Anyone who has been a freelancer knows the pain of trying to get paid in a reasonable amount of time, let alone on the time at all. On top of that, there’s a lot no one tells you in the beginning when getting started as a freelancer, from setting up health insurance, setting aside funds for social security, and filling out quarterly tax forms.
And amid the Great Resignation, there are more freelancers than ever in recent memory as more professionals go on their own. In turn, businesses are more open to hiring freelancers as well. A recent study from Upwork, an online hub for hiring and job listings, found that 71% of hiring managers plan to maintain or increase their use of freelancers over the next six months.
Enter Archie, a new digital services platform tailor-made for freelancers within any industry, from e-commerce to health care. But payments are only one element of what Archie says it is offering. The platform connects businesses and freelancers, facilitating the transfer of necessary information and documents (contracts, NDAs, invoices, W-9s, etc.), and taking freelancers from onboarding to payments with all the necessary steps in between, including managing end-of-year tax filings.
Launching just a year ago in April 2021, Archie has already generated more than $15 million in payment volumes—up eight times over since July 2021 alone. This week, the company announced it just raised $4.5 million in venture capital after a seed round of fundraising. Major investors include B Capital, Worklife VC, Mac Ventures, and Day One Ventures, as well as the founders of Cameo, Ramp, Blank Street, Lambda School, and Eight Sleep.
Cofounders Cassandra Aaron and Yunas Reguero recently shared more with Fortune about what the first year in business has been like and plans for the future.
The following interview has been condensed and lightly edited for clarity.
Fortune: Can you share more about your professional backgrounds prior to launching Archie?
Reguero: I grew up in Puerto Rico where delayed payments and irregular work manifested in financial insecurity for most of my and my family’s life. I was lucky to be able to work in strategy and product roles at Square and Meta [then, Facebook] to increase access to financial services. At Square, we were very focused on allowing every person to start and run a business by allowing them to accept mobile payments. During my time there, my goal was to help Square move into the small-and-medium-sized business segment (SMB) as opposed to its initial wedge into the micro-business segment (farmer’s markets, art fairs, etc.).
When I joined Meta, it was at a time when the company was making a big investment to enable businesses globally be able to sell natively across the family of apps (e.g. Facebook, Instagram, Whatsapp, Messenger, and Oculus) and give access to economic opportunity. During my time there, I focused on building and launching the first iteration of checkout on the Facebook app, Facebook marketplace, Instagram Shopping, and Facebook Shops and all the payments/commerce infrastructure to make starting a business online more accessible across the globe.
I spent a lot of time working with Latinx groups during my time at Square and Meta because nine times out of 10, I was working on teams where I was the only Latinx employee. The goal there was always about how we can attract, retain, and grow diverse talent, and I’ve taken my learnings to how we’re building Archie.
Aaron: I was a freelance strategist working in experiential marketing in Australia; it marked my first entry point into the world of being a business-of-one. After moving to New York, I landed a job at Milk Agency, a subsidiary of Milk Studios. This not only unlocked my experience into the weird and magical creative New York scene, but it exposed me to the power of community that Milk was able to build across verticals.
After two years at Milk and later, working with Archie’s founding partner Dylan Hattem at creative agency DS Projects, I had hired thousands of freelancers and became embedded in the space. I gained a deep understanding about the operational difficulties businesses and freelancers face. Additionally, during COVID, Dylan and I got a feel for launching a business together and built an e-comm startup to connect organizations in need with people who wanted to help.
What inspired you to launch Archie? What kind of gaps does this product fill for both freelancers and businesses?
Aaron: At DS Projects, I led marketing campaigns for companies like Spotify and Foot Locker. To make it all happen, Dylan and I were hiring thousands of freelancers and felt the operational pains around the end-to-end flow when working with freelancers at scale. We were hacking together the process across seven or eight online and offline tools, which was a major time suck. It took away from our ability to focus on growth-related business efforts. We sometimes hired freelancers just to deal with our other freelancers! Nothing solved this for us, so we decided to build it. We were experts in the space and needed to bring on a cofounder (Yunas), who cared about the problem with strong payment chops to help us figure out how to un-fuck the freelance economy. That’s when a casual conversation between best friends turned into a pitch to join the company and bring the dream to life.
