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Justin Frankel started Winamp in 1997 and sold it to AOL in 1999. They had no VC funding and had just two developers. It was funded by users sending checks in mail because they really loved the revolutionary music player program for the revolutionary mp3 file format.
When we got a chance to talk to Justin, I was star struck. Holy llama, it's the man himself.
Here are a few things that stood out to me from the conversation.
Justin was not afraid of tongue-in-cheek naming
The company's name was Nullsoft, which "was just a play on that being non-existent, because Microsoft was this massive company making massive Windows 95." If Microsoft was "micro," Nullsoft was nothing.
Justin embedded his own sense of humor into the application
When a user installed Winamp, the program played the "Winamp, it really whips the llama's ass" audio clip, which Justin thought was funny. It's a quote from Wesley Willis' "Whip the Llama's Ass" song. In the age of faceless, boring software, that was unusual.
Justin shared his work publicly and listened to users
For example, Winamp skins were created in response of users embedding their own image assets by hacking into the Winamp executable. With each upgrade, users had to patch the .exe once again, so Justin turned Winamp into a platform that supported skins and plugins. Skins became the signature feature of Winamp and brought in ad revenue from the skins catalog website.
Post-acquisition, Justin stuck around AOL for a few years
He cared about the product and didn't want Winamp to be ruined. People were saying "you can't give a 20-year old a bunch of money and expect them to stick around," and Justin's response to them was "F.U., I'm gonna be here." Justin says that he should've bought Winamp back from AOL and open-sourced it when he had a chance.
Oops, he did it again
In 2006, Justin released the first version of the digital audio workstation software REAPER, which is as powerful as ProTools, Logic and other tools produced by the industry's behemoths but costs only a fraction of their price. REAPER is cross-platform and is built by a team of just 2 people (with occasional contribution of another person). I've used REAPER for years and use it to produce our podcasts.
Zero marginal cost of distribution
One of the primary reasons Justin is able to pull off massive hits with small teams is that he has no backend infrastructure. The software runs on end users' machines and there's no ongoing maintenance cost. The marginal cost of each extra installation is effectively zero.
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Segments
[03:16] The genesis of Winamp
[11:07] Winamp whips the llama's ass
[14:06] Nullsoft
[16:27] Winamp as a platform
[23:16] The business side of Winamp
[24:11] What was it like to work at AOL?
[27:06] Why Justin doesn't use streaming services
[30:03] Justin's website
[32:06] Why Justin created Reaper
[35:48] Shipping v1 of Reaper
[37:02] Reaper is built by just a few people
[38:53] Cross-platform codebase
[40:48] Reaper as a platform
[43:42] Future of Reaper
[44:40] AI in Reaper
[47:09] Questions lightning round
[53:36] Book recommendations
Show notes
Where to find Justin
Books
Masters of Doom by David Kushner
Nona the Ninth by Tamsyn Muir
The Three-Body Problem by Cixin Liu
Catch-22 by Joseph Heller
Flatland: A Romance of Many Dimensions by Edwin A. Abbott
Podcasts
Software
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Ep.2: Justin Frankel, creator of Winamp and Reaper