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

About this episode

Caleb Shore discusses the evolving landscape of short-term rentals and shares insights on what it takes to succeed in the market.

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…

People in this episode

Host: Chris

Guest: Caleb Shore

Topics covered

• short-term rentals
• Airbnb
• real estate investing
• hospitality business
• AI in business
• wealth building

Keywords

• short-term rentals
• Airbnb
• real estate strategy
• investment
• hospitality
• AI
• wealth building
• North Carolina
• My Tripify

Mentioned in this episode

Organizations: My Tripify

Places: North Carolina, Charlotte

More episodes of The Leadway Wealth Builders Podcast

• #217: Don't Buy A Rental! *UNTIL* You Listen To This - Adam Balsinger · June 10, 2026 · 50 min
• #216: The Best Advice I've Gotten From Millionaires · June 3, 2026 · 18 min
• #215: Rewire Your Brain, Close More Deals — High Performance Coaching - Pat Smith · May 27, 2026 · 48 min
• #214: What Is Going On In The Charlotte Market & How To Stay Ahead - Jordan Smith · May 20, 2026 · 42 min
• #213: Your W-2 Is a Weapon — How to Build a Rental Portfolio Without Burning It Down - Cory Jacobson · May 13, 2026 · 39 min
• #212: Is Your W-2 Holding You Back? How Grant 10X'd His Portfolio When He Quit - Grant Francke · May 6, 2026 · 27 min