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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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Bill Flagg spent 20 years building 5 incredibly successful tech businesses, then unexpectedly sold them all.
To his own surprise, the thrill of building businesses faded, and he found himself craving a pause, a chance to become a beginner again and enjoy the simple things in life.
Two years ago, Bill moved with his family from Colorado to Portugal with no plans of returning anytime soon.
Today we discuss this transformation, his craving for inspiration, creativity, simplicity, and soul-nourishing experiences.
Connect with Bill
Linkedin: https://www.linkedin.com/in/bflagg/
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00:00:00 - 00:03:36 - Introduction and Background
00:03:36 - 00:04:31 - Transition to Sabbatical
00:04:31 - 00:06:24 - Loss of Passion and Creativity
00:06:24 - 00:07:45 - Embracing a Pause for Creativity
00:07:45 - 00:11:11 - Living with Uncertainty
00:11:11 - 00:16:16 - Rediscovering Life in Europe
00:16:16 - 00:19:33 - Letting Go of Past Identities
00:19:33 - 00:26:18 - Challenges with Possessions and Ownership
00:26:18 - 00:29:03 - The Root Cause of Post-Exit Struggles
00:29:03 - 00:31:13 - Embracing Retired Life
00:31:13 - 00:31:38 - Family Perspective and Legacy
00:31:38 - 00:33:22 - Final Thoughts
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