CVBO Warrior Webinar: Navy Seal to CEO with Sam Mackey
The Chicagoland Veteran Business Owners (CVBO) Warrior Webinar series brings real stories and real lessons from veterans who are building what’s next.
This month, we’re hosting Navy SEAL veteran and CEO of Outsider, Sam Mackey. Sam spent years serving in the SEAL Teams before making the jump into business. Today, he leads Outsider, an outdoor lifestyle brand he now runs in partnership with former NFL quarterback Jay Cutler and co‑hosts the “Take It Outside” show.
In this live, one‑hour conversation, we’ll explore:
Sam’s path from military service to the next chapter of his life and career.
The story behind Outsider and how his partnership with Jay Cutler came together.
What he’s learned as a CEO about leadership, risk, and building a mission‑driven brand.
Why Outsider chose to become the first official sponsor of CVBO and what it looks like when veteran‑led organizations support each other.
We’ll leave time for live Q&A, so you can ask Sam about transition, family, purpose, and building something meaningful after the uniform.
Who should attend
Veteran and military‑connected entrepreneurs and business owners in Chicagoland.
Service members, Guard/Reserve, and military spouses thinking about their next chapter.
Community members and employers who want to find and support veteran‑owned businesses.
About CVBO
Chicagoland Veteran Business Owners (CVBO) is a nonprofit created by and for veterans, military spouses, and military family entrepreneurs in the greater Chicago area. We support, promote, and advocate for veteran‑owned businesses through community, education, and connection.
Join us, hear Sam’s story, and learn how you can be part of a growing movement to help veteran businesses thrive—and to find and hire veteran‑owned businesses in your own network.