I was never that close to him, obviously, and never got to work with him. But I got to observe his impact on the organization. Obviously, I've gotten to witness Brian Chesky and his leadership. [29:41] in sort of the pre-IPO days as well as through the ups and downs of COVID. And then also now at Alchemy, our co-founders, Joe and Nikhil, are leaders that have really had an impact on me as well. [29:51] And I wouldn't tell myself, but I've also seen myself as a bad leader in the start of Sabran and learn from that. And so I think, you know, I think it's a really important thing to reflect on. And I think for me. [30:02] There are three things that have stood out the most. [30:05] I think, number one, nothing is above them. I've seen, you know, whether it's Brian caring about [30:11] The full bleed image on the homepage, whether it's Jeff Bezos, who famously would receive customer emails, read many of them, forward them. And he's famous for question mark emails, where for his time's sake, he would just forward an email to a leader with a question mark and he would just have to figure it out and then report back. [30:28] in 24 hours with the resolution.

[30:31] thereof, but nothing's above them. And a lot of founders or a lot of CEOs or even CPOs and leaders think you get to a certain point and then [30:39] I'm above a product spec. I'm above looking at the data or running a SQL query. And I think that that is a mistake in a lot of ways, especially from a standpoint of who people come to respect, as well as efficacy. [30:49] at one's job. [30:51] And then the other two things would be, I think they're in the detail. So it's less about being above something, but this is kind of, [30:56] Amazon's famous for auditing the details, for example, and leaders are [31:00] you know, for example, if when we're going to launch Prime, [31:02] order a bunch of prime things and see what happens and really test things out. [31:06] and write up a long feedback email on Saturday or something like that and make sure that things are [31:11] moving forward. So I think, you know, [31:13] in my opinion some of the best leaders david sachs would do this too he he actually ran the product reviews it was the ceo of the company doing product reviews not some [31:22] middle tier of director of product who was just running them. They were, of course, involved and there were things to delegate and activate around, but [31:30] um sax was in all those details and ran those properties himself and would talk to the product managers [31:35] directly. And I think that was really impactful. And it also, I think, from an accountability standpoint, [31:40] and culture perspective when you're a pm and you talk to the ceo and you feel like you're presenting something [31:46] at product review. [31:47] It's totally different and it creates a certain amount of responsibility and quality, frankly, that I think is really important. And it's a way to coach, obviously, as well for people. [31:56] those leaders really make a mark on the organization. And then lastly, I think they adapt, right? I think that

[32:01] There are a lot of leaders who are like, I've worked 20 years to become a leader in this way. And I have a playbook either based on past experience or. [32:08] or based on some sort of philosophy that they've developed over time that they feel committed to in some way. [32:14] And I think coming back to some of these examples of [32:17] watching Brian lead through COVID or [32:20] Watching Joe and Akhil now through this particular crypto winter shift gears and figure out exactly like we're still building the core business, but how else can we lean into this and adapt to the unique opportunities that are in front of us? [32:32] I think that's really powerful. [32:35] What I've seen is nothing is above them. They're in the details. [32:38] and they adapt to new information and new situations. That's what I've seen the most that I've appreciated in the best leaders that I've gotten to either observe or work closely with. Awesome. That's super interesting. The first two are kind of connected, which is really interesting. And it just reminds me of Brian and how detail-oriented he was about everything. He used to review every product launch and every screen of every new product. [33:00] Like we had to show him, here's what we're launching this week. [33:03] and just kind of went through and either blew it up or let it pass. And then I just remember the founders, when they were designing the office space, just looking at pictures of listings they wanted to, because at Airbnb, the office conference rooms were modeled after Airbnb listings. [33:19] And I'm just looking through hundreds of listings that the team brought him, and he just picked the ones that he wanted to turn into conference rooms. [33:27] Also, obviously, Steve Jobs, like this is a really interesting through line of great leaders is just this huge attention to detail. And there's probably something about once they let go, that things start to kind of diminish. Yeah, that's such a great point. And you mentioned the Jobs example. And there's a great book that you've probably read or in your community, I believe it's called Creative Selection by Ken Kosienda about the early days of the iPhone. And I think it's Project Purple or something like that. Yeah.

