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The Other Side of Enough
Drew Haney
23 episodes
1 month ago
You can flip phones at 14, land at 21, and close million-dollar deals before 30—and still wonder if it’s enough. In this conversation, Clint Turner shares how his obsession with deals took him from iPhones in a school cafeteria to complex distressed real estate plays. But the story isn’t just about scaling profits—it’s about facing burnout, chasing stimulation, and learning to slow down when success itself becomes unsustainable. We talk deal junkie highs, the hidden costs of coaching, why “fl...
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You can flip phones at 14, land at 21, and close million-dollar deals before 30—and still wonder if it’s enough. In this conversation, Clint Turner shares how his obsession with deals took him from iPhones in a school cafeteria to complex distressed real estate plays. But the story isn’t just about scaling profits—it’s about facing burnout, chasing stimulation, and learning to slow down when success itself becomes unsustainable. We talk deal junkie highs, the hidden costs of coaching, why “fl...
Show more...
Arts
Episodes (20/23)
The Other Side of Enough
Clint Turner on Obsession, Burnout, and Building Beyond Millions
You can flip phones at 14, land at 21, and close million-dollar deals before 30—and still wonder if it’s enough. In this conversation, Clint Turner shares how his obsession with deals took him from iPhones in a school cafeteria to complex distressed real estate plays. But the story isn’t just about scaling profits—it’s about facing burnout, chasing stimulation, and learning to slow down when success itself becomes unsustainable. We talk deal junkie highs, the hidden costs of coaching, why “fl...
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1 month ago
1 hour 20 minutes

The Other Side of Enough
From Peru to Profit: Jason Wollbrink on Faith, Marriage, and Enough
What if the life you built wasn’t the life that built you? Jason Wollbrink left the Midwest to plant churches in Peru—only to discover that success isn’t about the house you flip or the money you make, but the presence you bring to the people you love. In this episode, Drew and Jason go deep on the questions high-achievers rarely ask out loud: Can you lead in business and at home without burning out either one?Why does financial freedom often feel hollow without identity rooted in something d...
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2 months ago
1 hour 16 minutes

The Other Side of Enough
ADUs, Airplanes, and the Weight of What’s Next with Alan Underwood
What happens when selling cars turns into building communities—and facing yourself along the way? In this episode, Drew sits down with Alan Underwood, whose path runs from managing pizza buffets to scaling an $16M car dealership, and now transforming single-family homes into multi-unit investments through San Diego’s ADU laws. But this isn’t just about spreads and construction, Alan opens up about grief, depression, and the day he nearly ended it all, before aviation and purpose gave him a ne...
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2 months ago
1 hour 4 minutes

The Other Side of Enough
Joshua Sun on Redefining Success Beyond the Mortgage Game
You can crush it in your career and still feel the pull toward something more. For 20 years, Joshua Sun built a thriving mortgage business. By all external measures he had made it. But when he saw how quickly the industry could change and how little fulfillment he felt in the work, he knew it was time to climb a different mountain. In this conversation, Joshua opens up about the pivot that took him from comfortable routine to high-stakes purpose: raising capital for creative real estate deals...
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2 months ago
1 hour 2 minutes

The Other Side of Enough
When Success Feels Heavy: Joe Roberts on Faith, Fire, and What Comes After the Climb
He built a 7-figure land business, launched a top-tier cold calling company, and co-owns a recession-proof service brand. But Joe Roberts isn’t chasing more—he’s asking better questions. What anchors you after the grind ends? For Joe, it’s faith, family, and a quiet refusal to let his identity be tied to titles—even the ones most men would kill for. In this episode, we explore what it means to lead from conviction in a world obsessed with scale. Joe shares how his years as a Marine shap...
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2 months ago
1 hour

The Other Side of Enough
JT Olmstead on Selling His SaaS, Starting Over, and the Myth of Doing It All
He scaled two businesses. Built powerful systems. And still felt spread too thin. What happens when your capacity outpaces your clarity? In this conversation, JT Olmstead unpacks the quiet cost of success split in two. He built a thriving land business and launched a software company from scratch. But eventually, something had to give. And it wasn't just time he lost. It was margin, presence, and perspective. Drew and JT dive into the myth of doing it all, the false promise of synergy, and th...
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3 months ago
1 hour 8 minutes

The Other Side of Enough
Can You Build Without Breaking? Jessey Kwong on Business, Balance & Burnout
He built the thing. Now he’s asking what it’s costing him. Before Jessey Kwong co-founded Pebble, he was running a global beauty brand out of his living room. Then came burnout. A reset. A quiet pivot into land. And the slow climb toward something that actually fit. In this episode, Jessey opens up about what most builders won’t say out loud: The early signs of emotional overload (and why they’re easy to ignore)Leading a high-talent team with no playbook, just humility and instinctWhat partne...
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3 months ago
1 hour 4 minutes

The Other Side of Enough
When Success Isn’t the Win with Buck Rizvi
He built the brands. Made the money. Interviewed the icons. So why did peace come later? In this rare, unfiltered conversation, Drew reconnects with Buck Rizvi—an Air Force veteran turned e-commerce pioneer turned land investor and founder of Ultimate Dog. But this isn’t a highlight reel. It’s the kind of conversation that happens after the conference, when the ties come off and the real questions begin. Together, they unpack: The near-collapse moment that changed how Buck leadsWhat it means ...
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3 months ago
1 hour 39 minutes

