Wes Kao | How to Design Transformational Learning Experiences

Srini Rao

Wes, welcome to the Unmistakable Creative. Thanks so much for taking the time to join us.

Wes Kao

Hey Trini, thanks, really excited to be here.

Srini Rao

Yeah, it is my pleasure to have you here. So I was introduced to you by way of one of our former guests, Michelle Florendo, who told me that you had worked with Seth Godin on the Alt-NBA. And then I had a chance to do some more ding. And then when we spoke, I found out we both had Berkeley in common, which is super cool. So I wanted to start by asking you, what did your parents do for work? And how did that end up shaping and influencing the choices that you've made throughout your life and your career?

Wes Kao

My parents were both retired pretty early. So as a kid growing up, I didn't really see them going to work in the normal way that other kids saw their parents going to work. I was very lucky in that they were able to be full-time parents for my sister, my brother and I. Before they retired, my dad was a land developer in real estate.

and also had a grocery store, one of the first Asian grocery stores in Fremont, California. And he was also an insurance salesman. So a couple different things. And then my mom was a student at UC Davis, studying computer science. And then she got pregnant with my brother. So she dropped out of college and she...

had a couple odd jobs, she worked as a housekeeper for wealthy families in the Oakland Hills. She was a bank teller for a while. So lots of different things. But I think the path that I ended up taking and the values that they instilled in me were obviously hard work. I think that's a pretty... That's a pretty...

basic one, I'll say, for people who grew up with parents that were immigrants. But yeah, I think the thing that I really appreciated about my upbringing and my parents is that they were not Tiger parents. I think a lot of people assume that they were. I'm flattered because, you know, that must mean they think I have my act together. And they assume that I had Tiger parents. But my parents were...

never pressuring or strict about, you know, needing to do this activity or this sport or, you know, piano lessons or this or that. I tried a lot of things, my siblings and I tried a lot of things growing up and we quit a lot of things. So at a certain point I was doing ballet, tap, jazz, gymnastics, horseback riding, oil painting, violin, piano,

Wes Kao

writing lessons, math, tutoring lessons, et cetera. And I was so grateful to have all of these chances to try these different things. And some of them I tried for like one lesson and realized it wasn't for me, like horseback riding. I think horses are terrifying, huge creatures in person. Like, I feel like you see ponies and, you know, calendar, I had, you know, a calendar of horses and these little horse figurines that I played with.

as a kid, and then I went to ride my first horse, and then you just realize that they're humongous. They're just huge. And same with, same with violin. You know, I took, I think like two lessons and realized that this was not for me. And so having the chance to experiment a lot and quit a lot actually helped me realize that it's completely okay to quit things that you are not that excited about, or you know, not that committed to, or don't feel like it plays on your natural strengths.

And of course there is absolutely value in sticking through something and having persistence. But I feel like a lot of times we force ourselves to continue things and this idea of suffering you know for the greater good that like suffering equals progress. And it's taken me a long time to apply that to my career and to realize that suffering does not necessarily equal goodness.

And in recent years, I've kind of gone back to, okay, you know, back then I quit a lot of things, tried a lot of things and it was great. You know, in recent years, I've realized that I want to lean into my strengths. I want to do things that where the process and the journey of doing it brings me joy, not some, you know, end outcome of, you know, being the best at, you know, this thing playing Carnegie Hall 20 years later or whatever that end goal might be. So yeah, I'm

a big proponent of leaning into your strengths, choosing things you actually like doing and don't consider a slog. And I love seeing friends who love practicing their instruments. They love practicing the cello or the violin, or they look forward to dance classes, or they look forward to horseback riding lessons, or they look forward to art classes. Like that is amazing. Like you should look forward to the thing that you do.

Wes Kao

whether it's a hobby or whether it's work. So, yeah, I think actually one of my greatest strengths, which now that you asked this question, makes me reflect onto the origins of it. I think one of my greatest strengths is picking battles that I can win and picking games that I feel like I have a shot at and would like playing, and not necessarily just persisting through something just because it feels like I should.

Srini Rao

Yeah, I appreciate that so much because one of the things that I see in the online world and this is something that I have said is the ultimate form of bullshit where, you know, you'll see some prominent person say, oh, everybody should do this. Like everybody should start a podcast. And it's like, well, no, there's nothing everybody should do. It's like, you know, when parents said when we were kids, it's like, if all your friends were jumping off a bridge, would you? And I feel like so often people get caught up in that and they ignore their

you know, actual strengths, and as a result they become average at dozens of things instead of extraordinary at one.

Wes Kao

Yeah, absolutely. I think one of, it's weird because we celebrate persistence and grit and, you know, working through hard things. And I believe that. I absolutely think that those things are important. I think we apply it too broadly though. Like we apply it even for things where we should probably quit that thing. Like if you're not that good at something and you don't really like doing it,

Why are you doing it? There's probably other things that you are naturally better at. And when I was starting Maven last year, one of the things that I thought about was if there is someone else on the street, like a random person on the street, if they worked super hard and applied a lot of effort, if that person could start this company and do what I'm about to do, then I shouldn't do this.

because working hard is kind of a, I consider it table stakes. Like everyone's gonna work really hard. So that's not really a differentiator in my mind. Like there should be some other advantage that I have, some other edge, right? Some insight about this group of people that I wanna serve or a track record of doing, solving this particular problem or a special zest in wanting to figure out, you know.

this problem or whatever like there should be some edge that I bring that allows me to do this better than a random person on the street

Srini Rao

Well, it's funny because the only reason I started a podcast was my first business partner, Sid Zavara, told me, he said, you're an average writer, but you're a really good interviewer. He said, you know, so I think you should take this little mini project you have on your blog and spin it out as a separate site. And to this day, I still think he's right. I'm a far better interviewer than I am a writer. And the numbers kind of speak for themselves.

