What's the biggest RISK you have taken for your product and how did it pay off?

The biggest gamble I have made with my product was switching from a paid membership service to a freemium one. This choice was difficult since it forced us to reevaluate our whole approach to generating income. In the end, though, it was well worth it because we were able to expand our user base, delight our existing customers, and boost our conversion rates. Our company's income and reputation both skyrocketed once we took a chance.