The Other Side of Enough Podcast
1) 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 iP...Show More
2) 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...Show More
3) 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 sc...Show More
4) 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...Show More
5) 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 ...Show More
When Success Feels Heavy: Joe Roberts on Faith, Fire, and What Comes After the Climb
1:00:21 | Aug 6th, 2025
6) 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 suc...Show More
JT Olmstead on Selling His SaaS, Starting Over, and the Myth of Doing It All
1:08:53 | Jul 30th, 2025
7) 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...Show More
Can You Build Without Breaking? Jessey Kwong on Business, Balance & Burnout
1:04:08 | Jul 23rd, 2025
8) 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 p...Show More
9) 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 b...Show More
10) 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...Show More