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Transition Checklist for the Entrepreneur

Episode 010

After 22 years in the Navy as an EOD (explosive ordinance disposal) officer, John Alford retired and quickly discovered there was no set of instructions to guide one in the transition from a highly structured system, like the military, to the life of an entrepreneur. John never had to write a resume or negotiate a salary until his mid-forties. He found himself in the position of having all the skills and experience to complete the work as a private contractor while being up against a steep learning curve for developing the skills to actually negotiate and keep the contract.

"Having to go from a set pay to a band or a scale that was negotiable was a very big deal."

John speaks very openly about the seemingly random knowledge gaps he faced, having doubts about whether or not he could even make it as an entrepreneur, and how he was inspired by watching his mother build a tutoring business after years of being a school teacher.

John Alford is an entrepreneur who works on a variety of defense contracts and he and Camille are both a part of the Five Rings Financial team. John is happy to talk with other veterans looking to transition. He can be reached through his Facebook and LinkedIn profiles or by emailing


John wasn’t so keen on wearing a costume but he was inspired to don a bow tie for our recording which you can see in the video. I chose to dress as a fictional military officer turned entrepreneur, Zoë Washburne, from one of my favorite shows, Firefly. When I requested a head shot from John to include with my posts he sent a fabulous pic from his childhood. It’s on Instagram.

Follow the show on Instagram @moneyheartshow to see more pics of my costumes from each episode.



Money Mantra: I feel comfortable asking questions about money.


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