Lettuce Financial Raises $28 M Led by Zeev Ventures; Expands AI-Platform for Solopreneurs

Company & Market Background

Founded in 2023 by CEO Ran Harpaz and headquartered in San Francisco, Lettuce Financial addresses an often-undervalued segment of the U.S. workforce: solopreneurs and independent professionals. These “businesses of one” include consultants, therapists, freelancers, creators and fractional executives who earn six-figure incomes but typically lack access to integrated financial services. According to Lettuce, 5.6 million U.S. solopreneurs earn over USD 100,000 annually, nearly doubling since 2020.

Lettuce’s core product is the “soloOS” operating system: an AI-enabled platform built to handle accounting, tax strategies (including S-corp compliance), banking, invoicing, payroll and benefits in one unified stack. The aim is to offer solo professionals the kind of infrastructure formerly only available to companies with many employees.

The Funding Round & Acquisition

In November 2025, Lettuce secured a USD $28 million funding round, led by returning investor Zeev Ventures. The round will support product development, go-to-market expansion and new feature launches focused on benefits and healthcare for solos. Concurrently, Lettuce announced the acquisition of benefits-access startup Besolo, which will integrate healthcare and retirement benefits functionality into the platform. Besolo’s founding team will join Lettuce to lead the healthcare initiative.

While the exact valuation of Lettuce post-round wasn’t publicly disclosed, reports indicate this is the company’s third major raise after a USD $6 million seed round and USD $15 million Series A.

Strategic Implications & Growth Focus

The funding and acquisition reflect a broader strategic shift for Lettuce—from a tax & accounting tool for solos toward a comprehensive financial-services ecosystem. Key strategic focuses include:

• Enhanced AI capabilities: Lettuce plans upgrades to its “LettuceHead AI” knowledge-base and voice interface, enabling solopreneurs to manage operations through conversational commands.
• Benefits and healthcare integration: The Besolo acquisition adds health, dental, vision and retirement plan options tailored for solo workers—previously challenging for this demographic to access affordably.
• Automation of tax, payroll and compliance: With the complexities of U.S. tax systems (S-corps, self-employment taxes) and payroll for one-person businesses, Lettuce’s platform aims to reduce friction and cost.
• Market expansion and scale: The round is being used to deepen go-to-market efforts, strengthen partnerships (e.g., independent workforce platforms) and increase platform adoption across high-earning solos.

The Solopreneur Economy & Why It Matters

The rise of the solopreneur economy is significant. Many professionals now operate as freelancers, independents or one-person businesses—and yet are underserved by traditional financial and benefit systems designed for employees or larger firms.

Lettuce positions itself in a niche that combines high addressable market size with clear under-served needs: tax strategy for solos; access to benefits; integrated payroll and banking without the overhead of hiring staff. The USD $28 m round underscores investor confidence in this business model.

Competitive Landscape & Differentiation

Lettuce competes with a mix of accounting platforms (e.g., QuickBooks, Xero), payroll/benefits providers (e.g., Gusto) and fintechs focused on freelancers. Its differentiator: an AI-native platform built specifically for solos, bundling tax, payroll, retirement, banking and benefits—in effect providing “corporate grade infrastructure” to one-person firms.

The integration of Besolo enhances “stickiness” by adding benefits and healthcare—areas where solo professionals often face high cost and fragmentation. By bundling financial and benefits services, Lettuce aims to improve ARPU (average revenue per user) and retention.

Risks & Considerations

While the opportunity is strong, some risks remain:

• User acquisition and scaling: Reaching large numbers of solo professionals—especially via partners—will be crucial.
• Execution of benefits stack: Healthcare and retirement offerings require regulatory compliance, provider contracts and user trust.
• AI-governance and reliability: As financial tools become AI-powered, accuracy, explainability and trust become key—especially with tax and compliance.
• Competition and pricing pressure: Incumbent platforms may expand offerings for solos; maintaining differentiation is important.

Outlook & Next Steps

In the near term, key developments to watch include:

• Launch timelines for the upgraded AI and voice-interface features of soloOS.
• Rolling out bundled healthcare/benefit products via the Besolo integration.
• Growth metrics: number of solopreneur users onboarded, revenue growth, ARPU uplift via benefits.
• Partnerships with freelancer marketplaces, professional networks and payroll/benefit providers.
• Any future fund-raising, valuation steps or moves toward broader platform expansions beyond U.S. solos.

If executed effectively, Lettuce could become a foundational fintech infrastructure provider for a large and growing segment of the workforce—one-person businesses—with the potential for strong recurring revenue and high customer lifetime value.

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