Sam and Shaan introduce a new segment called “Questionable Advice” and tackle how to become a superstar employee inside a company. Drawing on their experiences at Twitch, Monkey Inferno, and The Hustle after its acquisition by HubSpot, they share concrete tactics for standing out: writing internal newsletters, building confidence through intelligent questions, working on the A+ problem, fixing paper cut issues, and creating a personal brand inside an organization.
Speakers: Sam Parr (host, co-founder of The Hustle), Shaan Puri (host, founder of Milk Road)
Introduction: Questionable Advice [00:00:00]
Shaan: Just to give you a sense of this — I’m 24 years old, I’m the youngest person in the company, I’m the newest hire in the company, and six months later I got named CEO.
Sam: Prodigy. That’s pretty good. Pretty good, right?
Shaan: And the way to do that is — 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.”
Sam: Does that mean that someone shouldn’t follow the advice, or that we’re just answering questions and giving advice?
Shaan: It means whatever people needed 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 you necessarily should do — we’re saying what we’ve done that works for us. It may or may not work for you. It may not be the best way. It’s just the only way we know.
Shaan: 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? How do you stand out inside of a big company? 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?
Sam: How many employees have you had like that? Every company there’s always one or two.
Shaan: There’s always one or two that are just so clear. What I did was I basically plucked — what are the things that they do? 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 felt like they worked? Because I had to spend two 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 going to talk about the ones that failed because those were embarrassing or not useful. But I will share the ones that worked.
Sam: Dude, what’s crazy is — let me add two backstories to our perspective on this. One, you had someone who worked at Monkey Inferno and all the other companies that Monkey Inferno started. You actually had a few interesting people. The first interesting person was Steve Bartlett, who’s famous for his agency and his podcast Diary of a CEO. I think the second person who’s even more interesting is Faron — a guy who started a company that’s worth tens of billions of dollars. I was shocked that that guy would consider you a coworker. That was an amazing get.
Sam: The second point I want to add to this — you probably had a few other people, like Jason Hitchcock, who are wildly successful. The other thing to add: one of the best compliments I’ve received from you in the last probably 60 days is you texted me and said, “How on Earth did you get Steph Troung,” and I forget who else you named — “how on Earth did you brainwash them into working for you for as long as they did?”
Working With vs. Working For [00:03:30]
Shaan: So we’ve each had a handful of superstars. I don’t ever use the word “work for me” because I hate that. It’s not that — it’s “we work together on something,” and I’m only going to have them for 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. Working with somebody is a partnership, it’s an agreement, it’s a mutually beneficial thing. Versus “I work for you” — there’s a dominant person and a person who just takes orders and does whatever they have to do based on the task list. You never want to be in the “work for” mode. “Work for” is a servant essentially, whereas “working with” is a partnership.
Sam: But it’s okay to have to be in that mode for a little while — actually, for someone who’s interesting. If Shaan Puri doesn’t have a specific need, and some kid is like, “Dude, 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 long term. Working with is how I consider it to be done correctly.
Shaan: I hired a chief of staff just now. This kid basically had a job at, I think, JP Morgan. He 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 I’d be like, “No, not really, I should do it.” He’s like, “How about I come do it for you?” I was like, “I don’t know about you.” 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 can go quit right now if you say you’re in.” I said, “Okay, bet.” And then he went and talked to his boss, quit his job in banking, and now he’s my chief of staff.
And even for him, on day one I told him: “We work with each other, you don’t work for me.” Because I actually want somebody who’s going to treat themselves that way — they’re going to get way more done, they’re going to be more productive, they’re going to be a higher caliber person if they think that way.
Sam: Did you actually say “bet”?
Shaan: Dude, it’s 2022. I’ve got to speak the language.
Internal Newsletter: Building a Brand Inside the Company [00:08:15]
Shaan: All right, so the first category involves communication and writing. Do you want to name a few things you have under that?
Sam: Yeah, okay. I’ll do one simple one: write an internal newsletter.
