Paradigm shifts around how we view work, accelerated by the pandemic, are causing the unbundling of professional identities and the companies where people work. Grace Chou, partner at Maveron, examines how the growing influence of trends like side hustles and upskilling will create a future in which work is far more multifaceted than in the past. This requires reimagining the stack of technological infrastructure and reputational tools.


Why is the future of work such an important category moving forward?

  • Paradigm shifts, including the rise of the side hustle and the emergence of the creative class, are unbundling people's professional identities away from the traditional workplace. “Around 40% of Americans now say that they pursue more than one line of work, and these extra revenue streams are more passion-driven,” says Chou. Additionally, creative work is now the top career choice for a significant portion of Gen Z. “We’re seeing the rise of this creative class that's allowing people to monetize their creativity, passion, and individual skill sets. As we dig into this space, it’s already grown to a $100B+ market with 50 million Americans identifying as creators,” she says.

The creative class has already grown to a $100B+ market with 50 million Americans identifying as creators.

Grace Chou~quoteblock

  • New platforms are going to market by empowering people to upskill or re-skill in response to the rapidly shifting labor market. “A huge majority of companies, somewhere over 80%, are reporting labor skills gaps right now. And while you’re seeing automation around some jobs, this is also creating an opportunity for helping people up-skill or re-skill to land jobs that give them more fulfilling work and means to thrive.”

What are the business models that might be attached to this category?

  • A new generation of social branding platforms that support the growing independence of the professional identity and resume. “The big theme here will be the unbundling of Linkedin as solopreneurs and creators opt for more authentic mediums,” says Chou. Platforms like Contra and Polywork are enabling solopreneurs to showcase their work and find collaborators and projects to work on. “Right now, your resume is tied to where you have worked, but there’s a shift towards platforms that show your projects and skill sets and connect you with people who do similar kinds of work,” she says. Moreover, people now crave authenticity at work — Candor is a building a new professional network that allows you to authentically showcase your values, working style, and personality with your teammates and broader community.
  • Similarly to how Shopify empowered smaller E-commerce players, a new tech-stack will emerge to support creators and multi-income workers. “Shopify changed commerce from something that required building a large company to something that could be done as a one man shop, and we are seeing similar evolution in the creative space,” she says. “Companies like Substack, Patreon now support decentralized content creation, and platforms like Future, Karat, Juice, Stir provide financial services and back-office tools to allow solopreneurs and creators to work independently. We are excited about continued innovation taking place across the entire creative tech stack.”

What are some of the potential roadblocks?

  • High saturation in many opportunity areas will complicate competitive differentiation. “As the landscape becomes increasingly crowded, it is critical for founders to focus on focusing on a delightful user experience that emphasizes a robust feature set, trust and security, and ease of use. Some important questions to think about as you build: how do you make sure you’re a platform vs a feature, how do you create network effects, and how do you build a product that becomes truly irreplaceable?” says Chou.
  • Evolving advertising environments are complicating customer acquisition. “Obstacles around customer acquisition are a common trend throughout consumer facing markets because we’re entering a new world where you can no longer rely on direct-to-consumer paid advertising from platforms like Facebook,” she says. Players in this space will need to find creative ways to tap into an emerging set of distribution channel.


saidbyblock~ via Zoom interview
Grace Chou

There’s been a paradigm shift around how people view work. Whether that's around how they define it, where they do it, or where they find it, the future of work is becoming much more fluid. Power is shifting toward the consumer and the talent.

We’re seeing an unbundling of work identity away from companies and towards self and connection with others. The rise of the side hustle, the growth of the creative class, and the popularity of up-skilling and re-skilling are all contributing to this new environment and attitude.

Many work identities are going to break free from vertical confinements as people pursue multifaceted roles across industries and in line with their passions. In response to this, we will see archaic and generalized platforms that supported traditional, corporate oriented structures replaced with a new generation of platforms grounded in personal identity and experience.


Generative AI and other technological advancements could enhance the creator tech stack. “It’s a bit early to tell whether Generative AI will create a whole new set of consumer apps and business models, but in the near term we should see enhancements from existing platforms that can empower people to do more creative work in new ways,” says Chou.

Enterprise pushback could become an obstacle as companies adjust to post-pandemic conditions and shift some work back in-person. While the leverage is shifting in favor of the talent, corporate pushback may rise around multi-income and side hustle trends as employers try to improve their output and protect bottom lines in the challenging macro-environment.


The 2022 EVC List honors the top 50 rising starts in venture capital. Terra Nova’s Thesis Brief series showcases each investor’s insights and category expertise.

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