…and who managed the sourcing and managing of relationships with these 3rd parties. If there’s any serious volume of it then its yet more work. Having seen this many times it always ends up being more work than anyone expected at the outset…
Is there really much of a market for those things though? Honestly if I saw anybody using TR-branded apparel, coffee cup, etc I’d assume they’d been given it at a trade show or had an affiliation with the company or something, not paid for it. Funnily enough saw somebody the other day in a cycling jersey with a Zwift logo on and it stuck in my head because I can’t recall ever seeing anybody wearing Zwift branded kit. And I live in an area with a LOT of cyclists (Strava segment leaderboards round here often have 50-100,000 people on) and Zwift has a lot more users than TR I think.
I would see that stuff being quite low revenue/margin, and a lot of work to set up correctly. As the TR team seem (rightly) pretty obsessed with quality so wouldn’t want their logo going on any product they haven’t personally used and are happy to endorse, and if they get it wrong (e.g. kit that doesn’t fit in line with the size guide) then they’re going to have a load of noise on the forum and elsewhere.
This is the one I bought back in 2020, but it looks like it isn’t currently available.
I could be totally wrong, but it’s hard for me to believe almost every TR user wouldn’t buy a tshirt or a coffee cup or a trucker hat. Those things are simple. You just put the company logo on the existing product. These things already exist, they just don’t sell them.
Ride a specialized bike? You buy these things.
Drive a Jeep? You buy these things.
Have a favorite artist? You buy these things.
I don’t see why TR would be any different.
Swag is much more expensive than most assume, particularly for software companies because they aren’t in the business of managing inventory, selling hard goods, logistics, and supporting those products.
Even if you have a third party that handles ordering, inventory, and logistics, you end up having to support those products after they are sold, and it can be a profound drain on resources. Speaking to other companies in our space, I have yet to see a brand have this turn out profitable for them.
Isn’t there profit in the conversations generated by people who see the swag and go on to join the family?
branded merch is really a great advertisement. its worth more than the profit of the goods. How many times have you seen a brand on a kit that you dont know about and looked it up? In the case for TR, you didnt just make $4 on the shirt, you made a $19/month subscription. Theres plenty of companies that can handle this for you. You provide artwork for the merch, they stock it, ship it, deal with it and cut you your %. I agree that doing it in house is a nightmare, but contracting it out is only a trivial amount of work. Not my company to make the call, but just like the podcast is an advert, merch does just as well!
The funniest thing I ever heard was from the kids who said “Why do you have a watch? You have the time on your phone in your pocket.” and then later (with zero irony) said “Oooh, look, Apple invented a timepiece you can wear on your wrist. Finally I don’t have to reach into my pocket for my iPocketWatch.”
Think you’re massively overestimating the conversion rate there 
To start with, only a small % of TR users are going to buy TR swag. You’d need to be a pretty big fanboy to start buying clothes for an indoor cycling platform.
Of the few that see TR branding on a t-shirt/cap and decide to look it up… they’d check what it does and the price, then compare it to Zwift, Wahoo X etc… only a small % are going to actually subscribe. So you’re talking a small % of a small %, which is why it isn’t going to be profitable.
Probably overestimating 
But that is how marketing works… you spend money to hopefully make money. You’re right about zwift, but I know tons of people that either use both or have gotten tired of zwift and want something new. Word of mouth seems to be doing just fine for TR now, but RIM (blackberry) also said the same thing in 07/08 
this only works when you have access to the general population or a very good chunk of it. when you deal with sub-cultures in marketing its a whole different ball game. brand awareness of training platforms within cycling circles is pretty high. casual use case for trainer road is pretty low to zero, as opposed to nordic tracks/pelotons of the world. spending money for awareness would be the absolute last thing I would spend money on as a CEO.
The AACC pod is new marketing for a modern age. Where I would spend marketing dollars is on YouTube content creation to push out the boundaries of who TR appeals to. “how using TR helped me get to 7% body fat and win my body building competition”…“Peter Attiah tests biomarkers of septuagenarians using the polarized plan to see if z2 is teh key to longevity” etc.
Best case is a fan does an advanced purchase of shirts/kit/etc. based on pre-orders with the kind permission (and blessed art work) of the folks at Trainer Road.
I tend to be on the “you should have a basic merch program”-camp. I’m not talking kits at all (cyclist and tri-peeps are way to picky). Just a trucker hat, t-shirt and maybe a coffee mug. I saw first hand how a merch program can get out of hand but just having that awareness can go a long way.
I was at powerbar and it indeed get outta-hand with inventory and we even had DS, warehousing, customer service and other things to handle it but it still got so big and unmanageable that it came to a bad abrupt halt.
Having a 3rd party manage it is well, manageable, slightly profitable and really if it is not should be considered a marketing expense. If i was at a regi line at a race and the guy/girl in front of me had a TR t-shirt i would strike up a convo. thus building the community. It may be preaching to the choir moment but its still branding.