MILCOM Founders Podcast – Episode 25: From Air Force Linguist to Building San Antonio’s Startup Ecosystem with Charles Woodin

Join host Rod Loges and guest Charles Woodin, CEO of Geekdom, as he shares his journey from serving as an Air Force Korean linguist to leading San Antonio’s premier entrepreneurial community. Charles discusses how his military experience shaped his leadership philosophy and how Geekdom is transforming founders from zero to one.

In this episode:

• Charles’s path from small-town Michigan to Air Force linguistics training with a 50%+ attrition rate
• How his family’s relocation to Texas due to NAFTA exposed him to different cultures and perspectives
• The leadership lessons learned from eight years of Air Force service, including the importance of getting the job done and building consensus
• Geekdom’s evolution from addressing San Antonio’s startup ecosystem gap to comprehensive entrepreneurial programming
• The critical role of customer development and market validation over fundraising
• Why collaboration beats competition in building thriving startup communities
• How AI serves as a force multiplier for resource-constrained founders
• The connection between military talent and entrepreneurial solutions for national defense challenges

Key takeaways:

• The best founders solve problems they’ve personally experienced and understand deeply
• Customer revenue is the best form of validation, better than investor funding
• Building a startup ecosystem requires collaboration between universities, government, business, and entrepreneurs
• Military veterans bring unique problem-solving skills and intimate knowledge of defense challenges
• Effective leadership means getting people invested in the mission, not just giving orders
• Over 70% of founders who start Geekdom’s process don’t complete it, which is actually valuable for helping people avoid wasted time and resources

Guest: Charles Woodin, CEO of Geekdom, Air Force Veteran (8 years of service)
Linkedin: https://www.linkedin.com/in/charleswoodin/
Website: https://geekdom.com/

Charles Woodin is the CEO of Geekdom, a startup incubator founded in 2011 dedicated to growing San Antonio’s entrepreneurial ecosystem. Since joining Geekdom in 2017 as a Business Development Manager, Charles took on increasing responsibilities, moving into the role of Membership Director before being appointed CEO in 2019.

Under his leadership, Geekdom has redefined its mission, launched key initiatives like the Accelerate South Texas Fund, and partnered with the City of San Antonio to oversee Launch SA, fostering innovation and small business growth. A former U.S. Air Force Staff Sergeant, Charles served as an Airborne Cryptologic Language Analyst for eight years, specializing in intelligence collection and training.

Originally from Michigan, Charles now calls San Antonio home, where he is deeply committed to its growth. Outside of work, he enjoys traveling, hiking national parks, and spending time with his daughters, Penelope and Amelia.

Resources mentioned:

• “Start With Why” by Simon Sinek
• “The Hard Thing About Hard Things” by Ben Horowitz
• “Startup Communities” by Brad Feld

Looking ahead: Charles continues leading Geekdom’s mission of “building San Antonio, one entrepreneur at a time” while exploring virtual programming options and strengthening partnerships with veteran-focused organizations like V Source.

The MILCOM Founders Podcast champions and celebrates military community business owners. Each episode brings practical insights and lessons learned from successful veteran entrepreneurs.

Sponsored by One Degree Financial www.onedegreefinancial.com

Want to support veteran entrepreneurs? Learn about the Dick Loges Veteran Entrepreneur Scholarship Fund at https://www.milcomfounders.com/