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

1. 0:00 – 8:19

   Jason’s background

   1. JSJason Shah0:00

      Pushback is, you know, it ... I couldn't imagine a word more viscerally that makes you feel like you're sort of physically going against what somebody else wants. And it gears people into a mindset of then, "Well, how should I push back?" It starts from a place of, "I need to disagree. I need to say no." It's a very negative mindset, purely based on the, the word that has come to label a behavior that, alternatively, could be about, "How do I shift the direction on something?" Or, "How do I help the business actually succeed when I disagree with somebody about something?" And that's a very different mindset. And so the two things that I've seen to be most successful 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. (instrumental music)

   2. LRLenny Rachitsky0:53

      Welcome to Lenny's Podcast. I'm Lenny and my goal here is to help you get better at the craft of building and growing products. I interview world class product leaders and growth experts to learn from their hard won experiences building and scaling today's most successful companies. Today my guest is Jason Shaw. 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, how to lead a team through ups and downs, which leaders in Web3 know all 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. (instrumental music) This episode is brought to you by Coda. Coda's 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. Over the years, I've seen Coda 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 Coda doc gallery, including resources from many guests on this podcast, including Shreyas, Gokul, and Shishir, the CEO of Coda. Some of the best teams out there, like Pinterest, Spotify, Square, and Uber, use Coda to run effectively, and have published their templates for anyone 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/lenny to sign up and get $1,000 credit on your first statement. That's coda.io/lenny to sign up and get $1,000 in credit on your account. I'm excited to chat with my friend Jon Cutler from podcast sponsor Amplitude. Hey, Jon.

   3. JAJon (from Amplitude)3:35

      Hey, Lenny. Excited to be here.

   4. LRLenny Rachitsky3:37

      Jon, 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?

   5. JAJon (from Amplitude)3:49

      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, use segments for outreach, and send data to other destinations. Experiment and CDP came out of listening to and observing our customers.

   6. LRLenny Rachitsky4:09

      And supporting growth and learning has always been Amplitude's core focus, right?

   7. JAJon (from Amplitude)4:14

      Yeah. So Amplitude tries to meet customers where they are. We just launched starter templates and have a great scholarship program for startups. There's never been a more important time for growth.

   8. LRLenny Rachitsky4:22

      Absolutely agree. Thanks for joining us, Jon. And head to amplitude.com to get started. Jason, welcome to the podcast.

   9. JSJason Shah4:34

      Thanks so much, Lenny. Really excited to chat with you today.

   10. LRLenny Rachitsky4:36

       Something listeners don't know that we know is that we actually recorded an episode between you and I back in April. It was actually my very first episode that I ever did for this podcast. And it was before I launched, just kind of like a pre-launch launch episode. And interestingly enough, by the time the podcast launched and it was gonna go out, well, let me also add that we talked, 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's 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, let's do it again. And so how do you, how do you feel about that?

   11. JSJason Shah5:15

       I appreciate that, Lenny. I'm honored that you would have me back. I'm gonna count it as the personal record of two times on Lenny's podcast-

   12. LRLenny Rachitsky5:23

       (laughs)

   13. JSJason Shah5:23

       ... even if the world only knows it as one.

   14. LRLenny Rachitsky5:26

       That's ... Wow, good one.

   15. JSJason Shah5:27

       (laughs)

   16. LRLenny Rachitsky5:27

       Okay. First ever guest-

   17. JSJason Shah5:28

       (laughs)

   18. LRLenny Rachitsky5:28

       ... and first two-time return guest. Amazing. Okay. To set a little context for folks on your background and your career, could you just give us like a 60-second overview of your, of your background and, and your career and how you kind of got to what you're, to what you're doing today?

   19. JSJason Shah5:45

       Yeah, for sure. Thanks again for having me, Lenny. So my career has all been about solving important problems in a unique way. I think the latter part is the youngest child in me who has to be special and do things different than other people.

   20. LRLenny Rachitsky5:57

       Mm-hmm.

   21. JSJason Shah5:57

       And the former's about making sure that my time is spent well since we're all limited there. So I actually got started in a sense, uh-... in tech. 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 it was my first exposure to using technology at scale to help people. And I just found it addictive 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, and then I was just hooked. 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, Yammer comes along. I'm super excited about it. I'd been working on a product actually in the same space. And so that was actually my first formal product management role. And I stayed at Yammer, I stayed through the Microsoft acquisition back in 2012. Lo and behold, I was at the world's largest productivity company at Microsoft and most people there, in my opinion, were wildly unproductive and I wasn't shipping a lot and I, you know, got the itch again. So started another company called Do.com and ran that for about four years and then eventually, you know, 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 acqui-hire and helped build the team out and the product there for a little over a year. 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. And then to keep things brief for now, you know, I- I got to work on a lot of really exciting products and businesses there, but 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, uh, and I'm really excited about that. So I've been with Alchemy, which is a blockchain infrastructure company for the last year and really excited about all the opportunities I've gotten to work on products that have been, uh, part of most people's everyday lives and I'm hopeful that we'll get to do that with Web3 and, and Alchemy as well.

   22. LRLenny Rachitsky8:05

       Amazing. I just realized as you're chatting there, uh, Do.com, I'm pretty sure I used that back in the day.

   23. JSJason Shah8:10

       (laughs)

   24. LRLenny Rachitsky8:10

       I think I just realized that.

   25. JSJason Shah8:12

       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, a product that I've worked on, especially

2. 8:19 – 12:44

   The current state of web3

   1. JSJason Shah8:19

      a startup.

   2. LRLenny Rachitsky8:19

      Wow. Cool. Okay, so we're gonna go a little bit backwards through your career and start with Web3. We're not gonna 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 post online 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. 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 bust, the winter that we're kind of in a little bit right now.

   3. JSJason Shah8:58

      (laughs)

   4. LRLenny Rachitsky8:59

      Uh, yeah, how do you feel about it right now?

   5. JSJason Shah9:01

      Yeah, for sure. So as much as I'm a techno optimist, I'm also a realist. And with that being said, 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 barely existed in kind of popular lexicon for, for barely a year. And we've definitely had crypto for more than a decade now as technology arguably is a financial instrument of some sort, but 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, 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, but I think it's been my experience that a lot of new technologies don't move up in a straight line. And Web3 is especially challenging here because so many things have been financialized from the outset. Whereas generally speaking you'll see startups or new technologies mature over many years, whether it's the internet itself, artificial intelligence, QR codes (laughs) , all sorts of things that kind of have gone through different periods of adoption. And so I think we're seeing things like kind of record Ethereum transactions happening, new layer two technologies launching all the time that are gonna help scale layer one blockchains. Solana has announced its phone that's gonna 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 as much as prices have come down, I'm really optimistic about the state of Web3.

