What does it really take to buy and run a small business?

In this episode of the American Operator Podcast, host Joseph Cabrera (JC) sits down with Army veteran and entrepreneur Nathan Lenahan to talk about the real, unfiltered reality of small business ownership.

Nathan shares the lessons he learned transitioning from the military into entrepreneurship, including the painful story of his first business acquisition that collapsed in less than 100 days, nearly wiping out his life savings and damaging relationships along the way.

Instead of quitting, Nathan rebuilt — starting small, doing things the right way, and eventually helping grow multiple successful home-service businesses.

In this conversation, they cover:

• Why veterans often make great business owners

• The harsh reality of buying your first business

• Why small business ownership can feel like “99% pain and 1% fun”

• Leadership lessons from the U.S. Army that translate to business

• Why local focus and community trust beat big corporate competition

• The importance of showing up every day when things get hard

Nathan also shares incredible stories from his time in the Army — including the leadership lessons that shaped how he builds teams and runs businesses today.

If you're thinking about buying a small business, becoming an operator, or building something of your own, this conversation is packed with hard-earned insights from someone who's lived it.