Short-Term Rentals at Scale: Luiz Batalha on Upstay’s $1B Hospitality Engine

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Two Tokens Short

Robert Delarosa

23 episodes

5 days ago

Two Tokens Short is where retro arcade nostalgia meets today’s biggest conversations about AI, technology, and the industries they’re transforming. Hosted by Mitchell Newberger and Robert De La Rosa, this duo-fueled podcast mixes sharp insight with sharp humor — because sometimes you’re just a couple of tokens away from unlocking the bigger picture. From hospitality to healthcare, startups to culture, Mitchell and Robert press start on conversations that matter: the future of work, how humans adapt alongside machines, and the funny glitches along the way. So grab your tokens, hit continue,

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Short-Term Rentals at Scale: Luiz Batalha on Upstay’s $1B Hospitality Engine

Two Tokens Short

36 minutes 2 seconds

1 month ago

Short-Term Rentals at Scale: Luiz Batalha on Upstay’s $1B Hospitality Engine

In Episode 16 hosts Robert De La Rosa and Mitchell Newberger sit down with Luiz Batalha, co-founder of Upstay, to explore how a small experiment in short-term rentals evolved into 450+ properties, 8 markets, and $1.1B in managed assets.

Luiz shares the origin story—pivoting from Turo’s car-sharing model to vacation homes—and how Upstay scaled through AI-enhanced operations, remote-first culture, and a hospitality mindset built on data and guest experience. The conversation digs into:

How Upstay optimized P&Ls with AI and sentiment analysis
Direct-booking strategies and capturing 15% repeat guests via Wi-Fi marketing
Balancing automation and human service in hospitality
Expansion plans across Hawaii, Canada, and Dubai
What Orlando’s STR ecosystem teaches about scale and regulation

Whether you’re building in real estate, travel tech, or AI-driven operations, this episode reveals how to turn short-term rentals into a long-term business.

🎧 Insert Coin, Unlock Conversation.