Ben White. He's sold three businesses so far for $80M, $88M and $800M. It was the last exit 16 years ago that hit him hard. What followed was a dark decade filled with divorce, addiction and significant financial losses. However, today Ben is the happiest he's ever been. In this episode we discuss his hard-earned lessons on happiness, why he started his fourth business now and walked away from running his VC firm. _____________________________________________________ TIME STAMPS: 00:00 - Introduction 01:33 - The impact of the 2008 exit and the dark decade 03:10 - Initial feelings and challenges post-exit 05:32 - Divorce and addiction struggles 07:51 - The sudden change in life without a business to run 09:55 - Coping mechanisms and poor investment decisions 11:57 - The importance of grounding oneself after a major life change 14:02 - Reflections on making poor decisions and facing addiction 16:10 - The importance of dealing with significant life events 18:08 - Advice to the younger self: taking time off and dealing with addictions 19:53 - The impact of personal struggles on family 21:54 - Strategies for being present and engaging with children 24:02 - The role of family in finding happiness 26:02 - Recognizing the importance of real friends and authentic relationships 28:20 - The danger of wealth changing social dynamics 30:25 - The importance of staying grounded and real 32:23 - Transition from VC firm back to entrepreneurship 34:20 - The creation of UP and its vision 36:19 - The importance of having a clear purpose and passion for work 38:21 - Changes in views on wealth and financial freedom 40:35 - The role of money in achieving happiness 42:22 - Learning to appreciate simple pleasures in life 44:12 - Finding happiness in nature and everyday moments 46:26 - Teaching kindness and empathy to children 48:29 - The role of nature in achieving a balanced and happy life 50:25 - The desire to leave a meaningful legacy 52:26 - The importance of helping others and making a positive impact 54:33 - Reflections on how to be remembered 56:29 - Parenting strategies and guiding children towards real values 58:28 - The importance of independence and real-world experiences for children 01:01:04 - Balancing drive and contentment in personal and professional life 01:03:26 - The journey to finding personal happiness 01:05:20 - Combining contentment with entrepreneurial drive 01:07:30 - Final thoughts on balancing life, work, and happiness