People know us as the newsletter guys because I created The Hustle, read by millions of people. Shaan created Milk Road, which became the biggest crypto newsletter. But the newsletter thing isn’t just for external audiences. You can have 100,000 subscribers on a newsletter, but if you’re inside a company, what you really want is 20 subscribers — the 20 most interesting people in the company.
What I did when I got to Twitch was — Bezos has something called the S-Team, which is Amazon’s 15 to 20 top lieutenants. Twitch, being owned by Amazon, had its version called the T-Team. I got put on T-Team. So I go to the first meeting and it’s a busy meeting. They’re like, “Oh hey, welcome Shaan — we just acquired you, Shaan, want to say hi?” I say hi for two seconds, but I really don’t know any of these people.
Shaan: So what I did was I created a newsletter for all of the T-Team. And then slowly, whenever I met 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 to the list.” And they’re like, “Okay, cool.”
I copied James Clear’s newsletter format. James Clear does something called 3-2-1. I wrote the 1-2-3 newsletter internally: one photo from my camera roll, two thoughts which were just tweet-length things I’m thinking about inside the company, and three links — just random stuff I’ve seen.
Sam: What type of photos?
Shaan: Usually something not work-related. Culture-building stuff, like a photo from my life — something interesting. I’m not a big Instagram guy, but I kind of get the idea: a photo can say a lot about you and what you’re interested in. It can brag a little bit, like, “My kid learned how to ride a bike this weekend.”
For example, I did one photo that was this list my niece had made. She’s seven, and she wrote her routine: “Ellie’s Day” — Eat, Play, Sleep, Eat, Play, Play, Sleep. And I was like, “Somehow the seven-year-old has it figured out, what are the rest of us doing?”
Shaan: So — one photo, two thoughts, three links. I sent that out every Sunday. The way I framed it: “When I was a startup founder, I used to send this to our investors and board of advisers every Sunday — an update on kind of where my head’s at. Old habits die hard, even though I’m not a startup founder anymore. I’m working at Twitch, but I still have this hour every Sunday. You guys are now my new board of advisers, my new mentors at this company. 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.”
Dude, I can’t tell you how much juice I got out of this. It took me about 45 minutes to write every Sunday, but now I’m getting everyone’s attention. Not everybody loved it — I’m sure some people were like, “Whatever, I don’t care about this.” But it didn’t matter. It got forwarded. There was a VP at Amazon Prime who emailed me like, “Dude, I love these Sunday things, man. I wish we got to work together.” He wasn’t even in the company — it had gotten forwarded to him. And that’s the whole goal: you want to build a brand internally, and one easy hack is the internal newsletter.
Writing History: Control the Information Flow [00:14:00]
Sam: 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. There’s this thing with history I read about — often the person who writes the most popular history book actually controls what we think of history, even if it’s not perfectly accurate. She did that in a good way where it was very tactical.
She was the best Google Sheets maker and a really good Google Slides maker. So she would dictate how the Google Sheets looked for the projects she ran, and eventually for other projects too. That dictated what we tracked, which dictated what we did.
Sam: She made these beautiful sheets that auto-filled. 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. If anyone had a question, if anyone wanted to know anything, they had to go to her. She wasn’t doing this for bad reasons, but she was basically a very powerful person because of that.
You need to get really good at presenting your work and you need to be really loud about it. You have to be great at presenting your work, making presentations, writing stuff, controlling the Google Sheets, making them look presentable and work well. That is incredibly important and not enough people think about that.
Shaan: 100%. The winners write history. And also, you want to be a maker, not a taker. Most people in companies are takers of plans — somebody else writes the plan, somebody else makes the doc, somebody else creates the dashboard, and you just sit on the receiving end.
What I would do when I was at these companies is I would always write my own versions of the plans. This was partly for practice. If I want to be the CEO, I should get reps doing the things the CEO is doing. He’s writing an annual plan? Cool, I’m going to write one too. What would I say? And you write it, you compare it to what they wrote, you see things they did better and things they maybe missed.
