How I Went From Intern To CEO In 6 Months (My First Startup Gig)

And just to give you a sense of this, right? I'm 24 years old. I'm the youngest person in the company. I'm the newest hire in the company. And 6 months later, I got named CEO.

Prodigy.

That's pretty good. Pretty good, right? And the way to do that is you actually— Welcome to a new segment that we're calling— it's like a Q&A, but we're not calling it a Q&A. We're calling it Questionable Advice.

Does that mean that someone shouldn't follow the advice or that we're just answering questions and giving advice?

It, it means whatever people need it to mean. It's people asking questions, us giving advice. The advice is a little bit questionable as well, right? Because we're not telling you what necessarily you should do. We're saying what we, what we've done that works for us. It may or may not work for you. It may, it may not be the best way. It's just the only way we know. And so today the question we want to answer is actually different than usual. Normally we're always talking about starting companies, starting businesses, being a CEO, being an owner, being an investor. But today it's about what happens if you're not there yet? What happens if you're inside of a big company? So how do you stand out inside of a big co— how do you become a superstar employee? How do you become an employee that is just god tier and that opens up a whole bunch of doors? For you inside of a company.

How many employees have you had like that?

Every company, there's always one or two. There's always one or two that are just like so clear. And what I did was I basically plucked what are the things that they do? Like, what, what are the things I remember that they did that stood out to me? As well as a couple things I did after we got acquired and we went to Twitch. What are some things that I tried that actually I felt worked? Um, because, you know, I had to spend 2 years inside of a bigger company for the first time in my life. And I experimented. I tried a whole bunch of things. I'm not gonna talk about the ones that failed 'cause those were embarrassing or not useful. Uh, but I will share the ones that, that worked.

Dude, what's crazy is here, let me add two things, backstories to our, our perspective on this. One, you had someone who worked at, uh, Monkey Inferno and all the other companies that Monkey Inferno started. Well, you actually had a few interesting people. The first interesting person was Steve Bartlett. Who's famous for his agency and his, uh, podcast Diary of a CEO. I think the second person who's even more interesting is Farhan, a guy who started a company that's worth tens of billions of dollars. I was shocked that that guy would be, would, would consider you a coworker. That was a, that was an amazing get. The second point I wanna add to this person, and you probably, you actually had a few other people that were, uh, you know, Jason Hitchcock, you had a few other people that are wildly successful. The second thing to add to this, one of the best compliments I've received from you in the last probably 60 days is you texted me and you said, how on earth did you get Steph, Trung, and I forget who else you named. How on earth did you brainwash them into working for you for as long as they did? And that, so we've had, we've each had a handful of superstars who I don't ever use the word work for me because oftentimes it doesn't, I hate that. It's not that it's, we work together on something and I'm only going to be able to have them for a little, a short amount of time.

That's principle number one. You work with, you don't work for. And it's actually a pretty big mentality shift, which is working with somebody is a partnership. It's an agreement. It's a mutually beneficial thing versus I work for you is a, you know, there's a dominant person and there's a person who just basically takes orders and does whatever, you know, whatever they have to do, you know, based on the task list. And you never wanna be the work for. The work for is, you know, a servant essentially, whereas working with is a partnership.

But it's okay to have to be that for a little while actually, for someone who's interesting. Like if, if like Sean Perry doesn't have a specific need to be done and some kid is like, dude, I will, I'm competent. I will do exactly what you say for a little while. It's okay to do that for a little while, but I agree in general, you don't want to be that person. But, but yeah, working with is, is how I consider it to be done correctly.

I hired a chief of staff just now. This kid basically had a job at, I think like JP Morgan. And he was like, hey, he just emailed me, emailed me, emailed me saying he wants to do stuff. He's like, I can help you with this. I can help you with this. Is there a reason you're not doing this? And then I'd be like, no, not really. I should do it. And he's like, how about I come do it for you? I was like, ah, I don't know about you. Yeah, whatever. And he's like, here's an example here. I'm doing it, blah, blah, blah. And finally he did it. And I was like, cool. You're going to quit your job? He's like, I guess I can go quit right now. Like, If you say I'm in, I'll go quit. And I said, okay, bet. And then he went and talked to his boss and he quit his job banking. And now he's my chief of staff. And even for him on day one, I told him this. I said, we work with each other and not, you don't work for me because I actually want somebody who's gonna treat themselves that way because they're gonna get, they're actually gonna get way more done. They're going to be more productive. They're gonna be a higher caliber person if they think that way. It's a mindset shift.

Did you actually say bet?

Dude, he's 22. I gotta speak the language.

All right everyone, a quick break to tell you about HubSpot and this one's easy. Because I'm gonna show you an example of how I'm doing this at my company. When I say I, I mean not my team. I mean, I'm the one who actually made this. So I've got this company called Hampton. You could check it out, joinhampton.com. It's a community for founders. And one of the ways that we've grown is we've created these surveys where we'll ask our members certain questions that a lot of people, a lot of times people are afraid to ask. So things like what their net worth is, how their assets are allocated, all these like interesting questions. And then we'll put it in a survey and I went and made a landing page. So you can check it out at joinhampton.com/landingpage. /wealth, you can actually see the landing page that I made. And the hard part with this is with Hampton, we are appealing to a sort of a, a higher end customer, sort of like, like a Louis Vuitton or a Ferrari. So I needed the landing page to look a very particular way. HubSpot has templates. That's what we used. We just changed the colors a little bit to match our brand. Very easy. They have this drag and drop version of their landing page builder and it's super simple. I'm not technical and I'm the one who actually made it. And once it's made, I then shared it on social media and we had thousands of people see it and thousands of people who gave us their information. And I can then see over the next handful of weeks, this is how much revenue came in from this wealth survey that I did. This is where the revenue came from. So it came from Twitter, it came from LinkedIn, whatever it came from, I can actually go and look at it and I can say, oh well, that worked, that didn't work, do more of that, do less of that. And if you're interested in making landing pages like this, I highly suggest it. Look, I'm actually doing it. But you could check it out, go to the link in the description of YouTube and get started. All right, now back to MFM. The first subcategory or the first category I think we should have, we both have things that involve communication and writing. Do you want to like name a few that you have under that category?

