WireOver
DefunctYC W12Boston, US · 2 employees · 6 known investors
WireOver is a desktop application using peer-to-peer technology to enable secure, encrypted file transfers between users. The service supports unlimited file sizes and offers both free and premium tiers with enhanced security features.
Also known as WireOver
Founders & leadership· Y Combinator alumni (W12)
Investors · 6
Also in the syndicate · 2
Company profile
researched Aug 2026WireOver developed a cross-platform desktop application (Mac, Windows and Linux) for sending large files directly between users over peer-to-peer connections. Users dragged files into the application window and entered the recipient's email address; once the recipient had the client installed and running, the transfer occurred peer-to-peer or was routed through WireOver's servers without being stored there. Because no files were retained on servers, the company offered unlimited file-size transfers at no cost, positioning the product for use cases such as multi-gigabyte video files and large photo collections.
A paid Pro tier added end-to-end encryption, under which files were encrypted before leaving the sender's machine and could only be decrypted by the recipient, including when the recipient was not a paying subscriber. The company described its posture as "trust no one," contrasting it with cloud storage providers that decrypt files on their servers and control the re-encryption keys. Additional security features included the ability to verify the recipient machine's cryptographic fingerprint to guard against man-in-the-middle attacks. A structural limitation of the transfer-based model was that sender and recipient had to be online simultaneously, unlike link-based cloud sharing.
Founding story
Sources state the company was founded in 2011 by Trenton (Trent) Ashburn, who had built computational models for quantitative hedge funds and later raced as a semi-pro cyclist before seeking a company idea he could relate to; he identified the difficulty of sending large files securely and the fact that mainstream providers decrypt files on their own servers. Amit Bansil, a Boston-based programmer, is also listed as founder and CPO.
Business model
Freemium desktop software: unlimited-size unencrypted transfers offered free of charge, with a paid subscription unlocking end-to-end encrypted "Secure" transfers. Because files were never stored on company servers, storage costs did not scale with free usage.
Subscription revenue from Pro accounts priced at $10 per month for end-to-end encrypted transfers; unencrypted transfers were free.
Traction
Public reporting at launch described a four-person team and cited clients who had replaced physical media shipments with the service; no user or revenue figures are disclosed in the available sources. Databases list no known external funding and a current team size of two.
Latest developments
WireOver is listed as inactive in Y Combinator's company directory and in third-party startup databases; no recent product or funding activity appears in the available sources.
▸Full profile — market position, technology, go-to-market, history, risks & controversies
Market position
Positioned as an alternative to cloud storage and sync services such as Dropbox, Google Drive and SkyDrive for the specific task of sending large files securely, differentiating on unlimited free file size and low-cost end-to-end encryption rather than on storage or synchronization.
Combination of no server-side file storage, unlimited file size at no cost, end-to-end encryption available at a low monthly price that also worked when the recipient had no paid account, cryptographic fingerprint verification, cross-platform clients, and an email-address-only setup flow.
Technology
Peer-to-peer file transfer implemented in a Python-based desktop client after several discarded prototypes. Transfers ran directly between endpoints or were relayed by WireOver servers without server-side storage. Pro transfers used end-to-end encryption in which WireOver held no decryption keys, and users could verify recipient device cryptographic fingerprints.
Go-to-market
Individuals and businesses needing to move very large files, and privacy-conscious users with sensitive material; the TechCrunch account notes some clients moved to WireOver from shipping physical hard drives and USB drives by mail or courier.", "go_to_market">
History
Founded in 2011 and part of Y Combinator's Winter 2012 batch, WireOver emerged from stealth in January 2014 with its desktop client after building and discarding several prototypes. Y Combinator's directory and other databases now list the company as inactive with a team size of two. Founder Trenton Ashburn is described in a later founder profile as having gone on to other ventures, including Grok (2018), a Senior Data Scientist role at Concentric (2019), and Simpact, where he is CEO, co-founder and CTO.", "geographic_footprint">
Risks & controversies
Sources are inconsistent on funding: TechCrunch (2014) reports Y Combinator funding from Andreessen Horowitz, SV Angel and Yuri Milner plus an additional seed round from Bessemer Venture Partners, .406 Ventures and angel investors including Hayes Metzger, while later database listings show $0 raised and no known external funding. Product-level limitations noted at launch include the requirement that both parties be online simultaneously. The company is no longer listed as operating.
Compiled by commissioned research from 8 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.
Timeline · 3
launches, deals, and filingsY Combinator's company directory and third-party startup databases list WireOver's status as inactive.
The Y Combinator startup publicly launched a desktop application allowing free transfers of files of any size, with an optional $10/month tier adding end-to-end encryption.
WireOver was part of Y Combinator's Winter 2012 batch.
Dated company events from announcements, filings, and press; legal rows summarize public dockets and regulator releases.
In the news
▸Research sources · 8
primary sources listed
- WireOver: Really secure file sending for big files. | Y Combinatorycombinator.com · web
8 public sources were cited for this profile; the first-party ones are listed here.
Frequently asked questions
- What does WireOver do?
- WireOver was a Y Combinator-backed desktop app for peer-to-peer transfer of unlimited-size files with optional end-to-end encryption.
- Who founded WireOver?
- WireOver was founded by Amit Bansil, Trenton Ashburn.
- Who are WireOver's investors?
- WireOver's investors include Y Combinator, Andreessen Horowitz, Bessemer Venture Partners, SV Angel.
- Where is WireOver headquartered?
- WireOver is headquartered in Boston, US.

