I've spent the majority of my adult life either self-employed or in school studying the actions of consumers from a business, then a psychological perspective.
Most media outlets saw this as a floundering Trump campaign, or focused on him reneging on his self-funded campaign promise.
'Desperate' pleas for fundraising are a political staple, but usually focus on schemes like 'we need 50 people (or however many) in your area' or 'donate even $1 to help stop our opponent.' Rarely do you ever see an actual target (unless it's saying 'we've been outspent by our opponents by this much'), and definitely you don't ever see such a low amount.
I saw this as a marketing ploy, not a cry for help from a floundering campaign -- and here's why:
If You Want to Make Millions in Business, Break It Down to the Smallest Possible Amounts
It's just like eating the proverbial elephant, you do it one bite at a time.
From a business perspective, when you make money you often think about how to earn the smallest 'bites' of money, which add up to huge piles of money in the bank.
It didn't make sense for Trump's campaign to ask for $100k for national ads to attack Hillary Clinton. Ads on national TV cost in the millions not thousands of dollars. One-hundred thousand dollars might buy a few seconds of ad space, not enough to do any good.
Also, it hardly made any sense that Donald Trump couldn't (or wouldn't be able to) write a check for $100k to sustain his campaign if it was really needed, and not have to make a desperate appeal to small donors.
So why ask for only $100k?
Perception is everything.
If you want raise money a few dollars at a time, say $10 to $100 from each person, from a business perspective you wouldn't ask your donors for $10 million. Many would see their $10 contribution as meaningless and just have a 'why bother' approach.
But if one million donors replied to your appeal for $100k, then all of a sudden you've raised $10 - $100 million in hard cash, in small donor contributions.
From a marketing perspective this is brilliant, from a political perspective this is almost foolish.
You Don't Care if You Look Foolish in Business . . .
There have been plenty of business men and women who have been scoffed at for their ideas, only to get the last laugh as they deposited their millions in the bank.
In business, the final judge of 'worthiness' is whether the idea becomes profitable, sometimes even how high the person climbs on the Forbes list of billionaires.
It doesn't matter if they looked foolish at times doing it, scoffers abound at new ideas that eventually pay off big.
But once again, this is another reason why entrepreneurs make poor politicians.
In politics, your persona is your only salable product.
If you damage your persona, by making yourself look foolish, unscrupulous, or amoral, you take the risk of damaging your marketability to your voters, often losing the only measure of success -- the ballot box.
Trump Can Only Win on His Prior Persona, A Cocky Billionaire With All the Answers
This strategy has made Trump's campaign look weak, something the Republican Party and voters are now having to deal with from the media, ever hungry to make him look stupid at all costs.
The appeal that Trump has always enjoyed from his supporters has been based on his overwhelming persona as a business leader and entertainment mogul, and the belief that 'he speaks his mind' on issues important to his base.
While his campaign might have had the most brilliant business decision to ask for $100k to raise significant funds, he's damaged his overall credibility. Not just with the media who is quick to judge and mock him, but with his supporters who looked to him for cocky arrogance that would have the answer for every dilemma our country might face.
If Trump wants to eventually win the POTUS, he's going to have to be careful not to damage his persona and 'brand.'
Because laughing at your scoffers on your way to the bank is a whole lot easier than winning an election with a damaged persona and discouraged supporters.