The Other Side of Enough

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 like when no one’s watching.

They unpack the emotional weight of hitting autopilot in your business, the guilt of “not doing enough” even when everything’s working, and why freedom without purpose can feel more stressful than the grind ever did.

Kevin gets vulnerable about:
-Losing his flow state after stepping out of daily development
-Balancing guilt, growth, and gratitude as a founder with flexibility
-Wrestling with lifestyle creep, fatherhood, and the myth of early retirement
-Cultural clashes in marriage, money, and multigenerational expectations
-The quiet cost of free time and how he’s rebuilding fulfillment in small, intentional ways

This isn’t a hustle-harder episode. It’s an honest look at what happens after the big goals get crossed off and how to reorient when your calendar, bank account, and soul aren’t in sync.

🎙 Guest: Kevin Rockwood
🏗 Platform: pebblerei.com
📺 YouTube: Search "Pebble REI" for monthly episodes
📱 Connect: Find Kevin on LinkedIn

This is what it sounds like when two high performers talk about what really keeps them up at night.

Hit play if you’ve ever felt guilty for not grinding and wondered if peace is something you have to earn.

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 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 realize that the real win isn’t more... it’s better. Together, they unpack the chaos of early entrepreneurship, the unexpected grief of hitting your goals, and the sacred tension between ambition and enough.

Logan gets honest about failed projects, the “default season” of 2024, and why peace, not profit, is his new north star. From surviving restaurant burnout and parenting three kids under six, to building a coffee shop just for the joy of it, this episode goes where most “success stories” won’t.

If you’ve ever hit a big milestone and still felt restless, this is your blueprint for what comes next.

🎙 Guest: Logan Swanson
 Listen to his podcast: The Land Fixer
Contact: [email protected]

🎧 Listen now because success isn’t the end. It’s the start of a different question.

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 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 of chasing big dreams. From a $3 million acquisition gone sideways to ten years of rebuilding from the ashes, Dave opens up about what it really means to lead through uncertainty, carry the weight of a team, and still try to be a present father.

They talk cold plunges, calendar stress, aging ambition, and the hard truth that success doesn’t always feel how you thought it would. If you've ever asked yourself—"Is this it?"—this episode will feel like a mirror and a map.

Along the way, Dave shares how his faith shaped his entrepreneurial journey, the mental load of leadership, and the moment that made him cry harder than he ever expected: watching his daughter run her final high school race.

💬 This one’s for the men who have “made it”—and quietly wonder if they’ve lost themselves in the process.

Mentioned in the episode:

• Dave’s event for land investors: landunconference.com
• Dave’s leadership platform: leadershipinland.com
• Contact: [email protected] for financial planning inquiries

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 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 you were told to want… and quietly wondering why it doesn’t feel better.

They explore the stages high-achieving men face—from golden handcuffs to entrepreneurial freedom—and what happens after you "make it." This episode tackles the real questions: Can you scale a business and stay present at home? Is freedom always fulfilling? And what does legacy actually mean when you're already financially set?

If you’ve ever looked around your “dream life” and felt a surprising emptiness, this one’s for you.

🎧 Guest: Ben Gallant
 Find him on X: @BenRGallant
Instagram: @ben.gallant

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 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 success: how even after building multiple businesses, exiting to WeWork, and selling out a luxury resort via Indiegogo… he still wrestles with boredom, burnout, and the fear of it all vanishing overnight.

Drew and Meir go deep on what most high performers won’t say out loud:

• Why scaling a business can leave you feeling empty
• The hidden fear behind creative side projects
• How imposter syndrome shows up even after multiple wins
• What it really takes to feel alive as a father, builder, and believer
• The spiritual practices that keep Meir grounded in the chaos
• And why sometimes, choosing the unconventional path isn’t a flex—it’s survival

This is a conversation about identity, legacy, and the tension between being deeply present... and endlessly driven.

