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 revenue
• The unique San Diego ADU play turning houses into multifamily cash flow
• His raw story of loss, suicidal thoughts, and the unexpected power of flying
• Why he now measures success with two words: be there

Alan 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.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. 

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 instinct
• What partnership looks like when one founder is in the dark and the other has to carry the light
• And 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.com

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 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 leads
• What it means to build a business without becoming the brand
• Why letting your kids see your flaws might be the best kind of legacy
• How faith and fatherhood redefined what “enough” actually looks like
• And what happens when presence becomes more important than progress

There’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 expect
• The emotional cost of chasing more when you don’t have to
• How client longevity became a reflection of personal legacy
• And what it really takes to build something that doesn’t just succeed, but sustains

Featuring 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 title

Brady 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.com

If 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.