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BigMax
Fine Arts - Two hundred uploads with a score of over a hundred (Safe/Suggestive)
The End wasn't The End - Found a new home after the great exodus of 2012

I don’t think many other ponies did that, or his fame as a troblemaker would have preceded him.
Like, say, the Flim Flam brothers? They seem to pull all kinds of stunts on the unsuspecting public all the time. But ponies are forgetful, and don’t generally make a huge deal out of these things. Even world-shaking events are quickly ignored with them.
 
How’s that the same thing? The first time we saw F&F was with an awesome contraption that actually worked quite well, until they made a mess out of it.  
We’ll see what happened to their reputation after Leap Of Faith.
 
Iron Will never changed his business as far as we know it. We can only suppose it has some effectiveness.
 
That kind of charlatans usually want to be paid in advance and don’t offer the chance of a refund. That’s not what Iron Will does.
Not true. Thousands of would-be Napoleon Hill clones have made plenty of money in what is technically an honest way.
 
Iron Will doesn’t see a book. He sells his lessons, which are not paid in advance. And only if the customer is satisfied.
 
And she behaved quite… oddly, to say the least. She even locked herself inside her house, not giving any notice to Iron Will.
She wasn’t obligated to tell him anything. As far as we know, Iron Will always makes house calls to collect his fees.
 
I wouldn’t say “always” since we’ve seen only one case. That doesn’t make statistically sense. When we’ve seen him doing it, he was not in some kind of fee collecting tour: in fact, he went to do groceries after his first attempt at Fluttershy’s.  
And yes, she was obligated to either pay him or tell him she wasn’t satisfied. But she missed to do so, and the quarrel happened. Iron Will only visited her when she was overdue, with either a payment or an answer.
Background Pony #E485
What he does is improving the assertiveness. Making money is a direct consequence. Achieve the former, also achieve the latter.
Like Adam Smith said, “It is not from the benevolence of the butcher, the brewer, or the baker that we expect our dinner, but from their regard to their own interest.”
I don’t think many other ponies did that, or his fame as a troblemaker would have preceded him.
Like, say, the Flim Flam brothers? They seem to pull all kinds of stunts on the unsuspecting public all the time. But ponies are forgetful, and don’t generally make a huge deal out of these things. Even world-shaking events are quickly ignored with them.
That kind of charlatans usually want to be paid in advance and don’t offer the chance of a refund. That’s not what Iron Will does.
Not true. Thousands of would-be Napoleon Hill clones have made plenty of money in what is technically an honest way. They write a book, and people can do with them whatever they’d normally do with any other kind of product they buy. The fact that it’s all “above board” doesn’t mean it’s actually a good, worthy product. These books are often filled with lies and manipulation geared toward brainwashing people into thinking they got something great, when in reality they just wasted their money on cheap platitudes and sketchy advice.
And she behaved quite… oddly, to say the least. She even locked herself inside her house, not giving any notice to Iron Will.
She wasn’t obligated to tell him anything. As far as we know, Iron Will always makes house calls to collect his fees.
BigMax
Fine Arts - Two hundred uploads with a score of over a hundred (Safe/Suggestive)
The End wasn't The End - Found a new home after the great exodus of 2012

@BigMax
>And his intention is to improve the others’ assertiveness, nothing else. Fluttershy apparently took it in the wrong way, so that’s mainly her problem. The “new” Fluttershy indeed is the sole antagonist.
You are so very, very mistaken. His intention was to make money, how could you miss that.
 
What he does is improving the assertiveness. Making money is a direct consequence. Achieve the former, also achieve the latter.
 
Fluttershy followed his instructions at every turn, and it was all terrible advice. She didn’t take anything in the wrong way, that is so ridiculous.
 
I don’t think many other ponies did that, or his fame as a troblemaker would have preceded him.
 
>You may argue that it’s because of Will’s teachings, but if they were a common problem, then Iron Will wouldn’t have been the successful motivator he seems to be.
Are you serious? Hustlers like him get successful all the time. The “self-help” industry is rife with examples of highly profitable authors who are, in essence, ripping off their customers with a lousy product.
 
