Push yourself to go upmarket as soon as you can. Here's why.
Having spent six-plus years building the web's leading freemium e-signature service at EchoSign, I've learned one thing if nothing else: Almost everyone gets the math wrong in assuming how much revenue they can make from giving away a free product and how many users will choose to upgrade to a paying version. It's tempting to believe in the fairy tale that posting free stuff will generate waves of inbound fans who convert to paying customers at a high rate.
But 9 times out of 10, don't expect a freemium model to generate most of your revenue. Especially if you want to Go Big. There just aren't enough businesses in the First World to get to a $100 million freemium business all that often.
Let's do the math: