Brewing Success In The World Of Advertising And Media With Jason Schulweis

Jason Schulweis Podcast Art


In this episode, Evan Brandoff speaks with with Jason Schulweis, EVP, Brand Partnerships & Creative Studio at Morning Brew, to give us an inside look at what it takes to run the daily email newsletter covering the latest news from Wall St. to Silicon Valley. Jason shares his insight on how Morning Brew built a dedicated audience with trust, his ethos for attracting brand partnerships for the newsletter, details on their $100M acquisition, and where his inspiration comes from. Packed with insight, this episode is not to be missed!

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Brewing Success In The World Of Advertising And Media With Jason Schulweis

We welcome Jason Schulweiss onto the show. Jason is the EVP of Brand Partnerships and Creative Studio at Morning Brew. He is both thoughtful and interesting and has a lot of insights to share. Let’s get into it.

Jason, welcome to the show.

Thank you so much for having me. It’s great to be here.

I’m excited to chat with you. I have followed your career for a while now. It’s incredible to see all the success you’ve had and the success Morning Brew has had but I want to start from young Jason. Where are you from originally?

I am a Manhattanite, born and raised. I’ve been in New York City my whole life minus the four years I was in Michigan. My wife is also a native New York City person as well.

You’re from Manhattan and then went to the untraditional path from New York to the University of Michigan.

I know we’ll get there but there are deep Michigan ties with Morning Brew as well.

Were you a Rick’s or Skip’s guy?

I would say probably more so Skip’s, especially earlier on Post 21 and then toward the end is when I started going to Rick’s a little bit more. I was also a vortex throw away from Rick’s.

What did you study in school?

In a professional organization and in any professional relationship, feedback remains important.

I double-majored in Psychology and Political Science, which has both nothing and everything to do with what I do now. It’s interesting because Psychology is about understanding people, who they are and how they think. Political Science, I did not necessarily enjoy but it taught me how to write, speak and convey points in a clear, concise way. Combining those things makes me, hopefully, a better sales and marketing professional. I like to tell myself that anyway but I would say the things probably that I learned most in school happened in between and outside of class.

You graduated in ‘08, which was not the best time to enter the workforce.

I would say probably ‘09 was worse but ’08 was also not great. I got an unpaid internship after school because it was to your point. It was not the best time to be looking for a job.

Where was that internship?

That internship was at a digital agency called Deep Focus in New York. It was one of the first digital and engagement agencies around. I had no experience doing digital marketing but I got this internship. I was fortunate that I could afford to be an unpaid intern for a couple of months. I fell in love with digital media and marketing. From there, I was able to get a media coordinator job and then a media buying and planning job. The rest is history. I’m lucky that I fell into that.

When you were in school, did you want to go that route? Did the market dictate where you were able to work after school?

The market dictated that. I’ll say that maybe there was some universal juju happening behind the scenes because one of the things that I started to do in school outside of class and I was talking about this before, I don’t know if it still exists but there was a party at the University of Michigan called Splash Bash. When I was a freshman, I was in the AEPi fraternity.

We went up to Western Ontario to go to this same party by the same name that they threw there. I was looking at it and I was like, “I could do that in Ann Arbor.” We brought the concept to Ann Arbor. That was my first experience in securing a venue, selling tickets, selling sponsorships and doing all of those things. That is more directly what I ended up doing at different stops in my career like at Thrillist. A big thing about what we did were events and marketing sponsored events. I was at Live Nation. That’s Live Nation’s business. It was very fortuitous that Deep Focus ended up being the professional stepping stone to those things.

You were the guy behind the scenes that enabled everyone else to party and have a good time in school.

That’s correct. I had my fun but I have a responsibility gene in my DNA somewhere. I was making sure that everyone had a safe and good time.

Were you immediately working in sales and brand partnerships?

No. On the agency side of things, I was doing media planning and buying. HBO, AMC and Estee Lauder were a few of our clients. We would get briefs from them and we would RFP different media publishers and see how to make a plan that fit the HBO show or AMC launch that ended up happening. I got to work on really cool things. AMC Mad Men Yourself was a campaign that we did that won a few awards back in the day. I also got to work on Microsoft Bing. We were their social agency of record back in the day.

WGP Jason Schulweis | Advertising And Media

Advertising And Media: Inspiration can come from anywhere.

