Guideline vs Cash App
Side-by-side comparison of AI visibility scores, market position, and capabilities
Founded 2015; raised $356M; $1.15B valuation (2022); $120M ARR; $13B AUM; 50K+ business clients; acquired by Gusto ~$600M (Nov 2025).
About
Guideline is a technology-driven 401(k) plan provider founded in 2015 by Kevin Busque (co-founder of TaskRabbit), headquartered in San Mateo, CA. The company set out to democratize retirement savings by making professionally managed, low-cost 401(k) plans accessible to small and medium-sized businesses — a segment historically underserved by legacy providers like Fidelity and Vanguard due to high complexity and fees. Guideline's platform automates plan setup, payroll integration, compliance filing, and employee investment management, charging a transparent subscription fee ($49–$129/month plus $8/participant) and a low 0.08% annual AUM fee, compared to the industry-standard 1–2% charged by incumbents.
Block Inc. (NYSE: SQ) digital banking at 57M MAU generating $16.25B 2024 revenue (half of Block); Bitcoin trading 62% of revenue with Moneybot AI and Lightning Network competing with Venmo and Chime for Gen Z financial services.
About
Cash App is a San Francisco, California-based digital banking and payments platform — operated by Block, Inc. (NYSE: SQ, formerly Square) — providing 57 million monthly active users with a comprehensive mobile financial services ecosystem including peer-to-peer payments, Cash App Card debit card (24 million users), Bitcoin and fractional stock investing, direct deposit banking, tax filing, and personal loans. In 2024, Cash App generated $16.25 billion in revenue (13.2% year-over-year growth) and processed $282.9 billion in customer inflows — representing half of Block's total revenue with Bitcoin trading comprising 62% of Cash App's revenue stream. Cash App's AI expansion includes Moneybot (an AI-powered financial navigation assistant) and Bitcoin Lightning Network payments using USD balance, with stablecoin support in development. Launched in October 2013 as "Square Cash" by Jack Dorsey and Brian Grassadonia.
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