On the flip side, I don’t think it’s pricey, $25 per user, per month for something that will make developers more efficient is well worth it. Sent to my Tech Lead to see if he wants to sign up.

For me personally, I'd pay $99-$149 flat plus paid updates if I liked it. But I know what they say about asking your potential customers what they're willing to pay ;)

For private mentoring/tutoring programming learners, $1 per session.

Perhaps it's just a value comparison thing. My company pays $5/user/mo. to GitHub for private repos, storage, and GitHub Actions. Every developer uses it every day to accomplish business critical project work. A pairing tool feels more optional to me, especially when Slack's built in screen sharing accomplishes 50% of what we need as part of another service we pay another per user per month fee for already. So a tool that's 5x the cost of GitHub that serves as an optimization for what we do is hard to justify. As a company we could afford it, it would just be a difficult sell, especially when a competitor is still free (turns out "for the duration of the pandemic" is a lot longer than they thought, oops). Of course, if we had a culture that paired on a regular basis, this might be easier, but it's more of a when you need help or want to work together thing, rather than being required.

Additionally, as others have mentioned, I think some of the issue is the lack of a free or low cost personal tier that has some set of restrictions. What those would be for an arbitrary pairing tool I don't know, but it feels really pricey if I just want it available for one-off pairings.

Now, personally, I could sign my OSS project up for a free version, but since I don't need (or want, lol) to pair with most contributors, that feels a bit wrong.

$10 for 15-20 hours of usage a month?

Automatically bumps to the $25 price if you go over.

ScreenHero, IIRC, went from free to roughly that same pricing, and crashed and burned because everyone had gotten used to free. I absolutely loved the software, but it wasn't critical to our workflow at my job at the time.

Unfortunately Teams, while terrible, is sufficiently usable that I don't see being able to persuade my current environment to adopt Tuple either.

I think, if I actually paired outside of work, I'd be willing to spend $5-$10/month just for casual non-commercial use. I'm not sure when I'd ever take advantage of such a pricing tier, sadly.

It's totally reasonable. Don't take too much pricing advice from people who aren't using it.

A limited free trial can be good. But if you make it cheaper or free now, it's way harder to go back up In Price than it is to cut price later.

We don't have a strong pairing culture, but we're trying to create one! It's a little harder to justify the price because we don't know how many people will use it yet. Besides, programmers are often not the ones who are in charge of approving expenses.

In any case, Tuple is really great. For us, I think it would become a no-brainer if it had a seat-based model. e.g., we pay for 4 pairing seats a month, and a max of 4 developer can use Tuple at any given time.