Lyft, the Perpetual No. 2, Gets Its Moment in the Spotlight

Half a decade ago, Travis Kalanick invited John Zimmer, a founder of Lyft Inc., to his apartment in San Francisco. Kalanick, the then chief executive officer of Uber Technologies Inc., said he wanted to buy Lyft. He told Zimmer and a Lyft investor that the combined business would be more valuable than either company on its own.

Lyft’s asking price at the time would have amounted to less than $3 billion in equity, but the executives couldn’t come to an agreement. It wasn’t the only time Uber could have made a deal with the most fervent competitor on its home turf. But now that Lyft is set to hold an initial public offering on Thursday that would place a value of at least $24 billion on the business, some Uber insiders are taking a moment to privately reflect on their missed opportunities.