Webvan saw the future of grocery shopping with perfect clarity, promising 30-minute delivery windows decades before it became routine, and still became one of the largest dot-com flops in history. It burned through more than $800 million in three years, built a $4.8 billion empire, and collapsed into bankruptcy. This episode unpacks the paradox of the right idea executed at exactly the wrong time.

We trace founder Louis Borders' ambitious vision in a 1996 world of dial-up internet, the venture-capital frenzy that poured in nearly $400 million, and the fatal obsession with first-mover advantage. We examine the billion-dollar Bechtel infrastructure order, the leadership with zero grocery experience, CEO George Shaheen's legendary lifetime contract, and the brutal economics that doomed the model.

• Why the rush to 26 cities came befor ...