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Jason Shah (Airbnb, Amazon, Microsoft, Alchemy)18 September 2022

Building a meaningful career

7Frameworks
15Insights

Episode overview

Lenny Rachitsky speaks with Jason Shah about product management in Web3, maintaining morale through volatile cycles, and the lessons Shah drew from Alchemy, Airbnb, Amazon, Microsoft, and his startups. Shah explains Amazon’s working-backwards process, argues that effective leaders combine humility, detailed craft, and adaptability, and reframes organizational pushback as alignment around shared goals. They also discuss his “ladder versus map” approach to building a meaningful career, a marketing-sales-product model for hiring, and the importance of defining the problem that truly matters.

Key ideas

  • Progress, rather than speeches or extrinsic incentives, is the strongest foundation for sustaining team morale through downturns.
  • As Web3 products mature and competition increases, product managers become more valuable for strategy, prioritization, execution, and collaboration.
  • Amazon’s working-backwards process uses a concise PRFAQ to clarify the customer problem, proposed solution, strategic fit, risks, and launch action.
  • Effective leaders treat no task as beneath them, remain close to operational and product details, and adapt when circumstances change.
  • Influencing founders works best by understanding their underlying goal and reframing the proposal around a shared outcome instead of adversarial pushback.
  • The “ladder versus map” framework contrasts optimizing for title and power with exploring work that is meaningful, energizing, and interesting over a long career.
  • Hiring can be treated as marketing to establish reputation, sales to understand candidate motivations, and product development to iterate the role around mutual fit.
  • A product manager’s most important skill is identifying and clearly defining which problem actually matters.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 22

  • Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter

    welcome to lenny's podcast i'm lenny

  • Jason ShahMentionsi've been with alchemy which is a blockchain infrastructure company for the last year

    today my guest is jason shaw

  • Gokul RajaramMentionsa tactic gokule shared on this podcast about one of his best tricks

    including resources for many guests on this podcast including shreyas gokul and shashir

  • Shishir MehrotraMentionsshashir marocha is the co-founder and ceo of koda before starting koda shashir led the youtube product engineering and design teams

    shashir the ceo of coda

  • Shreyas DoshiMentionsHe reflects on roughly 20 years in product work and leadership roles at Google, Twitter, and Stripe.

    including resources for many guests on this podcast including shreyas gokul and shashir

  • John CutlerMentionsI talked to John Cuddler actually and he gave me this framework that is like completely stuck in my mind

    i'm excited to chat with my friend john cutler from podcast sponsor amplitude

  • David SacksMentionsceo of paypal and then the founder of yammer

    david sachs who've been ceo of paypal and then the founder of yammer

  • Brian CheskyMentionsBrian chesky at Airbnb there was a whole article where we unpacked this moment in their product development cycle

    i've gotten to witness brian chesky and his leadership

  • Jeff BezosMentionsthe Jeff Bezos thing that like the success of today was set in motion three years ago

    i've gotten to see sort of jeff bezos at a distance

  • Joe LauMentionsAlchemy co-founder

    at alchemy our co-founders joe and nikhil are leaders that have really had an impact on me

  • Nikil ViswanathanMentionsAlchemy co-founder

    at alchemy our co-founders joe and nikhil are leaders that have really had an impact on me

  • Steve JobsMentionsSteve Jobs is just uh the bar he held for the company and for technical talent and for excellence was not uh wavering.

    and also obviously steve jobs

  • Ken KociendaCoinedAuthor of Creative Selection

    creative selection by ken cocienda about the early days of the iphone

  • Nir EyalMentionsNir is the author of two best-selling books and teaches and consults at the intersection of psychology, technology, and business.

