In this episode, Mark Lumpkin sits down with Jay Ullrich, STR operator, tech founder, and CEO of HostBuddy.ai - to unpack his journey from cold-calling landlords and scrubbing his own units to managing 45+ short-term rentals and launching one of the most advanced AI guest communication tools in the industry.

Jay shares:

• How he built a thriving STR property management company without outbound sales
• What he learned scaling from 1 arbitrage unit to 45+ managed homes in San Diego
• Why HostBuddy.ai was born out of late-night guest message fatigue, and how it works
• How today’s AI tools can help you reduce stress, automate communication, and increase profits
• Why HostBuddy stands out from every other AI chatbot in the space
• The challenges of scaling and how to maintain trust as you grow
• How to test HostBuddy live on their site (no signup required!)

Whether you’re just starting in cohosting or you’re managing dozens of units, this episode is packed with firsthand experience and future-focused insights that can save you time, money, and headaches.

Try HostBuddy's AI for yourself → https://hostbuddy.ai

Connect with Jay: jay@hostbuddy.ai | @hostbuddy_ai on Instagram

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Enjoyed the show? Subscribe, share, and leave a review for the STR Investing, The Podcast so more hosts can scale smarter.

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Episode Sponsored By:
STR Search

STR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com

What if you could give your guests a memorable, screen-free experience and stand out in a crowded short-term rental market—without adding a $10K hot tub or building a pickleball court?

In this episode, Mark sits down with Rachel from QR Clue, a former property manager turned entrepreneur who’s on a mission to turn everyday rentals into unforgettable guest experiences. QR Clue is a ready-to-go, interactive mystery game—part escape room, part storytelling adventure—that guests play using subtle, QR-coded items placed throughout your property.

You’ll learn:

• The “aha moment” that sparked QR Clue’s creation
• Why this amenity can be installed in any STR (with just a kitchen + bedroom)
• How hosts are using QR Clue to drive more bookings, 5-star reviews, and guest data collection
• Why it’s designed only for vacation rentals (sorry, hotels 👋)
• What setup, reset, and guest playtime actually looks like
• How families, friends, and even company retreats are using it to connect and create memories

If you’re looking for an easy, low-lift way to upgrade your guest experience (and boost your bottom line), this one’s for you.

Learn more at QRClue.com or email them at hi@qrclue.com

Like what you hear? Subscribe, share, and join us again next Friday!

In this special live episode, Mark and Taylor sit down in person to riff on one of their shared obsessions: sales. But this isn’t your typical sales 101 chat. It’s raw, real, and full of battle-tested strategies that have helped them close deals from cars to real estate to STR investments.

Here’s what they dive into:

• Why “assuming the close” only works if you believe in your product
• The “cancer pill” mindset that will transform how you sell
• How to uncover and use the power dynamic in two-person sales conversations
• The underrated brilliance of Men's Wearhouse sales strategy
• Why you should never book client calls at 12:00 or 12:30
• “Choice of two positives,” “calendar closes,” and other tricks you’ll want to steal
• When and how much pressure to apply—and how to make it match your personality
• The one universal reason someone doesn’t buy from you
• Why storytelling beats pitching every time

Whether you’re running sales for your STR business, pitching investors, or just trying to close more life deals—this episode will sharpen your edge.

Biggest takeaway? Sales is just a transfer of emotion. So be real, believe in your offer, and go close.

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Episode Sponsored By:
STR Search

STR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com