The founding story, 1999
In late summer 1999, as the first staff came on board, Sean Fenlon opened the company’s Employee Handbook with a letter telling how ListenSmart.com began. Here it is in his words.
The letter, “Sean’s Welcome”, opens the ListenSmart.com, LLC Employee Handbook, written in late summer 1999, just after the company was formed in August. The excerpts below are verbatim, spelling and all; “…” marks a cut. The headings are the letter’s own.
The Story
I have been a musician since I was eight years old. I began playing the saxophone in grade school, switched to the bassoon in high school, and picked up piano in college where I also began composing, arranging, and songwriting. While working on a Masters Degree and Doctorate Degree at The Peabody Institute of Music in downtown Baltimore, I spent a considerable amount of time in their Electronic & Computer Music Department where I developed a close association with digital audio.
Note, 2026: Sean switched to the bassoon in middle school, not high school as the 1999 letter has it (Sean P. Fenlon, 2026).
Two people from those years became part of the company. Sean met David Seidl while working part-time at Gramophone, a Baltimore hi-fi and home-theater shop (“Dave was a customer and mine, but we hit it off great on a personal level from the get go”), and Marc Contract at Investors Mortgage Corporation, where Sean worked for two years and rose to Manager and Partner (Sean P. Fenlon, 2026).
Although it was announced that I left the company to finish the work on my Doctoral Dissertation, I actually used the free time to formulate the vision and business plan of ListenSmart.com. For the six months leading up to beginning the plan, I felt as though I was on the “cutting edge” of technology as an independent musician. I was one of the first generation of musicians to convert my music into MP3 song files and willingly upload them to web sites so that they may be downloaded by anyone in the world for free. To find new listeners for my rather non-mainstream music was a huge thrill, but the honeymoon quickly faded.
I quickly saw an emerging trend of companies inviting independent artists to post their music on their web sites with the promise of “exposure & promotion.” However, the reality of the situation was that the artists provided desirable content that drove visitors to the web sites and the web sites were earning significant revenues based on advertising from the traffic, but without sharing those revenues with the artists… the ones that made the traffic and the revenues possible!
He left the mortgage company in May 1999.
The Plan
Thus, the cornerstone of the business plan for ListenSmart.com was to create a business model whereby the artists would share the revenues generated by the site 50/50. Another fundamental key was to create more sophisticated filtration technologies to allow a listener a better chance at finding the music they are much more likely to enjoy.
So I began writing the 80-page business plan. I had been sharing my vision for months with Marc Contract (even while still with the mortgage company) who clearly saw the potential and wanted to be part of the startup.
That plan is summarized on The first business plan, 1999.
The Team
His reading said investors would want a complete management team, so he needed someone to lead the technical side. Investors Mortgage had just called in Brandon Pepelea and his company, Designers Dream, to cover its IT:
Marc Contract reported to me that he was stunned by Brandon’s technical capacity and I also heard 2nd hand of his ability to figure out all of the “customizations” that I had left behind… within minutes! … I scheduled a meeting between Marc, Brandon, and myself to discuss his interest. Brandon too saw the potential and agreed to join the team. Brandon’s experience in web development, networking, and connectivity from his consulting company, his time at PSI Net, and his early years in the U.S. Marine Corp made his the perfect leader for our project.
Now, we just needed some money!
The Money
I actually began trying to raise startup capital by posting a very brief description of my idea on a web site devoted to Venture Capitalists looking for new projects to fund. The next day, I received two emails, a FAX, and phone call from four different investors. This freaked me out! I knew that I was unprepared to go about this process without advice and representation. I immediately thought of my old friend Dave Seidl from my days at the hi-fi stereo shop.
Dave, a corporate attorney and partner at the Baltimore law firm Miles & Stockbridge, agreed to represent the company and became “the ‘point man’ in terms of raising our startup capital.”
Within a few weeks, we had polished our business plan and given a presentation to eight investors. Every one of them wanted in and not one who heard our plan and our vision declined on the offer to invest. Thus, we raised $500,000 for the purposes of building a prototype website based on the plan we put forth.
The letter goes on to the hopes of the moment: a second round of $5–10 million once the prototype was built, then a public offering. Neither happened. The company raised $1 million in all, by its 2001 offering memo’s count, and wound down in 2001–02 (see what happened).
The Goal
Our goal over the next three months is to work at a feverish pace to build the website, infrastructure, and “virtual community” based on our plan and vision.
… Our entire project will only be as good as the efforts of our collective group and for that reason; we established a complete “open-door” communication policy regardless of the nature of the subject.
… Please pay special attention to the section on the competition. Although we feel far superior to any similar site implementation, we do want a deep understanding of the online music phenomenon from ALL of our team members. Visit their sites repeatedly. Use their features and functions and take note of what you like and what you do not like.
The competitors he meant are on The competition, 1999. The letter is signed “Sean P. Fenlon, President & C.E.O., ListenSmart.com, LLC”, with a postscript: “feel free to visit my personal web site @ www.seanfenlon.com”. It still works: seanfenlon.com.
Note, 2026: The letter calls David Seidl and Marc Contract “founding members” and Dave the “fourth founding member”. Sean Fenlon founded the company and is its only founder; the seven people of the 1999 founding team, with the titles Sean gives them, are on the Team page. A few weeks later the October 1999 investor report introduced the first technical hires and Sean’s brother, Ben Fenlon.
Source: ListenSmart.com, LLC Employee Handbook, “Sean’s Welcome” (The Story, The Plan, The Team, The Money, The Goal), 1999. The handbook mentions MP3.com’s late-July 1999 IPO and the presentation to eight investors (late August 1999, per the October 1999 investor report), which dates it to late summer 1999. The rest of the handbook reprints the 1999 business plan. Funding total: ListenSmart.com offering memo, 2001.