The STR AI Secrets That Save Time, Boost Reviews, and Give You a Competitive Edge

Sign up for this free course to discover how AI tools like ChatGPT and HostBuddy can automate guest messaging, personalize experiences, and elevate your operations.

STR Investing - Artificial Intelligence

Unlock the power of AI in your short-term rental business. This course shows you how to leverage AI for communication, guest personalization, automation, and team efficiency. Learn how to use tools like ChatGPT and HostBuddy to save time, improve reviews, and operate with confidence. Fresh insights added regularly.

About This Course

The next wave of STR profitability isn’t about buying more properties — it’s about using smarter tools.


This course reveals how AI platforms like ChatGPT and HostBuddy can handle guest messaging, personalize experiences, and even streamline turnovers, so you spend less time on screens and more time growing your portfolio.

This isn’t about chasing hype or replacing human hospitality. It’s about using AI as leverage—creating repeatable systems that free up your time, protect your reviews, and give your business an edge in competitive markets.

Browse Lesson Plan:

What is AI?

Coming soon.

ChatGPT

Coming soon.

Guest Communication & Automation

Coming soon.

AI for Guest Experience & Personalization

Coming soon.

HostBuddy AI

Walk through live demos and strategies with HostBuddy CEO Jay Ullrich to automate guest messaging, integrate with PMS tools, manage turnovers, and unlock hidden features that elevate operations.

Related Courses

Learn the software stack top STR hosts use to automate tasks, optimize pricing, and boost guest experience.

Frequently Asked Questions

What is STR Investing?

STR Investing is the education arm of our ecosystem, led by Mark Lumpkin and Taylor Jones. We built it to cut through the noise and give investors straightforward, actionable strategies for short-term rentals. Think of it as your free training ground — from acquisitions and design to operations, amenities, taxes, and beyond. It’s where today’s operators learn the same frameworks top STR pros actually use.

How much do your courses cost?

Nothing. They’re 100% free. We add new lessons regularly so you’re always up to date — but you’ll never have to pay to access them.

Do I need to own a property already to benefit?

No. These courses are designed for both beginners and seasoned operators. You can start learning before you buy — so when the right opportunity comes along, you already know what to do. And if you are ready to buy, our sister company STR Search (led by John Bianchi, “The Airbnb Data Guy”) can help you find and underwrite the right property.

How is this different from free advice on YouTube or TikTok?

Simple: depth and credibility. The STR space is flooded with surface-level tips and “gurus” chasing clicks. We’ve managed and invested in over 140+ properties ourselves. Our lessons are built on real numbers, real systems, and real results — not hype. Every course is structured to give you repeatable frameworks you can actually apply, not just recycled soundbites.

How do I get started after I finish the courses?

If you’re ready to put what you’ve learned into action, the next step is working with John Bianchi and STR Search. That’s where you’ll move from education into execution — finding profitable markets, identifying the right properties, and running the numbers with confidence. Learn more at strsearch.com.

Disclaimer: STR Investing provides educational content, resources, and strategies designed to help short-term rental (STR) investors make smarter decisions. While we share proven frameworks, expert insights, and real-world examples, we do not guarantee the financial performance of any property, portfolio, or investment. Real estate markets are inherently unpredictable, and individual results will vary based on factors such as location, regulations, management practices, financing, and other variables beyond our control. Any tax-related discussions, including topics like depreciation or the STR tax exception, are for educational purposes only. Achieving potential tax benefits requires meeting specific IRS qualifications, and we strongly encourage you to consult with a licensed tax professional or financial advisor before making investment or tax decisions. By accessing our courses, tools, and resources, you acknowledge that all investments carry risk. Past performance is not indicative of future results. STR Investing is not a tax, financial, or legal advisory firm, and the information provided should not be construed as professional advice.

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