[33:53] You're absolutely right. There were no [33:55] It wasn't no slides, right? None of this. They brought in the prototypes for each of those reviews and things like how to do typing on a tiny screen, right? And those early keyboards and how to do [34:04] autocomplete and Jobs was totally [34:07] in those details from Ken's telling in this book. So I couldn't agree with you more. And it's something that people miss because most of their exposure to leaders [34:14] is on a YouTube video or at all hands. And so they don't really get to see that side of leaders, I think. And it's also not, [34:21] what I think from an ego perspective is, [34:24] is kind of what people want it to be about. They want to be about making big decisions or, you know, commanding a large group of people. And I think it's hard to do that without these pieces. [34:34] One other thing I just wanted to briefly touch on to your point on how they're connected is, [34:37] It's a really good point. And at the surface, it almost seems like they could potentially be the same thing. [34:43] One thing worth calling out, though, I think, is the idea of something not being above somebody, I think, or a person not being above things. [34:51] I think the biggest thing I take away from that is humility, right? Is that nothing is [34:55] Not my job, right? Anything could be picking up paper off the floor and putting in the trash, [35:01] Or it could be, you know, reviewing a product spec, whatever it is. [35:04] And then being in the details, in my opinion, is about craft, right? [35:08] and really understanding things at a low level such that you're able to reason about it and make good decisions like, [35:13] Brian with the homepage or Bezos in some cases with customer processes that he got in the weeds on. [35:19] I think the two together. [35:20] humility and being excellent at craft.

[35:23] I think is a very potent combination, especially when you throw in the last thing of being able to adapt to any situation. That's really interesting. What also makes me think about is the reason things are less good often if there isn't a person at the top that's being very detail oriented. And I find this with a newsletter and this podcast and other stuff is no one's going to care as much about it. [35:46] No one's going to be like, "Oh my God, I really need to get this right so much because I'm just like, I'm personally feeling like responsible for the quality of this stuff and it's like, it's on my shoulders to make this awesome." And so I think that's probably why a lot of the best stuff is led by a singular leader or singular opinion or singular person. A lot of the best startups are just like someone's vision is like, "Here, this is what we're going to do." [36:10] And then the more it becomes a community-driven thing, the less often it ends up being successful. [36:40] people from Airbnb to Coinbase to Google to Tesla have taken courses from real experts and operators that have spent decades honing their craft. As part of their fall season, which Maven just launched, there are over 100 new courses starting in the next few weeks. Many of the people I've had on this podcast are teaching courses like Jackie Bavaro on product strategy, Ariel Jackson on startup branding, Emily Kramer on B2B marketing, plus Annie Duke on decision making, Nir Eyal on

[37:10] break into product management with Marilyn Mika. Check out all my favorite courses and learn more at maven.com/lenny. [37:19] I feel like you're totally right. Especially, I mean, this is the natural thing. [37:23] progression, but it doesn't have to be that way, right? And I think [37:27] To your point, I think a lot of leaders focus on accountability in an organization once they get large. And so you see things like performance reviews and things like this. It's a very top-down approach to [37:36] trying to drive results. [37:38] But as opposed to a sense of accountability, if you drove a sense of responsibility, if people felt like, [37:43] This is my company too. This is my product. This is my office floor. I don't want trash on the floor. I'm going to pick it up and throw it there. Even if we have somebody whose job it supposedly is to clean that up. [37:55] It's like I take pride of ownership in this and I'm connected to it. [37:59] And I think that makes all the difference in terms of, you know, at Airbnb, I think people who felt that way were willing to push back on certain things or they're willing to propose new ideas because they felt invested in. [38:10] in the company. I see it at Alchemy all the time. You see an engineer hop in and fix something at 3am because they feel committed to the code base and it's not a [38:19] thousand person engineering organization where my only job is to make the ios app you know two percent more effective at engaging users so you touched on kind of the skill of pushing back on on a founder or ceo and then i know that's something you're really good at i've seen you do this i'm curious what you've learned about how to effectively do that as a pm at a company pushing back on the ceo or founder when you disagree i mean i think this is one of the i actually think it's one of the most

[38:43] misunderstood terms in a sense. [38:46] Because I think language, like we were talking about earlier, is so important. [38:50] And yet what you call something is. [38:52] It ends up defining, I think, 90% of what people understand about a concept. [38:57] And so pushback is, I couldn't imagine a word more viscerally that makes you feel like, [39:05] You're sort of physically going against what somebody else wants. [39:09] And it gears people into a mindset of then, well, how should I push back? It starts from a place that I need to disagree. I need to say no. [39:17] It's a very negative mindset. [39:19] purely based on the word that has come to label [39:22] A behavior... [39:23] that alternatively could be about [39:26] how do I shift the direction on something or how do I help the business actually succeed [39:30] when I disagree with somebody about something. And that's a very different mindset. [39:34] And so the two things that I've seen be most successful, [39:37] would be i think number one is actually understanding what a goal is or what somebody's kind of issue is with something and then actually aligning those things in some way so [39:48] And coming back to Airbnb, I remember Airbnb had bought a company at Luxury Retreats. There was a goal to integrate. [39:55] that business and that product into the full airbnb suite [39:58] and there was a lot of potential with that but i remember that there was part of the product experience [40:02] that was oriented around chatting with somebody. And the idea that the business that had a very large team [40:08] of wonderful people who helped you as concierges, basically, for your trip. [40:13] And so...

