When Vipin Mathew Chamakkala first spotted Amanda Elizabeth Robson at his previous company’s karaoke outing in Manhattan’s Koreatown in May 2021, he wondered what an interloper was doing there.
Ms. Robson, who goes by Robby, had been at a business lunch with his colleagues earlier that day. When they mentioned the karaoke event, she thought it sounded fun and invited herself.
At first sight of Mr. Chamakkala that evening, she was intrigued. Her interest was further piqued when he duetted with a male colleague to Kid Rock’s “Picture” featuring Sheryl Crow; they took turns singing both parts.
“He was not friendly at first,” she said. But once they started chatting and had a few beers, she felt at ease with him. They later decided to walk to Chinatown for a bite, but the restaurant was already closed, so they settled on pizza.
He then walked her to her rental apartment in TriBeCa, where he kissed her good night.
Both had been working temporarily for different companies in New York, but lived in San Francisco — she in the Pacific Heights neighborhood, he in the Mission district.
Though Ms. Robson worried when Mr. Chamakkala didn’t ask for her phone number, she needn’t have; he sent her a direct message on Instagram soon after.
Their first official date followed in July after they returned to San Francisco. Since Mr. Chamakkala was relatively new to the Bay Area, they did a GoCar tour, requiring them to sit close to one another in the small, three-wheel vehicle. Drinks and her favorite dessert, Key lime pie, followed at the Blue Mermaid restaurant at the Argonaut Hotel.
By their third date — seeing Zedd, a D.J., at 1015 Folsom, a San Francisco nightclub, that August — both knew they were falling in love.
“I remember thinking to myself, ‘Relax, you’re still getting to know each other,’ but I couldn’t help how I felt,” Ms. Robson would later say in her vows.
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In September, Ms. Robson’s job called her back to New York for a week and a half. “I felt my life without Robby kinda sucks,” Mr. Chamakkala said.
Ms. Robson, 31, is a partner in Cowboy Ventures, a women-led venture capital firm based in Palo Alto, Calif. She is also the founder of Modern Angels, a community of female and nonbinary angel investors. She grew up in Hamilton, Ontario, and is a graduate of Ivey Business School at the Western University in London, Ontario.
Mr. Chamakkala, 35, who grew up in Selden, N.Y., is the son of immigrants from Kerala, India. He is a senior director for customer partnerships at Sequoia Capital, a venture capital firm based in Menlo Park, Calif. He graduated from Fordham University. Both Mr. Chamakkala and Ms. Robson were on the Forbes 30 Under 30 list in venture capital: he in 2018, she in 2021.
By March 2022, they moved in together in the NoPa neighborhood of San Francisco, where they still live.
In October 2022, so unsuspecting of Mr. Chamakkala’s beach outing was Ms. Robson that when they reached a blanket with champagne on Marshall’s Beach in San Francisco, she assumed it was for someone else. Mr. Chamakkala got down on one knee to propose — and drew a complete blank. “My boss told me to think about what I was going to say and be sure it’s meaningful,” he said. “I had this whole thing I wanted to say, and I maybe said three lines of it.”
Afterward, family, friends and colleagues surprised her at their apartment.
The two were married on Aug. 19 in front of 181 guests by Sean O’Connor, a close friend and Universal Life Church minister, at the Triple S Ranch in Napa, Calif.
As part of the wedding ceremony, Mr. O’Connor read seven core values that the couple consider the bedrock of their partnership. They included: “their devotion to uplifting the communities around them; their belief in true equality and fairness and cherishing diversity in all of its forms as a source of strength and beauty; and their deep respect for each other’s origins, honoring the experiences and places that have shaped them.”
The couple had kicked off their wedding weekend the day before with an Indian welcome dinner, with karaoke. They sang “Picture” — this time with Mr. Chamakkala doing Kid Rock’s part and Ms. Robson doing Sheryl Crow’s.
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