Otherside AI
Melville, US · Founded 2020 · Delaware corporation · 3 known investors
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HyperWrite is an AI writing assistant available as a Chrome extension that provides autocomplete, web search, and citation capabilities to help users write, edit, and refine text. It serves writers, academics, and professionals seeking AI-powered assistance with content creation and research.
Also known as HyperWrite · OthersideAI
Founders & leadership
Otherside AI was founded in 2020 by Jason Kuperberg and Matt Shumer.
Investors · 3
Reported raises · per SEC filings
Form D private placements$2.3M disclosed across 1 round · 2020
▶$2.3MraisedNov 2020 · 13 investors · Other TechnologyRule 506(b)
- Miles FeldsteinDirector
- Matthew ShumerExecutive Officer, Director
- Offering amount
- $2.7M
- Amount sold
- $2.3M
- First sale
- Nov 2020
- Incorporated
- Corporation, Delaware, 2020
- Federal exemptions
- 06b
Source: SEC EDGAR Form D. Amounts as filed; amended filings shown once at their latest values.
Company profile
researched Aug 2026Otherside AI develops HyperWrite, a predictive AI writing assistant delivered primarily as a Chrome extension and accompanying web application. Core features include AutoWrite, which generates paragraphs on a given topic; TypeAhead, which supplies personalized, context-aware sentence completions and suggestions as the user types inside applications such as Gmail and Google Docs; an Email Responder that expands a few words into a full reply; HyperChat for conversational assistance, research and problem solving; and an AI document editor for collaborative writing.
Beyond these core surfaces, the product exposes a library of hundreds of task-specific tools, among them a summarizer, content rewriter, AI text editor, AI speech writer, general AI writer, an "Explain Like I'm Five" simplifier, and Scholar AI, which searches scholarly articles and papers to return citation-backed, real-time results. Users can also build custom AI tools tailored to their own workflows and configure custom personas so that generated text matches their writing style. The company positions the assistant for writing, editing and polishing text as well as for automating repetitive browser and email workflows.
Business model
Direct-to-user software distributed as a browser extension and web app, monetized through recurring subscriptions rather than one-off purchases.
Tiered subscriptions with monthly and annual billing. The Premium plan is $19.99 per month, or $16 per month billed annually ($192 per year), and includes 250 AI messages per month, citations and real-time information, three custom personas, access to the tool library and unlimited TypeAheads. The Ultra plan is $44.99 per month, or $29 per month billed annually ($348 per year), and adds unlimited AI messages, ten custom personas and first access to experimental writing and agent features. Annual billing is marketed as a 20% saving.
Traction
The company's site presents user testimonials sourced from Google Reviews describing the extension's use for writing completion, email handling and workflow automation, and identifies Flexible AutoWrite as its most popular tool.
▸Full profile — technology, go-to-market
Technology
Generative AI writing models integrated into the browser, with context-aware sentence prediction, custom personas that adapt output to a user's style, retrieval of real-time web and scholarly sources for citation-backed answers, user-configurable custom tools, and agent-style features for automating multi-step workflows.
Go-to-market
Self-serve acquisition through the Chrome Web Store extension listing and the company website, with free entry points leading to paid Premium and Ultra subscription upgrades; user reviews are featured as social proof on the site.
Individual knowledge workers and professionals who write frequently, including writers, students and academic researchers, and people handling high volumes of email and repetitive browser-based workflows.
Compiled by commissioned research from 1 cited public sources — announcements, filings, and press listed under research sources below.
Key figures
latest reportedCompany-reported or press-reported figures, each dated to when it was claimed — not independently audited.
Legal entities · 1
corporate structure▸Research sources · 1
primary sources listed
- Otherside AIothersideai.com · web
1 public sources were cited for this profile; the first-party ones are listed here.
Frequently asked questions
- What does Otherside AI do?
- HyperWrite is an AI writing assistant Chrome extension offering autocomplete, drafting tools, chat and cited research.
- Who founded Otherside AI?
- Otherside AI was founded by Jason Kuperberg, Matt Shumer in 2020.
- Who are Otherside AI's investors?
- Otherside AI's investors include Founders, Madrona Venture Group, New York Venture Partners.
- How much funding has Otherside AI raised?
- Otherside AI has disclosed $2.3M raised across 1 round.
- Where is Otherside AI headquartered?
- Otherside AI is headquartered in Melville, US.