This 28-year-old Silicon Valley investor builds businesses by helping entrepreneurs fall in love

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Russian-born Masha Drokova, 28, poses in this handout photo provided January 22, 2018.   Courtesy of Day One Ventures/Handout via REUTERS    Thomson Reuters

  • Masha Drokova, founder of San Francisco-based venture firm Day One Ventures, believes that investing in companies is a holistic, personal endeavor.
  • She's played the part of matchmaker to several of her portfolio companies' founders.
  • Falling in love is good for business, says Drokova.

"Everyone is more productive when they fall in love," says Masha Drokova.

Drokova is the founder of Day One Ventures, a San Francisco-based firm focused on early-stage investments. The 28-year-old runs her firm differently than that of the average Silicon Valley venture capitalist: She considers investing in companies to be a deeply holistic undertaking, often forming close, personal relationships with her portfolio companies' founders.

"If I don't have a human connection with someone, I won't do business with them," says Drokova. "For me, it's never just about the money. I'm going to know most of my founders for the next five or 10 years. If you don't have a personal connection with a person, it's likely that your business relationship will fall apart."

Often, Drokova's close-knit business relationships evolve beyond a purely professional context. "I'm friends with the founders of my portfolio companies," she says. "I enjoy spending time with them and learning about them."

Sometimes, business guidance and personal advice blur together. Drokova says she sees an entrepreneur's personal well-being as a primary foundation for creating a strong business. When advising fledgling startup founders, Drokova considers their mental and physical health in addition to their business execution.

"It's often very simple things that help," says Drokova. "Meditating, eating healthy food, taking care of their physical health."

For some stressed-out founders, Drokova recommends mediation classes, podcasts, and self-developmental courses like Vipassana and sexual energy retreats.

But for others, the anecdote for the stresses of startup life is slightly more transformative. The best thing Day One's founders can do for their business?

Fall in love.

"My founders are much more grounded when they're in relationships," says Drokova. "They take on this new energy. They're more focused."

To aid her founders along in the pursuit of romance, Drokova has played the part of matchmaker to a number of her portfolio company entrepreneurs.

"It's not necessarily matchmaking," says Drokova. "I just introduce them to my friends."

Once they fall in love, Drokova says she notices an immediate difference in the way they run their business.

"They're more well-rounded," shes says. "Their partner slows them down and keeps them focused. In order to do a great, breakthrough thing, you need to be inspired."

Drokova speaks from experience. "All my best work was achieved when I was in love," she says. "Love is unexpected and exciting. It gets you engaged in life."

For startup founders working long hours, often siloed away from day-to-day life, Drokova says that romance has a tendency to reinvigorate their work, inspire their decision making process, and engage them in their professional pursuits.

There is one thing, however, that's even better for business than new romance.

"When they have a new kid being born," says Drokova. "That's when you really notice a difference."

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