Rachleff co-founded Benchmark Capital, a venture capital firm, in 1995. The firm invested in companies including eBay, OpenTable, Snapchat, Twitter and Uber. Rachleff personally led investments in Blue Coat Systems, Equinix and Juniper Networks.

In 2008 Rachleff co-founded Wealthfront, an automated investment service, with Dan Carroll. As of March 2018, Wealthfront had more than $10 billion of assets under management.

Today we talk with Andy about finding product-market fit (a term he coined 15 years ago) and the three years before Wealthfront found it. 

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