Pinterest

Ad Strength Hole-in-the-Ship Diagnostic

Use Google's brand vs non-brand ad-strength report to find the one fix that lifts the whole account

Advise Like an Investor: The Company Selection Filter

Your advisory portfolio is an investment portfolio — pick for the liquidity event, not the logo

AI Answer Box Keyword Triage

Segment your keywords by intent, quarantine the informational ones, and start teaching the AI

Self-Mastery4 steps

AI as Undermind Mirror

Use a structured five-days-of-questions prompt to make an LLM reflect back patterns you already sense but can't articulate.

Peak Performance6 steps

Artifact Reverse-Engineering and Backstage Observation

Collect the best artifacts, reverse-engineer their questions, then go watch the sausage get made.

Assume the Disruptor Is Right

During an existential threat, assume the disruptor is playing an optimal game and respond with overreaction

Back-Channel Reference Digging

Trust peer back-channels over provided references, and probe harder than feels comfortable.

Balcony Rhythm for Co-Founder Relationships

Build shared self-awareness, then protect the relationship with vows and a real check-in cadence

Be Interested, Not Interesting

Play small talk like hacky sack: set the other person up to succeed and balance disclosure over time

Finance3 steps

Belsky's Founder Bet Checklist

Back mission-driven, pragmatically pessimistic founders building products with a clear object model.

Best-for-the-Role, Not Best-in-Market

Hire for the specific mandate at this specific stage, not the most impressive resume available.

Building Toward a Portfolio Career

Engineer a narrow-but-deep expertise plus branded credibility so you can advise many companies, not one.

Peak Performance4 steps

Build Taste by Watching Adjacent Software

Develop design intuition by watching real people use OTHER products, not your own.

Capacity-Red Headcount Justification

Add headcount only when a days-committed-vs-days-in-quarter calculator stays red after cutting low-value work

Cater to the Individual, Not the Average

Ask each teammate how involved they want to be, then run decisions to fit their motivation.

Close the Loop: Intent-Signal Retention Engine

Turn every low-commitment user signal into a trigger you can legitimately fire later.

Coach vs. Advise Decision

Stop training your team to bring you every problem by knowing when to coach instead of solve

Confidence-Calibrated Directness

State how strongly you hold each opinion so strong views don't silence the room.

Consumer Subscription Viability Test

Freemium-plus-paid-acquisition consumer subscriptions fail without ~60-70%+ retention or a network effect

Crossing the Product Leader Canyon

Escape the manager death spiral by shifting from doer to editor and owning outcomes over output.

Dare to Be Dull

Strive for connection over perfection to free up cognitive bandwidth when speaking spontaneously

De-Ambiguate Upstream: The Brief as a Prompt

Design is slow only when the brief is vague; remove variables upstream like you'd add context to an AI prompt.

Define the Mandate Before You Search

Get granular on the outcome, spike, and 90-day plan before opening a product-leader search.

Delay the Primal Mark

Stay in low-fidelity blocks and conversation as long as possible before drawing anything that looks real.

De-Risking the High-Stakes Meeting

Turn important meetings from big-reveal gambles into pre-worked, question-proof conversations.

Design Tenants (Decision-Making Rules, Not Principles)

Replace feel-good design principles with 3-4 opinionated tenants that settle recurring debates for good.

Productivity3 steps

Do Half, Then Go on a Killing Spree

Build half the features, then remove things until the one core action runs at 10x velocity.

Earn the Secret by Savoring Surprises

There's no recipe for a breakthrough — hunt surprises at the edge instead of validation

Editorial SEO Operating Model

Split the work: SEO manager picks topics and outlines, a domain-expert writer writes, then analyze.

Self-Mastery5 steps

Energy Audit for Your Zone of Genius

Track what energizes and depletes you for two weeks, then redesign your role toward 80% in your gifts

Communication6 steps

Engineering Honest Feedback

People withhold feedback because it's risky — your job is to make it safe and rewarding.

Excitement-Signal Persona Discovery

Ship a broad tool, then let the segment with the most emotive joy tell you who to focus on

Expected-Conversions Prioritization

Rank topics by search volume x topical authority x conversion intent, not by volume alone.

