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Oliver Buchannon
Jordan DiPietro
i’ll tell you all about it in a letter

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

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
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
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
Jordan DiPietro
When Growth Feels Stuck: Part 1

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
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
8 Predictions for 2026 — Plus: Proof-of-Life Marketing, AI Roles That Actually Matter, & Taste as a Moat

Jan 8, 2026

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9 min read

8 Predictions for 2026 — Plus: Proof-of-Life Marketing, AI Roles That Actually Matter, & Taste as a Moat

This week: Part 1 of my 2026 predictions, plus all the other great prediction-content I’ve read.

Jordan DiPietro
Jordan DiPietro
Before the Year Turns...

Dec 30, 2025

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3 min read

Before the Year Turns...

Lessons & reflections from the year that’s just about gone.

Jordan DiPietro
Jordan DiPietro
2025: The Year in Review

Dec 21, 2025

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18 min read

2025: The Year in Review

On identity, idle time, work, money, health, relationships, and the cost of getting it wrong.

Jordan DiPietro
Jordan DiPietro
Part 3: The Founder Attention Recession — Plus: Killing 1:1s, Fewer Meetings, and Better Decisions

Dec 18, 2025

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7 min read

Part 3: The Founder Attention Recession — Plus: Killing 1:1s, Fewer Meetings, and Better Decisions

This week: how founder availability quietly becomes the bottleneck, the GROW Report, and why structure beats responsiveness.

Jordan DiPietro
Jordan DiPietro
The Four Levels of Relationships

Dec 16, 2025

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7 min read

The Four Levels of Relationships

A simple framework for spotting relationships that compound vs. ones that don’t.

Jordan DiPietro
Jordan DiPietro
Killing 1:1s & The GROW Report

Dec 15, 2025

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4 min read

Killing 1:1s & The GROW Report

A simple operating system I used to move status updates out of meetings and into a weekly written report.

Jordan DiPietro
Jordan DiPietro
Part 2: The Founder Attention Recession — Plus: AI Funnels, Better Marketing Hires, and a Billionaire Maniac

Dec 11, 2025

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9 min read

Part 2: The Founder Attention Recession — Plus: AI Funnels, Better Marketing Hires, and a Billionaire Maniac

This week: the hard truth about your calendar, strategy vs. tactics, AI freemium lessons, and one wild founder story.

Jordan DiPietro
Jordan DiPietro
Good CEO // Bad CEO

Dec 5, 2025

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8 min read

Good CEO // Bad CEO

The early-stage playbook for leading in one of the earliest, highest-leverage chapter of your company’s story.

Jordan DiPietro
Jordan DiPietro
Part 1: The Founder Attention Recession — Plus: AI Reality Checks, Buffett’s 1972 Letter, and Offshore Talent Picks

Dec 4, 2025

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7 min read

Part 1: The Founder Attention Recession — Plus: AI Reality Checks, Buffett’s 1972 Letter, and Offshore Talent Picks

This week: the quiet tax on your brain, plus the AI dev-speed illusion, premium-brand lessons, and new hiring options.

Jordan DiPietro
Jordan DiPietro
Imposter Syndrome — Plus: North Star Metrics, Bromances, & a Wild Memoir

Nov 26, 2025

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7 min read

Imposter Syndrome — Plus: North Star Metrics, Bromances, & a Wild Memoir

This week: imposter thoughts vs syndrome, the best NSM guide, a legendary Scorsese bromance, and an unreal book rec.

Jordan DiPietro
Jordan DiPietro
Your AI Traffic is Moving (Quickly) —  Plus: Call Center SaaS, Scorigami, & Gen Z Reset

Nov 20, 2025

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7 min read

Your AI Traffic is Moving (Quickly) — Plus: Call Center SaaS, Scorigami, & Gen Z Reset

This week: where your future traffic is actually going, accent modification magic, weird NFL score patterns, and a call for National Service.

Jordan DiPietro
Jordan DiPietro
The New Front Door to the Internet: How AI Search Is Already Rewriting Your Traffic Strategy

Nov 18, 2025

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10 min read

The New Front Door to the Internet: How AI Search Is Already Rewriting Your Traffic Strategy

Search Is Changing Faster Than Most Companies Realize

Jordan DiPietro
Jordan DiPietro
How I Plan My Year (and the Tool You Should Steal)

Nov 15, 2025

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3 min read

How I Plan My Year (and the Tool You Should Steal)

Saturday Special: how to build a 2026 plan that actually ties goals to outcomes.

Jordan DiPietro
Jordan DiPietro
Inside the AI Bubble — Plus: Founder Hiring, a16z Books, & Health Hacks

Nov 13, 2025

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8 min read

Inside the AI Bubble — Plus: Founder Hiring, a16z Books, & Health Hacks

This week: breaking down the three kinds of AI bubbles, a smarter way to hire, what to read from a16z, and Justin Mares’ founder longevity list.

Jordan DiPietro
Jordan DiPietro
The Imposter Loop (and How to Break It)

Nov 11, 2025

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11 min read

The Imposter Loop (and How to Break It)

Imposter thoughts are normal. Imposter syndrome isn’t — here’s how to break the loop.

Jordan DiPietro
Jordan DiPietro
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