Venture capitalist Brianne Kimmel says venture investing requires a certain mindset.
“The best VCs are deeply paranoid and always on the lookout for what’s next or what we’ve missed. A big 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, is focused much of this research on the changing work-life balance in the US hardly recognizes the workaholic syndrome of previous tech booms. And the effort came before Covid led to an even greater societal reckoning with the nature of the traditional workplace.
“A lot of my early investments were in remote teams and helping founders build the tools to work from home and live a more flexible lifestyle,” said Kimmel, who is 34. “This started as a passion project as an angel investor talking about remote work before the pandemic started,” she said.
Kimmel’s Worklife Ventures has invested in 50 startups to scale small businesses for freelancers, entrepreneurs, and creatives to work remotely, productively, and make connections far beyond the traditional office environment. Nine of them are worth over $1 billion, including virtual events platform Hopin, website builder Webflow, and audio-based social app Clubhouse.
Building on its network of connections that grew from leading a startup initiative for enterprise software company Zendesk, the VC firm makes about 20 new investments in the $1 million to $2 million range each year. “We now have a collection of companies committed to transforming 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 work with their personal lives, according to a recent Pew Research Center survey of nearly 6,000 adults. About half would look for a new job if they had to return to the office full-time, according to a Worklife Ventures survey of 575 employees at tech companies.
Remote work should continue to be an important factor in the job market, but it could pose a challenge for Kimmel, who ran Worklife Ventures alone for two years, to keep up the momentum — and reviews — from the pandemic upturn while dealing with a difficult economic climate. She recently fired two managers and hired former Zendesk colleague Linda Lin in their place to work with founders on go-to-market strategies, including revenue operations, growth and monetization, and scaling. Clubhouse and Hopin raised big funds on ratings in excess of $1 billion, but these once red-hot newcomers have since cut staff due to slowdowns.
In a letter to her investors about the cost cuts, Kimmel said reduced marketing spend is a function of the macro climate and the VC firm “will spend the next two quarters building deep, robust playbooks for founders.”
Worklife Ventures holds weekly meetings for the founders of its portfolio companies to seek advice from successful Silicon Valley operators.
All of this is a far cry from Kimmel’s upbringing in Youngstown, Ohio, to a working-class family of Ukrainian immigrants who worked in the city’s steel and auto industries. Like Youngstown, which is evolving from the rust industry into a technology-oriented company, she found new horizons in the digital world. After getting her degree in journalism from Kent State University and desperate to move away, she ended up in Sydney and worked in an advertising agency for five years. When she returned to the US, she got a job in San Francisco at Expedia, where she ran social media roles for three years, taught classes at the general assembly of an entrepreneurial education organization for four years, and broke through when she got her Rebranded coursework into its own unit, SaaS School, a biannual workshop for entrepreneurs to learn from fast-growing software companies. Her concept for worklife ventures was developed at Zendesk, leading its startup programs and building 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 hip Silver Lake neighborhood to host events and salons for techies, artists and creatives – and to differentiate her approach from the traditional office and VC dinners more traditionally used for industry networking.
Getting started with angel investing almost came naturally to her, but the spark came after reading Zendesk CEO and co-founder Mikkel Svane’s book, Startupland, about his experiences building a business. She wrote small checks for startups ranging from $1,000 to $5,000 at the beginning and helped founders access heavyweight investors like Andreessen Horowitz and Founders Fund to grow their small businesses. At a corporate event, she met VC Christoph Janz, a business angel at Zendesk and managing partner at the Berlin VC firm Point Nine Capital. Kimmel pitched him her idea for a fund focused on reshaping work for individual fulfillment, investing in tools like podcasting, influencer adoption campaigns, and community platforms to help freelancers and creatives become self-starters and advance their careers to pursue. Janz invested in Kimmel’s first fund in 2019.
“She is intellectually curious and interested in new technologies and also has the ability to build relationships with founders and she works hard,” said Janz. “She’s managed to invest in some great companies and has a good sense of the future of remote and hybrid work and the need for modern tools for people collaboration, and that’s accelerated tremendously. She had a good insight into 2019 from the start, which has come true.”
Kimmel was the first investor in Heylo, which was founded in 2019 by ex-Googlers Eric Winters and Brandon Pearcy as a platform for community group leaders to manage memberships, payments and event planning for social activities, and earn a commission on posts. The San Francisco-based startup has grown to 1,000 communities and raised $1.5 million in venture funding led by Precursor Ventures.
“We met through a friend and investor, and it was like we could finish each other’s sentences,” Winters said. “Brianne lives and breathes what this space is about. We have a shared vision of what the future will look like.”
Kimmel also made an early investment in San Francisco-based Deel, an people management newbie founded in 2019. Founded by technology accelerator YCombinator graduate Shuo Wang, Deel provides human resource functions such as payroll and employee benefits to widely dispersed companies on an outsourced basis. Deel achieved sales of $100 million in the 20-month period ended March 2022, growing 12 percent month-on-month, and has 10,000 customer companies in 160 countries, according to Wang. Deel has raised more than $680 million since inception, and its valuation rose to $5.5 billion in October 2021 with Andreessen Horowitz and Coatue Management in tow.
“She approached us when we were still in the early stages. She’s a super professional on the future of work and remote work,” Wang said. “She helps us a lot in recruiting people and building connections with other companies.”
Kimmel also tapped into another outsourced services startup, Pietra, and made early investments. Based in New York, Pietra offers founders a fast track to launch, with custom products from factories, e-commerce sites and supplier connections.
“We came out of beta last November and have grown 100x and helped 50,000 developers scale,” said Ronak Trivedi, CEO of Pietra, 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 leading the way with a valuation of $75 million.
“The world is rapidly shifting to owning your own business and owning your future,” he said. “Being in Brianne’s network has helped grow our business. It’s difficult for investors to create value in the companies they invest in, but she embodies what she wants to help with. She works hard to take part in the best deals, and that’s why she has this thesis about remote work and part-time jobs. This is the next generation of younger entrepreneurs, and they have the tools to have multiple revenue streams.
Several founders she has invested in say Kimmel aggressively pursues investment deals. Trivedi mentioned that she flew to NYC to have dinner with him and persuade him to take an investment from her.
“As a small VC, there are a handful of ways to build relationships. You have to look out for people and new tools,” Kimmel said. But even with her persistence, Kimmel hasn’t been able to participate in every deal she sees as part of the future of work. Merge, an HR and accounting data integration startup that raised $4.5 million in a 2021 NEA-led seed round and missed, “was #1 on my list,” Kimmel said.
Worklife Ventures is banking on good returns from its 50 startup investments, and with nine of them being unicorns, the stakes are high. Alongside Clubhouse, Hopin, Webflow and Deel, the multi-billion dollar rating list includes smart home fitness trainer Tonal, alternative financing option Pipe, investment platform Public.com, video streamer software Mux and Stytch, a passwordless authentication solution.
“Startups that quickly become unicorns often struggle to justify their valuations, and then raising successive funding can be difficult. If they get a huge injection of capital and spend that capital wisely, great. But if not, it can lead to a premature start of scaling, a tremendous burn rate,” Janz said. “They have to learn to crawl before they can walk. That’s very risky. That’s the flip side.”
Worklife Ventures’ track record depends largely on whether its portfolio companies scale intelligently, achieve profitability, are acquired, or go public. Kimmel said she intends to raise another fund, but that plan will depend on her initial performance. Because venture funds typically have a 10-year lifecycle before investment returns are counted, Worklife Ventures still has a long way to go.
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