Yeah. Okay. So I'll do, I'll do one simple one. So write an internal newsletter. People know us as the newsletter guys because you created The Hustle, read by millions of people. I created Milk Road, which became the biggest crypto newsletter. The newsletter thing isn't just for external. So you can have 100,000 subscribers in a newsletter, but if you're inside of a company, what you really want is 20 subscribers, but they're the 20 most interesting people in the company. And so what I did when I got to Twitch was there was a team, like Bezos has something called the S-Team. I don't know if you know this at Amazon, it's like his like 15 to 20 top lieutenants. And Twitch being owned by Amazon had its version of this called T-Team. And so I got put on T-Team. And so, you know, T-Team is like, whatever, 15 of the top people in the company. And I go to the first meeting and, you know, it's a busy meeting. They're not, you know, they're like, oh, hey, welcome, Sean. We just acquired them. Sean, want to say hi? I'm like, I say hi for 2 seconds, but really I don't know any of these people. And so what I did was I created a newsletter and I created it for all of the T team. And then I would slowly, anytime I'd meet somebody interesting anywhere in the company, I'd be like, oh, by the way, I write this thing every week and it only goes out to a select number of people. It's fun. You'll like it. I'm going to add you. I'm going to add you to the list. And so they're like, okay, cool. I'll be added or whatever. And what I would do is I copied James Clear's newsletter format. James Clear does something called 1-2-3. Guess what? I wrote the 3-2-1 newsletter internally, which was basically like, you know, um, it was 3, uh, or no, sorry, he does 3-2-1. I did 1-2-3. So I did 1 photo from my camera roll. So here's a photo. I did 2 thoughts, which is just like 2, like kind of tweet length things that I'm thinking about inside the company and 3 links, which is just random shit that I've seen.

What type of photos?

Uh, it would be usually something like, um, You know, not work-related.

So for example, a culture-building thing, like I saw John brought in this funny mug.

Not, not work-related at all. It would just be something about my life that's like an interesting thing for my life. And I'm not a big Instagram guy, but I kind of get the idea, which is a photo can say a lot about you and what you're interested in and all. You can kind of brag a little bit, like, okay, like my kid learned how to ride a bike this weekend. Yeah, exactly. I'm such a good dad, you know, like here's what I'm doing. And so, you know, I like, for example, I did one photo that was this list that my, um, my niece had made. She's 7 and she, she wrote her like routine. She's like Ellie's day. And then it was, um, eat, play, sleep, eat, play, play, sleep. And I was like, somehow the 7-year-old's got it figured out. What are the rest of us doing? And right, like that's the life you gotta live. And so people loved it. They're like, oh yeah, that's so true.

Blah, blah, blah.

And so I would just one photo, two thoughts, three links. I would send that out every Sunday. And I wrote, I said, hey, the way I framed it, I go, you know, when I was a startup founder, I used to send this to my, our investors and board of advisors every Sunday. I'd write like an update on kind of where my head's at. Well, you know, old habits die hard. Even though I'm not a startup founder anymore, I'm working at Twitch. I still have this hour every Sunday. I'd like to— you guys are now my new board of advisors. You guys are my new mentors at this company. So I wanted to include you on this. If you're on this list, it's because I think you're one of the more interesting people in the company that I hope to learn from and get to know over time. And so that was how I started it. And I wrote that thing, dude, I can't tell you how much juice I got out of this, right? Because it took me about 45 minutes to write this every Sunday, but now I'm getting sort of like, you know, every single person's attention in a very, and they, they know about me. They learned about me. They have an opinion about me. Not everybody loved it. I'm sure. I'm sure some people were like, whatever. I don't care about this. but it didn't matter. It got like forwarded up. There was a guy who was like the VP at Amazon Prime would email me and be like, dude, I love these Sunday things, man. He's like, I wish we got to work together because he wasn't even in the company. It got forwarded to him and he was like, these are awesome. You want to like just meet this? You sound great. You sound awesome. And that's the whole goal. You want to build a brand internally. And one easy hack to do this is the internal newsletter.

And there's actually, uh, I think even more implications of this. So one of the greatest people I worked with was Steph Smith. She's been on the pod many times. She's already doing great things and is going to go on to do even bigger things. She, uh, there's this thing with history. I read a lot of history where oftentimes the person who writes the most popular history book or writes history books, they actually control the, they control what we think of history, even if it's fake. She did that, of course, in a good way where it was very tactical. She actually couldn't, she was the best Google Sheets maker and a really good Google Slides maker. And so she would dictate how the Google Sheet for the projects that she ran and then eventually other projects, how they looked. And that actually dictated what we tracked, which dictated what we do, the things that we do.

Yeah.

And she, but she would make these, I don't know, did I ever tell you the sheet that we had for trends? Did I ever show you that?

No.

I'll, I'll just show it to you sometime. But she made this beautiful sheet, it auto-filled and like, I was like, oh, thanks for doing this. This is amazing. You should do this for all these other things. But she basically controlled the information flow. And so if anyone had a question, if anyone wanted to know anything, they had to go to her. And she wasn't doing this for bad reasons, but she was basically a very powerful person because of that reason. And so you need to get really good at presenting your work and you need to be really, really loud about it, but you have to be great at presenting your work, making presentations, writing stuff, controlling the Google Sheets and making them look presentable and making them work well. That is incredibly important and not, not enough people think about that.

