The process of finding yourself at Samantha Boardman's (the founder of Positive Prescription, a mental health and wellbeing-focused lifestyle and media brand) Upper East Side townhouse goes a little something like this. Once you're buzzed in, you step inside and begin removing your shoes, only to look up and find a towering stack of Warhol Del Monte and Campbell's Soup boxes to your right. Take a peek to your left and you're confronted by a full-scale Basquiat. "Is this normal?" you think to yourself, "The last time I was surrounded by this much contemporary art I was expected to take notes and there was a quiz afterwards." A few steps forward into the dining room, through a hall bedecked with Warhol's portraits of Pat Cleveland, and you find yourself face-to-face with a piece from Richard Prince's 'Nurses' series as you wait for a cappuccino. "Oh. Totally normal, then." You ascend the first winding staircase, only to be greeted by a gallery wall brimming with too many contemporary pieces to count, with a Damien Hirst statue and Francis Bacon painting tucked into the corner for good measure. To your left, the living room, complete with two Jeff Koons installations in opposing corners and flanked by baroque-y touches like an enormous chandelier and an ornate gold mirror. To your right, an all-black-everything library, with cozy black leather wraparound couches, a dinosaur skeleton hanging from the ceiling and a bust clad in what could easily be a Balmain matador's outfit culled from Michael Jackson's closet. Upon closer inspection, you notice silver skulls by Hirst peeking out from between the vast array of art history books along the bookshelves. If that's not a testament to Boardman and her family's approach to collecting—being that they actually live with the art they collect, and in turn, enjoy it—we don't know what is. Oh, and guys? Please note that we haven't even gotten to her closet yet (or the game room, complete with walls full of Warhol portraits and a terrace overlooking East 80th Street). Whizzing up a few floors via elevator (alternately, you can take the stairs, where we spied a few George Condos), we finally made our way to Boardman's wardrobe. Turns out she takes more than a few cues from the art lining her walls in her daily dress—her wardrobe was a Basel-ready assemblage of all-over print confections by the likes of Dolce & Gabbana and Valentino, with emerging designers like Tata Naka, Katie Ermilio and Stella Jean throw in for good measure (courtesy of a little help from pal Lauren Santo Domingo's Moda Operandi). Oh, and as if that wasn't quite enough to take in, the family has a second home in Southampton—is it too early to ask for a Round II already?