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The Other Side of Enough
You spent years building—your business, your wealth, your reputation. You did what most people only dream of.
And then… it happened.
You hit your number. You got the house. The freedom. The status.
But instead of pure satisfaction, there’s this nagging question you didn’t expect:
Now what?
Welcome to The Other Side of Enough—a podcast for high-achievers who’ve made it, but aren’t done yet. Hosted by entrepreneur and investor Drew Haney, this show explores the unspoken side of success: fulfillment, identity, and purpose after the grind.
Episodes
23 episodes
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 ...
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Season 1
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Episode 23
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1:20:41
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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...
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Season 1
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Episode 22
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1:16:11
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 scaling an $16M car dealer...
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Season 1
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Episode 21
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1:04:59
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 cha...
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Season 1
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Episode 20
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1:02:49
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?&n...
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Season 1
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Episode 19
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1:00:21
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 t...
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Season 1
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Episode 18
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1:08:53
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 into land. And the slow climb ...
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Season 1
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Episode 17
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1:04:08
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 pioneer turned land investor and...
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Season 1
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Episode 16
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1:39:03
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 built a 30-year business by doin...
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Season 1
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Episode 15
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32:21
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 episode, Brady unp...
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Season 1
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Episode 14
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1:21:57
Kevin Rockwood on Losing Flow, Making Millions, and Feeling… Meh
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 l...
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Season 1
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Episode 13
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1:14:42
Logan Swanson on Burnout, Defaults, and Building Beyond the Grind
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 r...
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Season 1
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Episode 12
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1:11:59
Success, Setbacks & Starting Over with Dave Denniston
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 o...
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Season 1
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Episode 11
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1:17:46
When Enough Still Isn’t It with Ben Gallant
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 y...
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Season 1
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Episode 10
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1:05:45
What Happens After You Win the Hustle? with Meir Shemtov
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 s...
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Season 1
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Episode 9
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58:58
Is Obsession a Superpower or a Warning Sign? with Josiah Ronco
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. ...
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Season 1
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Episode 8
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1:43:55
Building Businesses, Losing Presence: Can You Have Both? with Travis King
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 fath...
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Season 1
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Episode 7
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1:03:34
What If Success Leaves You Feeling Numb? with Seth Williams
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 epis...
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Season 1
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Episode 6
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1:16:07
When Success Isn’t Enough: Eric Wong on Surrender & Joy
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 ent...
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Season 1
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Episode 5
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1:17:55
When Success Feels Like a Better Hamster Wheel with Justin Sliva
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 slo...
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Season 1
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Episode 4
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1:02:51
Jeff Hughen on Building Wealth, Burning Out, and Starting Over
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 episod...
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Season 1
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Episode 3
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58:54
“When Success Feels Like a Trap” with Mason McDonald
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 operati...
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Season 1
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Episode 2
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1:01:42
What Comes After “Made It”? ft. Kevin Rockwood & Justin Piché
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 c...
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Season 1
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Episode 1
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1:14:44