   6. LRLenny Rachitsky10:32

      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's 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.

   7. JSJason Shah11:00

      Yeah, it's a great question. It's really important, right? Because we've seen in this space that there are these cycles and I think that morale and ability to keep 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. I think that no speech, no sort of extrinsic, you know, uh, motivators like we're gonna give everybody some free crypto to keep them (laughs) motivated about it or something like that really works. I think people get really excited when they see progress. So 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 and people are like, "This is real." We're like actually doing things, building things. We just had our team out at ETHCC which is a big conference in Paris for, uh, the Ethereum community and it was wild, the number of people that were there, products being built. Like pretty much every crypto conference has a hackathon and so it keeps the spirit of building so alive. And so I think it...... at Alchemy and just in other situations that I've been in as a leader over time. I think it's, it's all about a focus on progress and moving forward. And, you know, we saw this at, at Airbnb when the business had a drawdown in revenue, you know. And I know you'd covered this with Sachin recently, right? Like, it was 85, 90% revenue and he didn't know when it was gonna turn around, right? It's not just like, "Oh, yeah. This will come back in six months and we can just keep plowing forward." But I think what worked was making progress and actually focusing on product and your customers. And 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, at building for when things do eventually turn around.

3. 12:44 – 15:27

   The evolution of product management in web3

   1. JSJason Shah12:44

   2. LRLenny Rachitsky12:44

      One of the most interesting and maybe surprising points you made in the post that you wrote about being a PM in Web3 is that there's much less need for a PM, especially early stage Web3. And it feels like the stuff you're talking about, it feels like a PM is really helpful along these lines. So I'm curious, uh, a- are things changing at all there? Have you changed your perspective on PMs in Web3? And then, I don't know, where do you see the evolution of product management in, in Web3?

   3. JSJason Shah13:09

      I actually am seeing things change a lot. And, you know, one thing in Web3, if, if one learns nothing, is the ability to admit when they're wrong (laughs) or when things change. And so I think that, that's exactly what I'm seeing. So basically w- I'm specifically noticing a lot of teams hiring product leaders, more product managers. Those product managers are actually now working kind of in- increasingly in sort of more traditional product management fashion, in addition to some of the differences that we discussed in the post around, like, community management and a role in marketing and things like this. But specifically, Uniswap just made a big hire, um, out of Meta. Uh, I saw that, uh, Gemini also did the same. Uh, we're seeing Opensea hire a lot of talent along these lines too, even through the ups and downs that their business has seen. So I- a- and, and at all levels, whether it's kind of product manager, senior product manager, director, VP or CPO, you're, you're seeing it across the board. And so I think that's partially happening because you're seeing a maturation of products, right? And so maybe you can start early with a few engineers, a community manager, get the ball rolling. But eventually, the product is more mature, the complexity has grown, the role of a product manager is far more useful and they can differentiate. 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, I think product is always a competitive advantage, right? It im- if it's working, it improves strategy, it improves execution and improves team collaboration. And so maybe that was less of a difference maker before where these teams didn't need that competitive advantage as much because 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, come into focus, whether it's one day or one month from now. And so, so I'm definitely seeing it shift. It's definitely making a huge positive difference in the cases that I've observed. And my hunch is we're only gonna 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 gonna grow. And having somebody to help lead teams, help prioritize between all the different products that they could build or strategies they could pursue is gonna only increase in importance.

4. 15:27 – 18:11

   The value of a great product manager

   1. JSJason Shah15:27

   2. LRLenny Rachitsky15:27

      I know we're, like, we're PM people talking about the value of PM-

   3. JSJason Shah15:30

      (laughs)

   4. LRLenny Rachitsky15:30

      ... but something I find is that people that are kind of anti-having a PM or don't see why they need a PM, in my experience, just haven't worked with a great product manager. 'Cause my experience, you find a great PM, they just make everything better. And so it's not surprising to hear what you're sharing, which is people are kinda discovering the value of bringing on a product manager, even if it's mostly engineering work. And so that's, that's promising and I wonder if that's just a natural evolution of a new, a new space where people are, "Ah, I don't need PMs in this one." And then like, "Oh, okay. I see. All these things aren't happening."

   5. JSJason Shah16:02

      (laughs)

   6. LRLenny Rachitsky16:03

      "I need someone to help. Who can do that for us? Maybe it's a PM."

   7. JSJason Shah16:06

      Yeah, that's a great observation. I think that combination of having a direct need for something that emerges, 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 kind of accessibility of the space and the, 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 th- as a result, the better PMs we see in Web3, hopefully the, the value will prove itself out over time.

   8. LRLenny Rachitsky16:41

      Hopefully they do well so people don't keep, keep getting burned out by bad PMs.

   9. JSJason Shah16:44

      (laughs) We're rooting for all the, all PMs, but definitely Web3 PMs too.

   10. LRLenny Rachitsky16:49

       Yeah. What's surprised you most about working in Web3 as a PM?

   11. JSJason Shah16:53

       I mean, I think that the biggest surprise to me, despite what we were just talking about, was how big some products have gotten without kind of the traditional either product manager role or without the playbooks that we're so used to from the last 20 years of the internet. And so for example, you know, Uniswap has done more daily volume on certain days than Coinbase. And Uniswap is about 100 people versus 5,000 plus at, at Coinbase, right? So that's astounding to me. I think a lot of these NFT collections and communities that have grown, um, you know, I met with a lot of these at NFT NYC recently, and a lot of them, aside from the price speculation and things like this, have actually built... You know, the Bored Ape Yacht Club is actually building a metaverse project that does look better than some of the digital games that I've used in the past, 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 PMs play a really strong role, but it's been incredibly surprising to see how far products can get 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.

5. 18:11 – 20:25

   Why Amazon was a great learning experience

   1. LRLenny Rachitsky18:11

      Awesome. Okay, we're gonna move on from web3-

   2. JSJason Shah18:14

      (laughs)

   3. LRLenny Rachitsky18:14

      ... 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- which of those companies has most informed the way you approach product and build product and run teams? Because they're all so different in how they operate, and I'm always curious what company's, 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?

