Cole (caller)
Part-owner of a property management company from Springfield, Missouri, who calls the show to weigh whether to leave his growing business to help his father's struggling trucking company; appears as a featured caller.
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27 snips
Feb 4, 2026 • 51min
Should I Take on a Leadership Role Again? (I Failed Last Time)
Luis, owner of a contracting business now running remotely from Guatemala, asks about leaving operations in his team’s hands while doing mission work. Cole, part-owner of a growing property management company from Springfield, debates whether to leave to rescue his father’s struggling trucking firm. They discuss weighing long-term tradeoffs, diagnosing failing businesses, and leading remotely with trust and clear rhythms.
