#210: Hot Tubs, AI, and the Death of Easy Airbnb Money - Caleb Shore

What does it actually take to win in short-term rentals in 2026 — and is it even worth it? In this episode, Chris sits down with Caleb Shore, co-founder of My Tripify, a Charlotte-based short-term rental management company overseeing ~50 Airbnb properties. Caleb has been in the game since 2020 and has watched the market shift from "throw furniture in a house and profit" to a full-blown hospitality business requiring serious capital and strategy. In this episode you'll learn: Why only 1–2 out of 400–500 properties analyzed weekly are actually viable for short-term rental The amenities with the highest ROI right now (hot tubs, saunas, string lights) How Caleb built a team of 5 and is systematically removing himself from operations Why rental arbitrage is illegal in North Carolina — and what to do instead How Caleb uses AI to run listing optimization and rebuild his entire company website What beginner investors should do instead of jumping straight into STRs If you're thinking about short-term rentals as a wealth-building strategy, listen to this before you spend a dime. 🔗 Connect with Caleb Shore: Instagram: @calebwshore My Tripify: @mytripify 🎙️ Follow Chris: Instagram: @chris.reichenbach TikTok: @chris.reichenbach #ShortTermRentals #Airbnb #RealEstateInvesting #STRInvesting #RealEstatePodcast #LeadwayPodcast #AirbnbHost #PassiveIncome #RealEstateStrategy #WealthBuilding #MyTripify #CharlotteRealEstate #FinancialFreedom #Entrepreneurship #PropertyManagement #AIinBusiness #BuyBackYourTime #RealEstateTips #EscapeThe9to5 #InvestingTips