The directive to “invest in passion” is foundational at every Peerage Partner company. That mindset is equally reflected in the iconic Dare to Dream collections of cars and sneakers that Miles assembled over a decade. Those best-in-class collections were sold at a global auction by RM Sotheby’s in May 2024, setting records for prices commanded by a number of rare items. (Press Release)


The internationally renowned Dare to Dream automotive collection includes some of the rarest versions of the world’s most classic cars. Miles has invested in passion by curating and displaying these vehicles in a manner that highlights their status as, in his words, “mobile works of art.”


Miles’ passion for sneakers originated with the acquisition of “The Ultimate Sneaker Collection” from Sotheby’s, which contained 100 of the most iconic sneakers of all time – including the original, ultra-rare 1972 Nike Waffle Racing Flat “Moon Shoe.” Since acquiring that collection in 2019, Miles has gone on to add hundreds of more pairs, including the Nike Mag from Back to the Future II, the Nike SB Dunk “NYC Pigeon”, and a game-worn and autographed Air Jordan 1 “Chicago” PE from Michael Jordan’s rookie season in the NBA.


For all of his focus on business, Miles’ family – including his wife, Kelly, and four grown daughters – is his greatest passion of all. He spends time with his extended family (which always includes at least one dog) at every possible opportunity.