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What's harder? (opinions and experiences accepted)

Sell lots of low-priced or a few high-priced items?

I started two "successful" side projects in the past, both of them subscription based and both of them low-priced (one had only one plan for $ 4,99, the other an average subscription cost of $ 29).

As I am working on my next project, I was wondering about pricing and this question came to my mind.

What's harder? Sell one $500 item/monthly subscription or fifty $10 items/subscriptions? (numbers are totally random, as an example).

Let me know what you think about it.

on June 19, 2019
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    Note that $500/month is not high-priced. Let's start talking $5000/month and up.

    Still both low-price and high-price strategies are difficult to execute. It is just a matter of what you are comfortable with: customers you like to talk to, people you like to work with, dealing with the ups and downs of loosing a customer, etc.

    Here some pointers:

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      thank you for your thoughts.

      My numbers were just random numbers but I didn't limit the topic to B2B companies and $500 for consumer goods is definitely a high-price.

      No strategy is easy to execute, I agree. I will read both the articles.

      Thanks a lot for your time.