Wes Kao

Yeah, I love that.

Srini Rao

Let's talk about this whole idea of your parents not being Tiger parents, because that's so unusual for somebody of Asian descent. I mean, I'm an Indian immigrant who went to Berkeley as well, and I had the standard Indian kid sort of narrative of, you want a good life, become a doctor, lawyer, engineer. It doesn't sound like you had that experience. So based on sort of the way that you were raised, I mean, as somebody who has played a big role in kind of reshaping the way we educate, what would you say to parents who are listening to this?

about the educational experiences of their children, especially the ones who are like, oh, this kid is gonna turn out to be a total screw-up or they're not gonna go to some crazy Ivy League or elite school. Like, what would you have to say to them based on your personal experience?

Wes Kao

Yeah, I would have them look at me now, which is, you know, moderately decently successful, I would say, and reveal that when I was a kid, I had a lot of trouble in school. So if their kid is having trouble in school, you know, they can still grow up to decently, you know, have their act together.

So I think that's very encouraging. I think even when I look back at my younger self, I'm motivated and encouraged because I remember being in school and having a hard time learning how to read. I remember in kindergarten or first grade when teachers would have flashcards and it would be like a picture of something, like an apple, and then it would say the word apple underneath, and they were trying to teach everyone to sound out the word.

right? Like a-puh-le-ro-apple, right? Um, and I wasn't really understanding. Um, and I remember my teacher pulling me aside to do extra exercises with me one on one in the back of the room when, when everyone else is doing, you know, other things. And, you know, she had this flash card and there was a picture of a hamburger and she was like, okay, read this word. There was a word underneath and I blurted out hamburger. And I was so excited.

because I thought I had gotten it right. And she was like, no, like read the word, sound it out, she started getting frustrated and the word was bun. So she wanted me to sound out bun. And you know, that's just one example that I can think of. There's so many where, you know, trying to learn how to read a clock, trying to count coins and like, and add up coins and dollar bills, trying to understand shapes.

Um, you know, that's just, you know, very early on in elementary school, but, but later on, um, you know, math, especially, um, uh, algebra, um, geometry, et cetera, right? Like trigonometry. I really needed extra support. I needed extra tutoring to get these concepts that a lot of students.

Wes Kao

Um, we're able to understand more intuitively just from class time alone. So, you know, so that's, that's just, you know, understanding what the teacher was putting down. Uh, and then on the other hand, um, there's a whole other bucket, which is standardized testing. I was terrible at standardized tests. So it wasn't like, Oh, she was bad at the classroom stuff, but you know, good at testing, no, I was pretty bad at both. So with testing, um, you know, I always felt like I.

I kind of did decently well. I was like, okay, you know, I think I got this. And the test results had come back for like star testing in California and whatnot, SATs, SAT-2s, terrible, like terribly traumatic experiences. And the scores would always be very, very mediocre. And I remember one time in school, this was in elementary school, the teacher called my parents in because my standardized testing scores were so bad.

And they're like, hmm, like what's going on here? Like, let's talk to Wes's parents. And you know, they gave an example of a reading comprehension paragraph. So you remember those, that kind of thing, right? Where it's like, you read this paragraph and there are five questions that show that you understood what was being said. So it was a story about a boy on a really hot day. The boy's walking home. The boy sees a cool lake. And...

Srini Rao

Mm-hmm.

Wes Kao

then it was like, what does the boy do next? That was one of the questions. It was like A, B, C, D, E, and I think I chose like D, goes home. And the correct answer was something like B, jumps into the cool lake. So, you know, so they were like, okay, let's see like what's going on at home. Like, you know, why is Wes not understanding this? And in my mind, it made so much sense. Like the answer that I chose always made so much sense. And I always just wanted a chance to explain.

Srini Rao

Yeah.

Wes Kao

to the test taker. Like, here is my rationale. Here is why, like, this is actually as legitimate of an answer as, you know, whatever, whatever you think the answer is. And in my mind, it was lakes are dirty. And my parents, you know, when we were growing up, they're like, oh, like, let's swim in pools. I don't know if this is like, again, like a first generation immigrant thing, but they're like, oh, like lakes, like there's like rocks and like, and leaves kind of floating on the surface, and it looks kind of murky, and who knows what's underneath there? Pools seem much cleaner.

Anyway, so in my mind, it was like, okay, this lake is kind of dirty. And at home you have soda in the fridge and air conditioning. So go home.

Srini Rao

I Laughed and smiling because I feel like you and I are sort of kindred spirits I struggled to tell time my parents always had to get me watches that basically You know only had you know sort of digital readouts like I could never tell what the hell the time was that was one Of those weird things much like yourself. I sucked at math Ironically that was failing reading in fourth grade and somehow I became an author And of course Indian parents like you know

Wes Kao

Amazing.

Srini Rao

Your kid doesn't, my parents are like, yeah, no, he doesn't have a learning disability, just shitty teachers, and of course, 20 years later I get diagnosed with ADD. But I relate to the standardized test because I probably took the SATs three times, which makes me wonder, how in the hell did you get into Berkeley if you were so bad at standardized tests?

