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Lenny's 🏦 Vault

107 Leadership Perspectives shared on Lenny's Podcast

AI Founders Need Monetization From Day One
By Madhavan Ramanujam - Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam

Founders, especially in AI, must consider pricing early so business viability co-evolves with product development.

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Madhavan Ramanujam
Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam

AI Founders Need Monetization From Day One

Founders, especially in AI, must consider pricing early so business viability co-evolves with product development.

OM
Owen McCabe
How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO)

Founders Should Hire Young CEOs for AI Transformation

Founders unwilling to match the intense AI startup pace should hire a younger CEO and move into a chairperson role, Owen advises.

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Garrett Lord
Inside the expert network training every frontier AI model | Garrett Lord

Seizing Once-in-Lifetime AI Opportunity

He tells the team it’s “time to amp it up” and seize the once-in-a-lifetime AI opportunity, channelling passion and stamina into execution.

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Annie Duke
This will make you a better decision maker | Annie Duke (Thinking In Bets, former pro poker player)

Kahneman's Humility and Open-Mindedness

Annie highlights Kahneman’s habit of saying "I don’t know" and eagerly changing his mind as a model for leaders.

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Matt Lemay
The one question that saves product careers | Matt LeMay

PMs Present Options Not Yes Or No

Great PMs present clear options with trade-offs instead of simply agreeing or refusing requests.

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Peter Dang
From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products

Growth Teams Force Measurement Rigor

Peter immediately forms a growth team because their data-driven questions expose logging gaps and instil rigorous measurement across the org.

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Benjamin Mann
Anthropic co-founder: AGI predictions, leaving OpenAI, what keeps him up at night | Ben Mann

Transparency Builds Policymaker Trust

Publishing model misbehaviours is a deliberate trust-building approach with policymakers despite possible bad press.

HL
Howie Liu
How we restructured Airtable's entire org for AI | Howie Liu (co-founder and CEO)

Weekly AI Sprint Check-ins Drive Urgency

He set a standing weekly sprint check-in on AI execution to keep half the org operating with urgency like an AI-native startup.

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Matt LeMay
The one question that saves product careers | Matt LeMay

Magic Lies in How People Work Together

Matt argues the real magic in music and product comes from diverse people building something greater than their individual parts, a value that will grow...

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Brian Balfour
Why ChatGPT will be the next big growth channel (and how to capitalize on it) | Brian Balfour

Exiting AI Resistors Preserves Company Culture

Brian explains why leaders must be willing to exit employees who resist AI to preserve a cohesive high-density culture.

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John Zorotsky
Rapidly test and validate any startup idea with the 2-day Foundation Sprint

Pricing Rarely Works as Durable Differentiator

John argues pricing is seldom the strongest or most durable differentiator, especially against resource-rich rivals, unless AI unlocks step-change cost drops.

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Chip Conley
Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)

Older Employees Connect Dots While Younger Employees Focus

Instead of classes, new managers shadow seasoned leaders during real work to learn reviews and meeting facilitation.

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David Plasik
Naming expert shares process for creating billion-dollar brands: Vercel, Azure, Windsurf, Sonos

Working With Teams That Play To Win

David works only with teams that aspire to win rather than merely avoid loss and urges internal champions to lead decisively despite conservative bosses.

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Asha Sharma
How 80,000 companies build with AI: Products as organisms and the death of org charts | Asha Sharma

Maximizing Option Value Over Minimizing Regret

Asha shifted from a minimise-regret lens to maximising option value, investing in skills, health, and relationships that compound into more future adventures.

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Nick Turley
Inside ChatGPT: The fastest growing product in history | Nick Turley (OpenAI)

Follow Curiosity and Smart People, Not Money

Nick advises prioritising work that excites your curiosity and surrounding yourself with energising people rather than chasing money.

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Dan Shipper
The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code. | Dan Shipper (Every)

AI Rewards Generalists Over Specialists

Dan argues that AI will let small teams stay small and reward versatile generalists over narrow specialists.

