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> Can someone chime in why this hasn't worked in the past?

Because spreadsheets and notes are free and good enough.

I used to be a full time shitty cheap car flipper. I used to be single. They're about the same level of communication work. The ROI of a proper CRM isn't there because in both cases your customer is just not that serious about the interaction when they're in the part of the funnel a CRM helps you with and even then it doesn't really help you with the bulk of the customers, it helps you with the long tail. When you're a one man shop squeezing out an extra 1% or whatever a CRM gets you isn't worth the time vs focusing on other areas. (These days I work in a client facing role with a proper ticketing system and integrated CRM so I do have something to compare to.)



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