You can get some loot by contributing usefully here. You can make money by writing popular add-ons (sadly, not necessarily "good", you only need to meet the criteria that someone is willing to pay for your add-on). . And, of course, you can take a job with Atlassian (or a partner) and get some income that way.
None of those are "winning money". They're "earning" it. Very different concepts.
Actually, after every closed case with Atlassian you will be sent a survey and by filling this out you are part of a lottery where you can win random prices ($100 gift cards nowdays, but it used to be ipods, and similar).
Like Nic says: Better get a job at Atlassian or a partner if you want to make sure you make something each week.
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