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Howie Liu
How we restructured Airtable's entire org for AI | Howie Liu (co-founder and CEO)

PMs Need Cross-Functional Skills in AI Era

Howie tells PMs and designers to proactively pick up engineering and AI skills, stressing brains are malleable and resources abundant.

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Matt Lemay
The one question that saves product careers | Matt LeMay

Present Options with a Recommendation

Alongside multiple options you must state a recommendation to avoid endless hole-poking and build momentum.

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Ben Horowitz
$46B of hard truths: Why founders fail and why you need to run toward fear | Ben Horowitz (a16z)

Eating Lunch Together Builds Team Trust

Ben explains that having everyone eat lunch together builds rapport, relationships, and trust, a simple practice teams undervalue in remote-work settings.

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Ben Horowitz
$46B of hard truths: Why founders fail and why you need to run toward fear | Ben Horowitz (a16z)

Life Isn't Fair - Focus On What's Next

Ben’s guiding motto from his father is that life is not fair, and dropping expectations of fairness lets you focus on what to do next...

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Claire Vo
Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD)

Sales-Led Companies Can Build Great Products

Claire contends sales-led companies can still craft excellent products and provide rewarding PM careers, citing SAP as an example.

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Mike Krieger
Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram)

Product Design Resolves Tension Between AI Autonomy and User Control

He explains that good product design resolves the tension between the model taking over and engaging users enough to keep them in control.

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Ethan Smith
The ultimate guide to AEO: How to get ChatGPT to recommend your product | Ethan Smith (Graphite)

Team Structure for AEO Success

Pair an SEO team for on-site AEO work with a marketing-community generalist for YouTube and Reddit citation outreach.

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Will Larson
The engineering mindset | Will Larson (Carta, Stripe, Uber, Calm, Digg)

Values Must Filter Hiring Decisions

Will emphasises keeping only values that actively filter hiring decisions and dropping the rest to maintain focus.

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Owen McCabe
How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO)

AI Will Create Leaner Organizations with Human-Agent Collaboration

Automation will create leaner, flatter organisations where humans oversee a medley of specialist and glue agents.

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Nick Turley
Inside ChatGPT: The fastest growing product in history | Nick Turley (OpenAI)

Surround Yourself With Smart People

Nick bases career and life choices on the belief that you become the average of the people you spend the most time with, so he...

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Peter Dang
From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products

Building Teams With Complementary Spikes

Peter spent as much time recruiting complementary ‘spikes’ as on product work at OpenAI, arguing team composition is the highest-return investment for leaders.

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Garrett Lord
Inside the expert network training every frontier AI model | Garrett Lord

Separate Teams for New Business Success

Garrett kept engineering, design, finance and ops entirely separate so staff had one job—making Handshake AI succeed.

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Nabil Qureshi
How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir)

Building Strong Internal Team Culture

Create a tight internal culture of trust so everyone assumes teammates are great, using high-bar past workplaces as benchmarks.

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Jake Knapp
Rapidly test and validate any startup idea with the 2-day Foundation Sprint

Differentiation Requires Whole Team Input

Jake emphasises that defining and scoring differentiation should involve all co-founders and core team members, not just marketing or sales.

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Claire Vo
Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD)

Personal SLA Prevents Bottlenecks

Set a fast personal response time so you never become the decision bottleneck for your team.

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Asha Sharma
How 80,000 companies build with AI: Products as organisms and the death of org charts | Asha Sharma

Focus on Loops Not Lanes

Teams must obsess over the continuous feedback loop—cost, rewards, UI, system design—rather than rigid functional lanes.

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Mike Krieger
Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram)

Dario's Accurate Predictions Shift Timeline Expectations

Mike shares that Dario's accurate track record on capability predictions has made him take near-term AI timelines far more seriously.

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Benjamin Mann
Anthropic co-founder: AGI predictions, leaving OpenAI, what keeps him up at night | Ben Mann

Mission-Driven Culture Helps Anthropic Retain Talent Despite Mega Offers

Ben explains that Anthropic retains top people because an egoless, mission-driven culture makes huge external offers easy to ignore.

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Owen McCabe
How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO)

Values-Based Performance System Reshaped Company Culture

He rewrote company values, scored employees each quarter on goals and behaviours, and automatically exited those below a threshold to reshape culture.