I worked on the campaign that was the first-ever brand integration into Farmville in Facebook where if you liked the Microsoft Bing page, you got farm cash. That was both successful but also showed that likes as a form of KPI of success were not the way to go because we were able to get the brand a ton of these likes but there was no strategy as to how to keep people engaged. That was the turning point of social advertising 1.0, which was super interesting. That job exposed me to what the publisher side could be because we worked closely. Two of the publishers that I ended up working closely with were Thrillist and Yahoo!, which is where I went after Deep Focus. I went to Yahoo! for three and a half years and then I was at Thrillist for a little over a year and a half after that.

That’s so interesting, the farm cash initiative that you worked on. Many people wonder how do ideas like that come to life. Is it an idea from the client or the agency? What goes into bringing something like that to the market?

Inspiration can come from anywhere. I am a big believer in what I call collecting dots, like experiencing things, talking to new people and collecting people and experiences. Some of that came from participating in social. At the time, you couldn’t really be pitching ideas unless you were an active Facebook user or an active games player on Facebook. You combine that with gamification-type strategies and tactics that may exist elsewhere and you’ve got a bunch of smart people in a room.

I don’t remember exactly how it came to be but Deep Focus was a small integrated agency at the time, which is very different than a lot of agencies that exist now. We had media people, creative people and account people all next to each other mashing ideas and perspectives together. We ultimately came up with amazing ideas. I like to think that was the special sauce as to how that particular idea was made.

When sitting in a role at an agency, you’re often being sold to. It’s so hard to go from that role to the other side where you’re the one selling. How did that transition happen?

It happened gradually. When I was on one side of the house being pitched to and then I went over to Yahoo!, I didn’t go immediately into a sales role. I went into an account management role, which is still under revenue working closely with sales but doing a lot of media planning. It was not necessarily buying but planning. It was similar. It was an easier transition into the dark side, which is being in sales and the publisher side.

From there, I did a little social sales at Yahoo! and then I went more into integrated marketing. It was still everything under the revenue-generating umbrella but before I went into the role that I’m in now, I never was a field seller. I had done all of these other things underneath the revenue umbrella but being able to do all of those things has allowed me now to manage a very large group that has sellers, integrated marketers, account managers and all of these different groups being able to speak all over those different languages and bridge them together.

I’m sure having a purview into all the different parts of it has been a huge factor in the success that you’ve had.

I appreciate it. It’s like professional empathy. If you put yourself in other people’s shoes because you’ve done that job, it helps a ton. It’s also shedding your ego where you haven’t done particular jobs. I chatted with my sales team and had an honest conversation that they’re better at sales than me because they’ve been doing that particular job much longer than I have. It was a very cool moment because I realized that that had been on my mind a lot. Being able to own what I know and was good at and what I didn’t and bringing that out into the open and not trying to shield it or shy away from it was a cool moment.

I could tell from our limited interactions that something that you’re really good at is being self-aware and acknowledging what your strengths are, where you have room to grow and leaning on other people. Is that a learned skill? Do you feel like that that was intuitive to you?

It has come naturally to me. I talked about professional empathy but I’ve always thought of myself as an empathetic person. From a psychology perspective, that goes hand in hand with being a high self-monitor right. It is understanding how you are perceived. There’s a huge detriment to that, which is you can’t operate from a place of only how other people see you but that was always something I was acutely aware of and always tried to adjust.

A lot of that requires knowing things that you are good at and aren’t good at and when you need to lean on other people and when not. I would say the refinement of that has taken a lot of time and did not come naturally. There’s a degree of needing to be okay with not knowing things and saying, “I don’t know.” That part is tough. A lot of that goes into understanding feedback and how important feedback is in a professional organization and in any professional relationship. Candidly, I probably only got good at giving and receiving feedback in 2022, 14 years into my career.

What are the keys to being good at giving and receiving feedback?

In terms of giving feedback, we went through management training at Morning Brew earlier in 2022. I’ve done that a few times but this was the first time that there was a large portion of it that was dedicated to giving feedback. One of the first things that you’re supposed to do is ask for permission, like saying, “Can I give you feedback?” If you just come out with what the feedback is, a lot of people may not be in a good place to receive it and then it’s all downhill from there but you can ask the person how they thought something went and how it went well and you share your thoughts there.