100%. 100%. The winners write history, right? And, and, uh, and also the other thing is you want to be a maker, not a taker. So most people in companies are just takers of plans. So somebody else writes the plan, somebody else makes the doc, somebody else creates the dashboard, and you just sit on the receiving end of it. What I would do, you know, when I was at these companies is I would always write my own versions of the plans. And this was partly for practice because I wanted to, if I wanna be the CEO, well then I should get reps doing the things that the CEO's doing. He's writing an annual plan. Cool. I'm gonna write one too. What would I say? And you write it and then you compare to what they wrote and you see things that they did better and you see some things that maybe they missed out on. And so being a plan writer, being a proposal writer, being an update writer is gonna be the thing that actually sharpens your skills so that you If you wanna be a leader, what most people think is, I'll wait till I'm promoted and then I'll start doing leader things. Well, that's not really how it works, right? You start doing leader things and then you get recognized and promoted. And so if you want to one day be the leader, you gotta be the plan maker, not the plan taker. And you, you wanna write your own version of all the things that, all the key, key stuff, the annual plan, the quarterly update, the, um, the launch guide, whatever, whatever it is for a given project.

The next thing I would say is, and this is actually challenging for a lot of people. I have a feeling it wasn't challenging for you 'cause you're a very confident person, but it's important to be a, to, to be loud. And when I say loud, I don't mean that you have to talk a lot, but I just mean you have to make sure everyone knows the cool shit that you are doing. And there's a fine line between being selfish and stealing other people's stuff and taking too much credit and then also being loud. But it's important to be loud to let everyone know these are all the amazing things that are happening. And you have to present that in a really wonderful way where it shows progress, and it shows even if you screwed stuff up, here's the swings we took. I think I always had this problem. I noticed it particularly amongst the women who worked for me. I would always have to encourage them. I'd be like, dude, you got to speak up. You got to be louder about this shit. This is really awesome. You are not inserting yourself into the conversations nearly enough that you should. This is really, really talented, amazing work. So I think being loud is incredibly important to sticking out within a company.

Yeah, exactly. You wanna work in public, so you wanna, you know, present the things that you're doing. And like you said, it's not all bragging. So for example, you know, people would report in a format that's sort of like, here's the, here's what went well, here's what didn't do well, or here's the screw-ups that we had this week. And some of the things we learned from that are what we're gonna do to fix it. So like, it doesn't have to just be everything I did was great and I'm the best and I did everything, you know, it was all me, me, me, me. It's not that. However, you're totally right that you're really only rewarded for what people know about. If you're, if what you're doing can't be measured or isn't seen, it might as well have not existed inside of a big company. And for a lot of people, that's very uncomfortable to do. They wish the world worked differently where it was just purely, purely merit-based and everything was equally visible. It's just not true. Like if a tree falls in the forest and there's no one there, right? Like, you know, you need to be able to, to highlight what you're up to and, uh, carve out 10% of your time to doing that.

Let me tell you one more thing that's a bit unrelated, but a very controversial, and it took me a hard, it took me a long time and I had to go through a lot of tough challenges to learn this. Titles matter. Did you, I imagine when you started your early companies and maybe you still do this now, you were like, dude, I don't care about titles. You can call yourself anything you want. It means nothing to me. This is a flat organization, but titles actually matter. For an employee and they matter because of the job that you have there, but also the job that you can get elsewhere.

So give me an example, cuz I would disagree with this. I don't think they matter that much. What's the, what's the example you're thinking of where it mattered?

Okay. So if you wanna be called the head of something, uh, that's actually really important for the employee. It's actually scary for the employer because you wanna set you, you, if you give someone the head of marketing, you can't hire someone above them, or if you do, there's gonna cause tension. However, for the employee, if they go and work at a new company, they're going to now say, look, I was already head of marketing at this company. I need to be CMO, or I need to have something of equal seniority. Additionally, within the business, if you, if it's, I'm the head of blank, I'm the head of marketing, everything that happens within that, I need to have my say, or I need to have my finger on the pulse with that. Titles, I actually think are a really important thing. They seem not important to an entrepreneur because you say these things like, Oh, it doesn't matter, we're all working together. But I actually think they're— I, I, they matter for the employee.

So I would say, in my opinion, the logos matter. So there's a funny thing that happens where it's like, you— I bet you're guilty of this too. Let's say you're, uh, you're building, um, Hampton Now. It's like a community or membership-based product. If you see, oh, this person ran community or memberships ads whatever, YPO, YPO, Soho House, whatever, known, known thing versus unknown brand. For some reason, we just sort of attribute all of the success of that company to like, this person must be a winner because that company is a winner, even if they had very little to do with the winning of that company. That's the secondary step.

At The Hustle, I had a guy who worked at Facebook and he wanted to join us and I was like, oh, you're in. And we hired him and he was, it was horrible, but I totally fell victim to that. I've done that all. I do that all the time.

This happens to me with live streaming. People are like, oh, you worked at Twitch? Oh, we, we need somebody. We, we're doing live streaming, so it'd be amazing to have you on board because of your experience at Twitch. They don't know my experience at Twitch. They don't know what the hell I was doing there. I learned way more about live streaming at my startup that they don't know about that was actually building live streaming that was working in that space. But if all I had was that unknown startup name, I would've gotten zero credit for being like, you know, live streaming expert guy. And so I think logos matter a lot. And just getting a winner logo. Unfortunately, that stamp, that stamp is, is cool.

Um, the thing is no different than having Harvard or an Ivy League, an Ivy— oh, if you're good enough to pass that bar, you're good enough.

