Andrew Dreskin and the business of getting you through the door

Before there was a ticketing company to sell, Andrew Dreskin had a concert to remember. At roughly twelve, he persuaded his parents to let him and a friend see AC/DC on the For Those About to Rock tour. Decades later, the details still came readily: Angus Young’s schoolboy uniform, the lights, the scale of the stage. Some children leave an arena wanting a guitar. Dreskin eventually found his way to the box office.

That route took him through college concert promotion, a record label, two ticketing startups and a streaming venture. It also produced a peculiar career rhythm: help change how people buy tickets, sell the company, discover that the business still has problems worth working on. The encore has become a recurring engagement.

TicketWeb put him in the early history of internet commerce. Ticketfly made him a familiar name among independent promoters. His more recent advisory work at CashorTrade brings him to the question of what happens when a ticket changes hands. Across those different jobs, the person buying admission remains a useful place to begin.

A promoter’s education

Dreskin grew up in New Jersey and went to Tulane University in New Orleans, where he earned a history degree. He also began promoting concerts. His first show was at Tipitina’s, a rather persuasive classroom for someone interested in the mechanics of a good night out. A promoter has to care about the performance and the unromantic business of getting enough people into the room.

After college, he worked for an independent Bay Area concert promoter and became general manager at Beserkley Records. His career crossed the places where music becomes a business: the label, the venue, the festival and, eventually, the transaction. The technology work grew out of that experience. He already knew the people who would have to use it.

There were festivals, too. He created Field Day, whose 2003 edition featured Radiohead and the Beastie Boys, and co-founded the Virgin Mobile Festival. Those projects gave his working life a physical counterpart to the software: a stage, an audience, an event that had to happen at an appointed hour. You can postpone a meeting. A crowd holding tickets tends to be less accommodating.

When buying online needed an explanation

In 1995, Dreskin co-founded TicketWeb. The early sales conversation involved a hurdle that now sounds almost quaint: persuading clients that the internet would endure, and that people could safely use credit cards there. A ticketing product first needed a plausible world in which customers would trust it.

One small scene stayed with him. On a trip toward Chicago’s O’Hare Airport, he saw a Southwest Airlines billboard carrying a web address. He took it as a sign that the medium was moving into ordinary life. A URL beside a highway could do something a founder’s presentation could not: make the internet look normal.

By May 2000, TicketWeb had about 700 clients, spanning nightclubs and institutions. Its customers included the Bowery Ballroom, the San Francisco Symphony and the San Diego Zoo. That is an unusually broad bill, even by festival standards. Its software allowed an internet-connected desktop computer to function as an online box office without special equipment.

Ticketmaster Online-CitySearch acquired TicketWeb for $35.2 million in stock that month. The transaction gave the larger company access to TicketWeb’s small and midsize customers. For Dreskin, it closed the first company chapter. It left plenty of room for a second opinion about what ticketing software ought to do.

The encore began with payroll

Dreskin and Dan Teree founded Ticketfly in 2008. Having already sold one company did not exempt them from the difficulties of starting another. During the early fundraising period, they sometimes made personal deposits at the bank to cover employees’ salaries. The origin story contains less champagne than the eventual acquisition headline might suggest.

Early backers included Howard Lindzon and Roger Ehrenberg. An institutional seed round followed in 2009. Dreskin later recalled turning down a prominent investor whose expectations felt wrong for the business: the investor wanted $100 million in revenue within four years. The founders preferred a pace and a partnership they could live with.

That choice makes his account of fundraising unusually practical. Money comes with a working relationship, a timetable and an opinion about what success should look like. An impressive name can still be an awkward person to share a future with. In ticketing, as elsewhere, it pays to read the conditions before accepting admission.

One show, too many forms

Ticketfly’s product argument started with an ordinary promoter’s irritation. Confirm a show, and you might have to enter the same information into the ticketing system, the venue website, an email newsletter and several social networks. Each separate entry created another opportunity for wasted time or an error.

