• Female venture capitalist Brianne Kimmel's Worklife Ventures has invested in 50 portfolio holdings since 2019, some which have surpassed $1 billion in value.
• She previously ran a startup initiative for business software company Zendesk and her VC is backed by Marc Andreessen and Zoom Video Communications CEO Eric Yuan.
• She plans to add 20 new investments annually, scaling up small businesses for freelancers, entrepreneurs and creators to work remotely and productively outside traditional office culture.

Female venture capitalist Brianne Kimmel says venture investing requires a certain mindset.

"The best VCs are deeply paranoid, and always looking out for what's next or what we missed. A large part of what we do is research," Kimmel said.

For Kimmel, who launched Los Angeles-based Worklife Ventures in late 2019 and has since raised two funds totaling $45 million with high-profile backers Marc Andreessen and Zoom Video Communications CEO Eric Yuan, much of that research focuses on the changing work/life balance in the U.S., hardly the workaholic syndrome of earlier tech booms. And the effort came before Covid led to an even greater societal reckoning with the nature of the traditional workplace.

"Many of my first investments were for remote teams and helping founders to build the tools to work from home and have a more flexible lifestyle," said Kimmel, who is 34. "This started as a passion project as an angel investor. I was talking about remote work before the pandemic began," she said.

Scaling up small businesses for freelancers, entrepreneurs and creators to work remotely and productively, and make connections well beyond the conventional office setting, Kimmel's Worklife Ventures has invested in 50 startups. Nine of them have been valued over $1 billion, including virtual events platform Hopin, website builder Webflow, and audio-based social app Clubhouse.  

Building upon her network of connections honed from running a startup initiative for business software company Zendesk, the VC firm makes about 20 new investments each year, in the range of $1 million to $2 million. "We now have a collection of companies that are about changing work. Kids today would rather be YouTubers than astronauts," Kimmel said.  

Even as workplaces reopen, more workers are choosing to stay at home where they can be productive and balance jobs with their personal life, according to a recent survey by Pew Research Center of nearly 6,000 adults. About half would start looking for a new job if they had to return to the office full-time, a Worklife Ventures survey of 575 employees at technology companies additionally found.

Remote work should continue to be a major factor in the labor market, but sustaining momentum — and valuations — from the pandemic bounce while facing a tough economic climate could be challenging for Kimmel, who ran Worklife Ventures solo for two years. She recently let go of two managers and in their place hired former Zendesk colleague Linda Lin to work with founders on go-to-market strategies, including revenue operations, growth & monetization, and scaling. Clubhouse and Hopin raised large funding at billion-dollar-plus valuations, but these once red-hot newcomers have since cut their staff amid slowdowns.  

In a letter to her investors covering the cost cuts, Kimmel said reduced marketing spend was a function of the macro climate and the VC firm "will be spending the next two quarters building deep, robust playbooks for founders." 

Worklife Ventures holds weekly meetings for its portfolio company founders to seek advice from successful Silicon Valley operators.

All this is a long way from Kimmel's upbringing in Youngstown, Ohio, in a working-class family of immigrants from Ukraine who labored in the town's steel and auto-making industry. Like Youngstown, which is transitioning from rust industries to tech-led businesses, she found new horizons in the digital world. After graduating with a journalism degree from Kent State University and anxious to move away, she landed in Sydney and spent five years working at an ad agency. Moving back to the U.S., she got a job in San Francisco at Expedia handling social media functions for three years, taught classes at entrepreneurial education organization General Assembly for four years, and broke through when she rebranded her coursework into its own entity, SaaS School, a biannual workshop for entrepreneurs to learn from fast-growing software companies. Her concept for Worklife Ventures developed at Zendesk, heading its startup programs and building out a base of accelerators, incubators and VC firms.

Kimmel, whose boyfriend is actor Jimmy Yang, is a super-connector. She has a network of 30,000 professional friends and colleagues, and 80,000 followers on Twitter. She recently opened Worklife Studios in LA's trendy Silver Lake area to hold events and salons for techies, artists and creators — and as a means of differentiating her approach from the traditional office, as well as the VC dinners more traditionally used in industry networking.

