Ep. 89 How To Make Sure Mondays Don't Suck With Timm Chiusano

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1:28Tim Chisano is corporate America's Batman. by day he's a VP at a fortune 100 company managing a team of over 200 people plus an eight-figure p &l by night he's a tiktok star with over 1 million followers and 50 million likes tim is an incredible person this was a really really interesting conversation and i cannot wait for you to listen to this episode just worth saying this is another episode in our new york series obviously and there was a little bit of street noise one thing i will say about new york because they need to sort out their sirens. As someone from the UK, what is wrong with one uniform siren sound?

2:03It honestly, I, until you've heard the sirens here, you truly will not understand. But there's a little bit of that in this episode. So we've tried to deal with that as much as possible. But there might be a little bit. So sorry about that. Before we get into the episode, please do make sure to like the video and subscribe to the channel if you want to hear more interesting conversations. It hugely helps us be able to get incredible guests on the podcast so that we can have these types of conversations and learn from these types of people.

2:30thank you so much for joining me thank you so much for having me honestly when this popped up i can't tell you how honored i felt especially given the context of the conversations that you have like this is i'm so excited for this oh thank you so much i mean we've already had a good conversation so far absolutely and i feel like there's so much i want to discuss with you I think what you've put out there in terms of your content is so impressive and also so refreshing in so many different ways. And I want to dive into some of those topics. First of all, I'd like to ask whether you feel like at the moment you are more working hard or hardly working.

3:09I am definitely working hard right now to the point where this might be the most exhausted I've been. Really? Oh, yeah. No, it is at a fever pitch at the moment. but at the same time too that makes it like it makes it feel like I'm hardly working in some cases because when I do take a deep breath literally when I walked in the door here just sitting down and when you can be as exhausted as I feel right now but at the same time energized and excited and genuinely happy it can feel like you're slacking at the same time but my days are nuts right now I've I think I've found full capacity really yeah I mean I've I've watched your vlogs and it it looks full capacity to me it's giving very full capacity energy um but no I think it's incredibly impressive and I think that it's important to note that difference between how you feel like you're executing and how you actually are and knowing like what some of my biggest frustrations come at a point where I feel like I'm working really hard but at the same time I feel like I'm kind of spinning the wheels.

4:14Like I feel like I'm also, you know, probably because so many things are going on that you can't really recuperate and check in with, okay, well, this is moving in the right direction. So is this, so is this, but which is why I try and keep this like mindfulness around like, what is the biggest priority right now? And how am I getting towards that? Because everything's a whole little bit crazy. And like, you need to keep that just like awareness of where you currently are. Yeah. I'm doing the same thing, but almost to a fault where the priority becomes the next thing that's coming in versus what I should be planning.

4:51I've actually, I did a, I did like a 35 page PowerPoint deck for myself just to map out not goals for the year, but just what do I need to do to continue to progress things? Because I already time block basically in 15 minute increments from four till 10 ish. I was like, all right, how do I get the whole smarter, not harder thing? Right. And it can be super annoying when you're like, wow, there's actually room for improvement here, but I'm still too reactionary. And I think that that's where the working really hard has gotten past the point. But I think it's a fair statement that I'm carrying three jobs at the moment between the corporate job, writing a book and the content creation, especially with representation now that brings in actual deals that are, as you know, like their own projects in and of themselves outside of the organic and the organic's got to stay tried and true or else you just have a feed full of ad or it just, it just doesn't, the rest of it doesn't work if you're not doing the organic stuff too.

5:55So it legitimately feels like three jobs right now. Yeah, No, I can completely understand that. And I do think that social media very much adds into that because it kind of almost has to be a byproduct of what you're doing rather than the only thing you're doing. Because otherwise, you know, it can get quite repetitive and you can feel like it's you're only talking about doing social media. But at the same time, it also like it has to be reactionary and it has to be on the spot and that can get pretty difficult. Yeah. I'd like to give anyone who isn't familiar with who you are and what you do some context on your past and how you got to where you are now.

6:35Could you give us a little bit of a whistle-stop tour of your, literally your entire life journey in some sort of concise representation? Yeah, totally. raised by a self-proclaimed old hippie, which would be my mom, airline stewardess turned artist. My dad was a radio executive, started in sales, made his way up to radio executive here in New York for the most part. Most of my family roots are here in New York City. I was a very bad student in high school. By bad, I mean, I was the kid that they were like, We think he's smart, but he's super tuned out and doesn't seem to try very hard. I just couldn't monotask.

7:21Love Sports was okay. I decided to move to Canada when I was 17 because I didn't want to go to the schools that I could get into college-wise at the time. And found this school by mistake in Port Hope, Ontario that just checked all the magical boxes. So I was a New York kid that moved to Canada to play a bit of hockey to try and improve grades. kind of worked out, kind of didn't. Spent five years up there. My dad almost died of stage four cancer when I was 20, 21 years old. That steered me in a slightly different direction for a bit of a longer story. Got out, faked the fact that I had no college degree, got a substitute teaching job and a couple other part-time gigs, eventually landed with ABC Sports, did that for five years, got married, panicked, pivoted to a more traditional desk job at ESPN, then got an email out of the clear blue sky for this current job 11 years ago.

