Progress Beats Pep Talks: Jason Shah on Leading Product Teams Through Web3's Ups and Downs

Shah describes himself as a techno-optimist and a realist, and says Web3 is in the strongest position it has ever been in, even in a crypto winter. The term itself has barely been in popular use for a year, while crypto has existed for over a decade. He points to more companies forming, early product-market fit, record Ethereum transactions, new Layer 2 technologies and Solana's announced phone, while acknowledging price drops and financial scandals.

Asked how a PM keeps people focused when everyone's crypto is falling, Shah says morale and the ability to keep building decide long-term success. He thinks no speech or extrinsic motivator, such as handing out free crypto, really works. People get excited when they see progress.

At Alchemy, he says, there are more developers on the platform than ever, the team recently launched Solana support, and a trip to the EthCC conference in Paris showed how many people are building. He draws a parallel with Airbnb, whose revenue dropped sharply and with no clear recovery date. What worked there was making progress, focusing on product and customers, and hiring people motivated for the right reasons.

Lenny notes that Shah's popular post on being a PM in Web3 argued there was much less need for PMs early on. Shah says he is now seeing the opposite: teams hiring product leaders and product managers who work in a more traditional way, alongside community and marketing duties. He names Uniswap's hire from Meta, Gemini and OpenSea as examples, at levels from PM to CPO.

He gives two reasons. Products have matured and grown more complex, and the market has become competitive, with many NFT marketplaces and many Layer 1 and Layer 2 chains. Earlier, a rising token could drive adoption, but that only lasts so long and then first principles return. Lenny adds that people who doubt the need for PMs usually haven't worked with a great one.

Shah says his biggest surprise was how large some products grew without the traditional PM role or playbooks. Uniswap has at times done more daily volume than Coinbase with about a hundred people, versus more than 5,000 at Coinbase. He also notes that Bored Ape Yacht Club is building a metaverse project that looks better than games he has used before.

Of his stops at Yammer, Microsoft, Amazon and Airbnb, Shah says Amazon shaped him most, despite only about a year there after an acqui-hire. He liked how inseparable business and product thinking were: you could not be a PM without thinking about revenue growth and go-to-market. The culture of ownership, and the leadership principle of being vocally self-critical, left a big mark, and he says it resembles how he feels at Alchemy today.

He singles out the working-backwards process, in which a team writes a press release and FAQ for the product it will eventually launch. Amazon employees take a business writing class and get a card of tips on concision and specificity. You should never write the word "great", only concrete claims such as time saved per day. Shah recommends numbers over adjectives and relentless cutting, because fewer words make each one carry more weight.

The template he recalls starts with an announcement, a one-paragraph problem, a brief solution, a customer quote, a leadership quote, and a concrete call to action. The customer quote forces you to imagine a real customer's words rather than assuming you are the customer. The call to action forces a rollout plan. The FAQ has external and internal sections, the latter meant to de-risk launch and raise the elephant in the room.

Lenny contrasts this with Airbnb's idea of working back from an 11-star experience. Shah frames Amazon's version as working backward from a moment in time, a launch, and Airbnb's as working backward from a quality standard.

Shah draws on observing David Sacks at Yammer, Jeff Bezos from a distance, Brian Chesky at Airbnb and the co-founders at Alchemy, and also on his own mistakes as a leader. His first trait is that nothing is above them. Chesky cared about the full-bleed image on the homepage, and Bezos read customer emails and forwarded them with a question mark for a leader to resolve within 24 hours. Leaders who think they are above a product spec or a SQL query lose respect and effectiveness.

The second trait is that they are in the details. Amazon audits details, and leaders ordered Prime products themselves and wrote feedback on a Saturday. Sacks personally ran product reviews instead of delegating them to a director. Shah says this brings accountability and lets leaders coach. The third trait is adapting, which he saw in Chesky through COVID and in Alchemy's founders shifting gears in the crypto winter.

Lenny recalls Chesky reviewing every launch and screen, and Steve Jobs's famed attention to detail. Shah mentions the book Creative Selection, in which Jobs reviews iPhone prototypes rather than slides. He says the first two traits combine humility, meaning nothing is not my job, with craft. He also wants accountability to come from a sense of ownership rather than top-down performance reviews, such as an Alchemy engineer fixing something at 3 a.m. because he feels committed to the code base.

