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Life After the Military: Jason Skeesick’s Journey to Building a Thriving CrossFit Gym


Life After the Military: Jason Skeesick’s Journey to Building a Thriving CrossFit Gym

By , February 17, 2023

Jason Skeesick is a serial entrepreneur who has built multiple businesses, including a CrossFit Gym in Chicago. He spent four years in the US Army and has a finance degree, giving him the skills to maximize the value of his businesses.

Jason Skeesick had all the energy in the world, but not enough focus or direction. He joined the military, where he gained invaluable discipline and hard work. After leaving the military, Jason managed to get a job in finance and started a CrossFit Gym in a warehouse. He and two other veterans bought the space for only $1,000 a month, and the three of them ran the business together. When they offered Jason the opportunity to buy them out, he couldn’t imagine waking up the next day without the tribe he had created, so he accepted the offer. He invested in a coaching program, implemented an acquisition system, and tracked key performance indicators, and soon his small business was bringing in $90,000 a month. His hard work paid off and everyone involved made money, which

In this episode, you will learn the following:

1. How Jason Skeesick went from joining the military to becoming a successful entrepreneur.

2. The systems and strategies he used to turn his CrossFit business from a “pond” into a “pool”.

3. How he transitioned from running a fitness business to becoming a business coach.

For more on this topic and perspective, check out this episode on Succession Plus Youtube Channel and Exit Insights Spotify.


 View jason’s Linkedin Profile

Darryl Bates-Brownsword

Darryl Bates-Brownsword

CEO | Succession Plus UK

Darryl is a dynamic, driven Business Mentor and Coach with over 20 years of experience and passion for creating successful outcomes for founder-led businesses. He is a great connector, team builder, problem solver, and inspirer – showing the way through complexity to simplicity.

He has built 2 international multi-million turnover businesses; one now operating in 16 countries. His quick and analytical approach cuts through to the core issues quickly and identifying the context. He challenges the status quo and gets consistent, repeatable and reliable business results.

Originating in Australia, Darryl’s first career was as an Engineer in the Power Industry. Building businesses brought him to the UK in 2003 where he quickly developed a reputation for combining systems thinking with great creativity to get results in challenging situations.

A keen competitive cyclist, he also has a B Eng (Mech) Engineering and an MBA.