🔗 Learn more from Meir:

• Twitter: x.com/landmeir
• Resort: modernescapes.com
• Instagram: instagram.com/mirrorvillas
• Collaborate: [email protected]

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 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. From working with OneRepublic to running one of the top land businesses in Florida, Josiah’s income 10x’d—but so did his inner questions.

Drew and Josiah explore:

• The unexpected downside of success
• Whether work-life balance is a myth (or just a buzzword)
• Why boredom on vacation might be the red flag no one's talking about
• How entrepreneurs and addicts might not be as different as you think
• The weird joy of chasing deals, not dopamine

What makes this episode different? It’s not about ambition—it’s about what happens when ambition succeeds.

Josiah doesn’t sell you a dream. He talks about running a lean, high-performing team, the fears that come with sudden wealth, and why he’d rather hike into the woods than buy a Ferrari.

📬 Reach out or send deals: [email protected]

Warning: This one may cause you to rethink your version of “enough.”

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 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 fatherhood, faith, and the friction between achievement and presence—revealing what success actually looks like once the scoreboard stops mattering.

Travis opens up about:

• The slow burnout of "time freedom" without purpose
• Why building a business that runs itself can leave you restless
• The emotional cost of coaching—and why he still does it anyway
• Letting go of shiny objects and staying loyal to your “main thing”
• How being fully present with your kids requires more than just showing up

This isn’t about hustle. It’s about the harder work of figuring out who you are—once you’re no longer defined by the grind.

🔗 Learn more: TravisKing.com
🎙 Listen to Travis’s podcast: The King Show on Apple & Spotify

🎧 Tap into the truth behind success—stream this episode now.

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 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 episode, Seth Williams—land investor and founder of REtipster—opens up about the hidden cost of success when identity, obligation, and achievement get tangled. From building one of the most respected platforms in real estate education to quietly stepping back from the very thing that made him “successful,” Seth shares the inner shifts that most entrepreneurs don’t say out loud.

We talk about:
– The moment you realize your business is running you
– Emotional bandwidth, fatherhood, and redefining ambition
– Letting go of the expert role to rediscover who you actually are
– The difference between fulfillment and happiness—and why it matters
– Why walking away isn’t weakness—it’s mastery

This isn’t about giving up.
It’s about knowing when a version of you has run its course.

Welcome to the Other Side of Enough.

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 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 entrepreneur—who shares why having enough money doesn’t mean feeling enough. And why the most powerful work he’s done lately isn’t in business… but in his inner life.

Together, they unpack:

Why success alone won’t satisfy—and why it’s not supposed to

The neuroscience behind joy, burnout, and the real “balance” high-performers crave

How to pursue God without turning it into a checklist

Dopamine, decision fatigue, and what makes people actually happy

The myth of financial arrival—and how surrender is the actual next level

Eric shares his journey from Army officer to full-time land investor to spiritual mentor, and how a powerful heaven-time practice reshaped everything—from his business rhythms to how he parents. This one’s not just insightful—it’s grounding.

📍 Connect with Eric at:
Email: [email protected]
Text: 719-377-2333
Learn more about the Kingdom Movers Mastermind, a space for faith-driven entrepreneurs building for eternity.

🎧 Listen now—this conversation could change how you think about success, faith, and what you’re 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. 

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 slow down without shutting off.

In this intimate conversation with Drew, Justin opens up about what happens after financial freedom: the thrill of building, the ache of boredom, and the raw honesty of wondering if you’re just on a fancier hamster wheel.

They unpack:

The emotional cost of being "self-made"

Why most high achievers can’t sit still—and probably never will

How Justin redefined legacy after meeting his biological father at age 36

What true wealth looks like when your six-year-old hands you a grilled cheese from the back of a food trailer

This isn’t just a business episode. It’s a soulful, late-night-level talk about what actually matters once you’ve stopped chasing and started choosing.

🎙 Listen to Justin’s podcast: Casual Fridays REI
📅 Catch him live at: milkhoney.land + landunconference.com
📲 Connect: Justin Sliva on Facebook

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.