OthersideAI's 23-year-old CEO launches HyperWrite AI butler after $2.8M round

Long Island-based OthersideAI, led by 23-year-old co-founder and CEO Matt Shumer, has closed $2.8 million in fresh funding from Madrona Venture Group and Active Venture Partners, bringing total funding to $5.4 million and an implied valuation of about $50 million. The seven-person startup, which began in Shumer's parents' home in 2020, already boasts over 1 million users and millions in revenue. Its flagship product, HyperWrite, an AI-powered Chrome extension launched before ChatGPT, helps users draft emails, expand bullet points, summarize texts, and adjust writing style.

Now OthersideAI is rolling out a more ambitious feature: a personal assistant that turns the browser into a "digital butler." In a limited test, the AI can organize Gmail, draft responses, book flights, order a pizza, and find LinkedIn candidates. But Shumer acknowledges the system makes mistakes and could go haywire with real transactions. To mitigate risk, OthersideAI is monitoring early testers and building guardrails, including a verification step for credit card purchases. "We could roll this out faster... but my view is that it's not the right thing for society," Shumer said. The cautious rollout reflects broader concerns about AI reliability, as experts like Stony Brook's Niranjan Balasubramanian note that large-language models often stumble on multi-step tasks.