In 2018, I sat in a glass-walled office in downtown Chicago and realized I was paying $6,000 a month for a ‘Growth Lead’ who spent most of his day adjusting the padding on our internal slide decks. I had four employees back then. We were doing okay—maybe $400k in revenue—but after payroll, rent, and the …
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entrepreneurship
Why I Fired the Client Who Paid 60% of My Bills (And Lived)
On October 14th, 2021, I sat in my car in a grocery store parking lot and cried for twenty minutes because a guy named Steve sent me a Slack message asking for a ‘quick’ update on a spreadsheet. Steve was my biggest client. His company, a mid-sized logistics firm in Chicago, was paying me $8,400 …


