How Jay Ullrich Built 45 STRs by 28 and Launched HostBuddyAI to Automate It All Artwork

Skip the Lines Podcast, with Jonathan Mitchell

I interview experts in their field.

Skip the Lines Podcast, with Jonathan Mitchell

How Jay Ullrich Built 45 STRs by 28 and Launched HostBuddyAI to Automate It All

August 25, 2025 • Jonathan Mitchell • Season 1 • Episode 64

What if you could scale a 45-door short-term rental portfolio and build an AI company before hitting 30?

In this special episode of Skip the Lines Podcast, Jonathan Mitchell speaks with Jay Ullrich. Jay’s journey is anything but ordinary. At just 28, he’s already transitioned from a civil engineering degree at Cal Poly to running Select Stays, a San Diego-based short-term rental management company with 45 doors. Growing up in Maryland and moving across the country gave him the risk-taking mindset to pursue entrepreneurship. Starting with rental arbitrage and learning from thin margins, Jay quickly pivoted to management, building a business that emphasizes hospitality, professionalism, and treating guests like family.

Spotting inefficiencies in property management, Jay went on to co-found Host Buddy AI, a platform designed to automate guest messaging across Airbnb, Vrbo, and Booking. By pulling from past chats, availability, and property details, it responds instantly, saving hosts countless hours.

If you’re ready to stop drowning in guest messages, check out Host Buddy AI for a demo and follow Jay on Instagram and Facebook to keep up with his journey.

Chapters

00:00 Jay’s Early Life and Engineering Background

08:00 Launching Select Stays and Rental Arbitrage

12:31 Multifamily Growth and Brand Building

16:22 Host Buddy AI – Solving Guest Messaging

18:22 Lightning Round Insights

21:00 Lessons on Sales, Mentorship, and Growth

Quotes:

“Treating the guests like they were our parents changed everything.” – Jay Ullrich

“Host Buddy pulls your info and past conversations so you never have to look at your chats at dinner.” – Jay Ullrich

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