In this conversation, serial entrepreneur and exited founder Omar Haroun reveals the hidden emotional cost of success, the identity collapse many founders experience post-exit, and why wealth alone often fails to deliver fulfillment.
Omar is a multi-exit entrepreneur and investor who has spent years studying the psychological and emotional realities of life after selling a business.
He reflects on the philosophy of life after success: how wealth gives safety but not security, why progress is really about trading old questions for better ones, and how many exited founders quietly waste their freedom by staying comfortable.
We explore:
• The moral responsibility that comes with capability
• Why regret is a better compass than ambition
• How founders get stuck using old success models in a new life
• Why contribution, not accumulation, becomes the real measure
