Skift Live

Philip Kennard



S. Philip Kennard is a serial tech entrepreneur, hospitality executive and software engineer. He founded Futurestay to help millions of rentalpreneurs around the world reach their goals and make more money with short-term rentals.

Philip secured his first commercial software development contract at age 15, prior to completing his degree at the University of Virginia with a Psychology/Biology concentration. He leveraged that contract to launch a proptech consultancy that developed the first real-time site plan management software, serving the largest brands in global real estate including Brookfield Properties and Renaissance Properties.

After selling his first tech venture in 2010 and hastily purchasing “more apartment than he could afford”, he turned to short-term renting his New York City loft out of necessity, to cover his expenses.

Like tens of millions of others have since, Philip unknowingly became a “Rentalpreneur”; an independent short-term rental host seeking financial flexibility and a better lifestyle.

When he searched for a software to optimize his one-man rental venture, Philip realized that all existing products were complex, expensive and clunky – built for professional vacation rental management companies and not the 95% of hosts like him who had just one or two STR properties.

Growing frustrated with the disadvantages that everyday rentalpreneurs face, Philip was inspired to build a tech solution and partnered up with his friend Jonathan Fabio. They founded Futurestay to make it possible for everyday people to succeed in STR.

Under Philip’s leadership Futurestay has helped tens of thousands of rentalpreneuers around the world run successful short-term rentals, raised over $20M of venture capital, formed exclusive and strategic partnerships with the largest enterprise in travel including Google and, and driven hundreds of millions in bookings to its users.

Philip’s contagious passion, clarity of vision and bold mission to democratize STR for the 99% has garnered numerous awards and accolades, including Vacation Rental Management Assoc’s ‘Innovator of the Year’, American Resort Developers Assoc. ‘Innovation Fast Track’, Phocuswright’s ‘Hot Travel Startups’, Skift’s ‘Top Startups’, and landed Philip a position on the VR Tech ‘Most Influential Short-Term Rental Professionals’ list.

Philip is relentlessly driven by his mission to empower anyone, anywhere to live their best lives through short-term rentals.

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