How to become a world-class entrepreneur in one year

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Scott H Young is an entrepreneur and author of Wall Street Journal best-seller Ultralearning. You can learn more about him or read his free content at his blog, and his book Ultralearning is in bookstores everywhere and on Amazon.

He is most well-known for a couple of things:

  1. Designing and completing “The MIT Challenge”, which involved teaching himself MIT’s undergraduate computer science curriculum in 1 year instead of the standard 4 without taking any classes.
  2. He also did “The Year Without English”, where in 12 months he learned 4 different languages in 4 different countries in complete immersion with little to no training in those languages beforehand.

This episode is a definitive guide on how to develop your entrepreneurial skills: he walks us through the 9 principles of effective learning, and how to apply them to become a world-class entrepreneur.

Transcript below

Mo: Right. Okay, so I just want to start with a brief introduction. Can you explain what your new book, Ultralearning, is about, why you wrote it, and who it’s for?

Scott: Yeah. So Ultralearning is a book that I’ve written about how to teach yourself hard skills. The reason I wrote it is twofold. The first reason is just simply recognizing that the world that we live in is one where hard skills matter. Being able to work with computers, to be able to communicate effectively, to do sophisticated things is increasingly important. I talk about a number of the global trends that are driving this change, but it’s simply not the case that the kind of things that we used to think about learning, where you just go to university and then you’re done. You get a job and you just learn a little bit on the job and you’re done. I don’t think that that’s the world that we live in anymore. The world that we live in is one where you have to constantly be sharpening the saw, so to speak, and constantly improving yourself and increasing your learning.

Scott: The second reason I wrote the book was just because of my own story. Meeting these people that I call ultralearners, people who take on very interesting and aggressive self-directed learning projects to accomplish truly remarkable things. And so for me there was sort of a union between these two ideas, the sort of necessity out in the world to be able to do this, as well as people that most people have never heard of doing just truly incredible things and seeing if they can’t be good exemplars for a process of teaching yourself hard things that you might be able to apply in your own work and in your own life.

Mo: Okay. So one of the books that this book reminds me of is… Actually there are multiple books it reminds me of, like Robert Greene’s book on you know, power and strategy, or Robert Cialdini’s book on influence. I like that there are principles and then there are tactics and stories, and because of those things I’m making a prediction that this book will be one of those timeless books, which is kind of what you were going for.

Scott: Well, I would really hope so. That would be very nice.

Mo: Any other thoughts on that? Did you do this on purpose? Did those books influence you?

Scott: No, I think you bring up a good point. I think this was the challenge in writing a book like this. As I mentioned sort of in my brief introduction, the idea was to find these ultralearners, these people who just accomplish these really unusual and interesting self-directed learning projects like, you know, learning a dozen languages, or creating your own software to win a bunch of money on jeopardy, or building a video game and winning public speaking competitions. All of these stories were really interesting, but the challenge of them is that they’re all just utterly unique. So in some ways, this was sort of my paradox of writing this book is that everyone wants the step by step formula. Everyone wants, “Okay, step one, what do I do? Step two, what do I do?” And then they want this cookie cutter recipe to follow.

Scott: The problem is that, the kind of thesis of this book is, this is trying to do what the step-by-step cookie cutter formulas can’t do. I mean the whole reason I think ultralearning can sometimes have an advantage over formal education is simply because you knowing how to learn and knowing what your goals are can often make sort of idiosyncratic decisions about what you want to learn and how you want to learn it that will suit you in ways that a very generic one size fits all formula will not. My argument is not just that school is inefficient, but that some of the inefficiencies of school are based on the fact that they have to set a curriculum for everyone. Everyone has to go through it at the same pace. Everyone has to have the kind of same criteria and goals at the end of the class. If you are able to modify those, tailor them to what you’re trying to work on, you can be more efficient. But the very sort of same logic also implies that there is no step by step formula, because if there was a step by step formula, that would be what they teach in school, right? Or what they could teach in school.

Scott: And so for me, I was kind of caught in this bind. How do you teach someone to do something that is inherently irreducible to these kinds of step by step formula? And so I liked the idea of principles because principles are sort of what the end point is of what we’re trying to do with this. It’s that, if you really understand these concepts, you should be thinking of them in terms of principles, in terms of this is a general phenomenon about how your mind is able to learn things, how you think about memory, how you think about attention, how you think about understanding, and if you understand these principles then you can align what you’re trying to do to fit with them more closely. Now the disadvantage of a principles-based approach is the same reason that a lot of people do like step-by-step. It’s hard to fully understand principles right off the bat. So my hope for this book was not that you read this book and then all the nine principles just sort of suffuse every aspect of your being and now you never make any mistakes learning again. That’s certainly not the case, but I’m hoping that it will give you that nudge to start an ultralearning project and to start doing your own kind of a self-directed learning, and that it will also give you some tactics. So in addition to the sort of higher level ideas, I tried to break it down into specific ways it manifests. Not only through concrete examples, through the stories that I illustrate, but also through specific tactics so that you could… You know, every principal has maybe four or five different little tactics that you could apply as examples of how that might work in an actual situation.

Scott: I think that when people are reading the book, I’m hoping that they remember some high level gists of the principles, like you know, directness that you don’t want to have to transfer a lot, so you want to learn things in a way that’s connected to the situation and context you want to use it in, or retrieval that if you want to remember something that you better try to actively recall it rather than just review it and look at it. These are sort of high level ideas, but I think, I’m hoping at least, that people who read the book, they implement a little bit, they go back, maybe they read the book again later. They’ll see how much nuance and depth there are to these principles. I’ve tried to sort of hint at that at the book without overwhelming people.

Scott: But for me, I mean I’ve spent the last decade thinking about these things, and having that nuanced pictures of the principles I think is where people are able to get these kinds of really impressive results.

Mo: Could we go ahead and give people a quick summary of each principle, just to share the context a little bit?

Scott: Sure.

Mo: Number one, meta learning.