   4. JSJason Shah18:39

      Yeah, it's definitely a combination, but I would say if I had to pick, Amazon, even though I was only there for about a year after the acquisition. I- I say that because of this blend between product and business thinking that is especially present there. And so, you know, people say Google is an engineering culture, people w- said Facebook is a product culture, Airbnb or Pinterest may... sometimes a design culture or things like this. And I think that Amazon was a place where 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 liked that because as a startup founder doing product in a bigger company, it gave me the chance to exercise a lot of those skills. And it's very similar, actually, to how I feel at Alchemy now, where I remember my first month there was like people ask me, "How's it going?" I'm like, "I feel like an athlete. I feel alive again." I can do 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. And it wasn't as siloed as sometimes a product role can be. So I- 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, "How does the same company kind of win in retail, win with AWS, go create studios?" And I think the Amazon culture ultimately, more than anything else, around ownership, being vocally self-critical, is right a lot, (laughs) is one of the leadership principles. All these things combined, I think, created a really unique culture. So, I would say Amazon's had the biggest impact on me. And- 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 view on product

6. 20:25 – 23:55

   A look into Amazon’s process on working backward

   1. JSJason Shah20:25

      and leadership.

   2. LRLenny Rachitsky20:26

      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? Like, is that something you'd encourage PMs to try to do?

   3. JSJason Shah20:37

      In general. Like, I certainly had a- a positive experience, but I think that, as you know, and as I'm sure you've advised countless people, it's- it's so context dependent. Is it... Are you learning the zero to one? Are you learning the one to scale? What's your aspiration? You know, is somebody trying to start a company eventually or are they trying to work the ranks of- of the product leadership trajectory? And so I definitely enjoyed it a lot. And I think, to your point, there's often a nonlinear sort of correlation between factors that we traditionally think are linked, right? So, my time there was one of the shortest, but my learnings were some of the greatest because I was really intentional and maybe because of the sort of moment in time and- and what I wanted to get out of it. The same way, for what it's worth, while we're talking about this disconnect, when I went to Yammer, I also interviewed with kind of... This was the era of, like, TaskRabbit. I talked to Square. And I remember people always say, "Well, what stage do you want to join? Seed, Series A, Series B?" And the crazy thing is that Yammer was... it was already past 100 people, it grew to 500 by the time of the acquisition, and it felt almost like... The culture was so tight-knit it felt like a seed stage (laughs) company at some points, even though eventually it kind of felt like a... Well, once it was acquired from Microsoft, we'll- we'll just say (laughs) it didn't feel like 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.

   4. LRLenny Rachitsky22:01

      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?

   5. JSJason Shah22:14

      Yeah, definitely. I mean, I think one that Amazon is well known for is the working backwards process. And for those that don't know, the idea is you try to define effectively an ideal end state, which, funny enough, is very similar to some of what we both experienced at Airbnb and- and took away. And usually the mechanism for doing this is what's called a PRFAQ, and that's a press release and frequently asked questions. And it forces a certain degree of clarity to have to actually write a press release about the product that you're gonna eventually launch. You... E- every employee goes through actually, like, a business writing class after they start at Amazon. They give you a little card with five tips that you're supposed to keep on your desk about concision and specificity in the words you use. For example, you should never write the word "great" in an Amazon press release. You should write, "user-friendly in XYZ way and will save customers time, 20 minutes each day through this." It's- it's intended to be very concrete in a way that avoids some of the fluffiness that... Frankly, it's funny, (laughs) 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 now. (laughs) And so, I think the working backwards process of establishing the long-term goal using a mechanism like a press release where... and- and the FAQs where every word matters. 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- or raise, you know, the elephant in the room, or dogs not barking, as Amazon likes to call it often. So, that was a really helpful process that felt very true to me as- as a way I like to live my life as well, and then also very applicable.

7. 23:55 – 28:17

   How to communicate clearly

   1. JSJason Shah23:55

   2. LRLenny Rachitsky23:55

      The tidbit about not using the word "great" is so interesting. Is there anything else there that you could share about just... Basically just, like, how to write effectively and communicate and launch? Is there any other tidbits along those lines?

   3. JSJason Shah24:07

      Yeah, that's a good question. Um, in addition to not using (laughs) 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, y- you know, more than adjectives.... strict concision, you know. I would go over these documents like countless times and, uh, there's a phrase. I can't remember if it's either Mark Twain or, 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. Fewer words means every word is, you know, 10 pounds in weight instead of one, and that means that the decisions you're making, the trade-offs are far more intentional. And in the case of great, if you say something is great because we're gonna deliver something in two hours versus Amazon's great because the selection is very wide, the implications on strategy are completely different. And so that's one of the benefits of being very specific and very concrete in language.

   4. LRLenny Rachitsky25:11

      I didn't intend to go too deep into this topic, but it's- 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, uh, you sit there and you actually, like, write out a press release that would go out when you launch this thing. Is there- there's, like, a template used? Is there anything you could share for folks that are wanting to try this out and/or point them to a resource that will help them down this road?

   5. JSJason Shah25:35

      Yeah, definitely. That's a great question. So there definitely is a template, and so it's a combination of 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 simulate what it's gonna be like. With respect to a template, uh, 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. Then usually you would describe the problem in one paragraph and in very clear language. Again, all of 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 many companies like to say or emulate, but I think it really kind of may not be true if you evaluate the mechanisms they- they use. For example, product specs that either don't have customer data or don't have quotes from customers, things like this. And so there's a customer quote, and you have to literally put yourself, you know, into the shoes of, let's say, you were launching Prime, you know. Put yourself in the shoes of, you know, Lenny from San Francisco. What exactly is he gonna say when he has access to this? And how is it different than his life today and what are the words that he's gonna use?

   6. LRLenny Rachitsky26:52

      You can't use great.

   7. JSJason Shah26:52

      You can't use gr- I mean, if great is one of your favorite words, maybe you could stretch it, but I would- I think if-

   8. LRLenny Rachitsky26:57

      Mm-hmm.

   9. JSJason Shah26:57

      ... you were in a room with your, your peers at Amazon, they might, you know, put some red pen through any greats that are used there.

   10. LRLenny Rachitsky27:03

       (laughs)

   11. JSJason Shah27:03

       So I- 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 and being a little sort of intellectually lazy where I'm like, "Yeah, I would like Prime, so let me write the quote with what I would like." But maybe I'm only, you know, a, a small segment within our total customer addressable market, right? So anyhow, there's a customer quote, then there's one leadership quote. Similarly that this achieves a complementary goal of, like, how does this fit into our strategy in a, in a way that you would express to the public, but is still true what the internal sensitivities and mechanisms would be? 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. And it- it, again, forces clarity of thought with respect to not only the rollout plan, 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- as a structure.

