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This ex-Googler pawned her 24-karat gold jewels she inherited from her mother and sold some of her Google stock to launch her new startup

Katie Canales
LookyLoo ex google startup

Katie Canales/Business Insider


  • Chia-Lin Simmons is a seasoned veteran in Silicon Valley's tech sphere, with more than 20 years of experience at tech giants like Google and Amazon's Audible.
  • Simmons is the founder of a new startup called LookyLoo, which will launch its first product later this year: an AI-powered social platform that helps women find the right fit while shopping for clothing.
  • Simmons sold some of her Google stock and pawned the 24-karat gold jewels given to her by her mother to get her startup rolling.

Chia-Lin Simmons doesn't seem like the kind of person to launch a fashion-focused startup. "In my native form, I’m basically in a Google T-shirt and yoga pants talking to engineers," Simmons told Business Insider.

And yet, Simmons is the founder of LookyLoo, an Oakland startup that is wholly centered on fashion. LookyLoo plans to use artificial intelligence to help women identify the proper fit while shopping for clothing, which would let women consult other women on the platform throughout the shopping process. Think of it as having an unbiased opinion at your fingertips when trying something on in a dressing room. 

LookyLoo's platform is in its infancy, with the app slated to go live across the US in September, but Simmons' vision has already gotten some attention — she spoke at San Francisco Design Week in early June about AI's role in the future of retail. 

Simmons has yet to delve into funding rounds for her company, so no money has been raised yet. But to get the ball rolling on LookyLoo's early development, Simmons sold some of her Google stock — and took the 24-karat gold jewels her mother had given her to a San Francisco pawn shop.

“This is how women founders move; we don’t get the benefit of the doubt," Simmons said. 

Simmons' experience in tech spans more than 20 years. She's held executive positions at Amazon's Audible, Time Warner/AOL, and Samsung's connected car business Harman before joining Google's Play division in a global partner marketing role.

“Nobody turns down Google. They’re like the mafia," Simmons said. "They call, you’re like ‘OK.’”

She and her two male cofounders, Rafael Saavedra and another who chose not to be named, have been around the block of Silicon Valley's tech industry, a field known for being dominated by fresh-eyed and bushy-tailed 20-somethings. (Research firm Statista found the median age amongst Facebook employees to be 28.)

“We’re not 22 and just graduated; we know what it means to build technology," Simmons said.

She'll kick off funding rounds for her company soon, but in the interim, she said she's lucky to have been able to live off of her Google stock and the funds she made from her heirloom gold, a privilege unafforded to the majority of female founders in the startup territory.

"This is where most women’s businesses and startups fail, they don’t get that first vote of validation," Simmons said.

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