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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.
The Other Side of Enough
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 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