And one is enough. One is enough. That's the key. I think one problem people get into is they go logo collecting. One is enough. If you, if you got Harvard, awesome. You don't need to also go get another MBA from some other place. Or if you have Facebook, you don't have to make the next one Google. You can make the next one a little higher variance because the Facebook will carry. The other thing I'd say is managers matter. So when we got acquired by Twitch, we were getting interviewed by people. And we got interviewed by several people when we were joining, and they were like, they were supposed to be diligencing the acquisition, but I was also diligencing them because I was like, dude, I know that managers matter. People don't quit jobs, they quit managers. And also, if you're stuck under a manager who doesn't have a lot of respect in the org, You're not even going to get to see a lot of the interesting shit that goes on. Or even if you do stuff, it's going to be buried under however much clout that manager has. And so they first tried to put me under somebody and I was like, no, no, no, no, I'm not working for that guy. And they're like, what, what's, what's the problem? I was like, nice guy. I'm not working for him. And they're like, I was like, is there anybody else? Cause, uh, you know, maybe these two people, I liked them. They see, cause they clearly like, you know, we're buds with the CEO and had more, more like They were doing all the interesting projects and this guy's over here working on trust and safety or maintenance of something or like, you know, plumbing under the, under the bridge. I'm like, I'm not trying to work on all those boring shit, those boring projects or with that guy. That guy has no respect in the, in the org. And I think managers matter. Pick somebody you're gonna learn a lot from, but also somebody who got, who has some surface area that you can get shit done and switch. If you, if you, if you don't like where you're at, try to actively switch. Um, all right. I have a different one.

Wait, hold on, dude. When I sold to the, when I sold The Hustle to HubSpot, it was, uh, the, the, the plan early on was I'm out of the picture and I'm just gonna do the pod. But they were like, all right, how about like VP of marketing and you report to this guy? And I was like, yeah, can we give me like a lower title? And you can make Brad, who's my VP, make him the VP and I'll report to him. It was just like way better. But I was like, yeah, let's, let's bring it down a notch. I'm not going to be a VP. All right.

Now there's something I call the 5% rule. I learned this from Furkan. So when we got acquired by Twitch, We're sitting there and, uh, we were supposed to work on X, right? We were, we were at that time a taker. We got acquired to do this. Let's do this. And, uh, Furkan wasn't very motivated. And I was like, dude, come on, let's try to do a good job here. Right? Like we don't have to totally sandbag this. I get it. It's not like the same as when it was our company and this might become the next big thing, but like you seem totally checked out. And he was like, no, no, no, I'm not, I'm not checked out with the company. He's like, But look at this. They pulled up the overall company dashboard. He goes, best case scenario, this thing that we're building, best case scenario, which of these metrics changes? And I'm looking at the key, the number one dashboard for the company, the key KPIs, overall ones. And I was like, well, none of these. Go to page 3. There's subdivision, subdivision, and then this one. And he is like, cool. So let's say, all right, let's say we change that one. How much do you think that changes the overall? Picture. Like, he's like, don't you think that we should at least, like, if we do a great job, what we should do should make at least a 5% impact in the company. And I was like, my ego gets involved. I'm like, yeah, of course, 5%. That sounds low actually. He's like, yeah. He's like, I just think we're capable of doing something that's going to at least move the needle 5%. He's like, I feel like if I did something and it didn't even, whatever we did, if we did a good job, if we succeeded, but it couldn't even move the needle 5%. He's like, I kind of feel like that was like a waste of time. And that's when I learned this 5% rule. And when we, we immediately switched to something that would do that, and it was such a good decision. I wouldn't have done this, but in the same way that Naval says you want to place an absurd hourly rate on your time so that you value your time and you put a price tag on your time, this actually is also inside of a company. You need to put a price tag on your projects. That you simply will not work on projects that can't move the needle for the company. Because if not, why am I here? What is the point? And if you carry yourself as somebody who can actually move the needle for the company, it's sort of self-fulfilling. You will become that person who actually can do that. Simply like you just raised your standard and now that's what you do.

Dude, you were lucky to have Furkan. Of course. Furkan, I don't know if he was either co-founder or was he one of the first hires at AppLovin? So AppLovin's a ad tech company, $15 billion market cap at one point, $30 billion market cap. Amazing guy.

So he joined the company before he was even Apple of an— he was not one of the co-founders. He was just like a random engineer that they hired. They had like 8 people. He was like person 9. Within a couple months, they were like, all right, this guy's the guy, right? He stood out like a superstar does. This guy's the guy. Let, uh, and they went to him. They were like, hey, I think we kind of built this team wrong. Now that we see you, we look at the other 8 people we hired before you that are above you, like we realized we did this backwards. Can you like fire all these people and rehire a new team of people like you? He's like, okay. So he did that. He ends up getting like a, you know, co-founder equity stake in the thing. You know, it becomes, it ends up going public and it's like a $20 billion company, you know, years later. Same thing happens. I hire him at Monkey Inferno as an Android engineer only. Right. So there's like, you know, Above him, there's the director of engineering. Above him is the CTO. Above him is me. Within a couple months, I was like, oh, this guy is a superstar. Like, uh, you know, Android engineer is simply the wrong title. And I told him, I said, look, uh, you're going to end up in a different role. Just give me a month to figure this out. And within a month, we had switched it up where he ended up becoming CTO and we basically rebuilt the whole team around him.

He sort of has like a master sensei, like a, like a, that type of wisdom to him where for some reason, whenever he says something, I believe him. And I, and I think he is actually right a lot.

More importantly, all the engineers you'll ever hire will believe him, right? This guy's a leader of engineers, which is like extremely valuable. Um, let me give you another, another principle. All right. Here's a simple one. Fix your Zoom setup. Just don't look like dog shit on every call. In fact, you should look incredible on every call. It doesn't cost that much to do it. Like you could do it with an iPhone app. There's an iPhone app called Camo. You can download it.