[40:15] This was a team that I was on that, to be honest, had fairly low morale. It's always difficult to integrate an acquisition with [40:22] a company, especially when we were based in different places, etc., [40:26] And I remember hearing from a leader who had been at Airbnb for a while who's very effective at persuading senior leadership. And they understood why this was a problem, because this chat product was growing in complexity. You'd have to build all these features into it. [40:40] And nobody could successfully shift the direction. And as a result, it was just this [40:45] sort of [40:46] It was a mess as a result, and there was very low morale because everybody were taking on too much scope. People weren't sure it was the right product. It was being built up as one giant launch as opposed to an iterative thing. [40:56] And what was really interesting was that this leader was very effective at understanding that the goal wasn't about building a bunch of features. It was about, as often discussed at Airbnb, a magical platform. [41:05] experience. [41:06] And so when we took a step back, [41:08] It was reimagined as trip designers, not concierges. And their goal is to design your trip. And part of that meant a very elegant, simple chat experience so that you could have an efficient, [41:18] fast, positive experience with that trip designer. [41:21] and move on. [41:22] And it shifted the pushback of like, we can't build this thing. It's too many features. We don't have enough time. We don't have enough resources to, oh, we all want a really elegant, [41:32] really smooth, slick experience for our customers. How do we do that? Let's [41:36] a trip design or a new concept that is actually going to elevate things. We're not telling you we want to pay our backs go if we're not saying we want to settle for less. We're actually just not only going to call it something different, but also envision

[41:48] a simpler experience, which is more elegant, it's more on brand with luxury. Boom. All of a sudden, everybody gets what they want. It's a better customer experience, less scope. [41:56] And it wasn't about saying no, it was about understanding what we're all actually sharing as a goal, which was a great, simple customer experience, and then actually building that. [42:06] So I saw that to be really effective. And I think that's something I try to bring into my career. I have a couple other examples if it's useful, but that was a big one that I learned from an Airbnb. [42:15] Yeah, another example would be great. One thought there though is, do you think it was mostly like the name and the concept or was it that it was a bigger idea? What do you think it was about reframing it that way that got people, "Oh wow, okay, now I'm really excited about it again." [42:29] That's a great point. I think it was a big idea, right, with a good reframing. And I think it's like many things where there's the substance of something and then there's the communication of it. And so this is true often if, for example, if a company is changing strategy. [42:42] Oftentimes people might walk away feeling like, yeah, I guess I kind of agree with the strategy, but the way it was communicated was really poor or vice versa. Like, yeah, they told us in advance and they sat us down all hands. I really disagree with this strategy and I'm going to be dug in on my heels and not disagree and commit now. So in this case, I think you're totally right. Like if it was just window dressing of. [43:02] founders are too smart, especially at all these companies we've talked about, to be fooled with [43:07] a simple renaming of something. [43:09] But I think the combination of a bigger idea, more exciting idea that was [43:13] at the heart of what we were all going after together. [43:15] combined with a simple way of communicating it because i've also seen

[43:19] big ideas that are poorly communicated fall flat on their face and not achieve the intended outcome. Those two together, I think, were a really potent combination. Awesome. I'd love to hear another example. Yeah, for sure. So, you know, a recent example at Alchemy, actually, right, we're growing, we're hiring. But there are a lot of roles that especially being in Web3 that are not yet created. For example, we created a. [43:41] There's traditionally growth product, growth marketing. We've created a new era around growth operations, which I'd be happy to talk about if we want to get into it. But it's a really interesting area. And we were going back and forth on like, should we hire for this role? It's not even a real thing. Maybe we've looked at some candidates. We're not so sure about them. [43:59] And what I realized with our founders who are incredibly smart, very talented, have built the company over so many years now. [44:05] They want to win. That's what they care about at the end of the day. They are so driven to win at the end of the day. And so ultimately... [44:11] It wasn't like, let me make some rational argument about the role of growth operations or let me, you know, defend some issues with this person's resume that maybe you're spotting when we make this hiring decision. But, oh, you want to win? We want to grow faster. Awesome. This is the way to do it. And that's how we're going to actually become the generational company we want to be. Again, a reframing in this case around. [44:33] Yeah, we might disagree or squabble about certain things at a detail level. [44:37] But I understand what we all came here to do. And let's focus on that and how this is a part of that. [44:42] versus just focusing on [44:44] maybe the means to an end versus the end itself. And the end always brings a lot of clarity in my experience. [44:49] What's cool about both these examples, and another guest touched on this, when you're trying to influence the CEO or the founder, coming back to your working backwards concept, you almost want to work backwards from what are they excited about, how do they see the world, what's important to them, and then pitch it that way. So in the first example, I imagine they were pitching to Brian, and he's like, yeah, trip design, that sounds like some Brian would love. And then in the second example, yeah, we're going to win, here's how we win. So that's a really interesting takeaway there. I mean, I think we all forget that we're all just humans, right?