It was almost natural for her to start angel investing, but the spark came after reading the book "Startupland" by Zendesk CEO and co-founder Mikkel Svane about his experiences building a company. She wrote small checks of $1,000 to $5,000 in startups at their beginning, and helped founders to access heavyweight investors the likes of Andreessen Horowitz and Founders Fund to scale up their small businesses. At a company event, she met VC Christoph Janz, an angel investor in Zendesk and a managing partner at Berlin-based VC firm Point Nine Capital. Kimmel pitched him on her idea for a fund focused on reimagining work for individual fulfillment, investing in tools such as podcasting, influencer adoption campaigns and community platforms to help freelancers and creatives be self-starters and pursue careers of their making. Janz invested in Kimmel's first fund in 2019.

"She is intellectually curious and interested in new tech, and also has an ability to build relationships with founders, and she works hard," said Janz. "She has managed to invest in some great companies, and has a good pulse on the future of remote and hybrid work and the need for modern tools for people to collaborate, and that has hugely accelerated. She had good insight from the get-go in 2019, which has become more true."  

Kimmel was the first investor in Heylo, formed in 2019 by two ex-Googlers Eric Winters and Brandon Pearcy as a platform for community group leaders to manage memberships, payments and events planning for social activities, collecting a commission on dues. The San Francisco-anchored startup has grown to 1,000 communities and attracted $1.5 million in venture financing, led by Precursor Ventures.  

"We met through a friend and investor, and it was like we could finish each other's sentences," said Winters. "Brianne lives and breathes what this space is all about. We have a shared vision of what the future will look like."

Kimmel also invested early in San Francisco-based Deel, an employee-management upstart launched in 2019. Started by technology accelerator YCombinator graduate Shuo Wang, Deel provides far-flung companies with human resource functions such as payroll and employee benefits on an outsourced basis. Deel chalked up $100 million in revenue within a 20-month period ending March 2022, is growing by 12 percent month over month, and counts 10,000 client companies in 160 countries, according to Wang.  Deel has raised more than $680 million since its start, and its valuation rose to $5.5 billion in October 2021 with Andreessen Horowitz and Coatue Management in tow.   

"She reached out to us when we were early stage. She is super pro about the future of work and remote work," said Wang. "She is very involved with helping us recruit people and building connections with other companies."

Kimmel also tapped another startup with outsourced services, Pietra, and invested early. Based in New York, Pietra offers founders a quick route to launch, with custom-designed products from factories, e-commerce sites and connections to suppliers.

"We came out of beta last November and have grown 100 times and helped 50,000 creators to scale up," said Pietra CEO Ronak Trivedi, a former product manager at Uber. Pietra raised $5 million in 2019 led by Andreessen Horowitz, followed by $15 million in August 2021, with Founders Fund in the lead at a $75 million valuation.

"The world is quickly shifting to owning your own business and owning your future," he said. "Being in Brianne's network has helped to grow our business. It's hard for investors to build value in companies they invest in, but she embodies the thing that she wants to help with. She works hard to get in on the best deals and she has this thesis on remote work, and side hustles. This is the next generation of younger entrepreneurs, and they have the tools to have multiple revenue streams." 

Multiple founders she has invested in say Kimmel pursues the investment deals aggressively. Trivedi mentioned that she flew to NYC to have dinner with him and pitch him on taking an investment from her. 

"As a small VC, there are a handful of ways to build relationships. You have to have an eye out for people and for new tools," Kimmel said. But even with her persistence, Kimmel hasn't been able to get in on every deal she sees as part of the future of work. Merge, a business startup to integrate HR and accounting data, which raised $4.5 million in a seed round in 2021 led by NEA, and which she missed out on, "was No. 1 on my list," Kimmel said. 

Worklife Ventures is betting on good returns from its 50 investments in startups, and with nine of them as unicorns, the stakes are high. In addition to Clubhouse, Hopin, Webflow and Deel, the billion dollar-plus valuation list includes smart home fitness trainer Tonal, alternative finance option Pipe, investing platform Public.com, video streamer software Mux, and Stytch, a password-less authentication solution.

"Startups that quickly rise to unicorn status often struggle to justify their valuations and then it can be difficult to raise successive funding. If they get a huge injection of capital and spend that capital wisely, great. But if not, it can lead to premature scaling, a huge burn rate," Janz said.  "They have to learn to crawl before they can walk. It is very risky. That is the downside."

The track record of Worklife Ventures depends largely on whether its portfolio companies can scale up smartly, achieve profitability, get acquired or go public. Kimmel said she intends to raise another fund, but this plan hinges on her initial performance. With venture funds typically having a 10-year life cycle before investment returns are tallied, Worklife Ventures still has a ways to go.

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