Being a plan writer, a proposal writer, an update writer — that’s the thing that actually sharpens your skill. If you want to be a leader, most people think, “I’ll wait till I’m promoted and then I’ll start doing leader things.” That’s not really how it works. You start doing leader things and then you get recognized and promoted. You’ve got to be the plan maker, not the plan taker. Write your own version of all the key stuff: the annual plan, the quarterly update, the launch guide — whatever it is for a given project.
Being Loud: Work in Public [00:18:30]
Shaan: The next thing I would say is — and this is challenging for a lot of people — it’s important to be loud. When I say loud, I don’t mean you have to talk a lot. I just mean you have to make sure everyone knows the cool stuff that you’re doing. There’s a fine line between stealing credit and being loud, but it’s important to let everyone know these are all the amazing things that are happening. You have to present that in a wonderful way where it shows progress, and even if you screwed stuff up, here’s the swings we took.
Sam: I always had to encourage people on this. I’d be like, “Dude, you’ve got to speak up, you’ve got to be louder about this stuff — this is really awesome, you are not inserting yourself into conversations nearly enough.” So yes, being loud is incredibly important to standing out within a company.
Shaan: Exactly. You want to work in public. And like Sam said, it’s not all bragging — people would report in a format like, “Here’s what went well, here’s what didn’t go well, here’s the screw-ups we had this week and what we learned from them.” It doesn’t have to be “everything I did was great and I’m the best.”
However, you’re totally right that you’re only rewarded for what people know about. If what you’re doing can’t be measured or isn’t seen, it might as well have not existed inside a big company. And for a lot of people, that’s very uncomfortable. They wish the world worked differently, where it was purely merit-based and everything was equally visible. It’s just not true. If a tree falls in the forest and no one’s there — you need to be able to highlight what you’re up to. Carve out 10% of your time to doing that.
Titles Matter [00:22:00]
Shaan: Let me tell you one more thing that’s a bit unrelated but very controversial. It took me a long time and a lot of tough challenges to learn this: titles matter.
I imagine when you started your early companies 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 — they matter because of the job you have there, but also the job you can get elsewhere.
Sam: Give me an example, because I would disagree with this. I don’t think they matter that much. What’s the example you’re thinking of?
Shaan: Okay. If you want to be called the head of something — that’s actually really important for the employee. It’s scary for the employer, because if you give someone “head of marketing” you can’t hire someone above them without causing tension. However, for the employee, if they go to a new company, they’re going to say, “Look, I was already head of marketing at this company, I need to be CMO or something of equal seniority.” Additionally, within the business, if you’re the head of blank, everything that happens within that area — you need to have your say, you need to have your finger on the pulse.
Titles seem unimportant to an entrepreneur because you say things like, “It doesn’t matter, we’re all working together.” But they matter for the employee.
Logos Matter: The Stamp Effect [00:24:30]
Shaan: I would also say logos matter. There’s a funny thing that happens where — let’s say you’re building Hampton, a community or membership-based product. If you see someone who ran community or memberships at YPO or Soho House versus some unknown brand, for some reason we attribute all the success of that known company to this person, even if they had very little to do with the winning.
At The Hustle, I had a guy who worked at Facebook and wanted to join us. I was like, “Oh, you’re in,” and we hired him — and he was terrible. But I totally fell victim to that. I do that all the time.
Sam: This happens to me with live streaming. People are like, “Oh, you worked at Twitch — we’re doing live streaming, it’d be amazing to have you.” They don’t know my experience at Twitch. They don’t know what I was doing there. I learned way more about live streaming at my startup that was actually building live streaming. But if I only had that unknown startup name, I would have gotten zero credit as a live-streaming expert.
Shaan: Logos matter a lot. Getting one winner logo — that stamp is cool. Not different than having Harvard or an Ivy League. If you’re good enough to pass that bar, you’re good enough. And one is enough. That’s the key. One problem people get into is they go logo-collecting. One is enough. If you’ve got Harvard, you don’t need another MBA from somewhere else. If you have Facebook, you don’t have to make the next one Google — you can take a bit more variance on the next one, because the Facebook stamp will carry you.
