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 “flow state” matters more than spreadsheets, and how fatherhood reshapes what achievement really means.Clint doesn’t pitch a course or sell a product here. He just sits down for a raw, unfiltered look at what it’s like to build fast, burn out hard, and then ask the harder question: Now what?Listen to the full episode now—this one goes far beyond the numbers.You’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.

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 deeper?What does it take to stop living as a caretaker—and start living as a king?Jason shares raw lessons from marriage struggles, near-death experiences, and building a thriving land business while keeping faith and family at the center.If you’ve ever wondered whether “enough” is really enough, this is the conversation that won’t leave you the same.You’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.

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 new reason to keep climbing.You’ll hear:How Alan built and sold a dealership doing $16M in annual revenueThe unique San Diego ADU play turning houses into multifamily cash flowHis raw story of loss, suicidal thoughts, and the unexpected power of flyingWhy he now measures success with two words: be thereAlan is the managing partner at Momentum Capital. To learn more, visit mmtmgrp.com or connect with him on Instagram, Facebook, and LinkedIn at @thealanunderwood.This is real talk about money, meaning, and the choices that define us.You’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.

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, keeping families in their homes, and funding projects that fight human trafficking and support domestic violence survivors. We explore what it means to balance ambition with presence, how faith shapes his decisions, and the daily choices that keep him engaged at home while building something bigger than himself.Connect with Joshua on Instagram or YouTube at @JoshuaSun26 to see how he is merging business, impact, and intentional living.Listen in and ask yourself: what is the “more” you are really chasing?You’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.

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 shaped how he builds teams, fires people with dignity, and resists the trap of overidentifying with the uniform—or the business card.We talk about boredom, burnout, hormone health, and what happens when your drive stays high but your meaning runs dry.Joe Roberts is the founder of LandCaller and co-owner of a restoration company in North Carolina. Learn more at landcaller.com.🎧 You’ve made it. Now what?You’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.

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 the hard choice to walk away from what no longer fits. They talk about the mental drag of being good at too many things, the hidden math behind divided focus, and the freedom that comes from choosing one path with both feet.You’ll hear stories from JT’s early land days, including the time he launched a Honda Fit across a desert ravine, and the quieter moments where faith, family, and alignment pulled him back to center.If you’ve been asking yourself whether something needs to go so you can grow, this is your sign to pause and listen.🎙 Guest: JT Olmstead📍Contact: https://olmstead.propertiesYou’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.

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 partnership looks like when one founder is in the dark and the other has to carry the lightAnd the fear behind success: What if I never feel like I’ve done enough?We also talk work-life rhythm, identity shifts, and how a kid from Vancouver who paints Transformers and builds terrariums found his own version of excellence without losing himself in the process.This isn’t about building a business. It’s about staying human while you do.👤 Featuring Jessey Kwong, co-founder of Pebble and writer at imhorribleatbusiness.substack.comYou’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.

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 to build a business without becoming the brandWhy letting your kids see your flaws might be the best kind of legacyHow faith and fatherhood redefined what “enough” actually looks likeAnd what happens when presence becomes more important than progressThere’s no blueprint here—just a deep dive into the messy, meaningful side of success.Featuring Buck Rizvi Learn more: https://ultimatedog.com Contact Buck: [email protected]🎧 Listen in. This is the stuff most men never say out loud.You’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.

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 explains how he coached clients through the 2008 crash without losing their trust—or his own peace of mind. And he reveals why he stopped accepting new business at 55, choosing intentional decline over endless expansion.They explore:Why enough is often quieter than you expectThe emotional cost of chasing more when you don’t have toHow client longevity became a reflection of personal legacyAnd what it really takes to build something that doesn’t just succeed, but sustainsFeaturing Dave Haney—mentor, husband, father, and a man who redefined success by living it.Listen in to hear the quiet power of a life built on purpose, not pressure.You’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.

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 – Bootstrapping without burnout (and without selling out) – Copycats, manufacturing chaos, and staying obsessed when it’d be easier to quit – How to lead a team of older high-performers—and why trust matters more than titleBrady shares how ritual, resilience, and ruthless simplicity shaped Hotbox’s rise—from custom builds for SEAL teams to getting featured on Rogue’s website. He also opens up about marriage, identity shifts, and what it means to lead without becoming someone you hate.Guest: Brady Canales — Founder of Hotbox Sauna → Check out his product and story at thehotboxsauna.comIf you've ever wondered, "What if I build the dream and still feel empty?"—this one’s for you. Press play. Your next chapter might start here.You’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.

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 vulnerable about:-Losing his flow state after stepping out of daily development-Balancing guilt, growth, and gratitude as a founder with flexibility-Wrestling with lifestyle creep, fatherhood, and the myth of early retirement-Cultural clashes in marriage, money, and multigenerational expectations-The quiet cost of free time and how he’s rebuilding fulfillment in small, intentional waysThis isn’t a hustle-harder episode. It’s an honest look at what happens after the big goals get crossed off and how to reorient when your calendar, bank account, and soul aren’t in sync.🎙 Guest: Kevin Rockwood🏗 Platform: pebblerei.com📺 YouTube: Search "Pebble REI" for monthly episodes📱 Connect: Find Kevin on LinkedInThis is what it sounds like when two high performers talk about what really keeps them up at night.Hit play if you’ve ever felt guilty for not grinding and wondered if peace is something you have to earn.You’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.