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Dan Shipper
The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code. | Dan Shipper (Every)

Sip Seed Funding Preserves Creative Freedom

Raising only modest capital and using a callable “sip seed” SAFE preserves creative freedom and a playful culture while still allowing institutional ambitions.

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Brian Balfour
Why ChatGPT will be the next big growth channel (and how to capitalize on it) | Brian Balfour

Platform Cycles Driven by Competitive Incentives, Not Evil Intent

Brian argues platform self-preservation stems from capitalist incentives rather than malice, urging leaders to engage pragmatically.

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Ben Horowitz
$46B of hard truths: Why founders fail and why you need to run toward fear | Ben Horowitz (a16z)

Measured Hiring of Experienced Talent Accelerates Growth

Refusing to hire experienced talent is equally harmful; founders must bring in experts when specialised knowledge accelerates the company.

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Dan Shipper
The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code. | Dan Shipper (Every)

AI Operations Lead Accelerates Company Productivity

Dan recommends bringing on process-oriented people who love tinkering with AI and know the craft they support to run internal AI operations.

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Lenny Rachitsky
From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products

PMs With Researchers Create More Value Than PMs On UX Teams

Anthropic and OpenAI found greater leverage by pairing product managers directly with model researchers instead of only UX teams.

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Claire Vo
Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD)

Tell Your Boss What Role You Want

Claire advises explicitly telling your boss the exact next role you want, tracking progress, yet keeping such talks to under 1% of interactions.

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Owen McCabe
How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO)

PMs Run Areas Like Mini CEOs at Intercom

Owen shares that Intercom’s sprawling product strategy required PMs to run areas like mini CEOs, broadening their skill sets beyond design.

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Annie Duke
This will make you a better decision maker | Annie Duke (Thinking In Bets, former pro poker player)

Use "Nevertheless" to Balance Listening and Decision Enforcement

Using “I hear you, nevertheless…” lets others feel heard while you still enforce the final decision, helpful for parenting and teams.

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David Plasik
Naming expert shares process for creating billion-dollar brands: Vercel, Azure, Windsurf, Sonos

Bold Names Create Tension

Leaders must overcome the human bias for comfortable, familiar names and back bold, unfamiliar choices.

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Dan Shipper
The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code. | Dan Shipper (Every)

Build Companies Around Work You Secretly Love

Dan urges founders to design companies around the work they secretly love instead of cargo-culting standard models.

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Matt Lemay
The one question that saves product careers | Matt LeMay

Business Model Reveals True Company Priorities

Understanding how the business model actually makes money reveals true company priorities and ethical fit for employees.

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Howie Liu
How we restructured Airtable's entire org for AI | Howie Liu (co-founder and CEO)

Technical, Design, and Product Skills Overlap at Google, Apple, and Stripe

He highlights Google, Apple, and Stripe as examples where technical, design, and product skills overlap within roles.

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Howie Liu
How we restructured Airtable's entire org for AI | Howie Liu (co-founder and CEO)

Field Agents Team's Open Experimentation Approach

Howie tells his Field Agents pod to explore multiple feature directions and build quick prototypes instead of waiting for prescriptive instructions.

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Brett Taylor
He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor (Sierra)

Outcome-Based Pricing Aligns Vendors as Partners

Brett argues outcome-based contracts turn software sellers into genuine partners because revenue depends on delivering the customer’s goal.

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Andrew Wilkinson
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson

Being the Buyer You Wish You Had

Andrew’s philosophy is to act as the empathetic buyer he wished he'd had, avoiding the private-equity ‘suit’ mindset.

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Claire Vo
Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD)

Claire's Business Model Interview Question

Claire asks PM candidates how they'd improve the business model to test understanding of pricing, unit economics and leverage points.

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Benjamin Mann
Anthropic co-founder: AGI predictions, leaving OpenAI, what keeps him up at night | Ben Mann

Small Extinction Risk Warrants Extreme Caution

Ben argues even a one-percent extinction risk warrants extreme caution, likening it to boarding a flight with such odds.

