All Forum Posts by: Theresa Holl

Glenn -  Sorry for your loss first of all. 

So many paths you could take here. I am happy to have a strategy chat with you.  Definitely slow down and get a handle on the hidden costs and benefits in a few different options.  I'll shoot over a few "land hacking" resources to help you get organized. 

I'll try to connect you with someone. 

 I love the anticipation.  Great point.  :)

Hey Andrew - some call this land hacking, depending on what exactly you're trying to do. I can give you some resources for your review. My business partner also has a lot of knowledge around marketing strategies for this type of STR.

Hey Jacob, I'd love to learn more about how you've been running it. Have you had a marketing audit lately?  Events and gatherings should be good money. 

My guy Ian Karanja is really good. Check out Onyx Insurance Brokers. I can connect you. 

Ok - this is interesting.  I heard from Guesty last month that they'd be rolling our Guesty Lite, sitting on the same platform as Guesty for Pros, and now it's up on their site.  The biggest dig against Guesty in the past was that Guesty for Hosts and Guesty for Pros were on different platforms and upgrading was anything but seamless.  So as this rolls out, I'm super curious about whether this takes a bite out of their competition, especially Hospitable.  They both have decent AI and general features.

The PMS wars continue.  Watch this space.

Another thing you can do is research to determine high-performing key words on trends.google.com, as well as the high-performing listings in your area.  Also switch out the last and second to last picture on your listing often.  Here are a couple other tips:

• - Describe each room with LONG descriptions with tons of details like mattress type and bedding quality. List all the kitchen appliances and utensils. You’ll need a photo of all this stuff laid out to see.
• - In the captions on the photos, beyond describing the quality of the furnishings, describe in detail the experience your guest will have there. Be EMOTIONAL here and connect with your prospective guest’s inner desire for escape, thrill, relaxation, fun, connecting with family, etc…

Make sure each picture has captions written out.  You can get help from ChatGPT or Jasper AI if you don't love writing.

Totally agree. People should optimize the site itself before investing a nickel in tech.  AI communication is getting super personalized tho. Hospitable can program messages for about any avatar and it's still automated.  To me, the line between personalized and AI is blurring...at least based on what I'm seeing from my partners.

Since people ask about this all the time, I thought I'd post my version and would love to hear feedback from new and established hosts.

1. Underestimating the Importance of AI and Automation

Automation technology is a game-changer in the short-term rental industry. Hosts who fail to leverage AI for tasks such as dynamic pricing, guest communication, and property management are missing out on maximizing their profits and efficiency. Tools that automate these aspects can help ensure your property remains competitive and that guests receive timely and personalized responses.

2. Neglecting the Guest Experience

A memorable guest experience is central to success in the short-term rental market. This means more than just providing a clean space; it involves thoughtful touches like welcome baskets, local guides, and amenities that cater to your target audience (families, business travelers, etc.). Overlooking the finer details can result in negative reviews and lower booking rates.

3. Overlooking Proper Market Analysis

Many hosts set their pricing based on intuition rather than data. Utilizing platforms and tools that offer market insights (AirDNA, Rankbreeze, Wheelhouse, PriceLabs, Smart Pricing) and competitive analysis can help you price your property optimally throughout the year. Understanding peak seasons, local events, and average occupancy rates in your area can prevent underselling your space or pricing yourself out of the market.

4. Failing to Optimize Listings

A compelling and detailed listing is pivotal in attracting guests. Hosts often make the mistake of using low-quality photos or vague descriptions. Investing in professional photography and writing a clear, detailed description that highlights the unique features of your property can significantly increase your visibility and booking rate.

5. Ignoring Regulatory Changes

The regulatory landscape for short-term rentals is constantly evolving. Failing to stay informed about local laws and regulations can lead to hefty fines or the shutdown of your listing. It’s crucial to ensure you’re compliant with your city’s requirements, including permits, taxes, and safety regulations.

Ok - that was just a stab at it.  What do you all think?  Any recent trainwrecks or lessons the rest of the forum can learn from?