When do you actually start asking for the sale?

I’m looking for some real strategy insight from those of you who’ve built communities before.

I recently created two separate communities, one free and one paid. My intention is to genuinely help people, build trust, and avoid rushing into selling too quickly. At the same time, I know that if I never make an offer, I’m not truly serving the people who are ready to take the next step.

So I’m curious how you approach this in the early stages.

When do you personally begin selling? Is it week one, week two, or after a certain level of engagement and value has been delivered?

How do you structure the first couple of weeks so it feels aligned and not forced? Do you focus purely on value at first, lightly introduce the paid offer early on, or clearly communicate the path from free to paid from day one?

And what’s worked best for you when it comes time to sell? Do you prefer DMs, community posts, or a combination of both?

My goal is to do this the right way, where selling feels natural, helpful, and in service to the community rather than salesy. I’d love to hear what’s worked for you and what you’d do differently if you were starting over today.

Appreciate the insight.

2 comments