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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

Innovation7 steps

AI-First Product Leadership: Hold the Paddles

If AI steers your product, the product leader must own the objective, features, data and infra.

Peak Performance3 steps

All-In / All-Out Delineation

Full intensity when working, full disconnection when not — to keep bringing your best.

Backwards From the Peak: Ambition Set by Potential, Not by Numbers

Derive goals from what the thing could be, then work backwards; today's numbers are not the anchor.

Marketing2 steps

Beautifully Simple Pricing

In your early days, price so a customer can repeat it back and it tells a value story.

Best-Rep Email Cloning

Feed the agent your single best rep's best email, then let it AB-test variants—that's how AI beats your mid-pack.

Influence4 steps

Buy-In as a Journey, Not a Meeting

Win the decision before the decision meeting by looping stakeholders in early and staying open on the solution.

Care Deeply, Challenge Directly — The Feedback Script

Three moves that let hard feedback land as care instead of criticism

Chaos to Clarity

Move any big idea from your head to reality one clarity-adding step at a time.

Productivity4 steps

Closing the Loop with Community

Systematically collect, route, ship, and close every customer request as a product engine.

Strategy3 steps

Column B Thinking

Plan from the dream future backward, not from the bricks in front of you.

Entrepreneurship5 steps

Community as an Economy

Help your fans make a living from your product and their income becomes your distribution

Marketing3 steps

Comprehension Over Friction

Removing friction only helps when intent is high; for most of your product the real problem is comprehension

Content Market Fit

Treat content like a product: pick an audience, find their pain, and ship a painkiller

Productivity5 steps

Context Is All You Need Prompting

Treat the model as a brilliant stranger with zero context, and supply what a colleague would already know.

Mindset6 steps

Conviction-Over-Demand Career Navigation

Stop chasing the most in-demand role; chase the conviction where you can make a dent and learn.

Crazy Big Goals with a Ladder to the Moon

Set an inadequacy-inducing goal, then climb toward it one tiny rung at a time.

De-Risking the High-Stakes Meeting

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

Peak Performance4 steps

Desensitization for Performance Fear

Neutralize public-speaking (or any) fear by exposing yourself in tiny, low-stakes, escalating doses

Innovation6 steps

Diverge-Then-Converge Roadmap Reset

On a platform shift: drop the roadmap, keep the objective, let teams go crazy, then pick 4-5 bets.

Don't Make Me Think (Reduce Thinking, Not Clicks)

Optimize for the fewest decisions, not the fewest clicks — eight trivial taps beat two fraught ones

Excitement-Signal Persona Discovery

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

Leadership3 steps

Fight Club: A Standing Slot for Conflict

Reserve a recurring weekly slot with your key peers specifically to surface and resolve conflict early.

Mindset4 steps

First-Principles Thinking as a Hiring Filter

Build your own framework from context instead of importing one — and hire for it deliberately

Productivity5 steps

First-Step Onboarding (Lower Barriers, Raise Delight)

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

Flying Formation

Define cross-team roles (DACI) plus operating rhythms before growth ships anything

Founder-Led Marketing as a Goodwill Bank

Log what you learn, package it per platform, bank goodwill to spend later

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

Goal-Driven Company Structure

Cascade a mission into pillars into yearly goals so the work you fund IS the mission.

Influence4 steps

Guild Nights

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

High Agency, High Urgency Hiring Filter

Hire for two traits only — people who see a problem and go, and people who go now.

Hyperrealistic Work-Like Activities

As orgs grow, work supply runs out and people fill the gap with fake work that looks exactly like real work

Productivity5 steps

Intentional Remote Operating Model

Make remote work productive by scheduling connection in bursts, protecting synced deep-work blocks, and banning status meetings.

Introvert-Inclusive Meeting Design

Four manager tactics to surface the best ideas from quiet people, not just the loudest three

Justifying Non-Sexy Product Investments

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

Kindle and Fire Growth Strategies

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

Lean Team by Design: Slow Hiring, Player-Coaches, Generalists

Hire painfully slowly, replicate your first-10 DNA, and bet big on the exceptional

Sales6 steps

Mastering B2B Negotiations Through Value

Extract full value from every deal via gives-and-gets, value selling, and disciplined negotiation tactics.

Mindset3 steps

Measure in Hundreds

If your unit of measurement is one hundred attempts, five failures means you have effectively tried zero times.