Scott: Yeah. So meta learning is the idea that, and this is particularly important for a self directed learning project. Important for all learning, but particularly for a project that you’re undertaking is that, before you start learning something, you should learn how to learn it. So this has two manifestations. One is in the short term, you ought to do some research to figure out what’s the default way people learn it? What are the kinds of things that you’re going to have to encounter? What are the obstacles? And this already should get your gears moving as to what is going to be the challenge? What am I going to have to do? What am I going to have to focus on? That’s very important.

Scott: Then there’s the longterm meta learning, which is sort of as you develop more experience with learning in general, you get this kind of broader picture. So in some ways, this book is to try to give you that first step in the longterm meta learning direction so that these principles which I’m outlining will be something that you kind of understand at an intuitive level. Similarly to how, if you are a physics student and I was talking about conservation of energy, you might be like, “Oh yeah, that’s an important thing.” But if you were a physicist, you’d realize how that simple constraint solves a lot of physics problems. I’m hoping in the same way, the longterm picture is that, as you do more projects, as you see how these principles manifest in different places, you will start to be able to apply them more rigorously and start to spot, “Oh, this is why this isn’t working because it violates this principle or because it’s got this problem.”

Mo: Number two, focus.

Scott: Focus is the idea that, in order to do learning, you need to have concentrated bursts of attention. I think this is not really the surprising thing, so in some ways that sounds kind of obvious when you say it, but one of the things that I recognize deeply when I started researching the book is that the problem is that we have a lot of emotional reactions to learning, and then that causes us to procrastinate. It causes us to get distracted. It causes our well-made plans to fall apart when you have to do something difficult. So a lot of focus for me in this chapter was to really look at, first of all, how do you deal with the fact that none of us have a perfect schedule or environment, so how do you deal with the fact that there are going to be distractions, there are going to be other things in your life that are going to make it hard to focus on learning for a long period of time? And then also how do you deal with the fact that a lot of learning well is somewhat difficult? It’s somewhat cognitively demanding, and it’s a lot easier to just watch television or surf Twitter and Instagram. How do you deal with the fact that those things are easier and you are going to naturally be drawn to it? How do you create systems in your life so that those things are just something that you can actually make progress on with the learning projects you have?

Mo: Number three, directness.

Scott: The idea behind directness is based on this broad literature that stretches back really over 100 years on transfer. The basic idea is that we have known for some time that students are not that good at transferring things from let’s say what they learn in a classroom to real life. This has really perplexed a lot of researchers that, some of the examples that I cite in there is that in one study, I think it was economics majors did not do better on questions of economic reasoning than non economics majors. In another study, students who had taken a high school psychology class do not do better on college level psychology. So these are pretty basic things that you would expect to be able to transfer, and yet they don’t occur.

Scott: The idea here is that there’s all sorts of ways that our learning projects can fail because the actual thing we’re doing when we’re practicing doesn’t really resemble the thing we want to do when we’re actually using the skill, so there is a lot of transfer. Because there requires a lot of transfer, we often fail at learning those things, or we learn them much less efficiently. The idea here is simply, if you want to learn things well, you ought to learn in a situation that is connected to the context you eventually want to use it.

Mo: Number four drill.

Scott: Drill is based on this idea that, if you want to improve things, often the skills that we’re practicing are really complicated. There’s lots of different elements and aspects of it that all have to be managed simultaneously, and so drill has to two parts. One is that we want to focus on the things that we’re weakest at within a skill that we’re practicing. This is often because those weaknesses are the things that hold us back. Second, that the problem with improving skills just through direct practice, not through any kind of specialized drill, is that often there’s too much going on so it’s hard to get better at any one particular aspect. This is really the whole idea behind deliberate practice, but setting drills and actually isolating components of your skill to improve that is an essential part of learning.

Mo: Number five, retrieval.

Scott: Retrieval is a very interesting set of ideas. There’s a lot of interesting research done by Jeffrey Karpicke, I think at Purdue University, and he has just really done a lot of research showing that if you want to understand something, if you want to be able to remember it, you’re much better off trying to retrieve the information actively than to review it passively. There’s all sorts of studies that show not only that this kind of active recall is more effective, but that students often feel the opposite way so that when they do passive review, they feel like they’re learning it better than they do when they’re doing retrieval. So this is really a kind of counterintuitive principle that leads many people astray.

Mo: Number six, feedback.

Scott: Feedback is obviously essential for learning. You need to get feedback in order to be able to adjust your performance, to be able to learn from your mistakes. The feedback literature, however, is super nuanced and has super interesting details because sometimes feedback helps, but sometimes it doesn’t. In particular, I think a lot of times it doesn’t is because, it’s knowing how to use feedback correctly that’s super important. There’s a lot of different aspects of this that I discuss in that chapter, and particularly for adjusting the difficulty, for learning to tune out types of feedback that aren’t very helpful, or even just recognizing what kind of feedback is possible from a situation, because sometimes it can backfire if you try to get feedback that doesn’t actually drive your performance. At the high level, feedback is super important, but definitely being able to use feedback effectively is an important part of learning.

Mo: Number seven, retention.

Scott: Forgetting is part of human life. It is just part of how our brains work. In order to learn well therefore, dealing with the fact that you’re forgetting things constantly is a major, major problem. We’ve already talked about how retrieval can help with longterm memory, but there’s also some specific findings on not only why we forget things, which can influence how we practice, but also what are some things that we know are helpful for preventing forgetting. Things like spacing, things like proceduralization, and then of course there’s all the specialized what are called ultralearner tools, which have their little subcultures of enthusiasts of space repetition systems and visual and spatial pneumonics and things like that.

Mo: Number eight, intuition.

Scott: Intuition is basically the idea of, first of all, how do you develop a deep understanding of things? And then second, how do people seem to have really deep intuitions that allow them to do almost kind of magical feats of intellect with those subjects? I discuss not only the research on chunking and about how our brains sort of build up experience within an area so that you can make intuitive judgments of reasoning, but at the same time, how do you deal with the fact that you don’t understand things intuitively? How do you get to a point where something that seems confusing feels obvious?