Productivity5 steps

First-Step Onboarding (Lower Barriers, Raise Delight)

Beat the blank page by walking users through tiny surprising steps until they surprise themselves

Force a Choice, Not a Comparison

Be the world's first banana, not a 10x better apple

Founder Intuition vs Team Expertise Handoff

Delegate to hires only once they consistently make better calls than you would — and signal in both directions

Giving Away Your Legos

To let yourself and the company scale, hand off the work you're best at and find joy in enabling others

GROW Model for Powerful Questions

Four question categories that let people solve their own problem and walk away with a concrete next step

Guild Nights

Six interesting people, one topic, at your house, catered — the highest-ROI network you can build

Hacking Hype (Internal and External)

Manufacture momentum by forcing visibility moments and tying launches to emotion.

Happy GMV and Minimum Viable Happiness

Track only the GMV that produced a retained customer, and boil the thimble until it clears the bar

Hypothesis-Driven SEO

Generate hypotheses by analyzing sites (and asking their SEO managers), then test to validate.

Incrementality via Conversion Lift & Geo Tests

Prove paid actually caused growth by withholding ads from a control group and measuring the lift

Internal Link Spread Optimization

Most sites starve their own pages of internal links; fixing spread is SEO's biggest quick win.

Interview for Design in the DNA

Before joining, verify the founders valued your function from the very beginning; it can't be grafted on later.

Justifying Non-Sexy Product Investments

Fund performance, UX and velocity work by making the invisible measurable and the downside of neglect concrete.

Entrepreneurship3 steps

Keeper of the Flame: The Zero-to-One Trio

Three moves to carry a new idea from spark to company-wide launch: right idea, buy-in, spread.

Kindle and Fire Growth Strategies

Non-scalable kindle hacks exist only to unlock the scalable fire strategy worth hiring for.

KPI + Narrative: The Two-Part Turnaround Drumbeat

Pair one north-star KPI with one relentlessly repeated narrative to reset how a company works.

Self-Mastery4 steps

Leave It Better Than You Found It

Build career capital by making visible, others-verifiable impact — not by collecting logos.

Live in the Future and Notice What's Missing

Don't try to think of a startup idea — get out of the present so ideas find you

Strategy3 steps

Market Map, Then Go a Layer Deeper

Start from the best companies for a skill, but never assume a great logo means a great individual.

Markets as Currents, Not Bodies of Water

Chase the change dynamic pulling the market, not the size of the market

Merchandise Progress Through the Messy Middle

Short-circuit the human reward system with agreed micro-goals and a narrated sense of progress.

Non-Violent Communication (OFNR) for Difficult Conversations

Observation, feeling, need, request — get mutual understanding instead of trying to win the argument

One-Page Plan and Operating Rhythm

Put vision through quarterly goals on one page, then meet in a rhythm to reflect on it

Strategy3 steps

Optimize for the Problems You Want to Have

Only build features that stop people from reaching the point where they'd ask you for more.

Self-Mastery6 steps

Outcome-Backwards Skill Acquisition

Pick an outcome that would prove you learned the skill, then work backwards to the experts.

Packaging for Spread, Not for Revenue

Never gate the mechanism that grows you: limit files, not collaborators; charge editors, not viewers.

Paid Channel Sequencing Ladder

The order to adopt paid platforms: user-driven search first, disruptive media next, expensive targeting last

Pain-Solution-Proof-Point Vision Pitch

Sell a vision by looping pain, solution, and a real user proof point instead of describing it in words.

Pattern-Breaking Inside a Big Company

Make small bets that can fail a lot — and hide them from the mother ship

Perceived Simplicity

Keep advanced power in the product but discoverable only to those who go looking — invisible to everyone else.

Peak Performance5 steps

Practice-Until-Your-Worst-Is-Good-Enough Interview Prep

Interviewing is the one skill with zero feedback — so run dozens of mocks in a small peer group.

Product-Led SEO (Jobs-to-be-Done, End-to-End)

Map real user jobs to search queries and follow the experience all the way to the magic moment

Mindset3 steps

Reframe Anxiety as Excitement

Relabel the identical arousal response from nervous to excited to calm yourself and speak better

SaaS-Marketplace Transition Test

A SaaS business can add a marketplace only if it touches its customer's customer and those customers need multiple suppliers

Scenario-Based PM Interviewing

Interview PMs by making them do the real job under real constraints, not recite prepared stories

SEO Readiness Assessment

Two questions decide if SEO is worth investing in: is the market big, and do you have authority?

SERP Reverse-Engineering

To learn what page to build, read what Google already ranks for your target keywords.

Productivity3 steps

Ship-to-Learn Research Allocation

Reserve scarce user research for high-uncertainty, high-leverage problems; ship to learn everywhere else

Signal Over Metrics (Pre-PMF Decision Rule)

You cannot optimize your way to product-market fit — hunt for pull, not conversion lifts.

