I hypothetically have a hypothetical company where I have devoted hypothetical userbase but minimal revenue streams (only donations).

Let's say the prime hypothetical userbase of my hypothetical company are techies. Cool. What would I do for revenue? I'll go to a B-School, hire some finance & marketing dudes to hand over everything to them. Why would I do that if my userbase is full of hardcore techies? Its because I now want to print $$$ and my investors aren't techies. My investors want value to compound, not stagnant. You'd say my present hypothetical company is very valueable to its userbase. But guess what, the definition of value WILDLY changes for different people. OFC I know I'm wrong, but you think that only because you're a user, not a shareholder.

Back to my fresh hires. They'll ask me to "reorient" my company "alignment" to a more "value enhancing" direction. But I'll tell them, look my userbase is all techies who want no fluff, simple to the point service. They'll leave the moment I mess with the service. The new hires ask me to reconsider if I'm actually correct or not.

What do we do? Let's start slipping in minor inconveniences, democratically. My company has a public blog and forum where my userbase regularly interacts with company employees. I go to that forum and make an announcement - "WE'RE GONNA HAVE ADS!".

Backlash? My post gets downvoted and ratioed and what not. Conclusion? I go with my decision anyway, citing "financial sustainability" fluff (as instructed by my new hires)

Some users on personal whatsapp groups discuss my tragic decision, questioning my lack of financial knowledge - "ADS? That serves no revenue dude! Everyone is using uBlock and even without that, CTR is so less." Over at my company's public forum, users are complaining, only to be shut up by a minority group saying "Just install an adblocker if you don't want to support the service you use day in and out."

A month later, the dust has settled. Now we have ads. Those flashy, moving animated kind of distracting ads. So this time, the head of UX goes to the forum and makes a post: "WE HAVE DECIDED TO BRING NATIVE ADS". What are native ads you ask? These are ads which don't look like obnoxious islands of bright gatorade and instead blend in with the site UI. These looks just like any other blog post link or user profile link, maybe with an added faded icon to signify they're an ad.

The UX Lead gets downvoted to hell before Christmas. Users now cite a breach of trust they invested in my company's service. But hey, some users post a fancy looking regex, which if pasted in uBlock's custom script, can block the native ads. Sweet.

During Christmas holidays, out on a team party, my drunk finance guy tells me that the Financial year is closing and we need to diversify our income streams for a good year end report. "Its not just the reports, its investor confidence"

But I tell him, I'm afraid we'll lose all users. We've already created a rift by introducing ads - nobody is liking it. The finance dude looks in my eyes and says, "Oh so ads are the problem. Let's get rid of them."

First Sunday of January, I go on the forum and make an announcement - "WE HEARD YOU - INTRODUCING A SUSTAINABLE AND LESS INTRUSIVE BUSINESS MODEL". Users are curious; they read my announcement, only to realize I've just added a paid tier that removes ads. I get downvoted, but not as bad as my first announcement - herd behaviour doesn't work since we removed the dislike counter on our forum.

This time, many users are coming forward to say that I should've gone this route from the beginning. After all, they've been using my crazy good service for free all there years and now with a $200K CTC, they can surely pay $5/mo to keep my company running!

I forward this message to my finance guy, questioning his decision for not introducing the paid tiers from day 1. He's smug, doesn't want to answer my direct question. Instead, he simply tells me - "your users aren't as flexble to move away as you initially thought"

We got a good number of signups on my "paid tier". They slowly stagnant - which is when we go and make an announcement - "INTRODUCING CUSTOM THEMES! DECORATE YOUR PROFILE AND CUSTOMIZE SITE EXPERIENCE". Users are happy for three seconds, before realizing its only for paid users. They're not happy, but many are justifying it saying "none of the functional aspects are paywalled; you can enjoy the service for free".

I ask my finance bro - whats the point of these paid services if they don't add any functional value? Why are we wasting our developer time making profile themes? The finance bro isn't amused, and says, "cool, let's then build something functional".

And so, we drop the summer announcement - "INTRODUCING DMs, HIGHER UPLOAD QUOTAS, ANONYMOUS VIEWING AND MORE ON OUR PAID TIERS!"

You can still use the site with "generous" free limits. But you should upgrade to a paid tier to get higher limits and more importantly, support the service you love! We plaster banners pushing you to upgrade, on various locations across my site and app UI. Anytime you upload a file, you're prompted to upgrade to upload files larger than 100kb. Anytime you view someone's profile, you're prompted to upgrade in order to anonymously view it. Anytime you send someone a friend invite, you're prompted to upgrade in order to DM them.

And yet, everything you could do an year back on my site, you can do today too.

Revenues aren't great yet. But the continous introduction of new features and a signalling that my company is willing to reorient itself in this new age has attracted other businesses to have deals with us. The finance dudes now press me to start looking for funding. And so I kick in. We secure a sizeable funding to expand our operations. Our product teams have told us that we need to use these funds for rapid scaling and user acquisition, because competitors have already started mushrooming in the market.

We realize that such an expansion cannot happen from our rented office. We decide to start outsourcing peripheral work and focus on augmenting our core services. The searchbar on my site is now integrated with a major LLM provider. User feeds are personally curated thanks to a data broker who signed a data sharing deal with us last month. Since we have techies as users, a job portal has partnered to integrate their services in my app. A third party analytics platform provides user retention and engagement inputs. On the next christmas, we shut down our public meta forum because we signed contract with a customer support startup which agreed to provide excellent user feedback systems via a web portal. Another AI startup has claimed they train LLM on my user generated data and create smart solutions to help new users.

Developments become difficult to keep track of. The expansion was really rapid. I take a vacation to spend time in Hawai (its my first international trip!). I offer free vacation to those few initial hires who helped me come this far in the journey.

On the way to airport, while checking in on my flight web portal, I'm greeted with a useless AI chatbot who doesn't understand that I need to check in. It was irritating; and so, I ask one of the other guy in the cab - "isn't this useless chatbot the same service we have integrated in our own company products?" The guy nods his head, with a faint "hmm".

I'm not happy with the casual response. I ask him why are we burning cash on a chatbot which does NOT work? How are we serving our users? WON'T THEY MIGRATE OUT???

To which, he calmly replies, "are you cancelling your Hawai trip because the check in process is convoluted?"

"but...."

"You're still flying. And so are our users. The chatbot isn't to help our users; its only to see what level of enshittification they are ready to bear."

I think I got the point, but anyway, I told him, thats not the direction I want my company to take.

"Whats the use of talking this after booking a trip on investor money? You should've told this when we introduced ads to check how much our users can tolerate."