The future of independent workers: why we invested in Contra 🚀

Cowboy Ventures
Cowboy Ventures
Published in
2 min readFeb 23, 2021

By Ted Wang and Jomayra Herrera

At Cowboy, we know the way people think about work is dramatically changing and we are excited to invest in companies that are helping to build that future. In 2019, there were over 50M freelancers in the US alone and that number has only skyrocketed during the pandemic, with freelancers contributing over $1.2T to the economy. Designers and other creatives have worked as freelancers for many years, and this way of working is growing more popular among a range of knowledge workers including product managers, engineers and marketers. However, the infrastructure to match skilled, high quality people with these opportunities and manage and pay them is missing.

Today, we are thrilled to announce our investment in Contra, a company we believe will provide that support for independent workers. Contra is building a professional network for independent workers, which includes:

  • access to a community of other independent workers,
  • a digital professional identity that showcases your work and not just your credentials,
  • connections to the network of people you’ve worked with in the past, and
  • a way to find job opportunities and get paid.

When we met Ben Huffman (CEO) and Gajus Kuizinas (CTO), we were immediately impressed by their deep empathy for the challenges independent workers face. They had a simple but unique insight: the primary way most freelancers find jobs is through word of mouth — so why not leverage that to build a trusted community? In Contra, independent workers upload past projects and then add “collaborators” they’ve worked with who can vouch for that experience. These collaborators create the basis for the user’s trusted professional network, creating an online version of the traditional word of mouth network.

Without officially launching, Contra already has garnered hundreds of thousands of users who have signed up to create a new professional identity. This demonstrates how badly modern knowledge workers want this new way to work. With this launch, Contra is releasing valuable features such as the ability to offer services based on your specific skills such as web design or SEO strategy and the ability to create lists of your favorite collaborators. We believe that these are the key enablers required to serve modern knowledge workers and expand opportunities for individuals residing outside the traditional technology hubs.

✨ Are you a freelancer and want to create a Contra profile? Sign up here.

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Cowboy Ventures
Cowboy Ventures

A seed-stage focused technology fund backing exceptional founders.