One of Poshmark's earliest investors is Navin Chaddha, managing director of Mayfield, the VC firm who has also backed Lyft, Grove Collaborative and Tonal. Chaddha describes first meeting CEO Manish Chandra in 2004 at The Indus Entrepreneurs, an organization for Indian-American tech entrepreneurs. 

"We hit it off, as we were both technologists who were fascinated by business and self-identified people-first leaders," Chaddha told Insider. He ended up advising Chandra on his first startup idea, Kaboodle, a social shopping service that was eventually sold to Hearst for over $30 million, according to Techcrunch.

Naturally, when Chandra needed a buddy to brainstorm some ideas for his second startup, he called his old friend. They met for breakfast at Hobees Restaurant in Cupertino where the idea for an app-based social shopping community was born.

"Manish had identified that the iPhone and Instagram would serve as consumer behavior accelerators for mobile and social engagement," said Chaddha, who is still on Poshmark's board. That was when the idea clicked for Poshmark to be a mobile-first marketplace with social components added in, like Pinterest and Instagram. Poshmark added a desktop version of the app a few years later.

"I remember the moment, six months before founding Poshmark, when Manish told me that he was going to give up his laptop and just work on his iPhone," he added.

Since then, Mayfield has participated in every single round of financing since its seed round.

Mayfield currently holds over 17.3 million Class B shares of Poshmark, according to the S1 filing.

At the opening price of $97.50 a share, Mayfield's stake is now worth nearly $1.7 billion.

Pursuing Moby Dick

The story of Poshmark started 15 years ago at a fashion show, early investor Venky Ganesan told Insider. A partner at Menlo Ventures, Ganesan described Chandra's journey as a founder as "Captain Ahab going after Moby Dick," he said.

"It's something he has been chasing, in some ways, his entire life," he told Insider.

Like Mayfield's Chaddha, Ganesan first met Chandra in 2005 through an event at the India Community Center where they attended a fashion show together.

"We were two nerdy guys from India who do engineering but have always had an interest in fashion," said Ganesan. "Manish wanted to combine the social element of a community where people talk about these things and a marketplace where people can sell it."

Besides writing the $12 million Series B check, Ganesan says Menlo Ventures, in its own way, helped Poshmark build its board. That's because two years ago, Poshmark's CEO approached Ganesan and asked him to give up Menlo's board seat to make room for Jenny Ming, former CEO and president of Charlotte Russe. (Tennis star Serena Williams also joined the board later that year).

He said "I can't really build an amazing company if I just have a bunch of guys at the table," recalls Ganesan.

Today, Ganesan says both Jenny and Serena have both been incredible additions to the board. "I know she is a 
world-class tennis player, but she acts as an investor and as a board member," said Ganesan. "I don't think I've had one tennis conversation with her."

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Today, Menlo Ventures holds over 10.3 million Class B shares, according to the S1 filing. At $97.50 a share, Menlo's potential stake is now worth over $1 billion.

GGV Capital

Like 'Chinese social shopping apps'

Hans Tung, managing partner at GGV Capital first met the Poshmark team in 2005, and immediately saw similarities  to the immensely popular Chinese social shopping apps. Tung has been a board member since April 2016.

"I liked the app for what it could be because I knew about Taobao," said Tung. Taobao is the Alibaba-owned Chinese online shopping site.

"I was very impressed with Manish because he really got that sellers and buyers can be a lot more engaged when you add community," said Tung who also had just invested in Xiaohongshu, a social commerce platform for Chinese millennials.

When asked whether he also met Poshmark's CEO through the Indian American social clubs, Tung replied, "I am not part of any club, but I was told I won their respect."

Today, GGV Capital holds over 5.1 million Class B shares, according to the S1 filing. At $97.50 a share, GGV's potential stake is now worth just under $500 million.