Bill Lennon
Co-founder and CEO
Privacy-focused family AI assistant for email, calendar, meals, appointments, and bills. It shuts down on November 6, 2026.

Ollie is a privacy-focused personal assistant for families, sold as a subscription. It connects to email and calendar, and it helps with meal planning, grocery shopping, to-dos, appointment booking, and bill payments, including through group chats. TechCrunch reported in September 2026 that it was among the first mainstream, family-focused assistants to reach SOC 2 compliance, an independent audit of controls for customer data.
The company says it does not ask for usernames or passwords. When a task needs a login or a payment, Ollie uses its own browser in the cloud and sends a link to a remote session. San Diego-based Ollie raised a $7.5 million seed round led by Khosla Ventures, with AI House also participating, according to that September coverage.
Co-founder and CEO Bill Lennon announced on October 30, 2026 that Ollie will shut down on November 6, 2026. He said the company got close but could not keep up once Muse, Instinct, and others entered the space, and that it became harder to stand out, grow, and raise the capital it needed. The farewell on ollie.ai says Ollie will text an export of a user's data, which they can share with another personal assistant.
Billing for Ollie and for Ollie for Meals is canceled, and subscribers receive a refund for any partial or unused months. Questions go to hello@ollie.ai. Sources: https://ollie.ai/farewell/ ; https://techcrunch.com/2026/10/30/ollie-a-privacy-focused-ai-assistant-is-shutting-down/ ; https://techcrunch.com/2026/09/03/ollie-is-betting-privacy-can-win-the-ai-assistant-race/
Pricing: Subscription. The farewell names Ollie and a separate Ollie for Meals subscription. The sources checked do not list a price. Checked October 31, 2026.
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