How Wes Kao coaches founders to influence, lead and get what they want | Wes Kao (Executive coach, co-founder of Maven)

Brett: Thanks again for joining us, Wes. 

Wes: Yeah, really excited to be here, Brett. 

Brett: I wondered have you spent time thinking about charisma in the context of communicating and company building feels like one of those things that's not like fully explored and I, I was curious if you've thought much about it particularly. Because I think you're quite charismatic. I dunno if you identify that way. 

Wes: I feel like being charismatic is one of those things that other people can call you, but if you call yourself charismatic, you seem like a little bit of a jerk, but thank you. Like being a 

Brett: visionary or something like that. 

Wes: Exactly, exactly.

Yes. 

Brett: Gross. If you say it about yourself. 

Wes: I haven't spent too much time thinking about charisma as a topic, but I, off the top of my head, I think there are so many different ways to be charismatic. You know, you see founders of all types, styles, idiosyncrasies being successful. And so I think the main thought with charisma and leaning into being more charismatic is thinking more about what makes you, you instead of trying to copy someone else and having those tactics fall flat or having it feel inauthentic, leaning more into your own idiosyncrasies.

One of my life mottos, uh, especially in recent years is a little bit silly, but I'm gonna share it with you. It's be the mees me. I saw this, I think like on a Facebook post a couple years ago, someone had posted that their toddler said they wanted to be the mees Me. And I saw that and I was like, I love this.

Yes. Like, you know, we all have read adages, like know thyself, you know, be yourself, et cetera. But there's something about be the mees Me that just feels so pure, so raw. So, you know, I am me. Like how can I lean more into the things that make me, me? And you can kind of unpack it in so many different directions.

But I, I think that charisma kind of comes down to leaning into being more of yourself. 

Brett: So how does that manifest itself for you? What have you figured out about yourself, and then how does it translate into all the things that you do and the way in which you behave? 

Wes: That is a big question. Um, I'm gonna, I'm gonna scratch at the surface of it here probably. I think in the past, I thought that leaders had to look and act a certain way. Namely, you know, much more serious, much more formal. And I think I'm a pretty professional person, but I don't think I'm the most formal person. And one thing I really liked about Maven and my co-founders at Maven were that we weren't overly obsessed with an air of formality or, you know, being more, more serious for the sake of it being more corporate, for the sake of it, or acting like a bigger company than we really were.

And I really like that. I think it allowed us to be more of ourselves and care about the quality of the ideas that we were sharing. And a big part of our ethos in the company was everyone should speak up and we should be able to back up our ideas no matter who we are. So if you're a co-founder, you need to back up your ideas too.

If you're the most junior person. You need to back up your ideas. And, uh, yeah, I think that that ethos was really pervasive and in the past I would've thought, you know, well, you know, we need to be serious. I need to be more buttoned up. And when I kind of relaxed that rule, realized it wasn't actually a rule that you can inspire people, you can be a leader that people wanna follow without necessarily being super formal.

I think that's, that's one example. 

Brett: And so when you kind of think about this topic of authenticity, why do you think that it is so important? Like, what is it about being authentic? I mean, people talk about that all the time, you know, be authentic. 

Wes: Yeah. I think that, I'm not a huge fan of the word authentic.

I think that it gets thrown around a lot, and I think that we are sometimes different versions of ourselves in different settings, in different contexts with different people. And so this idea of, you are being authentic or you're not, or there's like one true way to be authentic or one true way that you are, I don't know if I believe that. Um, I think that it can be very helpful as a founder to know what makes you spiky and know your idiosyncrasies, uh, I have a, a concept that I call personality message fit. And it's this idea that, you know, sometimes you'll see a coworker say something, and just think, wow, I, I could never get away with saying that, you know, I used to think that about my co-founder.

He would say certain things and people would love it. And I would just know that if I said something similar, it wouldn't land in the same way and vice versa. So there are things that I could say that if he said would feel off or cringe or, or whatever. And so I think a lot about, about this concept of personality message fit as a way for us as founders to understand our baseline.

What is our baseline style? Where do our heads naturally go? Uh, what's our natural reaction to things? I think it's so important to know your baseline and then if you want to adjust it in, you know, to move a little bit to the right, to move a little bit to left on whatever spectrum you know you wanna be on, you can do that, but knowing your baseline, uh, I think is so important. And I'll give an example. Some people are very low emoting. So I have a client who, if he's happy, you can barely tell if he's upset, you can also barely tell. And the solution for this person is not, you should learn to really emote, like you should be more energetic or you should, you know, show your expression on your face more.

I don't think that we as founders or leaders can change 180, like even if we want it to. So it's better to know here is how I am, and then this is basically a constraint. So if you are someone who's low emoting, um, instead of trying to be, you know, high emoting, you should basically take that into account and turn up the enthusiasm in your words, in the actual content of your words, instead of relying on your facial expressions or tone of voice to do heavy lifting because you, you're basically like a zero on that criteria, which means that if you want people to know how you feel, you need to amp it up on other levers.

So that's an example of understanding yourself and understanding if the outcome I want is for people to better understand and read me, then knowing the levers that you actually have to pull can be really useful. 

Brett: So how does somebody figure out what their baseline is? 

Wes: Like many things, I think it's using your powers of observation and honing your sense of self-awareness.

It's not a shortcut, you know, silver bullet type of answer. And your mileage may vary because some people are more perceptive. They are better at noticing the reactions of others and whether, Hey, I just said this and I noticed you reacted in that way. Was that the reaction I was hoping for? If I say this or if I approach it this way, am I gonna get the reaction I'm looking for more?

You know, so I really take an experimental, iterative approach and it's very much first principles based. Am I getting more of the reaction I wanna get, basically is the main question. And then I'm gonna try a bunch of different things along the way to see, does that get me closer to that? Does that feel natural for me or does that feel off?

Does it feel off because it's a new behavior and a new habit? Or does it feel off because there's something that I don't really believe about what I'm saying. So I think you have to get reps basically. You know, this is not something where you can pontificate in your own mind endlessly and then come to a breakthrough.

I think you need to get out there, you need to be willing to try and then to be honest about the reaction that you are getting and be honest about what you could do to get closer to getting the reaction you wanna get. 

Brett: Could you quickly kind of get into this sort of interesting question, which is basically like, in what way should you change or in what way should you improve?

If we're talking about communication or persuasion or influence? And I think it makes sense, like we've all seen somebody trying to present, pretending to be Steve Jobs that's not right and how bad that is, or, um, trying to be Mark Benioff who is like uniquely classically, sort of charismatic. And at the same time, obviously there's a lot of things you can evolve and grow and get better sort of in the way that you communicate, influence, et cetera.

In your mind, is it sort of testing different things that leverage kind of the unique parts of you and ultimately the North Star as are you getting the thing that you want or the reaction that you want in people? 

Wes: Yeah, I think testing different things and also getting feedback from others, so both explicit feedback and implicit feedback.

I think that most people. Over index on explicit feedback. So we wait until, you know, our colleague complains about something or you know, gives us very direct feedback before we're like, oh, okay, this was bothering them. Whereas if you took a step back and noticed more, you would probably notice that this thing was bothering that person long before they spoke up about it.

So I'm a big fan of looking for implicit feedback as well as whatever someone is is explicitly saying. And uh, yeah, I think, I think going out and trying is the way to see what feels natural for you and what is resonating with your recipients, with your audiences. You can't know that until you go out and try.

Uh, and I would say that trying in a lower stakes way is better than trying in a very high stakes way. So before you try to present like Mark Benioff or Steve Jobs in a, in a high stake setting, try presenting that way with some of your coworkers behind the scenes. And if you can tell that it's not really working, it's kind of cringe or you're getting that feedback, then that's a sign that, hey, maybe I switch things up.