[45:19] Hey, we all are busy, etc. It reminds me a lot of sales, right? Like I was very unsuccessful when I was trying to outbound sales in the early days of my last startup, do.com. Because I didn't understand this. I'm a product person. I'm not a sales person. I didn't listen to what people cared about. I didn't kind of work backwards from what a CRO or a head of people that we might have been selling to cared about. [45:42] I was just about features and here's what we can do for you and this and that. But all they care about were one or two things, right? Maybe the CRO is growing revenue. Maybe the head of people is worried about culture or scaling their talent organization. [45:54] And we were nowhere near that list. [45:56] And so I think it's similar for CEOs. And there's a huge disconnect when, say, a PM walks into a [46:01] a meeting with the CEO and they're talking about something, [46:04] that. [46:04] The CEO is 10 miles away from thinking about and certainly even the mindset that they're bringing to the conversation. [46:10] It's totally different. I think Casey made a lot of great points about this in the recent podcast as well. [46:15] Sweet. Casey Winters, podcast plug. Okay, so something else that you're really good at is you don't kind of focus [46:24] career-wise on working your way up the ladder and being like the top PM. And you seem to be really good at kind of following what's interesting to you and your interest and your curiosity. Is there something that you've learned there, something you could share for folks that are just like, oh my gosh, should I just keep in this with this job and work my way up? Should I try some new? What have you learned about that sort of thinking? So the framework I like is ladder versus map. And I think that

[46:50] you can... [46:51] Be either person at any point in your life. Sometimes there's a bit of a set mindset that somebody might have one way or another, but. [46:58] I like ladder versus map. Ladder is about moving up, more influence, more power, a higher title, things like this. [47:05] Whereas map is, I just want to go wherever is interesting. I literally think of it, I think of my career very similar to travel. I want to go to Greece. [47:12] I want to be hungry, walking around in India, sweating in 100 degree weather. I want to go to Australia and kind of get locked out of my hotel and see what that's like. I'm OK with discomfort because it's interesting. Sometimes it's. [47:27] For better or worse, maybe this is a privilege. It's certainly a privileged thing to say, but I care more about living a really interesting life than, let's say, a good or comfortable life. I think it's [47:36] that's where the growth comes from that's where the stories come from that's to me the things [47:40] that I'll remember the most. And so... [47:43] When I think about product and I'm on my deathbed, I'm going to care about the products I built and how they affected people. Nobody's really going to be looking at my LinkedIn, hopefully for their sake and mine at my funeral. And so. [47:54] That's what I think. Sorry, it's a very morbid analogy, but I think thinking of the future provides a lot of clarity about what am I going to care about a long time from now? And I think that applies to all facets of life. That's how I'd. [48:05] thought about my life partner. That's how I think about my career. That's how I think about where I want to live. [48:10] San Francisco, a lot of people like to talk negatively about it, but I believe in the community. I believe in the place. I'm interested in the long term, even if. [48:19] you know, the short term, it has some challenges to it. So I personally believe really strongly in this kind of ladder versus map.

[48:26] distinction. And I think a lot of people are very intentional in the micro. [48:31] They think about their next job, their next title, [48:33] how much salary and equity there is, [48:35] And in good ways, too, I think about the team that they're going to work on next with. They're very unintentional about the macro. [48:41] What's the big picture? What do I care about as an individual? There's not a lot of classes for that. There's not a lot of blog posts. [48:48] in the product management field about [48:50] the touchy-feely side of this and who are you as a person and where do you get energy from so [48:55] For me, I found that really clarifying and it makes... [48:57] career decisions that have seemed risky. [48:59] to other people seem inevitable to me. [49:03] Is there like a story or example of how you use this approach to make a decision where you end up going? And or is there something that you maybe regret or are really happy with in terms of the kind of the fork in the road looking back using this way of thinking? A few concrete examples, actually. I'll keep them brief, though. [49:21] One is when I first moved to San Francisco and I mentioned I did a small sale of that education company in. [49:27] I could have done a lot of more productive things with my career in the short term. I had all my peers from [49:32] college who had, you know, gone off to their great jobs at Google or whatever. [49:36] I said, [49:37] I just want to, I'm just going to move to San Francisco and work at my dining table. And I have a little bit of savings from this, you know, so why not? Let's see. It's going to be super interesting. And, [49:46] I mean, it was also very boring at times. And so I didn't learn a lot on the sort of micro level, but I built five or six products. I became much better at programming as a result. [49:55] I remember one time,

