When intrapreneur Eric Yuan saw the need to rebuild Webex, Cisco's internal bureaucracy and layers of management prevented his idea from reaching decision-makers. This forced him to leave and start Zoom, turning a loyal employee into a major competitor.

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To speed up Ring, returning founder Jamie Siminoff bypassed traditional management layers. He elevated high-potential, more junior employees to report directly to him, not as managers, but as individual contributors running key initiatives. This broke up hierarchies and increased ownership.

Despite unprecedented demand, Eric Yuan admits that hiring over 6,000 employees in two years was a mistake that led to an unsustainable cost structure and low productivity. This resulted in painful layoffs, serving as a cautionary tale against reactive, hyper-hiring even during a massive boom.

A cultural shift towards top-down management, where engineers were no longer part of key decisions like moving to the cloud, led to a mass exodus of senior talent. When senior ICs cannot stand behind leadership's decisions, they lose the motivation to stay, even if the pay is good.

Within a large corporation, an intrapreneur's success hinges on validating their idea with potential clients. Since internal investment is a zero-sum game, demonstrating market knowledge and a clear path to customer validation is crucial for convincing leadership to fund your project over competing priorities.

Facing intense competition post-COVID, Zoom's strategy is to ensure its platform is open and integrates with competitors like Google and Microsoft. This acknowledges that enterprise customers don't want to be locked into a single vendor's suite, making openness a competitive advantage.

When Hexclad's founder suggested using Facebook for community in 2010, his boss's dismissal became the direct motivation for him to leave and start his own, more modern company, exploiting the established player's blind spot.

The founder of food distributor Cisco, John Bott, was escorted from the building after he retired. He tried to warn the board that their new consultant-driven strategy of centralized procurement was destroying the company's quality-focused ethos, a vision he had built for decades.

Beyond financial incentives or strategic differences, a primary driver for a successful partner to spin out from an established firm can be pure ego. The desire to build something independently and prove one's own success is a powerful, albeit rarely admitted, motivation for starting a new venture.

Eric Yuan didn't seek an empty market. He entered the "extremely crowded" video conferencing space after discovering that not a single user of existing tools like Skype or WebEx was truly happy. A market saturated with dissatisfied customers signals a massive opportunity for a better product.

Constant exposure to top founders and a build-centric environment at YC creates an irresistible "itch" to start a company. The organization accepts that its best employees will almost always leave to become founders themselves, not to join other tech giants.