Memorial Day Special: Get to Know Toby and Neal

0:28The best B2B marketing gets wasted on the wrong people.

0:34good morning brew daily show i am neil freiman and i'm toby howell neil today is a special memorial day podcast it's a holiday which means there's not our typical news diet to consume so we decided to shake things up a little bit a lot of you guys have probably been listening to us for over 60 or 70 episodes at this point. Thank you for that. But you might not know a whole lot about us. So in the interest of getting to know your hosts a little better, Neil and I are actually going to interview each other. Yes. We're in a new studio. We're on couches with ferns behind us. We've had a few cold brews.

1:12So we're a little loose. I'm super excited to get to know a little bit more about you and our listeners too. I'm excited as well. We're going to get deep. We're going to talk about our past and hopefully you guys enjoy it. It's Monday, May 29th. Let's ride.

1:33All right. So for the first half of the show, I'm going to interview Toby, Toby Howell. The one and only. The one and only. All right. So to start it off, just tell the people how you ended up in the co-host chair next to me at the morning brew daily podcast. And I know this could be a long story. So maybe start in Portland, Maine in 2019, 2019, 2020. Yeah. So I graduated college in 2019, classic college story where I had no idea what I wanted to do. So I moved to Portland, Maine of all places to work at this small sports marketing startup. Um, and while I was there, that's when I started reading the morning brew.

2:13And actually one of my friends said, Toby, you got to check us out. This sounds exactly like you. You got to start reading it. And I did. I became obsessed with it and started trying to figure out, all right, this is where I want to be. This is where I want to work. How do I start working there? And so I actually cold emailed Austin and Alex, who founded The Morning Brew. I pitched you guys on a sports newsletter at first, which was, I thought Morning Brew should have a sports newsletter. Basically, you guys said, we don't really want a sports newsletter, but feel free to come in and audition or apply for the writer's role.

2:48And so I did that. I wrote a couple of newsletters, actually like fake newsletters, sent them to you, Neil. And then I hopped on a bus from Portland, Maine to New York and interviewed for the job. And a few days later, I guess I passed the test and was hired as a writer. So Neil actually hired me in my first role at Morning Brew as a writer for the newsletter. Yeah. I remember reading your, uh, pitches, your, your newsletters. I think I was like pretty buzzed on the, on the subway writing and I was reading them. I was like, man, this is really good. And I remember emailing Austin being like, we got to hire this guy.

3:25Let's go. Thank you. Whatever, whatever you're drinking that night. I appreciate that. Um, but then, yeah, I actually left morning brew for a little bit and then came back Austin, who is the CEO of morning brew is like, Hey, we're starting this podcast. Like you want to come audition like Neil is doing it. And it sounded really fun actually. So just one day I came in, we did a test run actually in this very room and one thing led to another and the podcast launched. Was there ever a, you know, a moment in the back of your head where even before this happened, where you, you know, you were like, I want, I want to be a podcast host.

3:59Literally not even for a single second because we were both like writers. We're both used to being behind the keyboard, behind the screen, I truly thought I was not a very compelling person on air or on video or anything like that. It just felt like one of those skills that just wasn't going to achieve. But then once the opportunity came, I was like, oh, what an awesome chance to actually hone this skill. If I don't think I'm great at public speaking, what a great way to improve upon that. So it became this really exciting thing, exciting tool to add kind of to the toolkit. it. So looking back, I'm super grateful for the opportunity, but I had no idea or inkling whatsoever that I'd be a podcast host.

4:39Do you feel like you've improved as a speaker from doing 60, 70 pods? I mean, I would imagine it's hard not to, if you do something every day for 60 or 70 times in a row, you're going to get better. So maybe off the top of my head, I can't think that of a specific thing, but honestly, certain things like getting information across in a clear and coherent way, I think I've improved at. I think it's made me a better writer too. I don't know if you felt that as well, because you just can really, when you have to speak about something, you truly have to understand it versus writing. We've talked about this.

