Kelly FItzsimmons

E. Kelly Fitzsimmons

Episode 102

How To Navigate Big Failures And Come Out On Top

EP. 102 When we’re in struggle, that’s when our shadow and demons show up and dance.

What happens when you experience a huge failure in business?

For many entrepreneurs, failure brings dark times. We’re so used to wrapping our identity around what we do that when things don’t work out, our self-worth plummets. This episode’s guest found herself in this exact situation – putting herself in $5 million of personal debt. In fact, her situation was so challenging, she found herself in a place where she felt she was worth more dead than she was alive.

This is the dark side of entrepreneurship – a side that’s not often spoken about in public, but it’s a time when business owners need the most support. So after coming out of the other side of failure, Kelly wrote Lost in Startuplandia: Wayfinding for the Weary Entrepreneur – a book written to share her own experiences and insights about the start-up journey.  

So if you’re struggling with failure and you need a boost to help you navigate this all-too-common phase of entrepreneurship, this episode is for you. Tune in now to discover the possibilities that arise when you embrace what failure has to teach you – and how you can survive and thrive, even when you feel knocked down.


When it comes to business success and failure, Kelly has experienced both sides of the spectrum.

Kelly is a serial tech entrepreneur, artist, angel investor, and mother of two. She’s the co-founder of Custom Reality Services, a virtual reality (VR) production company whose first two projects, premiered at the Sundance Film Festival. She’s also the recipient of the Silvertip PwC Entrepreneurship Award and Speech Technology’s Luminary Award.

Check out this episode and discover:

  • The predictable traps for failure – and how to navigate them
  • The reason YOU get to define what failure means
  • Why we’re all liars and how honesty can set you free
  • How a brain injury transformed Kelly’s mindset for life [and inspired her to write her book]
  • What to watch for when sharing your truth with others
  • The dangers of basing your self-worth on your work
  • And more…

Kelly experienced spectacular failure, but survived to tell the tale! In fact, she’s emerged stronger and more courageous as a result of her experiences. Kelly’s story is a reminder that failure in business doesn’t mean the end of the road. Instead, it can be the catalyst for a rebirth and a life lived in more alignment with who you are.

Don’t miss this one.

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E. Kelly Fitzsimmons