Maybe I try something different. 

Brett: Do you think most people can get quite good at actually understanding how what they're doing is landing with other people or reading sort of people's reactions? I think there are people who are innately better at "reading the room". There are a lot of people who tend to be like, struggle with actually understanding what other people are feeling or thinking about the thing that they are doing, and so do you think that's like a muscle that most people can sort of get better at?

Wes: I totally agree that there are some people who are naturally better at this, who are naturally more attuned to reading situations, reading people. I do think that this is a skill that you can get better at. I think from far away a lot of things look like magic, but if you come closer and you dissect what is actually happening, uh, a lot of things can be broken down into component parts.

And so, you know, I've personally seen clients really improve in this area. I teach part of this in my course as well, where, you know, students will come in and they'll, uh, report being shocked and horrified that an executive that they were presenting to was skeptical about something. And upon just a little bit of further digging, I realized that they didn't present their idea very well at all.

The reason why their audience was confused or skeptical, or there was a lot of friction or apathy was because they explained their idea extremely poorly. That when they explained it to me, I was also confused. I also was like, what, where are we going with this? This is confusing. Why are we talking about this?

And so, you know, it helps to, to get that feedback from someone. Because sometimes in our own minds we make a lot of sense. Outside of our own heads, other people lack the context or tacit knowledge that that we have that we don't even know that we have. So I often find that there is so much room for improvement before you reach the edges of, wow, it's really hard to read the situation or read that situation usually upon a really quick glance, I'm like, yeah, like you jump straight into nitty gritty details. Started talking a really chronological way of what happened starting from the past three months up until now. And that is confusing for someone who is hearing about this for the first time.

Right. And what you could have done instead was frame the topic up front to say, we are here to talk about the new feature that we're launching for X. The last time we talked about it, we had said that this product flow was confusing and so I took a stab at rewriting some microcopy working with the UX team, and I wanna show the new flow to you.

And what I'm looking for is your feedback about whether you think this is clear and if so, we're gonna launch this next week. If you, if they had said something like that versus jumping straight into, you know, the deep end, their audience would've understood more clearly what they were trying to say.

Right? So I think that there's so much that we can do to communicate more clearly, to be clear about what our own main point is, and then to frame that up to make it easy for our audiences to receive. 

Brett: Why do you think there often is so much lack of clarity and communication?

Wes: I think as founders and as operators, there's so much going on on a daily and weekly basis.

We are often back to back jumping from one meeting into the next and then answering slack messages in between. I think that people just don't put enough thought into their communication. One big takeaway that students of my course have is even by spending a couple moments, literally 15 to 30 seconds, getting grounded on what am I really trying to say?

What does this person need to know? What is my main point and what's potentially secondary? Spending a couple moments asking yourself these questions allows you to write a message that is much clearer and allows you to speak up on a call, in a meeting in a way that gets your main point across much better.

So I think that the, the biggest bottleneck to clear communication to being concise is lack of preparation. And I don't mean that you have to prepare for hours for every call, for every meeting, for every Slack message you're writing. Even a couple moments can make a really big difference, because if you are not clear in your own mind about what you are trying to say, of course when you say it out loud, it's going to be confusing.

Of course, it's gonna feel meandering because when you're there in real time speaking, you're actually asking your brain to do a bunch of different processes. You are taking in information in that real time setting. You're processing it, you're thinking about it. You're connecting it to previous information that you have, and then trying to formulate a response and then execute, say that response out loud.

All in the span of milliseconds, which is asking your brain to do a lot. So in my experience, this is a very unglamorous solution, but preparation is the most surefire way to be clear. Whether you are communicating in writing or in a meeting. 

Brett: Sort of in a similar vein, what are the things in this sort of broad bucket of communicating more effectively or clearly, what are the things that you end up talking the most about with people that are sort of seeking you out on these topics or the few frameworks or perspectives that kind of tend to have the biggest impact on the folks that you're working with?

Wes: I think one of the biggest ones is starting with your ideal outcome in mind. So instead of sharing what comes to mind in an ad hoc way, especially for high stakes or important conversation, thinking about: what is the end goal? What is my ideal outcome? And then working backwards from there to where am I now?

Given my situation, who's my recipient? Who are other potential stakeholders involved? What are the levers that I have that I could potentially pull that I have access to? What are any sensitivities that I need to be mindful of given the situation? And then, and only then thinking about what should I say? Starting with point B, which is where I wanna end up coming back to point A with where I am.

And then what you say is how you get from point A to point B, but that's really all it means to an end. And so I find that breaking down a situation and having a very goal oriented approach is a useful way to clarify what might I wanna do, what might I wanna say in a way that is more focused so often with my executive coaching clients, we'll do that.

So we'll start with what is the outcome that you want from the other person? And I'll give an example. One of my coaching clients is, uh, Head of Finance at a Series A company and he wanted to convince his founder CEO to adopt a more standard way of measuring CAC. 'cause the way that they were doing it was, was not standard.

And my client, head of finance thought that this would cause issues down the line. So the CEO was, was pretty resistant over a couple months. And Head of Finance said, my ideal outcome is I want the CEO to hear me. I want to be heard. I've tried talking about this to him, you know, for so long now I, I want him to hear me.

And I said, that is not a good ideal outcome. The ideal outcome is your CEO agrees to calculate CAC in this way. The way that you suggest that is actually your ideal outcome. Whether you feel heard or not, is a means to an end. That is kind of a nice to have, but that's not really the actual outcome. So even figuring out what is the end result that I want takes some judgment. And then of course, working backwards into, you know, where are we now? How do we get there? What is most likely to appeal to this person based on what you know about their worldviews, uh, things that bother them. You know, especially a lot of my clients are startup executives that report to a founder, CEO, and founder CEOs are idiosyncratic creatures. You know, they are who they are and you are not gonna get very far in my experience, trying to change who they are or trying to force them into entering your world. It's much better to frame whatever it is you wanna talk to 'em about, or your recommendation under an existing umbrella of what they already care about of values they already have, of ways that they already think the business should be run.

And so in my experience, being strategic about your communication is much more likely to get you more of what you want than being more ad hoc about it. 

Brett: What else could you share about that dynamic of communicating specifically executives with founders and sort of that specific dynamic? Is there anything else you've noticed in the most productive ways to communicate or things that tend to get in the way in that specific sort of set of relationships?

Wes: I think most founders have a pretty strong point of view about the way that things should be, and they tend to be more obsessive than executives in my experience. I think this is a good thing. I think that you want founders who have a strong point of view, who are obsessed about whatever they're obsessed about.

I think something that can get in the way is when executives are expecting the founder to be less spiky, to be more balanced or more reasonable, I would say. I think that many pairings of execs and founders that work really well are when execs recognize that their founder can be spiky in different ways that might not really make sense that they are really good at certain things and not as good as at other things.

And instead of expecting your founder to get better at those things, I think as an executive, you'll get further if you assume that their, your founder's personality is a constraint. That is a constraint. And if you are especially reporting to a startup, CEO, I think you need to be okay with the founder's personality as it is.

In my course, I get a lot of questions from folks who essentially ask how to better handle their managers, including startup CEOs. But the question behind the question, the underlying question is basically, how can I change this person? How can I make them more of the leader that I want them to be? And you as an individual likely don't have the leverage to do that.

You are battling years of this person being this way, having reached success, being the way that they are. And so it's kind of a losing battle to try to change that person. It is much better to assume that that person is the way that they are. You are not gonna be able to change them. And so asking yourself, can you live with that?

Can you be happy and thrive in an environment where you have to work closely with this person? Uh, and second question is, what can I do to make this working relationship better? So instead of assuming that the CEO or the the founder will change to make your relationship better, if anyone is changing, it's, it's you as the executive.

