As Republican presidential nominee Donald Trump heads into the New Hampshire primary, he is facing a challenge to his brand. He sells himself as a winner, yet the top story following his second-place finish in the Iowa caucuses is that of a sore loser.

The day after Iowa, Trump started blaming the outcome on the media and on caucus winner Ted Cruz, accusing him of fraud. Then Trump turned on voters, tweeting "I don't believe I have been given any credit by the voters for self-funding my campaign, the only one. I will keep doing, but not worth it!"

Trump has a history of minimizing past business failures, painting them instead as minor losses or even victories.

"If he does it, it’s not failure, I think is kind of the basic equation," said Gwenda Blair, author of The Trumps: Three Generations of Builders and a Presidential Candidate.

An early notable failure was his project at New York's former west side rail yards. In the early 1990s, Trump compromised on a proposal to build on 56 acres between 59th and 72nd streets. He initially called it Trump City. It was to include a 150-story building and an enormous shopping mall. But he couldn't get the deal past residents and city officials.

"We were tough negotiators....we won most of what we insisted on," said Ruth Messenger, the Manhattan Borough President at the time the deal landed. "It’s fair to say [Trump] was a little surprised that we had no intention of backing down."

By the time the deal was sealed, the development was half the size of what Trump had initially proposed, and also included concessions to the community, including a costly park. But the billionaire focused only on the positive.

“It’s a magnificent facility, we’re building a development that’s going to be world renowned, I think it will be the greatest development built since Rockefeller Center," said Trump of the compromise.

Trump was forced to give in because he had too much debt on the property. Likewise, debt did him in when he lost the Plaza Hotel, filing for Chapter 11 then ultimately selling it for less than he'd paid for it. Outside debt also played a part in his casino losses.

But Trump defends his bankruptcies. 

"On four occasions I’ve taken advantage of the laws of this country, [just] like other people, I’m not going to name names because I don’t want to embarrass," he said during a debate on Fox News.

Trump laid out his philosophy on being successful in a motivational speech that has been posted online: Think big and never give up. He also offers some advise that might foreshadow the challenge he faces tomorrow in New Hampshire. 

"If you don't have momentum, you will not have what it takes to get the job done," Trump says on the recording. "Patience alone isn't enough."