That's what I'm recording on right now, by the way.

And you could be DSLR quality from your iPhone if that's all you have. If you want to get one better, just get a light, right? Like a light off Amazon that's $50 and that app will set you in the top 1% of people at work in terms of how you look when you show up. Do that and have, also buy a podcasting mic. Your mic can be a, you know, a Yeti, a Blue Yeti microphone if you need it. Even better would be these like Shure microphones. You just look good and sound good because like no matter how good your ideas are, if it's wrapped up in a crap sandwich, it's gonna just come across poorly. And it's the, you know, is the digital equivalent of dressing good. And I think people really underestimate this. I think you made this like a rule at your company, right?

I mean, I try to make it a rule and I'll give it, I'll get really tactical. I'm using a shirt and I'm traveling right now and this is my travel kit. A Shure MV7 USB mic, that's $200, an iPhone with a $50 Camo subscription, and a $150 Elgato Key Light. That's, that's my setup when I travel. So if you think this looks good enough, that's what it is.

Yeah, it's going to be better than most people's like up the nose shot with the crappy audio and like, you know, sitting in a closet somewhere. So, so try, try on that.

Well, Furkan actually is a great example of this and a few other people really did a good job at this. I think that when you get into a group, whether it's work or any other type of group, oftentimes the most confident person is not usually the smartest person, but the most confident person wins. And I think confidence is displayed in a way of saying things like, this is the path we're going to go down. This is what we're going to do. I have a 60% chance certainty that this is actually going to work. My logic is this, this, and this, but this is the answer. At least this is the answer for us to try. And I think that at a company, when you work with a small company, like any company I've run, you work with the CEO or the owner. At a larger company, you know, it'll go up to the owner somehow or the CEO, but it still matters with managers and VPs and shit like that. But the confident person that says this is the way and they dictate the way and they explain their reasoning and they're confident about it and you start believing in them, you still have to be right more than you're wrong. But the most confident people, I think, typically succeed the most.

I agree. I'll give you two things. One, the thing you just described is like, uh, I think it's called the McKinsey Pyramid Principle. Are you aware of this?

No.

So basically, most people get communication wrong inside of a company because they bury the lead. So what they'll normally do is they'll say beginning, middle, end, like a story, and in the end is the conclusion. The end is the takeaway, what we should do. It's what's, what, what we've decided, whatever. But busy people inside companies, which are most of the leaders inside companies, they don't like that format. They want the opposite. They, what they want is to say, my recommendation is we should do this for these 3 reasons. Number 1, number 2, and number 3. And I believe those 3 reasons because we have evidence underneath this. This we do not have evidence for, but we will, but it's a reversible decision. And this third thing, blah, blah, blah. Right? You, stack the main conclusion first, and then you, you add like a pyramid underneath, you support it with your supporting arguments. And that's just a simple communication thing to flip. Another communication thing to flip that I learned was, um, there's, if you want to become a more clear communicator, use the what, why, so what framework. Emmett from Twitch taught me this. So basically it's what happened or what's going to happen. So, you know, if it's past looking, what happened? If it's, if it's forward-looking, what we're gonna do, why it happened, why we're, or why we're gonna do it. And the last one is, so what? So, you know, let's just give an example. Um, what happened is the, the metrics, let's say, uh, you know, revenue is down 10% this month.

Why?

Because last month we did this extra promotion, so we kind of knew it would artificially inflate last month's revenue. This month is actually normal if you look at the overall trend line. Um, nothing to worry about here. So what? Um, so we're going to continue doing this and actually we're going to consider doing those extra promotions every other month because they seem to provide a boost or whatever. All right. Like you just, you get the idea. What, why, so what? Just is a generically useful template or outline. Like you can write that on your paper before you figure out what are you going to say in this email or how are you going to write this document? Just write what, why, so what, and you should be able to bullet point under that. And then that's 80 to 90% of the material is already done at that point.

And I find what helps is if you put a confidence level in there, because a lot of times people think, well, if you're confident, you're saying that there's a 99 or 100% chance that whatever you say is going to happen is going to happen. You shouldn't do that. You should say, I'm actually, you should be really conservative and say at like, you know, 65%, 70%, like I'm fairly certain. Or sometimes you're like, I'm actually, I actually think there's a 30% chance that this works, but if it does work, the outside returns are quite huge. And if it doesn't work, it's reversible in these ways. And so I think you need like a little bit of a, uh, uh, I don't know how you would say it, like a, an easy landing if you fail.

Superstars do 3 things. Number 1, they think in probabilities, not certainties. That's what you just described. The second thing is that they manage expectations, which is the second thing you just said, which is you don't need to overpromise and underdeliver. In fact, you know, underpromise and overdeliver is a better mindset. And, uh, I remember one time going into a meeting. And this is something I learned from my dad. We were going to a big partnership pitch meeting and we thought, we thought they have this thing and with our technology, they're going to get this huge yield, this huge result. And the result is like 100 times better than their current thing. So I was like, oh, slam dunk, put that on the slide, baby. 100 times better. And we go into the meeting and I, my dad puts up the slide and I noticed that he's changed it and it only says 3 times better. And I'm like, dude, you messed up. Like, what happened? Why'd you do that? And he's like, he's like, did you see their faces about 3 times better? They were over the moon. That other stuff is now my dry powder. Like, I can beat— if I could beat the 3 times, even better. If I said 100 times and we came in at 80 times better, it would be seen as we did not deliver on what we promised. He's like, and so, you know, whatever, you know, forget the exact you know, numbers here, the, the principle holds true, which is only sell to the amount you need to sell that like gets them to agree to greenlight the thing or take action. But don't overpromise beyond that, even if you think it's capable, 'cause you'd always rather beat your numbers. Uh, beating your numbers is, is like, you know, how you exceed expectations.

