Lettuce Financial Secures $28M and Acquires Healthcare Benefits Startup Besolo to Expand its AI-Powered Operating System for Solopreneurs – Yahoo Finance
Expansion represents key milestone in the company’s vision to simplify how businesses of one operate; Lettuce also introduces more retirement savings options and enhancements to its AI-powered operating system with new voice interface
SAN FRANCISCO, Nov. 4, 2025 /PRNewswire/ — Lettuce Financial, the fintech platform built for solopreneurs, today announced it has secured $28 million in new funding to accelerate the expansion of its AI-powered operating system, designed exclusively for growth-focused one-person businesses seeking the same advantages as larger companies. The company also announced the acquisition of benefits access startup Besolo, a move designed to add quality healthcare choices to Lettuce’s suite of financial tools.
The funding was led by existing investor Zeev Ventures and will be used to drive the continued development and expansion of Lettuce’s suite of offerings as well as accelerate go-to-market strategies. Besolo’s founders will join Lettuce to lead its healthcare initiative. Lettuce is also bringing on Molly Loftus, former Cigna executive, Chief Actuary at Mercer, and CEO of Consortium Healthplans, as an advisor.
The announcement comes as the solo economy continues to surge. Nearly 50% of the U.S. workforce is expected to freelance by 2027, and the number of solopreneurs earning $100,000+ has grown to 5.6 million, nearly doubling since 2020. Despite its growth, this segment of the workforce remains underserved when it comes to tax, retirement, and healthcare benefits.
Millions of professionals, including doctors, therapists, consultants, creators, and fractional executives, operate as one-person businesses while being forced to cobble together the business and finance tools intended for big teams or individual consumers. Lettuce’s soloOS replaces those fragmented solutions with a single, intelligent platform where solopreneurs are able to manage their core business functions intelligently and with hyper efficiency.
The platform acts as a dedicated finance expert, eliminating the need for solopreneurs to become one. Its AI has been trained to understand the nuances and complexities of the U.S. tax system and S-Corp compliance to deliver tax strategies and savings, simplified payroll, expense management, banking, invoicing, accounting, and more – all through a secure, unified platform. Everything is logged, auditable, and built for U.S. tax complexity, including automated tax categorization and savings strategies, simplified owner payroll, and S-Corp compliance. With the Besolo acquisition, customers will also have access to better quality healthcare coverage and premiums, previously unavailable to solo businesses.
In addition, Lettuce is expanding its retirement offerings with comprehensive guidance on Solo 401(k) and SEP IRA options, one of the largest tax-saving opportunities available to solo business owners. The enhanced feature provides multiple plan choices through Lettuce or bring-your-own options, detailed plan comparisons including pros and cons, as well as real-time insights on tax implications and transaction classifications.
“The solo economy represents one of the fastest-growing segments of the American workforce, yet these professionals remain dramatically underserved,” said Ran Harpaz, founder and CEO of Lettuce. “We’re committed to leveling the playing field so growth-oriented solopreneurs receive the same operational efficiencies and advantages that have always benefited larger companies – from accounting and tax solutions to healthcare benefits and retirement savings options. Our integrated technology stack gives businesses of one the same level of benefits awarded to companies with many employees so solopreneurs can focus on growth strategy rather than administrative complexity.”
“Lettuce has built an incredible fintech solution that makes it easy for solopreneurs to run their businesses. 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,” said Mark Jackson, co-founder and CEO of Besolo.
Lettuce is also rolling out significant upgrades to its LettuceHead AI, an AI-powered knowledge base and tax hub built to help solopreneurs get real-time answers to their most common tax and accounting questions. The upgrades include the introduction of a voice interface that enables solopreneurs to manage their business operations conversationally, further streamlining workflow and accessibility.
“As a company that’s focused on and committed to high-earning solopreneurs, we’ve built a comprehensive operating system that takes care of their unique needs, end to end, not just the payroll, not just the banking, not just the taxes, not just the retirement, not just the healthcare. We’re the only ones doing that,” Harpaz added.
To reinforce the company’s commitment to helping solopreneurs operate and grow their businesses, Lettuce is hosting its second Solo Summit on November 6th, a free, virtual all-day event designed for solopreneurs and featuring expert-led sessions on growth strategies, annual planning, and personalized guidance. Over 3,000 solopreneurs are expected. Register to attend here.
About Lettuce Financial Lettuce Financial is the fintech platform built for solopreneurs, giving businesses of one the corporate-level advantages traditionally reserved for companies with many employees. Powered by AI, the platform provides a secure operating system that streamlines business operations and financial strategies, including accounting, payroll, benefits, and tax compliance. By handling the complexities of business management, Lettuce gives solopreneurs peace of mind and the financial edge to run and grow smarter, more profitable businesses.
