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]’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.