And it makes you trust them more. And so here's an example. So, and I'm looking at the deck now. So Google, uh, whoever's listening, you guys can Google Uber. uh, seed deck. So in 2008, Uber was just getting started. They were raising only $200,000. And on slide 20, they have a deck or a slide that says potential outcomes. And they say, best case scenario becomes a market leader with over a billion dollars in annual revenue. Realistic scenario gets 5% of the top cities and we make around $20 or $30 million a year in profit. Worst case, we stay a 10-car, 100-client services business and just save some time for San Francisco-based executives. Versus when you see a slide deck from a pitch and it like, everything is like up to the right, you're like, dude, I don't trust you now because you are saying something outlandish like this and you're saying it with a huge high degree of certainty. And so, uh, yeah, anyway, I'm big on the confidence thing.

On the confidence thing is people think confidence comes from answers. No, confidence comes through asking intelligent questions. Um, any leader knows that you could tell a person's quality of thinking by the quality of their questions. And it always stands out if somebody asks you a question that's on point or breaks the frame of how you're thinking about things. That person always stands out in a meeting even though they didn't deliver some like, you know, very boastful, confident conclusion. And so, you know, an example of this would be you're in a meeting and it's kind of a messy, it looks like, you know, options A and B both suck instead of just saying, no, we need to do A, or no, we need to do B. Somebody who asks a different question that's like, you know, um, what would an easy solution look like here? Right? Hey, what's the simple thing we're missing? Right? I'm just gonna ask this out loud. Let's see if there's, see if there's an answer. 'Cause if there is, that might be quite valuable to us right now. Or, um, you know, we've been saying this thing, uh, just wanna say this out loud. Is that true? Do we have the data to support that? Like somebody who's questioning assumptions or breaking frames with their questions, Or that says, you know, we're trying to solve this problem. It feels like we're solving it from scratch. We're not the only ones who have this problem. How do other people solve this? Or how have we solved this in the past? What's worked for us? And anybody who's asking questions like that that are gonna cut to the answer faster, you stand out. That's a, that's a different way of showing confidence versus just saying, me, me, me, I, I, I have the answer.

Dude, I love, I, the one question that I love that all my employees hate is they'll give this like 12-month plan or something. I'm like, yeah. How do we do this in like 4 weeks?

Right.

That question is my favorite question.

Some of the best people, they frame that question nicely. They say this, this guy Florian I used to work with, he would always say this. He'd be like, I'm going to say something. You can beat me up if you think this is a terrible idea. Uh, you know, feel free to beat me up, but I just want to say it. And then he'll say the thing and it's such a disarming way of bringing up an idea that might be counter to where the flow is going or whatever. Cause you're always like, oh, Florian, you know, don't worry. We're not going to beat you up about this idea. But he would say that, right? Or, um, you know, uh, this other guy, Dan, he would, he would do this thing. He's now the CEO of Twitch and he would do this thing in meetings where he'd say, you know, he'd slow everybody down. He'd be like, you know, it's one thing we could say is A, B, and C. He'd like lay out an argument real quick. He's like, it's one thing to say this. It's another thing if we were going to say, you know, D, E, F. And he would just like frame it so slowly for everybody. 'Cause usually it's the person who can kind of like synthesize the arguments. Like what I'm hearing you're saying is A, B, and C. I just wanna make sure that it's, is it A, B, and C and not actually D, E, and F? And the person who would bring that clarity to the meeting was always like the essential person, right? They're the person who everybody thanks on the way out because they actually help you, you know, figure out the solution where it felt like everybody was just talking in circles.

What, uh, you want to do 1 or 2 or 3 more?

Uh, yeah. Okay. Here's an easy one. Let's say you're inside of a company today, but you want to go start a company someday. You need to start creating your own version of the Midas list, which is who are the 5 most interesting people inside this company, the people that you would want to recruit later on. What I did was I, I just, I said at the beginning, I said, while I'm here at this job, here's what I want out of this. By the time I leave these doors, I want to have the following. I said, and I wrote down a list. One of 'em was like, I wanna learn one or two things about leading a company that I don't know today. 'Cause these people have managed bigger teams and do it better than I, I'm sure that, that I do it. So I wanna at least have one or two key things that I can take away as a manager. Number two, I wanna have the respect of the CEO. I want him to be able to say, dude, if you leave here and you tell me you're gonna go start a company, I want him to, uh, wanna write the first check. I think that would just be a, a signal that I did well when I was here.

Would Emmett do that for you?

Yeah, he actually Slack'd me one time. He was like, hey, just out of the blue, he basically Slack'd me that exact same thing. He was like, I wish we'd be able to keep you forever. I don't think that's going to happen. If you ever do decide to do something, I'd love to back you in that. And I was like, oh man, what a compliment. Thank you. That's actually— I showed him, actually. I was like, that was on my list of things I said I wanted out of this experience. So that's a cool full circle moment. The third one is you want— I said, I want to walk out of here with 5 people, 5 more people on my talent Rolodex that I could reach out to if I ever needed to hire. And, um, and that's what I did. I was like, oh, this girl in data science, massively underrated. Like, she's the real one who delivers the work. She's kind of junior here, but man, she would be somebody I would poach right away. Or this guy over here on the sales team, God, that guy was smooth. Uh, if I ever have a thing for sales, I know who to contact. And actually right now with one of our new companies, I'm trying to fill a role. And those are the people I went to first to be like, hey, I have no idea if you're available, but I made this list before of who are the 5 people I would love to work with someday. And you were on it. And hey, that day is here. You know, what are you up to now? And let's, let's chat. And so that's, I think, another good thing. If you ever want to start a company, like, just pay attention to who are the hitters here, because your talent Rolodex is what kind of becomes a limiting factor as you try to build new companies, right? Like, I'm sure you have people that You know, you'd love to speed dial and bring on board to a new thing. And I think you did this with Hampton, right? Like I noticed there's some people there that were at The Hustle because that's the experience you had.

