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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this memo, we pop the hood on one of the biggest fears coaches have around automation: Will it make me sound cold? Spoiler — not if you do it right.
Coaches care deeply, which means they also overextend. Late-night DMs, forgotten follow-ups, mental guilt tabs… it adds up. In this episode, I break down why smart automation doesn’t replace relationships — it protects them. Think of it like a bodyguard for your energy, guarding the small, repetitive tasks so you can stay fully present when it counts.
You’ll learn my simple Protect → Personalize → Preserve framework, plus three connection-building automations any coach can build in under a week:
- Progress reflections that help clients feel seen.
- Milestone celebrations that spark loyalty.
- Gentle re-engagement nudges that prevent awkward silence.
I’ll also walk you through the Relationship Safety Test — five quick questions that keep your automations warm, human, and helpful.
If your backend feels like friction instead of flow, this memo will show you how to automate with empathy and keep clients feeling held, not herded.
Ready to safeguard your sanity and your client experience?
Let’s get to work.
8 episodes
