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RE: How do I increase my Steem Power? Winning it or buying it?
Just hit 500 earlier in the week through a combination of everything you mentioned. The most important thing is to maintain the quality of your posts and curation effort. Can't really tell you when to buy and sell Steem. Eventually through upvoting and commenting you will slowly build a following. I'm definitely more active with followers and people who upvote back then people who just expect a freebie and I'm certain dolphins and whales are the same.
Thanks for comment, you have one more follower!