Managers Matter [00:27:15]
Shaan: The other thing I’d say is managers matter. When we got acquired by Twitch, we were getting interviewed by people and I was supposed to be getting onboarded but I was also diligencing them — because I know managers matter. People don’t quit jobs, they quit managers. 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 stuff that goes on.
They first tried to put me under somebody and I was like, “No, no, no, no. I’m not working for that guy.” They’re like, “What’s the problem?” I was like, “Nice guy, but I’m not working for him.” And they were like… I said, “Is there anybody else? Because these two other people — I liked them. They’re clearly close with the CEO, they’re doing all the interesting projects.” This other guy was working on trust and safety or maintenance — plumbing under the bridge. I’m not trying to work on boring projects with a guy who has no respect in the org.
Pick somebody you’re going to learn a lot from, but also somebody who has surface area — who can get stuff done. And switch if you don’t like where you’re at. Try to actively switch.
Sam: Dude, when I sold The Hustle to HubSpot, the plan early on was I’m out of the picture and just doing the pod. But they were like, “How about VP of Marketing, you report to this guy?” And I was like, “Can we give me a lower title? Make Brad, my VP, the actual VP, and I’ll report to him.” It was just way better. I was like, “Yeah, let’s bring it down. I’m not going to be a VP.”
The 5% Rule [00:30:00]
Shaan: All right. I have something I call the five percent rule. I learned this from Faron.
When we got acquired by Twitch, we were supposed to work on a specific thing. We were takers — we got acquired to do this, let’s do this. And Faron wasn’t very motivated. I was like, “Dude, come on, let’s try to do a good job here. I get it, it’s not like when it was our company, but you seem totally checked out.” And he was like, “No, no, I’m not checked out with the company.” He pulled up the overall company dashboard and said, “Best case scenario — this thing that we’re building — which of these metrics changes?” I’m looking at the number one dashboard for the company, the key KPIs. I was like, “Well… none of these.” He’s like, “Go to page three.” I go to page three — subdivision, subdivision, and then this one. He goes, “Cool. Let’s say we change that one. How much do you think that changes the overall picture? Don’t you think that if we do a great job, we should make at least a 5% impact in the company?”
I was like — my ego gets involved — “Yeah, of course, 5% is low, actually.” He’s like, “I just think we’re capable of doing something that’s going to move the needle 5%. If we succeeded and it couldn’t even move the needle 5%, I’d feel like it was a waste of time.” And that’s the 5% rule.
We immediately switched to something that would do that, and it was such a good decision. In the same way that Naval says you want to place an absurd hourly rate on your time so you value it and put a price tag on it — this is the same thing inside a company. Put a price tag on your projects. You simply will not work on projects that can’t move the needle for the company. If you carry yourself as somebody who can actually move the deal for the company, it’s sort of self-fulfilling. You raise your standard, and now that’s what you do.
Sam: Dude, you were lucky to have Faron. So Faron — I don’t know if he was the co-founder or one of the first hires at App Lovin. App Lovin is an adtech company, now around a $130 billion market cap. He wasn’t one of the co-founders — he was just a random engineer they hired, like person nine. Within a couple months they were like, “All right, this guy’s the guy.” They went to him and said, “Hey, I think we built this team wrong. Now that we see you and we look at the other eight people we hired before you — we realize we did this backwards. Can you fire all these people and rehire a new team of people like you?” He did that, ended up getting a co-founder equity stake, the thing goes public, it’s like a $20 billion company.
Same thing happened — I hired him at Monkey Inferno as an Android engineer. Above him: director of engineering, CTO, me. Within a couple months I was like, “This guy is a superstar. Android engineer is simply the wrong title.” I told him, “You’re going to end up in a different role, just give me a month to figure this out.” Within a month we had switched it up and he ended up becoming CTO and we basically rebuilt the whole team around him.
He has this master sensei-like wisdom to him. Whenever he says something, I believe him. And more importantly, all the engineers you’ll ever hire will believe him too. He’s a leader of engineers, which is extremely valuable.
