Our journey to Meet the Draper’s season finale in San Mateo was a whirlwind. We found out the day before that we’d been selected as one of the 6 finalists, and had to drop everything and run to California. That meant leaving our two young kids in New York City with the nanny, booking last minute–and pricey– tickets, and finding an Airbnb on the flight (all our Vacayos had already sold out). As if our trip was destined for chaos, the moment we arrived in California past midnight, I received a cancellation notice from our Airbnb guest. This frustrating experience, I later realized while settling into our sterile room at The Marriott, was the exact reason owners need professional managers like Vacayo!


We arrived early the next morning at Draper University for a preliminary meeting with the judges. After, we spend an hour piecing together a new pitch, focused more on us as founders and the company backstory. Every game-changing business has a unique story, often one that involves struggle, and Vacayo is no exception!

On stage, we had an opportunity to recount the hustle and scrappiness of our earliest days. In the span of a few months, Truth and I went from roommates to startup partners—and later, spouses—in what began with simply Airbnbing the spare bedroom in our East Village walkup. What was first a side hustle turned into a full-fledged business with validation from landlords and guests. We had very different backgrounds, him being a Nigerian Immigrant and myself, a 4th generation American Jew, but our common thread was a passion for the sharing economy and belief in our disruptive business model. To grow from 0 to 1 million in revenue without VC funding, we bootstrapped and furnished homes for free off Craigslist. Everything was about how we could maximize resources. We could tell the judges, in particular Tim and Bill Draper, were moved by our determination.


By the end of the finale, we walked away with funding and the opportunity to discuss a larger investment with Tim Draper! Adding Tim Draper to our Cap Table is a peak 2018 moment for Vacayo. Another angel, Stephen Silver, made an impromptu investment in Vacayo at the finale. All in all, the trip was a success and reminded me that as an entrepreneur you have to seek out opportunities and embrace the mayhem… there’s no set path!