I've been looking into myself recently. From successful bootstrappers in B2B, nearly 100% of the advice that I've gotten is to start without free and add it la

I've been looking into myself recently. From successful bootstrappers in B2B, nearly 100% of the advice that I've gotten is to start without free and add it later as a lead-gen mechanism if it fits your business. Early on customer acquisition is a slog and generally relies on 1:1 conversations often with a pre-existing relationship (in-network). Hopefully feedback from these people help you get close enough to product market fit that outsiders will consider using the product. From there it's a marketing and lead nurturing game where freemium may make sense. Advice for B2C would be quite different.