7 Years of Agency Operating Lessons (Part 3)
In this third episode of his "7 Years of Agency Operating Lessons" series, Eric Siu reflects on the hard‑earned principles that have shaped Single Grain, the digital‑marketing agency he bought for $2 and later paid six figures for. He emphasizes the need for relentless over‑communication of mission, vision, and values through weekly letters, belt meetings, town halls, and quarterly post‑mortems. Siu outlines the three core duties of a CEO—setting vision, recruiting top talent, and keeping cash in the bank—and warns against the early‑stage mistake of trying to do everything yourself. He shares a hiring framework inspired by Jeff Bezos and Chamath Palihapitiya, including questions about admiration, intelligence, cultural fit, passion, and recent reading. The episode also covers the balance between giving direct advice and coaching, the utility of personality assessments (StrengthsFinder, PRINT) and personal “user guides” for effective collaboration, and his evolution from viewing a company as a democracy to a merit‑based or autocratic model where the leader makes final calls. Siu introduces Jeff Bezos’s Type 1 (irreversible) vs. Type 2 (reversible) decision taxonomy, advising deliberation on high‑stakes choices and speed on low‑stakes ones. Finally, he discusses acquisition strategy—aiming to make money on the buy and maintain a margin of safety—using his own $2 purchase as an example, and ends with a call‑to‑action for aspiring agency founders.
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All right. So this is part 3 of a multi-part series around 7 years of lessons from operating, um, the ad agency or just operating any company in general. And again, this is just a recap. Um, Single Grain is my ad agency that I own. And I, again, I bought the company for $2 out of pocket. So negotiated a good deal as my first kind of, or one of my first few, um, you know, kind of M&A deals. I'm air quoting right now, cause it's not like it was a huge deal to begin with, but $2 out of pocket. Um, and then paid 6 figures. That was kind of the buyout over time. And then the contingency was if the company failed, I would owe nothing. So here's the thing. I'll restart again from number one. But immediately what comes to mind is, you know, earlier I talked about, you know, having core values, having a great culture as well, making it all about the people, hiring slow, firing fast. That's all great. But I learned as a leader, what you have to do is you have to overcommunicate. You have to overcommunicate to the point where you're being annoying because people forget things quickly, they're so busy. So mission, vision, values, right? That's what you have to— the leader needs to, you know, make sure that the vision happens, right? The leader's responsibility, I guess that'll be the second part. So anyway, we'll start with vision first. So mission, vision, values, you have to continually overcommunicate, right? You're always talking about values. So how do you— How do you make it intentional, right? How you're always talking about the value. So we talked about how, you know, on Thursdays we have this belt meeting where people share their personal professional wins and then they nominate someone for the belt and they nominate them based on certain core values. So there's that, you know, talk about the mission. Like as a leader, what is helpful is every week or so you send a letter saying, hey, here are your musings, here's what you're thinking about. And then talk and reiterate the mission again, reiterate the mission. What's the mission, right? So If you ask me what my personal mission is for the rest of my life, it's to level up the entire world. It's a very grand mission, right? But when you think about on the Single Grain side of things, it's really helping, you know, reputable companies grow through marketing. And that's what it ultimately is. And, you know, that's a broad mission, but it's something that you can go after because, you know, when you think about Google's mission, it's their mission is to organize the world's information. And that's probably never going to be achieved, at least I'm not sure it's going to be achieved in our lifetime. So we'll see what happens there. But they've done a pretty good job of it so far. That's what it is. You're ultimately, you're putting the right processes in place where a conversation is allowed to happen around this. You as a leader, you're constantly reinforcing, hey, here's what it is. Here's what the mission is, right? Here— oh, here comes Eric again with his vision stuff. Here comes Eric again with the core value stuff. But you know what? At that point, you're just starting to get enough, right? And I would recommend every month or so, you know, doing a town hall, a town hall meeting, going over numbers, going over objectives and key results, talking through, you know, new hires that are coming in, talk about musings, you know, sending a Q&A form out there where people are able to ask questions anonymously. People can make suggestions as well. Just a— it's a great time for that. And every quarter or so you do kind of a quarterly postmortem as well. And then you just keep going from there. It's constant communication, constant communication, keeping everyone aligned. That's what it is. It's holding