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 succe...

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 o...

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 hi...

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 le...

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,...

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...

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...

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 w...

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” sa...

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,...

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 s...

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 unc...

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—...

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 f...

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 downsid...

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: T...

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 t...

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 l...

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...

You made it. Now you’re spread thin, restless—and still searching. What happens when you’re a few wins in, the money’s flowing, and the only thing running faster than your business portfolio… is your brain? In this raw, real episode, Drew sits down with longtime friend and serial entrepreneur Jeff Hughen , a former airline captain turned multi-business operator, to unpack the tension between ambit...

You spent years building something. Grinding, scaling, making sure your family is set. And then… you made it. In this anonymous conversation, Kevin Rockwood and Justin Piché open up about the emotional aftermath of achievement—the quiet confusion that comes when success doesn’t feel like enough. They’ve sold companies. Hit the numbers. Built the lives they once dreamed of. But the question that fo...

You climbed the ladder. You reached the top. And then… you looked around and asked, “Why am I miserable?” Mason McDonald was 26 years old when he became one of the youngest hospital CEOs in the country—running a nine-figure operation, managing hundreds of lives, and hitting every metric of success. But what came next wasn’t fulfillment. It was high blood pressure, anxiety, and the quiet dread of r...