Success, Setbacks & Starting Over with Dave Denniston

What happens when your biggest leap of faith drops you straight into a financial free fall?In this raw and reflective conversation, Drew sits down with financial planner and land investor Dave Denniston to unpack the hidden cost of chasing big dreams. From a $3 million acquisition gone sideways to ten years of rebuilding from the ashes, Dave opens up about what it really means to lead through uncertainty, carry the weight of a team, and still try to be a present father.They talk cold plunges, calendar stress, aging ambition, and the hard truth that success doesn’t always feel how you thought it would. If you've ever asked yourself—"Is this it?"—this episode will feel like a mirror and a map.Along the way, Dave shares how his faith shaped his entrepreneurial journey, the mental load of leadership, and the moment that made him cry harder than he ever expected: watching his daughter run her final high school race.💬 This one’s for the men who have “made it”—and quietly wonder if they’ve lost themselves in the process.Mentioned in the episode:Dave’s event for land investors: landunconference.comDave’s leadership platform: leadershipinland.comContact: [email protected] for financial planning inquiriesYou’ve built the life everyone else wanted. Now it’s time to ask what you want. Thanks for being with us on The Other Side of Enough. This isn’t the end of the conversation—it’s the beginning of your next summit.