Productivity3 steps

Meeting Priming Before Decision-Making

Every meeting has a priming phase and a decision phase; skipping or reversing them guarantees dysfunction

Influence5 steps

Organic Mentorship Sourcing

Never ask 'will you be my mentor' — pick managers whose success depends on yours, then bring real problems

Peer Feedback Groups

Small standing peer pods that review each other's rough-draft work to build feedback muscle and trust.

Perceived Simplicity

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

Problem-Centered Wedge

Ignore competitors; find an unsolved painpoint people will pay to fix, then expand.

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

Mindset4 steps

Raising the Longer-Runway Child

Four principles for parenting introverted or shy kids without shaming their temperament

Finance5 steps

Reactive Pricing After Demand Signal

Let users pull pricing out of you, then validate willingness-to-pay and margins

Rejection-as-Refinement Pitching

Treat every investor 'no' as free feedback and pre-answer it in your next deck.

Reverse Engineering to Build Openness

Two reverse-engineering habits that let a conscientious brain manufacture the openness it lacks

Leadership3 steps

Role-Based Culture by Logical Deduction

Replace performative Mission-Vision-Values with a deduced 'role you play' that logically derives your standards

Communication3 steps

Speak Early, Speak From Conviction

Two tactics to get an introvert's ideas heard and acted on in loud meetings

Innovation5 steps

Stage-Gated Product Incubation

Grow new products through five funded stages — wonder, explore, make, impact, scale — validating at each gate.

Strategy2 steps

Stop Churn Before It Happens

To stop churn, acquire customers who won't leave — churn is an acquisition problem, not a save problem.

Productivity4 steps

The $10 Game for Personal Priorities

Allocate a notional $10 across your priorities to expose where your time actually goes versus where it should.

The 10x Lens on New Ideas

For every promising idea, ask where it could go in 3-5 years if it were 10x bigger — and let that reshape it now.

The 20/80 Willingness-to-Pay Axiom

20% of what you build drives 80% of willingness to pay — and it's usually the easiest 20% to build.

The 30-Day Agent Training Loop

Ingest your docs, then correct the agent an hour a day for 30 days until it performs like your best rep.

Communication3 steps

The Ability-Trust-Appeal Relationship Model

Every professional relationship rests on ability, trust, and appeal; the experience you are matters most

Peak Performance3 steps

The Alpha-Beta-Gamma Focus Grid

Map brain-wave states against motivation systems and deliberately spend ~25% of your year outside busy beta

Marketing6 steps

The Ambassador Program Blueprint

Recruit the already-vocal, pay them in access not cash, and grow the cohort deliberately slowly

Sales5 steps

The A+ Middler and the Next Step

Founders are already elite at the middle of a sale — the only skill to add is never leaving a meeting without a next step.

The Atomic Unit of Sharing Test

Decide whether community-led growth will work for you before spending a dollar on it

Finance4 steps

The Attribution-Autonomy Pricing Matrix

Pick your AI pricing model by plotting value attribution against product autonomy, then climb toward outcome-based.

Strategy3 steps

The Believability Spectrum for Vision & Strategy

Every idea lands as believed, believable, conceivable, or inconceivable; your openness sets where the lines fall

The Better Tool, Same Problems Lens

Every model leap gets normalised within months — build for the boring future, not the euphoric one.

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

Self-Mastery3 steps

The Brain's Three Systems (Safety, Reward, Purpose)

Diagnose which of three motivational systems is driving someone's behavior before you try to change it

Strategy7 steps

The Carve-Out Cohort Turnaround

To fix a load-bearing product, secede from the metrics system with a small randomized cohort.

The Chief Agentic GTM Officer Play

Pick one painful problem, one leading vendor, and deploy an agent yourself—50 hours later you're hyper-employable.

The Coaching Model (Coaches, Not Managers)

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

The Coldly Rational Pivot Decision

Pivot only after you've exhausted the good ideas — and force emotional distance so the call is rational, not humiliating

The Community Form-Factor Matrix

A two-by-two that tells you which kind of community to build given your PMF and buyer

The Constrained-Resource Headcount Test

When the bottleneck isn't people, each new hire is a net productivity loss unless they uplevel everyone.

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 Durable Wrapper Test

Own a workflow you care about for a decade, then orchestrate 20 models beneath it

Finance5 steps

The Early-Stage Sales Comp Ramp

Pay 50/50, give away 100% of quarter-one bookings, then hold reps to closing 3-5x their take-home.