You have to ask yourself, how can I better mold myself to work better with this person? And I have an exercise in my course about getting in the head of your manager. And one really funny, interesting insight that comes out of this when we review the exercise responses, some people, you know, a lot of people will say, yeah, like I, I know my, my manager wants more of X, Y, Z for me, or wishes I were more this way. And I keep hoping that they won't want that anymore, but it's been two years supporting this person and every single time they wish I would bring more data or every time they get skeptical in these areas. And so like, clearly there are patterns, right?

These are both probably implicit and explicit clues that we are getting about what our manager or CEO or founder wants from us. And yet we dilute ourselves thinking maybe they'll change, maybe they won't want this from me anymore. And that's, that's not really a winning proposition. It's much better to acknowledge that and then decide, you know, how do I wanna adjust my behavior?

Brett: Is it just that the executive or manager is, is in a place of power, which means that they should not change, but the person underneath them should? Like, there is a little bit of irony in that. Like this is the sort of immovable object and I'm the one that that, sort of has to, You know, contour around that. 

Wes: Yeah, I think that's the reality of the situation.

I think acknowledging things as they are is useful because you don't end up spinning and wasting cycles and emotional labor trying to change something that you can't really change. And power dynamics are one of those things. So especially if, if you are the exec reporting to the CEO, to the founder, then yeah, I think that that acknowledging that power dynamic is very useful.

On the other side, I think if you are the founder in this situation, it is also useful to be self-aware of the ways that you might be impacting the people that you're working with. And if you are consistently getting feedback that you know, a certain part of your behavior is not productive, then it's up to you to decide, do I wanna continue that and suffer the consequences?

Can I live with the consequences or is that something that I might want to change? Knowing that being the person in power, you know, by the time anyone's speaking up to challenge you or to give you feedback, this has probably been bothering them for longer than you knew. And so I think on the founder side, it's not, I think it's, it's treating that power dynamic with the respect that it deserves, knowing that, hey, I'm the one in, in power here.

I know that you are probably going to mold yourself to fit me, but that doesn't mean that I should act in ways that are potentially destructive or unproductive. Like I also wanna make sure that I am making this a good relationship. And when both parties try, but don't expect anything from the other person, I find that that ends up creating a, a solid relationship.

Brett: How do you think about the adjacent topic, which is basically, in what way should people change, right? And you know, if you're the person you're reporting to wants more quantitative rigor, but you're a much more intuitive person. Maybe to be successful in this specific role, you need to be more quantitative.

But maybe to sort of get the most out of yourself you need to find another environment that actually values the intuitive nature that you have, or whatever it might be. There's this great book from decades and decades ago called The Effective Executive that a lot of people haven't read, but it's this famous book from Drucker.

And like one of the basic points is that companies generally focus on weaknesses of individuals and improving weaknesses instead of trying to get an incredible understanding of what people are actually insanely good at. And just like pushing entirely into those things.

And I would say like in general, if you think about like traditional performance management, it is, here's the three things you can do better. Go work on those things. And I'm interested in sort of what you've noticed either in the context of founders or executives, sort of how to reason or work through like what are the gaps you actually should close. 

Wes: I am a huge proponent of leaning more into your strengths, if only because there's usually only so much that you can do to address something that is not strong for you, and so it's much more highly leveraged to dive deeper into your strengths if possible.

I think the challenge with that on the ground floor is that especially with founders, you are often the best person or the most available person to do something, so you don't always get to only focus on your strengths. There are many times when. You need to operate out of your core zone of genius. And so I think ideally, yes, like ideally focusing on, um, the parts that come naturally for you and choosing roles that allow you to leverage your strengths and being able to leverage your strengths maybe 80% of the time, in your role, whether as founder or operator. If you find yourself having that ratio flipped, where 20% of the time you're using your strengths, 80% of the time you're, you know, kind of feeling like you're flailing, kind of feeling like you're, you're doing stuff that you're not very good at, not very naturally suited for.

I think that's where a role change could make sense. And I think it, it's actually a lifelong practice, an endeavor to get ever closer at understanding what are you very good at and comes naturally for you, and where is their market demand? After every role in my career, I've reflected on this, and I think I've, I've gone ever closer to a setup where I am using my natural strengths.

But I, I do think it's something that you need to actively reflect on because it's so easy to get pulled in, you know, a bunch of different directions, and you might look up one day and realize that you're working on a bunch of stuff that you don't find very fun and you're not very good at it. That's just not as enjoyable of a way, I think, to go through your career.

Brett: So what, what did that look like for you when you think about your own arc of your career and like the first couple things that you've done and now the last couple things that you've done, like how has it become more aligned with sort of that set of ideas you were talking about? 

Wes: Yeah, so I'll give an example where I worked on this skill, uh, or on this weakness I would say, until it was not a blocker for me, but then intentionally started choosing roles where this was not a core need.

So I used to be pretty disorganized and bad about operational details. And early in my career, this was pretty prohibitive for me because I was, uh, in a brand management role and had to manage multiple launches for multiple SKUs with different, uh, launch timelines, production timelines, et cetera. It was a physical product and it was really overwhelming, keeping track of all of it.

I dropped a ton of balls and I realized that. If I am to advance to the next level where, you know, as a manager, I might not have to manage all the details myself anymore, I'm never gonna get there because I'm never gonna get promoted if I'm so bad at managing all these different details. And so I put concerted effort into learning to become more organized, to become better at project management, to a point where, I could keep track of different projects and where they were and could communicate upwards and keep the appropriate parties aware of what was happening. But I knew that this was never going to be a strength of mine. That to this day, logistical details very much stressed me out. I tried to outsource it as much as possible.

I still dread doing things that, that require a lot of logistical detail, especially ones that have a high downside if you get any detail wrong. And so one, I realized that brand management was not for me. So I literally changed career paths after that role. But I also learned a lot about myself from that and realized that choosing roles that had more ideation, that had, uh, thinking about shaping something from the ground up, how to sell it, go to market, like those were things I liked about brand management.

And so for my next role, I looked for more of that. And so with every role, it was like, okay, here are the parts that I dreaded, that I could brute force my way through, but were not very enjoyable. And then here were parts that came very naturally to me that I kind of lost track of time doing it or, you know, wish my more of my role were doing this aspect, what org might need this?

What type of role might need this? And how do I position myself for, for that? 

Brett: After you sort of had that role, do you sort of sit down and open a notebook and sort of collect your thoughts in that way to try to figure out what to do next? Or is it more organic in your, in terms of the way that you've gone about doing it?

Wes: It's probably a mix of both. I think writing out what I'm thinking and writing about my problems, often by the end of writing it out, I come to a solution for myself, which is fantastic. So I'm a big proponent of, I don't know if you wanna call it journaling per se, it's more like problem solving through stream of conscious writing.

I do a lot of reflection that way. The other aspect that is a bit more organic is more driven from, I guess, strong feelings in either way, strongly disliking something and wanting to avoid it and just realizing that and then strong feelings in another direction of, oh, like I really liked working on this part of the project, or, I really like working with this type of client.

I look forward to working with this type of client. The hour went by so quickly and we had, I had so much to say for this type of problem. Whereas with other clients, sometimes I have a bit less to say, like, it still feels helpful for that person and they tell me it's helpful, but I feel less on point. I feel less on fire, you know?

So I think it's checking in with yourself on how did that feel? So that is a bit more intuitive, but I see those as clues that our bodies are, are trying to tell us about what was exciting and what was not. 

Brett: And having the chance to work with lots of people in a variety of different rows over a long period of time, i'm often struck how few people are introspective about this topic of like, what am I purpose built to do and how well fit is that to the job that I'm doing? And maybe there's some sort of cognitive bias that oftentimes when somebody starts down a path, they just, there's kind of like the status quo bias, like, I'm gonna keep doing that thing.

