After working from his bedroom for two and a half years, Jason Ross launched JackThreads — a men’s online shopping club that had yet to establish a payment system via credit cards — in 2008. His first online sale featured a single brand and only sold three items, but the company quickly acquired several hundred members in the first three months. Today, JackThreads has almost 2 million members, over 500 brands and over 60 employees. The flash-sales company was bought by Thrillist in 2010 for an undisclosed amount, but Ross continues to lead the company’s daily operations. Here, Ross shares his highs, his lows, his best advice and what he thinks is next for the online retail industry.