Someday List with Dan Toomey

This month, we had the opportunity to chat with Dan Toomey, a comedian, writer and video producer at Morning Brew, a media company with over 4 million subscribers across their lineup of newsletters. Dan has been integral in building out their video content and accumulated millions of views with his short satirical takes on business news. Today, we’re sitting down to talk about starting his career amidst the pandemic, marrying journalism with comedy, and preserving your creative well-being.

Check out some interview highlights below:

On the rare chance that someone hasn't heard of Morning Brew. Can you tell me a little bit about what it is and what you do there?

Yeah, Morning Brew, for the first six years of its existence, long before I was there, was the hottest business newsletter on Wall Street, covering everything from Wall Street to Silicon Valley and since then we've become more of a media company, which is where I kind of came in to start the whole video program at Morning Brew. That's what I do there is I make videos for them and now we have multiple newsletters. We have very active social channels. We're on TikTok, Instagram, Twitter. We're on YouTube that we're building out right now. So we're much more than a newsletter.

Prior to starting at Morning Brew, you studied journalism at USC and graduated in 2020, as if entering the workforce is not disorienting enough. Do you feel like starting your career amidst so much uncertainty has shaped your career outlook?

The pandemic hit and it wasn't a matter of like, oh, I need to craft my career path. It was like, I need a job. We were being advised not to contact the people who were prospective employers, because they're trying to take care of their families right now as should you. And I was like fair. So I graduated and my big thing was, I just finished four years of school. I gotta have a job.

I was applying to anything and I had this running list. It was like 80 jobs that I got rejected from. It was this big old spreadsheet of just red. These were mostly reporting jobs, but they were like in Anchorage and places I had no business being a reporter, but eventually somebody told me about Morning Brew, and at the time they were mostly hiring engineers, but they said, you should really check these guys out. They're really ramping up their newsroom. I followed them on LinkedIn, fast forward about two months, I had been freelancing for a website just doing copy-editing and writing, just to have money. Eventually I saw Morning Brew was hiring for a podcast host, they wanted to do a Daily Show-style podcast about business.

I really didn't learn anything reputable in college. I was a journalism major who liked comedy, but I was like, maybe this could be it. At the time I was making these in my college bedroom that were like John Oliver in 60 seconds. And I made one for an audition tape. Long story short Morning Brew was like, hey this is a podcast. Don't know why you sent us a video, but if you want to come here and do this for us then we would be down. This is all to say that I ended up in a position and I do think that what I do now is kind of like the modern version of what, a late night show does almost, it's just on a much smaller scale, right?

We react to the news of the day. We make fun of it. We have fun with it. So, it made me more open minded because it was proof that, you know, I thought I had a five year plan in college. It didn't work out, but in my opinion, it ended up being even better than what I initially wanted.

What does Dan Toomy's news diet look like?

I consume, just like anybody right now, I consume a very unhealthy amount of media. Honestly, you're catching me at a time where I'm trying to dial it back a little bit. Just because it was just getting to be a mix of overwhelming and feeling creatively blocked. And I had been reading a lot on different writers, processes and a lot of it was just like, yeah, you gotta step away at some point, and just breathe. But on average, usually I read the Economist and Bloomberg every morning.

Well, this is including my job because it is definitely a part of it, right? I came into business news, having had no background in it. So a lot of it's really educational for me a lot of the time. I read all the newsletters from Bloomberg, Matt Levine, the 5 things in the morning. I listen to Odd Lots when I go on walks. I try to read the front pages of the Journal, the Economist, and that's usually for news where I gather pitches throughout the day. I'm subscribed to too many, which of course includes Morning Brew. Not Boring I read, I read Scott Galloway's newsletter. I read the Axios markets newsletter. This sounds like I accomplish all these every single day. I don't, it's really just kind of jumping around. I'd say Matt Levine's is really consistent.

And then if you count Twitter as consuming news, I'm on Twitter all day, but for where I get my favorite articles from it's usually either Substacks from people that I know and I know they're really smart people. Like Kyle scan is one of them. Joey I've actually never taught.

I've never said his last name out loud. I think it's Politano. He has a great newsletter as well. They're both more economics focused. And then I also, I feel like it's so stereotypical to like Atlantic articles, but I love them. I just, I can't get enough. I love Atlantic articles because they feel like they capture the whole story. Derek Thompson is one of my favorite writers at the Atlantic. So it's a mix of just reading all of this throughout the day and then occasionally listening to podcast. But I prefer reading an article to a podcast.

So yeah, I'm sorry. This is too much news by the way.

@morningbrew Content creator’s existential crisis. #elon #pay #business ♬ original sound - Morning Brew
So let's talk about Morning Brew. Four million subscribers, profitable sense inception, recent acquisition by Insider. What has it been like to be on this rocket ship of a ride with the company since you joined?

