IDEA TENNIS

IT #33: The Real Reason You’re Broke in Business (Bad Cashier Syndrome) 🎾

Jessica Velez-Benito & Asher Wright Season 1 Episode 33

Are you undervaluing your business by giving too much away for free? In this powerful episode of Idea Tennis with Jessica & Asher, we explore the hidden trap of being a “bad cashier”.... avoiding the ask, downplaying your worth, and feeling awkward about charging for your services.

🎯 Here’s what you’ll learn:

  • Why entrepreneurs struggle to confidently ask for payment
  • How to stop fearing the word sales and start embracing value
  • The mindset shift from needing clients to choosing clients
  • Practical strategies for pricing, positioning, and closing with confidence
  • How to attract customers who actually value your work

Jessica and Asher get real about their own struggles, share personal stories, and unpack what it takes to stop being a “bad cashier” in life and business. If you’re an entrepreneur, solopreneur, or small business owner ready to unlock your worth, this episode is for you.

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*Recorded July 7th, 2025 
*Views are our thoughts, opinions, and experiences, not financial, medical, or legal advice.

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