Cover art for podcast The Freelance Podclass

The Freelance Podclass

86 EpisodesProduced by Craig CanningsWebsite

The Freelance Podclass is not your ordinary podcast! It features a series of actionable lessons designed to help you solve the biggest challenges you are facing in launching and growing a profitable Freelance Business. Join the founder of Freelance University, Craig Cannings, and an amazing faculty … read more


The Winning Clients With Upwork Class with Winton Churchill

In this class, I’m joined by the founder of Barefoot Consultants, Winton Churchill, who shares some important strategies on how you can win new clients using Upwork. We discuss how to overcome being new and unknown in the Upwork entity and which job areas see the most success. Winton also shares some exciting stats on the growth and popularity of freelancing that show great promise for the future.


Podcast Outline:


0:00 - Opening thoughts

0:46 - Introduction to Winton Churchill

2:51 - Winton’s name and the opportunities he’s had because of it

5:42 - How Winton got into the freelancing and training space

8:20- How Craig hired his first designer on Elance and started working virtually

9:02 - Dispelling the misconception that Upwork is a saturated marketplace


9:41 - What buyers like in a freelancer:

  •   9:56 - A comprehensive profile
  • 10:18 - No “I” profile (“I did this, I did that, I was here, I was there…”)
  • 10:32 - Cultivate three to six clients that you work with on an ongoing basis.
  • 10:50 - How most of the jobs in these networks are “audition” jobs
  • 12:03 - The advantage of following the “audition” process, starting with a small project to land great clients
  • 13:26 - The advantage of paying for the attributes of quality freelancers


15:00 - How people can win clients on Upwork:

  • 15:09 - Example of proofreading
    • 15:18 - Link your skill with the domains of knowledge.
    • 15:49 - Examples of people who specialized in particular types of tasks
    • 17:34 - Realize that the jobs are audition jobs and do small jobs (a 1- or 2-hour assignment, something you could probably do in your sleep).


  • 18:42 - How to overcome being new and unknown in the Upwork entity:
    • 19:17 - Do a comprehensive skills analysis and present the elements of it to your client.
    • 19:41 - Consider life experience too.
    • 20:09 - You have free run of what you like to do. (It’s like an appetizer tray.)


  • 21:04 - Expectations around how many bids you have to do to get the job:
    • 21:27 - Be proactive.
    • 21:39 - Most people bid on 10 to 20 jobs before they get their first job.
    • 22:05 - Proposals on Upwork can be as little as 150 words to about 300 words. (You can edit it for each job situation.)
    • 22:29 - It’s like trying to jump on a moving merry-go-round. (You just have to get that volume of proposals out there before you get the first job.)
    • 23:16 - Don’t give up early on.
    • 23:28 - The value of Upwork


  • 24:38 - Where Winton’s students are finding the most success:
    • 25:04 - Working with words
    • 25:29 - Internet research
    • 26:10 - Skills (like Microsoft Excel)
    • 26:26 - Customer service / Customer support
  • 28:07 - Technology specialization
  • 28:39 - Most jobs are at the beginner-intermediate level.
  • 29:24 - You need to keep learning to keep earning.
  • 30:33 - How the pathway to new opportunities can be fairly short because of courses
  • 31:18 - Example of PowerPoint presentations
  • 32:56 - How one small project can turn into a long-term client relationship
  • 33:30 - Don’t look at jobs; look at the client for ongoing potential.


34:29 - How many marketplaces people should focus on

36:22 - The importance of using many different strategies to build your client base

36:45 - Rumors about possible changes to LinkedIn

37:27 - The growth of freelancing in the United States

39:14 - How freelancing is becoming more mainstream and popular

39:46 - Final thoughts and how to connect with Winton

Resources and tools discussed in this episode:


Winton is providing three awesome resources:

1. Five Tips to Becoming a Top Freelancer

2. How to Succeed on Freelance Networks

3. Finding Your Golden Goose (AKA High Paying Clients)

Here is the link to the above FREE resources:  



How to connect with Winton:


The Wall Street Journal: 

Entrepreneur Magazine: 








Microsoft Excel: 

Microsoft PowerPoint: 











MIT Media Lab: 

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