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In this episode, Chris sits down with Rich Webster—designer, agency owner, and creator of How To Work Less—for a candid and hilarious conversation on carving your own path in business without becoming a parody of success. From viral tweets to quiet routines, Rich shares how he went from burned-out agency owner to calm creator—and how writing helped him escape the trap of performative entrepreneurship.

They dive into building an audience without selling your soul, why going quiet is sometimes the most strategic move, and how to tell stories that actually connect—without turning your life into content.

Timestamps:

(01:09) – Navigating Personal and Professional Change

(03:30) – Evolving from Agency to Lifestyle Business

(33:58) – Choosing Sobriety and What Came After

(36:23) – Hitting Reset: The Turning Point Toward Recovery

(59:04) – Vulnerability as a Strength in Business

Check out today's guest, Rich Webster:

Rich's Website: richwebster.co

Rich's Newsletter: worklesswednesday.com

Rich's Instagram: https://www.instagram.com/richwebz/

Rich's YouTube: https://www.youtube.com/@richwebz/

Rich's Threads: https://threads.net/richwebz

Check out The Futur:

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Check out Chris Do:

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