Get a second opinion from the people who shaped modern product thinking. Each advisor is a comprehensive profile built from podcast episodes, newsletter writing, published articles, conference talks, and career history. Processed through a 13-dimension personality extraction. Validated against interviews the AI never saw.
21 advisors. 289 podcast episodes, newsletter articles, published writing, and career profiles analyzed. Not affiliated with Lenny or any advisor. Free.
Annie Duke Decision strategist, author of Thinking in Bets and Quit, Special Partner at First Round Capital
Verified to 74% accuracy against the real Annie Duke's answers. Tested across 27 held-out questions. How we validate → Decision-Making Under Uncertainty Structured Decision Processes Quitting Decisions
Helps teams make better decisions under uncertainty. Author of Thinking in Bets and Quit. Former pro poker player, embedded at First Round Capital.
Chat → April Dunford World's leading product positioning expert; author of Obviously Awesome & Sales Pitch
Verified to 80% accuracy against the real April Dunford's answers. Tested across 14 held-out questions. How we validate → Product Positioning B2B Sales Pitch Buyer Psychology & Indecision
Fixes positioning so customers instantly get what you are and why they should care. Repositioned 200+ companies. Author of Obviously Awesome.
Chat → Ben Horowitz Co-founder of a16z; author of The Hard Thing About Hard Things
Verified to 78% accuracy against the real Ben Horowitz's answers. Tested across 18 held-out questions. How we validate → CEO leadership executive hiring company culture
For when every option looks terrible and you still have to decide. Co-founder of a16z. Former CEO of Loudcloud/Opsware. Author of The Hard Thing About Hard Things.
Chat → Brian Balfour Founder & CEO of Reforge, Former VP Growth at HubSpot
Verified to 80% accuracy against the real Brian Balfour's answers. Tested across 11 held-out questions. How we validate → Growth Strategy Distribution Platforms Product-Led Growth
Built the Four Fits framework for scaling to $100M+. Four-time founder, former VP Growth at HubSpot, now runs Reforge.
Chat → Casey Winters Growth & marketplace strategist; ex-CPO Eventbrite; ex-Growth Pinterest & GrubHub
Verified to 70% accuracy against the real Casey Winters's answers. Tested across 6 held-out questions. How we validate → Growth Strategy & Loops Marketplace Dynamics Product Management & Leadership
Growth strategist who thinks frameworks are tools, not coloring books. Grew Pinterest, GrubHub, Eventbrite. Advises Airbnb, Reddit, Canva.
Chat → Claire Hughes Johnson Former COO of Stripe, Author of Scaling People
Verified to 82% accuracy against the real Claire Hughes Johnson's answers. Tested across 28 held-out questions. How we validate → Scaling Companies Operating Systems & Cadences Hiring & Talent Systems
Scaled Stripe from 160 to 7,000+ people as COO. Author of 'Scaling People.' 11 years at Google in 8 roles. Boards: HubSpot, The Atlantic.
Chat → Dharmesh Shah Co-founder & CTO, HubSpot
Verified to 76% accuracy against the real Dharmesh Shah's answers. Tested across 17 held-out questions. How we validate → SaaS Scaling Company Culture Startup Ideas
Scaled HubSpot to $30B+ by treating culture as a product. Co-founder/CTO with zero direct reports ever. Created the Culture Code deck (5M+ views).
Chat → Drew Houston Co-founder & CEO of Dropbox; 18-year founder-CEO who survived Apple, Google, and Microsoft
Verified to 74% accuracy against the real Drew Houston's answers. Tested across 16 held-out questions. How we validate → Competing with Big Tech Founder Psychology Viral Growth
Survived Apple, Google, and Microsoft all trying to kill his company. Built Dropbox from a side project to IPO. 18-year founder-CEO.
Chat → Dylan Field CEO & Co-founder of Figma
Product Design & Craft Multi-Product Strategy Startup Scaling
Co-founded Figma in 2012 after a Thiel Fellowship. Led it from 2 people to 1000+ and IPO. Believes design is the competitive moat in software.
Chat → Elena Verna Head of Growth, Lovable | Former CMO Miro, SVP Growth SurveyMonkey
B2B Growth Strategy Product-Led Growth Product-Led Sales
Tells you what actually drives growth (and what doesn't). 15+ years at SurveyMonkey, Miro, Dropbox, Amplitude, now Lovable. Known for growth loops and the 10 anti-patterns.
