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

You hit every milestone—and still feel off. Now what?

In this raw and reflective conversation, Drew Haney sits down with land investor and commercial real estate pro Ben Gallant to unpack the paradox of success: building the life you were told to want… and quietly wondering why it doesn’t feel better.

They explore the stages high-achieving men face—from golden handcuffs to entrepreneurial freedom—and what happens after you "make it." This episode tackles the real questions: Can you scale a business and stay present at home? Is freedom always fulfilling? And what does legacy actually mean when you're already financially set?

If you’ve ever looked around your “dream life” and felt a surprising emptiness, this one’s for you.

🎧 Guest: Ben Gallant
Find him on X: @BenRGallant
Instagram: @ben.gallant

You scaled the mountain—and found yourself restless at the peak.

In this raw, unfiltered conversation, Meir (land investor, serial entrepreneur, and creative mind behind Modern Escapes and LotOfLand) opens up about the paradox of success: how even after building multiple businesses, exiting to WeWork, and selling out a luxury resort via Indiegogo… he still wrestles with boredom, burnout, and the fear of it all vanishing overnight.

Drew and Meir go deep on what most high performers won’t say out loud:

• Why scaling a business can leave you feeling empty
• The hidden fear behind creative side projects
• How imposter syndrome shows up even after multiple wins
• What it really takes to feel alive as a father, builder, and believer
• The spiritual practices that keep Meir grounded in the chaos
• And why sometimes, choosing the unconventional path isn’t a flex—it’s survival

This is a conversation about identity, legacy, and the tension between being deeply present... and endlessly driven.

🔗 Learn more from Meir:

• Twitter: x.com/landmeir
• Resort: modernescapes.com
• Instagram: instagram.com/mirrorvillas
• Collaborate: meir@lotofland.com