    near at all on behavioral design

  • Annie DukeMentionsAnnie is the author of the bestselling book thinking in bets and also her more recent book quit

    annie duke on decision making

  • Emily KramerMentionsemily led and built the marketing teams at asana carda ticketfly and astro which was a startup acquired by slack

    emily kramer on b2b marketing

  • Arielle JacksonMentionsarielle jackson from first round is an amazing support system to founders and marketers at startup

    ariel jackson on startup branding

  • Jackie BavaroMentionsA big thank you to Jackie Bavaro

    jackie bavaro on product strategy

  • Marily NikaMentionsmarily teaches the most popular course on Maven on AI and product management she's currently product lead at meta

    how to break into product management with merely nika

  • Casey WintersMentionswho's had the most influence on you in your career well we mentioned him before so I gotta bring him back up Casey Winters

    sweet casey winters podcast plug

  • Ron ConwayMentionsAngel investor approached by Jason Shah in San Francisco

    i saw ron conway on the street

  • Michael PollanMentionsmichael pollan has this point that he makes that like cliches and platitudes are cliches and platitudes because we've heard them so many times

    michael pollan i mentioned this on a different podcast too

Resources · 45

  • Lenny's PodcastCoinedpodcast · Lenny Rachitsky

    welcome to lenny's podcast i'm lenny

  • CodaUsessoftware · Coda

    i actually use coda every single day

  • CodaRecommendssoftware · Coda

    make your life better and start using coda

  • AmplitudeMentionssoftware · Amplitude

    we've always thought of amplitude as being about supporting the full product loop

  • YammerUsessoftware · David Sacks

    that was actually my first formal product management role and i stayed at yammer

  • MicrosoftUsescompany · Bill Gates and Paul Allen

    i stayed through the microsoft acquisition back in 2012

  • Amazon Web ServicesMentionscompany · Amazon

    they were growing their aws offering sas products

  • AirbnbUsescompany · Brian Chesky, Joe Gebbia, and Nathan Blecharczyk

    i got bored and excited about what airbnb was doing and the mission around belonging

  • AmazonUsescompany · Jeff Bezos

    we found a better fit with amazon

  • Do.comCoinedsoftware · Jason Shah

    started another company called do.com and ran that for about four years

  • AlchemyUsesbook · Rory Sutherland

    i've been with alchemy which is a blockchain infrastructure company for the last year

  • Product Manager's Guide to Web3Coinednewsletter · Jason Shah

    it's called product manager's guide to web3

  • EthereumMentionssoftware · Vitalik Buterin

    we're seeing things like kind of record ethereum transactions happening

  • ETHCCMentionsevent

    we just had our team out at eat cc which is a big conference in paris for the ethereum community

  • SolanaMentionssoftware

    we just launched solana support

  • GeminiMentionssoftware · Google

    i saw that gemini also did the same

  • UniswapMentionssoftware

    uniswop just made a big hire out of meta

  • MetaMentionscompany

    uniswop just made a big hire out of meta

  • OpenSeaMentionscompany

    we're seeing openc i hire a lot of talent along these lines too

  • CoinbaseMentionscompany · Brian Armstrong and Fred Ehrsam

    uniswap has done more daily volume on certain days than coinbase

  • NFT.NYCMentionsevent

    i met with a lot of these at nft nyc recently

  • Bored Ape Yacht ClubMentionsproduct

    the board api club is actually building a metaverse project

  • Second LifeUsessoftware

    some of the digital games that i've used in the past of second life

  • GoogleMentionscompany · Google

    people say google is an engineering culture

  • AmazonRecommendscompany · Jeff Bezos

    i would say if i had to pick amazon

  • FacebookMentionscompany · Meta

    people said facebook is a product culture

  • Whole Foods MarketMentionscompany

    the whole foods acquisition happened when i was there

  • Amazon Working BackwardsMentionsother · Amazon

    one that amazon is well known for is the working backwards process

  • PRFAQMentionsother · Amazon

    the mechanism for doing this is what's called a prfaq and that's a press release in frequently asked questions

  • Amazon PrimeMentionsproduct · Amazon

    let's say you were launching prime

  • Creative SelectionRecommendsbook · Ken Kocienda

    there's a great book that you've probably read or in your community i believe it's called creative selection

  • iPhoneMentionsproduct · Apple

    creative selection by ken cocienda about the early days of the iphone

  • MavenUseswebsite · Maven

    i even taught my product management course through maven

  • MavenRecommendswebsite · Maven

    check out all of my favorite courses and learn more at maven.com lenny

  • Luxury RetreatsMentionscompany

    airbnb had bought a company luxury retreats

  • Casey Winters episode of Lenny's PodcastRecommendspodcast · Lenny Rachitsky

    i think casey made a lot of great points about this in the recent podcast as well

