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Steve Milo's work experience spans several industries and roles. In 1986, they founded and served as CEO of AnotherUniverse.com, a direct marketing catalog company that evolved into a multi-channel e-commerce and content site. Milo built the company from scratch and achieved significant sales and transaction numbers.

From 1999 to 2000, they were the President of New Media at Marvel Entertainment, overseeing the Electronic New Media Division.

In 2000, they joined Eyematic as the EVP Consumer Applications before moving on to become the Director of E-Commerce at The Bradford Group in 2002. At The Bradford Group, they reorganized an underachieving online unit and implemented successful organic and pay-for-performance search engine programs.

Milo then founded VRP Holdings LLC in 2005 and served as the Manager, Founder, and Owner. Under their leadership, VRP Holdings grew rapidly into one of the fastest-growing vacation rental management platforms in North America, with over 2000 properties under exclusive management. Steve also owned a software development and property management company for the vacation rental market, which experienced significant growth and employed over 130 employees.

Lastly, in 2018, Milo became the CEO of VTrips (formerly Vacation Rental Pros), a technology-enabled property management company. The rebranding signaled the company's commitment to expanding nationally and internationally.

Throughout their career, Milo has demonstrated a strong track record of entrepreneurial success, strategic leadership, and growth-oriented moves.

Steve Milo attended the University of Virginia from 1982 to 1986, where they obtained a Bachelor of Science degree in Commerce.