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How Kristina Simmons, a Seasoned Startup Founder, Used a Spotify Playlist to Raise $20 Million

How Kristina Simmons, a Seasoned Startup Founder, Used a Spotify Playlist to Raise $20 Million

Kristina Simmons is known to deliver an unusual preparatory document to investors before meetings: a playlist. Timed at exactly one hour and two minutes on Spotify, the compilation of 17 songs begins with “Surfin” by Kid Cudi and continues through songs by Katy Perry, Beyoncé, and Ellie Goulding, before ending with Jack Johnson’s rendition of “Imagine” by John Lennon.

In April of 2021, after deciding to strike out on her own, Simmons compiled the playlist you’re listening to now. Now it serves as the music to Simmons’ thesis, which is broadly framed around human and planet health and is sent out to possible investors by her new company, Overwater Ventures.

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“I’ve had a few investors write to me that they’ve never had a VC send them a Spotify playlist before,” Simmons said to Forbes. “My work ethic and promptness are hallmarks of my demeanor. I always attempt to find new approaches.

To date, Simmons’s (age 35) strategy has resulted in 10 investments from Overwater’s inaugural fund, a $20 million early-stage fund with average check sizes of $500,000 to $2 million. The fact that Simmons, who has held both investing and operational positions over the course of her career, was able to keep going in the face of what could have been a terminal illness explains her current good health.

The idea for an online clothing store for Lululemon

Simmons, a native Michigander, and a University of Michigan alumna, got her big break when she pitched an idea for an online clothing store to Lululemon and was rejected. Simmons began working for the company in various social media, marketing, and digital jobs in 2008 after flying to Vancouver and convincing the CEO of the then brick-and-mortar-focused business to take a meeting. She moved from Canada to the Bay Area in 2013 to work as an associate at the venture capital firm Andreessen Horowitz.

But the following year, Juicero, an ill-fated juice squeezer company with major venture financing, came knocking with its high prices and simplistic product. For nearly three years before the Juicero brand was discontinued in 2017, Simmons served as the company’s head of marketing and business development. What I found out is that there are no payoffs if you don’t take any chances. Simmons described the event as a “fantastic opportunity for growth.” And now I can say to my startup founder clients, ‘Don’t go out and raise $100 million before you have any revenue.'” I wouldn’t advise it,” she joked.

Simmons’s Experience as Head of Staff

Simmons then spent over three years as Khosla Ventures’ head of staff, learning from billionaire founder Vinod Khosla as they made investments in new firms and managed connections with the firm’s Y Combinator alumni portfolio. Overture Life, a Spanish firm specializing in robotic automation for embryology lab procedures including IVF and egg freezing, was a client she frequently collaborated with.

Simmons predicted that by 2021, the VC market will be ripe for boutique investors with consumer skills to assist highly technical founders in expanding the reach of their businesses. Her contemporaries in the business world also urged her to put her expertise to use by creating her own line of products. She decided to start raising a general partner fund on her own after seeing how difficult it was for other new funds to attract suitable investors. The company was named Overwater as its founders spent an evening discussing how to ensure that budding businesspeople never find themselves in the opposite situation: underwater.

Simmons was almost drowned

Simmons was almost drowned in the riptide of her own fundraising efforts in the early summer of 2021. After being grilled regarding the future of the fund based on her health (e.g., “What would happen if you were hit by a bus? “), fitness fanatic Simmons decided to get an MRI of her entire body to prove she was in ideal shape. Instead, she received the devastating news that she had a brain lesion, which one expert examining the results speculated could mean she only had nine months to two years to live. Within two days, Simmons had messaged five of the neurosurgeons within her LinkedIn connections.

Simmons had to choose whether or not to continue with Overwater given the uncertainty of her diagnosis. Within a month, her prognosis improved, and she believed she could do her best by working with a variety of organizations hoping to improve people’s health. So Simmons continued to seek donations. The anomaly in her brain was deemed benign after nearly a year, by which time she was pregnant. “Life is too short, so you should just do the things you want to do,” Simmons, who is located in the Bay Area, said in April through Zoom. That’s why I managed to get married, have a baby, and raise money all in the same year.

Simmons at Overwater focuses on brain health, fertility, family health, digital health, and climate change-related firms. Overwater will invest 5–15% of its initial fund in 12 pre-seed to seed-plus firms. Overstory, a former Khosla Ventures client, uses artificial intelligence to scan land and forests to prevent wildfires, and Gameto, a women-led biotech startup that reverses menopause, recently signed a licensing agreement to use Harvard technology to grow “living, fully human ovarian organoids” for research.

Simmons is a go-to investor

Jeff Nobbs, CEO of Zero Acre Farms, a firm that makes a cultured, non-vegetable cooking oil that it claims is healthier and better for the environment, has indicated that Simmons has been his go-to investor for guidance on marketing concerns. He has consulted her on everything from broad strategic questions to the evaluation of job applications.

“She’s a super high-energy person who never gets down about things,” said Vijit Sabnis, a former Khosla Ventures colleague who is now working on a secret biotech startup that Simmons has sponsored. She is always upbeat, on the lookout for answers, and carefully gauging the level of help she can provide. She gets the ups and downs of starting and maintaining a business and the emotional toll it takes better than nearly anyone I’ve dealt with.

Simmons is Overwater’s sole investor, but she isn’t completely on her own. To develop Overwater, she formed virtual investment committees for deals with the assistance of startup and tech industry professionals she knew (or cold-messaged on LinkedIn). She also holds monthly “On The Dock” events, where founders can talk to her and other professionals about their problems.


The failure of Silicon Valley Bank, which provided a safety net for the startup ecosystem, ongoing waves of layoffs, and reduced dollar amounts for startups and venture companies, particularly rising fund managers, made it difficult for Simmons to raise Overwater in the current tech investment environment. She compared the experience to playing the video game “Frogger,” only with 2,000 lanes and oncoming vehicles.

While Simmons’ enterprises have demonstrated promising growth, she has yet to have a trademark exit or demonstrate her ability to produce financial returns to investors. But she’s feeling optimistic because of the songs on her Spotify collection, especially this one: “The easy way is not always the right way.”

About Emerson Hardy-Blue

Emerson Hardy-Blue is a prolific author specializing in the world of entrepreneurs and founders. With a deep passion for business and innovation, he delves into the journeys, challenges, and triumphs of visionary individuals. Emerson's writings provide invaluable insights and practical advice for aspiring entrepreneurs, offering a roadmap to success. Through his engaging storytelling and expertise, he inspires and empowers readers to pursue their entrepreneurial dreams with confidence and determination.