Wes Kao

Yeah. So ironically too, I haven't publicly said this before, but I also recently got diagnosed with ADHD. So that's, I love that you are a fellow ADHD, I don't know, haver or, or whatever. So yeah, I I've been actually reading up a lot on ADHD and, um, and it's, it's been so, I don't know what, what the right way to describe it is.

it's been a relief, like reading about and being like, yeah, I see myself in that. Like these case studies of patients who have ADHD, it's like, oh yeah, I see myself there, I see myself there, not so much there, but that trait expresses itself a little bit differently in me and it's really amazing to understand more of how our own brains work just in general. So I feel like that it's added a different layer to how I...

view myself, how I process and, um, and, uh, think about laying out my day and whatnot, but anyway, we can get into that later. So yeah. So how did I get into Berkeley with terrible standardized test scores? Yes, I have, I have wondered the same thing myself. And not only that, not only that, my friend, I also had to apply, uh, at the end of sophomore year at Berkeley, uh, to do my last two years as, as a Haws School of Business.

undergrad business major. As you know, we've talked about this a little bit before.

Srini Rao

Yes, which I did not manage to accomplish. Like I, you know, failed. So.

Wes Kao

So, no, like that's, I'm just as shocked. And you had to have, you had to have a good application that showed, you know, your leadership skills, but also your grades for different prereqs. So, you know, micro econ, macro econ, intro to accounting, finance, and yeah, so I...

Srini Rao

Mm-hmm.

Wes Kao

Yes, was very, very grateful that I was able to make it in to Oz. I think mainly I compensated in other ways. I think that's probably the best way to say it is I knew that my grades were never going to be a differentiator for me. And my...

test taking ability was also not a differentiator. And that's putting it lightly. It's like, it's not only not a differentiator, it's a detractor. So I needed to be so much better in other ways to prove that I could be something and that the school should take a bet on admitting me.

Srini Rao

Well, so in a system that primarily rewards people based on academic criteria, like grades, I mean, you and I both know this from Berkeley. Berkeley's a shit show of an experience to go through. My dad had a colleague once when I was in high school who said to me, he said, if you survive undergrad at Berkeley, everything else in life will be a piece of cake in comparison. And truth be told, I've had a number of friends who've told me the same thing, like so.

Wes Kao

That's hilarious.

Srini Rao

My sister went to medical school. She said medical school was a joke in comparison to undergrad at Berkeley. I had a friend, who's a Harvard neurosurgeon, and he said when he got to UCSF, which is the best med school in the country, he said that people who come from Berkeley find it to be really easy. He said people who came from Stanford actually struggled with that first year. And to me, I think the big sort of life skills that come from Berkeley are how to deal with immense amounts of bullshit.

Wes Kao

Wow.

Wes Kao

Mm-hmm.

Srini Rao

But I think I told you the story of my friend who went to Haas. He didn't get in. So he took all the classes for two years and two weeks before graduation, walked into the dean's office, and said, my parents are coming on Saturday. You're going to let me walk or not? And at that point, she had no choice but to relent. And somebody once said, what is the thing you learned? I was like, I learned how to navigate bureaucracies and manipulate systems to my advantage. That is the greatest skill that came from being a Berkeley undergrad. And it's funny, because.

My grades were definitely a detractor like yours. Like you've probably seen this, right? When you go into those investment banking interviews or a Google interview, they'll ask you one of those damn brain teasers. And if your brain doesn't work like that, you're just like, what the hell? So this is my favorite one, right? How many golf balls fit in a 747? And now I would say, you know what? Unless Richard Branson and I are gonna do a bunch of XC together, why the fuck would I need to know that? Like I can't imagine any scenario in which that

Wes Kao

Oh God, those Jesus.

Srini Rao

will be useful. So in a system where, you know, whoa. Ha ha ha.

Wes Kao

slow clapping over here for you right now. Yes. I want someone to ask you that question so you could give that response because it's so true.

Srini Rao

Yeah, me too. So, but when you're in a system like, you know, an elite college like Berkeley, and you're trying to basically compensate for the things that, you know, typically are awarded and typically lead to progress or to, you know, acceptance, how do you compensate for that?

Wes Kao

Well, in high school, I started a nonprofit organization. And I think that was a really huge leadership experience for me because before then, I had never planned anything bigger than a birthday party before. And so going straight into freshman, sophomore year of high school,

deciding to embark on this huge project, that was a transformative moment, not moment, I mean, I ran it for five, six years. So transformative experience overall. So I think that starting Packs of Love was huge. The organization was called Packs of Love. I donated backpacks and school supplies to underprivileged kids, to foster kids, family resource centers, domestic violence centers,

Um, it, you know, in the beginning, the, the way I got the idea was I was cleaning my room and I dumped out all my notebooks, pencils, pens, markers onto the floor and I had a bunch of stuff from, you know, hello Kitty, Lisa Frank, uh, you know, all my goodies. And I was kind of organizing them. And my dad walked into my room and took one look at, you know, this explosion of stationary and said,

you know, you are so lucky. You don't know how lucky you are. There are kids who don't have a fraction of this and blah, blah. And usually during his lectures, I would smile and nod and wait for him to go away. Um, and you know, this time after he went away, I continued organizing. And I, I thought about what he said and realized that I did have more notebooks and brand new pens and pencils than I would ever have a chance to use. And

what if I donated some of them to kids who might need them? And so I thought of this and was immediately very proud of myself for thinking of this. And it wasn't until I tried executing a couple of weeks later that I realized that turning this idea from an idea into a reality was much harder than I thought. And I realized this because I started going around to local stores in my neighborhood.

