Andrew Dreskin has been a quiet but persistent force in live events technology for more than three decades. Before successfully selling Ticketfly to Pandora in 2015 there was TicketWeb — the world's first online ticketing company. After Ticketfly, there was Flymachine, a livestreaming venture he built during COVID that didn't survive the post-pandemic return to in-person shows.

Now, operating from his home in the Berkeley Hills, Dreskin advises and mentors young companies — "pretty much exclusively in the live events business" — and is quietly incubating something new that he describes only as "artist-leaning." He also chairs the board of HeadCount, the nonpartisan voter registration nonprofit that grew out of the jam band scene and has become, improbably, the leading voter registration organization in the United States.

Dreskin sat down with Decibel for a wide-ranging conversation about the physics of building a ticketing company, the Live Nation antitrust case, scalpers, blockchain, and why he almost bought a business that made electronic components.

This interview has been edited with language added to improve readability. You can watch a video of the entire interview here.

What have you been doing with yourself?

I stepped out of full-time employment in 2019 and genuinely thought that would be my last go-around. But then COVID happened, and some friends and I started watching livestream concerts on Zoom — cocktails in hand, watching shows together from our living rooms. It was both amazing and terrible all at the same time. The circumstances were awful. The livestream experience was also pretty bad.

It occurred to me there had to be a better way, and that became Flymachine. It was the best software I've ever built in my career — really beautiful, really thoughtful. There was only one problem: post-pandemic, the world changed and the industry didn't play out the way we expected. On the supply side, artists were focused on their in-person shows. On the demand side, once people got vaccinated, they wanted to get back out there. The volume just wasn't there.

Had you always believed livestreaming would replace the concert experience?

Never. Not for a second. There's something about the communal experience that simply cannot be replicated or pirated. What we got wrong was we believed livestreaming would become an adjunct — part of the tool belt that artists and managers and agents had. And it is, in certain segments. The jam band world embraces it. But it never became the mainstream parallel experience we envisioned.

My logic was: I live in the Berkeley Hills, and it's legitimately an hour to get to San Francisco — which is ten miles away — to see a show on a Friday night. When the kids were young, you're finding a babysitter, worrying about parking, doing dinner. Say the ticket is forty dollars. I always believed there'd be a twenty-dollar version where you watch at home for half the price. That just didn't materialize the way I'd imagined it.

You were close to buying a completely different kind of business after selling TicketWeb — something in electronic components. What happened?

I was days away from closing the transaction. I was living in New York City, I'd gained some M&A expertise during the TicketWeb sale, and I found this interesting company through some friends that manufactured and distributed electronic components. And then I missed out on the Bonnaroo investment — Rick Farman from Superfly had come to me while I was still at TicketWeb, and I was really interested in getting into that festival. I didn't end up investing in Bonnnaroo.

So I'm laying in bed one night, reading the electronic business news, days from closing this deal on this really boring, very staid business — and I had this moment of clarity. This is not me. I probably could have done great things in electronic components. But it was just too boring. In that moment I realized: I'm going to stick to live events. That's my passion, that's where I excel. And that realization, I think, shaped everything that came after.

So how did Ticketfly actually happen? Because by that point you'd already done online ticketing. What made you want to do it again?

My co-founder Dan Teree, who ran business development for me at TicketWeb, used to come to New York periodically from the Bay Area and stay at my house in Manhattan. Every year, Groundhog Day: he'd try to convince me to start a new ticketing company. And every year I'd rebuff him. I didn't want to do just another TicketWeb Part Two. It had to be transformative.

What finally changed was a confluence of events in 2007 and 2008. Live Nation terminated its Ticketmaster agreement — for Dan, who was still there, that was an inflection point. About fifty percent of Ticketmaster's revenue was potentially about to walk out the door. But what actually got me off the sidelines was two other things happening simultaneously: Apple launched the iPhone, and Facebook launched. The iPhone meant there was a box office in every pocket. Facebook meant something even bigger to me — the idea that a fan could buy a ticket and post it, and suddenly the fan becomes a marketing channel for the venue and the promoter. That was the game changer. That was the watershed moment.

You basically created the idea of the middle market in event ticketing. How do you assess where it stands now? We've seen Eventbrite get sold, Dice get sold — it feels like the field is consolidating.

There's both a lot going on and nothing going on, simultaneously. A lot of the same old story in ticketing, but if you look hard enough, there are pockets of genuinely interesting stuff. I joke that I just can't believe people are still starting new ticketing companies. A VC I really like pinged me just last week about a young company they're looking at, and my response was, "You're a glutton for punishment."

At the high end, I’m advising this interesting ticketing company vivenu, out of Germany. Three economics majors, twentysomethings, who knew nothing about live events and nothing about ticketing, did a ton of research, and quietly became — I'd argue — a top five ticketing company in the world over the last six or seven years. They built it entirely modular, as a series of microservices.