We've hired a lot of people since I joined, which has been great and meeting so many new talented people and seeing how they can grow the company as well. It's funny, I have really occupied this space in Morning Brew where I've functioned in my own little silo almost. I think that it's part of this creator-first growth model that we've wanted to follow with hires like Sigin Ojulu, Anish Mitra, Money with Katie, Excel dictionary, and Jack Appleby. I just listed them off like we're the the Avengers, but yes, that's all of us I think.

A lot of it is what you see with other media companies right now where they're investing in personalities first and people first, because modern media looks more like influencers rather than this oligarch-like platform. And that's been interesting to see, and it's been encouraging to see as somebody who started off with this company really where it was me and our social editor and one other head of content. And that was our whole video team. That was our whole social team pretty much and we just started making stuff from there. So in terms of growth, it's been great to see other people be able to conform to that model or work with it and bring their own perspective to it and their own voice to it as well.

Also, it's fun. I'm not gonna lie. There have been moments where you do feel the pressure of like, okay, we gotta keep growing because we're out in front of people now and we're proving that we're here to bat with the big dogs. So we gotta make sure that we can pull our own weight. So it's a motivator too, if you want to be considered part of the Bloombergs, part of the Wall Street Journals, part of the CNBCs, you gotta make sure your shit's good.

You have to be able to put up quality work and if you don't, then people won't take you seriously. I think that we've managed to do that over the past year, while also having moments where we've experimented and been like, okay, that didn't work and moving on, but it's been exciting and it's been a massive learning process throughout the whole what year and a half that I've been here.

So as the company grows, do you think it'll begin to look more like a traditional media outlet or do you think more traditional media outlets are going to start taking cues from what Morning Brew is doing?

I think some have already, to an extent. We were not the first outlet on TikTok, but a lot of business outlets joined TikTok after we did, but you could extend that back to WaPo. So I think that we're all kind of changing together, and I'm viewing this from a video standpoint, right? My focus is video platforms, but we're not even talking about all of the newsletters that we've launched since. Austin could probably answer this better than me because he's been here since the jump. I only joined a year and a half ago, but I think a lot of media companies are learning from what Morning Brew is not doing right now, but what they've done over the last seven years which is scale newsletters effectively. And now, we are investing in creators heavily, which some other platforms, some other news companies are doing. It feels more like a blending rather than "we did it first and they're copying us."

I think we're all reacting to the changes that we're seeing and that really starts with the audience and the people who are making stuff too. But in terms of newsletters, I think Morning Brew was probably at the earlier side of that, but that's probably a prediction that I shouldn't be making since I think I was in high school.

You've hit your stride with these short form sketches that you do. You have the new sketch series that's on YouTube, Good work. I'm curious, were there any earlier experiments or explorations that didn't work out as well?

I was tasked with making our first video and I had this lighting setup that I brought from college that was way too big. And I was like, I'm gonna make a 16-minute investigative, John Oliver style monologue. It was about why Tesla had Bitcoin on their balance sheet, which is too on brand. My room was so small that I had to put my mattress, which did not have a bed frame, I put the mattress onto the wall and I moved my desk to the middle of the room. Then I put up my lighting set up, film this whole thing, edit it down to 16 minutes. We put it on Instagram of all places, and no one watched it because, why would they?

At the time I was like, okay, I'm gonna come out strong and this is what I'm gonna do for my first thing ever. So nobody watched that. We did another one that was shorter, but nobody watched it again, because it was five minutes and then, as a promotion for another monologue-style video, we made a TikTok. It was a little sketch that was the stages of a startup going from seed to IPO. And that video that we put on TikTok to promote a different video, got half a million views or something like that. The actual video was garbage. Nobody saw it. So we were like, oh, this is what we should be doing. And I've said this a lot, but the philosophy that we've abided by is like we're down to try anything, but we only repeat what works.

So there's a lot of experimentation and encouraging to be creative, but at the same time, if we know that we have a hit, we want to try it a few more times. Not to the extent where we exhaust ourselves and people only know this is the outlet that does this one type of comedy video. But there were some early experiments that were definitely not the direction that we should have been in at the time, but we learned a lot from it. And those are valuable in their own right.

Good Work is the new sketch series on YouTube. They're four to five minutes as opposed to the minute, minute and a half that you do on Instagram and TikTok. Do you find that you like writing for one format over the other?

I kind of like both. One of my life goals, I'd say like long term, is to write for television. I really enjoy writing for Good Work because these are actual scripts that we're writing that are formatted like scripts and that's great.

I just enjoy having that be part of my job and being able to practice it consistently and get better at it. What I like about writing for TikTok and Reels is that you kind of treat them like short stories almost. Where you can take massive swings with a concept and you don't really have to explain everything that's going on and people enjoy that. You can get crazy and weird, you're supposed to kind of get crazy and weird or you have freedom to, and people will be very forgiving.

Good Work is definitely more of a challenge sometimes, but we have people on our staff that I collaborate with. And it's just more of a challenge I would say. And again, for somebody who wants to write scripts for a living in the future this is just like a closer step to that.

