The Boostly Podcast: "Fries With That? How to Master Upsells & Boost Your Short-Term Rental Profits"

Release Date: July 14, 2025

In this insightful episode of The Boostly Podcast, host Mark Simpson engages with panelists Laura Muse, Mike O'Connell, and Siddhi Matal to delve into the art and science of upselling within the short-term rental (STR) industry. The discussion centers around strategies to enhance guest experiences while simultaneously increasing rental profits through effective upsell techniques.

1. Introduction to the Panel

Mark Simpson opens the session by welcoming listeners to a special webinar format of the podcast, introducing the esteemed panelists:

• Laura Muse: A UK-based host of the award-winning holiday let, Muse Escapes, located in the picturesque Peak District. With three years in the industry, Laura emphasizes creating unique guest experiences.

• Mike O'Connell: Founder of Happy Guest and an experienced STR operator, Mike brings insights from both the operational and technological facets of holiday rentals.

• Siddhi Matal: Co-founder of Why Hangry, the UK's largest private chef platform, Siddhi discusses integrating culinary experiences into STR offerings.

2. Identifying Guest Needs for Upsells

The conversation begins with Laura Muse sharing her approach to understanding what guests desire beyond their initial booking:

Laura Muse [04:01]: "For us, the nuts and bolts of it is we contact all of our guests. So 98% of our guests, we speak to every single one of them on the phone. We have a special guest services manager that does that... But there's nothing better than the personal touch for an actual guest who is checking in."

Laura emphasizes the importance of personal communication, using phone calls to glean insights into guests' preferences and tailor upsell offerings accordingly. She highlights that while automation tools are valuable, the human element remains irreplaceable in discerning and meeting specific guest needs.

Mike O'Connell concurs, adding the necessity of knowing your guest persona:

Mike O'Connell [06:54]: "If you don't know who that guest is, you're gonna have a really hard time selling them something that they want... Seasonality is a big thing too."

Mike underscores the importance of timing and relevance in upselling, ensuring that the services offered align with the guests' purposes and the time of year.

3. Implementing Upsell Strategies with Technology

The panel transitions to discussing the integration of technology to streamline upselling without overwhelming hosts with additional tasks.

Siddhi Matal introduces Why Hangry's role in simplifying the upsell process:

Siddhi Matal [09:07]: "We can give you a widget which is like no code. You just add it to your website. One click. And we're also launching on Guesty and Touchday soon."

Siddhi highlights the ease of integrating upsell options through simple technological solutions, allowing hosts to offer culinary experiences seamlessly without significant technical overhead.

Mike O'Connell adds a complementary perspective on blending technology with the human touch:

Mike O'Connell [12:12]: "Happy Guest is there for you to free up time to then utilize that extra time to kind of run a full-fledged concierge service... nothing's going to convert like a human touch."

Mike emphasizes that while technology facilitates the upsell process, the personal interaction remains crucial for conversion.

4. Leveraging Local Partnerships

Laura Muse elaborates on the value of forging partnerships with local businesses to enhance the guest experience and support the local economy:

Laura Muse [14:06]: "We've partnered up very well with the Tourism Board, we've partnered up very well with local businesses within our area... When people book on booking.com etc, the money doesn't go into that local area. Whereas when it's a direct booking, I'm really keen that when that guest comes to State News Escapes, they spend their money within the Peak District."

By collaborating with local vendors, Laura ensures that guests have access to authentic experiences while keeping the economic benefits within the community. This strategy not only enriches the guest's stay but also strengthens the host's relationship with local enterprises.

5. Marketing Upsells to Guests

The panel explores effective marketing tactics to promote upsells to guests. Siddhi Matal highlights the importance of early and varied promotion:

Siddhi Matal [17:25]: "We actually offer 10% commission back on every single booking... it's one of the things that Laura mentioned, but it's not something that comes after booking."

Siddhi underscores the advantage of showcasing upsell options early in the booking process, boosting host conversion rates by offering added value from the outset.

Mike O'Connell discusses leveraging user-generated content and creative marketing:

Mike O'Connell [20:06]: "We have loads of properties which we work with Maddie from Mount, where all of the tours, local activities, things that you can book, have these awesome reels that are kind of in your face."

By utilizing engaging visual content and strategically presenting upsell options during the booking phase, hosts can effectively entice guests to consider additional services.

6. Actionable Steps to Begin Upselling

As the discussion nears its conclusion, the panel provides practical steps for hosts looking to implement or enhance their upsell strategies:

• Laura Muse emphasizes experiential authenticity:

  Laura Muse [23:02]: "I went kayaking, I went abseiling... It tells my guest a story. So if I was to start again... I won't do anything different."

  Laura advises hosts to base their upsell offerings on personal experiences to ensure genuine and compelling proposals.

• Siddhi Matal suggests testing demand before fully committing:

  Siddhi Matal [26:05]: "You can even just start off by telling them you have something and seeing if someone emails you back."

  Experimenting with simple offers can help gauge guest interest and tailor future upsell options accordingly.

• Mike O'Connell recommends proactive communication and leveraging local resources:

  Mike O'Connell [25:00]: "Focus on relationships... Every local museum, guess what? They don't want to deal with the big, huge OTAs... They're taking a massive cut."

  Building strong local connections can open doors to mutually beneficial partnerships and enhance the host's service offerings.

7. Closing Insights

Mark Simpson wraps up the webinar by reiterating the importance of taking immediate action:

Mark Simpson [27:33]: "Just use this next week, seven days after here to pick up the phone, speak to your past guests, see what experiences they did do, or even call the new bookings that are coming up and ask what they are looking forward to do."

Mark encourages hosts to leverage direct communication and existing technological tools to kickstart their upsell initiatives, emphasizing that the barriers to entry are low and the potential rewards substantial.

Conclusion

This episode of The Boostly Podcast offers a comprehensive guide to mastering upsells in the short-term rental market. By combining personal engagement, technological integration, and strategic local partnerships, hosts can significantly enhance guest experiences while boosting their rental profits. The panelists provide actionable advice and highlight the importance of authenticity and proactive communication in successfully implementing upsell strategies.

For more insights and strategies, visit Boostly's YouTube Channel or connect with the panelists through their respective platforms:

• Laura Muse: musescapes.com | Facebook: Laura Muse Official
• Mike O'Connell: Happy Guest | Instagram & LinkedIn: Happy Guest Official
• Siddhi Matal: Connect via LinkedIn: Siddhi Matal

Embark on your upsell journey today and transform your STR business with these expert strategies!