Billy O'Sullivan

Billy O'Sullivan is a dynamic hospitality leader and real estate entrepreneur whose career spans luxury vacation rentals, global property management, real estate development, and entertainment. Known for his community-driven approach to business, O'Sullivan has successfully scaled multiple ventures while remaining grounded in the Hawaiian ethos of the "Aloha Spirit."

Current ventures & investments

• Founder, Ohana Inns. In November 2020, O'Sullivan co-founded Ohana Inns with Cliff Johnson to build a family-style hospitality group of inns, cabins, and cottages. They purchased their first property in Maine during the pandemic and operate exclusively in commercial spaces. The company emphasizes employee empowerment by offering ownership down to the housekeeping level, and is highly eco-conscious, planting a tree for every guest and working toward a net-zero climate impact. Seven properties acquired so far, with expansion underway into Vermont, New Hampshire, New York, and Massachusetts.
• Global Portfolio Manager. O'Sullivan manages diverse private portfolios spanning Detroit, Sedona, Colorado, Idaho, Maine, Utah, Chile, and Costa Rica.
• Vacation Rental Fund. Co-founded and consults for the Vacation Rental Fund alongside Michael Zuckerman, helping VR managers with accounting, administration, and fundraising.

Executive leadership in hospitality

• CEO of ALTIDO (2019–2022). Merged four major European vacation-rental firms into the supergroup ALTIDO. During the COVID-19 pandemic, he designed "ALTIDO Lite" to ensure the company's survival, famously furloughing himself and stepping aside so a co-founder could lead. He ultimately returned to help guide the company to a successful exit in January 2022.
• Partner at Property Management Inc. / PMI (2017–2019). Recruited to build PMI's Vacation Rental pillar, O'Sullivan created a resource drive with over 800 pieces of content used for training and marketing across the franchise network. He led the acquisition of bookbyowner.com, onboarding 22 offices and over 1,800 properties, and helped develop the PPM that successfully raised $8 million in capital.
• Partner / CMO at Park City Rental Properties (2015–2017). Brought his expertise to the mountains of Utah, doubling the company's unit count from 147 to 312 in just 20 months. His sales team generated $16 million in vacation-rental bookings in their first year using a grassroots, handshake approach.

Real estate & brokerage

• Kauai Vacation Group & Kauai Real Estate Group. As founder, his team sold hundreds of millions of dollars in real estate and managed top-tier vacation rentals over a ten-year period. He recently sold a majority stake to pursue other ventures.
• Blueprint Capital. Working as an investor and fundraiser, O'Sullivan helped raise $80 million, scaling the network from 12 to 60 builders who developed nearly 3,000 units in the Seattle area. He remains an active investor.
• Keller Williams Realty. A deep history with Keller Williams in the Pacific Northwest, building one of the top-five producing real estate teams in the Seattle area. He was a team leader and owner in Bellevue and served as a highly coveted BOLD Coach, training the top 1% of producing agents in the region.

Early career: Hollywood production

O'Sullivan's professional journey began in the entertainment industry. He bypassed high school to earn his AA degree by age 16 before attending the University of Southern California's film school. At just 17, he founded Marker, a full-service Hollywood production house, where he spent years directing and producing award-winning commercials for global brands including Budweiser, Pepsi, Mattel, and Taco Bell. He also produced music videos for artists like The Killers and The Crystal Method. He's currently developing a vacation-rental TV series, The Host With The Most, alongside Oscar-winning producer Michael Sugar.

Philanthropy & the Aloha Spirit

• SpiritofCAN.com. Co-created a campaign and clothing line to fund and raise awareness for women's breast cancer screenings on Kaua'i.
• Aloha Angels. An active angel investor who sponsors educational children's books for classrooms across Hawaii, teaching tourists and youth about the Aloha Spirit.
• Random Acts of Walter. Founded a unique philanthropic initiative where his company hires a handyman full-time for 60 days a year, simply to perform free "acts of maintenance-kindness" on local Hawaiian homes.

Personal life & extreme athletics

O'Sullivan is an extreme-sports enthusiast. In 2016 he paddled the 101-mile Ka'ie'ie Waho channel from O'ahu to Kaua'i, the deepest and widest open-water channel in the world, via outrigger canoe. Alongside his wife Tiger, he's known to explore cities by running them block by block; in 2019 the couple completed a 50k freestyle run spanning the entirety of Manhattan in the sleet and snow.