Wes Kao

to ask for donations. So I would go to Longstrux, Walmart, Target, Walgreens, and I would ask to speak to the store manager and I would bring this folder with me with a write-up of my proposal of what I wanted to create. And I would wear my only button-down shirt and some black Capri pants to look a little bit more professional. And I would go around and ask to speak with these store managers. And...

pretty much every single manager laughed in my face and said, you are a kid trying to get some free stuff. I see you. This is a joke, goodbye. And it was very demoralizing. And at the same time, I was kind of like, okay, yeah, I can see how me showing up in your store asking for free stuff could, you know, like could be interpreted that way. Like I didn't have any credibility. I was a single random person. I wasn't.

part of an organization or a school club or affiliated with anything. I really was just a random kid asking for pencils, notebooks, and backpacks. And so I understood their skepticism. So I ended up trying a bunch of different things. I wrote a bunch of letters to different corporate offices. Back then, I really did not have a single clue what I was doing, so I would address a letter to one Microsoft way.

to who it may concern. And like, you know, the Microsoft campus is like a mini city with multiple departments, like thousands of people. I wrote it to like the lobby or something. Like, who knows where that letter goes? Probably directly into the trash can. Anyway, I sent out hundreds of letters. I also wrote to backpack companies, backpack brands like Jansport, Eastpac to try to get donations to Pentel.

Um, and, uh, a bunch of other, other stationary companies, um, uh, staples. And anyway, um, none of it worked. So kept getting rejected. It was all great. Cause I learned, okay, this is hard. Uh, and I should keep trying. And so, okay. Like I now know what doesn't work. Um, anyway, that first year that I was, that was doing packs of love, I ended up.

Wes Kao

needing to use my own money to buy backpacks and school supplies to donate to a shelter that I had already promised I was going to get them 50 backpacks. And I felt so bad about it that I was like, okay, I'm just going to, I'm just going to buy this and, uh, and, and keep trying. The one thing that I did do that was pretty clever was after I donated those, uh, initial 50 backpacks, I called the local newspaper and I told them

Hey, here's what I'm doing. Here's the donation that I just made. I'm trying to build this charity. And if you think this is something that could be interesting to share with the community, let me know. And a reporter replied and was like, yeah, like this is super cool. You're a 15, 16 year old trying to do this. Like this is kind of random and kind of neat. So yeah, I'll cover it. And I ended up getting on the front page of the local newspaper.

And this was a huge win and probably the first win out of, you know, months of effort. So I bought 50 copies of the newspaper and I then went around to all of the same stores who rejected me and mailed this newsletter, newspaper clipping to all the companies that replied saying, sorry, we're not able to donate. And the same places that rejected me all of a sudden were interested. Now I had a little bit of credibility.

And I also dangled the possibility of, you know, hey, if you, if you donate, I'll mention it to the reporter, uh, the next time that I'm interviewed that, you know, the store manager at Walgreens in this local store was able to donate and, you know, and that'll make you look good. It'll make you seem like part of the community giving back. Um, and I basically did this cycle, um, and worked up the ladder over the next five, six years until I was getting.

Backpacks boxes of backpacks shipped to my house and talking to district managers who managed dozens of stores statewide to Offer donations and was negotiating these deals Every summer in preparation for the fall donation time And you know and got other students at my high school involved

Wes Kao

and expanded into donating more and more backpacks every year. Um, and this, this ended up being one of the most formative periods of my life. Um, and it showed me that I could make change happen. It showed me that I could take an idea from being an idea and turning it into something that was real.

something that, um, that other people understood and, and change something in the physical world, right? But not just in my own head with an idea, but, but something actually in the physical world that I could build something. And it also taught me the importance of marketing. I didn't really know what marketing was until this time, until I realized that the way that I tell my story, the way that I position this charity, the way that I describe,

the impact, the way that I align incentives with the people that I am trying to get donations from the way that I celebrate the behavior that I want to see. Um, all of this I realized was marketing and that was really what, what planted this initial seed of wow, marketing is so incredibly powerful. It is literally the difference between people closing doors in your face and saying that you are a joke to people signing.

thousand dollar checks and mailing you thousands of dollars worth of product because they believe in you and because they believe in what you're able to do. They believe in your vision.

Srini Rao

Wow, okay, amazing. So let's shift gears a little bit. How do you go from Berklee to working with Seth and talk to me about the experience of working with Seth because I've had probably half a dozen people here who've all basically said it's completely insane, it pushes you to your limits and what he proposes often sounds impossible.

Wes Kao

Yeah, that's very, very accurate. Now I know that you actually talk to people who worked with Seth. Because before I was kind of like, okay, like, you know, some people will meet Seth, you know, they'll come by our office and Hastings on Hudson and sit with him for an hour and talk to him and be like, oh, I worked with Seth on this and this. But people who really worked with Seth would say something different, which is, yes, it's freaking intense and completely bonkers.

and extreme in many, many ways. And so, yes, like the way that you described it just there is pretty much what it was like for three years.

Srini Rao

Yeah, I think it was Willie Jackson or even Seth may have told me that up for the Domino project like on I think two weeks Then he told them he was gonna fire everybody if they didn't do something Well, I think the thing that I find so insightful about and I think also is so challenging with his material for a lot of people is he doesn't give people a map he gives them a compass and He basically forces you to figure things out on your own is one of the things that I've observed

Wes Kao

Yeah, I love Willie.

Wes Kao

Yep, that sounds about right. That's hilarious. Good times.

Srini Rao

in the way that he teaches. And you know, like if you look at the negative reviews of any Seth Godin book, the one common complaint I feel like you see is he doesn't actually explain how to do this. And I realized that is by design based on the conversations I've had with him. So I think that makes a perfect segue into talking specifically about designing transformational learning experiences. Because I mean, you and I are kind of like as I would.

like to joke failed byproducts of a traditional education system. Like we've been able to accomplish what we have not because of Berkeley, but in spite of it. So when you look at education as traditional form and also how people learn online, what is it that leads to the kind of transformation that

Wes Kao

Mm-hmm.