  • Apple App StoreUsessoftware · Apple

    submitting to the apple eye store and being a featured app

  • Airbnb PlusMentionsproduct · Airbnb

    at airbnb if we were gonna build airbnb plus

  • The Hard Thing About Hard ThingsRecommendsbook · Ben Horowitz

    the hard thing about hard things

  • The Vietnam WarRecommendsdocumentary · Ken Burns and Lynn Novick

    the ken burns vietnam war series

  • PolygonRecommendscompany

    i would suggest polygon salon or moon pay

  • MoonPayRecommendscompany

    i would suggest polygon salon or moon pay

  • SolanaRecommendssoftware

    i would suggest polygon salon or moon pay

  • Apple PodcastsRecommendssoftware · Apple Inc.

    you can subscribe to the show on apple podcast spotify or your favorite podcast app

  • SpotifyRecommendssoftware · Spotify

    you can subscribe to the show on apple podcast spotify or your favorite podcast app

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 3

Hot Take09:00

Why Web3 Is In Its Strongest Position Despite Crypto Winter

Recorded during the mid-2022 crypto downturn, Jason argues Web3 is actually healthier than ever. He separates the price crash and financial scandals from the underlying build activity, pointing out the term 'Web3' is barely a year old and that new technologies rarely mature in a straight line.

  • The 'Web3' label has only existed in popular lexicon for about a year, even though crypto is over a decade old
  • Price drops and financial-mismanagement scandals are separate from product progress
  • New technologies (internet, AI, QR codes) all matured through non-linear adoption cycles
  • Web3 is especially volatile because so much of it was financialized from the outset

as much as i'm a techno optimist i'm also a realist and with that being said i genuinely believe web 3 is in the strongest…

Jason Shah · 09:00
#web3#crypto#market-cycles
Hot Take17:00

How Web3 Products Got Huge Without the PM Playbook

Jason's biggest surprise in Web3 is how large products have scaled without traditional product managers or the last 20 years of internet product playbooks. He cites Uniswap out-trading Coinbase on some days with a fraction of the headcount.

  • Uniswap has done more daily volume than Coinbase on certain days with ~100 people vs 5,000+
  • NFT communities like Bored Ape are building metaverse projects that rival older digital games
  • Products can travel far without traditional product structure or resources
  • Jason still believes PMs add strong value, but the growth without them is striking

uniswap has done more daily volume on certain days than coinbase and your swap is about 100 people versus five thousand plus at coinbase right

Jason Shah · 17:00

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…

Jason Shah · 17:30
#web3#product-management#scaling
Hot Take46:30

Ladder vs Map: A Different Way to Think About Your Career

Jason offers a mental model for career choices: the 'ladder' person chases title, power, and salary, while the 'map' person goes wherever is most interesting. He compares his career to travel and says he'd rather live an interesting life than a comfortable one, using a deathbed test for clarity.

  • Ladder = more influence, power, higher title; Map = go wherever's interesting
  • He thinks of career like travel, embracing discomfort for the story and growth
  • The deathbed test: you'll care about the products you built, not your LinkedIn
  • People are intentional in the micro (next title, salary) but unintentional about the macro

the framework i like is ladder versus map

Jason Shah · 46:30

i care more about living in a really interesting life than let's say a good or comfortable life

Jason Shah · 47:30
#career#mental-models#decision-making

Explainer· 2

Explainer13:00

Why Web3 Teams Are Finally Hiring Product Managers

Jason updates his earlier view that early-stage Web3 needs fewer PMs. As products mature and markets get competitive, he's seeing serious PM hiring across seniority levels from firms like Uniswap, Gemini, and OpenSea, because product becomes a durable competitive advantage once token hype fades.

  • Teams are hiring product leaders at every level: PM, senior PM, director, VP, CPO
  • Uniswap hired from Meta; Gemini and OpenSea are hiring PM talent too
  • Product maturity and complexity make the PM role far more useful over time
  • A moving token can drive early adoption, but 'first principles' reassert themselves

i actually am seeing things change a lot and you know one thing in web3 if one learns nothing is the ability to admit when…

Jason Shah · 13:00
#web3#product-management#hiring
Explainer1:00:30

Treat Hiring Like a Business: Marketing, Sales, and Product

Jason maps hiring onto three business functions. Marketing is your company and personal brand before a candidate walks in; sales is understanding what actually motivates them; and product is treating the role itself as something iterative and moldable, rather than a static job description posted once and forgotten.

