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I have often thought of what you do as being similar to how Bill Simmons started. Simmons always made it a point to pay for his own tickets to games and essentially do nothing like traditional media. His goal was to be a columnist without waiting in line for 20 years as a reporter. I think the primary difference between his arc and yours is that he went to ESPN and then started doing things on his own when he was able to attract investors to do so. Like if you had gone to the News Gazette for a few years and then started the current version of Illiniboard. Maybe you need to find a way to be 'you' inside of a Illini sports machine for awhile. Benefit from the support and access, continue to amass readers and then re-open your small business with more clout, financial support and clarity.