Srini Rao

produces the outcomes that people who come out of creative MBA or all to MBA get. I know this, my cousin Ramo was thinking about an MBA and I told her not to do it. I said, a business school is a complete waste of time and money, it doesn't teach you shit about how to run a business. And so I referred her to all to MBA and she got like a massive promotion afterwards, where she's now like one step down from the CEO of her company. And then she ended up starting a business too. And so one of the things I'm very curious about is, you know, typically what I've seen,

Wes Kao

Wow, amazing.

Srini Rao

When I look at the way that people consume content, particularly on the internet or take online courses, something like 80% of people never even fucking log in. They spend like $1,000 on something and they never open the damn course. I've seen this with my own students. I've seen it myself. I mean, something changed at some point where I just learned how to do this. But the thing is that I think that there's also responsibility on the part of the person who creates something

design experience that actually facilitates real learning. Because I think now about college in particular, and I think back to things like Econ 101, which is the course that you and I took, right? And this is one of those sort of realizations I came to as I was reading The Wealth of Nations, which I would have never been able to do in college. And that is you go into an econ class at a place like Berkeley, and what do you do? You know.

highlight and underline the shit out of a textbook. Like if you go and pick up a used textbook, you'll see that somebody has highlighted the entire book as if that's gonna be of any use. And then you do problem sets and you think you understand something and then you get to the midterm and they present this idea in a context that you've never seen before. And that's when you realize you didn't actually learn it. So anyways, given the role that you have played in Alt-NBA, like what is it that...

needs to change about the way that we design these learning experiences. Like, what are the foundational elements that lead people to have transformative experiences? Which I realize is a question we could spend three hours talking about.

Wes Kao

Yeah, I think the biggest, the biggest thing is a mindset shift. So right now and pretty much throughout history, if a student doesn't learn something, we blame the student. We say you weren't paying attention. You weren't focused. You are, you know, are slower than everyone else. You need to try harder. So it's the onus is on the student to understand.

And in the meantime, most professors, I would say, are in a position where they are one of the last bastion of content creators. If we want to, you know, use content creation kind of broadly, professors are, are one of the few content creators where their audience is chained to their desk and they can't leave. So no matter how good or bad you are of a professor,

your students have to stay and listen. They have to attend your lectures. They have to attend the discussion sections. And the whole education system is very stick driven. If you think about carrots and sticks, like sticks being punishments and carrots being rewards, it's usually stick driven. It's saying, you know, you won't be able to pass this course. So you won't get the credits. You'll have a dark smudge on your report card or on your GPA, or you won't be able to...

graduate with this major, you know, and that'll look, that'll be looked down upon if you have replied to grad school or, you know, future employers won't like that. So it's very, very stick driven. And it's not carrot driven enough carrots, meaning how do we encourage students to want to pay attention? How do we make the material more engaging, more relevant, more timely so that students can see how this fits into their daily.

life or how it shapes them to become a more critical thinker on a more macro level. So I think this mindset shift, this philosophical shift of instructors embracing that they are responsible for their students' transformation and embracing that in today's day and age, you have to be 50% instructor, 50% entertainer.

Wes Kao

you have to, you can't, you can't just spew facts because first of all, if you were just viewing facts and someone could just watch a video of you doing that and probably, um, a more engaging professor, uh, a video of a more engaging professor doing that. Um, and so if you're, if you're teaching live thinking about, you know, how do I embrace that I am, um, both, both sharing knowledge and content and information, but also thinking of myself as

Um, someone who wants to keep their audience entertained. I think that's increasingly important, especially if you are not a professor, like just, you know, I was using higher ed as an example, but especially if you are, um, teaching a core based course or a self paced Udemy course, and you don't have those sticks, your, your students are taking your course because they want to improve themselves out of their own free will.

They are not doing it because they get punished if they drop out of your crypto course, if they drop out of your leadership and management course. So it's even more important for the majority of us who are not in the traditional education system who are teaching outside of it to embrace this idea of 50% instructor, 50% entertainer.

Srini Rao

You know, it's funny you say that because that literally is part of the reason that I ask all these completely irrelevant questions to start a podcast because, you know, this is something I realized a lot of online marketers overlooked. I was like a podcast is a storytelling mechanism first, like audio is an entertainment medium first and an information medium second. Like nobody wants to hear 10 tips on how to grow your Facebook following on a podcast. That'd be fucking mind numbing.

Wes Kao

Mm-hmm, yeah, exactly, I love it.

Srini Rao

I mean, those are my three pillars, is entertainment, education, and inspiration. Like, those are, people always look at like, is there a criteria for how you choose? It's like, if we can accomplish those three goals, that's a perfect guest. And you know, they're not mutually exclusive. Sometimes it's just entertaining, you know, and not necessarily educational, but I think if you can get that trifecta down to me, that's like how you create really emotionally resonant content. So, one thing that always struck me about the...

concept of all to NBA was that there are no homework assignments, there's no lessons, there are no lectures, which you know is so different than anything out there. And I remember one of our copywriters said, you know what, if we're gonna teach this writing course, let's do it differently. He said instead of having you come in...

you know, have people watch you present slides to them, make them watch all the lecture material before they come there and just use, you know, the hour that you have with them for discussion. That ended up being invaluable and it was a hell of a lot more fun for me.

Wes Kao

Yeah, I think when you have live experiences, you really want to spend it doing stuff that you can only do live. So with first time course creators, I always recommend that they aim for having 75% of their workshop be interactive. So discussions, debates, critiquing each other's work, giving each other feedback.

doing demo days, pitching something, then, uh, then, you know, people reviewing each other's pitches, um, breakouts. And then that 25% is lecture or anything that, you know, you really can't think of a way for people to learn this in a more, um, active way. Then you put that as lecture. Whereas, you know, the majority, the, the default that, uh, most instructors do is think, okay, it should be 75% lecture.

that I have a lot of material I wanna get through, I wanna tell you all these things. So it ends up being very lecture heavy. And I've never heard a student after a course say, gosh, I wish there had been more lectures. People usually say, I wish I had more time to meet other students. Or I wish we could have done this breakout for longer because so-and-so was giving me really insightful advice that I just hadn't thought of before.

