Why didn't the fundraise work? Maybe because your business model doesn't appear to be working at your current scale, you're not scaling fast enough to make it work any time soon, and you didn't seem to have any clear plan to change this.
I don't mean to be harsh, it sounds like you gave it a shot and it went pretty right. But you got caught up in the unicorn-chaser Silicon Valley mindset:
1) Do something that only works if you're huge
2) Raise lots of capital based on the idea that you will one day be huge
3) Use that capital to become huge enough that your thing actually works
Sure, planning for your startup to be a unicorn is great if it works, but "big or bust" almost always ends up in "bust".
I don't mean to be harsh, it sounds like you gave it a shot and it went pretty right. But you got caught up in the unicorn-chaser Silicon Valley mindset:
Sure, planning for your startup to be a unicorn is great if it works, but "big or bust" almost always ends up in "bust".