alignment and your core values help drive alignment as well. When it comes to going back to vision, so, you know, a CEO's job, it's ultimately 3 things. If you think about it, it's the vision, it's recruiting, right? Recruiting. And then it is financing. So it's keeping cash in the bank. But I say financing, that could be raising money as well. That can be raising money as in it could be debt or through investors, whatever it is exactly. You can, you can raise money. Your job is to keep the company alive, to keep cash in the bank. Okay, so financing, vision, you know, fulfilling the vision, making it happen. And if people don't fit with the vision that that that has been defined, then you might need to get rid of them. And then recruiting too. And and so if you think about it, like the CEO's job is not to try to do everything and get in the day to day. It's to try to get the right people, the right people that are smarter than you know her or him and. You know, just get out of the way and make sure that they get what they need. That's what a CEO's job is. My misinterpretation in the early days was I was such a good, you know, leader. I was such a good manager, like a VP of marketing type person, that I thought my job was to come in and do everything. Even if you can do it at a 10 out of 10 and you're trying to do sales, you're trying to do marketing, you're trying to do all these different things. And by the way, that's exactly what I was doing in the early days. You end up not being able to work on the strategic things. The the big vision things, and ultimately the buck starts and stops with you as a CEO. So you know it's your fault. That's what it is. You know those are the three jobs again. It's vision, financing, right? Keeping cash in the bank, and recruiting. Super super important. Boring but important. It it brings out the leverage, right? You're constantly talking to people. You know even if you're not going to hire them right now, it's just having that conversation. Hey, how are things going? How are things going? checking with them later, hey, or even referring them to another job and maybe they'll come back to you later, right? You're playing the long game here and you want to work with people that you want to work with long-term and that's what it is. And so the third thing I would say is when it comes down to hiring, I have a framework around it and I want to share some questions that I ask. So, you know, I get these from kind of a whole host of people. Some are from Jeff Bezos from Amazon, some are from Chamath Palihapitiya of Social Capital and You know, some Jeff Bezos questions I like are, you know, do I admire this person? So if I'm face to face with someone, do I admire this person? Second thing is, do I think this person's smarter than me? Because I want to constantly be raising the bar at the company, right? Do I think this person's smarter than me? And, you know, would I like hanging out with this person out of work? So personally, I just like to work. That's just me, right? But some people, you just want to think about like, would you be okay hanging out with this person in an outside environment, you know, at a bar, right? You know, one-on-one or in a barbecue, family barbecue setting. So in a group setting and in a one-on-one setting, would you want to hang out with this person? And I would also ask this. I mean, this comes from Chamath, and you know, the question he— the one question he's found a lot of value from is asking that person like, what are they passionate about? So Eric, what are you passionate about? Can you teach me for 5 minutes about this thing that you're really passionate about? One time we did this, and you know, this person just started talking about how she was buying real estate and how she was getting good deals, and that was really fascinating to me because I didn't know these things. And so you want to see if they're good at teaching, you know, are they a good learner as well? And oftentimes I like to ask, you know, what's the most compelling thing they've read recently as well? That's just a question for myself because I'm curious because I like learning. And again, we always have people do a homework assignment because, you know, sure, they can interview well, but you know, when push comes to shove, can you actually do the work? How well do you do the work? Can you hit deadlines? Do you communicate well? All those little things add up. All these little nuances add up. Also, this might be number 4, but it's very important to strike a balance between giving direct advice and kind of, you know, coaching people into it, right? So, and you want to be very specific too. Sometimes you might be saying, hey, I'm giving you advice, or sometimes you might be, hey, you know, this is a, this is a coaching opportunity. When you give someone advice, you're not giving them the opportunity to figure out the answer on their own, and they might not necessarily buy in, that maybe they're just doing what you're telling them to do. When you coach them, when you, when you try to tease the answer out of them, it might take longer. And personally, sometimes I still struggle with it because look, I talk really fast. And I want things to happen quickly, right? And so, you know, you ask them like, hey, like, how would you have done this differently? Well, what