History
An independent-music portal from Maryland, built around a simple idea: artists post their music free, listeners find it by taste, and the artists share in what the site earns.
Sean P. Fenlon (Founder & CEO) founded ListenSmart.com, LLC in 1999 and led a seven-person founding team; his brother Ben Fenlon, Head of Operations, was there from the start and looked after artists on the boards. The portal went live privately on March 1, 2000 and launched publicly the next day. It was most active through spring 2001, and Sean shut it down by 2002. Artists signed up, uploaded MP3s and built their own pages; the site converted each song into four streaming and download formats. Listeners searched by genre (from a guide of 660 genres), by region, by popularity chart and by taste (“What bands/artists do you like?”), rated and reviewed songs, and built free member pages. The bulletin boards and an avatar chat room made it a community.
A Learn section, written by doctoral students of the Peabody Institute and other writers, explained music theory, history, instruments and styles. Those articles are the core of the site today.
From the 1999 company files
- The founding story, 1999: how it started, in Sean’s own words from the Employee Handbook.
- The first business plan, 1999: free music, three levels for artists, and how the model changed by 2000.
- The competition, 1999: the 24 online-music sites the plan profiled, and what became of them.
- Investor report, October 1999: the office saga, the first hires and the rivals’ missteps.
Timeline
Sean Fenlon leaves Investors Mortgage Corporation in Columbia, Maryland, where he had risen to Manager and Partner, and starts writing the business plan for ListenSmart.com.
Source: Employee Handbook, “Sean’s Welcome”, 1999; Sean P. Fenlon, 2026 (title)The first business plan is finished: every song free to download, five “peripheral” revenue streams, three levels for artists (Promotion Only, Commerce Participation, Profit Sharing) and a $5 million ask. It profiles 24 competing sites. The first outline of the site divides it into three parts: Listen, Learn and Artists.
Source: Business plan, summer 1999; company planning files, July 1999The plan is presented to eight investors. “Every one of them wanted in,” Sean wrote, and the company raises $500,000 to build a prototype.
Source: Employee Handbook, 1999; investor report, October 1999ListenSmart.com, LLC is incorporated, with headquarters in Columbia, Maryland. Sean P. Fenlon, its founder, is CEO.
Source: Business plan, 2000Database requirements are written for member profiles, songs, login, favorites and friends, by Sonny Suri, a consultant to the company (the October 1999 investor report calls him the “lead” database expert).
Source: ListenSmart Database Requirements, September 6, 1999; Sean P. Fenlon, 2026 (title)The first investor report covers the search for an office (Parkside Building, Columbia), the first technical hires, Syed Zaidi and Sonny Suri, and a three-phase build: templates and functions, content, then beta testing. It also announces that Sean’s brother, Ben Fenlon, has joined the founding team; he becomes Head of Operations.
Source: Investor report, October 10, 1999; Sean P. Fenlon, 2026 (title)Sean Fenlon meets Jim Griffin and Paul Bandrowski at the MB-5 conference, then writes to Jim asking for his advice and, perhaps, a seat on the Board.
Source: Sean P. Fenlon, letter to Jim Griffin, October 1999Sean Fenlon attends Webnoize ’99 at the Century Plaza Hotel in Los Angeles, the online-music conference chaired by Ted Cohen, where he meets Scour co-founder Travis Kalanick.
Source: Sean P. Fenlon, 2017 and 2026; Webnoize Live programming page (Wayback Machine)ListenSmart.com goes live privately, a day early, to test everything before the public launch.
Source: Sean P. Fenlon, 2026Public launch, announced at a New York music expo in Manhattan. The site opens as a public beta, and the bulletin boards open the same day. Launch PR is by Gregory Communications of Philadelphia, the firm CDnow also used; the press kit features Sean Fenlon, Marc Contract and Brandon Pepelea.
Source: Sean P. Fenlon, 2026; first bulletin-board posts, March 2, 2000Webnoize, the online-music trade daily, covers myplay’s new partner program, which puts free MP3s from partner sites into myplay lockers. Webnoize tags the story ListenSmart.com.
Source: Webnoize (Wayback Machine)Sean Fenlon on the boards: “Since I am a musician, I have thought the entire business plan through as an artist.”
Source: Bulletin-board post, March 8, 2000The Baltimore Sun reports on the launch, the 50/50 artist model and plans for a searchable licensing database.
Source: The Baltimore SunThe business plan is dated, with screenshots of the site taken on the company’s staging servers.
Source: Business plan, 2000The Wayback Machine’s first capture of the production site.
