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Jason Jackson
Jason Jackson

Jason helps founders scale companies. 20+ years leading product and ops at high-growth startups.

Which part of your product is expensive?

Sep 23, 2026

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7 min read

Which part of your product is expensive?

ICONIQ found AI companies doing fine on 55% gross margins. It also found them growing 900% a year. One of those numbers is a lot easier to copy than the other.

Jason Jackson
Jason Jackson
When a fake hire reaches payroll

Sep 16, 2026

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8 min read

When a fake hire reaches payroll

A fake candidate can make it through your hiring process without creating a sanctions violation. The real problem begins when you start paying them.

Jason Jackson
Jason Jackson
What your customer needs by month six

Sep 9, 2026

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6 min read

What your customer needs by month six

Buyers expect a return within six months of buying, however long the contract runs.

Jason Jackson
Jason Jackson
The losing version

Sep 2, 2026

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6 min read

The losing version

Oregon ran a sign-up experiment that looked terrible on day one. Four months later, the losing version had produced 18% more of the behavior Oregon actually wanted.

Jason Jackson
Jason Jackson
It's not me, it's you.

Aug 26, 2026

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5 min read

It's not me, it's you.

ServiceTitan dumped a nine-year partner by email. The partner found out when the customers did.

Jason Jackson
Jason Jackson
Your team knows which client I mean

Aug 19, 2026

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9 min read

Your team knows which client I mean

The paying client your team dreads is costing you quality and people.

Jason Jackson
Jason Jackson
The habits that hid a $115 million fraud

Aug 12, 2026

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7 min read

The habits that hid a $115 million fraud

Twelve founders went to prison for fraud. The court files read like an ordinary work week.

Jason Jackson
Jason Jackson

Founder bottleneck

The sixth day

Aug 5, 2026

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8 min read

The sixth day

Tech's loudest investors are demanding six-day weeks. The country that invented the schedule outlawed it, and the man who built the five-day week did it for output.

Jason Jackson
Jason Jackson

Pricing and retention

Confidently wrong, with perfect data

Jul 29, 2026

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8 min read

Confidently wrong, with perfect data

Your conversion numbers are accurate and your dashboard is current, but the channel that wins your budget meetings can still be taking credit for work another one did.

Jason Jackson
Jason Jackson

Founder bottleneck

You've never watched yourself sell

Jul 22, 2026

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9 min read

You've never watched yourself sell

Your best sales skill went automatic years ago. This week you get to watch it work.

Jason Jackson
Jason Jackson

Founder bottleneck

Your $250,000 hire is interviewing you

Jul 15, 2026

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8 min read

Your $250,000 hire is interviewing you

You brought in an operator to take the company off your plate. Three months in, you're more buried than before, and it looks like you picked the wrong person.

Jason Jackson
Jason Jackson

Runway and cash flow

The Series A You're Planning For No Longer Exists

Jul 8, 2026

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7 min read

The Series A You're Planning For No Longer Exists

You spent two years reaching your milestone. Then someone moved the goalposts.

Jason Jackson
Jason Jackson

AI adoption

The Label You Thought You Had to Add

Jul 1, 2026

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7 min read

The Label You Thought You Had to Add

You put "AI" on the homepage to win the deal. It became the reason the sale got harder.

Jason Jackson
Jason Jackson

Founder bottleneck

Why Your Team Brings You Every Decision

Jun 24, 2026

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8 min read

Why Your Team Brings You Every Decision

Your team ran the company for two weeks without you. Then you came home, and by Tuesday they'd forgotten how.

Jason Jackson
Jason Jackson

Runway and cash flow

The Profit That Can't Make Payroll

Jun 17, 2026

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7 min read

The Profit That Can't Make Payroll

Your P&L says you won the month. Your bank account says you're three weeks from missing payroll. Both of them are telling the truth.

Jason Jackson
Jason Jackson

Hiring and culture

Your Best Engineer Is Invisible to You

Jun 10, 2026

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7 min read

Your Best Engineer Is Invisible to You

He's kept your product up for nine months, but has anybody recognized his value?

Jason Jackson
Jason Jackson

AI adoption

One Scared Employee Can Kill Your AI Rollout

Jun 3, 2026

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8 min read

One Scared Employee Can Kill Your AI Rollout

You spent the money on the technology. The return is sitting with the person you gave a 20-minute heads-up.

Jason Jackson
Jason Jackson

Pricing and retention

The Front Desk Audit

May 27, 2026

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8 min read

The Front Desk Audit

Your $74,000 leak is invisible from the founder's chair. Sit in a different chair for a week.

Jason Jackson
Jason Jackson

Hiring and culture

The Junior You Didn't Hire

May 20, 2026

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8 min read

The Junior You Didn't Hire

The senior engineer you cannot afford to lose was supposed to be teaching the junior you decided to skip.

Jason Jackson
Jason Jackson

AI adoption

+1

You Are the Middle Manager

May 13, 2026

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9 min read

You Are the Middle Manager

The big-company AI playbook is making the founder bottleneck worse.

Jason Jackson
Jason Jackson

AI adoption

The Four Jobs of Outbound

May 6, 2026

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12 min read

The Four Jobs of Outbound

Three of them belong to AI. The fourth never should.

Jason Jackson
Jason Jackson

Pricing and retention

The Renewal You're Walking Into Blind

Apr 29, 2026

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5 min read

The Renewal You're Walking Into Blind

Your biggest customer is about to ask to pay you less. They're going to win.

Jason Jackson
Jason Jackson

Pricing and retention

The Loyalty Tax

Apr 22, 2026

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5 min read

The Loyalty Tax

The customers you're protecting with a grandfathered rate are halfway out the door.

Jason Jackson
Jason Jackson

Runway and cash flow

Two Sets of Books

Apr 15, 2026

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5 min read

Two Sets of Books

Every founder has two sets of numbers. Most pretend they don't.

Jason Jackson
Jason Jackson

Hiring and culture

The Fight You Had in the Garage

Apr 8, 2026

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6 min read

The Fight You Had in the Garage

Your co-founder relationship didn't break. It just got an audience.

Jason Jackson
Jason Jackson
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