You have somebody that's in marketing and they generally just want to keep perpetuating, well, I started out as a junior marketing manager, and then I want to be a marketing manager and on and on and on. And oftentimes I've just, it feels like, and maybe I'm wrong in some of these situations, but like when you're observing the person, you're kind of saying, I just think they're doing the wrong thing.

But it's interesting how infrequent it feels like there's kind of that type of reflection and then sort of a meaningful change where somebody recognizes that this thing isn't shaped correctly for me. One of the things that I've reflected on is it feels like one of the most valuable things for society, would be to better match people with the thing that they're doing. You know, you find, you take a job that you or me might find really difficult and unpleasant to do some sort of, I don't know, obscure accounting role. And yet you find somebody who's really lights up and is purpose built for that and you watch them doing that thing and it's this extraordinary thing when you see sort of that type of matching.

But I've often wondered, and, and maybe there needs to be just more directness at work where other people are, are trying to explain that maybe they're built for something else and they should reflect on that. I don't know. I see most people like what they start to do, they just kind of keep doing. 

Wes: Yeah, I think whatever default status quo you're facing, you know, I'm in marketing, so I continue to be in marketing.

I think that ends up being what most people do, probably partially due to sunk costs. Like I've already invested x number of years in this field. If I change fields, I have to start over. That sucks. There might also be an element of golden handcuffs too, with not wanting to start over or not wanting to, to take a pay cut or, you know, a lower title, whatever.

But, uh, I love what you mentioned about there are accountants out there that love the kinds of things that you and I would hate doing, and I think it's such a great reminder that whatever it is you find extremely difficult and unnatural for you. There is someone out there who loves doing that, and it comes extremely naturally for them.

So if you are in a role that requires you to do this thing that you are not very good at and could not see yourself getting much better at, in some ways you're competing with someone. Who naturally is good at this thing and enjoys it, and who is going to win in the long term? The person who, where this comes very naturally for them, or you struggling barely, you know, making things work, where five units of input of effort result in one unit of output.

Whereas that person who, you know, where this comes naturally to them, it's one unit of input, five units of output. When I think about that, I think that the deck is stacked not in my favor. If I choose to work on something that is not a natural strength of mine, that there's just no way that I could potentially win or succeed and my day-to-day wouldn't be very fun either in if I'm working on something that, that I'm not very good at. So from a very practical, you know, pragmatic perspective, I think that each of us needs to be more introspective on this because most things take longer than you think. Most things are harder than you think, especially if you're building something new and you need the deck stacked in your favor as much as possible.

I always say, you know, to to folks who pitch me with, with their startup ideas that what is your unfair advantage doing this? If a random person, the next person who walks down the street could have an equal likelihood of making this work, I think you're probably working on the wrong thing. And that unfair advantage doesn't need to be years of prior industry experience.

It can be a weird obsession with this problem. Like you've never worked in retail, but you are super curious about it and you've always been obsessed about it. Awesome. There's plenty of people who founders have started companies in, in industries they, they had no experience in who are succeeding. So there needs to be something though, and I consider obsession an unfair advantage as well.

But that there's interest there, right? You wanna be thinking about it, you wanna be working on it, you are curious about it. You know, it's, it's where your head is naturally going, like working with not against who you are and what you're naturally good at. I think it's something we could, we could do more.

And I personally spent years working against that. And I think also earlier in your career you have more energy and you are able to brute force your way through things. And as I've gotten older, I've realized that it is increasingly harder to get myself to do shit that I don't wanna do. Before I used to be able to just power through and I'd make it work.

And so from, again, from a practical perspective, when I think about the next, you know, couple decades of my career, like if I am increasingly finding it harder to, to get myself to do things that don't come naturally to me, then looking ahead, like I need to make sure I'm doing something that comes easily to me and make sure that there's market demand for it and it's providing value to others, et cetera.

So I think, you know, early on in your career, most of us start by brute forcing, you know, because we don't have a lot of skills, we don't have a lot of experience, and then we forget midway through our career that maybe we shouldn't just brute force things anymore. And that there is a difference between good struggle and bad struggle.

And I think that especially for high performers, ambitious people, we're so used to reframing difficulty as opportunity, right? It's the whole like, oh, it's not anxiety, it's excitement, right? We're very good at reframing these things in order to climb bigger mountains, climb the next mountain, et cetera.

But I think at a certain point in your career, being able to distinguish bad struggle, as in, you know, I find this really hard. I don't ever see it getting easier. Like I would say that that's not really productive versus like, oh, this is in, in an area that I like working in. This is a hard problem. I don't know the answer yet, but I'm excited to work on it, and I can see myself finding a solution that is a different kind of struggle that is much more productive.

So I've gotten much more attuned at differentiating between bad struggle and good struggle. 

Brett: Is there anything else sort of in the theme that we're talking about that you, you tend to sort of tell folks that are sort of seeking your advice or thinking about, do I wanna change roles or change directions or, you know, you've been doing marketing for five years and as we were talking about a second ago, for most people in the next five years you're gonna be doing marketing and there's often not a lot of introspection. 

Wes: I think doing an audit and taking stock of the parts of your role that really light you up and the parts of your role that you have to summon internal fortitude to really get through.

I think doing that reflection is helpful because as we go through our time, you know, within a certain organization things often change pretty quickly without us realizing it. And so your role might have started being very much aligned with what your strengths are, but over time, due to changes external to you, your role might now be only, you know, a small fraction is what you actually like doing.

And so, you know, looking up once in a while from the day to day to take stock, I find that to be helpful. 

Brett: Do you advise people to take stock in any specific way? 

Wes: The way that I would recommend is to pay attention to what gives you energy versus what feels like it is depleting energy or something that you dread.

So it might be, I wonder if, you know, I don't know if paying attention to your emotions is necessarily the right way to put it, but paying attention to your excitement level and energy level, I would say. And then the, the other aspect of that is thinking about what would make you not feel resentful. I think that a lot of times we continue on because we're continuing on, and you know, if there's not a big payout at the end of that, or if there's not a promotion or, you know, some reward, I've found myself in the past looking back on, you know, wherever I worked on and thinking, just feeling a bit resentful about the time spent there or like what I did, you know?

And I don't think that that's productive for anyone. And so I like making sure that the journey is as worth it and as enjoyable as whatever destination. Because especially with startups, I see a lot of operators picking a company because, you know, they're betting on that company and you should do that.

But like, chances are, the bet is not necessarily gonna pay out with, uh, a really big payday. And you don't wanna look back and feel resentful about that, right? You wanna look back and be like, I learned a ton and I did a bunch of things that I wouldn't have gotten to do and I built a bunch of cool stuff and I'm a different, sharper, better leader now and operator now than I was before, you know, even without whatever, you know, golden payout.

And so I think as you think ahead to, you know, do I want to commit to another X number of years here or double down on this path, thinking about avoiding resentment is another good thought experiment. 

Brett: One of the things that you've written a decent amount about is sort of the topic of being more strategic or communicating in a more strategic way.

I, I'm interested when, when someone gets the feedback, you need to be more strategic, which I think is a very common thing that is given to all sorts of people. What's sort of the coaching that you tend to do with somebody, let's say they came to you and said, oh, my manager said I'm not strategic enough.

What should I do? 

Wes: The first thing that I would suggest if you hear you're not being strategic enough, is to get more clarity about what your manager actually means. I think that all of us have either had a manager over the years tell us, I would like you to be more strategic, or we have been that manager who has told someone, I want you to be more strategic. So we throw this advice, or this recommendation or feedback around so casually without really, I think on the manager side, getting more specific about what does that actually look like for you in your role in this context, what does not strategic look like or less strategic, and then what would more strategic look like across a couple different dimensions of the things that you work on. And so I think that the worst thing that you can do is if, if you hear that feedback is start making a bunch of changes, thinking like, now I'm being more strategic. And then you check in with your manager three months from now and you're like, so manager, what do you think?

