Jeff Hopeck welcomes Chris Shueler, CEO of Cyderes, a cybersecurity company founded by Shark Tank’s Robert Herjavec—who later hired his first outside CEO in Chris. Shueler traces a nontraditional path: after military service and finishing college, he planned to become a high-school history teacher, inspired by his own teacher. His wife challenged that “low ceiling,” pushing him to recognize his gift for leading people. He built his career by “leading from the front” while “leaders eat last,” empowering teams so their performance becomes his performance. After private-sector roles and an acquisition into IBM, he rose quickly—becoming a VP at 32—but his Enneagram 8 “challenger” wiring clashed with Big Blue’s constraints. Ten years of pushing boundaries—and being reprimanded for it—told him he needed a stage where challenging the status quo was an asset.
That arrived via “code name Stingray,” a nod to Herjavec’s car passion. One year into the Cyderes role, bookings are up 40% year over year, the brand is stronger than ever, and the company is leaning into market disruption—at the cost of intense travel (he logged ~80,000 domestic miles in his first three months).
Best advice: trust your gut. A senior government mentor (Ron Smith) once asked him what his gut said—then why he wasn’t trusting it. Since then, he’s learned that by the time you finally act on instinct, it’s often already too late. Biggest mistake: not trusting that gut when high-leverage opportunities appeared—twice. Earlier backers urged him to start his own firm, and in 2006 Amazon courted him to help build security for its nascent AWS. He balked—young family, relocation to Seattle, compensation heavy in stock—and still calls it a miss.
Life lesson/legacy: curate a spouse/partner and an inner circle who speak truth, create healthy friction, and want nothing but your greatness. CEO life is lonely; that support network sustains you. Follow Chris on LinkedIn, where he regularly challenges industry thinking on AI adoption and security.
🎙️Host : @jeffhopeckbrand
🚀Guest: https://www.linkedin.com/in/cschueler/