Mo: And number nine, experimentation.

Scott: Well, experimentation is really the summary of the entire philosophy of the book. Like I mentioned before, the challenge of writing a book like this is simply that there is no cookie cutter formula. There is no step by step, and so it’s very important to adopt this mindset of experimentation because all I can give are kind of starting points and hypotheses that might help you. When you actually learn something, the complexities are so much that you do have to do a lot of figuring things out. You have some good starting points, “Okay, maybe this will work,” and then you try and then you find out maybe it fails for some reason you didn’t expect, and then you have to try something else.

Scott: In particular, this experimentation is the last principle because I really feel that the further you go into skills, you approach not just learning the basics of something but really truly mastery, then experimentation becomes extremely important because when we’re dealing with a lot of skills, it’s not just performance that we’re looking at, but we’re also looking at originality and creativity, and those things are intrinsically tied up with experimentation. So when we’re dealing with things like, you know, how do you become a great painter or writer or entrepreneur, these things involve being able to see things, do things in a way that other people cannot or have never done before. That kind of exploration is a very important part of learning, which may not be present in the early or more academic stages of learning.

Mo: So those are the nine principles. Now, you tweeted a while back about certain books that really should be blog posts. This one is very much not that, because I don’t think you could have captured all of these nine principles with the concrete examples and stories of these principles in action, and I think it would be difficult for most people to imagine what the application looks like in practice.

Scott: Well, and I think you’re right. Just, even this summary I think does not do things justice, but part of that is just because, not to sound too immodest, but this is a book that I’ve thought about for 10 years, and I mean, in each chapter I cite a few studies. My goal wasn’t to, “Okay, here’s every single study that’s ever been done on this topic.” I wasn’t trying to write a textbook. But in the same sense, I did read way, way more studies and actually made it into the book, and there are a lot of places where I talk about something for a paragraph, but there was a lot of thought that went into it. So I’m hoping that, you know, this is a book that does benefit from more than one reading.

Scott: For instance, if you read it once and then you try a project, then you go back again, because I have spent my life really trying to not only understand the science of learning, but trying to implement it in practice and seeing all the little details that come that way. Yes, I think some books… We won’t name any names, but some books definitely are just an elaboration on a single idea, whereas for me, this book was how do I take the million ideas that I have about learning and put them in a comprehensible and readable format for someone who they can make sense of it? You know, we were even talking about this before we started the recording that I’ve written over 1300 articles. Many, many of them have been about learning, or at least learning adjacent, and so this book was also an attempt, at least on my part, to take a lot of diverse ideas and bring them into the fold so that they are in this kind of comprehensible structure.

Mo: Okay. So I’ve got this question that’s basically a thought experiment, and it’s basically going to boil down to how can I best learn how to build a startup? But before that, you often hear that entrepreneurship can’t be taught. Why do you think people think that and what are your thoughts on that?

Scott: I think entrepreneurship is often not taught very well, but that’s not really too surprising. I think a lot of skills are not taught very well, and I think a lot of that owes to, not the inability to teach, but just that the structures of our educational institutions often make the environments that are truly useful for learning difficult. So the structure tends to be a lecture format, one to many, where students sit in a classroom and listen. And even if there’s deviations on that, this tends to be the main theme that we do for education. Whereas the model of learning that I would say is closer to how we are designed to learn is more like apprenticeship.

Scott: In this sense, if we’re talking about a master and apprentice type relationship, I do think entrepreneurship can be taught. It can be taught the same way that, blacksmithing and sports and other things are taught, in that if someone were, working on a startup, actually trying to create their own business, and then there was someone who had a lot of experience who was giving them advice and pointing them in the right direction, I do think that there can be valuable lessons there. I do think that some of the challenge of entrepreneurship is the same challenge of learning a lot of real world skills, that there is a huge gulf between the abstract principles and the implementation in reality.

Scott: What that means is that teachers in schools obviously want to teach abstract principles in the same way that I wanted to write about abstract principles in this book, because it’s impossible to write about all the details because the details vary from situation to situation, right? So if you’re teaching the class or you’re teaching something like this, you can teach these principles, but if those principles aren’t combined with some kind of practice, if you don’t actually go out and do something, you have nothing to connect it to, nothing to ground it down to. And so I think that, just the same way that my book… You’re not going to understand ultralearning just by reading this book. You’re going to understand it by reading this book, and then doing your own project, and then maybe reading some of the book again or something like that.

Scott: In the same way, education programs that look more like apprenticeship, I think are more likely to teach real world skills because the students are encountering real problems and then they’re seeing, “Oh, this is an application of this principle. This is where you’re going awry with your startup.” I definitely don’t think it’s the case that entrepreneurship cannot be taught, but it’s definitely something that, if you’re only picking up a textbook and sitting in a classroom for 40 hours, you’re not gonna learn it very well. But that’s not just true of entrepreneurship. That’s true of most skills.

Mo: Yeah. Another tweet that you had was talking about learning something specific to learn about the general. In the spirit of that, I’ve created a character as a guinea pig for this thought experiment, and I think the principals will generalize.

Scott: Okay, sure.

Mo: So here’s the scenario. Let’s say I’m in my final year of college, studying something in the social sciences. I’ve done one internship and a research assistant job with a professor. I’ve done some clubs at school. I have no student loans and enough savings to last me one year after college without paid work. I want to learn how to be a great non-technical co-founder of a tech startup. You know, something like Slack or Shopify.

Scott: Yeah.

Mo: So all the business side stuff, no coding. The goal is not necessarily to make a startup, my first startup, succeed. It’s to learn how to be a great entrepreneur in one year. Let’s say this is an extended learning sabbatical, something like the MIT Project or the Year of No English. How might I design that program while implementing some of these principles?

