In this episode, I sit down with Jeff Ahern — a former Reconnaissance Marine turned full-time real estate investor, husband, and father. Jeff shares how he and his wife Megan went from losing $50K on their first flip to building a thriving business that now flips 30+ houses a year, manages 40+ rental doors, and co-owns multiple companies.
Together, we dig into:
How to turn setbacks into stepping stones — Jeff’s journey from medical separation to entrepreneurship.
Why your first big loss might be the best thing that happens to you — and how to bounce back stronger.
The exact steps Jeff and Megan used to scale from one trailer-parked house flip to a diversified real estate empire.
What military discipline can teach us about business systems and the power of delayed gratification.
If you’ve ever struggled with self-doubt, early failures, or fear of taking the leap into real estate, this conversation will give you the mindset and tactics to keep moving forward.
Episode Timestamps
(00:00) Welcome to the Military Millionaire Podcast
(02:15) Meet Jeff and his military-to-real estate journey
(08:00) Lessons from losing $50K on their first deal
(15:20) Scaling flips and rentals the right way
(24:50) The role of sacrifice, systems, and delegation
(32:10) Building multiple income streams (title, staging, rentals)
(35:00) Advice for new investors + future plans
About the Show
Welcome to the Military Millionaire Podcast, where we teach service members, veterans, and their families how to build wealth through personal finance, entrepreneurship, and real estate investing. I'm your host, David Pere, here to be your no-BS guides along the most important mission you’ll ever embark on — your finances.
Connect with Today's Guest, Jeff Ahern
Connect with David Pere
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