Fix Your Zoom Setup [00:38:00]
Shaan: Okay, here’s a simple one: fix your Zoom setup. Just don’t look like garbage on every call. In fact, you should look incredible on every call. It doesn’t cost that much to do it.
You can do it with an iPhone app called Camo — you can download that and get DSLR quality from your iPhone. That’s what I’m recording on right now. If you want to go one better, just get a light off Amazon for 50 bucks. That app and that light will put you in the top 1% of people at work in terms of how you look. Do that, and also buy a podcasting mic — a Blue Yeti or a Shure microphone. Just look good and sound good. No matter how good your ideas are, if they’re wrapped up in a crap sandwich, they’re going to come across poorly. It’s the digital equivalent of dressing well.
Sam: I make this a rule at my company. I’ll get really tactical: I’m using a Shure MV7 USB mic — that’s $200. An iPhone with a $50 Camo subscription. A $150 Elgato key light. That’s my travel kit. So if you think that looks good enough, that’s what it is. It’s going to be better than most people’s up-the-nose shot with crappy audio sitting in a closet somewhere.
Confidence Through Intelligent Questions [00:40:30]
Shaan: Faron is actually a great example of this too. When you get into a group — whether it’s work or any other type of group — often the most confident person is not usually the smartest person, but the most confident person wins. And I think confidence is displayed by saying things like, “This is the path we’re going to go down. I have a 60% certainty that this is going to work, my logic is X, Y, and Z, but this is the answer — at least this is the answer for us to try.”
At a small company like anything I’ve run, you work with the CEO or owner. At a larger company it still matters with managers and VPs. The confident person who says “this is the way,” dictates the way, explains their reasoning — you start believing in them. You still have to be right more than you’re wrong. But confident people tend to succeed the most.
Sam: I’ll give you two things. One — what you just described is basically the McKinsey Pyramid Principle. Are you aware of this?
Shaan: No.
Sam: So basically, most people get communication wrong inside a company because they bury the lead. They’ll go beginning, middle, end — like a story — and the conclusion is at the end. What busy people, which are most of the leaders inside companies, want is the opposite: lead with the recommendation first. “My recommendation is we should do this, for these three reasons: number one, number two, number three. I believe reason one because we have evidence. Reason two we don’t have evidence for yet, but it’s a reversible decision. Reason three — blah blah blah.” Stack the main conclusion first and then support it underneath. That’s just a simple communication flip.
Sam: Another communication thing I learned: the What-Why-So What framework. EMT from Twitch taught me this. It’s: what happened or what’s going to happen, why it happened or why we’re going to do it, and so what — what’s the takeaway.
Give an example: “What happened is revenue is down 10% this month. Why? Because last month we ran an extra promotion that artificially inflated last month’s revenue — this month is actually normal. So what? We’re going to continue as planned, and we’re actually going to consider running those extra promotions every other month because they seem to provide a boost.”
Just write “What, Why, So What” on your paper before you figure out what you’re going to say in an email or a document. Bullet point under each, and that’s 80 to 90% of the material done.
Shaan: And I find what helps is if you put a confidence level in there. A lot of times people think “confident” means 99% or 100% certainty. You shouldn’t do that. Be conservative — say “I’m 65% certain” or “I actually think there’s a 30% chance this works, but if it does, the upside returns are quite huge, and if it doesn’t, it’s reversible in these ways.” You want a soft landing if you fail.
Managing Expectations and Thinking in Probabilities [00:45:30]
Sam: Superstars do three things. Number one, they think in probabilities, not certainties — that’s what you just described. Number two, they manage expectations. You don’t need to overpromise and underdeliver. Under-promise, overdeliver is a better mindset.
I remember going into a big partnership pitch meeting. We thought our technology would give them a yield 100 times better than their current thing. I was like, “Slam dunk, put that on the slide — 100x better.” We go into the meeting, and I notice my dad has changed the slide. It only says “three times better.” I’m like, “Dude, you messed up — what happened?” He’s like, “Did you see their faces about three times better? They were over the moon. That other stuff is now my dry powder. If I said 100x and we came in at 80x, it would be seen as we didn’t deliver on what we promised.”
