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

What happens after you exit a company you built from the ground up? In this episode of Innovator Insights, we talk to Connor Tomkies—founder of DelegateIt, Embark Vet, and Support Ninja (an Inc. 500 company). After bootstrapping and selling Support Ninja, Connor found himself in an unexpected identity shift. Instead of slowing down, he pivoted—launching a podcast, investing through Operator Equity, and building a 300-member entrepreneurial community with one goal: helping founders navigate growth and what comes after.We explore:The reality of low-margin vs. high-margin businessesBootstrapping through typhoons, pandemics, and scaleWhy the awkward teenage phase of a business is the toughestHow Connor’s Made It Podcast and Entrepreneur Cooperative were bornHis take on fulfillment, ambition, and rediscovering purpose post-exit If you’re building, scaling, or thinking about life after a startup—this is a must-listen.