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Trip Hosley has extensive work experience in various industries. In 1999, they worked at Red Bull North America in the ON Premise role. From 2000 to 2004, they held the position of VP Business Dev at Three Deep. In 2001, they served as VP Sales at Nitetime.net. Trip then became a Board Member at the Hayes Valley Merchants Association in 2006. From 2005 to 2019, they owned Sauce Restaurant & Shine Lounge. In 2008, they worked as a Sales and Business Development Consultant at HOSSpitality Consulting. In 2009, Trip became the Owner of Sleep Over Sauce: Urban Guest House, managing a 9-room hotel. In 2017, they became a Business Owner/Investor at Long View Lodge. From 2021 to 2022, they worked as Sales Business Development at S.I. Container Builds, Inc., specializing in eco-friendly construction. Currently, Trip is the Director of Business Development at Conscious Container, where they play a key role in establishing infrastructure for glass bottle washing and reuse in the United States.

Trip Hosley attended Cornell University from 1986 to 1990, earning a Bachelor of Science degree in Hotel Administration.