The next piece is asking them how it could have gone better and what they would do differently next time. You have to be always phrasing it as to not harp on the past but talk about what you can do differently, learning from the past moving forward. It doesn’t need to follow that exactly every time but those are good things to be thinking about.

The receiving end is tough because I believe that the reason why a culture of feedback doesn’t exist in most organizations is that people are afraid of hurting the other person’s feelings or the other person not reacting well. For me, I wanted to set a good precedent and example for my team so everyone, no matter what role they’re at or level, gives me feedback. It’s awesome.

I posted about this on LinkedIn and Twitter. That has allowed me to get better faster because I’m learning in real-time what’s working and not working because everyone feels comfortable giving me feedback. My hope is that everyone also starts to feel comfortable. The amount of written feedback now because we’re all virtual and remote is a whole other variable to it because if you give me feedback with a period at the end versus an exclamation point or ellipses, those mean entirely different things but they shouldn’t. Part of it is not trying to read too much into how you think the other person is delivering it and take the facts of what they’re saying and think about it. You may disagree and you can ask for follow-ups, more detail and all those kinds of things but there’s some truth there. That was a very long-winded answer to your question.

Transitioning to Morning Brew, you alluded to it before that the founders are from Michigan. How did you connect with them?

A friend of mine by the name of Phil Schermer is an incredible dude. He used to be the VP of Marketing and Chief of Staff to Frank Cooper at BlackRock. Phil founded also Project Healthy Minds, which is an incredible mental health startup. Phil is one of those guys where if he texts you like, “You got to meet this person,” there are no questions asked. You do it. That was what happened with Phil connecting me and Alex Lieberman. Phil also went to Michigan and knew Alex from Michigan. Both of them are much younger than me but Phil knew Alex and Phil and I have been connected for a while so he was like, “You guys got to meet over drinks.”

At the time, I was at MediaLink. I took that meeting thinking Morning Brew is a really cool company. I subscribed to the newsletter. I liked it. Maybe I could bring them over as a consultant client but then, I met Alex. He’s so impressive. He was smart and had the vision and the poise. What he and Austin had already built at that time, they were hiring for a head of brand partnerships. That was not my intent going into that meeting to talk about that role but as we got to know each other and I was sharing my story, my career and my experience because part of the pitch when you’re a consultant is pitching your experience, we came together naturally where I had this breadth of experience inside of a revenue organization at a lot of different media companies and they had aspirations to ultimately be a big media company.

Whereas most people who are eligible or look at how brand partnerships roles come up specifically through the sales organization as a seller, I had this different experience. I shared how helpful I think it would be to have someone who can speak all of those different languages underneath a revenue org and umbrella. He agreed. We got along well. That led to more conversations. I met Austin. Austin was so impressive, smart and strategic that Alex was like, “I had the vision.” From a founder duo, I was like, “This is incredible.” They went to Michigan so that was cool. I then met the rest of the team. When you have a startup that has truly generational talent founders, a differentiated product and a team full of people who are smart, kind and passionate then it wasn’t that much of a risk to go to a startup and help build the thing.

How big was the team when you joined?

I don’t remember exactly what number of employees I was but it’s within 1 to 20. We’re now over 230. The sales team that I inherited was 3 people. The equivalent of that team now is about 60.

What time horizon was that growth?

WGP Jason Schulweis | Advertising And Media

If you give feedback with a period at the end versus an exclamation point at the end or in ellipses, those mean entirely different things.

I joined in July of 2019.

That’s incredible.

It has been a lot and a lot of that has been remote. We’ve been able to retain a lot of talent and keep the culture. I’m excited. We have an office opening up in a couple of months. We have been without an office for the last couple of years. I’m excited to get back into it with everyone. We remain remote empathetic, which means that people can remain remote or go in two days a week, four days a week or whatever works but I am excited to see people. I’ve started to do that again both with the team and with clients. I am extroverted to whatever degree so getting to see people again gives me energy.

There was big news that Insider acquired Morning Brew. Was it in 2021?

It was October of 2020. It was Q4 of 2020. It was via Axel Springer out of Germany. They’ve got a huge portfolio now in the US with us, Insider and Politico.

