Office Hours Podcast: Online Retailer Behold Uses AI To Craft Bespoke Outfits

Spencer Rascoff

Spencer Rascoff serves as executive chairman of dot.LA. He is an entrepreneur and company leader who co-founded Zillow, Hotwire, dot.LA, Pacaso and Supernova, and who served as Zillow's CEO for a decade. During Spencer's time as CEO, Zillow won dozens of "best places to work" awards as it grew to over 4,500 employees, $3 billion in revenue, and $10 billion in market capitalization. Prior to Zillow, Spencer co-founded and was VP Corporate Development of Hotwire, which was sold to Expedia for $685 million in 2003. Through his startup studio and venture capital firm, 75 & Sunny, Spencer is an active angel investor in over 100 companies and is incubating several more.

Office Hours Podcast: Online Retailer Behold Uses AI To Craft Bespoke Outfits

Terry Boyle, co-founder and CEO of Behold, says his newly launched retail platform aims to solve a major pain point for online fashion consumers: Having too many options.

When on-boarding to the site, customers take a few minutes to plug in their fashion likes and dislikes, as well as their body type and sizes. Guided by machine learning, Behold's customers receive personalized outfits and streamlined choices, based on their shared preferences.


For example, if a search is plugged in for black shoes, Boyle says, "we don't bring you back seven thousand five hundred black shoes...we bring you back 20. And then we see...what you think and how you react, and then we bring you back more."

Hear how Boyle, who's been in fashion tech for over 10 years — most of them spent at the venerable Nordstroms — is competitively positioning and running his trailblazing company, in which I'm a small, personal investor.

Want more? Subscribe to Office Hours on Stitcher, Apple Podcasts, Spotify, iHeart Radio or wherever you get your podcasts.

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