[49:57] It's kind of a goofy story, but I was working at my dining table and I saw Ron Conway on the street and I like, [50:03] I was disheveled because I was just working for my apartment and I wanted to go pitch Ron Conway on this terrible idea for a startup. And so. [50:10] went out there and he was fortunate to not, you know, shove me to the side and he listened to me for a minute. And then, you know, I emailed him after. And these are random things that happen that over time, [50:21] I think make us who we are, you know, are you the sort of person who's going to hustle [50:25] do that. When I was building that education company, I went and put flyers in people's cars in various high schools. I was trying to get things started. And [50:32] Coming back to leadership, that would be below most people. It's like, wait, you own a company and you're sticking flyers in people's windshield. It's like, what's wrong with you? [50:40] And so anyway, I think that was an example of time where it was like, OK, if I'm on the ladder, I'm like, I got to get the best entry level job or whatever. Even if I had been an entrepreneur before that, I would have thought about my structure. [50:51] in my career and I was like, this is going to be interesting. [50:53] I'll figure it out. I believe in myself enough that [50:56] I'll figure it out. [50:58] I did that. [50:59] yammer and leaving yammer was similar where i could have stayed my equity was finally worth something and there was a [51:05] I could have learned a lot, even I'm sure from the Microsoft structure. [51:09] But I was bored and I had been talking to a couple angel investors who were willing to put money into whatever the thing was going to be. And. [51:16] I felt like, [51:18] Raising money is actually going to be really hard for me. This is going to make my life a lot easier and I can focus on product and [51:24] and so on and so forth. That was a really hard four years. Things like

[51:28] an M&A offer falling through the day before your wedding or chewing glass and submitting a [51:33] to the Apple iStore and being a featured app and then resubmitting because we wanted to fix a bug. And then actually now it crashes 90 percent of the time as Memorial Day weekend. And you can't get in touch with the Apple business development manager who can help you out to reapprove something. It was a really stressful four years. Right. [51:49] but [51:50] using the map analogy, that's like, you know, getting lost in Croatia and having to find your way out, or getting lost in your hotel in Australia, or getting bitten by a dog in Thailand, which actually did happen to me. But these are interesting experiences that I think build characters. I'll pause there, but I think [52:06] There are a lot of career decisions I've made. And do I have regrets? At times, for sure, right? Because you see what would have happened if you had joined a... [52:13] a different company at that time. And it would have been like, oh, I would have met so many great people. I would have worked on these products. I mean, my equity would have been worth more, whatever. [52:20] But I think you only live once. And I think that these rare experiences have been very true to me and taught me things that I wouldn't learn otherwise. [52:27] What's really cool about that analogy ladder versus map is a lot of times you think you're climbing a ladder and you think it's innately going to be great and sometimes that ladder falls over and the company doesn't go anywhere and/or the job sucks, your ladder is heading to some terrible place. And what I find in my experience is anytime I try something totally new and take a risk, especially following things that give me energy and I'm just like, [52:57] at least it's always led to better

[52:59] opportunities and much more interesting work. And so it's kind of this like, get off the ladder to get on a different ladder. And sometimes you think you're going on this ladder and it's not going to get you anywhere anyway. So explore other ladders. So I'm kind of picturing a chutes and ladders. Totally. There's many ladders and you want to explore the different ladders across the map. How about that? [53:19] I mean, I think you're totally right. And the only brief thing I would add to the way that you put it, which I think captures the essence here is I think we all have a lot of false precision about. [53:31] what we think a given career move is. [53:33] is going to lead to or what it's going to be like. And we forget that [53:37] A lot of career decisions are made out of maybe 10 hours cumulatively, like talking to a team and getting signals. So, [53:44] I think that that false precision sometimes gives us comfort in making certain decisions and holds us back from. [53:50] a bolder decision that might be better, but maybe the latter is just hidden behind some fog if you really want that. And you can, you can get both. Maybe you can go to the most interesting place in the world. [54:00] and like have the success in life and progress and so on and so forth. It's just that I think a lot of people think it's totally either or. They think that they've already figured out [54:09] the precise outcome that's going to happen. And to your point, the latter, [54:12] often does fall over. And if that's what all your hopes are pinned on, it's a very fragile career decision that I think is really difficult to navigate. [54:19] - Kind of the flip side, you also don't want to be bouncing around over and over and over. And in my, like as much as I talked about how I shifted and tried new things, like I'm a very serial monogamous in terms of work. My first job, I was there nine years.

[54:32] then a startup for a year and a half, and then Airbnb for seven years, and then what I'm doing now, maybe forever. And so there's a lot of value just sticking around and kind of seeing things through. And so I guess, I don't know if you'll have an answer to this, but do you have any wisdom on when to stick with it and keep... [54:50] keep exploring opportunities at a place you're at versus trying to sub new? My hope is that there's a balance here, right? In the sense that, [54:57] The map shouldn't give the impression of [54:59] 180 countries and therefore let's do 180 tech companies and shorten the tenure from two years down to a month, right? And we've just created a generation of [55:09] job first which is even easier because we're all on zoom it's a good point and i really respect people like you who have stuck it out you know through the ups and the downs and you know somebody sees seven years on paper but i mean seven years i don't know how many chapters of ever b how many crises moments felt like 300 yeah there you go so i i think that [55:30] I think there's a balance, right? For example, I want to be in Web3 for more than a decade. I want to stay at Alchemy for a very long time and help build the company. So I guess when I think of map, maybe... [55:40] an important way to think about it is, you know, maybe when somebody is 50 or 60 or 70 and they might choose to stop working. [55:48] A lot of people when they start their career actually have 30 years to play with or 40 years or 50 if they're lucky. That's a lot of chips you can play. You could do five, 10 year runs, right? And so I think that. [55:58] in terms of like sticking it out maybe i'm biased i think that some of the

