The Other Side of Enough

• 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 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 waysThis 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 LinkedInThis 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.

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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 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.

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• 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 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.comDave’s leadership platform: leadershipinland.comContact: [email protected] for financial planning inquiries

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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 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

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• 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 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 emptyThe hidden fear behind creative side projectsHow imposter syndrome shows up even after multiple winsWhat it really takes to feel alive as a father, builder, and believerThe spiritual practices that keep Meir grounded in the chaosAnd why sometimes, choosing the unconventional path isn’t a flex—it’s survivalThis is a conversation about identity, legacy, and the tension between being deeply present... and endlessly driven.🔗 Learn more from Meir:Twitter: x.com/landmeirResort: modernescapes.comInstagram: instagram.com/mirrorvillasCollaborate: [email protected]

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