About this episode
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/
_____________________________________________________
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
Get every episode summarized
Each time Exit Paradox publishes, we email you a written briefing from the transcript — the topics, who appeared, and any specific claims, with the ad reads skipped.
Email me new episodesFree for 3 shows. No card needed.
Hosts & guests
No transcript yet
This episode has not been transcribed. Request it and it moves to the front of the queue.
More episodes
More from Exit Paradox
Why Building Again Can Be Harder After Success | Eric Ries
Exit Paradox
Post-Wealth Expert: How To Re-ignite Drive and Energy After Financial Success
Exit Paradox
Omar Haroun: “Outsized Impact is Incredibly Rewarding”
Exit Paradox
The Wealth Lag: What Happens AFTER Financial Freedom
Exit Paradox