Scott: Well, the starting point is do the startup, right? I know that sounds like that’s a super obvious thing, but that would be the thing to start with is to do the startup. Now, the thing that happens when people are doing start… First of all the startup environment itself is… The reason I’m saying this is because one of the principles we talked about is directness. The main reason you have to not do it this way is when it’s not possible to do that. So for instance, if you wanted to be a doctor, well you’re not gonna be able to do surgery on someone if you have no experience. So you can’t learn directly, therefore you have to think of “How do I practice this in a way that it will transfer later?” But if we’re talking about doing a startup and you want to do your own company, well anyone can do that. If you’ve got a year’s worth of savings, do the startup. That would be the starting point.

Scott: What the rest of the book and the rest of the ideas I talk about in Ultralearning are going to come in is is going to be using your own experience of starting the startup to identify what are your specific weaknesses. This is not going to be a generic curriculum of, “Okay, well you’re going to do a startup, but then you’re also going to have to read these 50 books. It’s going to be recognizing, as you’re starting a startup, what are the things I’m not good at? What are the things that I don’t understand, that I need to get up to speed on?” And I mean if you’re starting a startup, there’s going to be many of those things. Then it’s going to be, “Okay, how do I get a curriculum to acquire these skills in the way that will allow me to do well in this program as well with launching my business?

Scott: So you might need to do a crash course on entrepreneurial finance, right? Maybe you don’t have a business background and you don’t know anything about convertible debt and net present value calculations and all these kinds of things. Okay, So let’s do like a super, let’s get up to speed on that, right? Or maybe it’s, let’s get up to speed on copywriting because I’m the one who’s in charge of marketing and I have to not only write emails and pitch people on this, but I also have to convince customers to sign up or people to join our program and write sales pages and landing pages and stuff. Or maybe it’s design. Maybe you have to think about the aesthetics, especially if you’re doing consumer-based stuff. That’s going to be a big thing about whether people find what you’re doing appealing. And there’s all sorts of things like this, but it’s not going to be coming from a curriculum.

Scott: It’s going to be driven from your project. So while you’re starting this startup, you’re going to be identifying deficits, identifying things that you need to get better, and doing little projects to get better at it. For me, that’s the right way of thinking about it. We can talk about more scaffolding for that, like I think mentors are very important as we were just talking about, the master apprentice relationship is very valuable in this kind of context. But my idea is that if you were to do a year long kind of sabbatical and you’re not doing a startup, there should be a very good reason why you’re not doing this startup, because that would be the best way to learn it.

Mo: Okay. So the most important thing is to actually work on the startup. What about meta learning? How would you go about building a map to learn how to learn this stuff?

Scott: Well, yeah, the first thing is to interview other successful founders, maybe, you know, we’re talking right now about it. You know, this is for your incubators. That’s a good reason to have incubators. Talk to other people who have run companies, not just people have succeed, but people who failed and try to deduce sort of what are the things that matter, what are the things that they got good at, what skills were important, which ones didn’t matter, right? You will get a lot of different people talking about different things, so you’re not always going to get the same map from every single person, but it will give you a generalized sense of these are themes that come up and recur. So that expert interview method is going to be very important.

Scott: I think also at the same time, you’re going to be wanting to look at doing this, a version of this process, for the sub-skills that you identified. So as I mentioned, running a startup is not one skill, it’s 1000 skills. And so to get better at each of those individual skills is it self kind of a mini ultralearning project. In some ways that would be the way I would tackle it is, don’t think of starting a startup is one ultralearning project. Think of it as a series of different ultralearning projects where you are working on the startup, but at the same time acquiring adjacent skills that are going to be helpful for that.

Scott: As I mentioned, entrepreneurial finance, copywriting, marketing, maybe how do I make contacts and meet people and give a good first impression and stuff? So there’s even these sort of soft skills that are important. Even if you’re not a technical co-founder, you certainly should understand the technology you’re selling, right? So that requires a level of understanding that, even if you’re not doing the programming, it shouldn’t be like, “Oh, that’s for the tech people. I don’t understand any of that stuff.” And so I think that that’s a huge part of it.

Mo: How about focus?

Scott: I mean you’ve got a year off, so it’s time to actually set your schedule and work on this startup. I think again, you’re going to have to balance things, because there’s going to be the work on the startup and then there’s the work learning the things that you need to do this startup. There is going to be quite a bit of overlap there, so you can learn copywriting by trying to write the sales page for your actual startup. You can learn finance by trying to work through the actual valuation assessment of your company or creating that financial model in the business plan. You can work through these through examples.

Scott: It’s not that the learning projects that you do to learn sub aspects of it have to be separate, but you might still have to read a book or you might still have to go through a tutorial, work through some exercises before you really understand how a net present value calculation works or what is a risk adjusted rate of return or you know, what, what, what are, you know, investors expecting in terms of valuation stuff? Playing around with that so that you, you understand how those work.

Scott: And so for me, I think again, just given this context that we’re talking about, you’re going to be doing this full time, you’re going to be working hard on it. There’s a lot of stuff about the kind of startup hustle, so I’ll let you decide exactly what schedule you want to do. I think for me as well, a lot of the putting in the effort in a startup is how can you avoid procrastination, how can you avoid distraction, and how can you make sure that you’re working on the right things? Because again, a big thing when it comes to doing something like a startup is not really just the choice of I’m going to spend time on this because most people who do a startup I think work on it pretty hard, but rather that I’m also going to be making sure that I’m not doing things that are superfluous or that are not really relevant to getting good at this.

Mo: You’ve already touched on directness and drill for this example, so I think we can go to retrieval. How would that apply?

