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Dan Healy
Dan Healy
#171 GTM vs. VTM...wait, what's VTM??

Sep 15, 2026

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5 min read

#171 GTM vs. VTM...wait, what's VTM??

Every founder I've met is missing the same thing

Dan Healy
Dan Healy
#170 I DM'd a VC on a Sunday morning

Sep 8, 2026

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5 min read

#170 I DM'd a VC on a Sunday morning

3 months of warm-up for a 12-minute meeting.

Dan Healy
Dan Healy
#169 Three months without a paycheck

Sep 1, 2026

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5 min read

#169 Three months without a paycheck

The pros and cons of leaving a 10-year career

Dan Healy
Dan Healy
#168 Claude Cowork sold my furniture

May 5, 2026

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5 min read

#168 Claude Cowork sold my furniture

Steal the workflow. No AI experience needed.

Dan Healy
Dan Healy
#167 I broke up with ChatGPT

Apr 21, 2026

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5 min read

#167 I broke up with ChatGPT

Plus a prompt to check if you should switch.

Dan Healy
Dan Healy
#166 Missions nobody else can see

Apr 14, 2026

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3 min read

#166 Missions nobody else can see

"Get in shape" isn't a mission.

Dan Healy
Dan Healy
#165 Reasons or excuses?

Apr 7, 2026

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6 min read

#165 Reasons or excuses?

OTF's longtime co-pilot signs off.

Dan Healy
Dan Healy
#164 3 skills AI assists, not replaces

Mar 31, 2026

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8 min read

#164 3 skills AI assists, not replaces

Guest edition, plus a student's quiz trick.

Dan Healy
Dan Healy
#163 She's 22 and way ahead of me

Mar 24, 2026

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10 min read

#163 She's 22 and way ahead of me

Two Gen Z convos, two prompts to steal.

Dan Healy
Dan Healy
#162 The caddy job that became a career

Mar 17, 2026

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10 min read

#162 The caddy job that became a career

Listen, adapt, build relationships.

Dan Healy
Dan Healy
#161 $200 a month on AI. Worth it?

Mar 10, 2026

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11 min read

#161 $200 a month on AI. Worth it?

Turn the setting off. Steps inside.

Dan Healy
Dan Healy
#160 Information isn't learning

Mar 3, 2026

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11 min read

#160 Information isn't learning

How I'd have launched OTF with Notebook LM.

Dan Healy
Dan Healy
#159 The lunch table went quiet

Feb 24, 2026

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10 min read

#159 The lunch table went quiet

AI at work: the fear, the data, the fix.

Dan Healy
Dan Healy
#158 Did AI write this?

Feb 17, 2026

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11 min read

#158 Did AI write this?

Personality is the new hiring edge.

Dan Healy
Dan Healy
#157 2 minutes of thinking saves 45

Feb 10, 2026

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8 min read

#157 2 minutes of thinking saves 45

9 prompting moves you already know how to do.

Dan Healy
Dan Healy
#156 3 years. 3 things kept it alive.

Feb 3, 2026

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10 min read

#156 3 years. 3 things kept it alive.

Ideas, partnerships, and the why.

Dan Healy
Dan Healy
#155 My 2026 AI team

Jan 27, 2026

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8 min read

#155 My 2026 AI team

Plus the tip: use AI to prompt your AI.

Dan Healy
Dan Healy
#154 Did you buy it or get nudged?

Jan 20, 2026

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9 min read

#154 Did you buy it or get nudged?

Design the environment, design the behavior.

Dan Healy
Dan Healy
#153 A retiree, a bike shop, and Perplexity

Jan 13, 2026

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9 min read

#153 A retiree, a bike shop, and Perplexity

One reader, four problems, zero tech background.

Dan Healy
Dan Healy
#152 Two kids sold a newsletter for $75M

Dec 30, 2025

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7 min read

#152 Two kids sold a newsletter for $75M

The edition where building in public started.

Dan Healy
Dan Healy
#151 Patience is the common thread

Dec 23, 2025

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7 min read

#151 Patience is the common thread

A guest's three lessons from 2025.

Dan Healy
Dan Healy
#150 Money is emotional as hell

Dec 16, 2025

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7 min read

#150 Money is emotional as hell

3 money lessons that aren't about tactics.

Dan Healy
Dan Healy
#149 You're not too late. Yet.

Dec 9, 2025

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9 min read

#149 You're not too late. Yet.

My 3 AI takeaways from 2025.

Dan Healy
Dan Healy
#148 Give first. Then ask.

Dec 2, 2025

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7 min read

#148 Give first. Then ask.

Plus the 5-word pitch formula I stole.

Dan Healy
Dan Healy
#147 7 years in, I owned nothing

Nov 25, 2025

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8 min read

#147 7 years in, I owned nothing

3 lessons from 3 years of publishing.

Dan Healy
Dan Healy
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