Former Banker & Master Tailor: PROFF (AskOkey) – Reinvention, Identity, & The Power of Dressing Well

The Gstaad Guy sits down with Devon DeJardin, the visual artist working across painting, drawing and sculpture, whose Guardian figures have travelled from a friend’s apartment floor in North Hollywood to private collections and the cover of a number one album. Devon had never picked up a brush. He had a world religion degree, five hundred dollars to his name, a mattress he folded into a laundry closet each morning and a stack of unsold jackets when a stranger in Indiana paid him a hundred dollars for a ten minute phone call to tell him he was meant to paint. Six months later some of the most prominent collectors in Los Angeles were emailing his studio.

The Gstaad Guy sits down with Emily Oberg, founder and CEO of Sporty & Rich, who turned a Tumblr mood board into one of the most imitated brands in fashion. Before the store on Place des Lices in Saint Tropez, before Selfridges, Lacoste, Hôtel du Cap and Le Bristol, there were twenty sweatshirts she packed and posted herself. Ten years on, she is clear that the stretch in between is the part nobody films, and that the day during lockdown when a single drop did fifteen times its usual figure only reads as a beginning because the decade in front of it is invisible.

The Gstaad Guy sits down with Oliver Barker, chairman of Sotheby’s Europe and the man on the rostrum for many of the largest sales in the world, to explore what thirty two years at the same house teaches you about objects and the people who love them. Oliver joined as an unpaid intern in 1993 after Christie’s turned him down, and reflects on a career built on one unplanned afternoon, an eye trained by looking rather than reading, and the conviction that the greatest auctions are celebrations of culture rather than transactions.

The Gstaad Guy sits down with Gary Vaynerchuk, chairman of VaynerX and founder and CEO of VeeFriends, to explore what two decades of watching attention move has taught him about people. Gary built a career on seeing platforms before anyone else took them seriously, and reflects on a trajectory defined by conviction, self awareness, and a willingness to say the thing nobody in the room wants to hear, including about himself.

The Gstaad Guy sits down with Harry Stebbings, founder of 20VC and one of the most prolific investors and podcasters in Europe, to explore what separates the people who say they want it from the people who genuinely cannot do anything else. Harry started a podcast from his bedroom at seventeen with no university and no network, built it into an audience of millions and a fund with around a billion dollars under management, and reflects on a career defined by seeing early that media would become venture capital's real differentiator.