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Rob Norris

I may have a few gray hairs, but I'm a digital tech entrepreneur from the earliest days. My companies helped make online healthcare understandable, banking simple and data insightful. There have been my fair share of entrepreneurial mistakes. But I've also sold tens of millions of digital work, enjoyed a Fortune 500 exit, lived through acquisitions, landed National Science Foundation grants, published patents and even won a SXSW award. I'm not quite finished.

Don't quit your day job. Use it.

Jun 16, 2026

Don't quit your day job. Use it.

How to launch your second act without blowing anything up

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AI Didn't Fix the Bozos

Jun 9, 2026

AI Didn't Fix the Bozos

The 2026 update on innovation — and why your experience is worth more, not less

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Almost nobody uses AI

Jun 2, 2026

Almost nobody uses AI

ChatGPT just hit 900 million weekly users. The math is more interesting than the headline.

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Everybody starts too big

May 26, 2026

Everybody starts too big

Stop thrashing and do one thing

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Build your own door

May 19, 2026

Build your own door

Don't wait for gatekeepers to let you in

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Your agency of one

May 12, 2026

Your agency of one

How to build a screen porch side hustle

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A Newsletter Became a Community Became a Fund.

May 5, 2026

A Newsletter Became a Community Became a Fund.

What I learned helping my son build the audience he's now raising a venture fund on top of.

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You've Been a Copywriter for 30 Years. You Just Called It Something Else.

Apr 28, 2026

You've Been a Copywriter for 30 Years. You Just Called It Something Else.

The flood is here. The filter is the part you already built.

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Sun Tzu didn't have a 5-Year Plan

Apr 21, 2026

Sun Tzu didn't have a 5-Year Plan

And you don't need one either

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Nobody Saw This Coming

Apr 14, 2026

Nobody Saw This Coming

(Except the People Who Did)

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Listen to your father

Apr 7, 2026

Listen to your father

80's advice holds true today

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The Late-Career Entrepreneur: Why Starting After 50 Is a Competitive Advantage, Not a Handicap

Apr 4, 2026

The Late-Career Entrepreneur: Why Starting After 50 Is a Competitive Advantage, Not a Handicap

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Mastery is in high demand

Mar 31, 2026

Mastery is in high demand

Experience and judgement are exactly what the AI economy needs

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AI Won't Replace You. But a 28-Year-Old Using AI Might.

Mar 24, 2026

AI Won't Replace You. But a 28-Year-Old Using AI Might.

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Your biggest Business Idea is Already Solved

Mar 24, 2026

Your biggest Business Idea is Already Solved

You've been sitting on it for decades

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12 Encore Career Ideas for Executives (That Actually Use What You Know)

Mar 21, 2026

12 Encore Career Ideas for Executives (That Actually Use What You Know)

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Eat your own dog food

Mar 17, 2026

Eat your own dog food

AI agent projects you can build this weekend

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The Minimum Viable Exit (part 2)

Mar 10, 2026

The Minimum Viable Exit (part 2)

The 6-Month Exit Timeline (No Fluff Edition)

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The Minimum Viable Exit (part 1)

Mar 3, 2026

The Minimum Viable Exit (part 1)

AI acceleration has also sped up your departure time

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Find your recharge

Feb 24, 2026

Find your recharge

Spoiler alert: it's not the technology

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How to win when everyone has AI

Feb 17, 2026

How to win when everyone has AI

Build your moat

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Free to start

Feb 10, 2026

Free to start

The tools continue to be more powerful and less expensive

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Embrace your mastery

Feb 3, 2026

Embrace your mastery

The value of your uncommon knowledge

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The anti-hustle hustle

Jan 27, 2026

The anti-hustle hustle

Building sustainable side businesses after 50

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The power of one

Jan 20, 2026

The power of one

AI agents to improve whatever you're doing

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