Jordan DiPietro

D.R.E.A.M. (Distribution Rules Everything Around Me) — Plus: GSC hack, Goldman’s take on AI panic, and Adam Silver's NBA

Jun 11, 2026

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4 min read

D.R.E.A.M. (Distribution Rules Everything Around Me) — Plus: GSC hack, Goldman’s take on AI panic, and Adam Silver's NBA

This week: why everyone's shipping and nothings’ getting used, plus a GA hack worth stealing, why the NBA keeps getting worse, and Goldman's AI jobs take

Jordan DiPietro

Would your customers actually miss you? — Plus: the AI tool that cost a founder a deal, Anthropic's shot at #1, and the $100K hiring mistake

Jun 4, 2026

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5 min read

Would your customers actually miss you? — Plus: the AI tool that cost a founder a deal, Anthropic's shot at #1, and the $100K hiring mistake

This week: what actually survives the AI wave, the market doing the impossible, and why you should check your AI permissions before they cost you

Jordan DiPietro

The Most Expensive “Reflex” — Plus: 3 ways your team could be dropping the ball, Lenny’s latest 10 takeaways, and an (old) but good Anthropic interview.

May 28, 2026

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4 min read

The Most Expensive “Reflex” — Plus: 3 ways your team could be dropping the ball, Lenny’s latest 10 takeaways, and an (old) but good Anthropic interview.

This week: at least one of the major questions to ask before opening a job req, plus Paul Stansik on the inevitable dropped ball, and a recent Lenny’s interview on AI and automation.

Jordan DiPietro

Higher Prices, But Fewer People — Plus: my AI-powered site design, working capital wizardry, and a hidden YouTube hack

May 21, 2026

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3 min read

Higher Prices, But Fewer People — Plus: my AI-powered site design, working capital wizardry, and a hidden YouTube hack

This week: when growing revenue masks a dying business, a CFO money trick most founders miss, Gemini's YouTube cheat code, and the vertical AI moment

Jordan DiPietro

I Redesigned My Entire Website in Cowork. Here's How.

May 18, 2026

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4 min read

I Redesigned My Entire Website in Cowork. Here's How.

8 pillar pages, 5 versions deep, zero agency fees. A walkthrough of the design process.

Jordan DiPietro

Starbucks Preserved Dollars Longer Than It Preserved Affinity

May 18, 2026

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4 min read

Starbucks Preserved Dollars Longer Than It Preserved Affinity

How a Fortune 500 brand can be bleeding out while the top line still looks fine.

Jordan DiPietro

Business

Founder Mode Got Hijacked — Plus: a Content Engine, the AI Polish Problem, and Ted Turner

May 14, 2026

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4 min read

Founder Mode Got Hijacked — Plus: a Content Engine, the AI Polish Problem, and Ted Turner

This week: the one habit that fixes accountability, the AI labor piece everyone's talking about, and what USA Hockey can teach you about hiring.

Jordan DiPietro

This is what you keep flinching from — Plus: a worksheet, the case for AI fatigue, and the outbound data stack

May 7, 2026

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5 min read

This is what you keep flinching from — Plus: a worksheet, the case for AI fatigue, and the outbound data stack

This week: why your plateau is a capacity problem, a 20-minute worksheet that names the tension, Kieran Flanagan on AI fatigue, and the lottery of career success.

Jordan DiPietro

Apr 30, 2026

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5 min read

Your Brand’s Sharp, Product’s Fuzzy — Plus: YC's next big bets, an AI gut-check, and Fab Five Freddy

This week: why your brand promise isn't your product, YC's next big bets, an AI gut-check, and a Fab Five Freddy deep dive

Jordan DiPietro

The Real Way to Fix Churn — Plus: Marketing Skills for Claude, Hiring "Barrels," and Raising Outdoor Kids

Apr 23, 2026

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6 min read

The Real Way to Fix Churn — Plus: Marketing Skills for Claude, Hiring "Barrels," and Raising Outdoor Kids

This week: why your renewal strategy is pointed at the wrong month, marketing skills for Claude, hiring "barrels," and raising outdoor kids

Jordan DiPietro

Stop Feeding Dead Channels — Plus: Engineering ROI, the NYT Playbook, and SNL’s Creator

Apr 16, 2026

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8 min read

Stop Feeding Dead Channels — Plus: Engineering ROI, the NYT Playbook, and SNL’s Creator

This week: why your marketing channels are dying, software team ROI, NYT's subscription machine, and Lorne Michaels as a leader.

