Going from 100 to 1000 users feels like trying to scale a house party into a music festival while the party's still happening. When we hit around 100 users, i thought we had it figured out - people were finding us, using the app, sending feedback. Then growth started picking up and everything that worked just... didn't anymore. The biggest pain was how our support system completely fell apart. At 100 users, i was personally replying to every email, jumping on calls, really getting to know what people needed. That personal touch was actually our secret weapon - users loved that they could message me directly and get help right away. But somewhere around 300-400 users, my inbox became this monster. I'd wake up to dozens of messages, spend half my day just trying to keep up, and still felt like i was letting people down. Had to finally accept that my "just email me" approach wasn't sustainable. What really caught me off guard was how different the user base became. Those first 100 were mostly people from my network or who found us through word of mouth - they got what we were trying to do, forgave the rough edges. But as we grew, new users started showing up who had totally different expectations. Got a bunch of support tickets asking for features that made zero sense for what our product was built for. Like people wanting us to add project management features when we're literally just a monitoring tool. Had to get way better at explaining what we actually do vs what people assume we do. The infrastructure stuff was predictable but still painful. Our database that handled 100 users fine started choking around 600. Not in dramatic ways - just these annoying slowdowns during peak hours that made the app feel sluggish. Spent a whole weekend migrating to a beefier setup while trying not to break anything for existing users. The tough part is realizing that at 1000 users, you're still tiny in the grand scheme but big enough that every technical decision actually matters. Can't just cowboy deploy stuff anymore when hundreds of people are actively using your app.