We talked about this in DMs, but I figured it was worth sharing here too in case it helps others. Here’s my take: It really depends on what you want to build and why. For example, the group I’m creating will stay free, because it’s not about monetization — it’s more about connection, support, mentorship, and helping each other grow faster by sharing the process in real time. The focus is more on depth and synergy than scale or conversion. Option 1 feels like the long game. You keep showing up, delivering value, and over time you’ll naturally attract people who want more — and are ready to pay for it. That way, the free group stays alive and becomes the ecosystem that feeds your paid offers without pressure. Option 2 is riskier. You might get quick wins financially, but there’s a chance you alienate or lose some of the people who helped shape the space. Some will understand the shift, but for others it might feel like a paywall appearing overnight — especially if they’re not in a place to invest yet. That said, I have seen a few posts and comments from people who transitioned from free to paid, and the timing often seems to happen around the 100-member mark. But I’m still pretty new to Skool myself, so I’ve only seen a small sample and don’t want to generalize too much. Personally, I lean toward Option 1 — keep nurturing the free space, and let the paid layer emerge as a natural next step for the ones who resonate deeply and want to go further.