   12. LRLenny Rachitsky28:05

       Can you just summarize those again real quick?

   13. JSJason Shah28:07

       For sure. So the structure of the PR/FAQ docs was generally an introduction where you announce the product, problem, solution, customer quote, leadership quote, and a call to action.

8. 28:17 – 32:46

   Working backward from excitement

   1. LRLenny Rachitsky28:17

      So interesting how similar that is to, like, a one-pager potentially. The other thought I had while we were 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- both effective in different ways.

   2. JSJason Shah28:37

      I think people tend to, when they hear that both companies have some sort of working backwards process or thought, let's say, working backwards on one hand and then 11-star experience on the other, listening to how you describe it, Alin, I want to almost frame it as working backwards from sort of, like, a moment in time or launch, like you said, with Amazon, versus working backwards from a quality standard in some sense of an 11-star experience.

   3. LRLenny Rachitsky28:59

      Going in a slightly different direction, one of the- one of the things I wanted to chat about is you've 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?

   4. JSJason Shah29:18

      Yeah. That's a great question, and to briefly recap, right? I've gotten to see somebody like David Sacks, who had been the CEO of PayPal and then the founder of Yammer and gone on to do many more things since then. I've gotten to see sort of Jeff Bezos at a distance. I was never that close to him, obviously, and never got to work with him, but got to observe his impact on the organization. Obviously, I've gotten to witness Brian Chesky and his leadership 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. And I wouldn't count myself, but I've also seen myself as a bad leader in the startups that I've ran and learned from that.

   5. LRLenny Rachitsky29:56

      (laughs)

   6. JSJason Shah29:56

      And so I- I think, uh, you know, I think it's a really important thing to reflect on, and I think for me, there are three things that have stood out the most. I think, number one, nothing is above them. I've seen, you know, whether it's Brian caring about the- the full-bleed image on the homepage, whether it's Jeff Bezos who famously, you know, would receive customer emails, read many of them.... forward them and he's famous for question mark emails (laughs) where, for his time's sake, he would just forward an email to a leader with a question mark and you would just have to figure it out and then report back in (laughs) 24 hours with the resolution thereof. But nothing is above them, right? And, and a lot of founders or a lot of CEOs or even CPOs and leaders think you get to a certain point and then, "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 at one's job. And then the other two things would be, I think they're in the details. So it's less about being above something, but this is kind of... Amazon's famous for auditing the details, for example, and leaders are, you know, for example, if and when we're gonna launch Prime, order a bunch of (laughs) Prime things and see w- see what happens and, and really test things out. And write up a long feedback email on, you know, a Saturday or something like that and make sure that things are moving forward. So I think, you know, in my opinion, some of the best leaders... David Sacks would do this too. He, he actually ran the product reviews. It was the CEO of the company doing product reviews, not some kind of middle tier of, uh, director of product who was just running them. They were, of course, involved and there were things to delegate and activate around, but, um, Sacks was in all of those details and, and ran those product reviews himself, and would talk to the product managers directly. And I think that was really impactful and it also, I think, from an accountability and culture perspective, when you're a PM and you talk to the CEO, and you feel like you're presenting something at product review, it's totally different and it creates a certain amount of responsibility and quality, frankly, that I think is really important. A- and it's a way to coach, obviously, as well for those leaders to really make a mark on the organization. And then lastly, I think they adapt, right? I think that 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 be- based on past experience or based on some sort of philosophy that they've developed over time that they feel committed to, in some way. And I think, coming back to some of these examples of, you know, watching Brian lead through COVID or watching Joe and Nikhil 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 a- and adapt to the unique opportunities that are in front of us?" I think that's really powerful. So what I've seen is nothing is above them, they're in the details, 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

9. 32:46 – 38:26

   What makes a great leader

   1. JSJason Shah32:46

      with.

   2. LRLenny Rachitsky32:46

      Awesome. That was, 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. Like, he used to review every product launch and every screen of every new product. Like, we had to show him, "Here's what we're launching this week." And he just kinda went through and either blew it up or, (laughs) or let it pass. And then I just remember the founders, when they were designing the office-

   3. JSJason Shah33:12

      Mm.

   4. LRLenny Rachitsky33:12

      ... space, just looking at pictures of listings they wanted to... 'Cause at Airbnb, the office conference rooms were modeled after Airbnb listings. And Jim was just looking through hundreds of listings that the team brought him and he just, like, picked the ones that he was, wanted to, to turn into conference rooms. And also, obviously, Steve Jobs. Like, this is a, a really interesting through line of great leaders, is just this huge attention to detail, and, and there's probably something about once they let go of that, things start to kind of diminish. Is that what you find?

   5. JSJason Shah33:39

      Yeah, that's such a great point. And, you know, you mentioned the Jobs example, and there's a great book that you've probably read or in your community seen. I believe it's called Creative Selection by Ken Kocienda-

   6. LRLenny Rachitsky33:48

      Hm.

   7. JSJason Shah33:48

      ... about the early days of the iPhone.

   8. LRLenny Rachitsky33:50

      Oh.

   9. JSJason Shah33:50

      And I think it was, like, Project Purple or something like that and you're absolutely right. There were no... There wasn't... No slides, right? None of this. They brought in the prototypes for each of those reviews and things like-

   10. LRLenny Rachitsky34:00

       Mm-hmm.

   11. JSJason Shah34:00

       ... how to do typing on a tiny screen, right? And those early keyboards and how to do autocomplete, and Jobs was totally in those details from, you know, Ken's telling in this book. So I, I couldn't agree with you more and it's something that people miss, 'cause most of their exposure to leaders 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 what I think, from an ego perspective, is kind of what people want it to be about. They want it 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. One other thing I just wanted to briefly touch on, to your point on how they're connected, it's a really good point, and at the surface, it almost seems like they could potentially be the same thing. One thing worth calling out though, I think, is the idea of something not being above somebody, I think is, um... Or, or a person not being above things. I think the biggest thing I take away from that is humility, right? Is that nothing is not my job, right? Anything, you know, could be picking up paper off the floor that's... And putting it in the trash or it could be, you know, reviewing a product spec, whatever it is. And then being in the details, in my opinion, is about craft, right? And really understanding things at a, at a low level, such that you're able to reason about it and make good decisions, like Brian with the homepage, or Bezos, in some cases, with customer processes that he got in the weeds on. I think the two together, humility and being excellent at craft, I think is a very potent combination, especially when you throw in the last thing of being able to adapt to any situation.