Reguero: I had just paid off my student loans and was finally in a place where I could take the risk and join the startup world. After working at Square and Facebook, I learned how you can leverage technology to give people access to financial services in a way that wasn’t possible before. Toward the end of 2020, I was introduced to the world of freelancing where I learned about the financial hardships of independent workers. This growing workforce spends a disproportionate amount of time doing admin work as a business-of-one and oftentimes would wait more than 30 days to get paid for work that had already been done. This led us to interview hundreds of businesses to learn about how they work with freelancers and discovered that they also have issues when it comes to working with 1099 workers.
With that in mind, we decided to build a solution that facilitates the process of onboarding, paying, and doing taxes for freelancers (similar to what exists today for full-time workers). That way, businesses can save time and money while giving their freelance workers an amazing experience, which given where the world is heading, it will become increasingly important.
Archie launched just as the “Great Resignation” started to happen. How has that affected your company? Do you see a lot of new freelancers in the field or are you serving more professionals who have been freelancing for years?
Reguero: We’re seeing more and more people leaving their 9-to-5 jobs and taking a leap to work for themselves. In 2021, approximately 40 million people left their jobs and a record 5.4 million people applied for small business licenses (over 50% more than the prior year). Many of these companies are building agile teams based on their needs and hiring freelancers to scale their business. Companies that have been around are continuing to adopt freelance hiring as a practice because they get top-notch talent on demand. This paired with remote work and COVID is accelerating the trends.
However, the tools that exist for onboarding, managing, and paying freelancers are stuck in the past. Most businesses that we talk to are using a mix of email, spreadsheets, and invoice/tax/bank detail PDFs. They send wires on outdated bill pay solutions, and tax season is miserable. With freelance hiring on the rise, our value props are resonating more than ever, and we’re on a mission to bring the magic of Archie to every SMB in the U.S.
What has your experience been like approaching investors? What kind of feedback did you receive when pitching? What advice would you offer to future entrepreneurs when looking for investors?
Reguero: We’re lucky to have found investors that truly believe in and support our vision, from our lead investors B Capital Group and Mac Ventures; to Worklife Ventures, Hof VC, Dash Fund, Day One Ventures; to the founders of Ramp, Eight Sleep, Bloom Tech (formerly Lambda School), Elemy, Blank Street, NuvoCargo, and many more.
The investor feedback is always interesting. The reality is that, over the past three to four years, many companies have launched in the freelancer/creator space and so it takes some time to educate investors on our market, explain what others are doing and how we are different. For future entrepreneurs, I’d say to find investors that like your space and who you like working with, you’re going to spend many years building your business, and it makes a big difference to do it with people that give you energy.
Looking forward, how do you want to grow Archie within the next five years?
Aaron: Finishing a project should be celebratory but instead and in a world without Archie, it unlocks the second phase of dread: manual paperwork and logistical frustration. We want to make it easy—so easy that it brings joy into this new working relationship. We started by building for marketing agencies and media companies but have found that the platform also serves other verticals like retail/e-commerce, health, education, technology, and more. There’s a huge network effect around Archie (businesses tell freelancers who tell businesses and so on). We’re super excited to see this traction.
Reguero: At its core, we’re building the financial infrastructure for the future of work. It’s clear that people want to join the freelance economy but are scared of all the financial obstacles. At the same time, businesses are increasingly relying on freelancers but the tools to tap into this economy are stuck in the past. We’re building the onramp for both sides to unlock the magic of the freelance world. With all these new and decentralized ways of both working and earning, we are excited to bridge that gap and accelerate trends in freelance hiring.
This is an installment of Startup Year One, a special series of interviews with founders about the major lessons they have learned in the immediate aftermath of their businesses’ first year of operation.