Um, or so, you know, our group was getting into this really heated debate and I w and it was changing the way I was thinking about a couple of things. And that, that kind of pushing that you get from working with peers, from working on a project hands on and really needing to get into the nitty gritty of it, you know, not stay at a high level theoretical level, but, but really get into it. Um, as a group, when you're working on a project together, that is so much more.

impactful and teaches you so much more about how to think and helps you reflect on even what you think, then having a lecturer talk at you for the majority of the time.

Srini Rao

Yeah. Well, I mean, I know that you've played a role not only in all time, but also with Tiago Forte, building a second brain, which that has been one of those concepts has been life changing for me and a lot of people who truly understand it. So it's funny because you're kind of making me think about the course that I created recently. I have a course on mem, the note taking app and people are in it, but what's funny is

the best parts of that course are when I interact with Mem's Slack channel and the people who are there. Some of who are students, some of them are employees of Mem. It's not necessarily like lecture, and it's kind of making me rethink the design of the course, just talking to you. So starting with this idea of 75% live and 25% lecture, let's just say we're starting from the ground up with something, or even using Tiago as an example.

What is it that he does differently that you've seen than anybody else that makes the course so much more valuable than say other learning experiences? Because I was thinking about this last night, I was writing about this idea of taking smart notes, and Eric Wall, who we had here years ago as a graffiti artist, he told me something that I have never forgotten. He said, live music has keynotes, engaged participants, keynote speaking has passive consumers. There's room to be explored in how you bridge the gap. And that...

had a huge impact on everything I did from the way that I planned events to now thinking about it even in the context of how you take notes and how you create an online course I'm realizing that really is you know a huge differentiator.

Wes Kao

Yeah. If you look at evergreen self-based courses, on-demand courses, they're basically a series of videos and that is a passive content consumption activity. That's that's pure passive content consumption. Whereas if you look at a cohort based course or anything with a live component, it's much more interactive. That's why your students are picking a cohort based experience over a static

Async experience is because they want that community. They want that interaction. They want to talk about ideas and have other real humans listening and, and reflecting back. And they want to hear other real humans, um, ideas on this topic. Um, and yeah, I think that the passive versus active piece is a really, um, key difference between MOOCs versus core based courses. And it's one of the main reasons why core based courses are growing in popularity.

because MOOCs it's, you know, people tried it and the completion rates are super low, anywhere between seven to 10%. And a recent MIT study said even lower at three to 6%. So I think a lot of us have had that experience where we tried doing something on our own. Like it's, I mean, if it, if it could work, it'd be pretty great. Like if I could get myself to watch a bunch of these videos, to learn a thing, um, and motivate myself and keep myself accountable, I totally would. But it's the fact that like that's hard and I can't do that.

I've attempted it and I couldn't. And instead. Committing to a course where there is a start and end date. Like that even, even that immediately creates a sense of urgency and creates a sense of focus of, all right, well, this course is two weeks. Once this two weeks is over, can't turn back time. Can't get my money back. Like I should focus during these two weeks. Even that alone, um, helps me, um, prioritize.

learning this thing, you know, long enough for me to actually stick around and learn it. Um, I think that, that accountability piece is something that, um, I think all of us need when we're learning something new and when, when things get hard, it's just so easy to, um, to give up if no one's watching. But if you are, uh, if you've already committed to doing a course and you know that your fellow students are going to be disappointed if you just dropped out, that's often enough to keep you going.

Srini Rao

Yeah. I mean, I love the idea. You're making me think I could condense a six week course into two weeks and still deliver the same value.

Wes Kao

Yeah, I think with core based courses, the exciting thing is that there are so many different ways that you can lay out a course. And the experimentation is part of the, it's a feature of core based courses. So with a MOOC, for example, you put a lot of effort into recording everything, scripting everything, polishing it, editing it. And then once it's done, it's kind of there and it's hard to go back and change certain things. But when you are live, the live...

modality lends itself to experimentation. It lends itself to going with what your particular group of students in this particular cohort is interested in. And it might be that you went in with, you go in with a hypothesis that, you know, this part I can kind of go over quickly because people get it or they're not going to be that interested. And then when you're actually, when you're actually sharing it, it turns out that your students are very interested in this topic and they want to spend the rest of the workshop on the topic.

So you have that option when you're doing something live to cater that material to your audience. And I think also with what you said with, um, with doing a six week course in two weeks, potentially. Yeah, absolutely. I think, uh, the way that, that Maven teaches course building is very modular. So I see different modular components and parts of a course. And then once you have these components, if your course is six weeks, if you wanted to create a condensed version of that,

you don't have to start from scratch. It's not like you burn everything from your six week course and then start from scratch with the two week course. You can reuse a lot of stuff from your six week course and you put it in a different container where the constraint is now a shorter length of time, let's say two weeks. And then you think about, all right, how do I rearrange these different components to make it something that is shorter? Or you can even, you can go the other way. You can make it longer. Let's say you wanted to do an extended version, a 12 week, a 12 week.

course. You can also rearrange these different components to stretch certain things out, condense other things. So I love approaching, uh, approaching courses and, you know, projects and products in general with this modular mindset where, um, you have that flexibility to, um, change up certain constraints, but still reuse a lot of the great stuff that you already created for your course.

