You know the pattern. A fast company joins a large enterprise. At first, the future looks wide open. Then the founders begin spending more time explaining than building. The product roadmap fills with special requests. Meetings multiply. Decisions travel farther. The distance between an idea and a shipped product quietly grows. No single decision looks wrong. Nearly every request is reasonable. Yet momentum fades, key people leave, and the growth engine the enterprise acquired becomes another business unit. What is actually going wrong? Oil Tanker Water Skiing provides a diagnostic for the hidden structural forces that slow acquisitions, partnerships, and internal ventures. It explains why good intentions and “hands-off” promises are not enough, how to recognize the early signs of destructive integration, and what to redesign before speed is lost. Through cases including Pixar, YouTube, Instagram, Skype, AWS, Nespresso, Lockheed’s Skunk Works, and Microsoft and OpenAI, Ben Love develops five practical principles for: The metaphor is simple. The startup is the ski boat. The enterprise is the oil tanker. The skier is the product, customer promise, or capacity for rapid adaptation that must remain on the surface. The answer is not to make the tanker the towboat. It is to design the right tethers between them. If you have watched a promising venture slow down inside a successful company, you have seen the problem this book was written to solve. Find the drag. Redesign the connection. Keep the venture moving.
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