   12. LRLenny Rachitsky35:29

       That's really interesting. What it also makes me think about is the reason things are less good often if there isn't a person at, at the top that's being very detail-oriented, and I find this with the newsletter and, and this podcast and other stuff, is no one's gonna care as much about it. No one's gonna be like, "Oh my God, I really need to get this right 'cause so much... 'Cause 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 a singular opinion or a singular person. A lot of the best startups are just, like, someone's vision. It's like, "Here. This is what we, we're gonna do." And then the, the more it becomes a community-driven thing, the less often it ends up being successful. (instrumental music plays) This episode is brought to you by Maven. I've been an investor, an advisor, and a customer of Maven from day one. I even taught my product management course through Maven. Maven is a cohort-based learning platform where you learn alongside peers with a direct connection to your instructor.Maven's got a ton of courses for product managers, founders and executives to help them level up in all kinds of ways. Over 10,000 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, Arielle Jackson on startup branding, Emily Kramer on B2B marketing, plus Annie Duke on decision-making, ??? on behavioral design, and how to break into product management with Marilee Mika. Check out all of my favorite courses and learn more at maven.com/lenny.

   13. JSJason Shah37:19

       I feel like you're totally right, especially ... I mean, this is the natural progression, but it doesn't have to be that way, right? And I think 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 trying to drive results. But as opposed to a sense of accountability, if you drove a sense of responsibility, if people felt like, "This is, this is my company too. This is my product. This is my office floor. I don't want trash on the floor. I'm gonna pick it up and throw it there," even if we have somebody whose job it supposedly is to clean that up, it's like, "I take pride of ownership in this and I'm, I'm connected to it." And I think that makes all the difference in terms of... You know, as, 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 the company. I see it at Alchemy all the time. You'll see an engineer hop in and fix something at 3:00 AM because they feel committed to the code base, and it's not a thousand-person engineering organization where my only job is to make the iOS app, you know, 2% more effective at engaging

10. 38:26 – 46:19

    How to influence a CEO or founder’s direction

    1. JSJason Shah38:26

       users.

    2. LRLenny Rachitsky38:27

       So you touched on kind of the skill of pushing back on, on a founder or CEO. And I, 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.

    3. JSJason Shah38:40

       I mean, I think this is one of the... I actually think it's one of the most misunderstood terms in a sense, because I think language, like we were talking about earlier, is so important, and yet what you call something ends up defining, I think, 90% of what people understand about a concept, right? And so pushback is (laughs) , you know, it, I couldn't imagine a word more viscerally that makes you feel like you're sort of physically going against what somebody else wants, and it gears people into a mindset of then, "Well, how should I push back?" It starts from a place of, "I need to disagree. I need to say no." It's a very negative mindset purely based on the, the word that has come to label a behavior that alternatively could be about, "How do I shift the direction on something?" Or, "How do I help the business actually succeed when I disagree with somebody about something?" And that's a very different mindset. And so the two things that I've seen be most successful 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 coming back to Airbnb, I remember Airbnb had bought a company, Luxury Retreats. There was a goal to integrate that business and that product into the full Airbnb suite, and there was a lot of potential with that. But I remember that there was part of the product experience that was oriented around chatting with somebody, um, and the idea that the business had had a very large team of, of wonderful people who helped you as concierges basically for your trip. And so this was a team that I, I was on that, to be honest, had fairly low morale. It's always difficult to integrate, you know, an acquisition with a company, especially when we were based in different places, et cetera. 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, and nobody could successfully shift the direction. And as a result, it was just this sort of... I- it was a mess as a result, and there was l- very low morale because everybody... We 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. 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 experience. And so when we took a step back, 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 a, a efficient, fast, positive experience with that trip designer and move on. 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, really smooth, slick experience for our customers. How do we do that? What's a trip designer, a new concept that is actually gonna elevate things? We're not telling you we want to pare back scope. We're not saying we want to settle for less. We're actually just not only gonna call it something different, but also envision a simpler experience which is more elegant, it's more on brand with luxury." Boom. All of a sudden, (snaps fingers) the, everybody gets what they want. They get a better customer experience, less scope. 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. So I saw that to be really effective, and I think that that's something I try to bring into, into my career. I got a, I have a couple other examples if it's useful, but that was a big one that I learned from at Airbnb.

    4. LRLenny Rachitsky42:16

       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, 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"?

    5. JSJason Shah42:30

       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, 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, but I really disagree with this strategy and I'm gonna be dug in my heels and not disagree and commit now." So in this case, I think you're totally right. It like- if it was just window dressing of, you know, founders are too smart, especially at all these companies we've talked about to be fooled with a simple renaming of something. But I think the combination of a bigger idea, more exciting idea that was at the heart of what we were all going after together, combined with a simple way of communicating it, 'cause I've also seen 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.

    6. LRLenny Rachitsky43:28

       Awesome. I'd love to hear another example.

    7. JSJason Shah43:30

       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, you know, we've created a, you know, there's traditionally growth product, growth marketing. We've created a new area around growth operations, which I'd be happy to talk about if we want to get into it. But it- it's a really interest- interesting area. And he- we were going back and forth on like, should we hire for this role? It's not even a real thing. Maybe, you know, we've looked at some candidates, we're not so sure about them. And when I realized with our founders who are incredibly smart, very talented, have built the company over so many years now, they wanna 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 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? Oh, we want to grow faster? Awesome. This is the way to do it, and that's how we're gonna actually become the generational company we want to be." Again, a reframing in this case around, yeah, we might disagree or squabble about certain things at a detail level, but I understand what we all came here to do and let's focus on that and how this is a part of that, versus just focusing on maybe the- the means to an end versus the end itself. And the end always brings a lot of clarity in my experience.

    8. LRLenny Rachitsky44:49

       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 a 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, Drip designer, like that sounds like something Brian would love."

    9. JSJason Shah45:10

       (laughs)

    10. LRLenny Rachitsky45:10

        And then in the second example, "Yeah, we're gonna win. Here's how we win." So that's a really interesting takeaway there.

    11. JSJason Shah45:15

        I mean, I think we all forget that we're all just humans, right? And at the end of the day, we all are busy, et cetera. It reminds me a lot of sales, right? Like, I was very unsuccessful when I was trying to do outbound sales in the early days of my last startup, Due.com, 'cause I didn't understand this. I- 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, you know, a CRO or a head of people that we might have been selling to cared about. I was just about features and, "Here's what we can do for you," and this and that. But I- all they cared about were one or two things, right? Maybe the CRO's growing revenue, maybe the head of people is worried about culture or scaling their talent organization, and we were nowhere near the top of that list. And so I think it's similar for CEOs and there's a huge disconnect when, say, a PM walks into a meeting with the CEO and they're talking about something that the CEO is ten miles away from thinking about. And certainly even the mindset that they're bringing to the conversation is totally different. I think Casey made a lot of great points about this in the recent podcasts as well.