[56:03] absolute sort of like gens, if you will, in Silicon Valley and tech [56:07] are the [56:08] teammates that are willing to stay around for four or five, six, seven years. Right. And they have institutional knowledge that nobody has. They have a positive impact on the culture. [56:16] That is impossible if there's constant employee turnover. So to me, I think that you could simultaneously be somebody who's committed to companies, stays for a very meaningful amount of time. [56:25] but zooms out and looks at their career. Actually, I think, you know, maybe this was even more, right? You're now a famous podcaster. You're a successful startup founder. You were a product leader. All these things. [56:36] form a map and I think a really interesting career and life, frankly, that's pretty full with a lot of really interesting milestones and learnings and networks and people that you get to interact with. [56:47] Yeah, to your point about how long a career is, when I thought about it recently, this is my fourth career. First, it was an engineer. [56:55] Then it was a founder, then a product manager when I got to Airbnb. And now this weird thing that I do. And there's so much time to explore and try new things. I will say, though, I feel like the early things you do seem really important. Like Airbnb for me was not early. So maybe I'm wrong. But it feels like you want to work at a company where people look at that on your resume and are like, OK, this person's probably good. So I feel like there's that piece you got to get

[57:25] who's thinking about a product career. [57:27] And let's say on the spectrum, there is maybe Goldman Sachs, because that's what a lot of people are doing. They're like, yeah, I want to do product, but I also feel like I need this gold star or whatever it is. [57:36] And then in between is you could join, you know, a hyper growth company of some sort where, you know, [57:41] They definitely have good product people you can learn from, but definitely still room for you to do more than what a very junior person would be assigned to be doing. [57:49] And on the other end of the spectrum is [57:50] you know, I'm going to have no job. I'm just going to completely bounce around from my own projects or just, you know, work with a new startup every two months. [57:58] Personally, in that spectrum, I tend to be more towards the middle of that, where I'm [58:03] build a track record, build a network. [58:05] I mean, it's crazy. Even just this week, next week, I'm seeing maybe five people that I know from my Yammer days. [58:10] And to your point on formative nature, some of those people, that's how I learned how to do product. That's how I learned things like A-B testing. It's how I had the first angel investors in my next company. [58:20] That's how I still hire people, maybe much to their chagrin. They still get LinkedIn messages from me trying to push them for the next thing. So I totally agree that those early days are really formative. And there's maybe a balance between, you know, nobody wants to be a job hopper. But at the same time, maybe there's ways to also not just be a career person who spends 30 years working up the ladder or is fixated on I need to be CPO. [58:43] but is willing to give up a director title to go be a hustler at some startup because they really believe in it and they want to take a bet or risk in their career. You touched on hiring. That's something I wanted to ask you. So you're in my talent collective. You're a company that's hiring, Alchemy. And I was looking at the stats recently, and you're one of the most successful companies at getting candidates to talk to you. And generally, I think you're just really good at hiring. So I'm curious what you can share with folks about hiring. I appreciate that.

[59:12] And I get a lot of value out of meeting some really talented people from the collective. [59:16] I think hiring... [59:18] It's funny, it reminds me of a sort of pushback in the sense of like what you call it has such an impact on how people think about it. Hiring, recruiting. [59:26] But if people reframe it as like, [59:28] The people you are going to work with every day or the people who make the company what it is. [59:33] It shifts the mindset. It's like, how is that not the most important thing to be thinking about as a leader or as a founder? [59:39] A lot of people have benchmarks. I think maybe on the Google podcast, talk about 30 percent, 40 percent. [59:44] of a founder's time maybe spent on recruiting because I think deep down everybody understands that that's [59:50] incredibly valuable. I think that for me personally, I was reflecting ahead of the podcast on how I approach things now after different stages of hiring and for context, for what it's worth, right? I've been at the [1:00:05] zero-person startup, it's just me, and I'm trying to convince some Google engineer to come join us, which is incredibly hard and has a low hit rate, to a place like Amazon or Airbnb, where you have a large world-class recruiting organization that [1:00:18] is effectively doing sourcing for you and setting up interviews and such things like this. And there's formal calibrations and interview panels. [1:00:25] to a place like Alchemy where it's very sort of scrappy. We need to figure out who we even want to hire. The founders still meet with every candidate. It's a really different environment. So this is kind of a spectrum that I've seen. [1:00:35] Thank you. [1:00:36] And I was reflecting, what do I think works the best? And I [1:00:39] I like to think of it in very similar motions to a business where I think there is a marketing aspect to it. There is a sales aspect and there is a product.