5:16You can kind of get away with not fully understanding it. So I think it's just made me a better kind of distiller of information in general. All right. So I want to get away from the podcast a little bit and go back to your college days. So you were the captain of the Brown soccer team, which is a division one soccer team during college. How did that shape your college experience? Like, did you ever wish for a more normal college life? No, honestly. I mean, when you played sports growing up and I mean, I played sports kind of all the way into college. It was just so a part of my life that it wasn't the sort of thing where I felt jealous that other people were having more fun.

5:55Like it was just literally an integral part of my life. And then also, yeah, we still, still had fun. The one, the one thing that sports did through college that I think hindered me is when you go to college and you are on a sports team, you have a preset group of friends just waiting there. Like you'll have 20 to 25 guys that you know are going to be your friends no matter what. So what it does, it makes you less inclined to like go out of your way and socialize with other people. So I think I only really figured that out. Like my last couple of semesters that like there's this whole wide world beyond just like the world of athletes.

6:33And I feel like I missed that a little bit. So, yeah, I have zero regrets. It was like awesome. I wish I could keep playing to this day. But my, my one regret was like, I should have been a little better about, uh, you know, meeting other people. Was there ever a time where you thought you could go pro? Yeah, I thought pretty much up until my last semester, senior year of college, that there was potentially a chance. Like I had a decent junior year. Um, I knew I could probably play at a very fringe fringe, like MLS level. There was a very outside shot of that, but I probably could have played at one level beneath the MLS.

7:16So like USL championship. And then my senior year, my body kind of started breaking down, like the injuries caught up and it quickly became apparent that that was not going to happen. And I made peace with it very quickly. But literally until that senior year started, there was a small part of me. It was like, I, if the opportunity is there, like I'd love to do it, but it seems like it's came and went. Yeah, well, besides soccer, you run a marathon, you run triathlons, you played high level sports. I'm just trying to figure out what motivates you. You have such a competitive gene in you that I think most people don't.

7:53You literally ran to Yankee Stadium from the East Village for a game when we all, the rest of us, took a subway. So like what is it about you that makes you so competitive? I kind of think it's very fun to be good at everything. And so I've also often wrestled with this in myself. to me it's competence versus like depth of of understanding of things like some people they devote their entire lives to one thing they became they become incredibly good at it i've always thought it was very cool to step into a room step into any situation and just be like pretty dang competent at it and so like for the marathon thing surely the thing that motivated me was I want to step up to a 5k, like the 4th of July 5k or a turkey trot and like have a chance of winning it.

8:40I just think that's cool to have like that fitness in the back pocket. So it's this weird thing. I know it's, I don't know why, but I just think it's fun to be able to like pick up a Rubik's cube and be able to do it. Like have a New York times crossword and be able to do that. Like there's all these things that I think are such cool skills and I've just been kind of accumulating them over time. Again, this is why podcasting is cool. Being able to speak well, that's, that's ironic that I stumbled over that, but I just think it's very cool to accumulate different skills and different things and just be able to be competitive, be good at lots of stuff is something that has always kind of drove, drove me.

9:18So you have two siblings, right? Yes. What, to what extent does competition with your siblings drive your, so my sister was an incredible runner growing up like really really fast and she's two or three years older than me and obviously she I took like a while to grow into my body a little bit so she remained faster than me for a long time and I definitely there was a moment where I went on a run where I finally realized that like oh wow I was faster than her so that drove me for a lot and then of course when you have a younger brother that's someone just pushing you from behind he quickly became faster than me like also played soccer they both played soccer so i was being pulled by my sister and pushed by my brother so obviously there's some competitive juices there i mean it's always been very like love like we never truly truly went at it but those are two massive forces on the competitive was it like a gronkowski household yeah not as much uh body mass but as much competitiveness for sure so there might be people out here listening to this being like i'm listening i'm hearing toby and he's running marathons.

10:22He's solving Rubik's cube. So what would you, what's like one piece of advice you would give to someone who maybe runs three miles, exercises three days a week, but they look at something like a marathon or even a half marathon and they get super intimidated. You know, what, from someone who does not get intimidated by that, like what would you tell them? I'm going to give really counterintuitive advice because typically the advice would be like, go at your own pace, like just do what you can do on a daily basis. And which obviously that's great advice, but I actually think set an incredibly outlandish goal for yourself where this was my first marathon.

