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The Ramblings of The Chief Rainmaker

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Gil Ortega

Gil Ortega

Gil Ortega. Internet entrepreneur since 1998. Author, artist, Chief Rainmaker. Business, travel, art, and whatever else I can't stop thinking about.

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Collage of Gil Ortega's brands, logos and photos under the banner Ramblings of the Chief Rainmaker.

Welcome to The Ramblings of The Chief Rainmaker

(Or: What Happens When You Give a San Diego Kid Big Ideas)

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Ramblings
Cover of the CHILI Productions memoir: a giant red chili pepper over a collage of 1980s and 90s San Diego nightclub flyers. Events from 1985 to 2001.

CHILI Productions

From Flyers to Stories — The Book

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CHILI Productions
A man at a desk at night studying an online dating profile on a glowing computer screen.

One in a Million

How I went from zero dates in a year to seven a week without changing a word of my profile. And why my wife is glad I never emailed her.

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Ramblings
A banker in a suit and a fisherman on a dock at sunset beneath a signpost asking What's your end game?

The Banker and the Fisherman

"What's your end game?"

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The Un-Retired Life
A man working on a laptop on a mountainside at sunrise above the words The Un-Retired Life.

The Un-Retired Life

Living The Perpetual Freedom Work-Life

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The Un-Retired Life
An air mattress on a dark floor facing a split mural of storm clouds and gears giving way to a bright sunrise.

The Power of Reframing

The Smoke Signal

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The Un-Retired Life
A sealed envelope marked with a question mark beneath the words The Entrepreneur Test.

The Entrepreneur Test

Would You Give a Year to Get a Year?

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BusinessXLR
A split image: a man chasing a red balloon on one side, a figure meditating at sunrise on the other.

Stop Chasing Happiness. Anchor Yourself in Peace.

For a long time, I thought happiness was the foundation for everything.

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The Un-Retired Life
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GIL ORTEGA

The Ramblings of The Chief Rainmaker. Gil Ortega on business, travel, art, and life. The lead generation operator. The artist. He's the guy who never stops building.

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