[1:00:48] aspect to it and [1:00:49] What I mean by that is that on a marketing level, [1:00:52] I think, you know, what has a person heard about your company? Do they know anybody who works there? Do they read your LinkedIn posts about things and already know? [1:00:59] know that you're a known quantity before they even step in the door to interview. [1:01:03] Are they even willing to interview based on what they know? [1:01:05] about the company. [1:01:06] And so... [1:01:07] I think that the marketing aspect in it, I mean, it's sort of lowercase marketing in this sense, of course. [1:01:13] Because I think a hard sell of any sort [1:01:15] Or, you know, anything that's not authentic is probably going to fail ultimately. But it's about developing a really positive kind of brand and reputation for a company, but also as an individual. [1:01:26] And then if you pass that threshold, I feel like there's a sort of a sales process. And we were talking about, you know, how bad of salesperson, for example, because I didn't listen to. [1:01:34] to people's pain points and understand the one or two things that were most important to them. And I think similarly, um, [1:01:40] In this context, [1:01:41] Do they want to work if they're an engineer? Do they want to work in the world class engineering organization? If they're a five person, are they just really excited about crypto and they want to find [1:01:48] away in and that's what and then [1:01:50] you know, a place like Alchemist, the best place for them to learn that is, you know, how to think about it. And it's, [1:01:55] not about misdirecting on or matching whatever they say, but it's about [1:02:00] really understanding who they are and what motivates them and what they're excited about because [1:02:03] I'm as concerned about the [1:02:05] kind of post hiring step as I am the pre hiring and want them to work out and be happy and be effective. [1:02:11] And then lastly, I think there's a product angle to it that not a lot of people think about or talk about a lot. [1:02:16] Because... [1:02:17] I think the product is one of those rare cases where

[1:02:21] Job descriptions are almost like product specs, right? They're [1:02:24] Here's what the responsibilities are. Here's what we need you to do. Here's the qualifications we're looking for. [1:02:30] And what's really funny about that is that product is very iterative, but somehow we just write a job description and then it's baked. It's done. It's posted. And... [1:02:37] Nobody thinks about it again until the person's hired and then they take it down. And I'm [1:02:41] I think taking a prophetic mindset where [1:02:44] I meet people all the time now where... [1:02:46] I don't really know exactly what role they're necessarily going to fill. [1:02:49] who I'm not really sure about exactly their seniority. Maybe they don't have a lot of experience, but maybe they would just totally... [1:02:54] be a rockstar on our product team. [1:02:57] And looking at like a product that we can mold flexibly and think of the same way if [1:03:01] you know, at Airbnb, if we were going to build Airbnb plus, if we just kind of came back to, you know, the Amazon working back, just wrote a document and it was over. That's one thing, but we didn't do that. Right. We like went and actually built, [1:03:12] rooms and homes that were supposed to be Airbnb plus. And then we iterated on it and we changed the pillows and we changed the entrance and we changed the scent that you feel when you walk in. We coach hosts and learn about that. So I think a product mindset on hiring is [1:03:24] and iterating on it based on the candidates you're meeting, the needs of the business. So this kind of marketing sales product combination has been [1:03:31] what I found to be really effective at getting people excited, understanding who they are and what they need, and then crafting a role that actually makes the person successful rather than just checks a box in your recruiting software as some new headcount that was hired. [1:03:45] One last question before we get to our lightning round. For PMs that are listening to this maybe earlier in their career, what skill have you found to be most important in helping

[1:03:55] you and helping PMs in general advance in their career. [1:03:59] Yeah, this is a really important question like the others, but I think that [1:04:03] Understanding and defining what problem is. [1:04:07] Matters? [1:04:09] is the most important skill that I think I've taken away. And it applies to so many things. It can apply to a specific product we're building, [1:04:15] It can apply to what a company's mission is. [1:04:18] And I think I found it really effective because it, it, [1:04:22] affects pretty much everything. It affects, you know, [1:04:24] what we're going to build, it affects is the team motivated by what we're doing. So specifically, for example, [1:04:30] At a place like Alchemy where, yeah, we're a developer platform, but [1:04:34] Should we build an SDK so there's abstraction that is easier for developers to use? Should we build an NFT API because we think that's a really important [1:04:42] stack to move into and an important use case to support. Well, the question is, what problem are we solving? It's not this versus that just in a [1:04:49] vacuum. It's [1:04:51] is the problem developer experience and we want to make things easier to develop. [1:04:55] is the problem that an nft marketplace at a whole suite of them are trying to grow and need more support from us [1:05:02] And not understanding these problems clearly. And it goes back to my first company. I was an education company. And the problem was that low income students didn't have access to the same resources to get into college as other students. And that guided everything. I guided the pricing model, which was basically free for a long time. [1:05:16] And then we monetize on sponsorships from colleges, right? Because, [1:05:20] the problem matter, whereas the problem solved was there's not a different problem. There's just no good

