For example, his t-shirts, some of the best selling merch you can have, barely has anything:

Of these eight shirts, there are actually only five designs, and of these five designs only the pink Jimquisition logo and the "Jim F@#&ING Sterling Son" shirts are notable to his brand, and of those the one I could see people buying is the "Jim F@#&ING Sterling Son" design, which is leftover. "Boglin Club" is random and not particularly connected to him, though if it said "Boglin Watch" it might actually sell, actually that is likely why he has leftovers. It is also worth noting we have "preorders" and non-preorders here. The "Something Something Capitalism Bad" just isn't appealing to anyone not super politically charged, same for the "The Gays Can Do Whatever They Want" (here on referred to as "TGCDWTW") shirt.
Though something of note, that TGCDWTW shirt? I've seen multiple other places selling that shirt, including once in Wal-Mart, once in a Spencer's, once at Hot Topic, and once in a fucking H&M. That exact design. So I don't know why it is on his merch store, unless maybe everyone realized that shit like that sells and copied him? I have no clue. Heck, it is apparently even on fucking
Amazon.
Moving on to buttons I want to do in two parts, starting with Pinful Truth, which will also help eliminate many of these designs on stickers too as there's something actually worth saying here and covers the majority of the designs:

I am going to just say, this entire Pinful Truth line seems to actually be Jim trying to diversify his income in an intelligent enough way. These designs seem to be mostly original, and are manufactured by Conrad Zimmerman. It seems that this is basically Jim letting his friend use his store to sell some stuff, and likely taking a cut in return. This is smart business, if only they were smart enough to try and get these things into places like Spencer's or something. These would sell well in such places.
Sure this the designs aren't that clever, it is some pretty by the numbers "rage against the capitalistic system" type shit which I have seen a thousand times, and even partook in when I was a kid, but it isn't awful as a way to make money and the designs work. I'd totally would've considered some of these in my more rebellious youth. This shit works as far as making money, just need to make sure you're actually reaching the demographic that buys this type of thing, and they are able the quickly buy it. I can't fault the idea of trying to swap to such an income source, only the execution, and so far the execution is awful.
Moving on, let's run through everything else button wise.

On this first page, most of this isn't really that great. The logos for his various podcasts is a good call, as all three of them are here, and there's a few buttons that are references to those podcasts (example "Smoke and Sugar Lounge" is a reference to Boston's Favourite Son, as is the "Crabnuts Well Golly" button). I doubt they sell, but it is something to have at least one piece of merch each for, and if being made to order they aren't expensive to have made and ship when it comes up.
I do find it funny that Zimmerman and LKD are both reduced to being only noted as "Podcast Co-hosts" while still getting to sell some merch here, showing that they are both, business wise, hanging onto Jim's coat tails, as he's still the biggest and most successful one among them.
The descriptions of these buttons also seem to say that Conrad also manufactures these by hand, confirming Conrad must own a button press and some blanks. Good on him, shows that Conrad at least has some work ethic, even if all those he surrounds himself with are all lazy troons.
For stuff that I expect actually sell here however, it is the stuff with actual brand recognition. That means the Jimquisition Logo, the Sterling wrestler persona stuff potentially, and the "Trashgirl" pin, which has become a bit of a catchphrase of Jim's. Oh, also TGCDWTW button WILL sell to the LGBTQWERTY crowd and their "allies". Shit like that really does sell. That is probably the smartest thing Jim has on her button wise for trying to move product. The rest I can't see selling that much. The corporate brand snark just doesn't do it. Too niche to disgruntled gamers many of whom are just getting tired of being miserable all the time, and the companies on hand here haven't done anything that have upset a large enough group of people recently that comes to mind. It also just isn't that clever. Nothing else here stands out as something I could see anyone seeing and buying, especially not any of the left overs beyond the "Sterling Logo" one, because well, it is still something his fans would want because it is kinda connected to his brand.

The handful of stuff on the second page that isn't Pinful Truth is all leftover content, and hilariously, I think some of these might be something people would buy. Namely the "Summer of Sterling" as it looks like Jim's old look before the Troon out, and "AAA", because catchphrase. "Pogfucker" also is a bit of his brand with a semi-recurring character back in the day that some people might pick up, just because it is something that was an actual part of his brand and has some style to it, but I doubt it. Really only two of these I could ever see selling, and they are both leftovers, so it isn't like they are selling particularly well.

Look at all the copyright infringement. This shit is in a legal grey area, since technically it is original art and blah blah blah, but I am pretty sure this Pokemon art absolutely could, and probably will, get taken down by Nintendo one day with some actual legal action. I noticed that Jim doesn't sell the old Pokemon shirts anymore, and considering those were from his time on Sharkrobot, I wonder if he got in some heat for them, and that is part of why he isn't on there anymore.

Last two buttons. The "Now Here Me Out Jonathan" is a reference to Boston's Favourite Son again. Which is interesting, as that means that of all his podcasts, that is the one that Jim and Conrad want to push merch of the most. Not Spinoff Doctors, where they talk about video game movies. Not Podquisition, the podcast he does the most frequently that is most closely tied to his primary brand and is the one that is supposedly about video games and Jim's politics and troondom. No, it's Boston's Favourite Son they want to push. The podcast where they actually have the least politics and just have fun with their friend in a purely fictional improvised way. The other would likely be his best selling button if it wasn't at the bottom of page three of his buttons. Jim's most iconic phase, even all trooned up, will also be what sells best for him. "Thank God For Me".
Now the next thing is in the button section, but I want to separate it from the rest, as this is also leading into the thing about the Stickers, which is where I think these were primarily intended to sell. See the stickers and the buttons share what feels like 99% over lap, they just take button or sticker designs, and make the other instead to double the size of their catalogue. One of those are these pride flags:

