Challenger
2 min

5 Challengers Who Failed Before They Found Success

Elizabeth McCumber
Senior Writer & Content Strategist

We love to celebrate Challengers—those who think differently. But oftentimes that means trying and failing. While we love to highlight big wins and ground-breaking achievements, behind those successes are countless failures.

Here are a few of our favorite failures:

  1. Joe Gebbia from Airbnb told the company’s growth story on NPR’s podcast How I Built This, sharing that when the founders were in serious debt, the creation of a political cereal “Obama O’s” actually funded the business during their first years. Joe credits this hustle for getting Airbnb into the prestigious seed accelerator Y Combinator.
  2. Ring founder Jamie Siminoff went on Shark Tank to get an investment for his home security company and didn’t get a deal. He continued growing the business on his own, and only a couple years later Amazon acquired the company for $1 billion.
  3. The 2002 documentary Lost in La Mancha chronicles director Terry Gilliam’s attempt to make a Don Quixote movie. After overcoming numerous hurdles, he made a new version of the movie to be released next month.
  4. The award-winning documentary Searching for Sugarman chronicles the rise of musical artist Rodriguez. The 1970s American singer was virtually unknown in his home country, but continued creating and became a massive success in South Africa.
  5. Entrepreneur Jack Dorsey shows how success isn’t linear–or defined by anyone else. As a co-founder of Twitter, he was actually removed from his position as CEO. He then started payments company Square. He later returned to Twitter and is the current CEO.

We love these examples of failures because they remind us to keep up the hustle. Ready to Think Like A Challenger? Let’s talk.

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