The question I was asked by 5 to 7 people when the acquisition happened and I know that Morning Brew is so much more than a newsletter, was how does a newsletter company get acquired for almost $100 million?

I will try to answer this one succinctly because I feel like I can talk about this for a long time. At that time, we were more than a newsletter. We had a podcast. We also had both B2C and B2B franchises. Those would affect evaluation differently but within both, the newsletter audience and especially one at our size with our open rates, that is a differentiating factor because what you have at that point is a degree of trust and relationship with an audience that is more than an audience. That is a community. They’re fans of Morning Brew.

We have this one slide in a deck where someone got a Morning Brew tattoo on their leg. Our referral program accounts for 50% of the people. People are sharing Morning Brew. They’re wearing Morning Brew. They are a part of Morning Brew. There aren’t a lot of media companies that have that type of relationship with their subscribers, readers, listeners or whatever it is. There’s a lot of value there. Having that quantity of quality is rare.

A lot of media companies have all started newsletters. They tried to develop that one-to-one relationship whereas they had one too many before. For us to go from having that size of one-to-one relationship gives us a better license to expand out from there because we already have the hardest thing to get. It’s the relationship and trust. Axel saw that and went for it.

I’m sure they’re happy with their investment.

I believe so.

Speaking to that one-to-one connection, the newsletter specifically, can you share any stats about how big the audience is? What are those success metrics? How do they compare to industry standards?

It’s incumbent on the sales team and us at Morning Brew to make sure that we are using all opportunities to educate our partners in the market as to who we are and what we do.

There are about 4 million people that subscribed to the Morning Brew daily newsletter now but across all of our newsletters, it’s about 5.5 or so million at this point. When you account for all of our videos, podcasts and events that we do now and our social reach, we’re talking about a universe of over 10 million, which is super compelling. Open rate was always the thing. That was the super sexy metric.

In late 2021, Apple released iOS 15, which because of privacy standards, if you were on iOS 15 on any device, Apple would open the email effectively outside of your phone and then deliver it to you. It was inflating open rate numbers. We still keep track of that because there are corollaries that we can look at engagement rates where we see the total number of clicks on things in a newsletter and see how that’s changed over time but we have to rely on that a little bit less now.

We’ve seen ad performance maintain and readership maintain and continue to grow. We’re very aggressive when it comes to churning people who don’t engage and don’t open. All of those things are still moving in the right direction and let us know what was once upon a time a daily 40% plus open rate, which was insane. We know that a lot of those metrics across all of our newsletters have been maintained, which is great.

When someone is looking to sponsor a newsletter, what metrics are most important to look at when choosing the right newsletter for you?

First, we will try to talk to them about perhaps a broader content idea that can come to life in the newsletter on our O&O through branded content. If they say, “We just want a newsletter,” that’s fair enough.

The podcasts are great, by the way. You have so much incredible content.

Thank you. If someone comes to us and doesn’t know that we are more than a newsletter because there are still some people that know us like that, it’s incumbent on us and the sales team at Morning Brew to make sure that we are using all of those opportunities to educate our partners in the market as to who we are and what we do but we still do have some newsletter-only partners.

We do share open rates both historical and current. We can do that. We share total potential reach, which is a list-size type of thing. We’ve gotten a lot of new KPIs that we talk about that measure and the ad engagement within a newsletter, which are the clicks and engagement on an ad compared to the total number of clicks in a newsletter. We’ve got a lot of different types of benchmarks that we can talk to our partners about.

You’re the EVP of brand partnerships and creative studio. What is the creative studio?

The creative studio is an incredible entity inside of Morning Brew helmed by an incredible woman by the name of Elyssa Starkman. She’s coming up on her year anniversary here at Morning Brew. That is comprised of creative strategy, which is what we used to call integrated marketing. They typically handle RFPs and proactive ideas for different clients against our three sales pods. It’s how we’re broken out by B2B consumer and finance.

There’s also a content strategy. The content strategy team works primarily internally with our B2B and B2C edit teams to take their ideas, what we’re doing, package that up and get that into the more customization funnel. We’ve got a big branded content team that touches everything from the newsletter ads to the branded content that you see on our O&O to social to video to audio. We’ve got a production team. We also got a research and insights team. They all sit within the creative studio.