10:57I tried to break three hours in it. I didn't know if I could, like, that's a pretty hard, it's six fifties per mile. And I think by setting that goal, you just end up rising to that. And so I think if your goal is to just get off the couch a little more, set like a crazy 5k time or a race time and use that as like the the carrot in front of you because i i just swear once you frame the goal in your mind you frame the mentality that i'm going to achieve this your training will like you'll just pull yourself along um yeah which is not the advice that you'd probably hear most people say like if you run one mile then run two miles and then three miles but that will that will take care of itself once you have like the goal in place i think all right i've got some rapid fire questions to end our little segment here.

11:48So we talked about you becoming, you know, pretty adept at a lot of different things. What is one thing that you, if you could become elite at instantaneously, but you suck at right now, what would it be? Oh, I think it would be being able to step into a kitchen environment and open a fridge and just know how the ingredients work together, just like throw a dish together. I think that is so cool to just understand just like the science behind it, like how flavors interact, how to layer flavors. And I've watched a lot of cooking videos. I've done a lot of cooking and I'm, I'm going to, spoiler alert, I'm going to ask you about cooking coming in the next half of the show, but the ability to step into a scenario, open a fridge and just whip something up, I think would be the coolest thing to have in the back pocket.

12:34All right. What is the worst investment decision you've ever made? Okay. So I accidentally bought so many shares of Sherman Williams. This was, this was back in college where I read something about how like home improvements booming or something like that. And Sherman Williams is well positioned to actually company. Yeah. The paint company. And so I tried to buy like 10 shares of it. I accidentally bought$40 ,000 worth of Sherman Williams stock. I bought it on the margin. Cause like, clearly I didn't have that in my account. I was in college. And so I get margin called basically. And so like quickly have to like sell it off, like blah, blah, blah.

13:11Luckily it went up like the next day, but here's, that actually wasn't the worst investment decision. Sherwin Williams has absolutely crushed it. The pandemic happened and like paint became this huge industry because home improvement. If I had just not, if I had held the bag, if I had like paid the margin, uh, like interest on it, it would have been worth like five times what it was. And instead I like panic sold it all back. So it was two bad investment decisions in the span of 24 hours. And all my friends constantly, whenever they see a Sherwin Williams story, they go like Sherwin Williams, Toby.

13:43All right. That's for our listeners. You got to tease Toby about, uh, Sherwin Williams. All right. Two more. Is there a piece of art, whether it's a book, song painting that has stuck with you or is especially important to you? it's it's probably book um i i really i grew up like reading tons of tons of books um the one that's most recently stuck with me is probably this science fiction book foundation and it's one of those things i often joke about this where like sometimes you read something and you're like there's no way that person has the same brain that i have because like how can they piece together something so incredibly complex?

14:20How does this just emerge out of them? I guess that's another skill that I'd love to have, just like that ability to create these incredibly intricate stories. So probably, yeah, like Foundation or Dune, some of those like OG, OG science fiction books just really, I don't know, make me romantic about like the ability to tell stories. All right. Final question. You have a kid, okay, in the future, and you put in front of them a tennis racket, a soccer ball, a golf club, a baseball bat, a basketball, a football, or in the hockey stick, which one do you hope they pick up first? I think it's gotta be golf.

14:56Honestly, just because like, what a great thing to share with your child. Like it, I think golfing, I, you and I both love golf so much. It's obviously just like the worst mental sport out of all those, but even more so than soccer, like the fact that you can share golf with, with like your kid for so many years, I think actually it's just a really beautiful thing. So I hope they pick up the golf club, Neil, great questions. Oh my gosh. You told me you had some good ones prepared, but you're, you're fantastic. I think we should just end the pod. I don't think I could, you were so compelling. I don't think I could be near as interesting as you.

