@amycatling it sounds like you did a fantastic job promoting the contest and engaging your members. I don't think you pushed too hard, especially if these people have expressed interest already. If it's something I'm interested in, I appreciate reminders. As an anecdote, I've received two emails a week from organizations and communities I participate in, providing updates and ways to participate.
When you ask for participation from non-members and new members, make sure you start with really low-effort activities. Also give people many ways to get that "feel good" moment of winning. I try to design in terms of motivation and perceived ability. In the case of contests specifically, the higher the perceived LOE and likelihood of competitive entries, the less motivated / capable of winning someone feels.
Check out Derek Sivers' TED Talk: https://www.ted.com/talks/derek_sivers_how_to_start_a_movement
You're doing the community dance, and it's time to encourage your first followers. It doesn't take many for more people to catch on. I totally get that you don't want to feel like you have to start every discussion topic where everyone just responds to you. It's like when you're introducing two friends that you know, but who don't know each other. Until they get to know each other a bit, they're likely going to lean on you to come up with conversation topics you know they share interest in. I can already see evidence of your success in doing this in your community chat thread. And if you see someone stepping up and taking the lead, encourage it! A community of entrepreneurs has to have some natural leaders among them 😉
For the members who you did get engaged, build some relationship capital by really taking an interest in them and their entrepreneurial initiatives. Write down what they share about themselves in a place where you can remember later - such as their profile Admin notes. If people feel like you are invested in them, they're more likely to reciprocate, and you'll be in a great position to ask them what else they'd like to see/do in the community, and to ask for more effort on their part.
LSI is also a super useful tool to identify topics that are interesting to your members. A great way to encourage budding leaders is to feature their discussions. Use your features to "nudge" other members into discussions by making them super easy to find.
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