8:19And now I'm sitting with you. Well, that was very concise. I'm incredibly impressed. That was, yeah, that was very well done. I'm really interested about this evolution from being almost in one career and moving to another career. I think that we, you know, we're getting better and better at seeing careers as not necessarily linear and able to kind of, you know, not necessarily jump ship, but be able to steer ourselves in different directions. But I also still think we, you know, fresh graduates have this anxiety about getting into the right job and making sure that your job is your career. And a lot of what I talk about always is understanding that, you know, especially in your 20s, you do not need to be in your career.

9:04You need to be building skills and just being, you know, getting more and more aware of what you enjoy, what you're good at, what types of work, you know, you feel most alive in. I'd love to talk a little bit about that and the move from sports to, as you say, a more traditional desk job. You say you panicked. Was that specifically a panic reaction? It was specifically a panic reaction because I just got married and the sports gig was live sports production for ABC, which meant traveling 36 weeks a year because you're always on site. being a newlywed and traveling that much just felt and even though we had met on the road we met through work in las vegas of all places and and as i mentioned before married within seven months which is just um one of my favorite parts of like the entire uh anthology of of what's happened over the past you know 30 years at this point and it was a i can't travel that much and feel like I can really, this just doesn't feel fair.

10:05Like I want to be with my wife. I didn't get married to just be like, cool, now let me keep going and doing my thing. And I'm so glad in hindsight that that hit me and it hit me immediately. So the panic was, I've been doing this for five years. Live sports production can be extraordinarily, you know, you can be pigeonholed. It's such a specific skillset and it's such a specific arena. It doesn't translate the same way that if I'm a marketer, I can kind of jump from company to company. And thinking about things broadly, it forced me to figure out what are my macro skills. And a lot of the things that we'll talk about today, I was not smart enough to know back then or be like, oh, here's how I'm going to plot this out.

10:48But I just had to figure it out. Now, in hindsight, I'm like, oh, that's what I did. And some of the things that work, like being able to get myself out of live sports production into marketing. And I think anybody could take a look at where they are, where do their broad, not like the specificity of I'm here now, here's the next rung in the ladder. Where are the macro skills that are bringing to the table? Where are the broader business problems that that could potentially solve for? And that'll start to open up your mind to all kinds of different areas. But to your other point, Like your first job is not going to be your last job.

11:23Like I've had three pretty big career pivots at this point. And I'm going to make another like really big career pivot as well. So don't people get so stuck and then they feel like they're in this vertical when it should just be about what are you capable of and what makes you happy. And then it kind of opens up more broadly from there. Yeah, no, I completely agree. And I think one of the best pieces of advice that we've ever had on this podcast was in the first ever season. It was like right at the beginning before the podcast was video or anything. And this incredible woman called Shopee Delano was on the podcast.

11:58And we were talking about building your career, particularly in your 20s. And like what you should be doing within that time to get you further in your career. And all of it was based on the fact that actually what you should be doing shouldn't be about being in the right career. it should be about building the right skills on someone else's money aka your yeah you know totally the organization's money like if you can spend time within your 20s understanding to a fault what you're good at as you say your macro skills what do you bring also what you enjoy upskilling like I always say if anyone's going to pay for your training take it like do not turn down that opportunity even if you have to sit there for a day watching stupid at little videos like the more you can build that the stronger you become in terms of you know a resume isn't just a list of jobs it's very much a list of skills and if you think of the concept of like writing a cover letter the way I always recommend to do it is to look at the job description highlight the things that seem like the main skills they're wanting and match it up to where those skills have been in your previous jobs even if it is an entirely different industry And the only way you can do that is if you are getting those skills, like you are upskilling, you are spending time refining who you are as an employee and what you bring.

13:17And of course, there are so many different types of organizations and so many different sectors and so many different types of careers. but actually learning what you're good at and what you enjoy on someone else's money should be everyone's concentration being in any sort of organization personally I believe for the first good while and it also removes the concentration on making sure you're in your dream job I think there's so much we'll come on to think we'll come on to talk about as I said like seeing your life beyond your youth and seeing your life beyond this idea that it must you know end at 30 as we kind of seem to imagine on social media, that is, in my opinion, the best stead you can put yourself in.

14:01And it sounds like rather than a, yes, you had a career pivot, you didn't necessarily have a skills pivot. And that is how you can dance around literally any industry by just making sure you are building those and therefore, and then just telling people why you have them and why they're going to be perfect for that job role they're specifically hiring. Yeah, a thousand percent. I mean, the skills and purpose, the two themes that we're talking about now, like from a skill set perspective, I think another key thing that people overlook is the, especially with a sports analogy in mind, when they're stuck doing Excel spreadsheets or they're stuck doing presentations or the things that seem rudimentary, there's so much opportunity within that as well.

14:47I mean, two things by that. One, specifically, can you be doing something that is going to be more helpful with that very simple task to other people? Some things that I did that helped me tremendously out of the gate were like, hey, this Excel document that helps organize the hotel rooms that we're booking is color-coded in this way. Would this be helpful to other people? Do you think this is cool? And all of a sudden, you're spreading knowledge and or you're starting a different kind of conversation. and then you can also be seen as a leader even if you're not intending to do so i was in a super competitive environment during that first year at abc sports and just doing something like what i just explained even though i wasn't intending to be like hey i want to rise to the top i thought i had no shot so i was just trying to lean into how can i be helpful and kind and leave a good impression on some of the people that are probably going to get to the next level when i may not But I inherently or unintentionally became seen as a leader amongst a group because I was doing things like that and just trying to help more broadly.