    12. LRLenny Rachitsky46:16

        Sweet Casey Winters podcast plug.

    13. JSJason Shah46:18

        (laughs)

11. 46:19 – 52:27

    The career ladder vs. career map framework

    1. JSJason Shah46:19

    2. LRLenny Rachitsky46:19

       Okay, so, uh, something else that you're really good at is you don't- you don't kind of focus career-wise on working your way up the ladder and being like the- the top PM, and you seem to be really good at kind of following what's- what's interesting to you and your interests 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 something new?" What have you learned about that sort of thinking?

    3. JSJason Shah46:46

       The framework I like is ladder versus map, and I think that you can be either person at, you know, any point in your life. Sometimes there's a bit of a set mindset that somebody might have one way or another, but I like ladder versus map. Ladder is about moving up, more influence, more power, a higher title, things like this. Whereas map is, I just want to go wherever is interesting, right? I literally think of it- I think of my career very similar to travel. I want to go to Greece, I want to be hungry walking around in India sweating in 100, you know, degree weather. I want to go to Australia and kind of get locked out of my hotel and see what that's like. Like, I'm okay with discomfort because it's interesting. Sometimes, for better or worse, maybe this is a privileged- it's certainly a privileged thing to say, but I care more about living an- a really interesting life than let's say a good or comfortable life. I think it's- that's where the growth comes from, that's where the stories come from. That's, to me, the things that I'll remember the most. And so when I think about product and when I'm on my deathbed, I'm gonna care about the products I built and how they affected people. Nobody's really gonna be looking at my LinkedIn, hopefully for their sake and mine, at- at my funeral. And so that- that's what I- I think. Sorry, that's a very morbid analogy, but- but I think thinking-

    4. LRLenny Rachitsky47:58

       (laughs)

    5. JSJason Shah47:58

       ... in the future provides a lot of clarity about, what am I gonna care about a long time from now? And I think that applies to all facets of life. That's how I thought about my life partner. That's how I think about my career. That's how I think about where I want to live. San Francisco, um, you know, 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- I'm interested in the long term even if, you know, in the short term it has some challenges to it. So I- I personally believe really strongly in this kind of ladder versus map distinction, and I think a lot of people are very intentional in the micro. They think about their next job, their next title, how much salary and equity there is. And in good ways too, they think about the team that they're gonna work on next with. But they're very unintentional about the macro. 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.... in the product management field about the touchy-feely side of this, and who are you as a person, and where do you get energy from? So for me, I found that really clarifying and it makes career decisions that have seemed risky to other people seem inevitable to me.

    6. LRLenny Rachitsky49:03

       Is there like a story or an example of how you used this approach to make a decision on where you end up going, and, and/or is there something that you maybe regret or are really happy with in terms of the kind of fork in the road looking back using this way of thinking?

    7. JSJason Shah49:18

       A few concrete examples, actually. I'll keep them brief though. One is when I first moved to San Francisco, and I had mentioned I, you know, did a small sale of that education company, and I could have done a lot of more productive things with my career in the short term. I had all my peers from college who had, you know, gone off to their great jobs at Google or whatever. I said, "I just wanna... I'm just gonna 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 gonna be super interesting." And I mean, it was also very boring at times, and so I didn't, 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. (laughs) I remember one time, it's kind of a goofy story, but I was working out my dining table and I saw Ron Conway on the street, and I like... I was disheveled 'cause I was just working from my apartment and I wanted to go pitch Ron Conway on this terrible idea for a startup. And so, (laughs) I went up 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 I think make us who we are, you know. Are you the sort of person who's gonna hustle and do that, you know? When I was building that education company, I went and put flyers in people's cars at, in various high schools when I was trying to get things started. And coming back to leadership, right? That would be below most people. It's like, "What? You run a company and you're sticking flyers in people's windshield repairs? Like, what's wrong with you?" And so anyway, I think that was an example of a time where it was like, okay, if I'm on the ladder, I'm like, I gotta get the best entry-level job or whatever. Even if I'd been an entrepreneur before that, I would have thought about my structure in my career and I was more like, this is gonna be interesting. I'll figure it out. I believe in myself enough that I'll figure it out. So I did that. Yammer and leaving Yammer was similar where I could have stayed, my equity was finally worth something, and there was... A lot of, I could have learned a lot even, I'm sure, from, from the Microsoft structure, 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 gonna be, and I felt like raising money is actually gonna be really hard for me. I should take... I should... This is gonna make my life a lot easier and I can focus on product and, and so on and so forth. That was a really hard four years. Things like an M&A offer falling through the day before your wedding, or chewing glass and submitting to the Apple iStore and being a featured app and then resubmitting 'cause we wanted to fix a bug, and then actually now it crashes 90% of the time and it's 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.

    8. LRLenny Rachitsky51:48

       Yeah.

    9. JSJason Shah51:48

       Right? But using the map analogy, that's like, you know, getting lost in, in Croatia and having to find your way out, or getting lost in your hotel in Australia, or getting bitten by a dog in, in Thailand, which actually did happen to me. But, (laughs) these are interesting experiences that I think build character. So I'll pause there, but I think 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 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, and my equity would have been worth more. Whatever. 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.

12. 52:27 – 58:50

    When to follow a new opportunity vs. when to stick it out

    1. JSJason Shah52:28

    2. LRLenny Rachitsky52:28

       What's really cool about that analogy, ladder versus map, is a lot of times you think you're climbing the 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's heading to some terrible place. And what I find in my experience is any time I try something totally new and take a risk, especially following things that give me energy and I'm just like, "Let's just take a leap on this thing," I've, in my experience at least, it's always led to better 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 off the ladder and it's not gonna get you anywhere anyway. So explore other ladders. So I'm kind of picturing a Chutes and Ladders.

    3. JSJason Shah53:14

       (laughs) Totally.

    4. LRLenny Rachitsky53:15

       There's many ladders and you want to explore the different ladders across the map. How about that?

