50 minutes | Jun 15th 2020

Jason Ross: Success Doesn’t Happen Overnight

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The founder of JackThreads and serial entrepreneur, Jason Ross, spoke with host Michael Redd about his early days as a broke entrepreneur, the big gamble of launching (and selling) his own startup, and what it takes to survive the ups and downs of the business world.

"I wrote the business plan and spent two and a half years just working out of my house to get it started." – Jason Ross

Named after his grandfather, Jason founded JackThreads in 2008 – a members-only flash sale site for the streetwear community – and was working out of a bedroom in Columbus, OH.

By May of 2010, Thrillist had acquired JackThreads.com, the startup Jason helped build to $100m in annual revenues and over two million members (he departed in 2014).

JackThreads was listed as one of Ad Age’s America's Hottest Brands, Inc's Fashion Startups to Watch, Entrepreneur's Top Retail Sites and as the fastest-growing men's e-commerce company on Internet Retailer's 500 List.

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In this episode Michael and Jason talked about:

  • The mindset needed to be successful in the face of adversity
  • How Jason rolled up his sleeves right out of college and bet on himself
  • Why entrepreneurship is so iterative and success is not a straight line
  • The genesis of Jason’s bootstrapped, $100m idea (and why he sold it)
  • On the marriage of passion and high-growth opportunities
  • Why you need to surround yourself with the right (and smartest) people
  • And much more!

To ask a question, read the transcript, or learn more, visit MichaelRedd.com.

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