15:45Yeah, I think that's so valuable. And I think what you've said about just being helpful and kind and trying to get people in the organization to the next level or the organization itself to the next level in terms of productivity or efficiency or whatever it might be. And I think we so often see career movements as entirely selfish or needing to be a result of pushing other people down. Not necessarily, like we're not all thinking of just like stomping on other people to get up our career. but like that's somehow how it's presented especially within the corporate world and actually seeing that you know what are you here to do within a company you're here to add value okay that doesn't just look like hitting your own numbers that looks like helping other people hit theirs that's never there is never going to be an environment where you helping other people hit their numbers whether it's by knowledge sharing spreadsheet sharing whatever it might be is going to be seen as lesser than or less prepared for leadership.

16:46That is exactly what leadership is. And I think there's often this misconception that in order to get to the next role, you need to just do your time and kind of shuffle more in that direction and say you want that. Whereas actually, the closer you can get to actually doing that role with no one asking you to, like, how can you add the value to almost make your own role obsolete, like where you've climbed that yourself. I've always thought that that is the most valuable way of like, what better way to get a promotion than essentially to start showing more and more that you can do that by just doing it, like by doing some of the parts of that role where you can add that.

17:27Even better if you can prove to them that they don't need those two layers because you're naturally going to fall into the higher one. A thousand percent. Ask for more responsibility and nothing in return. But to your earlier point, if you're going to do these things, do it on someone else's dime. So when you're asking for more responsibility, yes, you are inherently taking on more work, but you're taking advantage of the fact that that's even stuff that you can do, that you can get your hands on there. and as long as you're able to have a good dialogue about expectation setting in regards to what you can manage and timelines and that kind of stuff then it's like this potpourri of things you could dig into that we're going to just broaden your skill set and give you more exposure across the company too right it's not about devaluing yourself in going for a promotion and not asking for a pay rise it's about making yourself a really really easy decision for that pay rise and promotion based on the fact that you stepped up to that before you needed to.

18:25Right. It's interesting too. And the places that you don't think are the sexy brands to work at, another place you can get trapped is what does the business card look like and what is the title on the business card? My current role, when I took the current role, it was called Time Warner Cable then. And it was vice president of production and creative services, which I've grown to love as a title. But going from director of marketing and sales or on-air management, whatever we were calling it at the time at ESPN, to Time Warner Cable, production creative services was not a sexy move, but the opportunity was a gigantic leap.

19:04And those places that have the less sexy name on the front of the store, they're going to want to retain talent in a stronger capacity than the brands to know that they've got somebody lined up out the door. And if you can be okay with all that too, there's a huge element in this as well of what do you want to do? Like, do you actually want to be a CEO? Because if you want to be a CEO, there is, to your point, a very clear roadmap. Some people I think also get stuck in between where like, I'm not 100 % sure. And then they'll get to a certain level and they'll make some assumptions like what we're discussing right now.

19:37And then that can get them very, very, very stuck. It's been fascinating, especially because I started in this role at 35, which gave me a large team, a lot of responsibilities, but also this really interesting vantage point of being in rooms with people 20 years older than me with 20 years more experience and seeing basically every single level of the company and starting to understand and having to understand why some people were where they were based off of age and background and skill sets and all of these things, because you need to evaluate talent, you need to be aware of how you want to build your team.

20:13But that also gave me this incredible lens into why some people stop and they become stagnant, why some people skyrocket. And some very simple variables that you also don't keep in mind outside of the skill sets and how you perceive taking on more opportunity and obligation is self-awareness through all of that. I've seen some of the most smartest people just plummet because they lack self-awareness. And I've seen some people that are arguably don't have all of the right skills in the right places, but their self-awareness put them in positions to have amazing conversations at the right time and be seen the right way.

20:52And then to your point of the value that you're bringing, companies are like, we have to bring this person further up the ranks or else we're going to lose them and we need to grow them. Yeah. No, I think another piece of feedback that's come back again and again and again, both in my own role and, you know, seeing the way other people found and end up leading companies and also through the people I've spoken to has been that you absolutely don't need to know everything, but you need to know what you don't know. And you need to know where your gaps are because that's exactly where, not that it's a bad thing, it's the fact that you can sit in a room being the person who's leading it and meant to be the decision maker.

21:32And you can say, I don't know what the right thing is here. Could you explain to me the difference between these two things or what you perceive to be the difference between these two things or what you think we should do to get in the right direction? And understanding that that is not weakness, that is leadership. That is a very clear part of leadership. and how valuable that is. I want to speak about this idea of corporate America. You're obviously kind of squarely within that and have been for a bit now. Could you tell me the biggest, probably like expectation versus reality of this idea of like working pretty high up in a Fortune 100 company?

22:12I think the expectation from the outside or from what a lot of the content that you see right now is this really awkward, there's no real humanity within an organization. And so much is out of your control. It's just a bunch of cliche jokes about communications that come through the tools you're given, like all of these variables that are just punchlines, basically. Where the reality is, it's just a bunch of people. And if you can actually take the time to at least digest who the other human being is as you're going through it, it's going to make you feel a bit more human as well. And I think over time, you will eventually find your people and you will eventually be okay.

