Once the very embodiment of Silicon Valley venture capital, the storied firm has suffered a two-decade losing streak. It missed the era’s hottest companies, took a disastrous detour into renewable energy, and failed to groom its next-generation leadership. Can it ever regain the old Kleiner magic?

SOME FIVE YEARS AGO Vladimir Tenev and Baiju Bhatt, founders of a potentially disruptive no-fee stock brokerage startup called Robinhood, set out to raise capital for their fledgling Silicon Valley outfit. They sought a relatively small amount, $13 million, that would value their idea at $61 million. The former Stanford classmates, both within spitting distance of their 30th birthdays at the time, did what entrepreneurs have been doing for decades: They asked the venerable venture capital firm Kleiner Perkins Caufield & Byers to back them.

Kleiner—its singular name is as sufficient on Sand Hill Road as Oprah is in Hollywood—was interested. The firm sees lots of opportunities, however, and it chose not to bite. Then, in mid-2015, when Robinhood was looking for another $50 million at a valuation of $250 million, Kleiner passed again. By 2017, when Robinhood became a “unicorn” valued at $1.3 billion as it raised an additional $110 million, it was the startup doing the snubbing: It excluded Kleiner from the list of venture firms that participated in its funding.

It wasn’t until early last year that Robinhood and Kleiner finally connected, according to accounts from dealmakers on both sides. By then Robinhood had made such a splash in the brokerage world that Fidelity, TD Ameritrade, and Charles Schwab had cut fees in response to the upstart’s zero-commission offering. Under the sponsorship of famed Wall Street analyst Mary Meeker, a Kleiner partner since 2011, the firm that had failed repeatedly to invest at increasing levels now participated in the $363 million funding round, valuing Robinhood at $5.6 billion.

The inability to get in on a hot startup’s ground floor, only to subsequently pay a far richer price, was all too common for the once-storied firm. Kleiner had sat out on another generation of technology investments, the crop of so-called Web 2.0 companies, including Facebook in the 2000s. Now, in the 2010s, it was failing again to make early-stage investments—the traditional meat of venture capital investing—in the most sought-after startups of the day. But this time its whiffs came with a perverse twist: Kleiner was succeeding wildly with a new strategy centered around Meeker, who ran a separate fund within the firm focused on more mature private companies that required capital to grow as opposed to merely establish themselves.

“Growth” investing, with its more developed companies, should be somewhat safer than

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