[npalli]

Smugmug -- started 2002

Freshbooks -- started 2004

37Signals -- started 1999, basecamp in 2004

FogBugz -- started 2000

Point being, these are "old" business. If you are starting something today with all the hundreds of thousands of free apps and freemium based models, the same lessons would not apply.

[ProblemFactory]

All of these are also apps for businesses, not casual entertainment for consumers. Also, they are mainly delivered via web, not Apple or Google app stores, which makes it possible to offer a time-limited free trial with no free plan.

I'd hypothesise that both of these are more important factors than being started in 2003 vs 2013.

For a freelancer, $100/month is a good deal if it allows you to get a few more billable hours per month. For a larger established business, $500/month is pocket change that nobody will even notice (and the customer who signs up isn't even spending their own money).

[peterjancelis]

Google Apps marketplace allows for free trials.