Spring can be a weird time in the office. The excitement of the Holiday Season has worn off, but there are months to go before the next official bank holiday or long weekend.
So if a quick weekend getaway is on your list, now might be the time.
But as travelers know by now, the prices of Airbnbs have skyrocketed recently. And more often than not, those rental properties are hard to find at the last minute.
Alex Alioto and his co-founder Ben Jamshahi started Whimstay to fill an important gap in the vacation rental market. Jamshahi had been renting out several properties Airbnb and VRBO in California and VRBO. Even in these prime locations, the properties sat empty a large percentage of the time.
“Ben, with his sharp business acumen, was puzzled by the lack of effective solutions for what he saw as expiring inventory. The only option seemed to be discounting these units and hoping for the best – but hope isn’t much of a strategy. So, when Ben approached me with this dilemma, it was clear we needed a solution.”
What the two came up with was a “HotelTonight” model for vacation rentals.
“We were staring at a rapidly growing industry missing a critical piece: capitalizing on expiring supply. The timing was impeccable, and the market fit was undeniable. We were excited and ready to launch Whimstay without a moment’s delay,” Alioto told Hypepotamus.
To date, Alioto said that Whimstay’s target customers range from Baby Boomers to Gen Zs looking to get out of town for a quick vacation. But digital natives make up the bulk of the user case.
“This Next Generation of travelers, an identity that resonates strongly within our team, tends to value experiences over material possessions. They travel more frequently – often letting unbeatable deals dictate their destinations. This spontaneity and adventure-seeking mindset perfectly align with Whimstay’s ethos,” he added.
Whimstay is strategic about what geographies it expands into. But the Southeast seems to be a lucrative spot for the growing Bay Area-based team.
Of course, we had to ask the Whimstay team where they recommend a last-minute trip for those in the Southeast region. Noël Russell, Chief Experience Officer and founding member of startup, put together some fun ideas about where you might want to head next.Are you adding any of these spots to your vacation list?
