This is why I am very skeptical of (non-open-source) software made by startups. Often they are not in it to build a sustainable long-term business, but just for an exit, and that almost inevitably means the death of the software. It's as though the software is really just a sort of "corporate resumé" made to support their goal of getting bought out, not really something to be used.
Unfortunately, I realize this attitude might make it harder to actually make a sustainable business around solving a non-trivial problem, but as a user I've been burned too many times by companies suddenly getting acquired and then ceasing to exist.
This has nothing to do with opensource. Many opensource startups have just died and not taken things forward.
If anything, look into the mission of the company and how they make money. i.e. look into their business. If it's all doled out for free, it's a good idea to give them a miss.
It's sad when we pay $5 for a coffee made in 5 minutes that we'll drink in 3... but not $5 for an app that took 5 months that we'd use daily for a year.
Most coffee cups already do have ads on them. They have you paying $5 for coffee, AND running around with free ads for them in your hands. And you don't even notice you're a walking billboard for them! Not to mention all that juicy data you're giving them with every CC purchase, or loyalty card swipe...
Not to mention that $5 might be the most expensive app someone buys, and then they expect updates for the foreseeable future despite on-going development costing loads more time. There have been developers who released a separate, paid sequel and were left with angry customers who expected updates to their original app.
My experience has been that since underlying platform software changes so quickly locally run purchases are often more work to maintain than SAAS offerings.
I honestly don't think that Free software can keep up in the short term without a regular dues-paying membership organization behind it. Instead of concentrating on trying to expand interest in software rights, I think the only way forward is to consolidate the already converted. Also, it gives non-developers and non-technical people the ability to feel fully involved.
I wish the Chicago FSF had two or three offices in town, a local administration, weekly meetings, classes daily, and that I could send them $25 a month to remain in good standing.
In the long term Free software can't help but win, unless Stallman gets hit by a bus. Stallman will eventually be hit by a bus.
edit: and by all that I mean that Free Software needs to build a proper business.
In the ancient times GNU and the free BSD programs provided a vastly better user experience than the native tools in just about every commercial Unix system.
Also the window managers were at least slightly less awkward to use and at least tweekable.
I think there are a lot of specialised software development tools and products that are free or open source that are generally better than their commercial alternatives.
Although it's complicated as a lot of large players are putting a lot of money into free or open alternatives while still convincing their customers to pay a lot of money for their enterprise alternatives. (I wonder how they do it. I am actually reluctant to use a free database server although it's not uncommon for the commercial database we use to have rather horrid bugs that won't even be fixed since its virtually impossible to reproduce the problem in another system, and we can't debug properly without the source.)
It's only mass market applications and games that gives you enough money to totally outcompete free, maybe a small reason is that typically only a small fraction of the audience can code. I guess the same is true to some extent also for specialised tools in other domains, like financial or medical software, were the users typically can't code and there might be legislation and regulations too.
Its a valid question, clearly they weren't making enough money to survive as a proper business. Would you have paid more for their service? And if so enough more that the reduction in users covered the cost of operations?
One of the things that that comes up a lot with new ventures is that they don't know the answer to those questions when they start, but they do when they either die or succeed. In this case it seems that its financially feasible as a "feature" of Outlook rather than a standalone business.
Looking at the landscape of startup "businesses" recently it is becoming more clear that the viability of the product is irrelevant, since the goal is to get noticed as good programmers/designers who made a "real" thing and get hired.
You have to be careful slipping into cynicism, I try to guard against it myself. Shipping something is a better indicator of execution than a degree and it does get people noticed, but it would be an overreach I think to suggest that the majority of businesses start out looking to be bought and acqui-hired. Sometimes the idea is bigger than that, and sometimes it isn't.
I'm intimately familiar with the space, especially when it comes to Silicon Valley startups, and it's no cynicism, but reality that most of them do, in fact, start out looking to be bought. In fact, that's the #1 goal of VCs, angel investors & almost all founders.
You're responding to someone also intimately familiar with the space. Honestly, arguing whether something is a majority view vs a big minority isn't that interesting.
"Our product is our stock" - quote from HBO's "Silicon Valley"
Basically, this. Start-ups and their investors are looking to cash out. Imagine if Apple or Microsoft had been bought out by IBM in their early years, instead of them both disrupting the space drastically.
For the record, from a Microsoft stand-point, I think this makes perfect sense. They were acquiring talent and a user base it's foolish to have two competing products in your portfolio. From a user standpoint, it probably sucks (I've never used Sunrise, and actually already use Outlook's calendar.)
I'm definitely an oddball, but I would rather want to be part of a business to serve people and solve problems. I don't want to be rich, just make enough be comfortable enough to work on the problems that I want to solve.
Maybe getting bought out on my first successful product affords me the freedom to do so.
Unfortunately, I realize this attitude might make it harder to actually make a sustainable business around solving a non-trivial problem, but as a user I've been burned too many times by companies suddenly getting acquired and then ceasing to exist.