The First 30 Seconds Onboarding Bet

Earn the next 30 seconds by making one thing feel magical fast

Entrepreneurship5 steps

The First Growth Hire as Portfolio Manager

Hire acquisition first, and hire for attributes over channel expertise — expertise causes false precision

The Five Ingredients of a High-Performing Team

Clear goals + a why, results culture, team-first, ownership, and fun — in that order

The Forward-Deployed Engineer Vendor Column

Don't buy AI GTM tools on features—buy on who will actually get on the phone and deploy it with you.

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 GTM Agent Deployment Sequence

Roll out AI sales agents in the order of lowest effort and highest ROI: start with support, end with reactivation.

The Harder-to-Sell Heuristic

Only hire reps whose last product was harder to sell than yours — never easier.

The Incognito Cry Test

Go through your own product as an anonymous customer, find what makes you cry, and buy an agent to fix that.

The Introvert's Career Visibility Playbook

Five moves to get your value seen and your ambition known without becoming someone you're not

The Lead-Rich Audit

You don't need SaaStr's scale—count your website visitors and untouched CRM leads to see you're already lead-rich.

The Micro-Influencer Wide-Net Playbook

Skip the big creators; onboard thousands of trusted micro-influencers like teammates

Mindset3 steps

The Owner's Delusion (and the Audience's Illusion)

You overrate your own product because you built it; your users arrive distracted, barely-intending, and ready to bounce

Leadership3 steps

The Ownership Engine

Ownership is manufactured by scope design first, culture second, and leader accountability third

The Platform Encroachment Test

Build where the platform's mission says it will never go — the general layer is not yours to own.

Sales3 steps

The POC as Business Case

Frame every pilot as co-creating an ROI model, charge for it smartly, and never anchor the commercial deal.

The Prep-Call PM Interview Loop

Coach the candidate before their final presentation — how they use your feedback is the real signal

The Product People Spectrum: Innovators to Executors

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

The Proxy Goal Ladder

Every metric you chase is a proxy — climb the ladder to the mission before you optimise it.

The Sales Roadmap Budget

Give sales a fixed quarterly slice of the roadmap — say 10% of story points — and make them force-rank it.

The Same-Day Prototype Validation Loop

Idea in the morning, real users testing by afternoon, decision by evening

The Scrappy Wedge for Unglamorous Investment

Win backing for unsexy work by starting small, showing it visually, making it easy for others, and proving momentum.

Sales5 steps

The Sell-Me-This-App Interview

Make every sales candidate demo your actual product before you hire them — no exceptions.

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 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.

The Talent Development Lifecycle

Develop people across five stages: fit, ramp, early wins, visibility, lifelong relationship

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-Pillar AI Integration Model

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

Productivity3 steps

The Tomorrow Test for Saying No

Decide whether to accept a distant commitment by imagining you had to do it tomorrow

The Two-Bucket SEO Fit Test

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

The Two-Engine Profitable Growth Architect

Master market share and wallet share together — equal attention, not equal effort — to avoid the single-engine trap.

Self-Mastery3 steps

The Two-Question Introvert Diagnostic

Two thought experiments that reveal your true temperament preference, cutting through learned behavior

The Utility Curve

Use the S-curve of effort-to-value to decide whether a feature is under-invested or already maxed out

The VP of Free

Somebody must be the champion of the users who never pay — and it can only be product and the founders.

The Word-of-Mouth Machine PMF Test

Real product-market fit is organic pull, not award-winning launch spikes

Sales5 steps

The "Would I Buy From Them?" First-Rep Test

Hire your first two sales reps on one gut criterion: would you buy your own product from them?

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

Influence3 steps

Three Speeds of Influence + Choose Your Character

Pick an influence character that fits your personality, then choose slow, moderate, or fast based on the situation

Two-Reps-Then-VP (The 3-to-300 Rule)

Never hire a VP of Sales until two reps are hitting quota — and never hire one who won't carry a bag.

We Don't Sell Saddles Here (Sell the Outcome, Create the Market)

Don't sell the product — instill the yearning for what it makes possible, and build the market as you build the product

Leadership6 steps

We Might Be Wrong, But We Are Not Confused

Make being wrong cheap and being confused unacceptable, in both thought and execution.