I’ll go first! I have two that stick out in my mind.
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As the seasons turn to spring, this eulogy for Camo Cat gets me every god damn time. every. god. damn. time. (Have I mentioned that you should donate to the Internet Archive? Please donate to the Internet Archive!)
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It’s Up to You is why I will be an Amy Hoy fan forever. I met her as a fellow speaker at Webstock in New Zealand 2010 but I didn’t really know who she was. Now I do. Much respect. I also highly recommend her site for bootstrapping entrepreneurs, Unicorn Free.