Jordan DiPietro

The $10 Billion Power of "No" — Plus: WHOOP & Will Ahmed, a 10-second AI Hack, and a Lesson in Market Crashes.

Apr 9, 2026

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8 min read

The $10 Billion Power of "No" — Plus: WHOOP & Will Ahmed, a 10-second AI Hack, and a Lesson in Market Crashes.

This week: what WHOOP got right by ignoring its users, a Claude skill worth installing, and the great market crash of 1907.

Jordan DiPietro

How the F*ck Do You Keep Up With AI? (Special Edition)

Apr 2, 2026

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6 min read

How the F*ck Do You Keep Up With AI? (Special Edition)

This week: a special edition on the only AI strategy that actually works

Jordan DiPietro

Don't Let the Org Just Happen — Plus: People vs. Performance Culture, Clay's Pricing Overhaul, and a Great Pod Listen

Mar 26, 2026

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9 min read

Don't Let the Org Just Happen — Plus: People vs. Performance Culture, Clay's Pricing Overhaul, and a Great Pod Listen

This week: why your team structure is an accident, the 3H leadership framework, Clay's pricing overhaul, and reading human potential.

Jordan DiPietro

You Already Know What to Do — Plus: AI-Native Orgs, Josh Waitzkin, and Tom Freston's Wild Ride

Mar 19, 2026

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8 min read

You Already Know What to Do — Plus: AI-Native Orgs, Josh Waitzkin, and Tom Freston's Wild Ride

This week: why founders stall on calls they already know the answer to, how AI-native companies actually operate, and a few things worth your time.

Jordan DiPietro

Mar 18, 2026

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7 min read

i’ll tell you all about it in a letter

We got faster at talking, and maybe a bit worse at saying the things that matter.

Jordan DiPietro

Stop Being Scared of Big Bets — Plus: Real Moats, Founder Handoffs, and a Parenting Hot Take

Mar 12, 2026

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9 min read

Stop Being Scared of Big Bets — Plus: Real Moats, Founder Handoffs, and a Parenting Hot Take

This week: the expected value equation, a super short head start, and a parenting take that's going to start some arguments

Jordan DiPietro

Most Founders Think They're Product-First. They're Not. — Plus: Agent to Agent, Metrics that Lie, and Closing the 37 Tabs

Mar 5, 2026

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8 min read

Most Founders Think They're Product-First. They're Not. — Plus: Agent to Agent, Metrics that Lie, and Closing the 37 Tabs

This week: the product vs. funnel identity crisis, why your metrics are making you miserable, thinking in agents, and closing the damn tabs.

Jordan DiPietro

The Babysitter Founder — Plus: AI Jobs, USA Hockey, & Chesky’s AI Hot Take

Feb 26, 2026

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8 min read

The Babysitter Founder — Plus: AI Jobs, USA Hockey, & Chesky’s AI Hot Take

This week: the one habit that fixes accountability, the AI labor piece everyone's talking about, and what USA Hockey can teach you about hiring.

Jordan DiPietro

“Holy Sh*t, I Hope I’m Right.” — Plus: AI’s Most Read Essay, Ovitz Unfiltered, & Housing Data

Feb 19, 2026

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8 min read

“Holy Sh*t, I Hope I’m Right.” — Plus: AI’s Most Read Essay, Ovitz Unfiltered, & Housing Data

This week: the belief tax of leadership, AI’s scariest essay, Ovitz on relationships, and what’s actually broken in housing.

Jordan DiPietro

Feb 12, 2026

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8 min read

You Can Just Build Things — Plus: AI Ads, Cancel Flows, & Why Sports Betting Can’t be Harmless

This week: AI ads go mainstream, what cancel flows actually reveal, and why sports betting isn’t the harmless habit we pretend it is.

