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Investor Chris Sacca laments the one that got away: Snap

Chris Sacca, founder of Lowercase Capital LLC, speaks during an interview at the DreamForce Conference in San Francisco, Tuesday, Oct. 4, 2016.
David Paul Morris | Bloomberg | Getty Images
Chris Sacca, founder of Lowercase Capital LLC, speaks during an interview at the DreamForce Conference in San Francisco, Tuesday, Oct. 4, 2016.

Oh, Snap!

Silicon Valley investor Chris Sacca really regrets not answering an email from Snap CTO Bobby Murphy back in 2012.

That same year, Murphy and Snap co-founder and CEO Evan Spiegel inked their first deal with outside investors: Lightspeed Venture Partners invested $485,000 in a seed round, then participated in follow on funding rounds.

The young company would not be working out of that Palisades house Murphy invited Sacca to have lunch at for much longer — Lightspeed also gave the company office space.

When Snapchat first approached Sacca in 2011, he was put off by its image as a sexting app, he told CNBC in a December interview.

"The Snapchat guys came up to me after a talk once, and I said I'm really flattered but the pics of your junk... really? So I passed. Later I told my business partner ten years younger than I am and he lost his mind. (He said) 'do you realize what Snapchat is?' That probably cost me a billion dollars or two," Sacca told CNBC.

Bobby Murphy, co-founder and chief technology officer at Snap Inc., from left, Evan Spiegel, co-founder and chief executive officer of Snap Inc., ring the opening bell at the New York Stock Exchange (NYSE) with Tom Farley, president of the NYSE Group, during the company's initial public offering (IPO) in New York, U.S., on Thursday, March 2, 2017.
Michael Nagle | Bloomberg | Getty Images
Bobby Murphy, co-founder and chief technology officer at Snap Inc., from left, Evan Spiegel, co-founder and chief executive officer of Snap Inc., ring the opening bell at the New York Stock Exchange (NYSE) with Tom Farley, president of the NYSE Group, during the company's initial public offering (IPO) in New York, U.S., on Thursday, March 2, 2017.

Flash forward to Snap's public debut on the New York Stock Exchange Thursday, and Lightspeed got a huge payday. The firm sold 4.6 million shares, worth a cool $79 million at the start of trading. It still holds nearly 82 million shares, worth just shy of $2 billion.

The Snap founders ultimately opted to stay down south in Los Angeles, versus moving to the San Francisco Bay Area. Whether Sacca would have advised Murphy to relocate north, we'll never know. That said, the company has stayed away from Silicon Valley, preferring its Venice, Calif. home.

Sacca — whose investments include Twitter and Facebook's Instagram — is worth an estimated $1.2 billion according to Forbes, so he's likely doing OK.

— with reporting from CNBC's Arjun Kharpal