Whimstay offers guests the best deals on last-minute vacation rentals across North America
How did you become CEO of Whimstay?
I previously served as President at a payments company called Yapstone, where we built and operated Vrbo’s end-to-end FinTech experience, serving over 100 million travelers globally and over 1 million property owners in North America and Europe. We also integrated with major vacation rental software companies, powering payments for thousands of vacation rental property managers worldwide. It was through that experience and working with a private equity firm in 2021 focused on travel that I was introduced to Ben Jamshahi, the founder at Whimstay.
We hit it off immediately. I brought with me 10 years of relationships and operating experience in the sector, and Ben had built this amazing foundational product and go-to-market strategy. I was so excited about Whimstay that I spent the first half of 2022 working with Ben as an advisor thinking through where we could take the business together. He hired me as COO in Aug 2022, and I was then appointed CEO in Jan ‘23.
What is the vision behind Whimstay?
Prior to Whimstay, there was no place, no site, that enabled guests to find the best deals on last-minute vacation rentals. There were tons of options for hotels but nothing for vacation homes, villas, condos, and other alternative accommodations. At the same time, vacation rental property managers were becoming marginalized on the major OTAs at the expense of travelers and individual property owners, where they had limited control of the guest experience or ability to demand better economics.
We’ve built a proprietary solution that solves these problems for these two distinct yet inextricably linked groups, travelers and property managers. We identified these large, completely unserved segments of the $200 billion short-term rental industry, and then decided to go fill those needs because we had such strong market pull from both sides.
From the idea to the start, what have been the biggest challenges so far and how did you finance yourself?
The industry is laden with juggernauts like Expedia, Booking.com, Airbnb, and Vrbo, who have tremendous resources and capabilities. The three biggest challenges we’ve begun to overcome have been, (1) can we build something that is truly different and better than what exists currently in the market? (2) can we hire the right people to build, operate, and grow the business? and (3) can we do (1) and (2) in an extremely capital-efficient manner? We’ve answered yes to all three.
Guests can see and find value (deals) on our site they can’t get anywhere else. We’ve become that differentiated channel partner to professional property managers. The team we have in place is reflective of a much larger, more advanced company, who share critical core values. We’ve grown the business from 40k users in 2021 to 1.5m users today, 50 property managers to 800 property managers, and 150,000 properties over that same time period, and bookings are up 400% vs. last year. In a sector where fundraisings and capital investment are measured in hundreds of $millions and $billions, we’ve gotten to this point on $10m raised from individual investors.
Who is the target group of Whimstay?
We’ve learned everyone likes a great deal, let alone the best deals, whether you’re looking for a $2,000 per night, 8-bedroom villa on the beach in Cabo or a $100 per night, one-bedroom condo several blocks from the ocean in Myrtle Beach. We serve Gen Z to Boomers. Of those who booked on Whimstay in 2023, 14% are ages 18-24, 25% are 25-34 yrs old, 22% are 35-44 yrs old, 18% are 45-54 yrs old, 21% are over 55 yrs old, and 16% are international travelers.
How does Whimstay work? What are the advantages? What makes you different from other providers?
We’re able to offer the best deals to guests because we do two things, (1) we receive exclusive discounts from property managers on a large percentage of our properties for bookings made less than 30 days prior to arrival, and more importantly (2) we’re the first site to dynamically price total cost of the trip. Any site can offer discounts on nightly rates. We’ve built the capability to price total trip cost to account for a nightly rate, mark-ups and discounts to nightly rate, all the fees that each OTA charges the guest, and the myriad of fees the property managers or Hosts charge the guest.
Then we do a real-time check at booking to validate that our total cost is less than other OTAs. In addition, we only work with professional property managers, so our accommodations are more curated, and our guest experience is more consistent, reliable, and enjoyable.
Whimstay, where does the road go? Where do you see yourself in five years?
We’re done a great job in marketing to a point now where millions of travelers associate Whimstay with great deals on last-minute vacation rentals. In five years, we expect Whimstay to be a household name for guests worldwide. We’ll continue to introduce product offerings that will make the travel experience easier, more flexible, and lower cost, and we’ll include more services and experiences in our offering.
We intend to broaden our inventory footprint throughout North America and expand into Europe, Australia, Asia, and Latin America. We’ll continue to improve our value prop relating to the best deals on vacation rentals to include more differentiated pricing and have the best deals apply to longer booking windows beyond 30 days. In just two years, we’ve gone from 100% of our bookings being made within 30 days prior to arrival to 75% of bookings this year. We expect this trend to continue.
At the end: Which 3 tips would you give to future founders or business leaders?
Determine what makes you different and better vs. the competition. Then maniacally continue to build that delightful experience for customers and stay true to who you are as a company. Maintain that edge and focus.
Hustle, be scrappy, work harder than your competition, collaborate, ask for help, and it’s absolutely critical to have a short-term memory. Don’t get too high on how great you are, and at the same time, you have to be able to seamlessly move on and power through setbacks, failures, and other disappointments. Have conviction.
Build a great team. People you can trust to execute on a shared vision. Hire those who share common core values and common work values. Yes, your product, customer experience, value prop, go-to-market strategy, etc. are critical factors…but great people make these things happen…great people foster, nurture, and improve these things…great people make great companies.
Thank you David Weiss for the Interview
Statements of the author and the interviewee do not necessarily represent the editors and the publisher opinion again.