You know, I've, I've made all these changes. And usually the response you're gonna hear is, wait, what? Like I, first I didn't notice, and secondly, that wasn't actually what I meant. Like, I'm glad you're doing those things and that's awesome, but it didn't actually solve the core problem that I was, that I was actually trying to get you to work on.

So, you know, I've learned this the hard way. I now teach this in my course that if you hear vague behavioral feedback, like be more strategic. Other examples are improve your executive presence, manage up more, be more data-driven. These are all very common things. Think more strategically, right? These are all very common things that we might hear, and it's a good idea to get more context.

And your manager might not be able to share more specifics if you just ask them point blank. So you may need to ask indirectly and draw that information out of them. So, you know, for example, when I did this thing, like, would you say that that was strategic or did it not feel as strategic? Or, what are examples of my peers, you know, other product managers or other marketers that you feel like are strategic, right?

So if you get some examples, you can then read between the lines and realize, oh, that person always does this. I've noticed, you know, the couple people that this my manager mentioned tend to do this, right? So you kind of read between the lines to put together what is, what does being strategic really mean, and then run it by your manager to say, A couple patterns I've noticed are this, like, if I start to do that, would that be valuable?

Would that, you know, feel more strategic? And it's much easier for most leaders to react to something you're putting in front of them to correct you basically to say yes, that, no, not that than it is to say, you know, teach me ways to be strategic or define what that means for me. Um, your leader hasn't done that thinking like, they've gathered from all of your interactions with you that you are not strategic and they're now sharing that with you. And I think it's our job as operators to then unpack it and clarify and get to that next level of specificity so that we can fix the right things. 

Brett: Do you think in your experience when a manager gives feedback like that about being more strategic, that there's a few things they're generally trying to communicate?

Or is it truly like a long tail, it could be 60 different things that that manager is trying to communicate? 

Wes: It's probably a few things for the individual that they're giving that feedback to. So the problem is, if you are the operator hearing that, you're not sure what those things are, but for the manager saying it, yeah, I do think that it's a couple situations that have shown that manager that, hey, this person could be thinking more strategically. And so a couple examples of, of what it could be, you know, I see operators sometimes be too zoomed in to the project or the, the task in front of them without considering organizational context.

So that could be an example of you're not really thinking strategically. You're, you're focusing on the how of getting this exact thing done, but you're not thinking about how does this stack rank amongst other things that we're doing. How does this impact other things or how is it impacted by other things?

So that's one way of, you know, what be strategic could mean. Another could be thinking more about what, like choosing what to do versus just the how. If you are used to something being fairly scoped and defined by the time it arrives at your desk, you are thinking about, well, how do I get this done? How do I bring this to fruition?

Whereas the next level that your manager might be looking for is you doing the shaping. You saying We should do this, not that, and here's why, and here are the trade-offs and here are the risks involved. And choosing what to prioritize and doing that shaping. So that's another idea of what be more strategic could look like.

And so yeah, for the operator it's, I think it's, you know, you need to be the one to figure out, okay, what does my manager meet here? 

Brett: Yeah. I've noticed a lot of times it also feels like, to your point about maybe just focusing on low level tactics or some project in isolation versus figuring out how everything is constantly connecting to what needs to happen in the business, I think is like another form of that.

The ability to sort of understand the business and then translate that into this thing over here. Then break that thing down into sort of the actual things that sort of ultimately need to happen. I think it's very easy in companies and startups to just get lost and not focused on things that actually matter.

Like what are we trying to do in the business? Why are we trying to do those things? What are all the different levers we have to pull? And then like, is this thing over here that I'm doing, does it ultimately matter to the business? Like that tying back to sort of things, multiple rungs above you, I think is often sort of a, a gap that I've noticed.

Wes: I think another gap that I've seen is stack ranking and prioritizing which problems are actually worth solving. And so, you know, junior operators will come up with different ideas and it's not necessarily a bad idea, right? Because most of the time, if it's, if it's obviously a good idea. Done. We're gonna do it.

Awesome. If it's obviously a bad idea, you probably wouldn't have brought it up. And so most ideas are in this gray area, middle ground of like, yeah, like that's a problem and this would solve that problem. But the next level of thinking strategically is, is this a problem worth solving? Because a business is pretty much a bunch of problems all the time, and when you solve some of those problems, you have a new set of problems.

And so you're just constantly dealing with problems. And just because something is a problem doesn't mean it warrants resources to solve or the resources that you are asking for to solve. And so, you know, developing that sense of right sizing of context of, you know, is the juice worth the squeeze here to try to solve this? Are we gonna get enough upside if we improve this or is this a problem that we live with? You know, it's a little fire that we're gonna let burn because working on these other problems are more important. And so it's, I find that it's, it's rarely like, this was a bad idea or this is not a problem.

It's more like, this is a decent idea and yes, this is a problem, but it's not hairy enough to warrant taking action on, or the upside isn't big enough to invest, you know, all this effort in building out this program or building out this campaign or whatever else. And I find that with junior people that that can be harder to learn.

Brett: So I wanted to switch gears a little bit. A while ago you worked on creating what is called the altMBA with Seth Godin, who seems like a very interesting human in general and, I thought it would be interesting just to hear more about that specific effort that you started and like what, what were some of the interesting things that you took away from that?

Wes: Yeah, so Seth and I started the altMBA together. 

Brett: How did you meet Seth? 

Wes: He put out a job posting on his blog, and I did not know him before and was vaguely familiar with this work as a marketer. You know, I knew he was a, a famous author and he wrote a blog post saying that he was looking for a special projects lead.

And I was in San Francisco at the time. I grew up in the Bay Area and was looking to move to New York and was like, okay, I'm gonna apply for this if I get it. Awesome. It was a six month, uh, stint and then I can find a full-time thing in New York afterwards. And so that, that six months ended up turning into three years.

Brett: What was in your application? Like how did you get his attention? 

Wes: I'm reaching back into memory lane now, 'cause this was, this was 2014, so 11 years ago. So the application, there was a written portion with like short answer questions and then there was a video component. I actually borrowed for hiring at Maven because I found it to be so useful.

Um, but the video was, you know, film a, a two to three minute video talking about what you wanna build, what you wanna learn, and what your strengths are, something like that. And I did my video in one take because I thought like, there's no way I'm gonna get this. Like a lot of people wanna work at Seth Godin.

What are the chances that, that I'm gonna make it through? So you don't wanna be too emotionally invested in, you know, creating this perfect application, doing 50 takes, and then not getting it. So I didn't, one take, I thought this is good enough. I sent it off and the next day I see Seth in my inbox and he's like, Hey, I liked your application. I think you could, you know, be a good fit. Do you wanna hop on a call? Uh, so we did a Skype call because Skype was a thing back then. Zoom wasn't even around. And 

Brett: Skype is literally last week as being sunset. I know, I know 

Wes: know. Yeah. Yeah. 

Brett: Nice connection there. 

Wes: Yeah. Um, so we did a Skype call and then we did an in-person interview because he, he's normally based in Westchester, New York, but was gonna be in California for an event, for a speaking event in the Bay Area.

So we met up, did an interview there, and then I got the role. 

Brett: And so how did that role translate to what ultimately became the altMBA? 

Wes: The first six months were special projects lead type work. And so a big part of that was, you know, Seth was closing down the last company he's working on, he'd worked on it for eight years and was looking for what to do next. And so I did a lot of research on potential businesses he could start, interesting projects, books he could write, teaching that he could do. So it was a lot of bouncing ideas. We had this giant magnetic board with a hundred colored index cards with magnets, just like a bunch of different ideas.

