Andrew Dreskin

Two live performers every person should experience? “Bruce Springsteen and U2,” says Dreskin, photographed Sept. 19 at Ticketfly in San Francisco. “I’ve more or less seen every tour from both for the last 25 years.”

Mathew Scott

As music industry trailblazers go, Andrew Dreskin stands in rarefied company, having pulled off two ticketing-business feats during his 25-year career. He co-founded TicketWeb, the first online ticketing platform, which was sold to Ticketmaster in 2000 for $35.2 million. Then, in October 2015, Ticketfly, a 2.0 version of Dreskin’s vision (for which he serves as co-founder/CEO, overseeing a staff of 208), was acquired by Internet radio giant Pandora for $450 million.

It’s a long way from New Orleans’ Tipitina’s, where the New Jersey native promoted his first show while at Tulane University. Post-college, Dreskin eventually landed at Bay Area-based indie label Beserkley Records (Greg Kihn Band, Jonathan Richman and The Modern Lovers), where he built the company’s website during the Internet’s infancy. Later, partnering with Rick Tyler, who was developing an online ticketing platform, TicketWeb was born, making its first sale in December 1995, 11 months before Ticketmaster.

Dreskin’s former TicketWeb associate Dan Teree would help launch Ticketfly in 2008, and early believers included Peter Shapiro of Brooklyn Bowl and Seth Hurwitz of Washington, D.C.’s 9:30 Club. As Ticketfly grew, securing exclusive contracts with such venues as Forest Hills Stadium in New York and The Troubadour in Los Angeles, it attracted $50 million in investment and the interest of Pandora, with its 80 million listeners, which saw its entree into live music -- with Dreskin at the helm.

Andrew Dreskin

Ticketfly’s first ticket was sold on June 1, 2009, to Lebowski Fest at Brooklyn Bowl. Mathew Scott

The 47-year-old father of two, who resides in San Francisco’s East Bay area with his wife, Dr. Maria Raven, marked the one-year anniversary of the Pandora acquisition with Billboard.

By 2008, selling services online was no longer a new concept. What made Ticketfly different?

Social media was just burgeoning and Dan and I had this notion that the company that best harnesses the fan as a marketing channel on behalf of venues and promoters will win. Secondly, it was unclear to us why ticketing was separate from the rest of the promoter’s technology. So we set out to create the first truly integrated system, where venues or promoters could enter data one time into our platform and it would populate their website, email newsletter, create a Facebook event, send tweets, create a ticketed event and so on.

Your early clients were small and scattered -- how tough was it to enter the marketplace and compete?

Every day you’re just trying to knock down pins. First there was Brooklyn Bowl and Pete Shapiro, who took an absolute flyer on Ticketfly: We did a handshake deal on the corner of Wythe and 11th Street in Williamsburg. He didn’t have a venue and we didn’t have software, and we decided that Brooklyn Bowl would be Ticketfly’s first client. Then it was 9:30 Club [in Washington, D.C.], then on and on, one after the other. 

How had your approach to outside investment changed from TicketWeb to Ticketfly?

We thought the best path for [Ticketfly] would be to build big and fast. TicketWeb raised venture capital, but mostly bootstrapped, and took a more measured approach. We figured if we’re going to do it again, we have to amp it up and move to the big leagues. So we raised $50 million in funding; we built reserved seating and lots of interesting technology like a fan CRM [customer relationship management] tool; and Pulse, one of the first mobile apps for promoters to manage their ticket inventory.

Andrew Dreskin

Deal toys from both the TicketWeb and Ticketfly acquisitions include a bobblehead of promoter Dan Steinberg, an invitation to Seth Hurwitz’s 50th birthday party and a 9:30 Club cupcake. Mathew Scott

Were there other opportunities to sell before Pandora?

We’ve received numerous acquisition proposals through the years, but, prior to Pandora, it wasn’t the right time. I always believed that eventually the big tech companies and media properties are going to come looking for ticketing assets. You can aggregate a massive audience for streaming and recorded music, but where do you go from there?

You built a company valued at nearly a half-billion dollars. Did the price tag exceed your own expectations?

We told all prospective buyers [that] we have a vision ... to take this business public. When we sold TicketWeb, we had a negotiated exit there, and we wanted to do everything bigger, larger and different this time around. Frankly, it was a good and fair price. The business would have been worth more than that in the future, but [selling] was the right move for Ticketfly, the stockholders, our employees and Pandora.

A year after the acquisition, how are you feeling about the partnership’s progress?

