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.

The freemium model is effective when there's a clear constraint that users want to overcome, prompting them to pay for upgrades.

If I were to start HubSpot again, I would implement a freemium model to attract users more naturally before converting them to paying customers.

In the early days, we avoided free trials to ensure we received feedback only from customers who truly valued our product, which helped us stay focused on delivering real value.

We realized we needed to charge businesses a few hundred dollars a month instead of just $20-$30 to make our business model viable.

Our goal is to democratize education, and while we initially thought we could monetize through user-generated translations, we found that a freemium model was more effective for our growth.

In the early days, we set HubSpot's pricing at $250 a month, which remained unchanged for the first six years as we figured out our model.

We launched Duolingo with a premium model where users can learn for free but see ads, or pay to remove ads, which allows us to fund the platform while keeping it accessible.

Initially, we thought we were on the path to success, but I later realized that we were not converting users into paying customers because we were too focused on fundraising and PR instead of creating a product that people actually needed.