The goal of freemium is the upsell - "hey you liked my x, try my y!" - which requires a tight association between your products. You upsell in the same market.

The goal of freemium is the upsell - "hey you liked my x, try my y!" - which requires a tight association between your products. You upsell in the same market. You do brand differentiation in different markets. Basically, if you can imagine someone deciding to buy one product instead of another, they're in the same market. Nobody's sitting in the lot thinking "hmm, Lexus or Toyota?" but they might be thinking XLi vs GLi. That means you can convince them to get the more expensive one. Some software does do brand differentiation, though. Off the top of my head, Hiveminder and Request Tracker - one is personal, the other enterprise, both made by Best Practical. Hiveminder is actually freemium itself, and RT has support & hosting tiers.