During the first three to four years, Weebly focused on convincing people that building a website was possible, as many assumed it was beyond their capabilities.

I wrote the first line of code for Weebly in February 2006, and over the next 12 years, we grew to 50 million users and around 350 employees before selling to Square for $365 million.

Weebly is an easy way for entrepreneurs to build a website or an online store, which was revolutionary compared to the previous requirement of learning to code.

In hindsight, we shouldn't have launched with a free service in the first place; we ended up becoming a truly premium model based on ticket prices. We won't monetize a free product, which allows us to undercut our competitors and led to thousands of free events being published on our platform.

Many founders think they need to offer their product for free to gain users, but it's often better to charge a price to gauge real interest.

Founders often prioritize getting feedback over generating revenue, leading them to avoid charging for their product.

We decided to offer our product as a fully functional free beta for 30 days, with a commercial price of $299 for companies and $99 for hobbyists, trusting users to pay based on their usage.

If you're going to charge for a product, it needs to be self-serve and frictionless for users. Many startups fail because they rely too heavily on founder involvement for customer acquisition.

Most startups are significantly undercharging for their products, often due to misconceptions that they should not charge or should charge very little.