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Robert is a former Marine who found his way into corporate M&A through grit and bit of luck.

He now runs a firm providing financial advisory services to small and medium-sized businesses.

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Gabe and Lindsey are both Army veterans with impressive backgrounds, he an infantry officer and she was one of the first women in the 160th.

After leaving the Army, Gabe started a fire/water/mold remediation business, scaled it to $1 million in a few years and then sold it, while Lindsey is an MBA student at HBS.

Oh, and they are married. Power couple.

Right now, they are building Oply. Here is the pitch:

"Just like your car tells you when to change the oil, Oply uses intelligent technology to tell you what your home needs next. Your Oply Home Score tracks the health of every major system—giving you predictive insights and helping you fix issues early with vetted pros, all in a tap. Oply thinks, predicts, and acts for you—so you can enjoy your home with peace of mind."

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Lisa is one of the few 2x guests on the show. She is the head of Search Fund lending at Live Oak Bank, one of the top SBA lenders in the country, and a premier expert on loans for buying small businesses.

She also loves to work with veterans and I had her on the show to talk about why.

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Matthew talks about transitioning from the Navy to the VA and then ending up in software sales.

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Rob retired from the Army as a Special Forces officer and then spent time working with a veteran transition nonprofit. He was often the one raising money and that put me in contact with a lot of high-net-worth individuals.

After a bit, they started to ask him "Do you think you can do what we did? Buy businesses?"

He said yes, got his first investors, and started getting to work.

Listen in to hear how.

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Jack is an Air Force veteran who went to HBS.

He was told "everyone thinks of veterans as "leaders" but don't let that define you"

Turns out, Jack liked leading people. He liked being labeled a "leader." So he made some career pivots and ended up managing a $500 million business for a PE fund.

Listen in to hear his story.

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Jason Anderson is a former Air Force O-6 who retired from the military and started what looked like was his dream job.

• Business development in a sector of the Air Force he knew
• Got to live in Japan
• Making GREAT money

But he realized he didn't feel like he was really going to succeed in the role and was not getting the feeling he wanted from his work.

So he started looking into the veteran transition process and really started to appreciate the MASSIVE jump that someone needed to make to have a successful transition.

Through this journey, he founded PreVeteran. They run highly professional courses that help you go through the journey from military to civilian, backed by data and corporate learnings. It's the real deal.

Listen in to hear Jason's story and what makes PreVeteran unique.