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Why do smart STR founders break before their P&L does? In high growth short term rentals, the real risk is not the market, it is how leaders think, decide, and behave under sustained pressure. In this episode of STR Global Unlocked, Simon Lehmann sits down with personal CEO coach Gary Cohen to unpack what actually causes leaders in hospitality and short term rentals to crack, how ego quietly distorts decision making, and what it takes to build a business that no longer depends on the founder as the bottleneck. Gary has coached CEOs, founders, and executive teams across fast scaling industries. Here he translates that experience to the realities of short term rentals and hospitality leadership, where growth, investor expectations, and operational complexity collide. Timestamps 00:00 Why STR Leaders Crack Under Pressure Before Strategy Fails 02:20 Rapid Fire: Clarity, Curiosity and Trust in Leadership 03:30 Scaling STR: What Changes First in a Leader 05:33 What Leaders Feel First Under Market Pressure 10:24 High-Velocity STR: How Too Many Ideas Kill Decision Quality 14:19 Decisiveness vs Reactivity: Why STR Leaders Become the Bottleneck 18:10 The Hidden Human Cost of Scaling STR 22:23 The Two-Service Trap That Breaks Growing STR Companies 24:44 Why “We’re a Family” Is a Dangerous Culture Myth in STR 33:11 Ego vs Humility: The Leadership Ridgeline in STR 37:23 Architecting a Business That Does Not Depend on the Founder 41:18 AI Is Not Advanced Google: How STR Leaders Should Really Use It 45:59 Conclusion Questions we answer in this episode: Are short-term rentals replacing traditional multifamily real estate? Why is institutional capital cautious about investing in short-term rentals? Is lease arbitrage still a viable strategy for STR operators? How do investors underwrite risk differently in STR vs multifamily? Can flexible living increase yields without increasing volatility? Resources Connect with Gary Cohen on LinkedIn [ / garycohen ] to learn more about CO2 Coaching [https://co2coaching.com]. 📤 If this episode helped you, hit Subscribe and share it with a colleague navigating the future of short-term rentals. Stay connected: Apple Podcasts: https://podcasts.apple.com/us/podcast... Spotify: https://open.spotify.com/show/3kke4wO... Youtube: • STR Global Unlocked with Simon Lehmann: Un... Website: https://www.ajlatelier.com/podcasts Newsletter: https://str-global-unlocked.beehiiv.com/