The principle holds true: only sell to the amount you need to get them to agree to greenlight the thing, but don’t over-promise beyond that. Beating your numbers is how you exceed expectations and build trust.
Shaan: So as an example — Google “Uber seed deck.” In 2008, Uber was just getting started, raising only $200,000. On slide 20, they have a slide that says “Potential Outcomes” — best case scenario becomes a market leader with over a billion dollars in annual revenue; realistic scenario gets 5% of the top cities and makes around $20–30 million a year in profit; worst case, we stay a 100-client services business that just saves time for San Francisco-based executives. Versus when you see a pitch deck where everything is up and to the right — you don’t trust it. You’re like, “Dude, you’re saying something outlandish with a huge degree of certainty.”
Shaan: On confidence — people think confidence comes from having answers. No, confidence comes through asking intelligent questions. Any leader can tell a person’s quality of thinking by the quality of their questions. It always stands out when somebody asks a question that’s on point or breaks the frame of how you’re thinking.
You’re in a messy meeting, options A and B both seem bad. Instead of just picking one, somebody asks a different question: “What would an easy solution look like here?” or “We’ve been saying this thing — just want to say this out loud: is that true? Do we have data to support that?” or “We’re trying to solve this problem from scratch — we’re not the only ones who’ve had this problem. How have other people solved it? How have we solved it in the past?” Anybody asking questions that are going to cut to the answer faster — that’s a different way of showing confidence versus “me me me, I have the answer.”
Sam: Dude, the one question I love that all my employees hate: they’ll give a 12-month plan and I’m like, “Yeah — how do we do this in four weeks?”
Shaan: The best people frame that question nicely. Faron used to say: “I’m going to say something — you can beat me up if you think this is a terrible idea, feel free, but I just want to say it.” And then he’d say the thing. It’s such a disarming way of bringing up a counter-current idea. You’re always like, “Oh Faron, we’re not going to beat you up about this idea.”
This other guy Dan — now the CEO of Twitch — would do this thing in meetings where he’d slow everybody down. He’d say, “You know, it’s one thing to say A, B, and C” — lay out an argument quickly — “but it’s another thing if we were going to say D, E, and F.” He’d just frame it slowly for everybody. The person who can synthesize the arguments — “what I’m hearing you say is A and C, I just want to make sure it’s A, B, and C and not actually D, E, and F” — who brings that clarity to the meeting is always the essential person. The person who helps you figure out the solution when it felt like everybody was just talking in circles.
Build Your Talent Rolodex [00:52:00]
Shaan: Want to do one or two more?
Sam: Yeah, okay.
Shaan: Here’s an easy one. Let’s say you’re inside a company today but you want to start a company someday. You need to start creating your own version of the Midas list: who are the five most interesting people inside this company that you would want to recruit later on?
What I did was — at the beginning I said, “While I’m here at this job, here’s what I want out of this.” I wrote down a list. One: I want to learn one or two things about leading a company that I don’t know today, because these people have managed bigger teams better than I have. Two: I want to have the respect of the CEO. I want him to be able to say, “If you leave here and tell me you’re going to start a company, I’d want to write the first check.” That would be a signal that I did well.
Would EMT do that for you?
Sam: Yeah. He actually slacked me one time, out of the blue, basically that exact thing: “I wish we could keep you forever, I don’t think that’s going to happen — if you ever decide to do something, I’d love to back you.” I was like, “Oh man, what a compliment.” And I actually showed him — “That was on my list of things I said I wanted out of this experience.” Cool full-circle moment.
Shaan: The third thing on my list: I want to walk out of here with five more people in my talent Rolodex that I could reach out to if I ever needed to hire. I was like, “Oh, this girl in data science — massively underrated, she’s the real one who delivers the work. She’s kind of junior here, but she would be somebody I would poach right away.” Or, “This guy on the sales team — God, that guy was smooth. If I ever have a thing for sales, I know who to contact.”
