AI is reshaping short-term rentals fast.
In this episode, Mark sits down with Shahar, founder of Boom, to break down how operators can use AI + automation to scale without adding chaos.
Shahar shares how he went from broker/investor to building a tech-enabled property management company (managing roughly $150M of property)—then spinning the technology out into Boom as a standalone platform built for operators running at scale.
What you’ll learn:
- How Shahar validated his first Airbnb using staged “virtual design” photos before furnishing
- Why “market fit” matters more than building a great product—and how his first tech product struggled to monetize
- The real operational pain that forces software creation: owner statements, task management, approvals, vendor payments, reconciliation
- Why scaling STRs breaks from operations, not demand—and how “one system” reduces errors and labor
- The shift from SaaS tools everywhere to one operating system + AI agents (guest messaging, reporting, workflows)
- How AI can reduce guest-message volume so teams can focus on real problems and higher-touch hospitality
- Where the industry is heading: AI travel planning, agent-driven bookings, direct booking disruption, and even the long-term impact of robotics
- Why companies that don’t adopt AI won’t survive—and how top operators will scale from 100 doors to 500–1,000 with the same team
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Episode Sponsored By:
STR Search
STR Search is the industry leading property finder service. They've helped investors acquire over 325+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