Scott: Well, retrieval again, I think when we’re talking about retrieval, retrieval is something that I think is more relevant to academically learn subjects. For this particular context, I think if we could focus on directness, then retrieval will probably take care of itself as a principle. I don’t think it’s going to be highly, highly important. The one area that it might be important, and this is again, it’s just sort of a helping point, I don’t want to say it’s a necessary thing, but would be that a lot of people who are entrepreneurs, you’re going to be doing reading. Retrieval really comes into play whenever you’re doing any kind of reading or passive review of something. And so if you are doing some reading, and it could be again for learning one of these sub-skills, maybe you’ve read a few business books, maybe you’re reading a few textbooks that are giving you some kind of technical information, and if you are just encountering ideas so it will be some idea about something, well then the first thing would be to try to apply it.

Scott: That would be the first way to practice this kind of retrieval is apply it immediately. But there are maybe going to be ideas that you don’t use immediately, so it will be some sort of concept that might be useful but I’m not using it immediately. For those kinds of ideas, I think practicing retrieval would mean something like when you read a book, after you finish a chapter, close the book and see what you can recall from that chapter. And then maybe if a book you thought was really important, maybe like a week after you’ve read it, try to see if you can summarize the main points. These are things that I think generally fit into the strategy of learning from reading or learning from lectures. To the extent that you are learning from those channels while you’re doing your startup project, I think retrieval will be relevant.

Mo: How about feedback? And maybe we can tie this into the apprenticeship model or the mentorship you were talking about earlier.

Scott: If you’re actually doing the startup, you’re going to be getting feedback all the time. I think there’s two mistakes that can be made with feedback here. The first is to not get enough feedback. The classic mistake that new entrepreneurs make is, they don’t tell people about their idea because they’re worried someone’s going to steal it. No one wants to steal your idea. First of all, if it’s any good at all, someone’s already got it. No one ever has an original idea. No one’s like, “Oh no one has ever heard of this idea before when it comes to X.” I’m sure at any good company, there’s at least two or three people working on that idea already. So first of all, you don’t have to worry about that because someone else is already working on your idea.

Scott: But then also, it’s important to get that feedback from people of, a lot of times you can get this idea of, “Oh, well I think people would want this,” and then you don’t actually talk to your target market, right? You don’t actually talk to people and really get that visceral feedback of do they need this? Because if the answer is, “Oh, maybe, maybe I’d use that,” you know, you can make a product no one wants. And this is not just true of startups. This is true of any kind of business. That kind of feedback from the market is very important. That being said, the other problem with feedback is expecting a level of granularity that doesn’t actually exist. This is something I talk about in the book where I talk about the three types of feedback of outcome, informational, and corrective feedback that a lot of people, who are starting a business, particularly if they haven’t been around the block a few times, they’ll ask customers, well what do you think of my app interface? 

Scott: And then the customer will say all sorts of suggestions, and they take these very seriously. And then they implement those suggestions. It’s not to say that that can never be helpful, but the problem is that customers don’t know what they want. The problem is that customers get an intuitive feeling from using your application, and then when you ask them what they don’t like about it, or what they could do to improve it, they now have to confabulate some reasons to support this intuitive reasoning. And the problem is that even though the intuitive reasoning is probably pretty accurate, those reasons may not be.

Scott: And so anyone who’s designing a product needs to be wary that they can get feedback from customers, but they may not be able to get the kind of feedback that they would like to get. And so to get corrective feedback, you can have a mentor, so if you have a good investor, a VC or someone who has a lot of experience, they can offer some feedback. But even then you have to take into account that people have limited experiences, and so it may not be that they’re providing the right answer for any one of your problems. And so you have to be wary about overreacting to some of the details of feedback, even if at the same time you’re pursuing the general high level signal of do people like this or not?

Mo: And in terms of retention, would it just be about continuing to apply some of these skills? And continuing to retrieve if it’s book information?

Scott: Yeah. Retention I don’t think is going to be as relevant for a startup because we’re in a situation where that’s going to probably get taken care of itself. If there’s something you need to remember, you’re probably going to remember it while you’re doing this startup. Retention I think is a more important skill in two situations. One, when the subject itself is highly memory intensive. Languages, anatomy, medicine, law, these are all situations that as soon as you start learning it, you start forgetting it. So that’s one of the problems. And then the second reason that retention is valuable is when it’s not a skill that you actively use all the time. Because skills that you actively use all the time, in which case startups would definitely be one of them, you’re not going to forget that skill because you’re always using it. So you’re kind of always practicing spacing. You’re always practicing the ideas of that principle. So I don’t think retention would necessarily be all that relevant. Again, it goes back to the same idea of retrieval. If we’re talking about how you’re doing a lot of book learning for some aspect of the skill, then this is going to be relevant. But for me, just off the top of my head, I can’t think of a good example of that. But depends on what your startup is, startups are such a broad territory. If you were doing a startup that’s based on something which requires a lot of memory, maybe that’s going to be relevant.

Mo: And in terms of intuition, is it just a matter of solving a lot of problems that come up?

Scott: So I think again, intuition, there’s two ideas here. One is just a descriptive process of how we actually acquire understanding and things. And so I’m a big fan of this chunking model, which is that the way that we develop an intuition or understanding is through large volumes of experience where we basically learn patterns. And this is a descriptive thing, not really a prescriptive thing. So it’s not like I’m saying, “Oh, you ought to go out and chunk things.” I’m just saying that this is how your brain already works. But it’s important to keep this picture of your brain in mind because when you see someone who is doing something really well, that they really understand a lot of concepts, I think it’s better to, instead of saying, “Oh wow, that person must be so smart,” which they may be. I think it’s more useful often to say, ‘Ah, that person has a lot of patterns that they’ve learned that I haven’t yet.” And I think that’s often more useful.

Scott: The second part of intuition is really how do you understand hard things. So I talk about the Feynman technique in the book. And although I do find this is useful for subjects that are inherently confusing, it can often be useful for aspects of business problems or things that you find difficult to understand, or wrap your head around. So we’re just talking about entrepreneurial finance. These are not easy subjects, right? To be able to properly do a net present value, to be able to properly understand the difference between assets and liabilities on a balance sheet, or the various types of equity, and how does an IPO work? These are technical subjects. So in this sense, the Feynman technique, if you don’t understand how these things work, it can often be useful.