Signals and Nudges for Choice Under Abundance

When every result is plausible, confidence beats relevance — surface glanceable signals, not more inventory.

Signal vs Noise Metric Selection

Let the campaign's single goal decide which metric is signal — everything else is noise

Peak Performance3 steps

Speaking Visualization Rehearsal

Mentally rehearse the whole speaking event in advance to desensitize yourself and gain a sense of agency

Sponsorship Over Mentorship

Career inflection comes not from a coach but from a sponsor who trusts you with a bigger problem.

The ADD Answer Structure

Answer, Detailed example, Describe relevance: give complete, value-adding responses in Q&A

Mindset4 steps

The A-Minus Idea: Conviction as a Catalyst

Put out an opinionated idea to react to — people respond to an idea far more than to nothing.

Self-Mastery7 steps

The Bootloader: Structured Morning Self-Reflection

Boot the day with exercise, then run an hour of red-yellow-green review across every role in your life

The Bottom-Up Fit Checklist

Four market conditions plus one leadership condition that decide whether an IC-led motion will work.

The Calibration Test for Recruiters

Vet a recruiter by testing whether they can play back your brief and name candidates on the spot.

The Champion Amplification Flywheel

Grow your internal champions' careers, and their credibility becomes your credibility.

The Coaching Model (Coaches, Not Managers)

Replace managers with same-specialty coaches whose only job is your skills and your next level

The Community Node-Graph Channel Strategy

Map the influence graph of an existing community, then go to its centres — for feedback, not a pitch.

Self-Mastery3 steps

The Complementary-Axis PM Skill Development Framework

Level up (or transition into) PM by picking the skill axis opposite your background, then strategy

Entrepreneurship3 steps

The Conviction Test for Whether to Quit

Compare your conviction now versus at the start to decide whether to persevere or pivot.

The Delight-First MVP Test

Don't launch until the product sparks joy in your first users, because they are your only growth channel

The Enthusiastic Rehire Test

One binary question that cuts through months of avoided talent decisions

Innovation3 steps

The First Mile: Lazy, Vain, and Selfish

Design onboarding for the first 30 seconds, when every new user is lazy, vain, and selfish.

Self-Mastery4 steps

The Fish-and-Water Strength Test

Your real strength is the thing others praise that you think is no big deal.

The Five-Legged Stool

Product, eng, design, insights, and marketing as one leadership team — with the PM accountable, not king.

The Four I's Feedback Structure

Information, Impact, Invitation, Implications: package feedback so it lands as collaborative problem-solving

The Four Keys to IC Love

Credibility, build-with-users, go where they already are, and radical transparency.

The Four Types of Product Work

Feature, growth, PMF-expansion, and scaling work — the portfolio a product leader must learn to balance.

Finance5 steps

The Front-Loaded Advisor Equity Structure

Equity only, a three-month cliff, vesting front-loaded to the value, and an exit built in

Entrepreneurship5 steps

The Growth Advisor Sourcing and Vetting Gauntlet

Wait for PMF, source through VCs and channel-leading companies, and borrow a trusted expert to vet

The Hierarchy of Engagement

Three stacked levels — core action, accruing benefits, self-perpetuation — that decide if a consumer product endures

Entrepreneurship5 steps

The Hierarchy of Marketplaces

Focus, tip, dominate — the only sequence that produces a marketplace worth owning

The 'If I Could Have Written It' Content Bar

A one-question filter for whether technical content will earn credibility or be ignored.

The Inflection Stress Test

Four questions that separate a real inflection from a vague 'why now'

Innovation3 steps

The Object Model: Three Questions Every Screen Must Answer

On every screen, a user should know how they got here, what to do now, and what to do next.

Peak Performance4 steps

The One-Skill Six-Month Block

Go all in on one skill for 3-6 months: study one example a week, practise it an hour a day.

The Ops Cadence Spreadsheet

A rocks-and-pebbles spreadsheet that assigns every account task a defined weekly/biweekly/monthly rhythm

Sales5 steps

The Practitioner Advocate Role (The Tom Factor)

Hire a passionate user from your community into marketing and sales — no quota, no CRM.

The Pre-Need Talent Pipeline

Build relationships with great people long before you have a role open, with no agenda.

The Product Career Learning Loop

A four-stage loop — execute, generalize, communicate, scale — that compounds a PM's ability over a career.

The Product People Spectrum: Innovators to Executors

Great product careers get filtered at strategy — deliberately move executors toward the strategic middle.

