Cy has been an entrepreneur, founder and advisor for over two decades. Past companies include Intel Capital portfolio company PrepFlash, an EdTech company that uses NLP to automatically create flashcards from any content, and CloudCoreo, a configuration management company that garnered investment from Microsoft and ultimately sold to VMware. Cy was in the 2014 class of “Forty Under 40” for Professional Remodeler Magazine at the helm of the long-running real estate investment firm OCPS and was twice featured on TLC’s hit TV show “Flip That House”.
He is currently back in his hometown of Bloomington, Ind. with his wife Andrea and son Jack working for Elevate Ventures as Vice President of Software after spending the last 15 years in Austin, Seattle and the Bay area. He has a degree in Economics from Indiana University and an MBA from Baylor University, where he is an executive judge for their annual MBA Ethics competition.
The group discussed the myth of the perfect GTM plan. There’s no clean playbook - there’s a willingness to test, a feedback loop that actually informs decisions, and the courage to say no to the wrong audience. Nolan guided the conversation toward a central theme: GTM success is not about the size of the budget, it’s about how tightly aligned your product, team, and messaging are with the market moment you’re in.
Wade introduced the idea that early-stage branding doesn’t need to be expensive, but it does need to be intentional. Your identity should match your promise. Your tone should match your customer’s worldview. And your visuals should match the level of clarity you want people to associate with your company.
Ian Illig of Stompbox brought high-speed energy and tactical precision to his session on founder-led sales. Ian showed attendees how to translate a strong ICP into an actual sales strategy that doesn’t rely on luck or charm. Instead, it’s built on thoughtful structure, tight messaging, and an empathetic approach to outreach.