Scott: Is this going to be the main thing that you use to solve your starting problem? Probably not, because most of the situations I think are an issue of, not that you have no idea how a concept works, but you just are trying to implement it effectively.

Mo: And the final one, experimentation.

Scott: Well, obviously startups are all about pivots and trying things. That didn’t work, let’s do something else, and working things in there. So I think the experimental mindset and the entrepreneurial mindset are practically synonymous, especially when we’re talking about startups. So I don’t think anyone reading that chapter would be necessarily surprised. But I think there’s a few kind of sub ideas within there that may be useful. So one idea that I think is useful is the idea of thinking in terms of what you’re trying to accomplish when we’re dealing with mastering creative skills, as exploring a higher dimensional space. And so, that sounds needlessly abstract. So in some ways I’m hoping that there are going to be some readers that they get what I’m talking about, and it doesn’t just sound super confusing.

Scott: Basically when we are dealing with getting better at anything, often what we’re doing is trying to find some optimal point, right? And it’s easy to imagine that in let’s say a two dimensional situation where you have the ground surface, and maybe you’re trying to find the highest peak of a mountain. And so this is sort of an exploration problem because maybe you’re trying to find the highest peak of a mountain, but you’re blind, you can’t actually see anything. So you just are trying to walk up hill at all times, right? And you’re hoping you’re getting to the the highest peak of the mountain.

Scott: Now the real world is a lot more than just two aspects of the things that we’re working on. So when we’re dealing with entrepreneurship, there’s pricing, there’s capitalization, there’s all sorts of these little different variables. And they’re not entirely independent, but they’re also something that we’re often trying to explore when we are creating products and services that work. That we’re not just trying to create something that’s optimal, we’re trying to create something that’s original. We’re trying to create something that is new and varies in ways that other people don’t expect. And so, I think there’s aspect of exploration can be quite valuable, because it often suggests things like, for instance, that pursuing the extremes of things is often more valuable than just picking the middle, simply because it allows you to explore more of the space of possibilities.

Mo: If you could recommend a handful of books related to business or entrepreneurship that have generalizable principles, what would they be?

Scott: Oh boy. You know what? I think I’m going to pass on that question. I’m going to kick it down the road a little bit just because I think, the way you want to think about learning business through business books is, well first of all, what we just talked about learning through practice. But then the other thing is that it’s not about reading one book, it’s about reading 50 to 100 books. And I think if you get that mindset, then that’s a lot more valuable because a lot of people say, well what’s the one book I should read? And it’s really hard to pick the one book, because most books are just one idea. Or if they have multiple ideas, they’re one perspective on those ideas. And so I think the right way to think about books, even including the one I’m listing right now, is to get many, many, many, many of these perspectives.

Scott: And so, instead of thinking about, okay, what is the three or four books of principles that I should have for business? You should be thinking, how do I get in the habit of reading books so that I’m reading 20 or 30 books a year, and thus building my library of ideas that I can use to apply to problems.

Mo: Do you think it’s a good approach to go out and get a book that would help you solve a problem that you’re facing right now?

Scott: Of course. Yeah, of course. If you don’t understand entrepreneurial finance, yeah, pick up a book on entrepreneurial finance. If you don’t understand… Okay, I don’t really understand how I should be marketing my business. There’s probably 30 books on marketing you could get. So I think definitely getting a book is a good way to try to get ideas to solve your problems. And I think you want to be in an idea rich environment. So I’ve talked a little bit about how I think books without application or without this directness often fails, but I don’t believe the opposite that therefore you shouldn’t read books. I think that you should read a lot of books, but you need to do them while you’re actually doing the thing you’re trying to get better at. And so it’s the combination of the two.

Scott: So I don’t want to be misled as saying, well, books, there’s nothing worth learning for books. I think that, otherwise I wouldn’t have written this book, right? I think this book, the reason for writing it was, my hope is that some people are going to read the book and then reflect on it while they’re working through their own learning challenges. And again, if you just read this book and then you just have these nine principles, maybe if I’m lucky, you remember like five of the nine principles. If you remember these five principles, but you’ve never actually tried to work on learning a new skill or learning a new subject and applying them, it’s kind of inert knowledge, I don’t think it’s going to help you that much. But if you get this book and it encourages you to learn some skill that you thought might be too difficult before, and then while you’re learning it, you’re like, oh yeah, what was Scott saying about this and this. That’s I think how you’re really going to internalize a lot of these ideas.

Mo: So you’ve been learning entrepreneurship for over a decade now. Do you have any interesting stories about learning challenges you’ve faced and how you kind of dealt with them?

Scott: Well, first off I’ll say that I’ve been a lifestyle entrepreneur in the sense that, I have a company that has a couple of people, even though I’ve been doing it for 13 years. And we make money but… So a lot of these things when we’re talking about entrepreneurship, it’s the question of what type of entrepreneurship. I think people incorrectly conflate startup style entrepreneurship and the kind of entrepreneurship I do often. And so I think that there are transferrable lessons, especially on the areas of marketing. And certainly on the basics of accounting and finance and profit margins and things like this. But just the strategies are so different that there’s a lot of aspects of venture capital financed entrepreneurship that I know about, from not only going to school and studying it, but also from interacting with people who have done startups. But that’s not the same as saying that I know how to do it and I have the right intuitions about it.

Scott: So for me, some of the things that I would say that I’ve made… Well maybe give me an example of some of the types of stories you’re looking for. Because I’m thinking back over 13 years and this could go on all day if I want to just list random things.

Mo: Oh yeah, that’s a good point. Let’s say you did the zero to launch program, right? With Ramit Sethi?

Scott: Yeah, I got his course a while ago. For me, getting the course, it was a little inside baseball, but like my business is selling courses and so for me, I think I wasn’t zero when I was taking that course. I had already had a six figure online business. So a lot of the ideas of the program itself, I’m like, I could see how this would be relevant to someone starting, but they were not new ideas to me.

