Birdies was founded as an indoor-only slipper brand. When customers began wearing them outside, founder Bianca Gates had to abandon her original vision. The company's massive growth came only after she surrendered and pivoted the product to meet this unexpected user demand.

Mailtrap was created after its founders made a catastrophic mistake: accidentally sending 20,000 test billing emails to real customers. To prevent a recurrence, they built a simple internal tool to trap test emails. This tool, born from solving an intense, personal pain point, had immediate product-market fit when shared with the developer community.

Miha Books' pivot to highly profitable school book fairs wasn't a strategic plan. It originated from a single PTA parent's suggestion while visiting their struggling brick-and-mortar store. This highlights how listening to customers can reveal a business's most lucrative opportunities.

Scribe started by building workflow automation, viewing documentation as a simple byproduct. Customers, however, found the automation only incrementally valuable but saw the documentation as a game-changing solution. Listening to this strong user pull led to the company's successful pivot.

The most valuable question a VC can ask a founder is, "Why are customers churning?" According to G2's Godard Abel, investigating what's not working provides the most critical insights for improvement. While founders naturally market successes, the real opportunity for growth and learning comes from understanding and addressing failures.

Figma's CEO Dylan Field now realizes that a user sending a 14-page feedback document after a buggy, non-performant product demo was an unmistakable sign of strong demand. Intense engagement with a flawed product indicates a deep user need that founders should act on decisively.

Major tech successes often emerge from iterating on an initial concept. Twitter evolved from the podcasting app Odeo, and Instagram from the check-in app Burbn. This shows that the act of building is a discovery process for the winning idea, which is rarely the first one.

Maintain a running list of problems you encounter. If a problem persists and you keep running into it after a year, it's a strong signal for a potential business idea. This "aging" process filters out fleeting frustrations from genuinely persistent, valuable problems.

First-time founders often over-intellectualize strategy. Decagon's founder learned from his first startup that a better approach is to talk directly to customers to discover their real problems, rather than creating a grand plan in a vacuum that fails upon market contact.