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18 Mind-Blowing Digital Mavericks Who Turned Weird into Wealthy

Fahri Karakas
7 min readAug 1, 2024
Photo by Firmbee.com on Unsplash

Forget everything you think you know about building a million-dollar business.

These 18 digital entrepreneurs did not just think outside the box. They almost set the box on fire and danced around it!

Coding in silence punctuated by heavy metal blasts?

Building empires from hospital beds?

These stories prove success has no template.

Prepare to have your mind blown by the unconventional habits, decisions, and strategies that led these solo pioneers to seven-figure success.

Warning: Reading this might just inspire you to embrace your own brand of weird and revolutionize your approach to business.

1. Derek Sivers — CD Baby

Derek Sivers built CD Baby into a $100 million company but sold it for $22 million — to a charitable trust.

The mind-blowing part? He gave away the entire proceeds.

His quote: “I didn’t want to be a billionaire looking for ways to spend it. I wanted to be a minimalist, doing only what I wanted to do.”

Sivers had a peculiar habit of taking long walks — sometimes up to 8 hours a day — to think through business problems.

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Fahri Karakas
Fahri Karakas

Written by Fahri Karakas

Associate Professor in Business & Leadership at University of East Anglia. Passionate about doodling, imagination, and creativity. Author of Self-Making Studio.

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