15:30That was fantastic. That was the first half of our show. Uh, before we jump into me interviewing Neil, we're going to take a quick break. All right, Neil, it is my turn. You were a fantastic interviewer. Um, But I now want to learn about you and your story. So we kind of started with me about how I ended up at the brew. I would love to hear about your brew origin story because yours truly goes back to the beginning. And I'm just going to add a little bit of context, but you actually weren't Alex and Austin's first choice, were you? No, I'll get to that. Just like you, I graduated college, University of Maryland in 2013, had no idea what I wanted to do with my life.

16:08I was like, I like reading and writing, but I don't think I'm that good at it. So I taught for a year in North Carolina and then I went to Temple University for master's in geography and urban planning because that is a passion of mine. I just love walking around cities and learning about spatial features and looking at maps and geography. And I was like, all right, maybe I'll pursue that as a profession. So I did that for one year and I just saw a LinkedIn post by Alex Lieberman saying they were looking for not a writer, but a content creator. That was the words. And for their newsletter, which was called Morning Brew.

16:43And I had heard of Morning Brew through some mutual friends. I did not know anything about business. I did not know what an IPO was. I did not know who Warren Buffett was or why he was famous. I kind of hated all of the business school students who were my friends because they didn't have a class on Friday. And I was like, you guys don't learn anything. You know, what are you doing doing business? You know, you can just kind of learn that on your own. And I just didn't really have any intellectual interest in it, but I read the newsletter and I just thought to myself, like, I could do this a little bit better than it is now.

17:17Um, I grew up watching Colbert report and, you know, people making the news interesting and fun for people. And that just kind of synced up with what I thought I was kind of good at and what I really loved doing. So I just emailed Alex and said, you know, I think I could do this. I'm going to apply. And I went through the application process. and I did not get it initially. I did not get it. They went with another guy and I just remember getting that email feeling pretty deflated and I just emailed Alex back. Super nice note. I guess this is a lesson to just be kind of cordial even in rejection and just said, yep, I'll be around.

17:56Get in contact if you want and then apparently they couldn't reach a deal with the other guy and so they called me up and then I got to work with my friend who was writing the newsletter at a time, Mike Schwartz. And, uh, we started cranking out newsletters for the next six years. It's crazy. Yeah. Wait, so this was 27 summer of 2017. It's wild. Neil has been at the morning brew since like almost the very beginning, kind of crazy. Um, that, that is just an incredible story. I can't imagine how different your life would be. And then also how different morning brew would be because your fingerprints are all over this company basically.

18:30Maybe I guess, uh, It is crazy. I just feel like it's a dream job and I can't imagine doing anything else. And it just, if I hadn't seen that LinkedIn post, you know, it's just so crazy. Like you can't, I guess it's a good lesson and just kind of, things won't come to you. You know, you have to go out and get them. And I never would have worked here and my life would have been probably way worse than it has been if I just hadn't, you know, took and taken a little initiative and, you know, follow it up with Alex in that particular way. Um, so it's just been a huge gift. Yeah. Awesome story. But let's remove a little bit from the brew universe, talk about you and your personality a little bit.

19:12So two things that some people might not know about you is one, you love classical music and then two, you also love cooking. And so these are two, I love these two interests because they're very, you can cook while listening to classical music. It's great, but I do actually want you to talk about where does that come from? Because you actually are a person who has many interests, similar to me. And so where do these more intense hobbies or interests come from? Classical music has been a big part of my life since I was a young person. Three years old, my mom signed me up for piano, classical piano.

19:48And our town, Longmeadow High School in Longmeadow, Massachusetts, had a really good orchestra with a very good conductor. And my mom was like, you need to play an instrument to eventually be in this orchestra. So my mom was like really adamant that I play an orchestra instrument. So she signed me up for cello in addition to piano. And I would hate it. Like I would cry. I would sit in the car and just cry not going into early cello lessons. And she would just be like, you'll thank me later. You'll thank me later. You'll thank me later. And then eventually it got to the point where I started practicing because I enjoyed it, not practicing because my teacher would hate me.