And towards the tail end of that, we coalesced around learning and teaching. Seth's been a teacher for, you know, decades by that point. And his audience got a lot from learning directly from him. And at that time we also were seeing that massive open online courses, MOOCs prerecorded courses with videos were the dominant form of learning, but they weren't engaging.

And you know, as I started digging into it, uh, by the way I was digging into it because one of my other projects at the time was creating Seth's Udemy course, which became a bestselling course. And you have the top selling one that year. And so, as I'm thinking of ideas for Seth to do, plus working on this, this course.

I started digging into the completion rates of video courses and realized that they were abysmally low. I think three to 6% is completion rate. And there just seemed to be a huge gap from people learning asynchronously and all the work we were putting into making this Udemy course great. And the fact that three to 6% of people were actually gonna finish it, it felt like this couldn't be the pinnacle of the internet connecting us and like bringing access to different experts like Seth.

And so we thought, you know, was there a way that we can flip the script on this? Especially because Seth at that time was, was still doing a lot of speaking gigs and it was expensive to see Seth in person. So, you know, I, I also organized, you know, a couple in person events and it just seemed to be such a big gap between you, you know, you either learn watching videos and a tiny percentage won't finish, or, you know, you come see Seth in person and it's expensive. And also only a tiny percentage of people can afford flying to New York, so there must be some middle ground. And so that's when we started kicking around ideas that eventually led to launching and founding the altMBA. And so that's where, you know, at the end of that six months that said, sounds like we're both really excited about altMBA. Would you wanna stay and build it out, run it, grow it. And so that's, that's how we continued on. 

Brett: How did you actually get it off the ground? Like where did you start with the first group?

Wes: The first group I downloaded and scraped, um, Seth's email list and sorted based on at domains for email addresses to see which companies had the most Seth fans. So it was [email protected], at nike.com, at uh, Clorox, et cetera. And the idea there was how do we reach out to folks where there's a density in Seth fans in organizations that we want more students from.

And so part of the thinking there was, you know, Seth has a lot of readers who are freelancers, solopreneurs, business owners. But when you see students from brand names. That tends to be a bit more exciting for everyone, including the freelancers, seeing that, wow, there's people from Whole Foods taking the course.

There's, you know, a director from Kickstarter, et cetera. And so I wanted to create that excitement in the beginning by getting some of these more, uh, logoed names in the course. And so I sorted the email, looked people up on LinkedIn, thought this person seems friendly, this person seems like they, you know, they're curious, et cetera.

And they would reach out to reach out to specific people. So that first cohort, we were pretty deliberate about, about, you know, getting the right kind of people in to really set the culture and the ethos of the program to set the bar that we wanted to set. And then shortly after, I wanna say after maybe the second or third cohort is when I realized that relying on set's email list was not going to be sustainable for growth first because he didn't like spamming his email list, talking about the course. He has his blog, you know, it's mainly about ideas and then also because I wanted the opportunity to nurture leads over time, prospective students over time and, and the freedom to do that without always relying on, on needing to use Seth's blog. And so early on I started building an email list separately and we would drive folks who were interested, uh, into that email list.

And then, yeah, I think for that one I wrote, I wrote 50 email campaign for emails twice a week for months, where once someone joined, you would get dripped out content that would nurture you over time and then build out flows from there with, you know, once you applied for the altMBA, you would get kicked off that list into a different list.

It was a lot of hands-on building, a lot of nurturing and, and driving um, customer acquisition, student acquisition after the initial program was more set. 

Brett: For those that aren't familiar with Seth, how would you sort of describe him and what was it like? I mean, I, I followed him from a distance for a long time.

Many, many years ago. He spoke at a big conference that we put together. He's such a, a unique human. What, what is it like actually working day to day on something with him? 

Wes: It's hard to describe Seth in a few words because he is, he's such a unique creature and it was such a privilege to get to work with him so closely for three years, I learned so much, and I would say transformed as an operator, as a leader, as a builder. Um, from working so closely with him, what's he like on a day to day? He's even sharper in person than he is online. Which I think is impressive because, you know, sometimes I'll, I'll read people's writing or you know, watch them in videos and stuff and then, and then I'll meet them and I'm like, okay, like, you know, you're pretty, you're pretty sharp.

But like, right, Seth is like 10 times funnier, faster thinker in person. Like he's just even better in person, I would say, which I find impressive. He also has really high standards. He thinks incredibly quickly and so, you know, there were so many times where I had prepared an explanation to describe something.

I don't know, maybe it would've taken three to four minutes and he would get it in 30 seconds. You know, and I'd be like, oh, okay. You know, and I'd remember going home for the holidays one year and then coming back to the office and feeling like I had actually dulled in like the two weeks that I had taken off.

Because coming back to the office, I'd forgotten just how fast he thinks and how fast I needed to be to keep up. It was like a culture shock, like reintegrating, you know, back into the office kind of situation. He has incredibly high standards. You know, before I was at a, a Sequoia backed series C or D startup in SF before working with Seth.

And we talked about shipping quickly and iterating, and I thought I knew what shipping quickly looked like, but when I started working with Seth, I realized that it was child's play. That that was, that was not shipping quickly at all. And that, you know, our standards, my standards were low. He would have these standards that felt so unreasonable that it would like, it would be upsetting that they were so unreasonable, but then I would find a way to do it.

And so this happened over and over and it really taught me that. A, like your standards are probably too low, at least for some things, and that you can probably raise them and that, you know, trade-offs like speed versus quality. You know, like people talk about that and throw that around like, you probably have room, or I had room to be faster and to produce better quality without starting to trade off on either.

That in most situations there's so much slack that until you get to the fringes, yes, there's a trade off, but you are nowhere close to that. That by sharpening my craft and being more strategic, being a better operator, executing better, being ruthless about where I was hiding or avoiding doing work I didn't wanna do because it was uncertain or it was hard, or I was afraid to be wrong.

There are just so many ways that, that I sharpened my execution so that I was both faster and produced higher quality work. And so that, that like bar setting was probably the biggest thing that I took away from working with them. That, that I continue to think about a lot and continue to, to try to espouse.

Brett: When you talk about sort of having an unreasonably high bar, can you make that tangible? Like what, what's the story that comes to mind to really bring that to life? 

Wes: The story that comes to mind that I've shared on a couple other podcasts as well is that we were figuring out the book list that we wanted to send to ultimately students.

So, you know, a box of, you know, seven to nine books to pre-read before joining altMBA, I had created this list and was starting to, to vet some of the books. And so I ordered a bunch on Amazon and they arrived and I told Seth, okay, so I'm gonna read through these and it's gonna take a couple weeks, you know, I'm gonna try to go through a few a week, just, which felt fast already.

And he was like, you have two days. And at first I just thought, this is impossible. Like this is a huge list of books. There's no way I can do this in two days. But once he said that, I started to reframe the problem in my mind and realized that I could get it done in two days if I had to. And so like this reframing I think is, is something that, that when I am faced with a problem that feels impossible, I still now do that reframing like, how can I adjust the scope, for example, to make this work?

How can I think about the end goal, which is finding books that we can stand behind and I don't need to read the entire book page by page cover to cover to get a sense of whether this is a, a valuable book or whether it's kind of fluffy and not as relevant. And so shifting my mindset on that problem and changing how I was viewing that problem made a huge difference.

And that just happened multiple times a day. Every day there'd be something and I would think, okay, I'm gonna come up with something in the next day. And he'd be like, come up with something in the next hour. You know? And I would find a way to make it work, you know? And it wasn't like it needs to be exactly as good as it would've been if you had spent days on it.

But can we do a directional check-in? Can we kind of. Get faster, get to the core of the idea faster. Like oftentimes you can. And so I'm a really big fan of shortening the feedback loop as much as possible these days. And you know, a big part of it was, was learning that from Seth. 

