In this episode, we sit down with Jason, the high-flying entrepreneur behind Skydive Chesapeake, to talk about his wild journey from 20 years in the construction industry to running multiple businesses across state lines — including a skydiving company that just launched its first full season. What started as a bucket list item turned into a full-fledged business venture, and Jason shares how he made it all happen.Jason’s story is anything but ordinary. As a kid, he dreamed of becoming a Navy pilot. While life took him down a different path, he decided to chase that dream anyway — by planning to buy an actual F-18 fighter jet. Along the way, he built a thriving construction company, launched a real estate business with Airbnb properties, and now operates a staging company he hopes to scale into a franchise. In this conversation, he opens up about how important it is to hire the right people and make sure they’re in the right roles. His success, he says, wouldn’t be possible without the support of his wife and his dedicated business partner, who sold her home and moved states to help run the skydiving business. He also runs a mentorship program for young people, helping the next generation of entrepreneurs find their path. Jason shares how he’s been able to juggle it all — business, family, and personal goals — by designing a life where everything is integrated. His house, gym, and office are all in the same place, helping him stay focused and efficient. He offers insight into what it really takes to work from home without losing momentum, and how a simple mindset shift — changing “I have to” into “I get to” — changed everything. Every moment, he believes, is an opportunity — if you’re willing to flip your perspective. Don’t miss this inspiring and energizing episode.

Thanks for tuning in to B2B with Randy & Craig, where we connect with local entrepreneurs to explore their journeys and inspire others to take the leap into entrepreneurship. We’re your host, Randy Goldbaum and Craig Rappaport.

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