Flymachine’s Andrew Dreskin: ‘You Never Know What’s Coming Around the Corner,’ But He’s Caught a Few Big Trends

Andrew Dreskin has been a leader in digital event startups for as long as that market has existed. His first notable startup, TicketWeb, brought ticketing sales online before airlines, major retailers, or much of anyone had a presence there. Ticketmaster acquired it for $35.2 million. Then he regrouped the team to create Ticketfly, which Primary General Partner Brad Svrluga invested in, and the team built into the dominant middle-market ticketing provider in North America. Pandora bought it for $450 million. Andrew’s newest business, Flymachine, creates a social video and digital performance space where fans can explore a range of virtual events in public and private rooms. Andrew has recently secured a $21 million Series A for Flymachine, which will help his mission to bring real-life events to people virtually.

In this interview, Andrew details his experience creating the first online ticket sales platform, gives his take on NFTs, and offers his pros and cons on the fundraising process.

Can you trace back the origin of Flymachine and your interest in the music business?

I grew up a devout music fan. I was the kid who had posters covering every part of the wall in my bedroom and started going to concerts when I was very young. That was the beginning, and then my love for music took me to New Orleans, where I went to college at Tulane. There, I started promoting concerts and realized that you could combine what you loved and what you did for work. I moved from the music industry into the technology business with the founding of TicketWeb, and I guess the rest is history, so to speak.

What’s a challenge you’ve faced over the course of your career that has been defining in your life?

When we founded TicketWeb, our challenge wasn't trying to convince prospective clients to sell tickets with us versus another provider, because there wasn't another provider. We had a different challenge, which is maybe more interesting. This was 1995. We had to convince prospective clients that the internet was a viable medium, that it was here to stay, and that it was a secure place to perform credit card transactions.

We were lucky because as time went on, the internet started to catch fire and take off. One of the first moments when I knew we'd be successful was when I was on my way to O'Hare Airport in Chicago and saw a billboard on the side of the road for Southwest Airlines. At the bottom of the billboard, it read: www.southwest.com. It was the first time I'd ever seen a URL on a billboard and I thought, "there you have it." The reality is that there were only four, five, or six companies in the world selling things online at that time, so that was an indication that the internet was becoming prevalent in society, and that's what we needed to succeed as a business.

What's something you learned as you pitched Flymachine to investors? What do you feel like investors want to see from somebody at an early stage?

Investors want to see that you’re operating in a big market and have seasoned management. Investors tend to like finding repeat founders who know the ins and outs of building businesses and know how to roll with the good and the bad. They look for product-market fit. They look for interesting technologies that are sort of at the frontier, as I mentioned, in a big market. And also, I think transformative technologies have a chance to change and improve society where you can build a big business.

I enjoy the fundraising process because the investors I get to meet are incredibly smart and insightful. But the complaint I have about fundraising is it's just all-consuming. While raising my Flymachine Series A recently, I realized that it just takes your focus away from the operation of the business. It's time-consuming, and you realize that you're spending 70 percent of your time fundraising when you'd rather be operating the business.

When you're hiring people in this industry, what types of characteristics or backgrounds are you looking for? What type of people are you looking to work with?

For some odd reason, I tend to have the same people work for me over and over again. At Flymachine 80 percent of our employees have worked for me previously, some in multiple places for over 25 years. I look for people who are smart, hardworking, dedicated, loyal, intellectually curious, and just A players. I find that you can do wonders with a small team of rock stars, and I take quality over quantity any day. That's generally what we look for.

We were actually able to drop a bunch of folks into Flymachine who worked together for many years at Ticketfly. They just hit the ground running, because, for the most part, they had similar roles to what they had previously, so they were able to move really quickly.

Are there any predictions or trends that you're following in the software infrastructure space?

I’m interested to see where AI (artificial intelligence) can take us in terms of machine learning and data insights. I’m also fascinated by what's going on in the crypto space and keen to see where that all leads, especially NFTs (non-fungible tokens) since I’ve been a long-time art collector.

Is there any way you can see trends like cryptocurrency and NFT’s relating to ticket sales?

I think for virtual events there's a big opportunity where you’ll be able to mint a performance or a song and create an NFT. Eventually, our clients will be able to mint a song from a concert and one or offer three or five copies to users online. There’s definitely an opportunity there, but it’s going to take some time to get after it. Time will tell, but one of the things I love about this business, the business of technology, is that you never know what's coming around the corner. Did I think that Beeple would sell a GIF for $69 million? With my art collector hat on I'm scratching my head at some of this stuff, but I do think there are some interesting opportunities in the NFT space. It'll be interesting to see where it all leads.