about this? Have you considered this, right? And then they'll figure out the answer on their own. But when they have that aha moment, it's so much more powerful, right? So you have to, you have to strike the balance there. If they're more senior and you trust them more, maybe it's more coaching. But if they're more junior and it's a high-stakes type of scenario, you might need to jump in, give advice. I would say in some scenarios you might even jump in and need to micromanage because if they're very junior, again, it's a super high-stakes scenario where it's like closing a million-dollar deal or whatever, you might need to jump in, right? So it's always, you know, little balances and deciding what tool you want to deploy. And so this is number 5, I believe. Personality tests actually go a long way. And I used to think they were a bunch of ho-hum. And I've taken a whole host of them. I've taken the StrengthsFinder, which is great for me personally. It tells me, you know, it says I like to focus. So look, I've kind of focused around this marketing niche. And, you know, one of the other things is around activations. I like to activate others that are around me, and competition is one of them as well. That actually comes from my kind of gaming years when I used to play competitively, and also just my childhood growing up. I learned to be competitive because my parents pushed me a lot, and then I wanted to, you know, I wanted to, you know, be competitive and show them that I've got it, right? So all these things add up because when you look at the StrengthsFinder, And for the entire company, we actually show everyone's strengths. And so you can see, you get an idea of what makes them tick and how to best work with them, right? And that ties, that ties in with the next personality test, which is called the PRINT survey. It shows you what your triggers are. So for my triggers, and I encourage anybody that works with me to read the PRINT survey, one of my triggers is people that are really long-winded. So if they keep talking for a long time, I just totally shut down. You know, not knowing kind of what's going on or, Um, just there's a lot of things that are true with the triggers and you can see if I'm triggered, I'll have these shadow behaviors which are kind of the opposite of my positive behaviors. So all these things, like these personality tests don't take long, 20 minutes, 10 minutes or so, and they're worth a lot because then you can basically— what you can do afterwards is you can create a user guide. So I have a user guide on working with me, what, um, what, how to best work with me, how to best communicate with me, what my shortcomings are, what I think my weaknesses are. All these things. And then at the very end, I put these links to these different, um, these different tests. And I sent it to my executive assistant, and she knows how to best work with me. And these go so far. I think everyone needs a user manual to, to work with. Um, and so, you know, user guides are great. I think personality tests are great as well. And I think this is number 6 for over here. I used to think this. I used to think a company was a democracy. So I used to think, you know, it's, it's all about, um, you know, The political game, you know, making sure I'm well-liked. And I think those things are important, right? Making sure that you're well-liked. And I think, yes, you're gonna— anytime you have people involved, like groups of people, you're gonna have politics. But, you know, what I would say is that in terms of the political setup, it's not a democracy. I used to think it's democracy, like you're all supposed to vote on things and then, you know, majority wins. No, you know, in many cases, You know, you have a meritocracy where the people that have accomplished a lot and are doing a lot, you know, maybe their vote might count more, so you can think of it that way. But in other cases, it's an autocracy, meaning that you have one person that's calling the shots. You have— and hopefully you have a really good leader, that's why the leader is really important. The leader will— a good leader will listen, will listen to the feedback, you know, and then balance it out with what are the long-term goals and then figure out from there how to best use that feedback. Sometimes they'll discard the feedback but other times, they'll use the feedback and integrate it with kind of, you know, the— well, the best foot forward, right? The best path forward. When I used to think as a democracy, things would move a lot slower, right? We'll wait, we'll vote and then if some person doesn't feel like they're heard, then they'll get upset and what I learned afterwards is just straight up, you know what? I'm making the decision. Like, this is the decision I'm making, I, you know, I'm the leader and this is my call. What I found afterwards is they just don't say anything afterwards and that's good. And I think it's really important, this comes from Jeff Bezos, for people to understand that they're not always going to get their way and, you know, it's, it's okay to disagree and commit. And if they don't want to work at the company anymore, they don't want to follow your decision as a leader, that's okay. You know, they can go work somewhere else, right? And that's what it is. It is not a democracy because