The company linked ticketing with marketing, websites and community features. Enter the event once and distribute the details across the connected outlets. In 2009, that list included MySpace, which usefully dates the problem without making it any less recognizable. A fashionable destination can disappear; the chore of retyping a show announcement survives.

The 9:30 Club became an early client. Its co-owner Seth Hurwitz also worked with Dreskin on the Virgin festival, giving the new ticketing relationship a foundation in actual event production. By May 2010, Ticketfly had more than fifty venue and promoter clients and had secured $3 million in Series A funding.

By April 2014, Ticketfly was reporting 11.2 million tickets processed for more than 80,000 events in the preceding year, across the United States and Canada. Those figures describe a company that had moved well beyond its first handful of clubs. They also describe a lot of promoters with less reason to enter a date twice.

Its 2014 acquisition of WillCall extended the interest beyond admission. WillCall brought mobile technology for activity inside the venue and information that could help operators understand customers and reward loyalty. The ticket became one part of a longer relationship between an audience and a place.

A listener is a possible ticket buyer

In October 2015, Pandora announced its agreement to acquire Ticketfly at an approximately $450 million transaction value. The strategic attraction was easy to understand: a listening service knows something about a person’s musical interests. A ticketing service knows when an artist is playing nearby. Joining the two offered a way to make concert discovery more personal.

At the announcement, Ticketfly worked with more than 1,200 venues and promoters. Its clients included Brooklyn Bowl, Forest Hills Stadium and Merriweather Post Pavilion. These were places with their own identities and audiences, linked by the less visible systems that make an evening possible.

Eventbrite completed its acquisition of Ticketfly from Pandora in September 2017. Dreskin became president of music at Eventbrite and served on its board. In 2019, he stepped away from the operating role and moved into a multiyear advisory arrangement. The corporate names had changed around him; independent venues remained central to his public description of the work.

“I absolutely believe the world needs a vibrant independent music community.”

Andrew Dreskin, 2019

Can you put the crowd on a screen?

Flymachine, his next company, addressed a different part of the evening. Watching a concert online could provide the sound and the picture while leaving out the pleasure of being there with other people. The missing element interested someone whose professional life had long depended on gathering an audience.

The founding group included Rick Farman, a co-founder of Bonnaroo and Outside Lands, Matthew Davis of music technology company [namethemachine], and ATC Management. In July 2021, Flymachine announced $21 million in new funding, led by Greycroft Partners and SignalFire. Its backers also included people from artist management, promotion and music.

The platform let viewers join public rooms or make private ones for friends. They could hear and see one another while watching the performance. By February 2022, Flymachine had presented about seventy concerts, and Boston’s Boch Center had announced a partnership involving its Wang and Shubert theaters. The experiment treated the people beside the stage as part of what a broadcast needed to carry.

Dreskin’s own account of using it included chance encounters with old friends in public rooms. That is a modest but revealing measure of what he wanted the product to accomplish. A good concert contains a performance and a collection of less programmable events: the person you bump into, the conversation you resume, the friend who arrives late.

Still interested in who gets in

His public work also includes chairing the board of HeadCount, which works with musicians and other partners to encourage democratic participation. The connection between a gathering and what its participants might do together extends beyond selling admission. Music provides the meeting place.

In October 2025, CashorTrade announced Dreskin’s arrival as a strategic advisor. The platform facilitates fan-to-fan exchanges at face value. It brings his experience to another point in a ticket’s life: the moment its original buyer needs to pass it on. In April 2026, he returned to the subject in an extended Decibel and Docket interview covering his career and the live-event business.

Seen across three decades, his career has a consistent object of attention. He has worked on the purchase, the promotion, the discovery and the shared experience of a show. Each company has approached a different obstacle between an artist and an audience. The twelve-year-old who remembered the lights found a surprising amount to do before they came up.