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How A Spotify Playlist Helped Startup Vet Kristina Simmons Raise A $20 Million Fund

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A former Khosla Ventures investor and operator at Lululemon and Juicero, Simmons overcame a scary health diagnosis and tightening venture climate to have a baby and launch her new VC firm, Overwater Ventures, all at once.


Ahead of meetings with potential investors, Kristina Simmons likes to send over an unusual prep document: a playlist. Clocking in at one hour and two minutes on Spotify, the 17 tracks start with Kid Cudi’s ‘Surfin’’ and flow through hits from Katy Perry, Beyoncé and Ellie Goulding before closing with Jack Johnson’s cover of John Lennon’s ‘Imagine.’

Simmons curated the playlist in April 2021, not long after leaving a job at storied venture capital firm Khosla Ventures to set out on her own. Now, it’s the score for her new firm, Overwater Ventures, sent to each potential backer as a soundtrack for Simmons’ thesis, broadly framed around human and planet health.

“I’ve had a few investors write to me that they’ve never had a VC send them a Spotify playlist before,” Simmons told Forbes. “My personality is my style: I hustle, I follow up right away. I try to do things differently.”

That approach helped Simmons, 35, to recently close Overwater’s first fund, a $20 million early-stage fund that has made 10 investments to date, with check sizes typically ranging from $500,000 to $2 million. And it also explains why Simmons, who has alternated between investing and operational roles during her career, was able to persevere despite what might have otherwise proven a devastating medical diagnosis (she’s fine now).

A Michigan native and University of Michigan graduate, Simmons got her first big break after sending Lululemon a presentation explaining why it should launch an ecommerce business, only to be rebuffed. After flying to Vancouver and convincing the then brick-and-mortar-focused retailer’s CEO to take a meeting in 2008, Simmons served in various social media, marketing and digital roles, eventually leading its emerging products group. In 2013, she left Canada for the Bay Area and a job at Andreessen Horowitz as a young investor.

But by the following year, a buzzy new startup with significant venture backing came calling: ill-starred juice squeezer outfit Juicero, now infamous for its high price tag and simple product. Simmons became the company’s head of marketing and business development, working at Juicero for nearly three years before the brand shut down in 2017. “What I learned was that if you don’t take risks, you don’t see rewards. It was an amazing learning experience,” Simmons said. “And now I have the credibility to tell my entrepreneurs not to raise $100 million pre-revenue. I recommend you don’t do that,” she quipped.

As chief of staff to Khosla Ventures’ billionaire founder Vinod Khosla next, Simmons spent more than three years investing in new companies, managing relationships for the firm like with its Y Combinator alumni portfolio – and learning directly from Khosla himself. One company she worked closely with was Overture Life, a Spain-based company focused on automating embryology lab processes like in vitro fertilization and egg-freezing.

By 2021, Simmons believed she saw an opportunity in the VC market for a boutique investor with consumer expertise to help highly technical founders get their brands products to a wider market. Industry peers, too, were encouraging her to use that know-how to launch her own brand. Having seen other new funds struggle to find perfect partner fits, she decided to raise a solo general partner fund. The name Overwater came from a dinner discussion about how to keep entrepreneurs from ending up in the opposite situation — underwater.

Early into fundraising, however, in the summer of 2021, Simmons was nearly taken down by her own rip tide. Asked repeatedly about her own health in the context of the fund’s future (“what would happen if you were hit by a bus?”), the fitness-minded Simmons opted for a full-body MRI scan to demonstrate her perfect health. Instead, she received a shocking result: a brain lesion that, according to one doctor who examined the results, could mean she had just nine months to two years to live. Simmons took to LinkedIn messaging any neurosurgeon in her mutual contacts; within two days, she was in touch with five.

Unsure of her diagnosis, Simmons had to reflect on continuing with Overwater. Within a month, her prognosis looked more promising; working with multiple companies looking to have an impact in health, meanwhile, felt like a good way to make a difference with whatever time she had left. So Simmons kept fundraising. After almost a year, and with her now pregnant, her army of doctors determined the brain abnormality to be benign. “Life is too short, so you should just do the things you want to do,” the Bay Area-based Simmons explained over Zoom in April. “Which is why in one year I raised a fund, got married and had a baby – did all of the things – at the same time.”

Today, brain health and fertility and family health are several areas of focus for Simmons at Overwater, alongside digital health and businesses using technology or science around climate. Investing at the pre-seed through seed-plus stages, Overwater looks to take positions of about 5% to 15%, with room to invest in about a dozen additional companies from its first fund. Portfolio companies today include Overture, the company she worked with while still at Khosla Ventures and which just had its first baby born with help from its tools; Gameto, a woman-led biotech startup looking to reverse menopause that just signed a licensing agreement to use Harvard technology to grow “living, fully human ovarian organoids” for research use; and Overstory, a company using AI to scan land and forests to help prevent wildfires.

At startup Zero Acre Farms, which produces a cultured, non-vegetable cooking oil that it claims is healthier and better for the environment, CEO Jeff Nobbs said Simmons has become his go-to investor for help on marketing questions. He’s turned to her for everything from high-level strategy to evaluating resumes.

“She’s a super high energy person who never gets down about things,” added Vijit Sabnis, a former Khosla Ventures colleague now working on an unannounced biotech startup that Simmons has backed. “She’s always enthusiastic, looking for solutions, titrating and measuring the kind of support she needs to give. She understands better than almost anyone I’ve worked with the emotional rollercoaster that all of us go through founding and running our companies.”

Simmons is the only investment partner at Overwater, but she isn’t sailing fully solo. To build out Overwater, she enlisted the help of startup and tech executives she knew (or cold-messaged on LinkedIn) to form virtual investment committees for deals. She also hosts “On The Dock” monthly sessions for founders to discuss challenges with other experts.

In a tech investment environment still reeling from the collapse of startup ecosystem backstop Silicon Valley Bank, continued rounds of layoffs and diminished dollar amounts for startups and venture firms alike, particularly emerging fund managers, raising Overwater wasn’t easy for Simmons, either. “It was like playing ‘Frogger’ where there are 2,000 lanes and the cars were coming to hit you,” she said.

Raising a fund, of course, is just the start for an investor: while some of Simmons’ companies have shown positive momentum, she has yet to enjoy a signature exit, or prove she can deliver financial returns. But with the help of her Spotify playlist, she’s confident in her chances: “The easy way is not always the right way.”

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