The Other Side of Enough
What Happens When You Stop Chasing More with Uncle Dave
What if you didn’t need to scale, hustle, or chase more to build a meaningful life? In this grounded and deeply human conversation, Drew sits down with his uncle Dave—a financial advisor who quietly built a 30-year business by doing things differently. No office. No ads. No ambition to scale. Just long-term relationships, flat fees, and showing up at his clients' kitchen tables. Dave shares what it was like to walk away from a safe, high-paying job to make $6,000 in his first year. He explain...
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3 months ago
32 minutes

The Other Side of Enough
When Obsession Becomes Purpose — Brady Canales on Building Hotbox
You hit your number. Built the thing. But are you actually free? Brady Canales left the Navy SEALs at 27—and found himself untethered. No mission. No team. Just a haunting question: What now? In this episode, Brady unpacks how a garage-built prototype and a life-saving ritual turned into Hotbox Sauna, one of the most respected wellness brands on the market. We go deep on: – Why most “premium” saunas are secretly toxic – The hidden crisis behind elite military transitions – ...
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4 months ago
1 hour 21 minutes

The Other Side of Enough
Kevin Rockwood on Losing Flow, Making Millions, and Feeling… Meh
You finally have the time and money you wanted. So why does it still feel heavy? In this episode, Drew sits down with Kevin Rockwood, co-founder of Pebble and full-time dad, for a raw and revealing conversation about what success feels like when no one’s watching. They unpack the emotional weight of hitting autopilot in your business, the guilt of “not doing enough” even when everything’s working, and why freedom without purpose can feel more stressful than the grind ever did. Kevin gets v...
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4 months ago
1 hour 14 minutes

The Other Side of Enough
Logan Swanson on Burnout, Defaults, and Building Beyond the Grind
What if the real flex isn’t the exit, but how you live after? In this raw, quietly radical conversation, Drew sits down with Logan Swanson, a man who's built land businesses, funding firms, and even a digital marketplace, only to realize that the real win isn’t more... it’s better. Together, they unpack the chaos of early entrepreneurship, the unexpected grief of hitting your goals, and the sacred tension between ambition and enough. Logan gets honest about failed projects, the “default seaso...
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4 months ago
1 hour 11 minutes

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 plunge...
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4 months ago
1 hour 17 minutes

The Other Side of Enough
When Enough Still Isn’t It with Ben Gallant
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 bu...
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5 months ago
1 hour 5 minutes

The Other Side of Enough
What Happens After You Win the Hustle? with Meir Shemtov
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 o...
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5 months ago
58 minutes

The Other Side of Enough
Is Obsession a Superpower or a Warning Sign? with Josiah Ronco
You built the life. But why does comfort feel so... flat? In this raw, revealing conversation, land investor and former touring guitar tech Josiah Ronco opens up about what happens after the financial breakthrough. From working with OneRepublic to running one of the top land businesses in Florida, Josiah’s income 10x’d—but so did his inner questions. Drew and Josiah explore: The unexpected downside of successWhether work-life balance is a myth (or just a buzzword)Why boredom on vacation might...
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5 months ago
1 hour 43 minutes

The Other Side of Enough
Building Businesses, Losing Presence: Can You Have Both? with Travis King
You finally have what you worked for—so why does more still feel like... not enough? In this conversation, Drew Haney sits down with investor and mentor Travis King to unpack what happens after the escape plan works. They talk fatherhood, faith, and the friction between achievement and presence—revealing what success actually looks like once the scoreboard stops mattering. Travis opens up about: The slow burnout of "time freedom" without purposeWhy building a business that runs itself can lea...
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5 months ago
1 hour 3 minutes

The Other Side of Enough
What If Success Leaves You Feeling Numb? with Seth Williams
What if the real risk isn’t failing—but staying in what no longer fits? You build the brand. You hit the numbers. And somewhere along the way, the thing that gave you purpose starts to feel like a performance. In this episode, Seth Williams—land investor and founder of REtipster—opens up about the hidden cost of success when identity, obligation, and achievement get tangled. From building one of the most respected platforms in real estate education to quietly stepping back from the very thing...
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6 months ago
1 hour 16 minutes

The Other Side of Enough
When Success Isn’t Enough: Eric Wong on Surrender & Joy
What if fulfillment doesn’t come from scaling—but from surrender? In this rich and deeply personal episode, Drew reunites with longtime friend and former Army roommate Eric Wong—a West Point grad, land investor, and neuroscience-obsessed entrepreneur—who shares why having enough money doesn’t mean feeling enough. And why the most powerful work he’s done lately isn’t in business… but in his inner life. Together, they unpack: Why success alone won’t satisfy—and why it’s not supposed to The n...
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6 months ago
1 hour 17 minutes

The Other Side of Enough
When Success Feels Like a Better Hamster Wheel with Justin Sliva
You made the money. Now what? For Justin Sliva, a former railroad exec turned land investor and father of three, the answer wasn’t more deals or bigger houses—it was coaching his kids’ soccer team, skipping the Rolex, and learning to slow down without shutting off. In this intimate conversation with Drew, Justin opens up about what happens after financial freedom: the thrill of building, the ache of boredom, and the raw honesty of wondering if you’re just on a fancier hamster wheel. They u...
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6 months ago
1 hour 2 minutes

The Other Side of Enough
You can flip phones at 14, land at 21, and close million-dollar deals before 30—and still wonder if it’s enough. In this conversation, Clint Turner shares how his obsession with deals took him from iPhones in a school cafeteria to complex distressed real estate plays. But the story isn’t just about scaling profits—it’s about facing burnout, chasing stimulation, and learning to slow down when success itself becomes unsustainable. We talk deal junkie highs, the hidden costs of coaching, why “fl...