PD
Peter Dang
From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products

Interview Question: Painful Mistakes Reveal Growth Mindset

Dang asks candidates for their most painful mistake and how it changed their work to gauge self-reflection, vulnerability, and growth mindset.

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Nabil Qureshi
How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir)

Filter First Hires for Mission Fit

Aggressively filter first hires for deep mission fit by asking questions like “What’s the hardest you’ve worked to get something done and why?”.

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Claire Vo
Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD)

Technical Expertise Required for CPTO Role

Claire stresses you must be technical to run product, engineering and design because driving velocity hinges on understanding how software gets built.

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Garrett Lord
Inside the expert network training every frontier AI model | Garrett Lord

Flat Structure Celebrates Impact

Flat structure highlights individuals 'putting up points', fostering fun, results-focused environment.

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Mike Krieger
Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram)

Optimizing AI for Work Completion, Not Likability

Mike warns against optimising for likability or time-spent and instead focuses on whether Claude actually helps people accomplish work.

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Will Larson
The engineering mindset | Will Larson (Carta, Stripe, Uber, Calm, Digg)

Engineering Leaders Must Pivot Beyond Hiring

With hiring slowed, engineering directors must now excel at team leadership, technical depth, and right-sizing rather than just recruiting.

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Nabil Qureshi
How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir)

Data Gatekeepers Resist Democratization

Nabil explains some staff resist democratising data because their value and job security depend on being the sole gatekeepers of critical sales queries.

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Howie Liu
How we restructured Airtable's entire org for AI | Howie Liu (co-founder and CEO)

Make Every Function Full-Stack

Make every function more full-stack—AEs demo fluently, marketers run ads end-to-end—reducing dependencies and increasing outcome ownership.

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Matt Lemay
The one question that saves product careers | Matt LeMay

PM's Role: Facilitating Team-Wide CEO Thinking

Matt argues the PM's job is to ensure the whole team thinks like a CEO rather than acting as a lone mini CEO.

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Benjamin Mann
Anthropic co-founder: AGI predictions, leaving OpenAI, what keeps him up at night | Ben Mann

Prepare for Accelerating Technological Weirdness

He advises leaders to mentally prepare for accelerating technological weirdness because the present is the new normal.

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Benjamin Mann
Anthropic co-founder: AGI predictions, leaving OpenAI, what keeps him up at night | Ben Mann

Safety First Drove Anthropic's OpenAI Exit

The Anthropic founders prioritised safety above all, leaving OpenAI to build an organisation where it leads every decision.

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Mike Krieger
Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram)

Product Teams Focus on Empathy and Strategy as AI Automates Execution

Mike argues product managers remain vital for empathy, comprehension, and strategic focus even as AI automates execution.

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Mike Krieger
Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram)

Mike Joined Anthropic to Shape AI's Future

Mike joined Anthropic to maximise his ability to nudge AI development toward better futures for his kids and society.

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Asha Sharma
How 80,000 companies build with AI: Products as organisms and the death of org charts | Asha Sharma

Full Stack Builders Thrive in AI Era

Polymath builders who own multiple disciplines cut 500 touchpoints to speed product loops in AI-era organisations.

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Madhavan Ramanujam
Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam

Negotiation as Core Monetization Lever

Sees negotiation as a core monetisation lever, arguing that failing to contextualise price leaves money on the table.

OM
Owen McCabe
How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO)

Ego Death Improves Leadership Effectiveness

Surviving a painful two-year crisis destroyed his ‘perfect leader’ ego, removing insecurities and triggers that previously limited leadership impact.

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Nick Turley
Inside ChatGPT: The fastest growing product in history | Nick Turley (OpenAI)

Setting the Resting Heartbeat for Teams

Nick sees part of his role as establishing the team's default pace so everyone knows how fast to move.

DS
Dan Shipper
The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code. | Dan Shipper (Every)

AI Will Reshore American Jobs

Dan predicts cheap AI intelligence will reshore many US roles by boosting service demand and raising local worker productivity.

CC
Chip Conley
Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)

Culture Guides Decisions and Attracts Right People

He says culture both guides day-to-day decisions and attracts people whose values align with the organisation.

