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Collective, a platform and advisory team that provides bookkeeping, payroll and tax advice to freelancers, today announced it raised $50 million in a funding round led by Gradient Ventures, Innovius Capital, The General Partnership, General Catalyst, QED, Expa and Better Tomorrow Ventures.
The tranche brings Collective’s total raised to $82 million. It’ll be put toward investments in product development and scaling the company’s operations, co-founder and CEO Hooman Radfar says, growing Collective’s 200-employee headcount by about 30% by next June.
“During economic slowdowns like the 2008 recession, the COVID-19 pandemic, and, more recently, the headwinds experienced by the tech sector, the self-employed market has experienced significant growth,” Radfar told TechCrunch in an email interview. “This investment round showcases our strong positioning and growth trajectory.”
Ugur Kaner, Bugra Akcay and Radfar co-founded Collective, which is based in San Francisco, several years ago. Radfar met Ugur while working as a founding partner at the VC firm Expa Ventures, and recruited Akcay, their mutual friend, to kickstart the business.
“Collective is the first all-in-one, online back office for ‘businesses-of-one,’” Radfar said. “It’s unique in that we provide all the services you would typically see in an enterprise-level finance department in one, easy-to-use platform.”
Radfar says that he was inspired to found Collective by his experiences as the child of immigrants. Both his parents chose self-employment when they immigrated to the United States. But after they divorced, Radfar’s mother opted to run her business as a sole proprietorship while his father chose to “S-elect” his company. Unlike a proprietorship, an “S corporation” can be taxed as a pass-through entity, meaning that income, losses, deductions and credits can be reported as part of a personal tax return.
“As a result of that simple choice in freelancing — formation structure — my father saved hundreds of thousands of dollars that my mother did not,” Radfar said. “Entrepreneurship is being hindered by an antiquated approach to financial management, preventing businesses of one from effectively running their operations in a manner that maximizes their net income.”
Collective aims to provide all the services you’d typically see in an enterprise-level finance department. Leveraging AI (specifically OpenAI’s GPT-4), the platform attempts to automate processes like categorizing expenses and bank reconciliation. Beyond this, Collective offers tools for tasks like executing payroll, filing quarterly and annual taxes and tracking monthly expenses and deductions.
The goal is to eliminate the need for self-employed people to rely on separate tools for payroll, bookkeeping, taxes and accounting, Radfar says — one of the hardest aspects of freelancing. According to one poll, managing finances — e.g. invoicing, tracking expenses and paying taxes — is a significant challenge for 18% of freelancers.
“Our members are not only the owners of their businesses, but they’re also responsible for key decisions around the tools and services,” he added. “That’s why Collective is valuable for this category — any time they can save is extra time that they can leverage to provide services to their clients.”
Collective, which claims to serve thousands of members across the the U.S. (and “eight-figure” annual recurring revenue), with a waitlist exceeding 100,000, eventually plans to work with Big Tech companies like Google and Meta to provide membership to its services as a benefit to contractors.
It’ll have to best the competition to get there. There’s Wingspan, which offers an all-in-one payment platform for contractors. Elsewhere, Beam provides an array of tools to help contractors get paid faster, albeit contractors primarily in the construction industry.
Asked about the rivals, Radfar pointed out that the market for freelancer financial services is vast — and steadily growing. Thirty-nine percent of the U.S. workforce now participates in freelance work, a proportion that’s projected to increase to over 50% by 2027.
“The primary competition that Collective faces are hyperlocal accountants and service providers,” Radfar said. “A less-used alternative by our core demographic would be using DIY tools for formation, bookkeeping, tax and payroll. [But] given the income level of our customers, they don’t often view the ‘do it yourself’ alternative as a real alternative.”
Gradient Ventures’ Darian Shirazi added via email: “Language models will enable operationally-intensive processes to scale more quickly and with lower cost. Collective is harnessing this capability by applying AI to the process of bookkeeping, accounting and reconciliation. Collective’s complex workflows and proprietary data uniquely position them to leverage AI to disrupt the tax and accounting market.”

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