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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TIME STAMPS:
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