LLenny's Podcast
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Innovation3 steps

Backcasting & Reject the Premise

Stand in the future you designed and look back — don't forecast forward from today's constraints.

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Mindset3 steps

Bob the Monster and the Two-Week Rule

Externalize the emotions of change into a monster, let it rage, and only act on what survives two weeks.

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Strategy4 steps

Category Design: Create Demand vs. Capture Demand

Design your own market category instead of competing for a slice of someone else's.

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Leadership4 steps

Commit-and-Celebrate Weekly Cadence

Bookend every week with Monday commitments and Friday celebrations, tracked by a short weekly status.

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Marketing4 steps

Copy Comps' Zero-to-One, Not Their Growth Hacking

Ignore late-stage growth tactics with no users — study what your archetype did to get its first 1,000

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Communication5 steps

Cross-Subgraph Resonance Testing (Metaphor Forging)

Test framings live across unconnected audiences; the ones that land in distant subgraphs will travel.

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Strategy3 steps

Damming the Demand

Compete category-to-category against the status quo, never product-to-product against a rival.

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Communication4 steps

Design For Tomorrow's Majority, Not The Vocal Minority

Optimize for the far larger future user base, then manage the unhappy few with authentic listening.

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Strategy3 steps

Differentiate Above The Model, Not Around Its Gaps

Build your moat outside the LLM so your product gets better as the models get better.

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Leadership3 steps

Earn The Next Role By Driving Impact In This One

Stop eyeing the next promotion; be judged on impact delivered in the job you already hold.

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Self-Mastery5 steps

Follow People, Not Plans

Choose jobs by who you'll learn from, not by a five-year plan or a financial bet.

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Marketing4 steps

Frame, Name, Claim the Problem (Languaging & Point of View)

Use new language to reframe a problem so people see it differently and want a new solution.

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Strategy5 steps

Gardening Over Building (Farming for Miracles)

Plant many cheap compounding seeds instead of manufacturing outcomes with brute effort.

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Leadership3 steps

Give Away Your Legos

In a scaling company, repeatedly hand off what you're good at to keep climbing the growing pile.

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Productivity3 steps

Grade for Learning, Not Precision

Hand-wave the OKR score; spend your energy on the retrospective 'why' behind it.

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Communication4 steps

Hook-Middle-End Story Structure

Package your message as a story with a hook, a middle that hides the message, and a celebratory end — then ask how to make it better.

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Innovation3 steps

Information-Diet Idea Divergence

Same inputs produce same ideas — mine your unique experience and starve the herd feed

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Leadership3 steps

Invest in High Performers by Running Experiments

Stop babysitting low performers; grow your best people by testing theories about their potential.

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Self-Mastery4 steps

J-Curve vs. Stairs Career Growth

Jump off career cliffs into jobs you're unqualified for; fall for 6-9 months, then climb far beyond the stairs.

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Marketing5 steps

Lightning Strike Go-to-Market (Supers, POV & Word of Mouth)

Concentrate firepower on super consumers with a reframing POV to ignite word of mouth.

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Leadership5 steps

Organizational Kayfabe

Diagnose the shared fiction everyone knows is false — then route around it without detonating it.

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Leadership4 steps

Pilot-With-Your-Best-Team Rollout

Don't roll OKRs out company-wide; hand the book to your strongest team, let them adapt it, then spread by twos.

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Self-Mastery5 steps

Play Yourself Like a Fiddle (Activation Energy + Always-Rules)

Beat activation energy with tight time boxes and an escalating task ladder; hold habits with always-rules.

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Entrepreneurship3 steps

Pre-Sell Before You Build

Do customer validation and line up buyers before writing code or raising money

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Leadership3 steps

Serve the Business, Not the People

Strip emotion out of hard calls by asking what you'd do if the person had no negative reaction.

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Strategy6 steps

Six Rules for Goals and Alignment

Goals are a communication tool: three max, one that wins, intern-legible, painful, single-owned, and followed up.

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Leadership4 steps

Slime Mold Org Design (Sports Car vs Big Rig)

Coordination cost grows with the square of headcount — drive the vehicle you actually have.

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Innovation6 steps

Strategy Salons (Nerd Clubs)

Seed a small, opt-in, yes-and idea group that spins off strategy insights as a side effect.

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Leadership4 steps

Superpower Naming (Be More, Not Different)

Name someone's superpower early, then frame every nudge as 'be more' rather than 'be different'.

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Innovation2 steps

Tar Pit Idea Detection

Spot the seductive ideas that draw everyone in and trap them — they validate but never work

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Leadership4 steps

The 70/30 Cover Fire Allocation

Spend 70% earning the right to exist so the other 30% can plant seeds nobody will kill.

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Strategy5 steps

The Adjacent Possible + Low-Resolution North Star

Take only safe next steps — but always the one with the steepest gradient toward a 3-5 year North Star.

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Marketing3 steps

The Better Trap

A 'better' copy of an existing solution to a well-understood problem almost always fails.

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Productivity5 steps

The Bits and Bobs Idea Distillation Loop

Capture everything, filter weekly by resonance, distil, publish — a compounding personal insight engine.

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Sales3 steps

The Calendar Customer-Contact Audit

20-30% of your calendar should say 'customer meeting' — in person, not behind a keyboard

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Sales3 steps

The Collison Install (Last-Mile Close)

A 'yes' isn't a sale — hand-hold implementation until the customer is fully live

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Entrepreneurship3 steps

The Don't-Die Keep-Going / Give-Up Decision

Deciding whether to persist or shut down by testing love, energy, and remaining moves

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Strategy3 steps

The 'Going Home' Pivot

A good pivot moves warmer — toward your existing expertise and what your last idea taught you

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Entrepreneurship3 steps

The Hated-Incumbent Idea Prompt

Find a big incumbent customers hate with terrible software, then build the replacement

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Strategy2 steps

The Ideas-Left Pivot Timing Test

Pivot when you're out of credible growth ideas, not just because growth is slow

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Strategy4 steps

The Mission-to-Monday Cascade

Translate a 5-year mission down through strategy and quarterly OKRs into what you actually do this week.

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Leadership6 steps

The PM-Engineering Alignment Operating System

Run product and engineering as one leadership unit with clear ownership and async, iterated reviews.

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Leadership3 steps

The Three-Peer 24-Hour Approval

Replace slow top-down OKR sign-off with three peers who sanity-check your goals in a 24-hour turnaround.

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Leadership4 steps

The Waterline Model (Snorkel Before You Scuba)

Diagnose team problems from the top down: structure and dynamics, not the people, cause 80% of issues.

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Innovation4 steps

Throwaway Prototyping To Discover The Product

Build disposable prototypes on real data to feel what works before writing any production code.

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Strategy4 steps

Triangulated Key Results

Measure one quarterly objective from three angles — a hard number, a squishy quality metric, and a dollar figure.

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Productivity4 steps

Use AI As Leverage On Your PM Time

Assign the model a role, feed it more context than you could read, and iterate the prompt until it works.

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