Right now with one of our new companies, I’m trying to fill a role, and those are the people I went to first: “Hey, I have no idea if you’re available, but I made this list before of who are the five people I would love to work with someday, and you were on it. That day is here — what are you up to?”
Your talent Rolodex becomes a limiting factor as you try to build new companies. I’m sure you have people you’d love to speed-dial and bring on board to a new thing. You did this with Hampton, right? I noticed there are some people there who were at The Hustle.
Sam: Yeah. Actually, I think someone said something like: a really good question to ask yourself is, if you were starting your thing again, would you hire the same people and do it the same way? In many cases you say, “No, I would change this, this, and this.” And the advice was: just do that right now.
Shaan: Yeah. In the mafia — and Succession kind of stole the phrase — they say, “He’s a serious person.” A serious person means hitter. They’ll say, “Oh, he’s serious. Yeah, that guy’s serious.” Or, “He’s not a serious person.” You want to find serious people.
Paper Cut Problems and the A+ Problem [00:57:00]
Sam: I have two more little ones, real fast. One is: find a paper-cut problem.
I’ve noticed that a lot of people who do well in companies do this in the first two weeks when they join: they find something that’s been an annoyance that nobody’s ever fixed because it’s never the most important thing. And they just go clean it up, voluntarily. I call this the paper-cut problem — it’s the kind of thing that’s a bit annoying, you’re not bleeding out, you don’t have to go to the hospital. But if somebody fixed it you’d be like, “Dude, thank you, that would actually stand out.”
I know several people who did this. They go to a company and immediately identify, “Here’s some annoyance that two people have referenced — I bet this annoys everybody. And if I just spent one Saturday working on this, I could fix it.” And they did that, and it boosted their stock so much.
Shaan: When I was in seventh grade, I had a job at a bakery. I’d clean the floors and wash dishes. There was a shelf where we’d put these dried dishes, and the shelf was broken. We hired another janitor to work with me. I had worked there for eight months and this shelf was always broken — a pain in the ass. Within his first week, this new guy fixed that shelf. I immediately thought: that’s the way to do things.
Sam: Exactly. And by the way, you get rewarded for doing things you didn’t have to do. If you just do your job, that’s called your job — you do not get extra recognition for that. By definition, you have to find something beyond your job if you really want to stand out. Take that principle and make it actionable: go look for it. As soon as you start looking, you’ll see it. The guy who’s been there eight months has gone blind to it. But for a new person who’s paying attention, you’ll see it right away. Go fix that thing.
Shaan: This guy’s head janitor now. But honestly — if you’re going to be a janitor, be the head janitor. Be the best goddamn janitor anybody’s ever seen.
Sam: Okay, I’ve got one practical one and one fun one. Practical: find the A+ problem.
At any given time in any company, there is the A+ problem — the thing that’s keeping the exec team up at night. What I did was I just found the A+ problem and only worked on that. I would do my main job kind of 70%, or 50%, or sometimes 0% — I’d just put it on pause, because honestly it didn’t matter relative to the A+ problem.
I took a little more risk than most people because I didn’t care if I ever got fired. Actually, we had a friend who said, “There were layoffs this week at our company, and sadly I was not impacted.”
Shaan: Exactly.
Sam: I remember — I was at a company and basically a competitor was attacking them and stealing their top customer. I figured, well, that’s probably the A+ problem. So I did some analysis, wrote up a two-page doc, and sent it to the CEO: “Hey, I have no idea who’s working on this, but I was curious so I dug in, and here’s what I found.” I immediately got added into a group chat: “Hey, Shaan’s in on this now.”
That’s what you want — 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 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.
Creating a Personal Brand Inside the Company [01:02:00]
Sam: What’s your last fun one?
Shaan: The last fun one is: create a brand for yourself. There are all these moments inside companies — introductions, team offsites — where you have two choices: you’re either going to blend in or you’re going to stand out. The best way to stand out is to be yourself. And the way to be yourself is to just remove the filter.
What was your brand?
