How a Hot $100 Million Design Startup Collapsed Overnight

Beyond amassing megabucks, the Webvan entrepreneurs seemed to do everything right. Backed by experienced venture-capital investors, the company raced to build vast automated warehouses and bought fleets of delivery trucks while building an easy-to-use website. Webvan hired a seasoned CEO from the consulting industry. What’s more, most initial custo

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Companies with poor unit economics found themselves propelled by aggressive venture dollars (which themselves were propelled by a low-interest-rate environment). Those companies then turned those dollars into aggressive customer acquisition. Until recently, the market rewarded growth at all costs.

you’d be surprised how often founders ignore profitability (read: sustainability) and focus on product development, growing, hiring, and all kinds of other things, right up until the money runs out.

This was an incredibly difficult stretch. Every time something popped up on my calendar I knew it was someone telling me they were leaving the company. These conversations were crushing. All I could think about was finding a way to fix things. We kicked off some really cool product experimentation but we were a Series C company trying to do seed st... See more

Sam had handed Ryan his checkbook and told him to buy office space and as much worker housing as fast as possible without worrying about the cost. No man was ever so good at not worrying about the cost as Ryan. In a matter of weeks, he had snapped up between $250 and $300 million in real estate, including $153 million worth of condos in an expensiv

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