The first time I broke a company’s entire sales pipeline, it was a Tuesday in November. 2018. We were moving from a messy pile of spreadsheets to Salesforce because the VP of Sales thought it would magically make the team hit their quotas. It didn’t. I spent my 29th birthday—November 14th, if you’re curious—huddled over …
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 …
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 …