It has greatly exceeded our expectations so far. These are very smart people at Pandora, and they have a very sophisticated strategy team -- they didn’t just do this willy-nilly. They did a lot of examination and testing before the acquisition, first with live streaming by webcasting Jack White from Madison Square Garden. Some 720,000 people created [a White] station to listen to that stream. They streamed a Mumford & Sons concert and a million people created a station. So clearly Pandora users were interested in live music.

Are there areas you haven’t yet explored?

There’s massive opportunity in sponsorship and advertising. We haven’t moved with any real purpose into that, but we think there’s a big business to be built there for Ticketfly in the U.S. Consider that Pandora, at its core, is about three things: music, data science and advertising. Pandora has 400 ad sales people.

Andrew Dreskin

Posters of shows held at Ticketfly client Forest Hills Stadium.Mathew Scott

Can you give an example of how a venue or festival can make use of Pandora to sell more tickets?

For instance, the Life Is Beautiful festival in Las Vegas. There’s a Life Is Beautiful station on Pandora that allows them to promote the festival and brand; There are artist audio messages detailing tour stops -- “Hey, Courtney Barnett is playing in Des Moines [Iowa], click here to buy tickets” -- that we and Pandora can insert in the listener flow. This is transformative stuff that’s never been done before and the future of how promoters are going to sell and market tickets going forward.

Many believe the holy grail in melding streaming and live is a “buy” button within the streaming app, where you don’t have to leave the site to buy tickets. Can that be done?

We’re in essence doing that now with the Pandora app. A fan can see the push notification or set a reminder for when the show goes on sale and they can instantly swipe and be brought into the purchase flow on Ticketfly. In 2017, we’ll have even deeper integration using the credit card on file.

Bots continue to be a topic of much debate in government and the public. How much time do you spend thinking about the secondary market?

We don’t have a big problem with bots. Through the years we’ve developed technology to identify what we call the bad actors. In the last five to 10 years, there has been a blurring of the lines between primary and secondary. The reticence of agents, managers, artists, promoters, venue owners and ticketing providers -- us included -- to effectively and efficiently price tickets at their true worth created the secondary market. Now it’s our job as technologists and stakeholders in the music ecosystem to take back the secondary market. In time, the primary and secondary providers will be one and the same.

You were a festival promoter, launching the short-lived Field Day as the East Coast Coachella. What went wrong?

Field Day was not meant to be. I loved the idea of melding a Burning Man-like event with a large-scale rock festival. The only problem was my competition in the market wasn’t really enthralled with me siphoning off theater and amphitheater acts. There were shenanigans behind the scenes, some funny business with our permits, and ultimately I had to take a two-day festival where we sold probably 35,000 tickets a day, 20,000 of them camping tickets, and trim that down to one day and move it to Giants Stadium. But I don’t consider Field Day a failure. I think of it as a valuable life lesson: that even a great idea that’s well-intentioned doesn’t always succeed. Sometimes external forces can be too difficult to overcome. Also, timing is everything. I was probably 10 years too early. It wasn’t the first time, and probably won’t be the last.

Andrew Dreskin

Reissued Cazals, the sunglasses of choice for ’80s hip-hop stars, and a photo of Dreskin with Richard Branson at the Virgin Festival (circa 1996).Mathew Scott

You’ve spent most of your adult life in the Bay Area. How have you seen the culture of San Francisco change since the tech boom starting driving real estate prices upward?

San Francisco is one of the most vibrant, dynamic cities in the world because it has always been full of transient people and continually transforms itself. Now is no different. You can’t stop progress. There are lots of great places to live around the Bay Area. Perhaps one benefit of the shift is that areas like Oakland are booming.

Do you see evidence of a disconnect between North and South California -- tech vs. creative?

There are actually a lot of similarities between the tech business up here and the media business in L.A. Both are progressive industries full of risk-takers. I think the two cities and cultures work pretty well together. If anything, we feel more kinship with our Southern California brethren than not.

Ticketfly did nearly $500 million in transactions in 2014. What growth rate do you anticipate going forward?

Ticketfly grows at roughly 25 percent year over year. Soon we’ll be in spitting distance of $100 million of fees revenue per year, so the business is building nicely. On average, roughly 40 percent of all tickets go unsold. For us that number is a bit lower, so we sell more of our tickets than the industry standard. But until every show is sold out, there’s still room for improvement.

A version of this article was originally published in the Oct. 8 issue of Billboard.