From Getting Fired to Getting Paid with Caitlin Pyle

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On this episode of Rhodes to Success, I interview Caitlin Pyle, who is a former freelance proofreader turned entrepreneur. Caitlin is a millennial who used to earn $3-5K a month doing part-time work, but tapped into the power of the internet and built her online business from zero to over $500K in 12 months. During this episode, Jessica and Caitlin discuss making mistakes and entrepreneur traps, the transition from the trenches to entrepreneur, taking stock of success, and dealing with online business and haters.


Main Questions Asked:

  • Tell us about your big failure.
  • What were your next steps after the big failure?
  • What do you think about ‘follow the passion’ versus ‘follow the money?’
  • What was the transition from proofreader to entrepreneur like?
  • Who inspired you when you first started your online business?
  • Talk about your businesses and how you are helping people.


Key Lessons Learned:

Making Mistakes & Entrepreneur Traps

  • Everyone teaches you how to get a job, but no one teaches you how to quit a job
  • Sometimes you think and work as an entrepreneur before you are one.
  • Weigh up whether you want to get paid for the value you offer or paid by the hour.
  • When people want to become an entrepreneur, some fall into the trap of asking ‘what looks sexy?’
  • Many budding entrepreneurs look at what they think they want to do and their passion rather than where the money is.
  • Follow the money, figure out how to make it work for your life, and enjoy it.


Transitioning from the Trenches

  • When you become a successful entrepreneur, most likely you are not still doing the thing your business does.
  • Ensure the level of service to your clients is like none they have ever received before and remain active within your client community.


Look How Far You’ve Come

  • Entrepreneurs often only think of what’s next and do not look at the progress.
  • Take a moment to reflect on what you have achieved in the past week, month, and year.
  • If you’re not embarrassed by the first e-book, video, or podcast, then you waited too long to release it.


Online Business & Haters

  • Prepare yourself for haters. This is magnified when you do business online.
  • Be careful how you treat your staff, clients, and customer relationships online.
  • People that leave reviews are those who love it or had a horrible experience, but not those who just had a good experience.
  • Avoid the ripple effect with clients and manage the issue quickly to avoid them spreading negative opinions.


Proofread Anywhere

  • Online course: Transcript Proofreading Theory and Practice.
  • Multimedia course with downloads and worksheets.
  • The full course takes 2-4 months with more than 50 practice transcripts and 3,000 pages.


Subscribe to the show in iTunes or Stitcher Radio!


The music in today’s episode was written by The Danger Os and produced by Nick Palmer. Check them out at 


Links to Resources Mentioned

Proofread Anywhere

The Work Anywhere Life


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Follow the passion vs follow the money. Which is best in entrepreneurship? Find out w/ @caitlinpyle @JessRhodesBiz

What is the biggest mistake budding entrepreneurs make? Find out w/ @caitlinpyle @JessRhodesBiz

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