23:00From the seat that I've been in over the past 10 years, again, it's been that self-awareness piece that has been a massive differentiator between those that are successful and those that are happy and those that are not. And that includes things like how you're spending your time in conversations, because you could be perpetuating some of the stuff that from a perception perspective makes you turned off. If you were spending a lot of time discussing why these reports you're doing on a weekly basis are the worst things in existence, then they're going to remain the worst things in existence. The more conversations you have around why Monday sucks, the more Monday is going to suck.

23:38once you realize that you have those things in your control which is not easy but once you realize you have those things in your control then you can be a bit more empowered and you're like i don't really want to carry the burden of me having control over how i feel here and even admitting the fact that i might be able to control it more broadly but you do the ability to kind of control how you interact with other people and the fact that when you give them a chance, you will actually develop these relationships that you will be pleasantly surprised by. And the fact that the things you will have at your disposal from a skillset perspective as well, if you look at it as mundane, if you look at that rapport as being the worst thing ever, if you look at Mondays like Mondays, then they will remain that way.

24:26I think the perception versus reality is how much you can actually control. And if you give yourself that opportunity, it is not easy. But if you give yourself that opportunity, you can change your career growth, you can change your happiness levels, you can change where you're going to be in five years. And most importantly, on a day in and day out basis, you're going to be able to control your attitude to just have a better time while you're there. No, I think that's incredibly important. I know as well that you've spoken a lot online about things like how to banish the Sunday scaries, which kind of feels like it fits within what you're saying at the moment.

25:02Can you talk about that a little bit? Yeah. The funny thing here is what I haven't said in this space yet, which is if you have your shit together, you really should have nothing to be scared of. Right? But I think a lot of people actually do have the Sunday scaries because they're like, I'm totally not ready for that meeting on Tuesday. Right. or that report kind of sucked or there's things like you bury things along the way. We've all done it, right? There's things that are just not perfect. There's a lot going on. But where are your gaps really, right? There's some things that I've just mentioned that are probably not that big of a deal.

25:39They might be giving you the Sunday scaries. But if you're willing to have a hard look at what do I actually need to get my shit together on, then you should be okay. And if you're doing your stuff And if you're communicating well, there's only so much you can control. And then you shouldn't, there's nothing to be scared of. Once I had the realization that I wasn't going to get punched in the nose in a meeting with like the president or anything along those lines, like, why am I so nervous? Why am I sitting here like, oh my God, like, how am I going to concoct the next sentence and all? They're not going to, if they punch you in the nose, you're probably going to walk out with a fat check.

26:18There's things that are just not going to happen. Yeah. So why do we feel so paralyzed? And if you can have a straight conversation with yourself about what you have done, is your shit in order, then you deserve to take a deep breath. Because again, these are just other human beings that you're walking into this environment with. Don't be so freaked out about things that are just in your head. but I don't know if, I mean, you can certainly do things like check your calendar. No, people don't want to hear check your calendar on a Sunday, but check your calendar. What's in your inbox that's freaking you out?

26:55When we started snack hour in our house, that was a huge breakthrough moment. It was very awkward to be sitting on the couch with Kelly one night and be like, Like I am anxious as the day is long. I have to get up right now and go in the other room and work. We have this assumption that especially if you've got a relationship and you want to have this work-life balance that you can sit down at the end of the night and you're going to consume some sort of content or something and there's like that time. When I realized that being present with her was more important than sitting on a couch and watching whatever and that my anxiety would be quelled by going to the other room and working and then we realized that might feel kind of awkward for us to be like cool see in an hour I'll see when I come into the kitchen for a snack but then all of a sudden I had control for the Sunday scaries whatever that level is you might not need to put I hope nobody needs to put in the hours that I do, especially right now.

28:03But if you're willing to understand the hours that are needed to at least give yourself the calm of understanding what's on your plate, because if there is an unreasonable amount of stuff, and a lot of people have to deal with an unreasonable amount of stuff on their plate, but if you are able to fully digest what that is, then you can potentially problem solve for that as well. But long answer short, if you really have your shit together. And if you just take a minute to be like, where do I actually have gaps? And then what am I going to do about them? Then you should be fine. Like the lingering fear is just, it's so not healthy for us overall.

28:41Be honest and give yourself that mental space back. What are you actually concerned about? And then can you make a list and then parse that list into two? Okay, here's some things that are just me being, you know, way too antsy about whatever, but here's some things that, yes, I have a gap in these places. So that's a, that's, that's a brilliant move to have your staff. And how big is your staff? About 40 people at Tala, about 20 elsewhere.

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30:33Well, you're managing a team of 200, is it? So right now, at the peak, it was 270. Wow. In August of last year, I transitioned 160 or 180 to another department as part of a bigger maniacal plan in my head of like… To take over the world. Well, so by the time this lands, my team will know. So it's not inappropriate for me to say now, which is this is very odd for me overall. At some point, I don't know, probably early last year, I started to get the question, if not before then, when are you going to leave your job? The jokes that you would get, and this is all very new and very strange to me as somebody that's now 46, and where the hell did all of this come from?

31:25Why do people stop me on the subway? Why am I getting asked to come do amazing podcasts? This doesn't make sense. so you have to digest that obviously and as time goes on and you get asked around 200 000 followers like oh is this a thing now and you're like no i've been in this corporate gig for quite a while and i'm married with a daughter that goes to a school that has tuition and i'm more like i don't see something sustainable here and then it started to become more real that there's something else going on that could be sustainable. And I've always loved the idea of either executive coaching.

