So much of the value was already delivered in that simple `git push heroku master` which gave you a container + load balancer + a database. The vast majority of people didn’t need more. And of those that were left that did far too few of them were willing to suddenly start paying $32/mo per dyno (you just gave me one for free! I only want one more!) or make the jump to multiple hundreds of dollars for a database.
Read any of the threads about Heroku over the years. The biggest complaint is always “it’s too expensive”. Even when a large percentage of what was on people’s bills were add-ons like databases, new relic, redis, logging, etc (i.e., not Heroku).
I feel like that's Fly.io now. They took all of the great things about Heroku but also dramatically improved and added new capabilities...while improving on pricing, particularly for lower traffic stuff. Love Fly.
I also love Fly, but they were missing easy managed databases (which always seemed like the main reason to use Heroku to me). And now they have them they're very expensive (even compared to Heroku). Which is a shame because their compute is very cheap.
We're doing Managed Postgres now (MPG), which is what we should have done to begin with, but it took us for-ev-er to get here.
To my understanding there was a runway-growth problem. Could the founders raise and spend (efficiently) enough money quickly enough to keep the business viable? It would be a big gamble and the alternatives were to shut down (no way!) or sell. So they sold.
Rackspace wanted to take Matt’s and Jason’s know how (plus customer base) and go big, really big! That defocused our efforts a bit, plus there were corporate integration headaches (though not too bad). Eventually Linode, already a competitor, and later Digital Ocean filled the void.
I remember being excited by the merger because well, Rackspace had such a fantastic reputation at the time. People still tell stories about their service. The Rackspace Cloud was just up against an absolute monster in AWS and never really became competitive.
This is a common misconception, but it's actually not true. The reality is even more bizarre.
Most of Heroku's successful years came after the acquisition, not before. Heroku was acquired extremely early in its lifecycle, and Salesforce does actually bear responsibility for investing in it and making it the powerhouse it became. Most of what people remember as the glory days of Heroku came long after the acquisition. And in fact, at the time of acquisiton, Heroku was nowhere near as competitive as a product as it later became.
It was only much later on that Salesforce began to pull the supports out from underneath it, leaving it to fall behind and become what it is today.
The narrative of "BigCo™ acquires startup, then leaves it to wither and die" is a trope because it is very commonly true, but it's actually not what happened in this particular case.