Jordan DiPietro

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

You Were the Operating System: How to Stop Being the Bottleneck as Your Company Grows

Sep 29, 2026

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11 min read

You Were the Operating System: How to Stop Being the Bottleneck as Your Company Grows

Direction, visibility, accountability, and cadence: the four systems that take over once the company outgrows you.

Jordan DiPietro

Two Days, Eight Execs, Everyone Ranked — Plus: AI-Proof Sales, Blankfein's Memoir, and Why Payday Is Dangerous

Sep 24, 2026

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4 min read

Two Days, Eight Execs, Everyone Ranked — Plus: AI-Proof Sales, Blankfein's Memoir, and Why Payday Is Dangerous

This week: the exec-room ritual GM and Meta are missing, what AI can't do in a sales call, and the line about success you'll want to steal

Jordan DiPietro

One Job, 100 Fake Applicants — Plus: Zuck Domination, the AI Trust Rule, and Why Flying Sucks

Sep 17, 2026

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4 min read

One Job, 100 Fake Applicants — Plus: Zuck Domination, the AI Trust Rule, and Why Flying Sucks

This week: the three things a bot still can't fake, a 30-minute Zuck profile, and a rule for when to trust AI

Jordan DiPietro

Sep 10, 2026

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5 min read

How to Lose $224 Billion Without Doing Anything Dumb — Plus: offline brand inspo, a full agent stack, and quiet PMF erosion

This week: what actually killed Nike, touching grass for brand ideas, one rep's entire bot setup, and how PMF slips away

Jordan DiPietro

Hire the Kids for God's Sake — Plus: the 20-deal sales test, Ozempic's grocery effect, and the consumer trade-down

Sep 3, 2026

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5 min read

Hire the Kids for God's Sake — Plus: the 20-deal sales test, Ozempic's grocery effect, and the consumer trade-down

This week: the entry-level job is collapsing and why that's your hiring edge, a 20-deal sales gut-check, the great consumer trade-down, and how Ozempic is shrinking the grocery bill

Jordan DiPietro

Is Writing a Boomer Move? — Plus: my open-rate disaster, Lovable's design bet, and a million AI slop reports

Aug 27, 2026

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5 min read

Is Writing a Boomer Move? — Plus: my open-rate disaster, Lovable's design bet, and a million AI slop reports

This week: why the format of your team updates matters more than you think, Lovable's design playbook, Hiten Shah on taste, and LinkedIn's slop button

Jordan DiPietro

What's Your Company's MPH? — Plus: Obama's summer reads, Buffett's newspaper test, and the risky career call

Aug 20, 2026

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4 min read

What's Your Company's MPH? — Plus: Obama's summer reads, Buffett's newspaper test, and the risky career call

This week: how CEOs actually build urgency, Obama's summer list, Buffett's integrity filter, and the job you weren't supposed to take

Jordan DiPietro

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

Jordan DiPietro

You Were the Operating System: How to Stop Being the Bottleneck as Your Company Grows

Two Days, Eight Execs, Everyone Ranked — Plus: AI-Proof Sales, Blankfein's Memoir, and Why Payday Is Dangerous

One Job, 100 Fake Applicants — Plus: Zuck Domination, the AI Trust Rule, and Why Flying Sucks

How to Lose $224 Billion Without Doing Anything Dumb — Plus: offline brand inspo, a full agent stack, and quiet PMF erosion

Hire the Kids for God's Sake — Plus: the 20-deal sales test, Ozempic's grocery effect, and the consumer trade-down

Is Writing a Boomer Move? — Plus: my open-rate disaster, Lovable's design bet, and a million AI slop reports

What's Your Company's MPH? — Plus: Obama's summer reads, Buffett's newspaper test, and the risky career call

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

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