32:05I wanted to be a writer when I was a kid. I love making stuff like you don't make 1500 TikToks, however many I've made now, if you don't actually love doing it, like I love doing it. So at some point it kind of got to a, if I'm going to leave corporate America and if I'm going to leave this specific job. And I would argue the job that I had going into August of last year was the greatest job in the history of advertising. I will stand by that. I will die on that hill. That is a bold ass statement, but I will die on that hill and I can make that argument. I started to unwind it because I knew that it was probably going to get to a point like where I'm at right now, like literally right in this minute.

32:51And if I didn't start to take pieces apart before it was too late, then I would have massive regrets because I built that from the ground up. It actually like makes me a little emotional to say. And so I needed to be really intentional, even if it was, it was probably already too late. I don't know, maybe it was timed well. So that tied to my, you know, potential transition into something else in my head. Literally last year, I'm like, all right, here are the stepping stones to be in a position where I can fully transition myself out of here. I have to figure out a home for the thing that I built originally.

33:28That has to be in a very safe and secure place. Based on what I know I can do for the company, let me start to build that out. But then I'm sure as you know, you can create a system in a direction. We don't actually have to do all the keystrokes yourself. So over the past, I mean, it hasn't even been that long now, August, September, October, like five or six months, building that team the right way and starting to empower them the right way but again with a company as large as ours like there's a lot of cooks in that kitchen and this year especially after the book deal went through and i'm starting to write that in addition to keeping the day-to-day content going um it just got to a point where i'm like i can't i can't keep doing all these things like i'm really really really going to burn out like there have been jokes about burning out for a long time now.

34:19And I've been doing this for years before I made a single TikTok. And then it came time to just start to really unwind that. It's really, really insightful. And I feel like your story is such an interesting one in the way it's evolved over time and the way your kind of role has evolved to a point that you're almost building yourself out of what you've already, you know, what you've been doing. Before we move on to talking really about this decision to leave your job, I'd like to first ask what the biggest piece of advice you have from, you know, leading 300 people in a kind of Fortune 100 company.

35:05What's the best advice you have for leading a team as a whole? Be cognizant of the fact that when they go home at the end of every day, they're probably going to have a meal, they might have a meal with somebody else. At some point, whether or not they're having a meal by themselves or with spouse, partner, friend, whomever, the question of how your day is going to come, how is your day is going to come up. The more often whatever you are doing as a people leader, you can get the people on your team to say today was a good day. Then you are doing a really good job because they're not going to say that if they're super Overboard.

35:41And they're not going to say that if they're way too stressed out. Define the balance so that at the end of as many days as humanly possible, the people on your team can say today was a good day. I think that that is one of the most critical things you can keep in mind because that impacts how you're looking at process. It impacts how you're looking at workload. Are your goals right? How are you measuring things? What is your communication like? It's an easy place for me to go to and think really specifically. Like I will picture an employee where I know that they, what market they're in, what I know about them and paint the picture literally of them sitting down with whomever and having that meal and being able to say that in whatever their tone is that I know from them.

36:23And there's an element of humanity and humility that goes into that because then you're also one of them. And that's kind of the side piece of it is like just being one of the team and just getting them to be able to say today was a good day as often as humanly possible because all of the business stuff and like I've run the$30 million P &L, I've run that large team, like I've done all of the things. But that focus of let them have as many good days as humanly possible, I think can help solve so many business problems. No, I completely agree. I'd like to ask very specifically how you believe you get as many people as possible to go home and say, I've had a good day as many days as possible, whilst also making sure that you're getting often very hard work and often, you know, challenging things and the right output out of people at the same time.

37:21Clear on purpose, right? You got to be super clear on purpose. Like why would they want to have those difficult days? Do they feel like there's something that even if there's not purpose relative to solving world issues, purpose to how it plugs into the rest of the company, purpose to the people that it serves as well, purpose to their coworkers. If you can paint that really clear picture, that can help when it comes to the challenges and make it easier to be to push and push in ways that are still going to lead to today was a good day. So purpose first and foremost. Then it comes to the tools.

37:59What do they have at their disposal? Is it the right workflow? Do they have the right gear? Do they feel like they are being handcuffed by the technology in their hands or is it empowering? Can you explain why you're making those decisions, especially with a large team? You're going to do a software deal. Not everyone's going to like it. How do you have that kind of conversation? so purpose tools then communication to make sure that the purpose and the tools are being explained the right way to make sure that they feel like there's a dialogue happening to make sure that they are fully empowered relative to the impact that they're having right because part of that communication can be the data sharing of this is what your work did this is how it helped that business, our company, this goal, et cetera.

38:51So if you've got the purpose, the tools, the communication, through the communication, some of the data and the impact that they're having. And then the last piece that I'll say that kind of has to go through all of it is the culture and the values. What is the expectation from a behavior perspective? Because you should have a thousand percent, you should have expectations from a behavior perspective and you should be adamant about those. The places you should get the most passion about is making sure that people behave and treat each other the right way. And you can define what the right way is because it is a work environment, not to be stringent and not to have any kind of lack of humanity, but to make sure that humanity is added in.

