The Idea: It was 2004, and Matt Maloney was starving. Working late nights as a software developer at Apartments.com in Chicago, he was sick of the same old routine: dig through a pile of crumpled takeout menus, call the restaurant, read out his order, fumble for his credit card. There had to be a better way. So Matt and his coworker Mike Evans started building one. The idea was simple - a website where you could see every restaurant that delivered to your address, browse their menus, and order online. No phone calls, no paper menus. Friends told them it would never work. Restaurants were too old-school. Customers wouldn't trust it. But Matt and Mike kept building anyway, spending nights and weekends coding in their apartments. This was the beginning of GrubHub.

The Execution:

• 2004: Matt and Mike launch GrubHub in Chicago, manually collecting menus from local restaurants and uploading them to a basic website. Their first business model charged restaurants $140 for six months of "premium placement" - it flopped.
• 2006: They pivot to a 10% commission model and win first place at the University of Chicago Booth School of Business's New Venture Challenge, validating the concept and opening doors to investors.
• 2007: GrubHub raises $1.1 million in Series A funding to expand into San Francisco and New York. The race to dominate online food ordering begins.
• 2013: GrubHub merges with rival Seamless in a deal that creates the dominant player in the space. Matt becomes CEO of the combined company, which processes 130,000 orders per day and generates over $100 million in revenue.
• 2014: GrubHub goes public at $26 per share, raising nearly $200 million and valuing the company at $2.7 billion. The stock soars 31% on day one.
• 2021: Just Eat Takeaway acquires GrubHub for $7.3 billion, creating the largest food delivery company outside of China. Matt joins the board and leads North American operations before stepping down later that year.

The lesson? Matt built GrubHub by solving his own problem first. He didn't wait for perfect conditions or outside validation - he just started collecting menus and writing code. The pivot from premium listings to commission-based revenue shows that your first business model is rarely your best one. And the Seamless merger proves that sometimes your biggest competitor can become your biggest asset.