17: Andy Rachleff, Co-Founder Benchmark Capital and CEO of Wealthfront

“Product-market” fit is one of the most ubiquitous and foundational terms in the startup community today. It’s a term that has inspired blog posts, books, curriculums, conferences and even plot lines of TV shows (turns out, its just as hard to find product-market fit in TV land). It’s virtually impossible to talk about products today without hearing reference to product-market fit; there are 400,000+ unique results on Google and over 5,000+ videos on YouTube explaining the concept.  It was a thrill to speak with the legendary executive and investor who coined the term, Andy Rachleff. Andy co-founded Benchmark Capital and led the single best performing early stage fund of all time. Benchmark has invested in an absolutely dynamite list of startups over the last 20 years: eBay, Uber, Twitter, Snapchat, Dropbox, Instagram, WeWork, StitchFix, Yelp, Zendesk, and Zillow amongst others. Over the past decade, Andy switched back to the operating side and founded Wealthfront. Today Wealthfront is the leading automated investment service in the market with over $10 billion in assets under management. We had a lot of fun in this one. This conversation was highly focused on Andy’s foundational work in product market fit, disruptive innovation and how these concepts serve as guiding principles in his work today with Wealthfront. The podcast is filled with great lessons, but a few highlights included: (1) why you can screw up everything if you have product market fit and still likely succeed, (2) how the best companies are founded with insight to a key inflection point in technology, (3) why the combination of being correct and contrarian drives the highest potential for value creation and (4) why failure is overrated.