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.
Even so, do you think that money that you can get is pretty much enough for you? I guess not! I think that if you want to get rich, you should have a profession that you like. As an example, if you are a photographer or videographer, you can get some money using a side hustle work.. As an example, the tips https://themoneymix.com/side-hustle-ideas/ that has helped me to understand a lot of sources of income were pretty much enough for me, so I guess they are really good for me as a person who looks for it. It's great!
Yes. If you work at it, and you define "enough"
My salary from Adaptavist puts me into an earnings bracket that I, personally, am happy with. I could earn more, and in fact, I used to, but I've given up some of the money for various reasons that make me happier than the cash would. So it's "enough" for me at the moment.
But I had to work to get to both of those roles, and work harder to keep them.
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.