Chat → Eric Ries Creator of the Lean Startup Methodology, Founder of LTSE
Verified to 80% accuracy against the real Eric Ries's answers. Tested across 6 held-out questions. How we validate → Lean Startup MVP Strategy Pivoting
Helps you figure out what to test, when to pivot, and how to stop wasting time building the wrong thing. Creator of the Lean Startup methodology.
Chat → Geoffrey Moore Technology Strategy Consultant & Author of Crossing the Chasm
Crossing the Chasm Go-to-Market Strategy Market Segmentation
Wrote the playbook for B2B go-to-market strategy. Author of Crossing the Chasm. Advisor to Salesforce, Microsoft, and Google for 30+ years.
Chat → Gibson Biddle Ex-VP Product Netflix; Ex-CPO Chegg; product strategy teacher to 500K+ PMs
Product Strategy (DHM) Prioritization (GEM) A/B Testing & Experimentation
Teaches product strategy through the DHM and GEM frameworks to 500K+ PMs. Ex-VP Product at Netflix, CPO at Chegg (took it public).
Chat → Gokul Rajaram "Godfather of AdSense"; DoorDash executive; board member at Coinbase, Pinterest, The Trade Desk; 300+ angel investments
Product Development Process Hiring Leaders Angel Investing
Self-described 'startup helper' who scaled AdSense to $1B+ and Facebook ads to $6.5B. DoorDash exec, 300+ angel investments, 3 public boards.
Chat → Jackie Bavaro Author of Cracking the PM Interview & Career, Former Head of Product at Asana
Verified to 85% accuracy against the real Jackie Bavaro's answers. Tested across 30 held-out questions. How we validate → Product Strategy PM Career Development PM Interviewing
Wrote the book on PM interviews and PM careers. Co-author of Cracking the PM Interview & Career. First PM at Asana, grew to Head of Product.
Chat → Jason Fried Co-founder/CEO 37signals (Basecamp, HEY); author of Rework; bootstrapping contrarian
Bootstrapping & Independent Business Shape Up (Product Development) Small Team Management
Proves you can build a great company without investors, boards, or growth targets. 25+ years profitable at 37signals. Created Shape Up. Author of Rework.
Chat → Julie Zhuo Co-founder of Sundial | Former VP of Product Design, Facebook/Meta
Verified to 92% accuracy against the real Julie Zhuo's answers. Tested across 12 held-out questions. How we validate → Design Leadership Management & Coaching Product Critique & Review
Turns new managers into confident leaders. 14 years at Facebook, IC to VP of Design. Author of The Making of a Manager. Now co-founder of Sundial.
Chat → Katie Dill Head of Design at Stripe
Design Leadership Design Quality at Scale PM-Design Partnership
Champions beauty as a business driver and quality as growth. Built and scaled design teams 10x at Stripe, Lyft, and Airbnb.
Chat → Kim Scott Author of Radical Candor, CEO Coach, Co-founder of Radical Candor
Radical Candor Feedback & Communication Management Fundamentals
Author of Radical Candor (1M+ copies, 23 languages). Former Google/Apple exec. CEO coach. Teaches caring personally while challenging directly.
Chat → Marc Andreessen Co-founder of Netscape & Andreessen Horowitz (a16z)
Verified to 78% accuracy against the real Marc Andreessen's answers. Tested across 74 held-out questions. How we validate → AI & Technology Futures Venture Capital Strategy Career Strategy in the AI Age
Sees tech platform shifts before everyone else. Invented the web browser, co-founded a16z. 30+ years at the center of every wave from the internet to AI.
Chat → Marty Cagan Founder, Silicon Valley Product Group
Product Discovery Empowered Teams Product Leadership
Teaches companies how to build real empowered product teams. 43 years in product. Former VP at Netscape, SVP at eBay. Author of Inspired, Empowered, and Transformed.
Chat → Matt Mochary CEO Coach to Top Silicon Valley Founders
Verified to 79% accuracy against the real Matt Mochary's answers. Tested across 16 held-out questions. How we validate → CEO Coaching Firing & Layoffs Fear & Anger Management
Helps CEOs do the hard thing they already know they need to do. Coaches founders at OpenAI, Coinbase, Brex, Notion, and Robinhood. Author of The Great CEO Within.
Chat → Nir Eyal Behavioral Design Expert & Bestselling Author
Verified to 94% accuracy against the real Nir Eyal's answers. Tested across 10 held-out questions. How we validate → Behavioral Design Habit Formation Distraction Management
Helps you build habit-forming products and beat the distractions killing your focus. Author of Hooked and Indistractable. Former Stanford lecturer.
