The Interview · Track 5
Seventy-Five Businesses
Lo-fi Dream-Pop · Wry, earned, slightly melancholic but warm — like a wise older friend telling you what they wish they knew at 25
Andrew Wilkinson · I've run 75+ businesses. Here's why you're probably chasing the wrong idea.
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“I was at one point worth over a billion dollars... and I'm still just as anxious as ever.”- Andrew Wilkinson
The Story Behind This Song
Andrew Wilkinson went from barista to billionaire by co-founding Tiny, a holding company owning 40+ businesses including Dribbble, AeroPress, and Letterboxd. Along the way he lost $10 million competing with Asana via bootstrapped Flow, failed at cat furniture, a DJ school, and skin cream. The biggest revelation wasn't a business insight — it was getting diagnosed with ADHD at 40 and finding that one tiny SSRI pill did more for his mental state than all the exits combined.
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I've run 75+ businesses. Here's why you're probably chasing the wrong idea.
Andrew WilkinsonPodcast