[1:05:25] college readiness program. Fine. Then you focus maniacally on the pedagogy and the curriculum and so on and so forth, rather than, say, the business model and an initial product that you think can work. So, [1:05:35] that's what i've found to be the most useful i can give other examples if it's helpful but if [1:05:39] understanding what problem we're actually trying to solve. [1:05:42] and really getting crystal clear about it, I think has been, [1:05:45] incredibly useful to me and energizing as well. [1:05:48] It's such a good reminder, even though it's such a cliche of product managers being, what problem are we trying to solve here? Like, people hate that, but... [1:05:56] Michael Pollan, I mentioned this on a different podcast too, he makes this point that when you do drugs, sometimes you have these epiphanies that you come out and you're like, love is all you need, man. It's like, okay, yep. But it feels so right. [1:06:09] like you really feel it. And the reason that it's such a cliche is because people have found it to be so true for so long. [1:06:16] that it's like annoying now, but it also tells you how true it is. And so I think it's a really good reminder of like, yes, it's annoying to ask that question and people [1:06:24] make fun of PMs for that, but that's because it's so damn important. Just a brief kind of additional, what do you show that? I mean, I completely agree. I think it's very true in life, right? It's like, well, what matters? And it's like, well, your health, your family, your sense of purpose. It's like, nobody's, [1:06:39] unfamiliar of the answer but like most things it's about the application of it and about the nuance of it and i think that's what [1:06:45] product is ultimately sort of all about too. [1:06:48] Awesome. Are you ready for our lightning round where I'm just going to ask you five quick questions, tell me what comes to mind, and we'll have some fun. That sounds great. Ready. Okay, cool. I think I'm going to start adding music to these things. I've got to figure that out for now. No music. Okay. What book?

[1:07:05] What book do you recommend most to other PMs? The Hard Thing About Hard Things. Can you add why? I think it teaches product managers to chew glass and care about outcomes the way that a CEO has to. And I think that's a really useful mindset to have. Man, this chew glass metaphor. I don't like the sound of that. I saw you cringe. I was a little worried about that. Oh my God. What a great job we have here, chewing glass. Okay, other than alchemy, [1:07:32] What's a company you recommend most to PMs to go look for new gigs if they're looking around? [1:07:37] I would suggest Polygon, Salon, or Moonpay. I know it's three, but I want to give some breadth in the Web3 space that might be exciting to people. Great. Great choices. What's a favorite TV show or movie that you've recently watched? The Ken Burns Vietnam War series. I'm really into documentaries and history, and it's a really compelling version of history that I've never seen before. Awesome. Love that. Okay. Favorite interview question that you like to ask? What is a risk you regret not taking [1:08:05] Why? [1:08:06] And what did you learn about yourself? What do you look for in an answer there? I think the biggest thing I look for is a growth mindset to be able to reflect on an experience like that and be vocally self-critical without unproductively being hard on oneself. And I think that the dimension of asking about risk [1:08:23] Get set. [1:08:24] their psychology and how do they think about not only their career, but if they were to work [1:08:29] with me, how would they approach problem solving and taking bets on the business? Awesome. Okay, final question. What's your least favorite vegetable? Broccoli. I just removed some from a pizza last night that I really didn't want to eat. Wow. Oh, wow. Okay. Even like steamed, cooked all the things. There are no circumstances under which I'm excited about broccoli. Oh, man. You got to eat those veggies. I know. I'm working on it. Okay. Jason, this was amazing. Lived up to what I was hoping our second episode would be. Definitely

[1:08:59] cutting room floor. Two last questions. Where can people find you online? And I assume Alchemy is hiring, so maybe point people there. And then how can listeners be useful to you? Yeah, definitely. So if you're interested in Alchemy on Web 3, go to alchemy.com and click through to our jobs page from there. [1:09:15] I'm online at 0xShaw. That is my crypto pseudonymous handle and happy to engage with folks there. [1:09:21] And in terms of being helpful to me, I would love any feedback on anything that came up. I would love any products that people are working on. I also invest and we also partner with a lot of products and teams at Alchemy. And I would love to meet anybody that's listening on the podcast, too, because I know. [1:09:37] Lenny's all about community and has kind of given so much back over the years that I would love to [1:09:41] meet folks that are out there and get a chance to spend time talking about the products that you're all building. Awesome. Thanks, Jason. Thanks, Lenny. 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 Lenny's podcast.com. See you in the next episode. [1:10:11] you