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Dropping $40K on NFTs pray for me
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Can I get some likes please

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It doesn't hurt to bring it up, but I would suggest finding out what kind of cost would be involved and how it would be better with saving time or whatever the benefits might be. It will be a lot more meaningful conversation than just mentioning how it's outdated and an upgrade would be better.
I can relate. The company I used to work for, used DOS - 😱 I once communicated to our location manager if it would be possible to research newer software programs that the company could use. He agreed that the system was outdated but if the company was to convert to more modern technology than the company would have to pay more for security protection. The use of DOS made it difficult for clients to get hacked and have their identity stolen.