Brett: Is that just the way that he intuitively behaves, that he is equally unreasonable for himself as he is for those around him?

Wes: Yes. Seth is one of the fastest sharpest thinkers I've ever met from near and far. So he has equally unreasonable standards for himself. He also is very good at his craft and has spent years honing his craft. And so he can get to the right answer quite quickly because he has so many reps. And so I think the meta lesson also from working with Seth is that if you wanna do things that seem unreasonable, the leverage needs to come from somewhere and getting sharper at your craft, at translating your intentions into reality, at translating your idea on paper into something that your customer or your audience, your reader feels you can improve on, on that, and you can improve on that by studying your craft. 

Brett: So how does that translate to like you today? How, how do you define what your craft is and what does it look like to try to hone it in the way that you just described?

Wes: I think one part of my craft is explaining ideas clearly and in a compelling way. And I see this play out in my newsletter, in social posts, in my course in coaching. A lot of it comes down to can I persuade this person to try this way? To see why this problem exists to consider whatever approach it is that I am suggesting might be better.

And so I think breaking down that craft even more is thinking about what objections might that person have, right? So my brain, immediately when I have an idea, I immediately think, is this really true? How might it not be true? In what situations is it true? And in what situations is it not true? And what questions might someone have if I said this?

How might someone misinterpret this? How might someone misapply this? And so I consider all of this the craft of explaining something well and explaining something clearly. So I think a lot about that. I also think a lot about persuasion and influence. So how can I get to the end goal that I'm looking for as quickly as possible?

What would be compelling for this person? What are both explicit and implicit things that I can play around with to create something that people wanna be part of. You know, I think as founders, that's very, very important too. I think part of your raft as a founder has to be selling your ideas and building hype.

Building hype, not necessarily like over-hyped crypto, you know, stuff like that. Like, but building hype as in getting people excited about the thing you are excited about. And that is not always simply saying, this is really exciting, right? Like that's a little bit too on the nose, it's a little bit direct, or this is groundbreaking, right?

It's a lot of telling, not a lot of showing. Whereas the craft of building hype often is creating this aura of this is something that is going places, this is something that other people like you are interested in. So. That might look like getting the right people participating in something, especially early on and then amplifying that.

Uh, it might be design choices that signal who this is for and you know, design that's modern and not cringe. Like it's all these subtle subconscious clues that often get people excited about things. And so I would say that that is very much craft and I think a lot about that as a builder. And yeah, so I think those are a couple examples of crafts that I think about.

Brett: Maybe sort of on that theme, what else might you be able to share in terms of people who are trying to build followership on the internet? You've done that in so many different forms. You've done it for yourself in the past handful of years. You did it for the altMBA and there's tons of examples in between there.

And I think you hinted on some of those things, but like for people that are trying to build followership around themselves or a thing that they're doing. What are some of the things, the highest leverage things that they should sort of keep in mind? 

Wes: From a founder perspective, keeping in mind how you can add value to your audience, I think is, is probably the biggest one.

So at Maven when I was building up, especially our supply side and appealing to instructors getting subject matter experts on our platforms, they could teach courses. A lot of my work was adding value to subject matter experts so that they were learning something new when they interacted with Maven, when they read our posts or my posts, that they were reading something that made them think differently, that help them solve a problem that they were working on.

You know? And so I would create content around that. I think that a lot of building in public content is sometimes too much about your customer versus to your customer. About your customer meaning, you know, here are revenue graphs of our growth and like, this is so exciting and that is interesting for customers, but I think the meat of what you're sharing should be valuable stuff that is showing your credibility, showing your expertise, showing how you can make your customer's life better.

Uh, and so for example, with Maven, I would share frameworks on how to turn your ideas into named claimed frameworks in IP. So how do you put a visual around it? Is it a pyramid of something? Is it concentric circles? Is it, you know, some kind of named framework that encapsulates your ideas, right? And so subject matter experts flocked to posts like this because this is something that they think about. Another was talking about how to engage audiences. If you are teaching on Zoom or lecturing on Zoom, it's very hard for audiences to stay focused for an hour or two hours on Zoom. And so I shared a concept I called the state change method about how every three to five minutes you should have a state change of some sort, whether that's switching from gallery view mode into slides, or vice versa. Asking people a question, telling them to put something in Zoom chat, having someone else speak for a little bit, whatever it might be. So this was also very valuable. By doing this over and over every month, you know, for years this allowed instructors to realize, wow, Maven really knows what they're talking about.

I'm not seeing useful ideas like this anywhere else. And if I am building a course, to package up my ideas, Maven is the one that I wanted. And so I, I really thought about it in terms of our instructors being kind of like baby ducklings. I talk about this kind of behind the scenes, uh, with my co-founders, that customers aren't always ready to buy when they first hear about us, and that's very normal.

We don't wanna force anyone to do it, to do anything they're not ready to do. It's very useful if we are showing up consistently with the right group of people that we believe are, will eventually become great instructors, and we can have them imprint on us. Like the first thing that you see, you know, the, the baby duckling sees it's it's mother, right?

And so it instructors are kind like baby ducklings and Maven is the first platform that they're interacting with as, you know, a source of an option for how to teach online. Then when they're ready months later, or even, you know, a year or so later, they're gonna come think of us first. And so how can you add value all along the way to establish yourself as a really strong, credible partner?

Brett: Do you find that when you're trying to build an audience or followership around a thing that almost all the same ideas always apply if you're trying to build it around yourself or a person? 

Wes: I think, yeah, I think a lot of the principles apply, I think with an individual, but I would also say this works for companies, having a spiky point of view is really valuable. And so when I say spiky point of view, I don't mean stirring the pot with controversial statements just for the sake of it. I mean, having a unique stance based on your lived experience that you are able to back up with evidence, stories, logic, et cetera.

And so something that teaches your audience something that they don't already know. If you are just saying stuff people already know, that's just not as useful, right? Like as consumers of content, we are, we're seeing a bunch of stuff and stuff that helps us think differently. That challenges a viewpoint in a productive way that when you read it, you think.

Oh, I never thought about it that way, but now that I read this, this makes a lot of sense. And this is actually giving me clarity about some problem that I am dealing with. Like we all encounter content like that and it's awesome and we wanna follow that person. We believe that they have something to add to our lives and values that they can add.

So on the creator side, if you want to grow your audience, you wanna connect more, you know, with your audience, thinking about how can I be that person? That is helping people think differently and teaching them something they don't already know, offering a spiky point of view, I think that's a really good place to start.

And I would say that almost all of my content starts with considering what is my spiky point of view here. It's very hard for me to write content that theoretically would perform well if I'm not interested in it. I just don't have the internal fortitude to, to follow through and write this post if I don't really, if I'm not fascinated by this thing myself.

So it's almost always what is triggering a reaction in me. If I read something and I think I really agree with this, and I, I think that, you know, the writer didn't mention this part enough and that's the part I wanna write about, or I disagree with this. I think that this is a bad take or the person is missing this variable.

And so I wanna talk about this factor, you know? And so something that triggers something in me that that gives me a spiky point of view. That tends to be the source of pretty much everything that I write, whether for a newsletter or for social or for anything else. 

Brett: When you're sitting down and writing something, are you good at knowing what will really, like if you put five things out, are you able to sort rank, which will resonate most?

Or you're often surprised when you put things out on the internet while this really took off and people connected with, and this I thought was really interesting and nobody really cared?

Wes: I'm definitely surprised by folks either liking something more than I expected, or less than I expected. But everything that I post and put out I expect to do well.

Like I don't put out anything unless I think that it has a chance to really resonate. There's not a, a very wide range where, you know, I'm, I'm posting something that I think won't really land and then it lands, you know, it's more like within this range of a bunch of things, I think will land, some things land harder and more, more than I expect.