Each client is its own merchant of record. They don't rely on the upfront cash business. And they're now operating on five continents, fifty countries. They power something like forty ticketing companies around the world as white-label technology. There's no scenario where these guys should have pulled off what they've pulled off. And that's exactly why it's such a great story.

You've mentioned that ticketing companies shouldn't be acting like banks. What do you mean by that?

Somewhere along the way, the ticketing company became the bank instead of a software company. Venues and promoters get offered big upfront signing bonuses — cash against future service fee revenue. In most other industries, what they're calling a signing bonus would be called a bribe. And I'd tell venues and promoters at Ticketfly: you will make more money on service fees if I do not write you an upfront check. I'll take a lower per-ticket fee and you'll net more at the end of the year. I was always mystified that almost nobody took me up on it.

Now I get it. If you need a new PA system or you need to remodel your bathroom, I understand. But outside of genuine capital needs, it never made sense. My advice to any young CEOs in ticketing is this: find segments of the market — high-end venues, college athletics, attractions — where that practice is less prevalent or outright prohibited. The upfront check is a payday loan. And like all payday loans, the lender wins in the end.

What about Hive? You're on the board there. What's the thesis?

Hive is kind of what I think Ticketfly was to TicketWeb, in terms of strategic approach. At TicketWeb we worked with great indie venues like the Bowery Ballroom, but we also ticketed tennis tournaments and MoMA and the Guggenheim and the Louvre Museum. What Ticketfly did was say: we are only going to be the best ticketing company for middle-market music venues. We eschewed all of that. And we said, we are just gonna be the best for middle market music venues. And because of that vertical focus, you know, we were really able to satisfy the needs of a very sort of narrow constituency.

Hive does that for marketing automation in the live events space. It's always going to be better than MailChimp or Constant Contact or Salesforce Marketing Cloud for live event promoters, because it's so deeply integrated with the ticketing platforms. Your email marketing, SMS, ad buying, all tightly linked to your ticket salesdata. That tightness is something generalist tools just can't replicate. And the business is thriving.

You're also advising CashorTrade, the fan-to-fan exchange. What’s the opportunity there?

I hate scalpers. It's an intractable conundrum the industry has been grappling with for decades. And I've said this publicly many times: until venues and promoters dynamically price their inventory and let the free market do its thing, the secondary market will always thrive. If you won't price your inventory correctly, StubHub sure will. The scalper sure will.

I can go on record and say that in my entire career, I have never once allowed a scalper access to a TicketWeb or Ticketfly ticket. Never knowingly shoveled tickets out the back door to maximize revenue. And anyone who's worked in this business has seen the look on a kid's face when they show up at the door with a fake ticket they bought from some shady fraudster, or a sixty-dollar ticket they paid six hundred for. It's awful. CashorTrade solves for that — it's a real face-value exchange where fans who can't go can trade or sell tickets at what they paid. No scalping. And the venues and promoters benefit too, because no-shows don't help anyone. You want warm bodies in the venue at the bar.

You were interviewed by the DOJ when Live Nation and Ticketmaster were merging. What did you tell them?

My thinking at the time was: the merger would create a tremendous opportunity for upstart providers like Ticketfly. My supposition was that no venue or promoter competing with Live Nation would use Ticketmaster, because why would you give your competitor more revenue? I thought those venues and promoters would depart en masse and seek different solutions. So I told the Justice Department I was okay with the merger being consummated.

I was wrong. What we learned over time is that most venues and promoters just don't care enough. No one ever got fired for choosing IBM. And no one ever got fired for choosing Ticketmaster. It's become a kind of institutional insurance policy. I was genuinely shocked by how many venues and promoters stuck around. I thought the merger would create a more vibrant middle market. That didn't happen the way I expected.

What do you make of the current antitrust case? The DOJ pursued it and then quickly settled, passing the case to the states — do you think the government handled it correctly?

I find the whole thing confounding. You have a purportedly extremely pro-business administration that came into office, and for the life of me I cannot figure out why they didn't kill the Justice Department's antitrust examination of Ticketmaster and Live Nation. You've got this unapologetically pro-business, capitalist-leaning government that's letting it continue. What did Live Nation do wrong to not get a reprieve here? I genuinely can't figure it out.

I'm not saying I agree or disagree with how the Trump admin handled the case. I'm just observing that it doesn't fit the pattern of everything else happening.

There's been a lot of concern about Live Nation using its position to subtly discourage venues from leaving Ticketmaster. What did you observe when you were competing against Ticketmaster?

In the early days, I felt like that was more overt and more prevalent. We had venues and promoters tell us directly that if they terminated their Ticketmaster agreement, they were going to get fewer Live Nation shows. That's illegal. It's a violation of the consent decree.

