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Smart Side-Hustling

On priorities and the subtle art of doing one thing at a time

Blake Gossard
9 min readNov 1, 2018
“six white sticky notes” by Kelly Sikkema on Unsplash

I discovered the side-hustler’s dilemma back in middle school shortly after we’d all survived Y2K.

The year was 2001. My friends and I killed time playing Nintendo 64, waiting for the impending release of Diablo II for PC. My parents had recently upgraded the family computer to a next-gen beast with an Intel Pentium 4 processor. I was thrilled despite the lack of any alternative to the sloth-like dial-up internet service available in Rural Ohio where I grew up.

And there was music. Lots of it.

Right around the dawn of the new millennium, music went through a rapid evolutionary period characterized by an explosion of new artists, genres, and sub-genres. This was, for example, the heyday of pop-punk rock, and Blink 182’s Enema of the State album spent more time in my portable CD player than I’d like to admit.

Napster and the ability to burn custom playlists to CDs heralded mass exposure to new and different kinds of music over the internet, and how consumers acquired music was changing. But not everyone had the equipment or the know-how to burn their own custom CDs.

Being the visionary entrepreneurial seventh grader that I was (yuk yuk), I saw lots of opportunity in the space. I…

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Blake Gossard
Blake Gossard

Written by Blake Gossard

Critically Thinking & Typewriter Tinkering

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