Going Places With Simone Sestito

The inclement weather certainly didn’t reflect the upbeat mood on a late November morning in Scottsdale, Arizona. It was drizzling rain in the desert as Places CEO Simone Sestito and his aviation team boarded the Bombardier Challenger 604, a private jet bound for Denver, Colorado, the penultimate stop on its journey to San Juan, Puerto Rico. Sestito had just sold the plane with an original listing price at $27 million to a private buyer in an off-market sale. Yet this was only one of many feathers in Sestito’s jet-setting cap. Steadily cruising at an altitude of 37,500 feet, the Challenger 604’s sleek design and spacious cabin was less a reflection of Sestito’s turbulent journey to climb these heights and more a symbol of his future-forward vision of the broader luxury experience market.


This was not the time to sit idle. Sestito’s boundless entrepreneurial energy was the driving force behind most of his successes – and colored his rose-tinted future. Now based in Miami, Florida, with his fiancé Alexandra Rodriguez, Sestito has built his career through sheer determination and grit. Always drawn towards the glitz and glamour of the entertainment industry, the Toronto, Canada born 34-year-old, and son of Italian immigrant parents, has already lived a life many would envy.

Sestito 1Photo Credit: Courtesy of Places.Co

Starting in the late 2000s, Sestito and his long-time business partner, Qarim Brown, began producing A-list events across the global entertainment circuit. Regular annual stops included the Cannes Film Festival, Formula 1 Monaco, Coachella, and Miami Music Week to name a few. It was through hosting events that Sestito developed relationships with some of the biggest names in the music and entertainment industry and when the seed was planted for his latest brainchild, Places.co.

Sestito 11Photo Credit: Courtesy of Places.Co

Understanding that true luxury requires access and a dynamic Rolodex, Sestito and Brown have set their sights on the technology industry. “We integrated our past knowledge, network, and relationships in the entertainment world, technology, and design with my quickly scaling luxury vacation rental company and formed Places” says the CEO beaming with pride on the eve of Art Basel Miami. “Using AI and machine learning systems, we have developed a recommendation engine that will redesign the future of luxury travel.

Sestito 6Photo Credit: Courtesy of Places.Co

But Places isn’t simply a capitalist-driven enterprise. Well aware of the heavy carbon footprint travel has on the environment, Places has made sustainability central to its corporate ethos. “We have actually started the process of becoming a certified B Corporation,” says Sestito, “a new kind of business that balances both purpose and profit. We will be legally required to consider the impact of our business decisions on our employees, customers, suppliers, community, and the environment writ large.” Indeed, it is this progressive vision, coupled with a bleeding-edge technology stack that has Sestito and Brown poised to scale even greater heights in the coming years. Places will be hosting several events this weekend at Art Basel to celebrate its impending launch.

 

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