Ask Proxy Launches $29-a-Month AI Assistant for Baby Boomers via Text

3 articles · Updated · Tom's Guide · Aug 16

Ask Proxy launched on Aug. 4 as a text-message AI assistant aimed at baby boomers who want AI help without downloading an app or learning prompts.
Users start by texting “Start” to Proxy’s phone number, then spend about 20 minutes sharing preferences; the service can also connect to calendars, accept photos and voice notes, and answer everyday requests.
Its main differentiator is proactive outreach: Proxy can text first with reminders, planning suggestions and conversation prompts based on personal details, past chats and calendar information.
The service includes 15 free messages, then costs $29 a month for unlimited use; the company says it does not sell personal data or use chats to train public AI models, though users are still urged not to share sensitive information.
Proxy enters a crowded AI assistant market dominated by ChatGPT, Claude and Gemini, betting that familiar SMS simplicity will win over older adults who find app-based AI cumbersome.