    5. JSJason Shah53:20

       I mean, I think you're totally right, and the only brief thing I would add to, 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 what we think a given career move is gonna lead to or what it's gonna be like, and we forget that, you know, a lot of career decisions are made out of maybe 10 hours cumulatively, like talking to a team and getting signal. So I think that that false precision sometimes gives us comfort in making certain decisions and holds us back from a bolder decision that might be better, but maybe the ladder 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 and, like, have the success and life and progress and so on and so forth. It's just that I think a lot of people think it's, it's totally either/or. They think that they've already figured out the precise outcome that's gonna happen, and to your point, the ladder 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.

    6. LRLenny Rachitsky54:19

       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 very serial monogamous with-

    7. JSJason Shah54:29

       (laughs)

    8. LRLenny Rachitsky54:29

       ... in terms of work. My first job, I was there nine years. Then a startup for a year and a half, and then Airbnb for seven years, and then what I'm doing now may be forever.

    9. JSJason Shah54:38

       (laughs)

    10. LRLenny Rachitsky54:38

        And so there's a lot of value to 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-... keep exploring opportunities at a place you're at versus trying something new?

    11. JSJason Shah54:54

        My hope is that there's a balance here, right? In the sense that the map shouldn't give the impression of 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 job hoppers, (laughs) which is even easier 'cause we're all on Zoom. It's a good point, and I, I really respect people like you who have stuck it out, you know, through the ups and the downs. And, uh, you know, somebody sees seven years on paper but, I mean, seven years, uh, I don't know. How many chapters of Airbnb? How many crises, moments?

    12. LRLenny Rachitsky55:26

        Felt like 300.

    13. JSJason Shah55:27

        (laughs) Yeah, there you go. So I, I think that, I think there's a balance, right? For example, like, I want to be in Web3 for more than a decade. I wanna stay at Alchemy for a very long time and help build the company. So I guess when I think of map, maybe 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, 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, I think that in, in terms of s- like, sticking it out, maybe I'm biased, uh, I think that some of the absolute sort of like gems, if you will, in Silicon Valley and tech are the teammates that are willing to stay around for four, five, six, seven years, right? And that they have institutional knowledge that nobody has. They have a positive impact on the culture 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, 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. (laughs) You're a s- a successful startup founder. You're a product leader. All these things form a map and a, uh, I think a really interesting career and life, frankly, that's pretty full with a lot of really interesting milestones and learnings and, and networks and people that you get to interact with.

    14. LRLenny Rachitsky56:47

        Yeah, to your point about how long a career is, when I thought about it recently, this is my fourth career.

    15. JSJason Shah56:53

        (laughs)

    16. LRLenny Rachitsky56:53

        First I was, uh, an engineer. Then I was a founder, then a product manager when I got to Airbnb, and now this weird thing-

    17. JSJason Shah56:59

        (laughs)

    18. LRLenny Rachitsky57:00

        ... 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 ev- Airbnb for me was not early, so maybe I'm wrong. But it feels like you wanna work at a company where people look at that on your resume and are like, "Oh, okay. This person's probably good." So I feel like there's that piece you gotta get right at some point.

    19. JSJason Shah57:21

        Yeah, I totally agree with that. For example, I think for, let's say, a new grad, right, who's thinking about a product career, and let's say on this spectrum, there is maybe like Goldman Sachs, 'cause that's what a lot of people are doing. They're like, "Yeah, I want to do product, but I also, you know, feel like I need this gold star," or whatever. And then in between is you could join, you know, a hyper growth company of some sort where 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. And on the other end of the spectrum is, you know, "I'm gonna have no job. I'm just gonna completely bounce around from my own projects or just, you know, work with a s- a new startup every two months." Personally, in that spectrum, I tend to be more towards the middle of that, where build a track record, build a network. I mean, it's crazy, even just, uh, this week, next week, I'm seeing maybe five people that I know from my Yammer days. 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. That's how I hire, I still hire people, maybe much to their chagrin. They still get LinkedIn messages from me trying to push them for the next thing. (laughs) So I, 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 kind of 30 years working up the ladder or is fixated on, "I need to be CPO," 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 a risk in

13. 58:50 – 1:03:47

    How to hire the right people

    1. JSJason Shah58:50

       their career.

    2. LRLenny Rachitsky58:50

       You touched on hiring, and this is something I, I wanted to ask you. So you're, 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.

    3. JSJason Shah59:10

       I, I appreciate that. Um, and I get a lot of value, right, out of meeting some really talented people from the collective. I think hiring, it's funny, it reminds me of a sort of pushback in a sense of like what you call it has such an impact on how people think about it. It's hiring, recruiting. But if people reframe it as like the people you are going to work with every day, (laughs) or the people who make the company what it is, it, 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? And I know a lot of people have benchmarks. I think maybe on the Google podcast talk about 30%, 40% of, of a founder's time may be spent on recruiting.

    4. LRLenny Rachitsky59:47

       Mm-hmm.

    5. JSJason Shah59:48

       Because I think deep down, everybody understands that that's incredibly valuable. I, I think that for, for me personally, I was reflecting ahead of the podcast on how I approach things now after different stages of, of hiring. And for context, for what it's worth, right? I've been at the 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 is effectively doing sourcing for you and setting up interviews and such and things like this, and there's formal calibrations and interview panels. To a place like Alchemy where it's very sort of scrappy. We need to figure out who we even wanna hire. The founders still meet with every candidate. It's a really different environment. So this is kind of the spectrum that I've seen. And I was reflecting, what do I think works the best? And I, 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 aspect to it. And what I mean by that is that, on a marketing level-... 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 that you're a known quantity before they even step in the door to interview? Are they even willing to interview based on what they know about the company? And so I think that the, the marketing aspect in it, and I mean it sort of lowercase marketing in this sense, of course, because I think a hard sell of any sort or, you know, anything that's not authentic is probably gonna fail ultimately. But it's about developing a really positive kind of brand and reputation for company, but a- also as an individual. 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 a salesperson (laughs) I am, for example, 'cause I didn't listen to people's pain points and understand the one or two things that were most important to them. And I think similarly in this context, do they wanna work, if they're an engineer, do they wanna work in a world class engineering organization? If they're a product person, are they just really excited about crypto and they wanna find a way in, and that's what ... And then, you know, a place like Alchemy is the best place for them to learn that is, you know, how to think about it. And it's not about, you know, misdirecting on or, or matching whatever they say. It's, but it's about really understanding who they are and what motivates them and what they're excited about, because I'm as concerned about the kind of post-hiring step as I am the pre-hiring and want them to work out and be happy and be effective. 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, because I think the product is, it, it's one of those rare cases where, you know, job descriptions are almost like product specs, right? They're, here's what the responsibilities are, here's what we need you to do, here's w- the qualifications we're looking for. 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 nobody thinks about it again until the person's hired and then they take it down. And I think taking a product mindset where I meet people all the time now where I don't really know exactly what role they're necessarily gonna fill, who, I'm not really sure about their, exactly their seniority. Maybe they don't have a lot of experience, but maybe they would just totally be a rockstar on our product team. And looking at, like, a product that we can mold flexibly and think of the same way if, you know, at Airbnb if we were gonna build Airbnb Plus, if we just kind of came back to, you know, the Amazon working document, 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 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 coached hosts and learned about that. So I think a product mindset when hiring 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 what I've 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 a person successful rather than just checks a box in your recruiting software as some new head count that was hired.