That’s so interesting. Something that you had said before the show which I found interesting and it resonated with me is that you believe that every touchpoint must be a two-way street and things that the worst emails in the world are marketing emails which you cannot reply to and I agree. How does Morning Brew do that? You said it was one-to-one but from Morning Brew to a lot of people, how do you engage and enable people to re-engage and respond?

WGP Jason Schulweis | Advertising And Media

Advertising And Media: When you have a startup with truly generational talent founders, a differentiated product, and a team full of smart, kind, and passionate people, it wasn’t that much of a risk to go to a startup and help build the thing.

Our edit team will kill me for saying this but hit reply on the email that you read the next morning and say hello. They will respond to everything. Our managing editor, Neil, has been doing this for three years. We’ve also got a team that helps manage all the inboxes across every single different franchise that sends out a newsletter. That strategy existed long before I came in hot with my biggest pet peeve being the do-not-reply email. I still can’t fully comprehend that that’s a thing. We’re very good about responding to those types of emails. We have a big social team. Anytime people are tweeting to us or DM-ing us, we’re not hard to interact with and engage with.

Our strategy and insights team launched this product called The Breakroom, which is of the last Morning Brew survey that we sent out, we had over 60,000 people respond. It is also a sign of engagement and relationship. I forgot the exact number but a lot of those people opted into wanting to have a dialogue with us. This guy, Mike, created this thing called The Breakroom, which allows us to have an ongoing dialogue with some of our most engaged fans and people who want to be a part of the Morning Brew community and help us succeed. There’s no shortage of ways and touchpoints that we are talking to people.

One of Alex’s superpowers, which is then seen in all the mediums and how you communicate with consumers is he feels so relatable. It does feel like when he’s talking, he’s just talking to you and should reply.

He asks on all of his podcasts. There’s always a question. He is so good on every social outlet of being true to that word. It’s not like, “Here’s a question. I’m not going to respond.” He gives thoughtful responses to everything. On the new podcast that he’s got, Imposters, it’s all about mental health, entrepreneurship, leadership and success. It’s raw. It’s real. It’s not a type of medium because we’re doing podcasts but the way in which people are starting to talk about personal things and even topics that were once upon a time off-limits, we’re trying to break into. Alex has done such an amazing job at that. The way that he does it comes off so authentic. Honestly, it’s 100% of who he is.

That’s incredible. I’ve been a happy subscriber to the Marketing Brew newsletter. How do you determine new newsletters or content to start producing?

It’s a little bit different on the B2B and B2C sides. There is always a reason though for what we do. When it came to launching Marketing Brew and even things after that, our GM of B2B, Jacob Donnelly, has this framework that anything that he’s launching has to go through a few levels. We would be like, “Is this topic interesting? Is there enough to talk about? Is there room for us to be able to talk about it in the Morning Brew way? Is it completely flooded? Will we not be adding anything to the conversation?”

Another evaluation point is like, “Is there revenue opportunity?” There’s nothing that the editing side of the house that does that is influenced by me or anything like that but as part of an evaluation process, it’s important to know that that is something that can ultimately help make the company money. That’s not going to necessarily sway things one way or the other but it’s an important part of thinking through launching a new product because every product or every business unit serves a purpose and because our content is free, it needs to be ad-supported.

To that point, what is the main lead indicator of whether it will be a good revenue opportunity? Is it brand-driven and asking brands what they would want to sponsor or advertise in or is it consumer-driven and how you are going to build the biggest audience?

The reason why that part is last on the evaluation framework is that I’m a big believer that if there is the POV, if it’s an interesting topic and there’s an industry out there, there will be advertising and brands that care about that. If we did it the other way around, that would blur the sales edit lines. We’re not launching edit things for the sole reason that brands wanted it. It is a consumer base. We know that people are interested in these types of things, that it is an interesting industry and there is a story to tell. The revenue will come, If it doesn’t then our next conversation would be very different.

What’s coming up next for Morning Brew?

We’ve got more B2B launches coming up, which is exciting. Niche media is awesome. IT Brew is the next one that launches. After that, it’s going to be CFO Brew, which is super cool. On the B2C side of the house, we are talking to a lot of amazing creators and talent who have a community and voice. We brought on Katie Gatti who runs Money with Katie into the fold. We’re helping her grow her personal finance brand and franchise. We’re trying to do that now across the board with a lot of people who are talents that can create and has a POV. There are those two things. The last point is starting to do events. We’ve been staffing up an events team even during the pandemic with the expectation, hope and anticipation that one day, we would get to do stuff again. I’m going to South By. I’m very excited about that. Industry events are back. We think that that is a bright, big opportunity for us to do things a little bit differently. We’re excited about it.

