How To Talk About Money Without Feeling Uncomfortable

In this episode of Cashflow Diary, host, J.Massey, discusses how you can talk about money without feeling uncomfortable during the conversation.  Talking about money makes many people uncomfortable, and many choose to avoid it altogether....

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Now, let's dive into today's episode...

In this episode of Cashflow Diary, host, J.Massey, discusses how you can talk about money without feeling uncomfortable during the conversation. 

Talking about money makes many people uncomfortable, and many choose to avoid it altogether. However, when you run your short term real estate empire, you will inevitably have to communicate about money. It is important to remember that most people need the financial understanding you do and to keep that in mind, so your communication is clear and effective when conducting your business.

Also in this episode:

  • Why I avoid using financial jargon
  • Communication is sent to proceed and properly interpreted
  • Your attorney's role in your short term real estate empire
  • The process of getting the money into the business

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About Cashflow Diary™ 

Jay Massey is a full-time Real Estate Investor, Entrepreneur, Popular Podcast Host, Author, Speaker, Coach & All-Around Problem Solver.

Cashflow Diary is a short-term rental hospitality training company. We show people how to build their own short-term rental business (without needing to buy or own any property) so they can thrive financially.

Heralded as the most advanced short-term rental training in the industry, Cashflow Diary enjoys creating content and communities that are solely focused on developing individuals into powerful business owners. Founded by J. Massey, Cashflow Diary exists to create short-term rental entrepreneurs. No matter your passion, he believes that running a hospitality business will change people’s lives…

 Cashflow Diary is here to share all of it with you.



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  • Turning awkward "asking for money" into offering genuine opportunities
Investors who use this system are raising $100K-$500K from people they already know, often within 30 days of implementation.

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How To Talk About Money Without Feeling Uncomfortable
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