Yeah. I think that you actually asked, was it you who said something like a really good question to ask yourself is if you're starting your, like, let's say your thing's only going okay. If you were, if you were starting it again, which you would, you'd have to ask yourself, would I hire the same people and do it the same way? And for many cases you say, no, I would change this, this, and this. And then your advice to them was like, well, just fucking do that right now.

Don't do that. Yeah.

Yeah. But the, but the other answer is, okay, well, when you do it again, now you have your list. I think, uh, you know, in the mafia they use the phrase and then Succession kind of stole the phrase where they say like, oh, he's a serious person. And a serious person means you call them hitters, but in the mafia and the mob, like I read all these books on it. And they say, uh, oh, he's serious. He's serious. Yeah. That guy's serious. And so, or they'll say, he's not a serious person. You don't want to mess with that person. So you want to find serious people.

I have two other little ones, uh, real fast ones. One is find a paper cut problem. So I've noticed that a lot of people who do well in companies, they do this in the first two weeks when they join. They find something that's just been an annoyance that nobody's ever fixed or nobody's got to, um, because it's not that important. It's never the most important thing. And they just go clean that up voluntarily. I call this the paper cut problem. Like, what's the thing that's just been giving us paper cuts? It's kind of annoying, but you're not bleeding out, you're not dying, you don't have to go to the hospital. And if somebody fixed it, you'd be like, dude, thank you for doing that. Like, you know, it would actually stand out a lot. Um, I know several people that did this. They, they go to a company and they immediately identify like, oh, here's some annoyance that two people have referenced. I bet this annoys everybody. And actually, I think if I just spent one Saturday working on this, I could fix it. And they did that and it just like boosts their stock so much.

When I was in 7th grade, I had a job at a bakery and I would like clean the floors and wash dishes. And there was a corner or there was a shelf where we'd have to like put these dry dishes and the shelf was broken and we hired another janitor to work with me. And I remember like I had worked there for like 8 months and this fucking shelf was always broken. It was a pain in the ass. And like within the first week, this guy fixed that shelf and I immediately thought, that's the way to do things. You did it right.

Exactly.

You did it right.

And by the way, you get rewarded for doing the things you didn't have to do, right? Like if you just do your job, that's called your job. You do not get like extra recognition or reward or, or any kind of bonus points for doing your job. So you, by definition, you have to find something that is beyond your job or doing your job beyond what was asked. If you really want to get this to stand out. It's a very simple, obvious principle, but take that and make it actionable by like, go look for it, right? As soon as you start looking for it, you'll see it, right? It's a thing that the guy who's been there for 8 months has been ignoring. He's just accepted it. It's become a blind spot for them. But for a new person, if you're noticing, you'll see it right away and you just go fix that thing and you get so much better.

Yeah. This guy's head janitor now. I mean, it worked out. That could be you.

But honestly, if you're going to be a janitor, be the head janitor, like be the best janitor, be the best goddamn janitor anybody's ever seen. I got one practical one and then one fun one. The practical one is the other problem you want to find is the A+ problem. At any given time in any company, there is the A+ problem. It is the thing that the people that's keeping, you know, the exec team up at night, they're worried about it. What I did was I just found the A+ problem and I would only work on that. I would just work on that. I would do my main job kind of like, you know, 70% is good or 50% is good or sometimes 0% is good. I would just put it on pause because honestly it didn't even matter relative to the A+ problem. And, you know, I took a little more risk than most people because I didn't care if I ever got fired. Like it was, you know, thank you, please fire me, invest my shares. That would be a dream.

But dude, by the way, we had a friend who is at a company and he goes, there was layoffs this week at our company and sadly I was not impacted.

Exactly. Um, so find the A+ problem and work on it. I remember, um, I think I've told this story before. Um, I was at a company and basically a competitor was like attacking them and like what was, you know, stealing their top customer basically. And I figured, well, that's probably the A+ problem. It's probably the thing everybody's thinking about. And so I just did some analysis, did a, wrote up a, a 2-page doc and I sent it to the CEO. I was like, hey, you know, I have no idea who's working on this, but you know, I was curious, so I dug in and here's what I found. It immediately got like text introed into a group chat. It was like, hey, Sean's in on this now. And I think that that's really what you want, right? You want to be working on the interesting things because that's what the highest caliber people are doing. It's where the highest impact is. You might as well, you only have so many hours in the day, might as well work on the higher impact stuff with the most interesting high caliber people. That's how you get better.

What's your last fun one?

The last fun one is you got to create a brand for yourself. So like you have a little, the story, right? There's all these moments inside companies where it's like you do introductions or, uh, you're at some team offsite and, uh, you know, you have two choices. You're either gonna blend in or you're gonna stand out. The best way to stand out is to be yourself, but the, the way to be yourself is to just remove the filter.

And so what was your brand?

So I think there's been a couple.

Yeah.

Like when I was at Monkey Inferno, And just to give you a sense of this, right? I'm 24 years old. I'm the youngest person in the company. I'm the newest hire in the company. And 6 months later I got named CEO.

Prodigy.

That's pretty good. Pretty good, right? And the way to do that is you actually, you know, you make an impact, but you also gotta build some sort of brand for yourself. And so mine was, I was gonna be sort of like, um, the action, like basically just like take massive action on everything. So whatever the thing was, I would be like, all right, cool. I'm gonna take action on it. A, immediately. B, I'm gonna do the shit that nobody else wants to do. Like, I'm gonna go further. Oh, we gotta do this, or we don't know if people will like this.