And then some things land a little bit less. 

Brett: And do you think that's fairly random in the sense of like, somebody reads one thing, they share it and then it creates sort of this cascade? Or just you can kind of create a threshold, which is like knowing my audience and knowing myself. I have a bar in my mind that I will not put something out that's below it, but outside of that, I actually have no idea what will resonate more or less like humans are complicated.

Wes: Yeah. I think if we're looking at engagement metrics as what resonates, there are times when I post something and it has 700 likes and dozens of comments, and I would say that that's a pretty successful post on LinkedIn, and then I'll post the same thing six months later and it'll have 300 likes. The content was the same.

That to me is a sign that looking at the engagement itself is not a super clear picture of did this resonate or not because the algorithm, timing, et cetera. What else happened that day? Like there's a lot of things that are outside of my control. I generally have a sense of if I write something, I would say like 10% of the time I think, this is gonna be a banger. Like this is good. You know? And then the other 90%, it's like, I think this is important. I think people need to know it. I think this is interesting. And then I'm not sure, you know, are people gonna resonate or not? But again, there are so many things outside of your control. So like a couple months ago I posted about how to give senior leaders feedback without getting fired.

So it was a newsletter post, and it became one of my top performing newsletter posts because someone shared it on Hacker News. Then it like made its way around a bunch of people. You know? So there are those factors which, you know, it's, it's just harder to control. But generally I find following my own interest to be the best way to figure out what topics to write about, which I wouldn't have expected that to be the case.

I think I always thought, I was always a little bit self-conscious about that. I thought that there was a, a more official or better way to, you know, write what people want and, you know, the whole listen to your customers thing. But I found that when I asked newsletter readers to share what they want me to write about, to share questions, I wasn't inspired by their questions.

I just didn't have anything to say. Like, I would see the question and be like, okay, that's a good question. I don't, it's not triggering anything for me. You know? Whereas when I reflect on my own experiences and things that bother me, pet peeves of mine, things that I think are annoying, that's where a lot of my best stuff comes from.

And I think I. You know, that's kinda going full circle to, to what we started with, how important it's for founders to have a point of view. Some of it has to come from within you, and the stuff that comes from what I am personally fascinated by and think is annoying or whatever, that tends to create the best stuff, I think.

Brett: What's the last thing that annoyed you, that turned into something you put out in the world that was interesting? 

Wes: Everything, almost everything I write about the root is something that annoys me and then I turn it into something much more positive. Because the frustration part isn't always, you know, isn't always the best angle, but one that is more literal is, I did a newsletter article and then posted this on social as well about, no, I don't wanna hop on a call. And so this was about how many of us default to live conversations when they don't need to be live conversations. And it actually wastes everyone's time. And how, you know, if you are not sure how you wanna write a message and you're not clear on your idea, I, as your colleague, do not wanna be taxed listening to you talk, you know, meandering for 30 minutes as you figure something out in real time.

Like, take five minutes, think about it. And then if you really can't come with an answer, find the top on a call. But don't make that just your default. And there's obviously many good reasons to hop on a call brainstorming, you know, situations where showing your facial expressions or tone of voice matters, discussion, et cetera.

In my experience, many of the day-to-day interactions we have aren't that like it's a simple question or, you know, sharing information. And you can do that in writing in a much more scalable way that respects the other person's time. So that was an example of something where the beginning of that actually came from a question from a student in my course, because I'd shared a screenshot of a Slack message that was a little bit longer, multiple paragraphs and stuff.

And the student said, well, that Slack message looks long. Like, should you just hop on a call? And I got so annoyed by this question, like, what do you mean? First of all, this is not too long. I had grayed out to redact the content. So you have no idea what this says. How can you say it's too long without knowing the content A.

And then B Hop in a call doesn't solve the problem of this being a complex situation that needed to be explained. And in fact, it would probably take longer to hop on a call to talk through something that was really complex if you hadn't figured it out than putting it in writing after putting some thought into it where the person could read at their own pace, reread certain parts, note parts that they agreed with or disagreed with, you know? And so that's kind of the root of that post came from this question where I was like, wait, like there's, there's a gap here and you know, how can I write about it to address that? 

Brett: And then you got that student right out of the course, ejected them.

Wes: No, 

Brett: I was having dinner with, with a pretty well-known author last night, and she was saying that most of her books, the origin story is something that bothered her. And that's sort of how she chooses what to write about next. And so she was reading an article in the Washington Post where the author clearly didn't know basic statistics in the way that they were talking about this thing.

And I got her so frustrated that it ended up leading to the current book that she's writing, and that's basically how she decides what to do. 

Wes: Yeah, I would say that the inspiration for my course was rooted in, in frustration too, because I feel like there's so much communication content, books, courses that basically roughly equate communication with public speaking and delivery.

So there's a lot of advice on make good eye contact, project your voice, look around the room and there's a bunch of stuff on, you know, only 7% of what you say is, you know, based on the content. The rest is body language, et cetera. And I feel like most operators already know this unless you're super junior, like you kind of already know this.

And it's just not that helpful for learning and improving your ability to do well in a high stakes meeting that's moving quickly with stakeholders with different points of view, or it just doesn't help much with written communication either. Like how do you structure your thoughts in writing so that the other person quickly understands what you mean, understands what you need from them?

And I just, I felt like there was so much of communication that operators and founders do on a day-to-day basis where public speaking is actually a terrible mental model. If you think about it with public speaking, it's one directional. You're sage on stage. You have one speech, which you perfect your TEDx talk, where like every hand gesture and word is so perfectly mapped out, no one's interrupting you midway to ask you questions.

This is not how presentations or meetings or conversations go in a company, you are constantly getting interrupted. It's not always bad, like people are sharing information or wanting to redirect. You're talking about different things every time. You're not repeating the same speech and perfecting it.

It's much more bi-directional. It's much more of a guided conversation than than a true, you know, speech or presentation. And I would say lastly, I think the most important thing is you are interacting with other intelligent colleagues. So this is not like you are the expert and everyone else is a lay person, and you have supreme like knowledge about something.

You are an expert speaking to other experts who are also sharp, who also have strong points of view. And they're not gonna suffer fool, you know, fools. They're not gonna pull punches. If something that you said doesn't make sense, the logic doesn't track, you missed a crucial insight, they're gonna call you out on it.

So the logic of what you are saying, the underlying idea matters a ton. And I just wasn't seeing any communication content. Focusing on that piece on situations where like your underlying idea really matters, being right, really matters. So how can you learn to be more right and communicate your ideas clearly, taking into account your recipient, the amount of cog of load there is, sharing your rationale and yeah, realizing that there was a gap there and, and wanting to fill that gap.

Brett: Maybe this is sort of a, a good place to wrap up and I think you already talked about Seth, so you, I, I wanna ask you to choose someone else, but wanted to sort of wrap up where we always do, which is like, who's the person that's imparted something on you that has had like incredible residual value? Like it's the type of thing that you're constantly going back to.

Wes: Seth is the one who jumps to mind here. I used to have a little Seth voice in my head for different situations and you know, I still hear it in my head with, you know, if I'm, he used to call it hiding where you do stuff that you know how to do 'cause you're more comfortable with it. There's less uncertainty and you delay writing the strategy doc, you delay solving this problem because it's very uncertain.

You're not sure what the right answer is, and he was so ruthless about calling me out whenever I was hiding, that I became very intellectually honest with myself on that as well. And so, yeah, I'd say that Seth is probably the person who comes to mind for that. 

Brett: Awesome. Well, thank you so much for joining and having such a wide ranging conversation.

I really appreciate it. 

Wes: Yeah, this was a lot of fun, Brett. Thank you.