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Hi there, I can try to answer this question from a user perspective. I was an early Winnie user in their public beta and it's one of my top two favorite startups that has launched in the last couple of years.

Initially it did feel like an empty room, but this was before the ability to start discussions with other users and ask questions. Initially you could only add reviews of places. I remember adding a couple of reviews and since I didn't get any immediate engagement from other users it felt like I was adding valuable content but it wouldn't really be useful until they got a large number of users.

When discussions became available the biggest thing was that Anne and her co-founder Sara were really active users and shared their knowledge of being parents. Every single post that I added was liked and/or commented on by them. If you asked a parenting question or posted something in the early days it would be answered/commented/liked by Anne and Sara and often within minutes. They also would add valuable and engaging content on a daily basis whether it was an interesting article, something funny, or just asking a question that could be answered by users and start a discussion. When you see how active both of them were it makes you feel like posting something or commenting is okay and at least going to be acknowledged and appreciated by them even if there weren't a whole lot of other users that were active. I always knew that in the early days the biggest thing was just continuing to add valuable content and eventually the engagement would follow. After a few weeks I started to see other users become more active and start liking my posts and adding their own which just continued to grow until they got to some of their big growth events like being featured in the app store or launching their daycare directory.