Now the two lists are identical. Just the names under them is changed. The "Accent" version have some laughs to be had as a result. I will quote the description from the site here, and give a close up of the image listing what they all "sneakily" labeled as:
Accent stickers, inspired by artists references, esports team tags, common lucky colors, scientific metal salt and indicator references, and daily affirmation reminders. Celebrate life in full color and brighten up your space. Vinyl sticker measuring approximately 2.5". Design by Phoenix Toothill. Handmade in the USA by Conrad Zimmerman.
Thats probably enough to fill the page preview. These are identical to the regular items, but in a discreet listing. We know not everybody can be as out and open as they might wish to be. We see you, stand in solidarity with you, and want to ensure your safety as best we can if you'd like to have these without having to explain. What’s inside doesn’t change because of what you're facing outside, and we really mean this: there is absolutely no shame in staying safe first. You are valid regardless of your situation.
Any packing slip / customs descriptions will not show the identity of the flag, or suggest that it is meaningful in any way, however please be aware that the stores name must be displayed on business account postage and customs forms for legal reasons, so depending on the level of surveillance you have to deal with, this listing may be found through searching for 'The Jimporium'
Please note if merch such as the “can do whatever they want” tees are bought alongside these then we will assume that is deliberate, and the packing slip will still show those items regularly.
This to me just seems so brain dead. Like you're ASKING to get found out and in trouble if someone finds this stuff, and Jim knows this could go badly for some people, but he still wants to give them a false sense of security when they buy it from him. It feels almost scummy. Like he is saying he "understands their danger", but he cares more about getting his money, so he still wants them to take risks.
That said, I could see these types of things selling well for Jim, because stuff like this DOES sell well to the alphabet mafia.
Moving onto stickers proper, there's only two here to point at which weren't buttons:


We just have LKD's branding image as a sticker, but sold on Jim's shop (does LKD have his own merch shop somewhere? Why isn't there more on Jim's store if not? If so, why is there any of his stuff on this shop at all then?) and we got "Something Something Capitalism Bad" but as a rather poorly made looking sticker rather than a shirt. I could see the LKD sticker selling to their fans, but otherwise if there was a button design I could see selling that is now a sticker, then I could see the sticker's selling as well.
Next we got the "Pins and Patches" section, which is really just pins, and one patch. I will also include Keychains and PAWGs here, and make this the "All that other merch" section



Ok, so we all see the TGCDWTW thing? Yeah, that's probably going to sell better than everything else here combined, because it actually has a demographic.
Next up we got these enamel pins, those things sell well, they look well made, I bet that is one of Jim's best selling pieces of merch, but I also suspect the old red, white, and black pins from his old colour scheme before he trooned out sold better than these new ones. Also, more LKD stuff, I have to wonder why there's so much Laura on this site, LKD is big enough to have his own merch store, just barely so, but still. The patch only sells, if it sells at all, due to being Jim's actual logo, but since it is the same design as the pin thought I would mention it. Patches just notoriously don't sell nearly as well. The Sterdust pin is sold out, and was leftovers, so that won't get restocked and I doubt it sold particularly quickly to start with, but once again at least Jim turned part of his brand into a pin.
The Capitalism Bad pin however, yeah, that thing looks awful. It is because designs with a lot of thin coloured lines like that don't convert well into being enamel pins, and it it also just looks like a badly manufactured instance, which is extra noticeable with a metallic paint. Also, just like every other instance it isn't that great of a design. It isn't clever, it isn't funny, it probably doesn't even appeal to those who dislike capitalism. It feels like something Jim is trying to force into being a thing. Like he's trying to replace "Thank God For Me" with "Something Something, Capitalism Bad". It just doesn't work.
Both of the PAWGs are silly niche and awful, but I could maybe see someone who was a big fan of Jim buying them to have as display pieces in a frame somewhere, but I can't help but think there used to be other designs that I can't see currently for a larger set. As is, I will be amazed if he ever sells off those leftovers. The design I suspect will sell off first if ever is Summer of Sterling. Though it will be very slow if it ever happens.
Now to get back to something I pointed out, it is odd LKD is selling his stuff on Jim's store, I'd expect them to have their
own store with more merch on it [
Archive], rather than only a single book about being autistic, gay, and trans (since that is all LKD reduces himself to being), and otherwise only selling his merch through Jim. Which if that was the plan, why the hell isn't there more? LKD is verified on several social media platforms. Even if his following is likely, after account for overlapping between various accounts, probably no bigger than 65k people, and since nearly 60k of that is due to twitter and everything else is far less, I imagine he could support maybe a few T-Shirt sales, having a few more button designs, something, anything. It just seems odd that he has so little merch, and that it is all on Jim's shop.
However I don't find it odd that Conrad is selling his stuff here. See Conrad really only has his relationship with Jim when it comes to his brand and own stuff, Conrad isn't really an "influencer" like LKD or Jim are, he could never keep his own shop afloat despite making up the majority of the content on the site due to the Pinful Truth brand.
When it comes to stuff Conrad doesn't do riding alongside Jim, it mostly has to do with his singular game he made, the odd article he writes as a freelancer, and his old days way way back when he was a more active video game critic. He never really took on the term "journalist" he always stuck to "critic". He does some streaming of his own, he actually on rare occasion provides design consultancy (most of it actually pretty decent) to various game devs, but the main thing anyone knows him for is "Jim Sterling's podcast co-host". Yet, interestingly enough, he is also the one person who is setting up a fallback plan if Jim's popularity flags enough that it can no longer help support him. If Conrad started to make the correct connections and contacts, and put in the effort, he absolutely could make a decent enough amount of money selling his button design in retail, as well as get them licensed out to be put on t-shirts and find moderate success and income.