Talking with Alex Calderwood about his career arc, one gets the sense that he's a born entrepreneur. It’s not because the Ace Hotel chain that he and his partners (Wade Weigel, Doug Herrik, and Jack Barron) manage are substantive, interesting, and innovative, and therefore wildly popular right now, but because every venture Calderwood has involved himself in since his early 20s -- from dealing in vintage clothing to opening barbershops and event-promotion companies -- have been a succession of blockbuster success stories. Calderwood’s latest ventures, the Ace Hotel New York and Ace Hotel and Swim Club in Palm Springs, added a burst of creative energy to midtown Manhattan and the gay-friendly sun belt. For now, Calderwood is happy to continue building a hotel empire with soul. But knowing what we do about his inherent instinct for business, don’t be surprised if you see his name attached to more than just fabulous hotels in the future.