Linden Tibbets

In 2010 I covered a wall with sticky notes. Some sketched the database: users, triggers, actions. Others sketched what it might feel like: a triangle for "if," a circle for "then," and a lot of questions. Back then I called each automation a "statement." Today they're Applets. That wall turned into a side project I called "ifttt," and I've been working on it ever since.

I am planning out my next project for a hackathon. As I previously completed two vastly different types of products, DukaanMate and LeetSeek, I want to focus on being more thoughtful with validating the next idea as opposed to just beginning coding.
Instead of asking individuals for new features, I think I will ask them to tell me the most recent time they had to accomplish a task that caused frustration, and then use those responses as inspiration.
To all Makers that have created and sold a SaaS product: What drove your conclusion that this is a "real" issue? Were you able to see the same work-around over and over again from users? Or were there some users that expressed their willingness to pay for a solution? If either of these are examples that fit your experience, please provide a specific example of how you validated the problem and what you learned.