Srini Rao

So it's funny. One thing that I wonder is, what is it going to take to make this a more predominant narrative in traditional education? Because I remember talking to Saleem Ismail here. We were talking about Singularity University. And this is probably the thing that struck me most in our conversation. He said, you know, we can't get accredited. You know why? He said, because we update our curriculum in real time. I was like.

So let me get this straight. You're actually teaching people to adapt to current times and for that reason you can't get accredited. And he said, yeah, accreditation is a giant mess that prevents this kind of stuff from actually becoming more predominant in traditional education.

Wes Kao

Yeah, accreditation is a whole other beast that I don't know very much about because our core based courses, Mavens are, and the ones that I've worked on before that, so Alt MBA, Tiago's course, Build a Second Brain, Right of Passage, all these courses were non-accredited and were geared towards adult learners who are upskilling, retooling, improving themselves on their own.

So the whole, the whole accreditation piece with, you know, getting college credits to, to go towards a degree or, you know, to go towards, uh, something more formal is not something that I have a ton of experience in. And I also don't really know if I, um, am a huge proponent of that idea. I mean, when, when Seth Godin and I started the Alt MBA, we talked about accreditation and we talked about credentialing.

And there are pros and cons of credentialing. There are some instructors and courses who, uh, where it makes sense to go that path, to give a certificate or, uh, you know, a, a document of completion of some sort, um, so that totally makes sense. But with the alt MBA, we didn't want to do that. And it actually felt antithesis to, um, the whole point of the alt MBA. Um, it's the alt MBA philosophy was.

If you are doing a course, you should measure the results of that experience based on how you change afterwards and how your behavior is now different, how your mindset is now different and the results that you get because you are now an improved person, it's kind of like, if you take a sales course, are you, are you, is the certificate that you took this sales course, the important part or the fact that you can now close sales in half the time and you have

Srini Rao

Yeah.

Wes Kao

you're way more confident going into pitches. Like, right? So, you know, I think it's really the latter. So I see both sides of that piece. And I think more and more professionals are seeing that they don't need to go in the traditional education system and get accredited, et cetera, et cetera, or get a certificate to see the results and value that they wanna see from taking a course. They can measure the worth of that course differently.

Srini Rao

Yeah, totally.

Srini Rao

It's funny you say that because like, that a listen has this course on Rome and I went in and I took the whole course and I was like, all right, I'm still terrible at using Rome. But because of that course, I was able to create my note taking course. I used all the concepts and just applied them to another, another tool.

Wes Kao

Wow. Yeah.

Srini Rao

Well, let's talk about one final thing, which should bring us full circle. We started out kind of talking about moving towards the things that you're naturally good at. And I think a lot of people ignore that advice constantly because you have this sort of thing where social influence plays a big role.

Like personally, I think the biggest bunch of bullshit to ever come out of any online marketers, online marketers mouth is everybody should start a podcast. And I'm like, no, if you're an introverted visual artist who doesn't like talking to people and you're amazing at doing that, don't start a podcast. If you suck in front of the camera, don't start a YouTube channel. And yet the problem is that if somebody who's highly influential says this, people treat their word as gospel instead of guidance without thinking about this or questioning it in the context of their own lives.

how do they actually develop the capacity to consider context when it comes to prescriptive advice?

Wes Kao

Oh man, this is a really, really great question. I often think about this when I tweet something and then the comments are, you know, people who are pointing out an edge case or, you know, a different situation and they're basically applying what I'm saying to literally. And usually I agree with those comments. It's like, yes, I had 280 characters, but.

But otherwise I agree with what you're saying too. Like there are multiple ways of looking at something. I think developing that sense of judgment is very, very important. I've thought a lot about how to help people develop this sense of judgment and intuition around, how do I tell if a piece of advice works for me? Because if you think about it, we get conflicting advice all the time. We simultaneously hear patience is a virtue and good things come to those who wait.

And then we also hear that, you know, you have to go out and get the things you want or, you know, if you if you wait too long, life just passes you by. And it's like, OK, well, both things are true. But applying it and having the wisdom and judgment to apply the right piece of advice to your own situation is a skill in and of itself. So I think that this is yeah, this is this is a pretty, pretty big issue.

And going to, you know, going to the, that's kind of the macro point, but going to your, your immediate question of, um, you know, certain people shouldn't start podcasts or certain people shouldn't do certain things. Everything takes longer than you think. This is one of my mantras and I am on at least on a weekly basis, reminded that everything takes longer than you think. So the reason you want to do stuff that you are good at and actually like doing is because everything takes longer than you think.

If you thought this was going to be an easy piece of cake overnight success, then yeah, if this were kind of hard and you didn't really like it, but you were going to see the light at the end of the tunnel right away, then it might make sense to do. But because everything takes longer than you think, even for something that you are good at and like doing, there are going to be rough parts where you don't really feel like continuing and where you question whether any of this was a good idea at all. So

Wes Kao

leaning into your strengths and doing stuff that comes more naturally to you where you have an edge makes it all a lot more joyous of a process, which means that you are more likely to stick with it long enough to actually see the light at the end of the tongue.

Srini Rao

I appreciate that more than you can possibly imagine because I just, you know, when I see people follow prescriptive advice, they don't consider context. And part of the problem is that almost all our sort of role models are outliers, right? Because they're the people who write books, they're the people who appear on shows like this, you know, they're the ones who are in the covers of magazines. We had Justine Musk here, and probably one of the things that struck me most that she said about Elon, is she said, I don't want to get all deterministic, but I don't think this is something you can learn.

to be like this, to think like this. That's something that is innate. And yet, you see all these articles on sites like Medium, it's like, oh, 10 ways to be like Elon Musk. And it's like, yeah, but you're not a fucking genius, so maybe that's not gonna work for you.

