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Episode two! Yeahhhh!

My co-founding partner of WIMP, Josh Simmons, joins me to talk about all things fail. Josh works full time as a community manager for O’Reilly Media, the best media publisher for web technology (the books with the animals on the covers) AND producer of fantastic tech conferences such as Fluent and OSCON.

Show Notes

Josh and I talk about his experience going from floundering freelancer to doomed start-up and we get to know the truth about what happens when it all hits the fan.

  • Embracing failure
  • Don’t start a company if you suck at freelancing
  • The potential fallout from a failed business
  • Quantifying your overhead – don’t fail to measure
  • Time tracking and estimates
  • Ponzi scheming yourself
  • What it’s like to get sued and go to small claims court
  • Seeing an opportunity vs admitting defeat
  • Finding your calling
  • Taking care of yourself

Josh’s Links

Josh is a community manager at O’Reilly Media

Josh’s WIMP Presentation: Fail Well: Freelance Pratfalls & Coping with Failure

Josh on Twitter @joshsimmons

Josh on LinkedIn


Music: The Naked Freelancer Theme is by Ransom Rath. Listen to the full version here.

All of my podcasts are recorded and edited on my kick-ass Microsoft Surface Pro 3. Visit my tools and equipment page to find out more about what I use for my podcast and my website!

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