Will there be a Morning Brew event at South By?

Every product, every business unit, serves a purpose.

No. There will be a Jason running around and trying to hold court potentially at different coffee shops and bars. There will be many micro Morning Brew events.

When you say B2B segments, is Marketing Brew considered B2B?

Yes. Anything B2B is going to be industry-focused where you can get better at your job or your role.

It’s not catering to a business but it’s catering to people in business.

It can also be a specific industry. Marketing is an interesting one because there are marketers in every industry and there is a marketing industry. As far as B2B goes, that’s vertical and horizontal. Think about a retail group. Those are hardcore people who work in retail. If you work in retail, that is a must-read. That’s the core to the DNA of what we mean by B2B in Morning Brew.

I need to check out all of the different newsletters, podcasts and videos. It has been so much fun watching all of you grow and consistently produce incredible, fun and interesting content as you go about it.

It has been a lot of fun to be here for the last couple of years. I’m looking at three years coming up in July of 2022.

The last part of the show is the lightning round. I got four questions for you. Answer with the first thing that comes to mind. The first question is what is your favorite youth sports memory?

I played hockey growing up. We had the ultimate underdog story at this one point. I played for the New York City Cyclones. We played the Brewster Bulldogs. To get into the state championships, we had to beat this team that was bigger and better than us. They beat us badly every time. It was like the Avengers End Game when Dr. Strange gave Tony Stark the, “This is your one chance.” We did it. I had a golden assist in that game. We beat them 3-2 in overtime. I can still see it so perfectly in my head and feel the feeling.

What was the move on your goal?

There was nothing pretty about my game. It was sheer will and determination. I bulldozed through people because I wasn’t fast but someone had dumped the puck in, goalie went out around the net to try to stop it. One of the guys on my line, Jake, was fast. He ended up getting the puck before the goalie hit it out in front. I was halfway falling and then we got the bucket in that.

The second question is when you were a kid, what did you want to be when you grew up?

WGP Jason Schulweis | Advertising And Media

Advertising And Media: We’re very aggressive when it comes to turning people who don’t engage and who don’t open.

It was either 1 of 2 things. I wanted to be a professional athlete as a kid who does not. I grew up in a household where my dad was an executive. I always saw the way that he spoke publicly and could command a room. If the professional athlete thing didn’t work out then I wanted to be like that.

You nailed that.

It’s still a work in progress.

The third question is what is a brand whose marketing you admire most?

I feel like a lot of people would say it but Nike. They don’t advertise products. The way that they advertise a lifestyle and perspective and also being able to advertise what you stand for and generate that type of emotion is great. Everything they do is gold. It’s incredible. The athletes that they’re able to tap into and sponsor are also the best of the best.

Finally, what is a go-to cause that you like to support?

I already give Phil’s Project Healthy Minds a nod. It was the Jewish Foundation for the Righteous that is evolving but UJA, which is the United Jewish Appeal of New York. It’s not just even about helping Jews at home and abroad. It’s the entire New York community and helping wherever and however. I’ve served on both the raising money side and distribution side for where those funds go. It’s an inspiring organization.

Thank you so much for coming to the show.

Thank you so much for having me. I had a lot of fun.

Me too. You were great. Thank you.

Thank you for reading this episode of the show with Jason Schulweis. As a recap, we discussed Jason’s background and how he got into advertising and media, how to give and receive feedback effectively and the incredible rise of Morning Brew which you got to check out. Thank you for tuning in. See you next time. Play on.

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About Jason Schulweis

WGP Jason Schulweis | Advertising And MediaJason Schulweis is the EVP, Brand Partnerships & Creative Studio. He joined Morning Brew in July 2019, and oversees two departments: Sales and the Creative Studio (Creative & Content Strategy, Branded Content, Research & Insights, and Production).

His team drives company revenue through native content campaigns that live on and off of Morning Brew’s network of media properties and platforms.

He previously held leadership roles at MediaLink, Live Nation, Thrillist and Yahoo!.

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