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#342: Walking Away From a Career He Loved to Be a More Present Dad with Jacob Stevenson
Description
What happens when the career you love starts costing you moments you can’t get back?
Jacob “Jake” Stevenson spent 12 years coaching college wrestling. But when his wife called to tell him their son had won his first wrestling match, Jake was somewhere else—coaching someone else’s kid. He was crying in the corner of a match, realizing his future might need to look different.
In episode 342 of The Kash and Dash Show, hosts Ted Kaasch & Owen Dashner sit down with Jake to unpack his move from college coaching into insurance agency ownership and a 17-property real estate portfolio.
Jake shares the messy parts, too: an eight-property partnership that fell apart, an Airbnb guest situation that brought the cops and angry neighbors, and the challenge of handing off work when you’re used to doing everything yourself.
In this episode:
• The moment Jake began questioning his future in coaching.
• Buying an insurance agency without a background in the industry.
• Building a portfolio of college rentals, small multifamily properties, and commercial space.
• Using a virtual assistant team to handle Airbnb guest communication.
• Why friendship and trust weren’t enough to make a business partnership work.
• Growing businesses with his wife, Jess, while raising four kids.
• Defining success around the life you actually want to live.
There are deals, hard lessons, and plenty of laughs—but the question underneath it all is simple: Is the business you’re building giving you more of the life you want?
Hear more from Jake on his podcast, On the Same Team, available on Spotify, Amazon, and other podcast platforms.
Subscribe to The Kash and Dash Show, share this episode with someone weighing a career change, and tell us in the comments: What’s one moment you refuse to let work make you miss?
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