You put out an incredible amount of content at a relentless space and it's all very funny. How do you structure your time and protect it one, for your own mental wellbeing, and then also for your creative wellbeing?

I'd say a big part of it is leaning on people that you trust and that you can toss around ideas with. In addition to Morning Brew, I put videos on my own Instagram and a lot of those ideas come from me just kicking it with friends or my brother, and we just talk about what would be funny and sometimes the urge to make something off of an idea is so much that you're like, I have to do this. I will spend my Saturday or my Sunday doing this video because I just really want it to be out there. And it's fun too.

In terms of structuring my day, it's varied since Good Work has entered the picture. I made it sound like a child. It has changed because Good Work is so different. Like I have spent multiple hours today editing our last video. Probably a year ago, my whole job would just be to make a TikTok for today and then move on and then do the same thing for tomorrow. Just rinse and repeat. So now we have a cadence of two to three videos a week while editing these larger scripts for Good Work.

We have another interview show called Office Politics, but to be able to keep up that cadence I'd say one, you really have to like what you do. Fortunately, I really do and that makes it easier because this is the stuff that I was doing in my free time when I wasn't working at Morning Brew.

So that's part of it, but in terms of creative exhaustion, I think it's really important to recognize when you're burnt out. And I have not been great at that. I really have not. I've had people who have had to tell me that I am clearly burnt out and I have had to take steps back and be like, okay, you're right.

Because it's one of those things where mentally you're like, I need to keep going. And if I don't have an idea now I'll sit back at my desk, I'll write out 50 ideas and one of those will be good. But if you're in a state of being burnt out, and your censor is louder than the part of you that's enthusiastic about making something. None of it's going to be good and it is hard to pull yourself away.

But when you do, even just a day or two or a weekend where you're like, I'm not going to try to write anything. I am just going to take this time for myself, then you get back and you're like, oh wow. I'm in a much better headspace than I was previously. Therefore my ideas are just better and more fun because I'm actually having fun with it again. So it's a mix of leaning on people for inspiration because a lot of the best ideas come from you just, again, kicking it with people that you normally joke around with. And then also, self care which I'm not always the best at, but I'm learning and I'm relying on people for that.

You're not just exploring comedy at Morning Brew right now. Outside of it, you are doing improv and stand up. Are there certain things comedically right now that are really fun to you?

I mean, yeah. So right now, I should be doing more but I've been doing standup in New York. Seeing how social media has impacted the standup and open mic world in New York is so interesting to me. There are a lot of ways, but I also want to write a script about it. So I shouldn't say too much. I hit open mics consistently. I'm not nearly as good as a lot of the people that I hang out with, but I meet a lot of other standup comedians through that process and they've become really great friends since I've been here.

So that's a really fun element to it is just this whole new friend group that you develop. You're going to look this up later and talk to other standup comedians like, oh, Dan Toomey? I hate that kid, he's the worst, but no, it's been humbling and it's been a blast.

And then I go to improv jams, and just the amount of shows. That's one thing, there are so many shows I want to go to throughout the whole week, but you do get choice paralysis often where you're like, do I write a humor article? Do I go to a show tonight? Do I practice standup? Do I do improv? Which is great because there are so many outlets, but you can definitely freeze at some point and really not know what the best direction is. So yeah, it's still been fun.

I really admire that openness to trying and exploring everything and this fearlessness of failure. I'm sure it's still uncomfortable, but you're out there doing it.

Who said fearlessness of failure? It's weird. I get what you're saying, right? It's kinda like that voice that we talked about earlier, the one that's just like, you have to do this. That voice doesn't come without a fear of failure. I think that you're often scared of failing in whatever medium you put your heart into, which is what art is at the end of the day. Not saying that what I do is art, but there's certainly the anxiousness of, oh, this might not go over well. Oftentimes the payoff from it all will make up for that, you know?

So I think that sometimes there's this misconception where people are just like, oh, like these comics get up there. They're just fearless, they just get up there and do that where it's like, no. Oftentimes, I feel like it's like going to the gym where you're just like, this is going to suck. I don't want to do it. And then after, you're just like, oh wow. I actually feel better now. So. In my mind, that's often what it comes down to.

I do think that whenever I have been anxious about putting myself out there more. Oftentimes, the product of that has been good for me. And I think that you can become very isolated in this job where you're like, I'm just gonna stay inside and make my little videos and I don't know how healthy that is. So, through doing stand up and through doing improv ironically, it's actually been a healthy experience because you're just like, wow, I'm out here in the world actually doing something. And you become a better writer and stuff like that through it all too.

Dan, thank you so much for being here. Where can our listeners find you online?

They can find me flooding their for you pages at the Morning Brew TikTok. And they can also find me @dhtoomey on every social platform. So Instagram, Twitter and I also have a secret handle on medium, but I'm not going to reveal what that is.

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