Chat → Patrick Campbell ProfitWell founder; pricing & retention expert
Verified to 76% accuracy against the real Patrick Campbell's answers. Tested across 26 held-out questions. How we validate → SaaS pricing subscription retention bootstrapping
Fixes your pricing with data from 20K+ subscription companies, not guesswork. Bootstrapped ProfitWell to a $200M+ exit.
Chat → Petra Wille Independent Product Leadership Coach
Verified to 72% accuracy against the real Petra Wille's answers. Tested across 8 held-out questions. How we validate → PM Coaching Competency Assessment Product Leadership
Helps product leaders find their own way of leading. Coached 130+ PMs across 87+ clients. Author of Strong Product People.
Chat → Rahul Vohra Founder & CEO of Superhuman; pioneer of the Product Market Fit Engine
Product-Market Fit Game Design in Software Pricing Strategy
Created the PMF Engine, the most shared framework on First Round Review. Founder/CEO of Superhuman. Sold Rapportive to LinkedIn. Former pro game designer.
Chat → Richard Rumelt Professor Emeritus of Strategy, UCLA Anderson; Author of Good Strategy Bad Strategy & The Crux
Verified to 84% accuracy against the real Richard Rumelt's answers. Tested across 8 held-out questions. How we validate → Strategy Formulation Bad Strategy Diagnosis Competitive Power & Asymmetry
Helps leaders diagnose their real challenge and cut through bad strategy. Author of Good Strategy Bad Strategy and The Crux. Former NASA engineer, UCLA professor.
Chat → Roger Martin Strategy Advisor, Professor Emeritus at Rotman, #1 Management Thinker
Corporate Strategy Competitive Advantage Integrative Thinking
World's #1 management thinker. Author of Playing to Win. 40+ years advising CEOs on strategy at P&G, Lego, Ford, Verizon.
Chat → Sarah Tavel Venture Partner at Benchmark, former first PM at Pinterest
consumer products marketplace strategy product metrics
Created the Hierarchy of Engagement and Hierarchy of Marketplaces frameworks. First PM at Pinterest. Venture Partner at Benchmark.
Chat → Scott Belsky Founder of Behance, Former CPO of Adobe, Author of The Messy Middle
Product Design & First Mile The Messy Middle Design-Driven Leadership
Helps builders survive the messy middle. Author of The Messy Middle. Founded Behance, former CPO of Adobe, early investor in Pinterest and Uber.
Chat → Seth Godin Author, Entrepreneur, Marketing Thinker
Verified to 76% accuracy against the real Seth Godin's answers. Tested across 21 held-out questions. How we validate → Marketing Strategy Brand Building Product-Marketing Integration
Helps you figure out what promise to make and who your smallest viable audience is. Author of 21 books including Purple Cow. Daily blogger for 10,000+ days.
Chat → Shishir Mehrotra Co-founder/CEO of Coda; inventor of YouTube's skippable ads; author of Rituals of Great Teams
Decision-Making Frameworks Team Rituals & Culture Growth Loops & Pricing
Systematizes how great teams decide and operate. Co-founder/CEO of Coda. Writing Rituals of Great Teams (1,000+ interviews). Led YouTube product at Google.
Chat → Shreyas Doshi Founder, High Leverage Labs | Former PM Leader at Stripe, Twitter, Google
Verified to 84% accuracy against the real Shreyas Doshi's answers. Tested across 8 held-out questions. How we validate → Product Strategy PM Productivity PM Leadership
Helps PMs unstick their careers and think more strategically. 20 years at Yahoo, Google, Twitter, and Stripe. Known for the LNO framework and high agency thinking.
Chat → Stewart Butterfield Co-founder of Slack and Flickr
Verified to 75% accuracy against the real Stewart Butterfield's answers. Tested across 2 held-out questions. How we validate → product-craft b2b-saas pivoting
Twice pivoted failed games into breakthrough products (Flickr, Slack). Built Slack into a $27.7B company through product craft and user empathy.
Chat → Teresa Torres Product Discovery Coach & Author of Continuous Discovery Habits
Verified to 83% accuracy against the real Teresa Torres's answers. Tested across 20 held-out questions. How we validate → continuous-discovery customer-interviewing opportunity-solution-trees
Created the Opportunity Solution Tree to help teams build from outcomes, not features. Author of Continuous Discovery Habits. Coached 18,000+ PMs.
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