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Rippling's New Data Cloud Parker Conrad, CEO of Rippling, aims to revolutionize how companies approach data analytics by integrating it directly into human capital management systems. This strategic move positions Rippling to compete with specialized business intelligence tools. The Problem with Current Data Stacks The modern data stack is often a patchwork of tools from multiple vendors, including data integration, storage, querying, transformation, and visualization layers. Conrad argues that Rippling can consolidate this into one system, with the added benefit of built-in organizational context. Rippling Data Cloud in Action Rippling Data Cloud provides insights into employee productivity and AI spend. Example: An employee using Claude for $30,000 a year, with questionable ROI. Live dashboards analyze compensation reviews, support ticket volumes, and employee scheduling. Optimizing AI Token Spend Rippling's AI analyzes which engineers get value from AI tools and which don't. Engineers with high spend and low performance flagged for review. Rippling has cut spending limits for certain employees based on this analysis. Business Impact and Future Plans New revenue from Rippling Data Cloud runs at $5-7 million a month. About 560 companies currently use the product. Rippling also launched Business Banking for high-yield checking and same-day payroll processing. The Road Ahead Conrad emphasizes no rush for an IPO, focusing on growth and product development. Rippling spends 45-50% of its revenue on R&D;, significantly higher than public-market HR companies.

The Controversial Bet on AI BookkeepingDespite the collapse of his previous startup, Ian Crosby is taking another shot at building a business out of automating bookkeeping. His new venture, Synthetic, aims to create a fully autonomous AI bookkeeper that can generate accrual-based financials without direct human involvement.The Vision Behind SyntheticSynthetic is designed to revolutionize bookkeeping by eliminating the need for human accountants, a stark contrast to current accounting startups like Xero. Crosby maintains an all-or-nothing approach: "We're not going to release anything that's not fully autonomous. It's that or bust."The startup is currently in the design phase, with Crosby acknowledging that his vision may not yet be technologically possible. The company plans to initially serve only AI and other software startups.The $10 Million InvestmentDespite the challenges and Crosby's troubled past with Bench Accounting, Synthetic has successfully raised $10 million in a Seed funding round led by Khosla Ventures. The round also saw participation from Basis Set Ventures and Shopify CEO Tobias Lütke.This financial backing provides Crosby with the resources to wait for foundational AI models to become more reliable for bookkeeping calculations. "I've raised years of cash, so we can just wait it out," Crosby stated.Learning from Past FailuresKhosla partner Jon Chu defended the investment by explaining his tendency to "run towards controversy a little bit." He cited Parker Conrad's journey from Zenefits to founding Rippling (now valued at $17 billion) as an example of how industry narratives can be misleading.Chu conducted thorough due diligence, speaking with several executives who worked with Crosby after his departure from Bench. According to Chu, they "had fantastic things to say about Ian." This feedback, combined with Crosby's subsequent roles at Shopify and founding of Teal (which was acquired by Mercury), convinced Khosla of his growth potential.The Bench Accounting FalloutCrosby's previous venture, Bench Accounting, famously shut down in 2024 before being "bought for scraps." Crosby maintains he wasn't directly responsible for bringing the company to insolvency, stating he was fired by Bench's board in 2021 after turning down a $250 million acquisition offer from Brex.The board reportedly disagreed with Crosby's strategic direction as the business was bleeding cash, and his executive team was frustrated with his direct leadership style. "He took a big swing, made a few mistakes. That didn't go well," Chu acknowledged about Crosby's tenure at Bench.The Path to Autonomous AI BookkeepingWhile Synthetic's prototype works for a narrow group of users, Crosby remains uncertain how it will scale for a broader customer base. He compared the current state of AI bookkeeping to "a self-driving car that can drive down one street versus the self-driving car that can drive down any street.""We haven't driven down enough streets to know if it's going to crash," Crosby explained, highlighting the technical challenges ahead. Despite these obstacles, the founder remains committed to his vision of a fully automated financial future.