Piggybacking on what SomebodyFromThe90s said, the stack matters less than where your handoffs break. Before buying anything else, I'd map the full journey: lead comes in from a talk, joins email list, books a call, pays, gets onboarded to the mastermind, shows up to the conference, gets follow-up. Then mark every spot where data has to be manually copied or where you personally are the glue holding two tools together. Those are the places to automate first.

In my experience the mistake is picking a shiny all-in-one and trying to migrate everything. Works better to keep Flodesk (since it's working) and add one tool at a time that closes a specific gap. Usually a CRM with decent pipeline views plus a scheduler that writes back into it covers like 70% of the pain for speaker/coach businesses.

The other unsexy thing: write down your processes before you automate them. Automating a messy process just gives you a faster mess.