Connor Tomkies. He spent 8 years growing and selling SupportNinja, his global talent acquisition firm. Now he focuses on buying great businesses to scale them for exit. This episode delves into Connor’s exit experience, why he prefers to buy a significant portion of a business over angel investing, and how helping out his extended family members turned out to be the most rewarding use of his exit wealth.

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Timestamps: 00:00:00: Intro 00:01:16: Welcome 00:01:26: The sale of Support Ninja 00:02:42: The experience of selling a company 00:03:08: Lessons learned from selling the company 00:09:48: The start of Operator Equity 00:10:10: How Operator Equity works 00:12:01: Explanation of EOS (Entrepreneur Operating System) 00:14:22: Experiences with EOS and why it was chosen 00:17:01: Ambitions for Operator Equity 00:17:15: Why Operator Equity was started 00:18:11: Personal love for inception and growth of a company 00:19:27: Investment in mature companies 00:20:33: Managing the creative impulse with mature companies 00:21:11: Beginning of Operator Equity journey 00:21:26: Looking ahead: The future of Operator Equity 00:22:15: Reflections on the impact of ego in business 00:23:04: The notion of fleeting success and the value of the journey 00:23:43: The struggle of self-identity post exit 00:26:13: The evolution of thoughts about money and wealth 00:28:24: The challenges and fears related to sudden wealth 00:31:06: Caution around extending financial security to others 00:31:45: Uncertainty in defining personal success after exit 00:33:22: The impact of financial success on personal relationship 00:35:45: Thoughts on sense of purpose post business exit 00:37:55: Avoiding guilt through conscious actions in business 00:39:56: Managing imposter syndrome and motivation 00:43:02: Expectations and understanding of success from parents' perspective 00:43:55: Discussion about stepping down and operator equity 00:44:23: Thoughts on raising future children and entrepreneurship 00:45:35: Talks on operator equity and investments 00:47:24: Inquiry over work-life balance 00:48:42: Question on personal legacy 00:49:50: Conclusion and best wishes for future projects