Source: Wayback MachineSean Fenlon tells artists on the boards: “We currently have a staff of 10. Compare that to MP3.com with a staff of 264!”
Source: Bulletin-board post, April 15, 2000The beta music publishing contracts (two options), a primer on music publishing and the business model, and an FAQ are posted on the boards for artists to review, on the date Sean had promised. A Q&A follows on May 25. No contract was ever signed.
Source: Bulletin-board posts, May 19 and 25, 2000; Sean P. Fenlon, 2026Wired quotes Sean Fenlon at the MP3 Summit.
Source: WiredSomeone breaks into the bulletin-board control panel and sends a forged email to every registered board member. Sean Fenlon replies on the boards: “Be assured that ListenSmart.com will continue to operate on the web while we continue to search for solutions to implement a new business model for compensating artists.”
Source: Bulletin-board post, October 3, 2000After the spring dot-com crash, Napster dominates the headlines and online music freezes for investors. Venture capitalists pull their term sheets.
Source: Sean P. Fenlon, 2026Alexa ranks ListenSmart.com in the top 25,000 websites worldwide, with over 8,000 sites linking to it.
Source: Offering memo, 2001The company’s 2001 offering memo reports 1,000+ registered artists, 3,000+ members, 30,000+ unique visitors a month (peak 80,000+), 25,000+ bulletin-board posts and $1 million raised. Revenue is banner advertising only, under $10,000 a year; staff has gone from 15 to one.
Source: Offering memo, 2001Sean Fenlon on the boards: “It was one year ago today that ListenSmart.com was launched. Wow. What a difference a year can make.”
Source: Bulletin-board post, March 2, 2001The last archived bulletin-board posts. When the Wayback Machine looked again in October 2001, no forum had a post later than April 2001.
Source: Wayback Machine: forum index, October 19, 2001The last archived captures of the portal as the company ran it (October 25, 2001).
Source: Wayback MachineListenSmart.com is shut down. From August 2002 to January 2003 the servers answer the Internet Archive’s crawler with “authorization required.”
Source: Sean P. Fenlon, email to Jim Griffin, July 7, 2020 (“by 2002, I had shut down ListenSmart.com”); Wayback MachineThe address shows a copy of the old site again, later revised under different management, until May 2004. Where those captures preserve the original pages unchanged, this site uses them.
Source: Wayback MachineThe Learn articles are restored on ListenSmart.com as a WordPress site.
Source: ListenSmart.comListenSmart.com is rebuilt as a static site: the Learn articles plus the original portal, preserved.
Source: This site
Press
- The Baltimore Sun, March 27, 2000: “Pledging royalty treatment”
- Wired, June 20, 2000: “MP3 Must Be ‘A Better Drug’”. Sean Fenlon at the MP3 Summit: “What the Web does allow us to do is track every single song and every single download down to the last digit.”
- Baltimore Business Journal, April 3, 2000: “Singing a new tune on the Net” (Wayback Machine)
- Music Industry News Network: “ListenSmart.com Provides Dramatic New Way For Independent Artists To Build Their Careers Online And Off” (Wayback Machine)
- Webnoize, March 6, 2000: “Several Music Partners to Offer Free MP3s to Myplay Users,” on myplay’s partner program, tagged ListenSmart.com. Only the headline and summary survive (Wayback Machine).
- MusicDish.com (Wayback Machine)
What happened
The plan’s bet was music publishing and licensing: artists who chose revenue sharing would make ListenSmart.com their publisher song by song, and the company would license that catalog for film, TV and advertising through a sister site, SyncSmart.com. The consumer site was built and used, but the company was a pre-revenue startup, spending its seed money while it raised venture capital. After the dot-com crash in the spring of 2000, Napster dominated the headlines that summer and froze investment in online music. Venture capitalists pulled their term sheets, and the company ran out of money. By 2001 the company’s offering memo gave the reason as “Unable to continue to attract sufficient funding to pursue original business plan.” Staff went from 15 to one, the boards went quiet after April 2001, and by 2002 Sean had shut ListenSmart.com down and moved on to his next tech venture.
No music publishing contracts were ever signed, so ListenSmart.com never collected or paid any music publishing royalties. Revenue was minimal: banner advertising only, under $10,000 a year by the 2001 offering memo’s count.
Sources: ListenSmart.com offering memo, 2001; Sean P. Fenlon, email to Jim Griffin, July 7, 2020; Sean P. Fenlon, 2026; Wayback Machine captures of the forum index (October 19, 2001) and the servers in September 2002. Captures from 2003–04 show a copy of the site, later revised under different management.