MILCOM Founders Podcast — Episode: From Naval Academy to Marine Osprey Pilot to Business Owner with Ahron Oddman

Join host Rod Loges and guest Ahron Oddman as he shares his journey from Brooklyn teenager to Naval Academy graduate, Marine Osprey pilot, and successful business owner through entrepreneurship.

In this episode:

• Ahron’s path from a 9-year-old inspired by an air show to Naval Academy aerospace engineering graduate
• His decision to choose Marines over Navy and becoming one of the early Osprey pilots
• Flying combat missions in Operation Iraqi Freedom and helping write the manual for a new aircraft
• Acquiring PSS in March 2020 – just weeks before COVID shut down schools nationwide
• How military startup experience with the Osprey prepared him for business challenges
• Navigating the acquisition process and building relationships with existing teams
• The similarities between military leadership and business ownership

Key takeaways:

• Sometimes the path chooses you – embrace unexpected opportunities rather than rigid plans
• Early experience with “startup” environments (like new aircraft programs) translates directly to business
• Mission first, people always – prioritizing team welfare drives customer success
• Entrepreneurship through acquisition offers veterans immediate leadership opportunities
• Teaching, tailoring, and taking charge are essential sales principles
• Integration of faith, family, and business creates sustainable success

Guest: Ahron Oddman, CEO and Co-founder of PSS, Marine Osprey Pilot (15 years of service)

LinkedIn: https://www.linkedin.com/in/ahronoddman/

Business Website: https://pssk12.com/

Ahron Oddman is a Marine veteran who served as an Osprey pilot for 15 years, including combat deployments during Operation Iraqi Freedom. Originally from Brooklyn, New York, Ahron graduated from the U.S. Naval Academy with a degree in aerospace engineering before commissioning as a Marine officer.

As one of the early Osprey pilots, Ahron helped develop tactics and procedures for the revolutionary aircraft, giving him unique experience with startup-like environments within the military structure. After his military service, he transitioned to the private sector before acquiring PSS, a 25-year-old educational services company, in March 2020.

Ahron’s acquisition of PSS came just weeks before COVID-19 shut down schools nationwide, providing an immediate test of his leadership and adaptability. He successfully guided the company through the pandemic while developing new digital products and maintaining strong customer relationships.

Looking ahead: Ahron continues to lead PSS while mentoring other veterans interested in entrepreneurship through acquisition, sharing hard-won lessons about the realities of business ownership beyond the search process.

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/