How to start trading?
Now you've bookmarked all those sites I've linked, and read the guides and downloaded all the plugins, what now? Well first in any business, you need to invest something in order to make something, there is no two ways about it. A decent investment (at least $100) will allow you to start trading decently. I recommend the best route to do this is by buying keys off people who are reputable on this subreddit, who sell for around $1.8-2. This is best done via paypal, and will be initially a slow, difficult process as you will have no reputation or rep at this point. You may even want to buy keys off the steam store, however note that these may not be immediately tradeable depending on your payment method. Once you have the keys, look around on the subreddit, csgl, play the game and generally immerse yourself in the community. This will give you some idea of what things are valuable and demanded. Skins which look nice are generally worth more than skins that aren't as nice. Betting skins, such as the AK Redline FT, AWP Asiimov FT, etc tend to be easier to sell just before a tournament, and easier to buy just after.
Once you have a good grasp of what is valued, start making a few trades. Add or message people and offer your keys on their items, and then if they say yes, try selling it for a bit more and voila you have just made your first bit of profit. Now I will go much further in depth later on, but this is the gist of it.
How to gain reputation?
It can be very difficult to gain rep as a beginning trader. There is the catch-22 where people won't sell you things for cash because you don't have rep, and thus you can't get any rep. However, it is very possible to get rep if you present yourself right.
Firstly it helps to have a decently set up steam account. Private profiles are strongly discouraged and most people won't even add you. Private inventories may also be an issue to people. Having an older account and/or a steam level above 2-3 will also make things a bit smoother, as people realise you have invested some time/effort/money into your steam account. As an example I will use my profile. I have a prominently displayed 6 year of service badge. I am level 33, which means I have invested a fair amount of money into my steam account, and I have a lot of hours of a variety of games as well as a lot of +rep comments on my profile. It may even be good to put the country you are from on your profile, given that eastern european accounts have a relatively high rate of scammers, and some people will be more comfortable trading you if you are in their country. Now on the flipside, lacking these things may lead to suspicion of being a possible scammer.
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