But I actually think that, as an institution, Live Nation learned its lesson. I don't believe there's currently an institutional policy of threatening venues. The thing is — it doesn't need to be said. It hangs in the air. If I terminate my Ticketmaster agreement, Live Nation may not actually be threatening anything, but even the possibility of getting fewer shows may be enough for venues to stay. The implicit threat outlives the explicit one.

What about the moves toward digital-only tickets as a way to curb the secondary market? Is that good for fans or bad for fans?

I'm genuinely of two minds. On one hand, I love the idea of restricting resale to face value. On the other, someone bought a ticket, they paid for it, and there's a legitimate argument that they should be able to do with it what they want. Fans love ticket transfer. Anything that tamps that down is not something I'm instinctively in favor of.

That said, I do like the idea of a ticket being tied to an individual. I like the idea of applying some rules to resale. And most importantly, I would love to see a portion of resale revenue shared with venues, promoters, and artists rather than letting that money escape the ecosystem entirely. We're going to see stock trading and other things migrate to the blockchain. I think we'll probably see something similar happen in event ticketing in some form — and that could be the mechanism that makes some of this work.

The European allocation model — where venues aren't exclusive to one ticketer and sell inventory across multiple platforms — do you think that could work in the U.S.?

Not only have I seen the European model — I participated in it. TicketWeb had a joint venture in the UK, TicketWeb UK, which was really wonderful. My partner in that was Ian Howard, who owned the Brixton Academy and the Shepherd's Bush Empire. Brilliant guy, we're friends to this day.

From the inside, though, the allocation model is a genuine mess if you're a venue or promoter. Juggling inventory across multiple providers completely breaks down with reserved seating. You've got someone in a box office with a spreadsheet: this provider has five thousand tickets, that one already sold five thousand, we need to shift inventory, how do we scan at the door — do I hold five different scanners? I get the goal. The goal is to open up distribution and reach more fans. But there's an elegance and grace to a canonical system of record. I think open distribution via channel partners —the Booking.coms and tour operators of the world — is a better way to approximate what people are actually trying to accomplish, without the operational chaos of a true allocation market.

You chair the board of HeadCount. How did you end up there?

I've been on the board for roughly twenty years now. Somehow I ended up as Chairman. They should have kicked me off a long time ago — there really ought to be term limits, though I'll note the Supreme Court hasn't managed to implement any either. I think they should.

HeadCount was born out of the jam band world. Andy Bernstein and Mark Brownstein from the Disco Biscuits founded it. I remember in the early days, we barely had enough money in the bank to get through the year. Now, without going too far into it, it's become the leading voter registration organization in the United States. We've gone from registering kids to vote at Phish concerts to working with Billie Eilish and Harry Styles and Ariana Grande. It started as a path to civic engagement through music, and it's become something much larger than that. Genuinely gratifying work. Not everything has to be about capitalism.

You've teased a new project you're incubating. Can you tell us anything
about it?

A little. I've been around this business for thirty-five years, starting when I was promoting concerts as an undergrad at Tulane — at Tipitina's, actually. My son is now an undergrad at Tulane producing concerts at his fraternity, which is wonderfully full-circle. After Ticketfly, I never imagined I'd do another full-time operator role. But here I am.

What gets me off the sidelines is a specific kind of opportunity: something in or very near live events where I can see a chance to bring real innovation and transformation. With TicketWeb, there was no such thing as online ticketing. With Ticketfly, it was the confluence of mobile and social. With Flymachine, it was the livestreaming hypothesis. Each time, it was an old-world offline thing that technology could fundamentally change. This one is more artist-leaning. I've spent a lot of time on the venue and promoter side of the business. I want to do something that helps artists. And I've assembled a group of people I'd describe as the GOATs of their respective portions of the live events industry. We think we've found an opportunity. News should come in weeks, not months.

Thirty-five years in this business. What's the thing you know now that
you wish you'd understood at the start?

Everyone's good at something. I learned that lesson in a very specific moment when I was about to close on that electronic components company, lying in bed one night reading trade publications that bored me to tears. The lesson wasn't just "follow your passion" — though that's part of it. The lesson was that I had a specific edge in a specific world, and diluting that edge by applying it somewhere else was a losing trade. I stayed in live events and never looked back.

The other thing I'd tell a younger version of myself: it's okay if they don't all work. I've had black eyes. Field Day, the festival I launched in New York — that one didn't go the way I wanted. Fly Machine didn't survive the post-pandemic shift. What I've learned about being an entrepreneur is that sometimes they work, and sometimes they don't. The ones that didn't work taught me something the successes couldn't. And the relationships you build along the way — people you've known for twenty years across this industry — those are the things you sacrifice when you exit a business and don't get back enough of.