How JackThreads grew from a bootstrapped bedroom startup to 2M members

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.

An alternative to incubators: the co-working space

If you’re a startup, you’ve probably considered joining an incubator. But residency can be competitive and the requirements stiff. TechStars and Y-Combinator are well-known incubators that offer funding, mentorship, and access to a community of venture capitalists and anointed digerati — but only for a select few. Applicants also have to provide detailed business plans and disclose development, operational, marketing, and sales activities to get into the club.

8 tips for entrepreneurs from a founder-turned-VC

A friend of mine recently asked me a simple question: “After four years as a VC, knowing what you know now, what basic tips do you have for guys like me who are growing venture-backed businesses?” It got me thinking about what I’ve learned being on the other side of the fence – and though I don’t profess to be an expert on how to be the perfect entrepreneur, I thought my own experiences might help some founders out in the trenches today.

Punching above your weight: Tips for small startups taking on the big guys

Boxing, mixed martial arts and wrestling employ weight classes to ensure the competition is fair and you’re tested on skill, not size. In business, weight classes don’t exist, so if your company is a young, skinny 95-pounder, while your industry is filled with 300lb giants, you’re going to need to tighten up your laces and punch way above your weight. If you want to survive these mis-matched fights in today’s saturated marketplace, you need to get comfortable.