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Matt Lemay
The one question that saves product careers | Matt LeMay

Curious PMs Understand Business Success

Matt highlights that the best PMs stay deeply curious about what success means for their specific business context.

CC
Chip Conley
Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)

Curiosity and Energy Trump Age in Tech

Older tech workers who stay curious, positive, and play both mentor and mentee roles overcome age bias and remain valuable.

PD
Peter Dang
From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products

Creating Custom Roles Around Individual Strengths

Peter watches what excites people, has them document it, then shapes new roles so individuals can lean fully into their unique technical plus taste strengths.

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Owen McCabe
How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO)

Intercom's Nothing To Lose AI Pivot

Owen says Intercom pivoted fully to AI because they had "nothing to lose," embracing risk others might avoid.

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Matt Lemay
The one question that saves product careers | Matt LeMay

Stay Curious During Success

When things are going well, stay curious, learn from other teams, and build connections before inevitable plateaus.

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David Plasik
Naming expert shares process for creating billion-dollar brands: Vercel, Azure, Windsurf, Sonos

Polarization Signals Strong Brand Names

Internal disagreement signals a bold, energetic name worth pursuing rather than a safe consensus pick.

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Howie Liu
How we restructured Airtable's entire org for AI | Howie Liu (co-founder and CEO)

Passion-Driven Entrepreneurs Build Better Products

He contrasts passion-driven entrepreneurs with purely financial ones, arguing great product-centric companies are led by builders who love the product.

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Brett Taylor
He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor (Sierra)

Building Things to Predict the Future

Brett says he lives by Alan Kay’s idea that building things yourself is the surest way to shape what comes next.

HL
Howie Liu
How we restructured Airtable's entire org for AI | Howie Liu (co-founder and CEO)

IC CEOs Drive Non-Incremental Outcomes

Howie believes CEOs operating as individual contributors, deep in meaningful details, spark non-incremental outcomes without slipping into micromanagement.

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Claire Vo
Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD)

Budget Shifts from Hiring to Automation

Claire foresees leaders reallocating spend from new hires to automation software as efficiency gains change role ratios.

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Nick Turley
Inside ChatGPT: The fastest growing product in history | Nick Turley (OpenAI)

Smart People With Ideas Drive OpenAI Innovation

OpenAI lets anyone with a strong idea pursue it, reflecting its research-lab roots and fuelling much of their product innovation.

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Andrew Wilkinson
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson

Success Is Choosing Your Own Game

Success can mean a calm, headphone-on craft life not billion-dollar domination, so choose your game deliberately.

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John Zorotsky
Rapidly test and validate any startup idea with the 2-day Foundation Sprint

AI Can't Replace Differentiation Thinking

Even with AI building the mock-ups, teams must craft the copy and differentiation themselves.

HL
Howie Liu
How we restructured Airtable's entire org for AI | Howie Liu (co-founder and CEO)

AI Products Need Better Visual Metaphors

Howie views product UX as defining what the product should do and how it behaves, arguing AI tools undersell themselves with poor metaphors and affordances.

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Garrett Lord
Inside the expert network training every frontier AI model | Garrett Lord

Incubating New Products Inside Mature Companies

Garrett Lord says incubating a new zero-to-one product inside a 600-person, 10-year-old company demands very different ways of working from running the mature core business.

PD
Peter Dang
From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products

Founder-Market Fit Through PM Archetypes

Peter stresses aligning a founder’s dominant PM archetype with the market so passion and perseverance remain high.

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Nabil Qureshi
How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir)

Startups Need People Who Go Beyond Checkboxes

Early-stage startups must select people willing to give an extra 20 % beyond checkbox tasks, making big-company mindsets risky hires.

LR
Lenny Rachitsky
Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD)

Propose Solutions to Business Problems That Expand Your Role

Focus on what your manager and business are struggling with and propose solutions that expand your role.

CC
Chip Conley
Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)

Brian Chesky's Humble Curiosity

Brian openly admitted “I don’t know what I’m doing” and consulted specialists, e.g., ex-CIA chief after a security debacle and Chip for hospitality know-how.

