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Lettuce Financial, a San Francisco-based fintech platform for solopreneurs, has secured $28 million in additional funding to accelerate the expansion of its AI-powered operating system, soloOS, which targets one-person businesses focused on growth, the company announced today. Lettuce — which targets self-employed professionals with an accounting, payroll, benefits, and tax compliance platform — also announced it has acquired Besolo, a benefits startup, to bring its subscribers access to more robust healthcare options and other benefits. Lettuce will also bring on advisor Molly Loftus, formerly a Cigna executive, chief actuary at Mercer and CEO of Consortium Healthplans. Zeev Ventures led the funding round. The venture capital fund has also backed companies such as Houzz and exited from Audible, Chegg and Next Insurance. Ran Harpaz, founder and CEO of Lettuce, said the company wants to address a gap in the marketplace for infrastructure to support solopreneurs such as physicians, therapists, content creators, consultants, and fractional executives, who have typically had to piece together business and financial tools from multiple providers. “I think the future is independent,” he said in an interview. “We are very much committed to making that infrastructure available and building Lettuce for that purpose.” Ran Harpaz, founder and CEO of Lettuce, a fin-tech platform targeting solopreneurs, is looking to expand health benefits for them through the acquisition of Besolo. Lettuce has focused much of its attention on higher-earning independent professionals who are in a position to benefit from its offerings, according to Harpaz. Recent research by MBO Partners found that the number of self-employed professionals earning $100,000 or more increased by 53% since 2020 to 5.6 million. MORE FOR YOU Lettuce aims to bring solopreneurs the same quality of benefits as those available through large companies, Harpaz said. Through the acquisition of Besolo, Lettuce aims to introduce the type of health plans typically available through larger employers as early as Q1 2026, Harpaz said. “Many of our customers do not have a great solution for healthcare,” he said. Many have said they are disappointed by the options available to them through the marketplaces, he said. Besolo’s founders will be joining Lettuce’s team following the acquisition. “Lettuce has built an incredible fintech solution that makes it easy for solopreneurs to run their businesses,” said Mark Jackson, co-founder and CEO of Besolo, in a statement. “The leadership team clearly understands the unique challenges solo businesses face and shares our commitment to serving this community. We couldn't be more excited to join the Lettuce team as the company expands into healthcare.” Lettuce offers a subscription-based platform for solo professionals with three tiers: one aimed at solopreneurs making $40,000 to $69,000; one targeting solopreneurs making $70,000 and up, with features such as automated S Corp accounting; and a premium product for complex businesses with employees. The company says its AI technology has been trained to understand the U.S. tax system and S-Corp compliance. Lettuce is currently rolling out upgrades to LettuceHead AI, an AI-powered knowledge base and tax hub that answers tax and accounting questions for solopreneurs, said Harpaz. Among them is a voice-powered interface to streamline workflow. Lettuce is also expanding its retirement offerings with comprehensive guidance on solo 401(k) and SEP IRA options. Subscribers currently have access to options such a solo 401(k) through Carry, another fintech startup. Under an enhanced feature, Lettuce will provide multiple plans and “bring-your-own” options, detailed plan comparisons, real-time insights on tax implications and transaction classifications. Lettuce will host the Solo Summit, a virtual all-day community event focused on growth strategies and annual planning for one-person businesses, on November 6, where I'll be a volunteer moderator for a panel on multi-channel marketing. In the coming months, Lettuce will be looking to build its presence in communities of solopreneurs, such as therapists, attorneys, physicians, and engineers, through events and by working with freelance platforms as distribution partners, Harpaz said. “A big chunk of our focus will be finding professional solos where they already congregate,” he said. Editorial StandardsReprints & Permissions
