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 businesses
- Bootstrapping through typhoons, pandemics, and scale
- Why the awkward teenage phase of a business is the toughest
- How Connor’s Made It Podcast and Entrepreneur Cooperative were born
- His 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.
Popular Podcasts
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
Las Culturistas with Matt Rogers and Bowen Yang
Ding dong! Join your culture consultants, Matt Rogers and Bowen Yang, on an unforgettable journey into the beating heart of CULTURE. Alongside sizzling special guests, they GET INTO the hottest pop-culture moments of the day and the formative cultural experiences that turned them into Culturistas. Produced by the Big Money Players Network and iHeartRadio.