Jordan DiPietro

When Growth Feels Stuck: Part 3 — Plus, Churn Reality, the AG1 Drama, & Granola AI

Feb 5, 2026

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7 min read

When Growth Feels Stuck: Part 3 — Plus, Churn Reality, the AG1 Drama, & Granola AI

This week: the leaky bucket killing growth, some uncomfortable retention math, AG1 getting exposed, and a surprisingly useful AI notes tool.

Jordan DiPietro

When Growth Feels Stuck: Part 2 — Plus, Why Channels Stall, Growth Breakouts, & a Reading List Worth Your Time

Jan 29, 2026

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11 min read

When Growth Feels Stuck: Part 2 — Plus, Why Channels Stall, Growth Breakouts, & a Reading List Worth Your Time

This week: growth plateaus, discovery before distraction, growth models that actually matter, and a reading list to dive into.

Jordan DiPietro

Jan 22, 2026

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11 min read

When Growth Feels Stuck: Part 1

This week: when growth stalls, AI-hacking purchase intent, and why Rick Rubin is the man.

Jordan DiPietro

8 Predictions for 2026 (Part 2) — Plus: Focus, Leaky Buckets, and AEO

Jan 15, 2026

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11 min read

8 Predictions for 2026 (Part 2) — Plus: Focus, Leaky Buckets, and AEO

This week: Part 2 of my 2026 predictions—focus, retention, data ownership, and authority.

Jordan DiPietro

Jordan DiPietro

D.R.E.A.M. (Distribution Rules Everything Around Me) — Plus: GSC hack, Goldman’s take on AI panic, and Adam Silver's NBA

Would your customers actually miss you? — Plus: the AI tool that cost a founder a deal, Anthropic's shot at #1, and the $100K hiring mistake

The Most Expensive “Reflex” — Plus: 3 ways your team could be dropping the ball, Lenny’s latest 10 takeaways, and an (old) but good Anthropic interview.

Higher Prices, But Fewer People — Plus: my AI-powered site design, working capital wizardry, and a hidden YouTube hack

I Redesigned My Entire Website in Cowork. Here's How.

Starbucks Preserved Dollars Longer Than It Preserved Affinity

Founder Mode Got Hijacked — Plus: a Content Engine, the AI Polish Problem, and Ted Turner

This is what you keep flinching from — Plus: a worksheet, the case for AI fatigue, and the outbound data stack

Your Brand’s Sharp, Product’s Fuzzy — Plus: YC's next big bets, an AI gut-check, and Fab Five Freddy

The Real Way to Fix Churn — Plus: Marketing Skills for Claude, Hiring "Barrels," and Raising Outdoor Kids

Stop Feeding Dead Channels — Plus: Engineering ROI, the NYT Playbook, and SNL’s Creator

The $10 Billion Power of "No" — Plus: WHOOP & Will Ahmed, a 10-second AI Hack, and a Lesson in Market Crashes.

How the F*ck Do You Keep Up With AI? (Special Edition)

Don't Let the Org Just Happen — Plus: People vs. Performance Culture, Clay's Pricing Overhaul, and a Great Pod Listen

You Already Know What to Do — Plus: AI-Native Orgs, Josh Waitzkin, and Tom Freston's Wild Ride

i’ll tell you all about it in a letter

Stop Being Scared of Big Bets — Plus: Real Moats, Founder Handoffs, and a Parenting Hot Take

Most Founders Think They're Product-First. They're Not. — Plus: Agent to Agent, Metrics that Lie, and Closing the 37 Tabs

The Babysitter Founder — Plus: AI Jobs, USA Hockey, & Chesky’s AI Hot Take

“Holy Sh*t, I Hope I’m Right.” — Plus: AI’s Most Read Essay, Ovitz Unfiltered, & Housing Data

You Can Just Build Things — Plus: AI Ads, Cancel Flows, & Why Sports Betting Can’t be Harmless

When Growth Feels Stuck: Part 3 — Plus, Churn Reality, the AG1 Drama, & Granola AI

When Growth Feels Stuck: Part 2 — Plus, Why Channels Stall, Growth Breakouts, & a Reading List Worth Your Time

When Growth Feels Stuck: Part 1

8 Predictions for 2026 (Part 2) — Plus: Focus, Leaky Buckets, and AEO

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