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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📢 Connect with Jay Ullrich!
Website: https://www.hostbuddy.ai/
Instagram: https://www.instagram.com/jay_ullrich_/
LinkedIn: https://www.linkedin.com/in/jaytullrich
📢 Connect with me!
Instagram: https://www.instagram.com/jonathanmitchellre/
Facebook: https://www.facebook.com/profile.php?id=100088499808533
Instagram: https://www.instagram.com/jonathanmitchellre/
Facebook: https://www.facebook.com/profile.php?id=100088499808533
LinkedIn: https://www.linkedin.com/in/jonathan-mitchell-a1493410b
TikTok: https://www.tiktok.com/@jonathanmitchellre
Twitter (X): https://www.tiktok.com/@jonathanmitchellre
ADU PALS: https://adupals.com
Business Inquiries: jonathan@adupals.com
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