Scott: For me, the thing about zero to launch that I found interesting was that this is a course that Ramit’s making tens of millions of dollars from. Let’s see how he sells and delivers a course, right? Let’s see how he sells a course that he regularly charges people a few thousand dollars for. And so that was very instructive for me. And I did learn some new ideas from it, so I don’t want to say that it was purely kind of a meta learning exercise. But I think for me, that was a big part of getting this thing was, how does he teach and deliver these courses? And what is the approach he takes?

Mo: Well, I think there’s something to be explored there. Do you remember your inner monologue when you were studying someone else’s business?

Scott: I’m always studying other people’s businesses. So that’s everything I’m doing. I think that’s how I mostly learn how to run my business is studying other people’s businesses. Because books and ideas, once you have some groundings on the basics, that’s the thing that I talk about in the chapter on experimentation, is that as you get better in a skill, it’s much harder to find mass market learning resources because they’re all aimed at beginners. If we’re talking about how to start a business, everything is how to start a business. It’s not really like how do you build a successful business, because we’re now orders of magnitude fewer people when we get to that level. And not only is it orders of magnitude fewer people, but the breadth of knowledge and skills at that level is broader.

Scott: So the best example is learning a language, and it’s entirely analogous here, is that if you want to learn the basics of Chinese, for instance, the hundred most frequent characters or the a hundred most frequent characters, the same 50 to 100 phrases are probably going to be dominating most beginner resources. And so it’s easy to create learning materials for this because again, 100 things is something that an educator can wrap their head around, or a curriculum designer can wrap their head around.

Scott: And also the total addressable market is large. You have a huge amount of customers that don’t know any Mandarin and they want to learn the basics. Now, if you wanted to teach Mandarin to someone like me, I probably already know tens of thousands of words. I probably know lots of phrases. So the next level for me is probably on the order of magnitude is more like 50 to a hundred thousand words, concepts, phrases, et cetera. And so it’s much, much harder to make learning resources. It’s much, much harder to make something that knows what I already know and gives me exactly what I need to learn.

Scott: So it’s going to be a lot more slop dash, so it’s going to be harder to do that. And then also there’s far fewer people like me who are at this level of speaking Chinese. So if you’re making a course, unless you charge an enormous price for it, which I probably won’t pay, it’s really hard to attract those kinds of clients. And so the best you can do when you’re reading books is that you’ll read a book and 90% of it will feel familiar to you, but there’ll be a few ideas that you feel are new. And that will still be worth it at the mastery level, but it’s certainly not the level of every single idea in this book is totally new for me.

Scott: And so I do think at the mastery level, what you’re often doing is studying from exemplars. You’re studying from things that are not really learning resources per se. So for me, when I’m trying to grow my business, I am looking at people like Ramit who have, they’re like the two to three steps ahead business of mine. Like they’re doing a business, but they’re doing it at a bigger scale and in a more sophisticated way. Or as a writer, when I was writing this book, I was looking at James Clear. I was looking at Cal Newport. I was looking at Malcolm Gladwell. I was looking at people who are better writers than I am.

Scott: And entrepreneurship, even my blog, like I find a handful of blogs that I really like how they’re doing things, and I’m sort of figuring out, okay what are the things that they’re doing that I like? And what are the things that I can bring on to what I’m doing in my own work or my own business?

Mo: Could you talk about your frustrations maybe with business school?? Because I think you went to business school and I wonder what your experience was there?

Scott: So the first problem with business school is that you are doing it full time, and often at a point in your life, I’m talking about an undergraduate in business, not necessarily an MBA. But you’re doing it in a point in your life where you have no real work experience or business experience period. So you have no real obvious direct way to apply the things that you’re learning. And you’re doing a ton of full time learning at the same time. So that already is a major violation of the kinds of principles that I’m talking about. That you’re going to forget a lot of stuff in the interim without ever having applied it. So even if you do remember it, it’s often inert.

Scott: The second problem is that the stuff that you learn, the way you learn it in school, is not particularly relevant to actual practice. So for instance they often, I remember doing organizational behavior, organization theory, HR. And they grade you with multiple choice test questions. Life is never a multiple choice. You’re never doing that in real life. So why test you that way? And so I think that the reason that people test this way, the reason educators test this way, is twofold. One, it’s really easy to make a multiple choice test. So it’s really hard to make a real situation where you’re practicing HR knowledge. So there is a certain laziness on the part of institutions and educators, which I don’t entirely blame them for. And then the second problem that you have is that… The second problem you have with this sort of approach of doing it with multiple choice is that multiple choice is really easy to grade and rank people. And so I think another failure of education is that a lot of people think that the primary goal of educational institutions is learning.

Scott: And I’ve really become convinced over the last several years, particularly Brian Kaplan’s excellent book the case against education, that education as an institution is mostly about signaling. And if it’s mostly about signaling, it means that teaching people useful things is not the primary function of school. The primary function of school is to filter and rank people. And if you look at it in this light, it makes sense why they do multiple choice tests. It’s really easy to filter and rank people on how much they learned the material. It doesn’t mean that there’s a lot of validity in that multiple choice tests. It doesn’t mean that if you scored 90% on an HR test, you’re going to be a great human resources manager. No, but it does mean that we can really easily assign you an A plus or a B or a C.

Scott: Whereas if we are dealing with a real life situation, which is going to be different and idiosyncratic, it’s going to be really hard to compare students’ responses. And so I think business education, they do try to do things that transfer, but I think part of the problem is that there’s a lack of self awareness I think from educational institutions themselves, is that they’re often only implicitly aware that what they’re really trying to do is rank and filter. And when their educational goals… Suddenly if you were to have a class where you couldn’t give students a grade, it would be considered a failure. You have to give them a grade, right? But a lot of the great ways of learning things are going to be really hard to give grades for it.

