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The Other Side of Enough
You spent years building—your business, your wealth, your reputation. You did what most people only dream of.
And then… it happened.
You hit your number. You got the house. The freedom. The status.
But instead of pure satisfaction, there’s this nagging question you didn’t expect:
Now what?
Welcome to The Other Side of Enough—a podcast for high-achievers who’ve made it, but aren’t done yet. Hosted by entrepreneur and investor Drew Haney, this show explores the unspoken side of success: fulfillment, identity, and purpose after the grind.
The Other Side of Enough
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.com
- Dave’s leadership platform: leadershipinland.com
- Contact: kara@daviddeniston.com for financial planning inquiries