Diversity Venture

Day One Ventures Unveils New $50M-plus Fund

San Francisco-based Day One Ventures announced a new second fund, allowing the early-stage VC company to start writing larger checks.

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The new $52.55 million fund should let Day One invest anywhere between $500,000 and $5 million in companies and possibly lead pre-seed and seed rounds, said firm founder and General Partner Masha Drokova.

Drokova founded Day One in late 2017, a year that saw 153 venture funds opened but only two led by women. While she said she does not believe it is any more difficult being a woman in the venture capital world, she admits she finds it amusing it is always a question asked.

“When I’m on these panels, no one ever asks, “What’s it like being an investor as a man?” she said.

Drokova was born in Russia, which she left in 2013, and eventually settled in San Francisco in 2015. With a background in communications–including a stint leading Runa Capital’s team—Drokova started to explore angel investing on her own. She ended up making 11 investments, writing checks averaging $15,000. 

“I wanted to do PR for companies where I’m a shareholder,” she said

That experience led her to found Day One: A name that comes from Amazon founder Jeff Bezos’ philosophy that a company should have the same focus and goals it did the day it was founded, including being obsessed with customers.

Being focused on customers is one of the main things Drokova looks at in any investment. With her background in communications, she also eyes companies where Day One can help lead messaging and outreach.

The firm’s first fund was $20 million, from which it invested between $100,000 and $500,000 each in early startups. Even though the firm typically invested in pre-revenue companies, 15 companies from that fund now have ARR anywhere between $5 million and $40 million, she added. 

The fund included investments in companies such as Superhuman, DoNotPay, Yumi, DuckDuckGo, MSCHF and Truebill. Truebill, a personal finance tool, announced its $17 million Series C round earlier this month led by Bessemer Venture Partners

That first fund already has seen three exits—all through M&A—although Day One is focused on long-term growth, Drokova said.

Diversity also was a theme in the fund, with investments going to 25 female founders and 33 percent of capital going toward founders of color. Founders of companies supported in the fund came from more than 20 different countries, she added.

Still, Drokova insists diversity is not something the firm actively strives for, but rather comes organically.

“It’s not a focus but just comes naturally to us,” she said. “We really don’t make an effort for it.”

The second fund will continue with many of the same themes as the first, eyeing customer-focused startups that Day One can help with cross-messaging, Drokova said. The firm typically likes to invest in traditional sectors—including fintech, remote work and artificial intelligence—but also branches out into the less-traditional, like quantum technology and satellites, she said.

Day One often works with firms such as Andreessen Horowitz, Founders Fund, Lightspeed and Index Ventures on investment opportunities be it seed rounds or later, Drokova said. About $45 million of the new fund came from investors, mainly technology entrepreneurs, founders and executives, from the first fund, she added.

Drokova anticipates the new money will take about two to two-and-a-half years to fully deploy, and while she does not think being a woman in the venture capital world is hard, she acknowledges other difficulties.

“We want to be the best investor these companies have,” she said. “That’s what is difficult. We really have to stand out.”


Photo of courtesy of Masha Drokova courtesy of Day One Ventures

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