That kind of charlatans usually want to be paid in advance and don’t offer the chance of a refund. That’s not what Iron Will does.
 
>He gave up on being paid because of his own crystal clear rules. Running a business also means staying loyal to your contracts. You don’t want to risk to be considered an unreliable contractor.
And there’s also the whole getting sued or arrested problem to worry about.
 
That would be part of the reliability problem.
 
>Sure, many might have not responded because they remained timid ponies, but we have no clues about it.
Other than the fact that we clearly saw that he threatens ponies who even hint at being unwilling to pay him.
 
We don’t actually know. We just have Fluttershy’s experience on the matter. And she behaved quite… oddly, to say the least.  
She even locked herself inside her house (how the heck did she nail those boards?!), not giving any notice to Iron Will.
Background Pony #E485
@BigMax  
For the record, I see Iron Will as a massive jerknozzle, not an antagonist as such. Neither was Fluttershy. She obviously doesn’t really have anything against her friends. Rarity and Pinkie understood that Fluttershy was only behaving the way she was because of Iron Will, and they said as much.
 
>Iron Will isn’t against anyone, except those who don’t pay him – which is perfectly understandable  
What is NOT “understandable” is acting like a complete thug about it, threatening violence and manhandling people. No collector should get away with that in a civilized society.
 
>And his intention is to improve the others’ assertiveness, nothing else. Fluttershy apparently took it in the wrong way, so that’s mainly her problem. The “new” Fluttershy indeed is the sole antagonist.  
You are so very, very mistaken. His intention was to make money, how could you miss that. Fluttershy followed his instructions at every turn, and it was all terrible advice. She didn’t take anything in the wrong way, that is so ridiculous.
 
>You may argue that it’s because of Will’s teachings, but if they were a common problem, then Iron Will wouldn’t have been the successful motivator he seems to be.  
Are you serious? Hustlers like him get successful all the time. The “self-help” industry is rife with examples of highly profitable authors who are, in essence, ripping off their customers with a lousy product.
 
>He gave up on being paid because of his own crystal clear rules. Running a business also means staying loyal to your contracts. You don’t want to risk to be considered an unreliable contractor.  
And there’s also the whole getting sued or arrested problem to worry about.
 
>Sure, many might have not responded because they remained timid ponies, but we have no clues about it.  
Other than the fact that we clearly saw that he threatens ponies who even hint at being unwilling to pay him.
 
In summary, Iron Will was not out to “get” anyone, he’s just trying to make a buck Rex-kwondo style. Fluttershy didn’t set out to hurt or hassle anyone, she was “trained” by Iron Will to act like a jerk, and that behavior was initially reinforced by her unwise friends. And let’s not forget that Pinkie and Rarity acted like swindlers themselves at the beginning, and the whole of Ponyville seemed to be determined to act uncharacteristically obnoxious.
 
Hopefully, Williams never writes for MLP again.
BigMax
Fine Arts - Two hundred uploads with a score of over a hundred (Safe/Suggestive)
The End wasn't The End - Found a new home after the great exodus of 2012

@Background Pony #FDE8  
That doesn’t sound quite right to me.  
An “antagonist” opposes someone or something. Iron Will isn’t against anyone, except those who don’t pay him - which is perfectly understandable from someone who’s running a business.  
And his intention is to improve the others’ assertiveness, nothing else. Fluttershy apparently took it in the wrong way, so that’s mainly her problem. The “new” Fluttershy indeed is the sole antagonist.
 
You may argue that it’s because of Will’s teachings, but if they were a common problem, then Iron Will wouldn’t have been the successful motivator he seems to be.
 