The Provenance Gate: Scaling Supply Without Diluting the Brand

Let sellers scale by outsourcing production — but only to a partner whose process they actually know.

Peak Performance3 steps

The Rule of Lung

Make your exhale twice as long as your inhale to trigger the relaxation response before speaking

The SEO Staffing Stack Rank and Impact Clock

Internal expert, then a relentless doer surrounded by advisors, then agencies — and 3 to 12 months to prove it

The Signs of Life Test

Spend a tiny budget on a new platform to detect a positive signal before committing to a full campaign

Influence6 steps

The Smallest-Ask Mentor Ladder

Never ask 'will you mentor me?' — ask a two-minute question, then earn the next rung.

The Story Chapters Framework for Executive Communication

Find the last obvious point for your audience, then build from there — skip neither the setup nor the basics.

Leadership7 steps

The Three-Chapter Hiring Playbook: Find, Assess, Close

Hire the top 1% by hunting signs of excellence, then closing with the whole exec team and the family

The Three Elements of a Breakthrough Idea

Grade any startup idea on inflections, insight, and founder-future fit — not the implementation

The Three-Hire Performance Team Sequence

Build a paid team in order: data-driven generalist, then creative, then a dedicated data scientist

Mindset3 steps

The Three Mindset Shifts That Stall or Restart PM Growth

Fix the three stories — control, change, and self-image — that quietly stall product careers

The Three Network Effects (and Why Social Products Must Evolve)

Classify defensibility as direct, cross-side, or data network effects — and know social products must add the latter two

The Three Pattern-Breaking Actions

Movements, storytelling, and disagreeableness — how you get people to move to your future

The Three-Pillar AI Integration Model

Build where you have data advantage, partner for commodities, and open an app ecosystem for the rest

The Three-Slide Believer Pitch

What you do, your non-obvious insight, then proof — built for believers, not objectors

The Three Tenets of PM Stakeholder Collaboration

A mantra for working with stakeholders: surface issues, not yourself; drive decisions, don't hoard them

The Three Types of SEO

Programmatic, editorial and technical SEO are different games; pick the one your queries reward.

The Three Ws of PM Career Growth

Rise faster by performing on all three axes: what you produce, what you bring, and how you operate

The Tippability Test

Check supply fragmentation, supply heterogeneity and incumbent competition before you fund a marketplace

The Transaction Tiebreaker for Marketplace Prioritization

Stop arguing supply vs demand — make the transaction itself the thing every team is accountable to.

The Triple-A Apology

Acknowledge, Appreciate, Amend: apologize for the transgression, not for how someone feels

The True Competition Metric

Use auction-insights math to tell a genuine competitive threat from a harmless close-variant accident

The Two-Bucket SEO Fit Test

Does your product mint pages by itself? The answer decides your entire SEO strategy

The Two-Step Bottom-Up GTM Motion

Make individual contributors love you, then arm them to spread you inside their company.

Productivity4 steps

The Weekly Focus Ritual

Post what you're focused on this week, and whether last week's focus actually landed.

The WHAT Toast Structure

Why we're here, How you're connected, Anecdote, Thank you: a GPS for any toast or tribute

Productivity4 steps

The YOLO Rule: When Not to Run an Experiment

Experiments have a cost — sometimes shipping 40 things fast beats testing 10 things properly

Three Levels of Listening

Drop from your own inner monologue into hearing what people communicate beneath their words

Three Ways to Find Marketplace Whitespace

Unbundle a low-NPS segment, own an ignored niche, or change the atomic unit of supply

Tipping Loops: Growth Loops and Happiness Loops

Two symbiotic loop types — one grows the marketplace, one keeps it happy as it grows

Productivity4 steps

Top-Down / Bottoms-Up Core Action Analysis

Cross two analyses — return-propensity ranking and product purpose — to find the one action worth optimising

Topical Authority Adjacency

Rank by starting where you're already known, then expand into semantically adjacent topics.

Topics Over Keywords

Modern Google ranks one page for a cluster of 200-2,000 keywords; target the topic, not the keyword.

Turn Your Biggest Blocker Into Your Upgrade Wedge

Find the single thing stopping adoption, go deeper on it than anyone, and make it the reason to upgrade.

User Immersion to Roadmap Loop

Turn constant user and non-user conversations into a prioritized roadmap and sales evangelism.

Values, Not Behaviors: The Culture Car Wash

When you change companies, keep the values that got you hired but recalibrate the behaviors to the new culture.

What / So What / Now What

A three-part structure that turns any on-the-spot update or answer into a memorable, digestible message