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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
13 episodes
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
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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