Scaling to failing: Why nothing kills faster than success

“A Doctor becomes and entrepreneur, selling $100m a year in cowboy boots online.” No, it’s not the set up to a joke, it’s the unlikely true story of our guest, John James.

As a serial entrepreneur, John created several online companies that ultimately led to the creation of Country Outfitter, a giant in western wear eCommerce. Today, John shares the lessons he’s learned from being a medical doctor to scaling an eCommerce company. He candidly shares the story of how Country Outfitter ultimately failed and how he had to step down as CEO. However, that is not the end of the story, John is wildly successful again, both in business and life.

We want to thank John for his willingness to share the hard story that no founder wants to talk about. As you’ll hear, John simply viewed this as a stop on his journey that he had the opportunity to learn from. Listen now:

Other topics include:

  • How he scaled an online business while in medical residency
  • How John knew he was destined to become an entrepreneur
  • The processes and systems John used to scale to $100m
  • Where the breakdowns start to happen in businesses as they scale
  • What he did to mitigate the breakdowns and what he’d do differently
  • The narrative most successful CEOs tell themselves and why it’s so helpful
  • The breakpoints in most company sizes (revenue, people, etc.) and where you start to see major issues with culture and productivity
  • Why the CEO can’t be the “Chief Doing Officer” in a growing company
  • Why top-line revenue can be fool’s gold
  • How an external change turned the business on its head
  • Why and how John ultimately decided to step down as CEO
  • What John is doing now at his new company

Don’t miss the next episode of the For You Leaders Podcast where John dives into the event that completely changed the way he viewed his work, family, and life. John also shares a ton of advice around how he thinks about his role as the CEO, the different roles he surrounds himself with to be successful as CEO and making the transition from entrepreneur to executive. It’s a powerful story packed with tactics you do not want to miss

Make sure to subscribe to the For You Leaders Podcast on Apple Podcasts or wherever you get your podcasts. 


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