The Keynote That Went Sideways | Dennis Moseley-Williams on Over-Preparation and Flow

Dennis Moseley-Williams joins Matt Zeigler for a conversation on creativity, preparation, and authenticity in the experience economy. They explore what it means to truly “show up” — balancing the control of preparation with the freedom of flow. From keynotes gone sideways to customer secrets and the power of belonging, Dennis shares personal stories and insights on how businesses — and people — can create genuine connections by being real, weird, and specific.

Topics covered:
• Knowing your stuff vs. controlling the chaos
• The difference between keynotes and workshops
• What it means to “show up” as your full self
• Why over-preparation kills creativity (and how ChatGPT plays into it)
• The Elvis Costello opening — starting with energy and authenticity
• Authenticity in the experience economy
• The role of customer secrets in creating magic
• When businesses become communities — “niche, niche, weird”
• How structure and ritual create freedom and flow
• Lessons from a keynote gone wrong — and how to recover

Timestamps:
00:00 Intro and setup
05:00 The power of customer secrets
08:00 Why preparation matters (and when it goes too far)
11:00 Knowing your stuff vs. controlling the chaos
15:00 Preparing vs. performing — finding your flow
17:00 The Elvis Costello opening
21:00 Authenticity and chemistry with audiences
27:00 The rise of individuality and belonging
29:00 Niche, niche, weird — when businesses become communities
33:00 The keynote nightmare story
37:00 Lessons learned from failure
39:00 Launching a new show and embracing flow
42:00 The importance of sweating the small stuff
43:00 Structure creates freedom
44:00 Where to find Dennis online