  • Marketing: what candidates already infer about your company and whether they'll even interview
  • Sales: understand the one or two things a candidate really cares about, not a hard sell
  • Product: job descriptions are like product specs but are never iterated after posting
  • Mold roles flexibly around great people rather than just filling a headcount box

i like to think of it in very similar motions to a business where i think there is a marketing aspect to it there's a…

Jason Shah · 1:00:30

job descriptions are almost like product specs right

Jason Shah · 1:02:00
#hiring#recruiting#product-management

Story· 2

Story18:30

Why One Year at Amazon Shaped Jason More Than Anywhere Else

Despite only being at Amazon for about a year post-acquisition, Jason says it left the biggest mark on how he does product because you can't divorce product from business there. He credits leadership principles like ownership and being vocally self-critical, and notes his shortest tenure produced some of his greatest learnings.

  • At Amazon you can't be a PM without thinking about revenue, growth, and go-to-market
  • Cultures differ: Google (engineering), Facebook (product), Airbnb/Pinterest (design), Amazon (product + business)
  • Ownership and being 'vocally self-critical' are leadership principles that stuck with him
  • Non-linear correlation: his shortest stint delivered his greatest learnings because he was intentional

i would say if i had to pick amazon even though i was only there for about a year after the acquisition

Jason Shah · 18:30

my time there was one of the shortest but my learnings were some of the greatest because i was really intentional

Jason Shah · 21:00
#amazon#career#product-management
Story39:00

How Reframing 'Concierges' as 'Trip Designers' Fixed a Stalled Team

Jason retells an Airbnb story about the Luxury Retreats integration, where a chat product was ballooning with features and morale was low. A persuasive leader reframed the concierge role as 'trip designers,' aligning everyone on a simpler, more elegant experience, which cut scope and lifted the team. He argues 'pushback' is a self-defeating word.

  • The word 'pushback' primes a negative, disagreement-first mindset
  • Better to understand the shared goal and align around it than to say 'no'
  • The Luxury Retreats chat product was over-scoped with features and low morale
  • Reframing concierges as 'trip designers' aligned the team on a simpler, on-brand experience with less scope

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…

Jason Shah · 39:00

when we took a step back it was reimagined as trip designers not concierges

Jason Shah · 41:00
#airbnb#influence#reframing#product-management

Tool· 1

Tool1:07:00

The Book Jason Recommends Most to PMs

In the lightning round, Jason recommends 'The Hard Thing About Hard Things' as the book he suggests most to product managers, because it teaches them to 'chew glass' and care about outcomes the way a CEO must. He also points PMs toward Polygon, Solana, and MoonPay in Web3.

  • Top book recommendation: The Hard Thing About Hard Things
  • It teaches PMs to care about outcomes like a CEO does
  • Web3 companies worth exploring: Polygon, Solana, MoonPay
  • Favorite interview question: 'What is a risk you regret not taking, why, and what did you learn about yourself?'

i think it teaches product managers to chew glass and care about outcomes the way that a ceo has to

Jason Shah · 1:07:00
#books#recommendations#product-management

Takeaway· 7

Takeaway11:00

The Only Way to Keep Morale Up Is to Make Progress

Jason says that during downturns, extrinsic motivators like speeches or free crypto don't sustain a team. What actually keeps people motivated is visible progress, shipping, and focusing on product and customers. He ties it to Airbnb's revenue drawdown during COVID.

  • No speech or extrinsic reward reliably maintains morale
  • People get excited when they see real progress and shipping
  • Airbnb kept building through an 85-90% revenue drop by focusing on product and customers
  • Hiring people motivated for the right reasons compounds this effect

i think that the only way to maintain morale is to make progress

Jason Shah · 11:00
#leadership#morale#team-management
Takeaway22:30

Amazon's Writing Rule: Never Say 'Great,' Use Numbers

Jason shares the writing discipline Amazon drills into employees: banned vague words like 'great,' numbers over adjectives, and ruthless cutting. The point isn't saving ink, it's forcing clarity of thought so every trade-off is intentional.