    6. LRLenny Rachitsky1:03:45

       One last question before we get to

14. 1:03:47 – 1:06:49

    What skill is most important for product managers

    1. LRLenny Rachitsky1:03:47

       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 you and helping PMs in general advance in their career?

    2. JSJason Shah1:03:59

       Yeah. This is a really important question like, like the others, but I think that understanding and defining what problem matters 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 or building, it can apply to what a company's mission is. And I think, I've found it really effective because it, it affects pretty much everything. It affects, you know, what we're gonna build. It affects, is the team motivated by what we're doing? So specifically, for example, at a place like Alchemy where yeah, we're a developer platform, but 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 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 vacuum. It's, is the problem developer experience and we wanna make things easier to develop? Is the problem that an NFT marketplace, a, a whole suite of them are trying to grow and need more support from us? And not understanding these problems clearly, and it goes back to my first company. It was an education company and the problem with that, low income students didn't have access to the same resources to get into college as other students. And that guided everything. That guided the pricing model, which was basically free for a long time, and then we monetized on sponsorships from colleges, right? 'Cause the problem mattered. Whereas the problem to solve was there's not a, a different problem. It's, there's just no good 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 that's what I've found to be the most useful, and I can give other examples if it's helpful, but understanding what problem we're actually trying to solve and really getting crystal clear about it, I think has been incredibly useful to me and energizing as well.

    3. LRLenny Rachitsky1:05:48

       That's such a good reminder. Even though it's such a cliché of product managers being, "Well, what problem are we trying to solve here?" Like, people hate that, but Michael Pollan, I mentioned this on a different podcast too, he, he makes this point that when you're, like, when you do drugs sometimes you have these epiphanies that you come out and you're like, "Love is all you need, man."

    4. JSJason Shah1:06:06

       (laughs)

    5. LRLenny Rachitsky1:06:06

       It's like, like okay, yep. (laughs) But it feels so right, and like, you really feel it. And the reason that it's such a cliché is 'cause people have s- found it to be so true for so long that it's, like, annoying now, but it, 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 make fun of PMs for that, but that's because it's so damn important.

    6. JSJason Shah1:06:28

       Just a, a brief kind of additional, uh, wh- what you're showed there, I, I mean, I completely agree. I think it, it's very true in life, right? It's like, well, what matters? And it's like, well, your health, your family, your pur- sense of purpose. And it's like nobody's unfamiliar with 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 product is ultimately sort of all about too.

15. 1:06:49 – 1:10:13

    Lightning round!

    1. LRLenny Rachitsky1:06:49

       Awesome. Are you ready for our lightning round where I'm just gonna ask you five quick questions, tell me what comes to mind, and we'll have some fun? Does that sound good?

    2. JSJason Shah1:06:57

       That sounds great. Ready.

    3. LRLenny Rachitsky1:06:59

       Okay, cool. I think I'm gonna start adding music to these things.

    4. JSJason Shah1:07:01

       (laughs)

    5. LRLenny Rachitsky1:07:01

       I gotta figure that out. For now, no music. Okay. What book, what book do you recommend most to other PMs?

    6. JSJason Shah1:07:07

       The Hard Thing About Hard Things.

    7. LRLenny Rachitsky1:07:09

       Mm.Can you add why?

    8. JSJason Shah1:07:11

       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.

    9. LRLenny Rachitsky1:07:21

       Man, this chew glass metaphor, I don't like the sound of that.

    10. JSJason Shah1:07:24

        (laughs) I saw you cringe. I was a little worried about that. (laughs)

    11. LRLenny Rachitsky1:07:26

        Oh, my God. What a great job we have here chewing glass.

    12. JSJason Shah1:07:30

        (laughs)

    13. LRLenny Rachitsky1:07:30

        Okay. Other than Alchemy, what's a company you recommend most PMs to go look for new gigs if they're looking around?

    14. JSJason Shah1:07:37

        I would suggest Polygon, Solana, or Moonpay. I know it's three, but I wanted to give some breadth in the Web3 space that might be exciting to people.

    15. LRLenny Rachitsky1:07:44

        Hmm. Great. Great choices. What's a favorite TV show or movie that you've recently watched?

    16. JSJason Shah1:07:48

        The Ken Burns Vietnam War series. I'm really into documentaries and history, and it's a really kind of compelling version of history that I've never seen before.

    17. LRLenny Rachitsky1:07:58

        Awesome. Love that. Okay, favorite interview question that you like to ask?

    18. JSJason Shah1:08:02

        What is a risk you regret not taking, why, and what did you learn about yourself?

    19. LRLenny Rachitsky1:08:08

        What do you look for in an answer there?

    20. JSJason Shah1:08:10

        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 gets at their psychology and how do they think about not only their career, but if they were to work with me, how would they approach problem-solving and taking bets on a business?

    21. LRLenny Rachitsky1:08:33

        Awesome. Okay, final question, what's your least favorite vegetable?

    22. JSJason Shah1:08:36

        Broccoli. I just removed some from a pizza-

    23. LRLenny Rachitsky1:08:39

        (gasps)

    24. JSJason Shah1:08:39

        ... last night that I really didn't want to eat.

    25. LRLenny Rachitsky1:08:41

        Wow. Oh, wow. Okay. Even, like, steamed, uh, cooked, all the things?

    26. JSJason Shah1:08:45

        There are no circumstances under which I'm excited about broccoli.

    27. LRLenny Rachitsky1:08:49

        Oh, man. You got to eat th- those veggies.

    28. JSJason Shah1:08:51

        I know. I'm working on it.

    29. LRLenny Rachitsky1:08:52

        Okay. Jason, this was amazing, lived up to what I was hoping our second episode would be.

    30. JSJason Shah1:08:57

        (laughs)

Episode duration: 1:10:13