Wes Kao

Yeah, you can do those 10 things and any list of things and not still be hit. I think that that's, that's a, something that struck me a lot when, um, when I was working with Seth, because a lot of people would, um, admire Seth and, and want to imitate him and they would try to write in his style. So, you know, short,

short daily blog posts, right? If you look at what, what does Seth do? Okay, on the surface, he does short daily blog posts. And so a bunch of, of people would start doing short daily blog posts and it wouldn't really work. Like it, it just, it didn't land the same way. And the reason is because the short daily blog posts, right, it's, but, but beyond that, it's, that's the tactical expression of a deeper,

Srini Rao

You're not Seth.

Wes Kao

underlying skill set, principle, personality, et cetera, that is uniquely Seth, that if you just copy the tactic, you don't, you're not replicating the other stuff. The other stuff is the important stuff. And that's the underlying stuff, which is Seth is incredibly insightful. He sees things differently and is able to capture and articulate those insights in a way that feels mind-blowingly

breakthrough, but also weirdly obvious at the same time. Like you read it and you're like, Oh my God, like, of course, why didn't I think of that? Like, that's like the best way to say this thing that I've been feeling all along. Right. He, he's able to distill complex ideas into really simple, impactful concepts. And he's an amazing writer. I think that's the other thing is like, you kind of, you kind of know this. Cause you're like, okay, well he's an author by trade. He's written 18 bestselling books. So you,

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Srini Rao

Yeah.

Srini Rao

Yeah.

Wes Kao

On the surface, you intellectually understand that he's a great writer, but I think when you read his posts, he's so good that you don't think of him as a writer. You think of him as an insightful person. It's kind of like a great salesperson. You don't think like, oh, that person's a great salesperson. You're just sold. You just love them. You just want to buy from them. You just want to move forward. You don't think like, oh, they're so good at sales. So when you read set stuff or any really good writer stuff, you don't think...

Srini Rao

Mm-hmm.

Srini Rao

Mm-hmm.

Wes Kao

Oh, they're a great writer. You just think they're a smart person or they're an insightful person or they're, you know, they're a thought leader or whatever. Um, so I think when people, when people mimic and replicate surface level tactics without understanding the, um, the underlying constraints and assets that the original person is working with, then, then you, that, that's where you get into trouble. I think what you need to do is assess your own assets and constraints.

What do you bring to the table? What are you good at? How do you see things differently? What are the things that are constraints that you wanna work around? Because Seth has constraints also. He's not good at everything. You just don't really know them or see them because he has designed his work around that. And so similarly, we all need to look at ourselves, stop looking so externally, trying to copy other people's service level tactics, and instead look at ourselves and take stock of your own assets and constraints.

Srini Rao

It's funny because like this is literally the ethos of everything that I've built on Mistakeable Random. I mean, my book was called Unmistakable, why only is better than best. And I've always jokingly said we could have also titled that book Everybody is Full of Shit. Penguin probably wouldn't have published it, but that's effectively what I said. I was like, I just said it in a really polite way. Because you point out mimicry and that was what I saw over and over again, right? To this day, and I still see it. I had to...

Wes Kao

Haha

Srini Rao

a friend send me about 13 potential podcast guests. Um, and I remember, you know, and I probably share this in trouble for, I put up all of their websites, you know, in one browser, all tabs, and I looked at all 13 of them and I emailed her in back and I said, I don't want any of these people because I don't know what the hell any of them do and it sounds like they all do the same thing. And I saw this, I saw this in particular with certain groups, uh, Marie

Srini Rao

you know, try to copy her style, you know, her business, and then they wonder why they're not getting the same results. And it's like, um, go, you know, take a deeper dive to, to your point, like they ignore context.

Wes Kao

Mm-hmm. Yeah, great example.

Srini Rao

Yeah. Wow. Well, I feel like I could talk to you all day about this, because clearly you and I are on the same page about a lot of this. This seems like a really deep rabbit hole. So I want to finish with my final question, which is how we finish all of our interviews with the unmistakable creative. What do you think it is that makes somebody or something unmistakable?

Wes Kao

Ooh, what makes someone unmistakable?

I think their ability to turn bugs into features. I think all of us are dealt a certain hand and have certain personality traits a lot of times that we wish were different. You know, I, for example, spent many years wishing I were less introverted and lamenting about how that, you know, wasn't beneficial in the workplace, wasn't seen as a positive thing necessarily as a leader.

Um, and it was really only when I embraced the idea of turning bugs into features that I thought about how a lot of the reasons I've been successful is because of my more reflective nature, my self-awareness, my, um, my instinct to think about something, um, and want to, want to process it instead of just, you know, blurting something out. And, uh, this applies to products too. You know, I think a lot of times we,

we have a product and we think, Oh, I wish this were different. Or I wish this were better or, you know, they didn't have this or, you know, this product is too complicated or this product is too simple. But if you turn a bug into a feature, there are people who are looking for a solution that is very simple. There are people also looking for a solution that is more complex, more robust, more customizable. So, you know, I see this as something that, that I apply, you know, to myself as a person, but also to any product that I'm

responsible for selling for marketing. And this idea of turning a bug into a feature, I think is something that can really take every leader to the next level.

Srini Rao

Amazing. Well, I can't thank you enough for taking the time to join us and share your insights and wisdom with our listeners. Where can people find out more about you, your work, and everything that you're up to?

Wes Kao

I have a website at wesko.com and a newsletter that I send out every once in a while. I am on Twitter at Wes underscore KO and then Maven is at Maven HQ and Maven.com.

Srini Rao

Amazing, and for everybody listening, we will wrap the show with that.