Aug 7, 2013 · 4 minutes

Sean Parker has added his name to the list of investors putting money into WillCall, a bookings app that focuses on live music and lets people buy tickets to shows with one click. The San Francisco-based startup announced today that it has raised another $1.2 million, bringing its total raise to date to $2.1 million.

The controversial Parker -- who founded Napster, helped get Facebook off the ground, is an investor in Spotify, and now specializes in media-piquing weddings -- is the most prominent new name to get behind WillCall. But the startup revealed today that it is also taking money from music industry figures Coran Capshaw, founder of Red Light Management and ATO Records, and John Frankenheim, an entertainment lawyer. SV Angel, Airbnb co-founder Joe Gebbia, and Bruce Flohr, another music industry veteran, also took part in the round.

The new cash injection comes just a month after WillCall released Version 2 of its app, which extended its utility from recommendations and bookings service to ecommerce. What’s most interesting about the new version of the app is not its core functionality – providing information on upcoming shows in your city (only available for San Francisco and New York right now, with Los Angeles coming soon) – but that it gives artists new ways to make money: through tips and online merchandise sales.

As highlighted by Thome Yorke’s recent outburst against Spotify, there has been much consternation about the effect music-streaming apps are having on the ability of new artists to make money. Spotify proponents say the service exposes more people to more music, and therefore also helps get people along to live shows, but detractors say the pennies such services pay for streaming will never compensate for lost revenue from album sales. (For more details, read PandoDaily’s in-depth explainer on the havoc digital has wreaked on the music industry.)

Live shows, then are increasingly crucial to bands’ bottom lines. Not only does WillCall want to help get more people along to gigs, but it’s also attempting to use its payments service for transactions beyond just ticket sales. The tipping feature, for instance, lets gig-goers throw their favorite artists a few more dollars right from their phones while they’re actually at the shows. That might sound like a hard sell for people who have already paid to get into a show, but if the cover charge was only $7 and it’s for an indie band that is struggling to get by, I bet plenty of people (me included) would be willing to pay a little more. (It reminds me of a freelance journalist friend of mine who sought tips for a scoop that he published on a blog and earned so much from such donations that he briefly became the highest-paid journalist in New Zealand.)

The tipping feature is limited to only a few venues for now, but it has potential. At some point, WillCall plans to share with artists the email addresses of the people who tipped them, which lets the musicians better cultivate, and engage with, their fanbases. WillCall founder Donnie Dinch also envisages a time in the not-too-distant future in which bands could have an iPad on stage that shows them when tips come in from the audience in real-time.

Dinch says the tipping feature came out of a whiskey-fueled brainstorming session at the startup. He and his colleagues thought it strange that you could go to a gig and tip the barman and the coat check person, but that there was usually no way to tip the band that you came to see.

The merch-sales play also has value. For indie bands, the merch tables stacked with CDs and T-shirts at their gigs have always been a key source of income. Streaming music services have taken away some of that value because many gig-goers or new fans can now just add the albums to their Spotify playlists, meaning they don’t need to buy a CD. By letting people buy merch through an app that will have the goods shipped to them later, they then don’t need to worry about having to lug posters or T-shirts around with them for the rest of the night. Not having to have cash on hand is also a bonus.

WillCall clearly has some good ideas, and now the big-name support to help it take its app to the next level, but it faces many uncertainties. Scaling will be its biggest challenge – working with disaparate and sometimes disorganized venues across many cities will be a headache to say the least.

It will also continue to face off against not only apps such as ThrillCall (similar name, but it got to the space years earlier than WillCall) and Timbre, but also against listings guides such as Time Out, New York magazine, and the alt-weeklies, all of whom are adapting for mobile and already have the deep relationships (with venues, promoters, and bands) on which the music industry is predicated. And lots of music fans take pleasure in the research aspect of finding gigs to go to or discovering bands, so it’s not obvious that everyone will take to a recommendations app with alacrity.

What so far sets WillCall apart, however, is its determination to help musicians and venues make money. In that way, it recognizes the value in cooperating rather than disrupting. Adding Sean Parker as an investor into its mix, then, promises to be a fascinating dynamic. With his track record with the music industry – first disrupting it with Napster, now trying to make nice through Spotify – WillCall may ultimately consider his investment a turning point for its business.

The question is, which way is it going to turn?