39:39One of the favorite things that I've done over the last 10 years was be part of a culture and values committee that rewrote the company beliefs. And I'm very proud of that for many reasons. But one specific sentence that I think is lost in so many conversations that are happening all across corporate America right now, and that's understanding the effort behind the ask. If you walk over to somebody else's desk, you're like, yo, I need this. I need this like now. Do you have any idea what that is or what keystrokes it takes that person to get that done? especially if you think in a large matrix organization the more you understand of how other people are doing their job even at a high level then you're going to treat them a bit kinder so not to go off of a specific tangent on that one too but like the purpose the tools the communication communication includes the impact that they're having and then the culture and making sure that you have very specific things that are going to ensure that as all of that's happening, it's happening the right way.

40:46I think that's a pretty magic recipe for people to then be like, cool, I'm, I'm got a pretty decent streak of good days. And even when they're stressed, the recipe also helps give clarity as to why the stress might be worth it. I want to come on to speak about your TikTok. What was the first video you posted? it august 2019 it was my wife daughter and i going to a art exhibition in williamsburg called beyond the streets and i was just literally seeing what it could do from an editing perspective it had a jay-z song in it picasso baby to be specific and i took a few clips it's funny if you see it now you'd be like i that's got every element of what we still see with him it's like a shot of me riding a bike which shows up in a bunch of stuff us out doing something together which shows up in a bunch of stuff the two of them just being them and there's no voiceover but it's just you kind of get the sense that there's a family that took a bike ride to go see a museum exhibition and that's it and what do you think makes a good video a good video is something that gives value that entertains, that elicits some sort of emotional response, a great video is something that you need to share with somebody.

42:08I mean, you said something really important there, which is be okay to do things that don't see the light of day. That took me too long to realize that I could just play, so to speak. Also interesting just being in my 40s and married too, when my wife would text me and be like, you know, we share a cloud account. So she's inundated with every single clip that I take every single day. And sometimes she'd be like, what was that thing? I'm like, don't worry, I'm not going to post that or whatever the case may be. I'll go through phases where I get a lot of anxiety around how things might do. And sometimes where I'm like, this is amazing.

42:45And I just want to spend time there and respond to comments and just be in it as much as I can. Right now I'm in a phase where I just don't want to see anything. My wife will send me screen grabs of things. She's like, this is performing really well. I'm like, I don't want to hear, I don't want to hear, I don't want to hear. But it's, you know, it's just, it's so much fun. Like I just love making stuff. That's so funny because I think that with TikTok, the strategy almost can be to pay attention to nothing. Like I'm very analytical and very strategic. And originally the way I was on social media and the way I would replicate best performing content and all of these different things was so strategic.

43:22And at the same time, I really think with TikTok, the accounts that do best i'm not saying they're not looking at the analytics and they are absolutely looking at the types of content that performs best in all of this but so many people's strategy just seems to be just getting stuff out there like not overthinking it just like because you never know what will blow up on something like tiktok and just like like i never check my tiktok notifications like i'll check them on other apps i do not check them on tiktok because the whole algorithm the fact that it majority pushes you out to discovery is just I'm like that's not gonna I'm not spending my day on that I'll overthink that but actually it's such a kind of good concept when it comes to TikTok I want to pick up quickly on your morning schedule which you do TikToks about and it's very intense could you take me through your morning schedule and why it's structured like that it's I'll answer the question why it's structured first like this specifically because I'm not smart enough to do all this stuff without it being this structured.

44:25It's literally, these are the, the, in a, in a, I don't know if this is common in the UK. We have a thing. It's 12 pin bowling, 10 pin bowling, whatever we have. And you can, in some places you can put up bumpers so that the ball doesn't go into the gutter. So the kids can play and they'll just have fun and hit the pins. My structure are my bumpers in a bowling alley to make sure that I don't roll a gutter ball um so it's 402 alarm which is really just an old bad joke used to be 420 because it was like haha yeah weed 420 um but i'm like i want to keep the two in there and keep it abstract so 402 alarm i always have a basket of stuff that's ready to go basket of stuff is this weird led mask that i've been wearing because it was given to me by whoever gave that to me therabody i think my workout clothes and then whatever other like tchotchkes that I might need because then I can get out of bed shut off my alarm which I take a clip of and that's my first Instagram post of the day so like literally within the first 30 seconds I'm like doing something and making content which is feels weird to say out loud but it's true and been documented for quite a while now and I'll grab the basket so that I can sneak out of the bedroom without waking up my wife Like I don't get dressed in the room.

45:43And then I wander downstairs almost like a weird burglar, you know, in my underwear with this basket of things in the dark. And I don't drink coffee, but I drink pre-workout. Okay. I'll have two scoops of that. Some people think that I have an ungodly amount of caffeine, which might be right. Wow, that is a lot. 600 milligrams. Like I know all the data and stuff behind everything that I've – because this is old and a lot of it was in place well before TikTok. pre-workout I'll make sure my wife's coffee is ready to go and then straight to the laptop emails calendar for the day all the stuff that we discussed earlier relative to being the right type of boss to make sure nobody has to wait on me for review and approval stuff nobody has to wait on me to like make sure that I'm not going to be unprepared for that meeting I am a probably overkill when it comes to agendas for meetings.

