Timing is definitely tricky. I believe most of the first wave of Nostr startups will just remake slightly cooler old-world experiences. The really big winners will likely emerge in the next wave with brand new experiences that mash up nostr + lightning. I don't know what these will be, but they'll be cool as shit! One simple example: I can imagine most people sending payments or remittances via a text/tweet and not in a dedicated app.

So given that perspective, I'd rather bet on the second wave. But Nostr development is happening ridiculously fast. B/c it's open, simple, and fun. Hell, I may start programming again to join in on the fun :) So given how fast it's all being built, I could also see a world where that 2nd wave comes very quickly. So given my intuition on all this, I'd much rather be there early.

And for the most part, I'll follow the same guidelines I do for investing in Lightning companies: back really smart founders with great taste who ship quickly. We'll figure everything else out on the fly ;)