JT Olmstead on Selling His SaaS, Starting Over, and the Myth of Doing It All

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 “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.

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 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.

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, 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.

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 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.

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 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.properties [https://olmsted.properties] 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.