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I was recently doing office hours with a company that does enterprise sales and that got me thinking once again on the topic of pricing. So, here's a quick THREAD: (1/9)
(2/9) Founders are all too often afraid to charge MORE, and end up underpricing their products. That fear is generally tied to the fear of rejection, and the fear of losing the deal.

To this, I offer a couple of thoughts:
(3/9) First, it is unlikely you'll lose a deal outright from quoting too high a price. Generally if the customer likes your product/service, they'll at least give you a chance to correct/adjust your pricing -- "oh that's way outside of our budget". Great, what IS your budget?
(4/9) Second, in the event that you DO lose a deal due to pricing, that should not be the end of the world. Your market should be large enough that you do not have to win every single deal to build a huge business.
(5/9) In fact, if you win every single deal, you're probably pricing too low and are leaving money on the table.
(6/9) When founders are not sure how to price their product, I usually ask them to pick a starting price (educated guess, competitor's price, etc), and if they consistently win deals with it, double the price. Repeat until people start complaining the price is too high.
(7/9) That leads me to my next point: It is ok if, in the early days of your business, different customers have different prices.
(8/9) Eventually, you'll have a pricing sheet, but in the early days it is important to discover where customers see the value in your product, and you can only do that through lots of experimentation.
(9/9) TLDR: Charge more!
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