  • Never write the word 'great' in an Amazon press release; be specific about the benefit
  • Use numbers more than adjectives, and apply strict concision
  • 'Kill your darlings': cut relentlessly until every word carries weight
  • Fewer words force clearer thinking, not just shorter documents

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…

Jason Shah · 22:30

there's a phrase i can't remember it's either mark twain or or another famous writer who said kill your darlings right cut cut cut

Jason Shah · 24:00
#writing#communication#amazon
Takeaway30:00

Three Things the Best Leaders Have in Common

Having observed leaders like Bezos, Chesky, and David Sacks, Jason distills great leadership into three traits: nothing is above them (humility), they're deep in the details (craft), and they adapt to new information. He illustrates with Bezos's famous question-mark emails and Sacks personally running product reviews.

  • Nothing is above them: leaders who think they're 'above' a spec or a SQL query make a mistake
  • In the details: David Sacks ran product reviews himself instead of delegating to a director
  • They adapt: the best leaders shift gears with new information rather than clinging to a playbook
  • Humility plus craft, combined with adaptability, is a potent combination

so what i've seen is nothing is above them they're in the details and they adapt to new information and new situations

Jason Shah · 32:00
#leadership#management
Takeaway37:30

Drive Responsibility, Not Just Accountability

Jason contrasts top-down accountability (performance reviews) with a genuine sense of ownership. When people feel a company or product is truly theirs, they push back, propose ideas, and fix things at 3am, because they're invested rather than merely assigned.

  • Accountability is often top-down: performance reviews and enforcement
  • Responsibility is felt ownership: 'this is my company, my product, my office floor'
  • Owners push back and propose ideas because they feel invested
  • At Alchemy, engineers fix things at 3am because they're committed to the codebase

you see an engineer hop in and fix something at 3am because they feel committed to the code base

Jason Shah · 38:00
#leadership#ownership#culture
Takeaway44:00

To Influence a Founder, Work Backwards From What They Want

Jason describes convincing skeptical founders to hire for a novel 'growth operations' role by connecting it to what they care about most: winning. Instead of defending a resume or role definition, he framed it around the end goal, which he says always brings clarity.

  • Don't make a rational argument about the role in a vacuum; connect to the founder's core drive
  • His founders care most about winning and growing faster, so he pitched the hire that way
  • Like sales, listen for the one or two things the other person actually cares about
  • Focusing on the end, not the means, brings clarity

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…

Jason Shah · 44:00

the end always brings a lot of clarity in my experience

Jason Shah · 44:30
#influence#founders#communication
Takeaway55:30

The Underrated Value of Staying Somewhere for Years

As a counterbalance to constant exploration, Jason argues some of tech's real gems are people who stay four to seven years. They accrue institutional knowledge nobody else has and stabilize culture, which is impossible amid constant turnover. He describes himself as 'serial monogamous' with work.

  • The 'map' shouldn't mean hopping through 180 companies at a month each
  • Long-tenured teammates hold institutional knowledge no one else has
  • They have a positive cultural impact that churn destroys
  • A 30-40 year career leaves room for several long, committed 5-10 year runs

some of the absolute sort of like gems if you will in silicon valley in tech are the teammates that are willing to stay around…

Jason Shah · 55:30
#career#tenure#culture
Takeaway1:04:00

The Most Important PM Skill: Defining Which Problem Matters

Asked for the single most valuable skill for advancing PMs, Jason names understanding and defining what problem actually matters. It cascades into everything: what to build, whether the team is motivated, and even the business model. He grounds it in his education startup, where the core problem shaped free pricing and a curriculum-first focus.

  • Defining the right problem affects what you build and whether the team is motivated
  • At Alchemy, 'should we build an SDK or an NFT API' resolves to 'what problem are we solving'
  • His education startup's problem (low-income access to college) drove free pricing and college-sponsorship monetization
  • It's a cliche precisely because it has proven so true for so long

understanding and defining what problem matters is the most important skill that i think i've taken away

Jason Shah · 1:04:00
#product-management#career#problem-definition