Why do incumbents, especially those in higher offices, start with such advantages? One reason is that many of them have staff who, if they're good, look out carefully for their bosses, and seek out opportunities. Like this, from the Silverton Appeal:
Josh Thomas, a Silverton 12-year-old, had won a writing contest held by Inc. magazine, the Best Lemonade Stand in America Contest; Thomas wrote in about his own lemonade stand (Josh’s Old Fashioned Lemonade Stand, which seems to have grown into a small cottage industry). The award landed him on a Portland radio talk show. Then:
"While he answered questions and shared laughs with the radio hosts, he got a second surprise as Senator Gordon Smith, R-Ore., came on the line and offered his own congratulations and offered Josh the best of luck with his future business ventures."