Gilkes has been based in New York since 2008. He served as an auctioneer at
Phillips de Pury & Company and worked at
LVMH. Gilkes presided as an auctioneer for auctions including Madonna's
Raising Malawi,
Elton John AIDS Foundation, and
amFAR. In 2011, he founded Paddle8, an online auction website selling fine art, photography, street art and collectibles. In 2013, the company did $US20 million in sales. By 2015, the company reported "$US140 million" in sales. Paddle8 was sold in 2015 to The Native. Gilkes stepped down from his role at Paddle8 in 2018. In 2020, Gilkes co-founded venture studio Squared Circles along with Lukas Derksen and Paddle8 co-founder Osman Khan. Gilkes "has been named" as one of ''
Fast Company's Most Creative Entrepreneurs in 2017, the 100 Most Powerful People in the Art World (Art + Auction) in 2014, 2015 and 2016, a Digital Maverick (DETAILS), one of the 40 Most Important People Under 40 (Apollo) and appeared on Vanity Fair and GQ's'' best-dressed lists. He serves on the board of the
New York Academy of Art. == Personal life ==