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Josh Penner
Josh Penner
The Six Questions you Should as Every GovTECH ( & AI) Vendor..

Aug 5, 2026

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8 min read

The Six Questions you Should as Every GovTECH ( & AI) Vendor..

The debate is almost never about the feature. Here is the math you are already running, and how to make it explicit before you sign anything.

Josh Penner
Josh Penner
4 Years Ago this Scam Took Months, and Cost My City $500k. Now It Takes a $20 AI Subscription.  Here's how you protect your city.

Jul 29, 2026

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14 min read

4 Years Ago this Scam Took Months, and Cost My City $500k. Now It Takes a $20 AI Subscription. Here's how you protect your city.

We paid five hundred thousand dollars for the lesson. The next version costs the criminal almost nothing.

Josh Penner
Josh Penner
I Ran My City by Asking One Question. Ask It About Artificial Intelligence Before You Become a Headline

Jul 14, 2026

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10 min read

I Ran My City by Asking One Question. Ask It About Artificial Intelligence Before You Become a Headline

Josh Penner
Josh Penner
The Post Vote Scavenger Hunt

Jun 5, 2026

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8 min read

The Post Vote Scavenger Hunt

Tracking the local impact of state laws shouldn't require you to be a private investigator..

Josh Penner
Josh Penner
You Are Not a Mayor, the CEO, or the President. You Are a Chief Risk Officer.

Apr 17, 2026

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20 min read

You Are Not a Mayor, the CEO, or the President. You Are a Chief Risk Officer.

If you step into a public executive role, you need to shatter the illusion of the philosopher visionary. Your real job revolves entirely around risk management.

Josh Penner
Josh Penner
Pre-Mortems vs. Post-Mortems: The Anticipatory Executive Strategy Muscle

Apr 7, 2026

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20 min read

Pre-Mortems vs. Post-Mortems: The Anticipatory Executive Strategy Muscle

Survivor Bias is Killing Your Organization and Weakening Your Team (Here's How you Fix It)

Josh Penner
Josh Penner
The Executive Information Bubble Trap

Mar 31, 2026

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9 min read

The Executive Information Bubble Trap

This is the Executive Information Bubble. And it is the fastest way to lose control of your organization.

Josh Penner
Josh Penner

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Potholes & Pixels

The Penner Strategy Briefing. Navigating the messy reality of leadership with modern, tactical solutions. Written by a Mayor, Marine, and Entrepreneur for executives in the trenches.

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