46:38Always to my boss one-on-one the morning of an advance, always to my team the morning of one-on-one. Just so that it's almost like I'll take on some of that admin work that I'm doing at that hour because I know that it helps more broadly at work. And then once the work stuff is done, that takes me usually till about 5.30ish, 5 or 5.30, depending on the day. Some days my wife has to work early, so all of this shifts a little bit then i'll make a piece of content if hopefully i have the time i usually do that's when i'll finish the edit and do the voiceover and then once that's wrapped up uh it's time to go have fun which for me is get out of the house and go for usually for a run i'm in this weird running streak right now where like i can't stop almost to a certain extent but i was never i was never a runner until like two years ago when my wife said literally surprise you're running the New York City Marathon this year and I was like shit I've never run more than 13 miles before but I guess I'm doing this and now I'm like stuck in this weird cycle where I can't like okay cool I got 45 minutes I'm gonna go run five miles but it's actually kind of amazing to come to the Brooklyn Bridge Piers and see the city first thing in the morning also especially since of when I think this is gonna air I'm fine um I do I do like a good bit of cannabis before running getting out the door to go for a run and that's always fun as well it's like wow this is an adventure now the sun hasn't come up yet i'm just a little baked you know listen to some music decompress after the work session and making a piece of content you get it out of your system by the time you're basically home and then especially when you get home and you throw yourself immediately into a cold tub you do the plunge for three minutes which is hilarious i never am able to capture this the right way, but I'll sit, you know, so now we're at like 6am.

48:29We've done all those things in the run, lay in the cold tub, and I'm right below the F train, like it comes out of the ground in my neighborhood. And so it's still dark out some of those days, and I'm laying in this cold tub of water at six o 'clock in the morning. And there's the subway going basically over my head, which I can never capture from that angle, which just makes the whole thing feel almost like disney world-esque in its own way um and then shower get ready pack my bag out the door two days a week i drop off my kid at school and the other days i just get into the office and usually have my first meeting at 9 a.m or so um but it's you know and then there's a whole bunch of little things within that like i'm very odd in that i use two scales totally unnecessary.

49:20I wear two fitness watches, totally unnecessary. I'll take the time to even change the bands in both of them, both night and day. Like there are micro things within this that I haven't even gotten into because I'm sure people will be like, first of all, and especially because I, hopefully you'll, you see in this that I'm a relatively calm, relaxed person, but you try to say all these things in a 90 second TikTok and it sounds like you are on meth. So, um, you know, there's layers to it but that's kind of the general that's kind of the general framework from 4am to 9am and do you think you'll keep that up once you've quit your job to a certain extent i love the morning to make content a because as i'm sure you know like once you can't pick up a voiceover later on in the day so having more time to do more stuff to have a broader batch like there is at least an idea or two every single day for a piece of content that falls by the wayside because I just don't have time.

50:20I have this huge 240-page document of like 200 ,000 words of just stuff that I've accumulated over the years. My routine will be something in that ballpark because I just love getting work and organizational things and a workout, anything obligation wise for others. I love getting out of the way before anybody else is up because once the world is happening, then I feel more calm and at peace and I can be more present. So I think it'll be pretty darn close. I will need a couple of days. It's funny. My last day will be June 21st, which is my wife's birthday, which is fun for so many reasons. We're going to fly to Oregon and spend a couple of days with their family.

51:07And then VidCon is right after that. And it feels really weird to say featured creator this year, which is... Amazing. Thank you. It's, again, all of this at 46 years old. There's like so much about this where, especially if you meet a stranger or like you sit next to a couple at a dinner, you start to have a small talk and things come up and you're like, how do I even explain any of this? But I haven't figured out, and this is part of why it's exciting and also scary, I don't really know what's going to happen. I just know that I need the time back because I'm spending 80 hours a week plus still on this corporate job.

51:50There's a huge part of that that they don't specifically need me for. Like they're going to be more than fine. but i know that those 80 hours if i'm doing the stuff that i'm doing now if i have the opportunity to get invited by you to sit here to have this conversation because i've just like a total idiot been doing this off the side of my desk for so long i gotta see what's i gotta see what i can do with the rest of those hours or i will regret it for the rest of my life but most importantly I'll be able to pick up my kid more from school. So for that reason alone, I will do all those things once I'm like in my, so I can drop her off at school as much as possible.

52:31I love that. And usually I end by asking people what the best piece of advice they've ever been given is, but I want to touch on this piece of advice that you put on Instagram. I think it was, I saw the other day, you posted something about having, responding to someone essentially saying, yes, life does get so much better after you turn 30. And you wrote a breakdown of this and why you think it is and why you think it's important to kind of aim for that and celebrate that. And I'd love for you to talk a little bit about that because it really, I thought it was so powerful. Thank you. It's really fun to be able to do this now, like to be like and have people actually lean in for it.

53:14So when I was about your age, which is really funny to say in these conversations, I had the worst goal in mind for 30. I was going to make a specific amount of money. And I was sitting in a shared office at ESPN at the time. And I'm like, I'm going to have my own office. And it's going to be in this part of the building. And I thought that those goals would be a byproduct of other things. And therefore, it felt like a smart, very specific thing to point to. In hindsight, it was terrible for a multitude of reasons. number one it was just far too vain like i should not have cared about those things i understand why i did and i feel like there was almost a societal pressure of start to hit benchmarks or exceed benchmarks along the way right the things that stress a lot of people out in their 20s when am i going to get married when am i going to do these things when am i going to make six figures when am I going to get this?

54:10And it just distracted me enough where it was causing me to think about the path in a different way versus not caring about the path and caring about opportunity more. And once I got past that age marker and didn't hit those goals, it freed me up tremendously because I hated myself for not hitting the goal. And I was like, okay, now what? Let me just get back to work. And then the next few years were like a skyrocket from ideas, my opportunity to think bigger thoughts and just shop them around the company. It's amazing how as soon as I dropped that. So number one was don't get too focused on goals like that, or at least for me, getting focused on that specific goal was a terrible idea.