Shah says "pushback" is one of the most misunderstood terms, because the word itself pushes people into a negative mindset of disagreeing and saying no. The alternative is to ask how to shift direction or help the business succeed. His first tactic is to understand what the other person's goal or issue is, and then align the two.

His main example is Airbnb's acquisition of Luxury Retreats. The team was building a complicated chat product for concierges, with low morale and ballooning scope. A leader effective with senior leadership reframed it around a magical experience: concierges became trip designers, with an elegant, simple chat experience. Scope shrank, the customer experience improved, and, as Shah puts it, everyone got what they wanted.

Asked whether it was just a rename, Shah says it was a bigger idea combined with simple communication, because founders are too smart to be fooled by window dressing. His second example is Alchemy, where a debate about hiring for a new growth operations role was settled by appealing to the founders' drive to win and grow faster. Lenny sums it up as working backwards from what the CEO is excited about, and Shah likens it to his failed early sales efforts, where he talked features instead of the buyer's one or two concerns.

Shah offers a framework he likes: ladder versus map. A ladder is about moving up in influence, power and title, while a map is about going wherever is interesting, like traveling. He says he cares more about an interesting life than a comfortable one, and thinks about what he will care about on his deathbed, namely the products he built and how they affected people. People are intentional about their next job or salary, he says, but unintentional about the macro picture.

His examples include moving to San Francisco without a job after selling his education company, working at his dining table and building five or six products. He also left Yammer even though his equity was finally worth something, and followed it with a hard four years at his next startup. He mentions an acquisition offer falling through the day before his wedding and an app that crashed after a resubmission. He admits to some regrets, but says the experiences taught him things he otherwise wouldn't learn.

Lenny adds that ladders fall over and that exploring other ladders has always led to better work. Shah says we have false precision about where a career move leads, often based on perhaps ten hours of talking with a team. Both warn against constant job hopping: Shah wants more than a decade in Web3, and he says the real gems are teammates who stay four to seven years and hold institutional knowledge. For early careers he prefers a middle path of building a track record and a network, citing the Yammer colleagues who taught him A/B testing and became his first angel investors.

Shah says that, like pushback, the word "hiring" frames how people think. If you see it as choosing the people you work with every day, it is obviously a top priority, and he mentions a benchmark of 30 to 40 percent of a founder's time. He has recruited at every stage, from convincing engineers to join a zero-person startup to Amazon's large recruiting organization to Alchemy's scrappier process where founders meet every candidate.

He breaks effective hiring into marketing, sales and product. Marketing means being a known quantity with an authentic reputation for the company and yourself, so candidates have heard good things before they interview. The sales part means listening to what motivates each person, since he cares about the post-hire stage as much as the pre-hire one. The product part means treating a job description like an iterative product spec rather than something posted once and forgotten.

He often meets people without knowing exactly what role or seniority fits, and sees that as a chance to mold a role around them. He compares this to how Airbnb built and iterated on real homes for Airbnb Plus, changing pillows, entrances and scents, instead of just writing a document. The result, he says, is a role that makes the person successful rather than a box ticked in recruiting software.

Asked which skill most helps PMs advance, Shah says it is understanding and defining what problem matters. It shapes what the team builds and whether people are motivated. At Alchemy, whether to build an SDK or an NFT API depends on whether the problem is developer experience or the needs of growing NFT marketplaces.

He points back to his first company, an education business built because low-income students lacked the resources other students had for college admission. That problem drove the pricing model, which was free for a long time and funded by college sponsorships. A different problem, no good readiness program, would have meant focusing on pedagogy and curriculum. Lenny agrees that "what problem are we solving?" is a cliche because it is so true.

In the lightning round, Shah recommends *The Hard Thing About Hard Things*, because it teaches PMs to care about outcomes like a CEO. For PMs looking for a new role in Web3, he points to Polygon and MoonPay, among others. His favorite interview question asks what risk a candidate regrets not taking and what they learned. He closes by pointing listeners to alchemy.com and his handle @0xShah.