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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
Efficiency’s Dirty Secret — Plus: App-Level GPT Hacks, Resiliency, & BI’s new AI Byline

Nov 6, 2025

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7 min read

Efficiency’s Dirty Secret — Plus: App-Level GPT Hacks, Resiliency, & BI’s new AI Byline

This week: what founders get wrong about efficiency, the best new GPT tricks, and a newsroom run by bots.

Jordan DiPietro
Jordan DiPietro
Burnout Isn’t About the Hours — Plus: My Take on Luck, Sales Call Gold, & Money Incentives

Oct 30, 2025

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8 min read

Burnout Isn’t About the Hours — Plus: My Take on Luck, Sales Call Gold, & Money Incentives

This week: why burnout’s about connection, not capacity, sales insights, & Semafor’s strategy

Jordan DiPietro
Jordan DiPietro
Lottery + Leverage: A Simple Formula for Designing Your Own Luck

Oct 26, 2025

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9 min read

Lottery + Leverage: A Simple Formula for Designing Your Own Luck

A personal take on privilege, preparation, and the strange math between luck and leverage

Jordan DiPietro
Jordan DiPietro
Breaking the $10M Ceiling — Plus: AI ā€œBubbleā€ Myths & Platform Playbooks

Oct 23, 2025

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8 min read

Breaking the $10M Ceiling — Plus: AI ā€œBubbleā€ Myths & Platform Playbooks

This week: how service-led founders hit $10M ARR, why AI isn’t a bubble, and my key takeaways from reading Platform Revolution (building leverage through networks).

Jordan DiPietro
Jordan DiPietro
Platform Revolution: Notes, Takeaways, and Applications

Oct 19, 2025

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8 min read

Platform Revolution: Notes, Takeaways, and Applications

Discover how leading platforms leverage network effects, modular design, and governance rules.

Jordan DiPietro
Jordan DiPietro
Founder Planning, Part 2 — From Forecast to Focus to Follow-Through

Oct 16, 2025

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8 min read

Founder Planning, Part 2 — From Forecast to Focus to Follow-Through

This week: how to make your plan move — plus AEO hacks, AI fever dreams, and Sora’s surge

Jordan DiPietro
Jordan DiPietro
Founder Planning, Part 1 — From Vision to Forecast to Budget

Oct 9, 2025

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8 min read

Founder Planning, Part 1 — From Vision to Forecast to Budget

This week: how founders plan smarter — plus Hinkie, Walling, and the 5% rule.

Jordan DiPietro
Jordan DiPietro
Sunday Special: 7 Growth Traps That Wreck Founders — and How to Escape Them All

Oct 5, 2025

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4 min read

Sunday Special: 7 Growth Traps That Wreck Founders — and How to Escape Them All

A $8.5B takedown turned into a founder’s playbook you’ll actually use

Jordan DiPietro
Jordan DiPietro
Saying No as CEO -- Plus: downsells that work, instant checkout, & Horowitz unfiltered

Oct 2, 2025

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7 min read

Saying No as CEO -- Plus: downsells that work, instant checkout, & Horowitz unfiltered

This week: startup discipline, field notes on long sales cycles, and shopping in ChatGPT

Jordan DiPietro
Jordan DiPietro
The 3R Framework: Downsells for Long Sales Cycles

Sep 29, 2025

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6 min read

The 3R Framework: Downsells for Long Sales Cycles

Turning lost deals into entry ramps for bigger wins

Jordan DiPietro
Jordan DiPietro
New Moats for Founders — Plus: Copy.ai’s 10M Users, AI’s Next Wave, and Audience → Community

Sep 25, 2025

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7 min read

New Moats for Founders — Plus: Copy.ai’s 10M Users, AI’s Next Wave, and Audience → Community

This week: data, distribution, & depth — Copy.ai’s 10M playbook, AI’s future, and the shift from audience to community.

Jordan DiPietro
Jordan DiPietro
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