I was gonna make a comment on this pic, but just thought I’d check the previous comments fir—
 
@HydroFTT  

 
…there it is. :)

@Background Pony #165A  
Being ‘old money’ is a fairly distinctive trait, and could easily be the main thing that separates mister Filthy from the average pony.

Filthy Rich and family’s cutie marks are literally having money.  
It is possible, though, that Filthy doesn’t actually own a chain of stores (we never actually see a Barnyard Bargains, everyone always buys from artisans or specialty store owners), and Filthy Rich only pretends to be bourgeois to conceal the truth that he spends all day sitting on his couch eating Zap Apple jam and magically finding coins between the cushions.

@MetaKnight145  
See, thing is there, no one gets a cutie mark in ‘being a business owner’; They get cutie-marks in TALENTS, and usually fairly specific ones (Cheerilee’s mark is related to helping her students ‘bloom’; Presumably, she has no special talent for paperwork and such, even though her job probably involves at least some. Heck, ‘RD’ is generally either a weather-mare or an aspiring Wonderbolt, but her talent is essentially being a really good flyer - heck, it’s even canonically established she’s got bad stamina, though she’s working on it, and after working hard on a routine for the Best Young Fliers competition she still screws it up due to stress. Point being, RD doesn’t seem to have a talent in being a stunt flyer; She’ll have to do that with hard work, backed with a talent in flying in general.)  
They sometimes identify it as such, but that interpretation could be wrong.  
Do some ponies have more valuable skills and therefore end up richer? Sure.  
But for the most part, you’d get a cutie-mark that represents what your talent is, with a SPIN based on the specific use.
 
So, in your example, let’s say one pony has a talent for leading and has a strong drive towards success.  
They become a business owner, compete with other ponies with the same-ish talents (so they’re practically mark-less in terms of how much it matters), and become rather wealthy because leadership is a very valuable skill (getting two workers to work 10% harder is as valuable as a worker who works 20% harder by themselves. With ten workers, each 10% difference in workers just requires 1% motivation/efficiency from the leader for them to be of equal value. Get a whole franchise, and you barely have to beat the average to be the company’s most valuable asset)
 
Nopony is going to get a cutie-mark in being a stockier; It’s not the kind of job you aspire to.  
Either they tried something else and failed (maybe they’re a great soldier, but trauma and stress made them retire. Or any number of other reasons they can’t use their real talent), or they don’t care that much about their job (not all people/ponies obsess about their job, after all; For some, their dreams are things they do in their spare time)  
Let’s go with the second, it’s less depressing, and simpler.  
We’ve already seen ponies with cutie-marks that don’t seem job-orientated - the palm-tree one, which I’m pretty sure belongs to some surfer, is one example.  
So, they don’t work as hard as the people whose ultimate dream in life is wealth and status, so they don’t get much beyond working in someone else’s store - Equestria has a lower population density, so probably not quite as menial as you implied, but it’s certainly possible it’d be as simple and repetitive.  
That also means less money and so on, of course.  
But they have a genuine talent in something they love; Maybe they’re the reigning champion in the local chess club, maybe they go down south every summer to have fun in surfing competitions, whatever.
 
Or, I suppose, it’s entirely possible they get drunk on a regular basis, didn’t even finish their schooling back when they were younger, and has made no attempt at fixing their life.  
That would probably leave them worse off.  
But that’s because they didn’t try hard enough.
 
If you want to compare it to the real world, which is a bit silly given they are magical ponies ruled by an eternal goddess, it’s better to compare cutie-marks to subject-talents rather than job-talents.  
So, think about ‘if one person is born with a talent for math, and another has a talent for aestethics, is that fair?’  
Probably both yes and no; See, life is fair in the sense that you had just as much a chance to be born lucky as everyone else (rewarding people completely randomly is always ‘fair’, but not always ‘just’), but if we start counting AFTER you’re born, sure, it’s not entirely fair.  
But, it’s not that bad; If you really want financial security, and find motivation in the thought ‘this will get me money’, you can probably get some design-job with your aesthetics-sense.  
Won’t pay the same as some jobs, because it’s not that valuable a skill, but it’ll easily get you middle-class living if you’re good enough.

@Background Pony #A2C0  
What’s contradicting about the message “extremes are bad”?

@martianmister  
The characters or the writers, take your pick.

@Background Pony #A2C0  
Who?

They ARE sending contradicting messages, aren’t they?

“Why pretend we’re all the same when some of us shine brighter?”

DUEL!

@martianmister  
Well yeah, but in this particular picture it is hard to tell the difference.

@Eeveeinheat  
Aria’s pink, Starlight’s purple.

I just realized that Aria’s coat and hair color is exactly the same as Starlight!

@MetaKnight145  
That’s missing my main point. What I’m trying to say is that money isn’t equal to happiness. Maybe they’re financially unstable but happy because they get to meet with ponies everyday. (& if they hate working at the grocery, why would they have it as their cutie mark?)
 
& you’re also confusing how real world economics work with how they might work in magic horse land.  
We have no idea how realistic it is overall.

@MetaKnight145  
Thing about that though is that from what we’ve seen from the show so far, a pony gets their cutie mark after finding something that they’re not only good at, but love to do too. Sure the extra bits are nice, but ultimately not as nice as doing something you were meant to do. Maybe a grocery bagger might not seem like a good life to you, but to that specific pony it would be a something they wouldn’t mind doing for the rest of their lives cause they enjoy it.
 
And how many rich and powerful people are miserable in real life anyways? More money doesn’t necessarily mean more happy.

@OneOverTwo  
Yes.  
Working at a grocery store for the rest of your life and living in a run down one room apartment because you can’t afford to live anywhere else is such a wonderful life.  
“grocery store working could live a life that’s financially stable”  
>financially stable  
>grocery store  
Pffft.  
He’ll get laid off the moment paying him becomes more expensive than keeping him around. That isn’t stable.

@MetaKnight145  
You do realize that amount of money isn’t directly related to quality of life, right? That business pony could have several enemies constantly breathing down their necks while the grocery store working could live a life that’s financially stable surrounded by friends or something.

@Background Pony #78CF  
Well think of it this way.  
Two ponies are born.  
One gets a mark in being a business owner or something else that makes them a fuck ton of money.  
The other one gets a mark in being a stockier at a grocery store or some other menial job.  
The first pony will have a FAR better life than the second one and all that determined it was the mark that was predetermined for them, probably right when they were born. Once they get it they are locked into it for the rest of their life. There isn’t a single thing the second pony can even try to do about it because in a society where everyone has a mark on their ass that says what they do with their lives there isn’t much hope for moving up in the world no matter how hard they work.  
This will not come up in the episode, however, because it is just a kids show. And they won’t understand that.

Now that’s funny

Actually, I kind of like this setup. I like it when villains have opposing goals. It’s quite revealing actually because whoever you end of rooting for reveals something about you. When neither side can be called heroes it forces you to pick one based on factors you wouldn’t normally consider. Even whichever you say is the lesser of two evils says something about your values.

@Phantom Rider  
Her colour scheme is based on Twilight’s.

@Phantom Rider  
Nope, just lazy character design.

Is there a plot-based reason for making her look exactly like Aria, or what?

Ahem…  

@Inkan1969  
Not a bad theory…unlikely but definitely plausible.