Robert Wolfe Class Of 1999


Robert “Bobby” Wolfe is retired Lieutenant Colonel and decorated aviator. He is proud to have started his Air Force adventure as a "Preppie" and later as a graduate of the Air Force Academy Class of 1999. Upon graduation, Bobby served as strategic airlift pilot flying more than 2,300 total hours including 189 combat hours into hostile airspace around the world. The last decade of Bobby's USAF career was dedicated to supporting the Air Force Academy mission culminating as the Liaison Officer Director of USAFA's largest geographic area where he is proud to have positively impacted hundreds of USAFA, Prep School and Falcon Foundation appointees from more than 2,800 schools across 30+ congressional districts throughout Florida and the Caribbean.

Outside of his military accomplishments, Bobby leads the Cyber Security Investment Banking practice at Houlihan Lokey where he advises investors, founders and leading cyber security companies in all aspects of corporate finance and M&A. Bobby has garnered multiple awards for private equity, cross-border and complex M&A transactions. He has advised on more than $17bn in transaction value over the years and started his investment banking career at Morgan Stanley in Silicon Valley. Bobby holds degrees from the United States Air Force Academy, the University of Oklahoma and Harvard Business School. Today, Bobby lives in Tampa, Florida with his wife, their four children, two dogs, a cat and a bunny.

Candidacy Statement

While picturesque and backed by the full strength of our great country, it’s the Alumni, cadets and community that make our Air Force Academy a national treasure. Alumni from all walks of life are leaders in their community, the military, government, academia, and industry. I have met Alumni from every class over the years and have been impressed with every story. They constantly reminded me that each USAFA graduate is superb individually, and we’re even better together. United in our core values, experiences and sacrifices, we are a force for good here in the USA and around the world. As a member of your AOG Board of Directors, I look forward to serving all graduates with the goal of strengthening the Long Blue Line through meaningful engagement and support for all Alumni while in uniform and beyond. If you have any questions, suggestions, gripes or concerns about your AOG (or anything, really), feel free to reach out any time to or +1-984-664-1999. I look forward to hearing from you.