He gave up on being paid because of his own crystal clear rules. Running a business also means staying loyal to your contracts. You don’t want to risk to be considered an unreliable contractor.  
Sure, many might have not responded because they remained timid ponies, but we have no clues about it.
Background Pony #E485
@Lawful Girly  
>graciously
 
lol. “New Fluttershy” was only following his advice, so if she’s an “antagonist”, so was Iron Will. He didn’t back down because he respected anyone, he did it because he just didn’t have any recourse. You could see how uncertain he was how to respond, because apparently Fluttershy is the first person who didn’t respond to his intimidation.
Lawful Girly
Not a Llama - Happy April Fools Day!

@BigMax  
Indeed. We can see that he respected her property, and he kept his promise by graciously backing down from his demand for repayment. It’s likely he’d do the same for anypony else with similar issues. He really wasn’t a villain, and arguably perhaps not even the antagonist–that could be New Fluttershy herself.
Muffen-Man

@Moose Rage  
If you’re here to look at mares in skimpy clothing, then yes.
 
Gilda had a problem with everypony the same way she had a problem with Pinkie, so I don’t count her as Pinkie’s rival, she’s RD’s because she challenges RD’s loyalty.
Background Pony #53C9
Suri - Anti-Rarity  
Lightning Dust - Anti-Rainbow Dash  
Trixie & Sunset - Anti-Twilight  
Gilda - Anti-Pinkie with some Anti-Rainbow Dash
 
We still need a (female) Anti-Applejack and an Anti-Fluttershy.
Antonyourknee
Non-Fungible Trixie -
My Little Pony - 1992 Edition
Wallet After Summer Sale -

A waste of biomatter
@Psychopomf  
Sunset Shimmer:“Don’t try,you hermit or should I say tramp since you got a eviction from an even more angry bloated blue baby. Im the prodigy of the sun itself”!  
Trixie Lulamoon:“Oh yes, of course your one of those fancy “gifted” unicorns that got to play with your horns for years on Celestias bankroll,well I don’t need some degree from some bumbling Professor TO AMAZE AND ASTOUND WITH THE GLORY THAT IS TRIXIE!!!”  
“Pfft…what is that?Can you talk about yourself without showing everypony how insecure and deluded you are? How sparkle put up with this is beyond me.”  
“Oh yes, sparkle.How did you meet her again oh yes you stole her crown cause somepony was a “little” jealous that the sovereign of all Ponydom had a new little pet to play with and hoped having a power trip in another dimension would bring you back to suckle on her flaming teats hmmm.”  
“While I was wearing that crown ,I was experiencing power that surpassed even Celestia!The closes you ever got was when you wore some clashy little necktie that made you somehow an even worse example of a pony who had too much of themselves up their own plot,and speaking about power trips.At least I tried to use that power to conquer the most powerful nation on Eqius…you just used it to terrify some village yokels into making your own self glamorizing Trixieville to sastify your petty revenge scheme,and of course in the end you got tricked into taking the source of your power off cause you still thought the world bent to the “ great and powerful” trixie…am I rigth or am I rigth?  
….“y-you arrogant brat,you threw every good thing you had to had to be a monkey in some mundane little dirtball cause Celestia wouldn’t bloat your own sense of worth!”  
“You peanutbutter cracker eating tart couldn’t get past one pony without spouting lies to inflate their opinion of you just so you can pretend your not some failed unicorn trying to rid ponies of their bits”  
“You would never know what you need to do to survive in the real world,miss I had everything in my life given to me except when I don’t so I throw a tantrum and go on some grand trip to another world to be a Bitch so you feel bad for me.”  
“Harlot!”  
“Nag!”  
“Slut”!  
“Whore”!  
Twilight Sparkle: Girls!Girls! Can’t we just calm down and try to-  
Both: Stay out of this Sparkle!
schpeelah
Perfect Pony Plot Provider - 10+ uploads with over 350 upvotes or more (Questionable/Explicit)

@Master Fox  
There is a Gilda toy, sold in what I understand to be the standard Rainbow Dash set. Considering they had to make an entirely new mold just for her, I expect her to return at some point.
Background Pony #592A
Great!We need just one more, another earth pony, and we have Elements of Chaos!