Jordan DiPietro

Former CEO of The Hustle and Hampton. Founder coach, advisor, and creator of Hiring OS.

Airtable Sold for 89% Off. That's Good News for You — Plus: AI pricing and heat-seeking missiles.

Aug 13, 2026

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4 min read

Airtable Sold for 89% Off. That's Good News for You — Plus: AI pricing and heat-seeking missiles.

This week: what Airtable's fire sale actually means for profitable founders, the internet running out of training data, the hire who hunts pain, and how to price in the AI age.

Jordan DiPietro

Is AI Going to Recommend You? — Plus: death of the follower, WFH, and superintelligence

Aug 6, 2026

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5 min read

Is AI Going to Recommend You? — Plus: death of the follower, WFH, and superintelligence

This week: the gap between AI knowing you and AI recommending you, the death of the follower, and the WFH data is finally in.

Jordan DiPietro

Business

CEO Coaching for Bootstrapped Founders Doing $5M–$50M

Aug 4, 2026

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6 min read

CEO Coaching for Bootstrapped Founders Doing $5M–$50M

A coach for profitable, founder-owned companies, not venture-backed startups burning toward a Series B.

Jordan DiPietro

When to Hire a COO (and Why It's Usually Later Than You Think)

Aug 3, 2026

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8 min read

When to Hire a COO (and Why It's Usually Later Than You Think)

Most founders reach for a COO to escape operational chaos. That's the wrong reason. When to hire a COO, what it costs, and the ladder to climb first.

Jordan DiPietro

How to Hire a Salesperson Who Can Actually Sell (Not Just Interview Well)

Aug 3, 2026

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6 min read

How to Hire a Salesperson Who Can Actually Sell (Not Just Interview Well)

Salespeople are professionally good at interviews. That's the trap. The founder's system for hiring a salesperson who can actually sell. Free frameworks.

Jordan DiPietro

How to Hire Employees for a Small Business: The Founder's System

Aug 3, 2026

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6 min read

How to Hire Employees for a Small Business: The Founder's System

How to hire employees for a small business when referrals keep failing you: sourcing, the 3-minute video filter, work samples, and scorecards. Free system.

Jordan DiPietro

How to Hire Your First Employee (Without a Recruiter)

Aug 3, 2026

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6 min read

How to Hire Your First Employee (Without a Recruiter)

The complete sequence for hiring your first employee: role definition, legal setup, interviews, and offer. No recruiter, no HR department, no guesswork.

Jordan DiPietro

The Rent Comes Due — Plus: Opus 5's real leap, team burnout, and Iger's decade of dealmaking

Jul 30, 2026

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4 min read

The Rent Comes Due — Plus: Opus 5's real leap, team burnout, and Iger's decade of dealmaking

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

9 Hiring Mistakes Founders Keep Making (and the System That Prevents Them)

Jul 29, 2026

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7 min read

9 Hiring Mistakes Founders Keep Making (and the System That Prevents Them)

The 9 common hiring mistakes founders repeat, and the process fix for each. From 20+ years of hiring at Motley Fool, The Hustle, HubSpot, and Hampton. Free system inside.

Jordan DiPietro

"What Are Your Thoughts?"— Plus: AI loops, losing product-market fit, and a book-list hack

Jul 23, 2026

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5 min read

"What Are Your Thoughts?"— Plus: AI loops, losing product-market fit, and a book-list hack

This week: the soft close, stop prompting and start looping, how companies quietly lose PMF, and never adding a dud book again.

Jordan DiPietro

The Trait No Interview Can Catch — Plus: Paying for AI Twice, Agents Writing Uber's Code, and a Century of Stock Returns

Jul 16, 2026

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4 min read

The Trait No Interview Can Catch — Plus: Paying for AI Twice, Agents Writing Uber's Code, and a Century of Stock Returns

This week: the three signals that separate a real finisher from a great talker, plus I'm officially opening up hiring help for your next senior leader.

Jordan DiPietro

Your Best People Are "Barrels" — Plus: When to Skip the CFO, a Great Bookkeeping Option, and AI's Candor Problem

Jul 9, 2026

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4 min read

Your Best People Are "Barrels" — Plus: When to Skip the CFO, a Great Bookkeeping Option, and AI's Candor Problem

This week: what separates a 4-person team from a 40-person one, when to hire a finance leader vs. a bookkeeper, and the AI-recording era.

Jordan DiPietro

American Turns 250 — Is the Dream Still Alive?

Jul 2, 2026

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4 min read

American Turns 250 — Is the Dream Still Alive?

This week: a special 250th edition, what the data says about the dream, two great reads and an incredible 6-part podcast about America today.

Jordan DiPietro

Was the American Dream Ever Just About Money?

Jun 28, 2026

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9 min read

Was the American Dream Ever Just About Money?

Before the 250th birthday cake, an honest question about the celebration.

Jordan DiPietro

Business

The Pricing Model That's Breaking — Plus: Stanford Negotiation Hack, AI Adoption, and Gavin Baker on the Chip Race

Jun 25, 2026

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4 min read

The Pricing Model That's Breaking — Plus: Stanford Negotiation Hack, AI Adoption, and Gavin Baker on the Chip Race

This week: why flat fees are quietly becoming a liability, a Stanford negotiation shortcut, how AI adoption shakes out inside big companies, and an investor making the chip buildout feel obvious

Jordan DiPietro

Buried in Slack? Your team needs clarity. — Plus: Google's new AI search report, finding the truth, and a Booker-shortlisted novel

Jun 18, 2026

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4 min read

Buried in Slack? Your team needs clarity. — Plus: Google's new AI search report, finding the truth, and a Booker-shortlisted novel

Why firefighting feels productive and never is, plus a deep soul song that should've made its singer famous.

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

Jordan DiPietro

Airtable Sold for 89% Off. That's Good News for You — Plus: AI pricing and heat-seeking missiles.

Is AI Going to Recommend You? — Plus: death of the follower, WFH, and superintelligence

CEO Coaching for Bootstrapped Founders Doing $5M–$50M

When to Hire a COO (and Why It's Usually Later Than You Think)

How to Hire a Salesperson Who Can Actually Sell (Not Just Interview Well)

How to Hire Employees for a Small Business: The Founder's System

How to Hire Your First Employee (Without a Recruiter)

The Rent Comes Due — Plus: Opus 5's real leap, team burnout, and Iger's decade of dealmaking

9 Hiring Mistakes Founders Keep Making (and the System That Prevents Them)

"What Are Your Thoughts?"— Plus: AI loops, losing product-market fit, and a book-list hack

The Trait No Interview Can Catch — Plus: Paying for AI Twice, Agents Writing Uber's Code, and a Century of Stock Returns

Your Best People Are "Barrels" — Plus: When to Skip the CFO, a Great Bookkeeping Option, and AI's Candor Problem

American Turns 250 — Is the Dream Still Alive?

Was the American Dream Ever Just About Money?

The Pricing Model That's Breaking — Plus: Stanford Negotiation Hack, AI Adoption, and Gavin Baker on the Chip Race

Buried in Slack? Your team needs clarity. — Plus: Google's new AI search report, finding the truth, and a Booker-shortlisted novel

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

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