Roy Rubin the visionary founder of Magento, built the open source e-commerce platform from the ground up, leading it to a remarkable exit to eBay in just four years. He then stayed on at eBay for two years, but felt suffocated by corporate walls. That's when it hit him. 

He barely knew his family anymore. 

So he and his wife pulled their kids out of school, packed up. and set off on an open-ended journey around the world. For 14 months, they traveled without a plan, letting each destination choose them and discovered what freedom really meant. When they returned, threw himself into the challenge of cycling and completed an Ironman. 

He also started an angel investment firm to stay intellectually engaged. He has built a beautiful life, but now 13 years post-exit, he is still looking for a new purpose. 

Roy is torn between the urge to build something big again and the fear of sacrificing his family and lifestyle. Roy is disarmingly open and witty in this conversation. His ideas on personal growth, leadership and fulfillment are fresh and thought-provoking. 

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00:00:00 : Introduction and greetings
00:01:38 : Roy's background and introduction to Magento 
00:02 :3: The founding and growth of Magento 
00:03:36 : Why Magento was sold to eBay 
00:05:28 : Reflections on selling Magento 
00:05:53 : Period after selling: Working at eBay 
00:06:51 : Challenges and experiences at eBay 
00:10:18 : Frustrations and limitations at eBay 
00:11:07 : Difficulty in leading within eBay 
00:13:39 : Reflections on regret and learning from the experience 
00:15:53 : Pain of working at eBay 
00:18:04 : Changes in the leadership team post-acquisition 
00:19:25 : Leadership style and inspiration 
00:22:07 : Transparency and leadership approach 
00:25:24 : Personal reflections post-exit 
00:25:48 : Reflecting on leaving Magento in 2013 
00:28:03 : Deciding to leave eBay after Magento's Imagine conference in 2014 
00:29:15 : The decision to travel with family for 14 months 
00:30:00 : The travel route through Central America, South America, Asia, and Europe 
00:31:03 : The travel experience and its impact on family dynamics 
00:36:04 : Encouragement to other founders to take time off and travel 
00:43:02 : Discovering new passions post-travel, specifically Iron Man and cycling 
00:45:59 : Introduction to Personal Journey 
00:46:26 : Discovering Passion for Sports 
00:46:10 : Reinventing Post-eBay Life 
00:46:44 : Starting the Fund During COVID 
00:48:04 : Transition to Angel Investing 
00:51:27 : Managing Wealth Post-Magento Sale 
00:54:03 : Investment Philosophy and Public Equities 
00:56:45 : The Non-Financial Rewards of Investing 
00:58:17 : Search for Purpose Beyond Business 
01:01:27 : Reflection on Purpose During Magento Years 
01:03:33 : Balancing Life with Current Ventures 
01:06:12 : Discussing a life of 24/7 dedication 
01:06:47 : The search for purpose 
01:08:01 : Meeting new people 
01:10:00 : The intense journey with Magento 
01:12:56 : Coping with the transition post-acquisition 
01:16:07 : Being a creator versus an operator 
01:19:11 : Future impact and legacy 
01:22:10 : The desire for more meaningful work 
01:26:21 : Closing remarks and goodbyes