JZ
John Zorotsky
Rapidly test and validate any startup idea with the 2-day Foundation Sprint

Engineers Gain More Value By Testing Before Coding

Engineer founders gain more value by clarifying differentiation and testing with customers before writing code.

BH
Ben Horowitz
$46B of hard truths: Why founders fail and why you need to run toward fear | Ben Horowitz (a16z)

Irrational Desire, Not Money, Sustains Founders

Ben says only an irrational, purpose-driven urge—not money—sustains founders through inevitable hardships.

WL
Will Larson
The engineering mindset | Will Larson (Carta, Stripe, Uber, Calm, Digg)

Understand Incentives Before Solving EM-PM Conflicts

He advises EMs and PMs to first understand each other's true incentives and needs before debating solutions, as most conflicts stem from misperception not malice.

AS
Asha Sharma
How 80,000 companies build with AI: Products as organisms and the death of org charts | Asha Sharma

Agents Transform Org Charts Into Work Charts

Capable agents shrink hierarchies as organisations move from reporting lines to task-based collaboration and automatic routing.

BB
Brian Balfour
Why ChatGPT will be the next big growth channel (and how to capitalize on it) | Brian Balfour

Moats Need Ecosystems to Scale Quickly

Brian urges leaders to seize a discovered moat rapidly by mobilising an ecosystem because defensibility cannot be amassed alone.

PD
Peter Dang
From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products

Language Precision Has Multiplicative Effects

Precise wording in decks and docs prevents misinterpretation and has a multiplicative effect on downstream execution.

WL
Will Larson
The engineering mindset | Will Larson (Carta, Stripe, Uber, Calm, Digg)

Challenging Projects Build Strongest Bonds

Will reflects that unchosen, high-pressure projects forge strong bonds and lasting growth when tackled with people you respect.

CC
Chip Conley
Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)

Intergenerational Collaboration Benefits

Chip promotes pairing older managers and younger staff so each swaps technical know-how and leadership skills.

CV
Claire Vo
Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD)

Optimize Organization Around Talent, Not Structure

Claire advises structuring product-engineering-design leadership based on the CEO’s and team’s skills rather than following one perfect org chart.

LR
Lenny Rachitsky
How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir)

Clarify Who Your Company Values Exclude

When crafting company values you must specify who will not thrive, intentionally excluding misaligned hires to strengthen culture.

MR
Madhavan Ramanujam
Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam

Market Share and Wallet Share Need Equal Attention

Leaders should give equal strategic attention, though not necessarily equal effort, to both market share and wallet share at every stage.

HL
Howie Liu
How we restructured Airtable's entire org for AI | Howie Liu (co-founder and CEO)

Founders Must Taste AI Soup Directly

Staying the ‘chief taste maker’ now requires founders to work directly with AI tools, tasting the soup by building and using features themselves.

LR
Lenny Rachitsky
How we restructured Airtable's entire org for AI | Howie Liu (co-founder and CEO)

Fast Thinking Teams for AI Success

Shift company culture to move fast, ship early, play with latest models daily, and frequently reset expectations about AI’s accelerating pace.

BT
Brett Taylor
He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor (Sierra)

Agents Will Drive Next Major Productivity Wave

He believes fully autonomous agents will spark economy-wide productivity gains similar to the 1990s ERP revolution.

BM
Benjamin Mann
Anthropic co-founder: AGI predictions, leaving OpenAI, what keeps him up at night | Ben Mann

Anthropic Hiring Aggressively Despite AI Productivity Gains

Ben believes the next years are critical, so Anthropic hires aggressively even while tooling multiplies productivity.

OM
Owen McCabe
How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO)

Founder Mode Leads Intercom's Transformation

Frustrated by compromises and slowing growth, McCabe switched to a top-down, founder-first style he calls deeply cathartic for steering the company decisively.

BH
Ben Horowitz
$46B of hard truths: Why founders fail and why you need to run toward fear | Ben Horowitz (a16z)

Document Expectations Instead of Yelling

If you repeatedly yell at a team, it signals you have not clearly explained what you want, so document expectations instead of venting frustration.