The Other Side of Enough cover art

The Other Side of Enough

The Other Side of Enough

By: Drew Haney
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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.

© 2025 The Other Side of Enough
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Episodes
  • When Enough Still Isn’t It with Ben Gallant
    Jun 4 2025

    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

    Show More Show Less
    1 hr and 6 mins
  • What Happens After You Win the Hustle? with Meir Shemtov
    May 28 2025

    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: meir@lotofland.com
    Show More Show Less
    59 mins
  • Is Obsession a Superpower or a Warning Sign? with Josiah Ronco
    May 21 2025

    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: josiah@acrevault.com

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

    Show More Show Less
    1 hr and 44 mins

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