Short answer: Ask Proxy: A personal AI assistant you text like a friend: it learns your stage of life, location and priorities, draws on curated expert guidance and live web search, answers with one clear next step and texts you first before birthdays, trips and busy seasons. Kiwi: A proactive AI assistant you text on iMessage or WhatsApp: it keeps track of your trips, plans, bills and the people in them, texts you first when something needs doing, and books, orders or replies on any app or website once you say yes.
Ask Proxy vs Kiwi
Sourced facts only. “Unknown” means not verified yet.
Key facts side by side
| Criterion | Ask Proxy | Kiwi |
|---|---|---|
| Type | personal agent | personal agent |
| Vendor | Peacock Parent, Inc. (San Diego; founder and CEO Christine Landis) | The Nudge L.L.C-FZ (Meydan Free Zone, Dubai, UAE); built by Aneesh Modi |
| Channels / category | Text message: save (820) 732-2625 and text START; texts, voice memos and screenshots | A contact in Messages on iPhone or in WhatsApp on any phone; your phone number is your account; web account at app.heykiwi.co |
| Pricing / availability | USD 29/month billed annually (USD 348/year) or USD 39/month month-to-month, with your first 30 texts free (per askproxy.com, 3 Nov 2026). Work plans from USD 15 to 23 per employee per month | Free to use (USD 0): no subscription, trial or card to start; you pay companies directly for anything Kiwi books (per heykiwi.co, 12 Oct 2026). Product Hunt listing says free during the pilot |
| Launched | 2026-10-15 | 2026-10-26 |
| Funding (reported) | Unknown | Unknown |
| Channels confirmed | SMS/text | iMessage, WhatsApp |
| Verified facts | Announced 15 Oct 2026 in San Diego by Peacock Parent, Inc. as a personal AI assistant by text built to carry the mental load; No app: text START to (820) 732-2625; accepts texts, voice memos and screenshots; Each reply combines your profile, past conversations, a private knowledge base, curated expert guidance and real-time Google search into one recommendation, in about a minute; Reaches out first, for example a gift idea a week before a birthday party or a packing list two days before a trip; Personal plans: USD 29/month billed annually (USD 348/year) or USD 39/month; first 30 texts free; No ads or paid placements; data not sold and conversations not used to train public AI models; Work version priced from USD 15 per employee per month for large companies and USD 23 for teams under 49 people; Available in the United States and Canada | Texts you first: flight delays, a free Saturday, a parcel that needs a signature, bills due, and a morning brief of your day; Does things on any app or website when you say yes; anything that costs money or messages someone waits for your yes and shows its price first; No app to install: a contact in Messages on iPhone or WhatsApp on any phone; your number is your account, with no password; Connect Gmail or Google Calendar by asking in the chat; works with apps like Gmail, Outlook, Google Calendar, Slack, Spotify and Uber; Free to use with no subscription, trial or card to start; no ads, data never sold, no business can pay to change suggestions; Doesn't keep copies of your email and calendar; saved sign-ins are encrypted (AES-256-GCM) and never shown to the AI; Featured on Product Hunt on 26 Oct 2026, finishing #11 of the day with 110 upvotes; Operated by The Nudge L.L.C-FZ, registered in the Meydan Free Zone, Dubai; users must be 18+; terms updated 28 Oct 2026 |
| Website | https://askproxy.com/ | https://heykiwi.co/ |
| Sources | [1] [2] [3] [4] | [1] [2] [3] [4] [5] [6] |
| Last checked | 2026-11-11 | 2026-11-11 |
Frequently asked questions
What is Ask Proxy?
A personal AI assistant you text like a friend: it learns your stage of life, location and priorities, draws on curated expert guidance and live web search, answers with one clear next step and texts you first before birthdays, trips and busy seasons.
What is Kiwi?
A proactive AI assistant you text on iMessage or WhatsApp: it keeps track of your trips, plans, bills and the people in them, texts you first when something needs doing, and books, orders or replies on any app or website once you say yes.
How much does Ask Proxy cost?
USD 29/month billed annually (USD 348/year) or USD 39/month month-to-month, with your first 30 texts free (per askproxy.com, 3 Nov 2026). Work plans from USD 15 to 23 per employee per month
How much does Kiwi cost?
Free to use (USD 0): no subscription, trial or card to start; you pay companies directly for anything Kiwi books (per heykiwi.co, 12 Oct 2026). Product Hunt listing says free during the pilot
Are Ask Proxy and Kiwi the same type of agent?
Ask Proxy is listed as a personal agent and Kiwi as a personal agent.
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