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 season” of 2024, and why peace, not profit, is his new north star. From surviving restaurant burnout and parenting three kids under six, to building a coffee shop just for the joy of it, this episode goes where most “success stories” won’t.If you’ve ever hit a big milestone and still felt restless, this is your blueprint for what comes next.🎙 Guest: Logan Swanson Listen to his podcast: The Land Fixer Contact: [email protected]🎧 Listen now because success isn’t the end. It’s the start of a different question.You’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.

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.

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.gallantYou’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.

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 emptyThe hidden fear behind creative side projectsHow imposter syndrome shows up even after multiple winsWhat it really takes to feel alive as a father, builder, and believerThe spiritual practices that keep Meir grounded in the chaosAnd why sometimes, choosing the unconventional path isn’t a flex—it’s survivalThis is a conversation about identity, legacy, and the tension between being deeply present... and endlessly driven.🔗 Learn more from Meir:Twitter: x.com/landmeirResort: modernescapes.comInstagram: instagram.com/mirrorvillasCollaborate: [email protected]’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.

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 be the red flag no one's talking aboutHow entrepreneurs and addicts might not be as different as you thinkThe weird joy of chasing deals, not dopamineWhat makes this episode different? It’s not about ambition—it’s about what happens when ambition succeeds.Josiah doesn’t sell you a dream. He talks about running a lean, high-performing team, the fears that come with sudden wealth, and why he’d rather hike into the woods than buy a Ferrari.📬 Reach out or send deals: [email protected]: This one may cause you to rethink your version of “enough.”You’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.

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 leave you restlessThe emotional cost of coaching—and why he still does it anywayLetting go of shiny objects and staying loyal to your “main thing”How being fully present with your kids requires more than just showing upThis isn’t about hustle. It’s about the harder work of figuring out who you are—once you’re no longer defined by the grind.🔗 Learn more: TravisKing.com 🎙 Listen to Travis’s podcast: The King Show on Apple & Spotify🎧 Tap into the truth behind success—stream this episode now.You’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.

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 that made him “successful,” Seth shares the inner shifts that most entrepreneurs don’t say out loud.We talk about:– The moment you realize your business is running you – Emotional bandwidth, fatherhood, and redefining ambition – Letting go of the expert role to rediscover who you actually are – The difference between fulfillment and happiness—and why it matters – Why walking away isn’t weakness—it’s masteryThis isn’t about giving up.It’s about knowing when a version of you has run its course.Welcome to the Other Side of Enough.You’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.

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 toThe neuroscience behind joy, burnout, and the real “balance” high-performers craveHow to pursue God without turning it into a checklistDopamine, decision fatigue, and what makes people actually happyThe myth of financial arrival—and how surrender is the actual next levelEric shares his journey from Army officer to full-time land investor to spiritual mentor, and how a powerful heaven-time practice reshaped everything—from his business rhythms to how he parents. This one’s not just insightful—it’s grounding.📍 Connect with Eric at:Email: [email protected]: 719-377-2333Learn more about the Kingdom Movers Mastermind, a space for faith-driven entrepreneurs building for eternity.🎧 Listen now—this conversation could change how you think about success, faith, and what you’re really chasing.You’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.

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 unpack:The emotional cost of being "self-made"Why most high achievers can’t sit still—and probably never willHow Justin redefined legacy after meeting his biological father at age 36What true wealth looks like when your six-year-old hands you a grilled cheese from the back of a food trailerThis isn’t just a business episode. It’s a soulful, late-night-level talk about what actually matters once you’ve stopped chasing and started choosing.🎙 Listen to Justin’s podcast: Casual Fridays REI📅 Catch him live at: milkhoney.land + landunconference.com📲 Connect: Justin Sliva on FacebookYou’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.

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 ambition, identity, and “enough.”From the land flip that paid seven figures to the weight of leading too many projects at once, Jeff doesn’t hold back. They explore:The cost of skipping steps (and how it nearly broke him)What happens when a cash cow stops feeling excitingWhy obsessiveness might be a feature—not a flaw—for entrepreneursThe myth of balance, and what actually works insteadWhether you’re in your first business or your fifth, this is a behind-the-scenes look at the messy middle—and why “freedom” can sometimes feel like a full-time job.🔗 Explore Jeff’s latest venture: Bravara Home — Non-toxic kitchenware for modern families. 📩 Reach out directly: [email protected]’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.

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 realizing… this isn’t it.In this raw and reflective episode, Mason shares how walking away from a prestigious title led to flipping dirt, finding peace, and redefining legacy on his own terms. From early wins in land deals to obsessive entrepreneur tendencies, Mason and Drew dive deep into what it means to stay driven—without being driven mad.This isn’t advice. It’s honesty.To get to know more about Mason and follow his journey:📍 masonrmcdonald.com 📱 @masonrmcdonald on Instagram 🎙 Listen to his podcast The Big Picture Blueprint wherever you tune inYou’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.

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 followed wasn’t “what’s next?”—it was “who am I now?”We talk about the identity crisis that comes when performance stops being your purpose, the unexpected weight of financial freedom, and why so many high-achieving men feel more lost at the summit than they ever did on the way up.This isn’t advice. It’s honesty.To learn more about Kevin and Justin beyond this conversation, check them out here:📍Find Justin at justinpiche.com and on The Ground Game Podcast 📍Find Kevin at pebblerei.comYou’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.