Cover art for podcast The Freelance Podclass

The Freelance Podclass

85 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 Selling (Without Being Salesy) Class with Jay Clouse

One of the greatest challenges that most freelancers face, or will face, is the ability to sell their services and sell themselves. This can be a daunting challenge. We may love a lot of facets of freelancing, but many of us don’t enjoy the sales process. Today I’m joined by Jay Clouse, who shares some effective strategies for selling your services without being salesy. Join us as we discuss how to negotiate and have genuine conversations with potential clients, especially during this global pandemic.


Podcast Outline

[0:51] Introduction to Jay Clouse - Jay tells the story of how he got into the freelancing space.

[5:17] How freelancers need to have an entrepreneurial mindset - the importance of treating your craft as a business to make it lucrative and successful.

[7:05] How do you sell your services without being salesy - reasons why the average freelancer dreads the sales and marketing piece of their business.

[9:58] Stereotypes we’ve seen around salespeople and top mistakes people make when selling their services.

[11:53] Imposter syndrome - how it pours into your messaging and conversations and makes you sell yourself short.

[14:04] The importance of negotiation and how it comes from a point of confidence - how the sale is often won before you even quote the price.

[15:26] Should freelancers start charging less because we’re in the middle of a global pandemic? Jay gives advice for how to talk to a potential client, sell yourself, and negotiate.

[21:29] Some channels people can leverage right now to sell services - Jay describes three different routes and provides tips on how to use them.

[26:29] The importance of diversifying and building relationships when looking for clients - how we need to have the courage to be the first person to reach out.

[29:03] How business relationships don’t start with a pitch - Jay explains how they start the same way friendships start and gives advice for how to have a conversation.

[29:51] How do we sell well without being salesy? Jay gives specific ideas for how to sell yourself and provides examples of strategies and conversation topics.

[34:52] The concept of pain points and having the confidence to communicate your ability to reach the client’s goal - how you can go into the conversation with the mindset that the person wants you to be the solution to their problem.

[37:10] Jay shares some final tips about selling in the midst of the global pandemic.

[38:07] How to connect with Jay Clouse


Resources and tools discussed in this episode:

The Freelancing School 

  • Free course: “5 Ways in 5 Days to Make More Money Freelancing”

The Creative Elements Podcast 

Unreal Collective 

The Accelerator Program 


LinkedIn Learning 




Pat Flynn’s SPI community 

Facebook Groups

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