Established industries often operate like cartels with unwritten rules, such as avoiding aggressive marketing. New entrants gain a significant edge by deliberately violating these norms, forcing incumbents to react to a game they don't want to play. This creates differentiation beyond the core product or service.

Prepared realized it couldn't win against GovTech incumbents on their terms of sales relationships and lobbying. Their strategy was to fundamentally shift the competition. By offering a free, easy-to-use product, they forced the purchasing decision to be about technology quality, an arena where they could excel.

Large incumbents struggle to serve newly-formed startups because these customers offer low initial revenue but require significant sales and support. This P&L constraint creates a protected 'greenfield' market for new vendors to capture customers early and grow with them.

When Amazon attacked Square with a cheaper clone, they failed because they only copied surface-level features. Square had built a deep, interconnected "stack" of 14 non-obvious innovations out of necessity, creating a powerful, invisible moat that Amazon couldn't replicate.

Rather than engaging in destructive price wars, Visa and Mastercard prioritize maintaining high industry margins. Their primary competitive focus is on converting the world's $11 trillion in cash and check transactions to digital, effectively expanding the entire market for both players instead of fighting over existing share.

When competing against a resourceful incumbent, a startup's key advantage is speed. Bizzabo outmaneuvered its rival during the pandemic by launching a virtual solution in weeks, not months. This agility allows challenger brands to seize market shifts that larger players are too slow to address.

Square views its role as taking complex technology, from financial tools to AI, that is usually only accessible to large corporations and making it simple and available to small businesses. The ultimate goal is to improve their survival rate and help revitalize local economies.

The narrative of startups "destroying" incumbents is often wrong. As shown by MongoDB coexisting with Oracle and HubSpot with Salesforce, disruptive companies can create massive value by expanding the total market, allowing both new and old players to grow simultaneously.

Great product design removes upfront friction. Instead of complex approval processes, Square approved merchants instantly and managed risk per-transaction. Similarly, Google's Sergey Brin killed AdSense's publisher approval system, opting to review sites only after they hit a certain impression threshold, enabling frictionless scale.