Who? Cool.

Give me the prototype. I'm gonna go talk to some people. I would go to the mall and I would talk to people and I'd get feedback and I'd come back with like written feedback. It was just the shit that nobody else really wanted to do. And it just built this thing. Like, I'm going to consistently take action. I'm gonna have a higher bias for action than anybody else. And I would talk about that. I'd be like, yeah, I don't, like, I don't really know. Uh, you know, I remember this one guy did this intro and he said this thing, this guy stood up and he goes, I don't know anything about art or politics. I don't know anything. He goes, I don't know anything about art. I don't know anything about politics. Hell, I don't even know where the remote is in my house. The remote for the TV is in my house. But the one thing I know is how to structure deals. And today I'm going to tell you about how to structure deals. And I was like, wow, what an intro. What a fantastic intro. It always stood out to me and I thought, You know what, as much as your brand is going to be that you're good at X, Y, and Z, you could say how bad you are or how little you know about, you know, these other 3 things and just be honest about it and almost poke fun at yourself. So I would tell people like, look, I have the least experience of anybody in this room. That's obvious. I have never worked on any of this stuff before. I don't know how to code. I don't know how to design, but I'm going to make myself useful. The way I'm going to do that is it seems like what you guys need is help Actually getting your product into people's hands and getting feedback quickly and actually iterating from there. So I'm going to go crazy on that. All right. What you guys are going to get the next 6 weeks is me going crazy on that. Sound good? And they're like, they're like, great.

It's like Warren Buffett says, look for partners who have a high IQ, who are ethical and have a lot of energy. And I did the same thing where I was like, well, I actually don't know if I'm high IQ.

2 out of 3 ain't bad.

Yeah. Yeah. I don't know. I definitely am ethical. And I, and I have a shit ton of energy. So my wheels are spinning fast. If you guys just want to point me in the right direction, I'll go ahead and the car will run and it'll run quickly and I'll get you what you need. I had the exact same brain as you.

And when we got acquired, I just, it was like, hey, I'm a startup guy inside this big company. I'm a startup guy. I've only ever worked in startups. I don't know anything about a big company. Honestly, I'm going to probably make some mistakes that are things that are obvious that you should do at a big company. But the thing I hope to bring to the table is I'm just going to keep working the way I know how as an entrepreneur. I'm just going to just do that here. And, uh, you guys tell me what parts of that are working for you guys or what are not, right? That's part of the brand. But the other part is like, stand out a little bit. I remember sitting at an offsite and it's like, oh, um, how about everybody just share, you know, how things are going? And it was like, person one said this like boring thing about like, you know, they just immediately went into like work mode, right? Like, you know, they were like, you know, here's what I'm doing. Here's the problem I'm having. Here's what I'm doing. Here's the problem I'm having here. Uh, I have this employee who's doing this and everybody's just kind of bitching and moaning and telling a very bland story. And I just decided when it's going to come my turn, I don't know what's going to come out of my mouth, but it's not going to be that. And so I just told a story that was more funny. It was poking fun at myself about something that I had done recently and a mistake that I had made. So instead of blaming my team or my whatever, I just told a, I was like, you know, here's where my head's at. Because all you, they weren't saying like, give us a team update. They were just saying like, you know, let's all be present to share what's on our mind, how you're feeling right now. And so I did that and that stood out at the break. Everybody was like, dude, I love that story. Um, and you know, the, the lesson there is really like, take a bit of a risk and don't take yourself too seriously inside companies because I think there's a tendency to try to button up and blend in. And, uh, I would say that's not what the best people do. I don't think that's what, I don't think that's how the best people act.

We have this guy at Hampton named Doug, and Doug is a very stereotypical engineer, so he is very black and white. And because of that, he's done a very good job of just being honest constantly. And so if someone's trying to bullshit me, I'll just be like, uh, what's Doug think? Doug, what do you think? And he'll just be like, that's stupid. Or he won't say it that way. He'll be like, I don't think that's the right way. I think this is the right way for these reasons. Or he'll be like, uh, I don't like, I don't exactly understand like branding, but I think that a lot of people like this, this, this, and this, and they like it for these reasons. Therefore, that way is or is not the right way. And it's just, what does Doug, I just always wanna know what's Doug think about this? He's very analytical and he's very honest and he doesn't, because he's, you know, like a normal engineer, he doesn't exactly understand what's hurting my feelings or what isn't hurting my feelings. And I love that about him. I love that. I always want Dougs in my life. People who just don't bullshit me and they'll say something like, that's stupid, that's not stupid. And I appreciate that. That's his brand.

So tho, those are our tips, how to become, I don't know, a superstar inside of a company, how to stand out. How to make a name for yourself inside of a company.

And if you're, uh, if you're, if you're listening on, on iTunes or, uh, Spotify, go to the YouTube and A, subscribe, because we're about to cross 400,000 and B, comment other questions that you have for the new segment, Questionable Advice. If we get any good questions, we'll do it.

I like how you said the YouTube. That's how my dad says it too. That's cool. Go to the YouTube.

Yeah. When I look at, when I hold my phone to take a picture, I use two hands as well. I'm always doing this.

I'm like posting, I'm trying to post a TikTok a day and I love doing it.

Dude, I saw what you said. Yeah, that was great.

Every time I post a TikTok, I feel like I age, I like reverse my age by one month. I'm just getting younger just by TikTok by TikTok. If you want to be young, you do as the young people do.

You got to like, and you're going to, you're squinting your eyes. You're going to hold your phone with two hands and you're going to like look down on it. That's how it feels right now.

Turn the damn thing off.

All right, that's the pod.