Sam: I think there’ve been a couple. At Monkey Inferno, you make an impact, but you also have to build some sort of brand for yourself. Mine was I was going to be the “massive action” person. Whatever the thing was, I was going to take action on it immediately. And I was going to do the stuff that nobody else wants to do. “We don’t know if people will like this — who cares, give me the prototype.” I’d go to the mall and talk to people and come back with written feedback. Just stuff that nobody else really wanted to do.
It built this thing: I’m going to consistently take action, I’m going to have a higher bias for action than anybody else. And I would talk about that. I remember this one guy did an intro and he said, “I don’t know anything about art, I don’t know anything about politics, I don’t even know where the remote is in my house. But the one thing I know is how to structure deals, and today I’m going to tell you about that.” And I thought — what a fantastic intro. As much as your brand is going to be that you’re good at X, Y, and Z, you could also say how little you know about these other three things. Just be honest about it, even poke fun at yourself.
So I would tell people: “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 iterating from there. So I’m going to go crazy on that. What you’re going to get in the next six weeks is me going crazy on that. Sound good?” And they’re like, “Great.”
It’s like Warren Buffett says: look for partners with high IQ, ethical, and a lot of energy. I was like, well — two out of three isn’t bad. I definitely am ethical and I have a ton of energy. My wheels are spinning fast. If you just point me in the right direction, the car will run, and it’ll run quickly.
Shaan: I had the exact same brand. When we got acquired I just was like, “Hey, I’m a startup guy inside this big company. I’ve only ever worked in startups. I don’t know anything about a big company — I’m probably going to make some mistakes that are obvious things you should do in 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. You guys tell me what parts of that are working or not.”
That’s part of the brand. But the other part is: stand out a little bit. I remember sitting at an offsite — “How about everybody just share how things are going?” Person one said this boring thing about work: “Here’s what I’m doing, here’s the problem I’m having” — just kind of bitching and moaning with a very bland story. And I just decided: when it’s my turn, I don’t know what’s going to come out of my mouth, but it’s not going to be that.
So I just told a story that was more funny, poking fun at myself about a mistake I had made. Instead of blaming my team, I was like, “Here’s where my head’s at.” They weren’t asking for a team update — they were just saying, “Let’s all be present, share what’s on your mind.” I did that, and it stood out. At the break, everybody was like, “Dude, I loved that story.”
The lesson there is: take a bit of a risk and don’t take yourself too seriously inside companies. There’s a tendency to try to button up and blend in. I would say that’s not what the best people do.
Sam: We have this guy at Hampton named Doug, and Doug is a very stereotypical engineer — very black and white. Because of that, he’s done a very good job of just being honest constantly. So if someone’s trying to give me a line, I’ll just be like, “What does Doug think? Doug, what do you think?” And he’ll just be like, “I don’t think that’s the right way. I think this is the right way, for these reasons.” Or, “I don’t exactly understand branding, but I think a lot of people like this, this, and this, for these reasons — therefore that way is or isn’t right.”
I always want to know what Doug thinks. He’s very analytical and very honest. And I love that about him. I always want a Doug in my life — people who won’t give me a line, who will just say, “That’s wrong” or “that’s right.” That’s his brand.
Wrap-Up [01:08:00]
Shaan: So those are our tips: how to become a superstar inside a company, how to stand out, how to make a name for yourself inside an organization.
And if you’re listening on iTunes or Spotify, go to the YouTube and subscribe — we’re about to cross 400,000. And comment other questions that you have for the new segment, Questionable Advice. If we get any good questions, we’ll do it again.
Sam: I like how you said “the YouTube.” That’s how my dad says it too.
Shaan: Go to the YouTube.
Sam: When I hold my phone to take a picture, I use two hands as well. I’m trying to post a TikTok a day and I love doing it. Every time I post a TikTok I feel like I reverse my age by one month. Just getting younger, TikTok by TikTok.
Shaan: If you want to be young, you do as the young people do. You’ve got to hold your phone with two hands and look down on it. Turn the damn thing off. All right, that’s the pod.