18 - Bootstrapped, Scaled, Sold— Now What? Connor Tomkies on the Hidden Cost of Success

This episode explores entrepreneurship, focusing on the journey of Connor Tomkies, founder of DelegateIt, Embark Vet, and Support Ninja. Tomkies shares his early entrepreneurial experiences, including starting DelegateIt while in college and the challenges of low-margin businesses. Against the backdrop of DelegateIt's struggles, he highlights the contrasting success of Embark Vet, a dog genetics company, leading to a strategic shift in focus. More significantly, the discussion pivots to Support Ninja, an international outsourcing company, where Tomkies details the difficulties of managing a large global workforce amidst various crises. As the conversation evolves, Tomkies reflects on his post-exit experiences after selling Support Ninja, emphasizing the importance of peer support and community for entrepreneurs. The episode concludes with Tomkies sharing his current focus on the Entrepreneur Cooperative and Operator Equity, underscoring his passion for helping other founders navigate the scaling and exit process, reflecting emerging industry patterns centered on community and shared learning.