Trump did the opposite - me told people how he would help them. Trump, like Obama before him, never lost sight of the goal and both dark horse candidates went on to win the presidency.
Hillary had twice the campaign funds as Trump but she only spent a fraction on ads promoting herself and those only told how she had fought for children all her career. The vast majority of her ads were aimed at telling us that Trump is a bad person. Like taking chess pieces, negative ads can put you in a stronger position but they miss the goal of convincing enough people to vote for you to win the Electoral College.
What Hillary forgot was that the goal of the debates was not to score points on your opponent. It was to convince the voters that they would be better off with you in the White House. Trump spent most of his opening statement explaining why renegotiating treaties would help put people back to work.
Once you look at it this way, you can see several aspects of Hillary's campaign that showed the wrong strategy. Look at the first debate. The accepted wisdom was that Trump needed to act presidential and keep from losing his temper. Hillary was supposed to have consulted with experts on how to needle him and make him lose his temper. In a later debate she made a point of crossing the stage so she could be photographed with Trump looming behind her. Then her staff sent out the picture as an example of how women have to cope with angry men looming over their shoulder.
In both elections, Hillary had the wrong objectives. She went after large states, assuming that wins there would crush her opponents. Both Obama and Trump ran in states that Hillary ignored and, when she didn't do as well in the big states, they passed her.
Hillary Clinton managed to lose two presidential races where she was the front-runner with a huge financial advantage. First she lost the 2008 primary to Barack Obama then she lost the 2016 presidential election to Donald Trump. I had a recent insight into how this could happen - Hillary was using checkers rules in a chess game.There are two major differences between checkers and chess. The obvious one is that the pieces move differently. But that's minor. The biggest difference is that you win checkers by taking all of your opponent's pieces but you win chess by taking the king. Taking pieces in chess is a strategy but it can also be a distraction and it is possible for a player with fewer pieces to still win by effective use of his resources.