LLenny's Podcast
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Cash App

By Block, Inc.

1 recommend/use · 5 sourced episodes

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Artifact Reverse-Engineering and Backstage Observation

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

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Code Quality Doesn't Equal Product Success

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Conway's Law Reorg: Go Functional Before You Go AI

Restructure engineering into one functional org before expecting company-wide AI or technical depth

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Discover Pain by Watching, Not Asking

Find the real intensity of a problem by watching people work, because they can't self-report it

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Don't Stop Until You Reach the End

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Drive AI Adoption By Using It Yourself On A Real Problem

Executives using the tool daily on their own real problems beats any top-down mandate or think-piece

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Engineering Honest Feedback

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Hire the People That People Pick

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Hypothesis-Based Coaching (Explorer, Not Lecturer)

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Make the Implicit Explicit (Meetings and Decisions)

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Self-Mastery6 steps

Outcome-Backwards Skill Acquisition

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Personal Operating Principles Discovery

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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.

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Progress Cadence as the Success Signal

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Question the Base Assumption Before Build-or-Buy

Before building OR buying a tool, ask whether the process needs to exist at all

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Ride the AI Value Wave

Treat today's AI capability as the worst it will ever be and expand where it's most efficacious

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Say the Thing You Think You Cannot Say

Voice the hard observation by detoxifying it into a question you own

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Entrepreneurship3 steps

Start Small, Don't Boil the Ocean

Narrow scope to the achievable thing in front of you, then build momentum on top of it

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Startup-Within-a-Company Team Design

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The Company Operating System (House Metaphor)

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The Differentiation Stack

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The Early-Adopter Rejection Math

Reframe customer outreach: reach 10 to find 1, and indifference isn't rejection

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Self-Mastery4 steps

The Fish-and-Water Strength Test

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

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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.

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The Smallest-Ask Mentor Ladder

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

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The "What's Holding You Back" Office Hour

Replace status updates with one question that surfaces the single true bottleneck

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Tuning Your Operating Cadence

Set review rhythm by two signals: too fast if no progress, too slow if content is stale

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Value the Technical Co-Founder

Why engineering is the hard part, and how a non-technical founder should actually treat it

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