54:58Number two is that some of the dopest shit, and this is how the way I stated it, is yet to be put in front of you. In fact, it may not even been created yet. So many people think like, oh, this is the best set of friends that I'll ever have or these things. Yes, you'll have these momentous, whatever it might be, but you can always take those with you. But the idea that the greatest piece of art or your favorite movie or meal or restaurant or your favorite musician could be 10 years down the road. And this is what I I thought was hilarious. Noah Kahn, amazing musician. His music has had a massive impact on my life over the past year and a half at this point.

55:41First of all, I didn't get introduced to him until I was 43 or 44 from a friend that I met through the internet when I was 42 or so. And so the fact that there was that chain of events in the first place is like, you can never predict this stuff. And that dude was seven years old when I was your age. When I was 27 years old, Noah Kahn was seven years old. If I was back then, imagine being like, hey, in like 20 years, that dude is going to make an album that's going to blow your mind, right? Like these are fun things to think about in that context so that you don't get too freaked out about getting past 30 years old.

56:18There's that kind of weird magic where you're like, there's kids running around right now. They're going to do things that are going to be some of your favorite things on this planet. Or there's things that already exist or a thousand years old that You haven't even come across yet. So that was number two. The number three one, I started to ask myself the question, why do I pause so often at this one question that I get asked so much now? What would you say to your younger self? And every time it comes up, I'm like, hmm. And it's not just because it's in my general temperament to like take a breath on things.

56:51Why is this such a perplexing question? And then one day it hit me. I'm the same goddamn person. And I should be allowed to be. I pause because I'm thinking about the 17-year-old self. And it's like when you're in your own skin in that moment, yes, I can still answer the question and I don't have to be that profound about it all the time. But don't forget that you don't lose yourself. You get to keep those pieces with you. Growing up doesn't mean you're constantly shedding skin in a way that is removing parts of your soul that you're gathering and collecting and that you need. I need my 13-year-old self with me all the time.

57:29If that dude's not with me, then my love of sneakers is not going to be the same. And I want that. I don't ever want to lose that. I need my 20-year-old self with me all the time because that's the dude that helped my dad get through stage four cancer and learned life and death like he probably didn't need to see at 20 years old. But it happened. I could say that about so many different phases of my life. You keep that with you. You're still going to find magic that you didn't even know existed yet or hasn't even been created yet and you get smarter and more broad about goals that just allows you to be like cool big thoughts let's go have fun in life and that's what makes the rest of the journey kind of hilarious no i love that thank you so much for sharing that um i think that i mean we spoke quickly about this before the podcast started but i do think we have this like huge misplaced anxiety around turning 30 and around the fact that I mean so much of it will be based on the fact that the majority of positions in social media or people we see in social media are going to be weighted towards younger like of course they are social media was only invented however many years ago and so this like I posted a quote on Instagram the other day was about that was about like stop imagining your life at 30 like stop imagining your life at 30 start imagining your life who you are at 40 who you are at 50 who you are at 60 what life do you want to build for that person rather than only building this life for yourself at 30 because we all have this like misplaced conception that it just ends like it ends and amazing things happen when you play in longer term and you play in the understanding that okay well if all of my goals that I'm writing down now I could achieve by 30 then you are creating a life that stops then and I think that it's incredibly important not just be able to to be able to see a mix of representation in terms of what that can look like but in terms of actually being intentional about setting goals that do not stop there, that you won't be able to reach for 20 or 30 years and celebrating that rather than celebrating everything needing to be the quickest goal or achievement than it could possibly be.

59:50Totally, yeah. If you're not present and you don't have the mindset of what is possible and you keep that open, then you're missing out on a ton. I always think that I would be very overwhelmed by meeting if you brought the 27 year old right now and introduced a be like holy shit dude you went nuts with tattoos at some point when did that start because at 27 I did not have all of this I would have a thousand questions and I would probably be very overwhelmed by just even like trying to process what was going on here but it would all make sense at the same time too. But it does feel good to think, all right, let's gear up for, literally I remember thinking this when I turned 40, let's gear up for 50, but only from just like the simplicity of making sure I'm being smart about things so that I don't feel like I'm gonna collapse at 50 with my body and then how I was kind of taking care of myself more broadly and also never allowing for, as much as dreams might've been stuffed in my back pocket at some point, I obviously didn't stop, right?

1:00:56I think that that's a huge piece too, that regardless of where your goals may lead you to or if you're thinking, to your point, there is something far beyond 30. So don't quit on those, the biggest, craziest ideas that you have, because the longer you stick with them and the more years you get, the longer you can stick with them, like that's the beauty of that. then all of a sudden boom you could be 46 and you're like good god what is happening right now well guess what you had some wild ideas when you were a kid you had some bigger goals that got a little bit better when you were in your 20s your 30s gave you a bit more you know resolute to your day-to-day and you didn't quit along the way and you were very open to the fact that you could still be the same dumbass in your mind, but also be driven in a way that had a very specific, broader, this is the feeling that I want goal attached to it.

1:01:50And then magic can absolutely happen and come out of like the clear blue sky. I think that's the perfect place to end. Thank you so much. Thank you so much for having me. What a pleasure.

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