Podcast Summary: Maximizing Last-Minute Bookings with Whimstay | Featuring Alex Alioto

Podcast Information:

• Title: The Boostly Podcast
• Host: Mark Simpson
• Episode: Maximizing Last-Minute Bookings with Whimstay | Featuring Alex Alioto
• Release Date: January 27, 2025

Introduction

In this episode of The Boostly Podcast, host Mark Simpson welcomes Alex Alioto, the CEO, Co-founder, and Head of Growth at Whimstay. The episode delves into strategies for maximizing last-minute bookings in the short-term rental market, offering valuable insights for both hosts and travelers.

Understanding Whimstay

Alex Alioto introduces Whimstay as a burgeoning OTA (Online Travel Agency) based in Sausalito, California, serving the U.S., Canada, and Mexico, with plans to expand into the UK and Europe soon.

“We are an OTA that specializes in helping hosts and property managers fill their unsold gap nights, weekdays, last-minute bookings, and expiring inventory.” (02:30)

Whimstay differentiates itself by focusing on the often-overlooked short-term rental opportunities that larger OTAs like Airbnb and Booking.com may miss, particularly during off-peak seasons.

OTA vs. Direct Bookings

Mark and Alex engage in a thoughtful discussion on the balance between using OTAs and fostering direct bookings. While Boostly emphasizes direct bookings to build business stability and reduce dependence on OTAs, Alex underscores that Whimstay complements this approach rather than competes with existing OTAs.

“Direct bookings actually help the industry as a whole, including OTAs... the better your hospitality, the more likely people are going to come back.” (04:46)

Alex points out that improving direct booking strategies enhances overall hospitality standards, benefiting both hosts and travelers. He advocates for using OTAs like Whimstay as part of a diversified distribution strategy to maximize occupancy and revenue.

How Whimstay Works for Guests

From a guest's perspective, Whimstay functions similarly to other OTAs—through an app or website where travelers can search for and book properties. However, Whimstay targets last-minute travelers who seek spontaneous bookings, often offering discounted rates to fill unsold inventory quickly.

“From the traveler’s perspective, they’re looking last minute, so they’re a little bit more of a spontaneous-minded traveler.” (07:07)

Guests can find accommodations that might not be available on other platforms, catering specifically to their immediate booking needs.

How Whimstay Works for Hosts

For hosts, Whimstay serves as an additional channel to boost bookings without the hefty commissions associated with traditional OTAs. Currently, Whimstay integrates with Property Management Systems (PMS) to automatically list available dates. An upcoming RBO (Run-By-Owner) portal will allow individual hosts to sync their calendars via iCal, simplifying the process further.

“Use us as an extra sort of arrow in your quiver... specialize in filling in your unsold gap nights, weekdays, etc.” (07:44)

Alex advises hosts to view Whimstay as part of a comprehensive distribution strategy, complementing other marketing efforts like social media and email campaigns to maximize occupancy.

Industry Insights: Supply and Demand Trends

Mark shares recent data indicating a decline in short-term rental supply, particularly post-COVID-19, with a specific mention of a 30% drop in local listings. Alex concurs, noting that the industry is still in its infancy and there is significant room for growth and improvement.

“We are in the first inning of this thing... there’s a lot of market share for us to take from hotels.” (18:54)

Both speakers agree that as supply fluctuates, platforms like Whimstay play a crucial role in balancing the market by efficiently matching available properties with traveler demand.

Future Plans for Whimstay

Looking ahead, Whimstay aims to expand its presence in the UK and Europe, building robust customer service capabilities to support hosts and travelers globally. With an ambitious goal of helping hosts increase their occupancy by 20% within a year, Whimstay is positioning itself as a vital tool in the short-term rental ecosystem.

“By 2025, we have... a really fantastic option for hosts to raise their occupancy 20% over the course of a year.” (20:29)

Alex emphasizes the importance of exceptional customer service as a cornerstone for Whimstay’s growth and sustainability.

Closing Thoughts and Inspirational Insights

In the concluding segments, Alex shares heartfelt advice for budding entrepreneurs and individual hosts:

“If your timing is right, your market fit is good, and you believe in this thing, then... keep going. It becomes... just a war of attrition.” (26:25)

Mark echoes the sentiment, highlighting the importance of perseverance and resilience in the competitive short-term rental market.

Key Takeaways

• Whimstay’s Niche: Focuses on last-minute bookings and unsold inventory, offering a unique opportunity for hosts to maximize revenue during off-peak times.
• Complementary Strategy: Whimstay complements existing OTAs and direct booking efforts, enhancing overall occupancy and revenue potential.
• Future Expansion: Plans to expand into the UK and Europe, with a strong emphasis on customer service and market penetration.
• Industry Growth: The short-term rental market is still evolving, presenting ample opportunities for innovative platforms like Whimstay to capture significant market share.
• Entrepreneurial Advice: Success in the short-term rental business, as emphasized by Alex, requires perseverance, adaptability, and unwavering belief in one’s vision.

Notable Quotes with Timestamps

• Alex Alioto (02:30):
  “We are an OTA that specializes in helping hosts and property managers fill their unsold gap nights, weekdays, last-minute bookings, and expiring inventory.”

• Alex Alioto (04:46):
  “Direct bookings actually help the industry as a whole, including OTAs... the better your hospitality, the more likely people are going to come back.”

• Alex Alioto (07:07):
  “From the traveler’s perspective, they’re looking last minute, so they’re a little bit more of a spontaneous-minded traveler.”

• Alex Alioto (07:44):
  “Use us as an extra sort of arrow in your quiver... specialize in filling in your unsold gap nights, weekdays, etc.”

• Alex Alioto (18:54):
  “We are in the first inning of this thing... there’s a lot of market share for us to take from hotels.”

• Alex Alioto (20:29):
  “By 2025, we have... a really fantastic option for hosts to raise their occupancy 20% over the course of a year.”

• Alex Alioto (26:25):
  “If your timing is right, your market fit is good, and you believe in this thing, then... keep going. It becomes... just a war of attrition.”

Conclusion

This episode of The Boostly Podcast offers a comprehensive look into how platforms like Whimstay are reshaping the short-term rental landscape by addressing last-minute booking challenges. Alex Alioto’s insights provide hosts with actionable strategies to enhance their occupancy rates and navigate the competitive market effectively. Whether you’re a seasoned host or just starting, the conversation underscores the importance of adaptability, strategic distribution, and unwavering commitment to excellence in hospitality.

For hosts interested in leveraging Whimstay, Alex encourages reaching out via email or visiting the Whimstay website to get started and take advantage of the platform’s growing capabilities.

Timestamp Reference Guide:

• 02:30 - Introduction of Whimstay
• 04:46 - Benefits of Direct Bookings
• 07:07 - Guest Experience on Whimstay
• 07:44 - Whimstay’s Role for Hosts
• 18:54 - Industry Growth and Whimstay’s Position
• 20:29 - Future Plans for Whimstay
• 26:25 - Inspirational Advice from Alex

Note: Timestamps correspond to the transcript provided and are indicative of when specific topics and quotes occur within the podcast episode.