if everyone voted one way, right, then sometimes it's not the best thing for the long term. Like, And by the way, do they understand all the goals of the company? Do they understand the context? Do they understand what else is at risk? Do they have the same, you know, high-level view that you have as a leader? Probably not. And that's why you have to ultimately— the decision falls back on you and you are responsible for everything. The buck starts and stops with you. You know, at the end of the day, and if anything goes wrong, it's your fault. It all comes down to you. Someone doesn't hit their goals, it's your fault. All right? Because Let's say it's someone that reports to another manager on the team. Well, you put that manager there, right? And that manager couldn't figure it out or you couldn't coach the other manager to figure it out. So, it all comes down to you. So, I've learned to take the blame. And when things go well, you give away all the credit because it's free. And so, you have to learn that it's really not about you there. It's about, you know, dishing out as much credit as possible and taking the blame wherever you can, apologizing too. And I think people will respect you a long way. I don't think, I know. When you actually go out there and you apologize and you backtrack, people respect you more. You seem like you're relatable, you're being vulnerable, and just call yourself out in addition to calling other people out, in addition to holding other people accountable because accountability is one of our core values. People respect you for that, for upholding the core values. When you don't uphold the core values, you are slowly breaking down the company and people will respect you less and less for it and they'll they'll start to think that the core values are lip service. The final thing I want to say is this. There's 2 types of decisions, and I got this from— here we go, Jeff Bezos again. So, there are Type 1 decisions and there are Type 2 decisions. So, Type 1 decisions are irreversible, so hard to reverse, okay? Type 2 decisions will be very reversible decisions. So, a lot of decisions are Type 2, so they're pretty easily reversed. Now, Type 1, what's an example of that? Well, getting married to someone. If I get married to someone, it's kind of hard to just like break it the next day, right? Type 1 decision might be buying, you know, getting myself locked into a long lease or something like that. That's hard to just easily break from. And so you want to have flexibility, right? Type 2 would be like running an A/B test or something like that. It's easily reversed. And so you're gonna find in life that if you are approached with the Type 1 decision, you want to be more deliberate about it. So let's say you're making— you're hiring a high-powered executive and you're gonna have to incentivize them accordingly. You're gonna have to think through that, you know, think through all the consequences around or what needs to happen, right? The onboarding, how's that look? You know, who are they gonna work with exactly? All the little things that make that work. And if it's Type 2, just move fast on it. Type 2, like, you can— if you can— if it's easily reversed, just do it. Again, if it comes back to Type 1, it's like, oh, you're changing the infrastructure of— the entire infrastructure of your software, you should probably think about it, you should be deliberate about it. But, you know, move fast on Type 2, which is the vast majority of the time, and then Type 1, Take your time on it. I'll give you a bonus. Bonus one is this actually ends the whole thing, but acquiring things over the years, I've realized that you should be trying to make money on the buy. Meaning that if I buy something, I— if I'm thinking like Warren Buffett, I want to have a margin of safety. So let's say I'm buying a stock for $100 and I actually think it's worth $500. I have a good, you know, $400 margin of safety right there, right? So I buy it, I've made money on the buy already. And if it goes up after that, you know, that's icing on the cake. And that's what you're hoping for as well. So if you're looking to acquire something, you should be trying to make money on the buy. And I certainly think that I made money on the buy with Single Grain because I paid $2 out of pocket. I really didn't pay anything out of my pocket overall. And so that's how you want to be doing deals in, you know, in the future if you're ever gonna do deals, which I highly recommend. Once you start to build some leverage, build some capital up, build a great company, start to think about how you can reinvest and grow even more. And assuming you don't have, you know, a lot of other upkeep on personally, then, you know, do take as much risk as you want. That's up to you. I personally, I enjoy the risk, kind of holds me accountable as well. So anyway, if you enjoyed this, if you want to grow or start your consulting agency service type business, you can book a strategy call. Go to singlegrain.com/call. You can book it, fill out an application over there. It's free to do it. And we will find a time to chat with you. And if you're not interested, well, just rate, review, and subscribe. Help us grow this podcast or help us grow the YouTube. All right. It helps a lot. So that is it for today and we'll see you tomorrow.