20:28And so when I got to high school, I mean, I should say I am not good at I'm very mediocre at piano and I am not particularly good at cello. But being in the orchestra, I have all my friends were in orchestra. We played at Carnegie Hall. We played at Boston Symphony Hall. and so I kind of just fell in love with the music um while while playing uh in the orchestra and you know all my good friends are we ate we I shouldn't admit this but we ate in the band room uh in high school and lunch because you just yeah we were just like hanging out and uh you know I love that uh and and we were just all uh yeah you could go on the computer there that was a big thing yeah but then what about the cooking aspect too I don't know I don't also I should say I'm not I don't think for how much I cook.

21:12You're a pretty good cook. I'm okay. You do a lot of different dishes, which is more than I can say. For me, cooking and food is like a aperture into other cultures. And that's the part that's so interesting to me. When I travel, I drag people along to really weird places where I can eat really weird food. I don't think there's any food that I wouldn't eat. Like I eat, you know, brains, testicles, worms, you know, whatever it is. I, for some reason, I'm just kind of gravitated to that. And I, a big inspiration for me was, uh, Andrew Zimmern on bizarre foods. And so he goes out of his way to eat really weird foods.

21:47And he uses it as a way of saying, look, we have all these things in common, uh, between cultures. And so I, you know, when I love going to markets whenever I'm in a city, um, to like really hole in the wall, uh, places. So I, you know, I really love traveling and I think food is just kind of a vehicle for that. It's kind of famous around the brew, how much you do work. Cause you are now running this daily podcast. You've been at the helm of the newsletter for the last five or six years. You do, you have very long nights. You do not take a lot of days off. Do you kind of take a step back and, and realize like how much you're working and then what kind of drives you and kind of propels you to do as much work as you do?

22:28Yeah. I think if I reflected on it, I, it would freak me out. Right. It would freak me out. So I try not to do that. Um, I think a big reason for it is like, I'm single. I don't have kids. I don't have like responsibilities other than myself. And I think if I had all of those, you know, a family in my life, I would, I think I would absolutely work less or find ways to work less. But for the past six years, I've just kind of devoted myself to this work. And I think a large reason for that is that I really enjoy it. Like Like maybe in my spare time, even in my spare time, I was reading the news and writing, you know, and now I get paid for it.

23:04And now I get paid to talk about it. So these are all things that I was kind of doing on my free time anyway. And now I'm getting paid for it. And it's not as romantic as it sounds. But so I think the type of work kind of leads itself to working really hard. And just the family I come from. I don't want to call out my parents, but like they worked a lot of hours and they still do. Like my mom is like, you should stop working. And I'm just like, you're still working. you're working. Like, what are you doing? What are you telling me not to? So I come from a family of, uh, mostly workaholics where we were just kind of like grinding and doing stuff we liked for, for many hours over the course of the day.

23:39And so it just feels natural for me. And when I have an evening where I'm just like, you know, or a day where there's not, you know, I don't have work. It kind of feels a little weird to me. Yeah. I, that's extremely unhealthy. No, but it, honestly, I, it is inspiring. And I think it's one of the reasons why you've been like a leader at Morning Boo for so long is that it's very easy to look at you and say like, Neil is putting in the hours, Neil is putting it in the hours, but also producing a great product. So it's always been something that like motivates me as like your partner in crime, um, just your, your work ethic.

24:11But then a follow-up to that is you are knee deep in the news cycle every day for the last, yes, six years. How have you kind of combated burnout? And then also, do you ever feel like it weighs on you a little bit? Cause a lot of people associate news with negativity and there's just like so much heavy stuff that you kind of have to parse through. You went, you navigated an entire pandemic, you've navigated like election cycles. Do you ever feel like that's weighing on you or do you just kind of power through it? Um, I don't feel burnout. Um, I get excited every morning to wake up and do the newsletter or talk about on the pod because every day something's different.

24:51And that's what I love about the news is you wake up and you're like, who knows what's going to happen today? Apple reports earnings, but who the heck knows what they're going to say? Who knows what bank is going to fail? Who knows what Jerome Powell is going to say? Who knows what's going to happen across the world? There's so many interesting things happening all at once. So it never feels repetitive. There's always people writing interesting things that you can draw on. There's always arguments being had that are really interesting to draw it. So it never gets boring for me. I think it's the nature of the job is that you report on the news and the news is new.