Scott: So I think a lot of the things that I didn’t like about business education are the things that I don’t like about all education. And I think business school suffers from this more than other subjects because at least other subjects, the discrepancy between the ranking and credentialing function of school, and the educating function of school is smaller. So if we’re talking about like the stuff I did for the MIT challenge, learning math and computer science, there are right answers for a lot of those problems. There is a right answer to a calculus problem. You either know it or you don’t. And so in that sense, it is a little bit easier to, at the same time teach calculus and also very objectively rank and evaluate people’s knowledge of calculus.

Scott: Business problems, even though they do try to make them a little bit more rigorous, in my opinion, are often more like artistic problems. It’s a lot closer to fine arts than a science. And so you get in these classes where either the class is creating ranking in rigor where there isn’t really some, so it’s all just memorize these concepts and see where they apply. Even though that may be isn’t really that related to being successful as a manager. Or you get the opposite. You get these case-based classes where it can be frustrating because they’re trying to apply this rubric to grade it, but it really isn’t gradable in that format. Like I did an administrative policy class, which I remember hating because the teacher was an MBA with an engineering undergrad. And he really wanted to make this grading rubric so that he could kind of encapsulate this is the right way to think about strategy. And it’s bullshit. You can’t grade a strategy case. There’s no way you can say this is A plus for the strategy case. It’s bullshit, you know?

Scott: And so the problem is that he’s kind of caught between these two sort of implicit functions of university. One is to give people objective grades that accurately reflect their competence. And at the same time teach what is an inherently a nebulous skill that is, again, it’s more like painting. It’s more like, oh is this painting an A plus or a B? Well, that’s up to the eye of the beholder, right?

Scott: And so I think this is a real challenge, and I think that there are schools that do this better through a more apprenticeship style approach. But again, to the extent that we want from our educational institutions for them to be filterers and credentialers, they may just have these sort of subtle limitations that prevent them from working in that way. And that’s why I’m also excited about things like Lambda school or other institutions where their end goal is get you a job. And who cares about the grades or who cares about like, let’s get you a job. And I think that might work better for some schools. But I definitely get the feeling from a lot of academic institutions that they don’t want to be that. They don’t want to be a community college. They don’t want to be teaching vocational skills. And so business school is sometimes caught between these two different different forces. And I think it results in the kind of weak educational experience that often students experience.

Mo: So despite those shortcomings, there is still this myth that you have to go to business school to understand business. And that’s like one of the things that most pains me when I come across entrepreneurs who are like, oh, I need to find a business guy with a business background. I can’t do it myself.

Scott: Oh, that’s so dumb.

Mo: What would you say to those people? Because I’m realizing that they wouldn’t get anything out of it anyway, so they’re probably better off just actually learning this stuff by doing it.

Scott: Well, I think there are some use. So we’re talking about business skills. The classes that I really liked in business school were the ones that, as I said, that I’m realizing in retrospect, they fit this model of the credentialing function and the educating function being more aligned. So the classes I really liked were things like financial accounting, managerial accounting, corporate law, corporate finance. These were classes that were, wow, this is super useful because the way that they’re testing you is, oh, if you could perform on these criteria and benchmarks, you can think in terms of cash flows, you can read a P&L statement and this kind of stuff. And these are useful skills.

Scott: So I would suggest that if people are non-business backgrounds, they do learn these classes. So I think that if you go to your community college class and take a class in financial accounting, managerial accounting, corp fi, corporate law, they will benefit you. These are good classes. I think that you could probably read some books on some other business concepts. I like the book idea a little bit more than the classes idea just because I think a lot of the homework in those classes, again, it doesn’t drive the tasks that you’re actually trying to get good at. So I think you may be better off reading a business book about marketing than taking a marketing class. It’s probably useful to learn a marketing textbook just because they may expose you to more concepts than a random marketing book. But that’s just sort of a personal preference. I do feel, you know who I’d really feel bad for are the people who are like me, when I graduated from my business school. That you’re like, oh I got all this education and I’m like quote unquote good at business. And I’m utterly useless at doing most startups.

Scott: There’s this stereotype of like, oh well I’ll do the business stuff and you do the technical stuff, and we’ll split the company 50:50. And we’ll go to the market. And you’re like, the technical guy is the one who’s actually making the product. They’re the one who’s doing all the work. And unless you have some, especially if you’ve just gone to school, the business co-founder is often the one who’s dead weight. It’s way easier to just through running a startup learn a lot of the stuff you learn in business school, than it is to learn, let’s say engineering or programming. It’s going to be a lot harder for people. Again, people who haven’t read my book maybe, who are going to just learn the technical aspects of co-founding.

Scott: Very few people are going to be like, oh well now I’m going to be mastering machine learning in the process of running this startup. But it will be much more likely the opposite that a computer science major will understand how entrepreneurial finance works in the process of starting a company. Or they will understand the principles of marketing.

Scott: I do think that there is a mindset of business that’s harder to teach, that a lot of technical people or people who have kind of, oh I don’t like that business stuff. And so they kind of avoid thinking about business problems. But I don’t know whether school is where you learn that mindset. I think school just attracts people who have that mindset.

Mo: Could you describe immersion and how it might apply to learning entrepreneurial skills?

Scott: Well, immersion at its core is being in an environment where you are constantly engaged in practice, and you have some kind of feedback from this environment that facilitates the growth of skills.

Scott: So again, going into this master apprenticeship analogy, I think that that is the prototypical immersion environment. We tend to think about immersion in terms of languages, but I think languages are just one example of an environment where you’re constantly using and applying this skill. And so I think again, starting a startup is a kind of immersive experience. I think you can get benefits to things like being in an incubator, or being in some kind of entrepreneurial social community, because then you also get the benefits of social learning. So for me for instance, I’m not a startup entrepreneur, I’m just again a lifestyle business. But for me, even just being friends with lots of bloggers, being friends with lots of people who run small businesses, I have enormous advantages in my ability to master these skills than someone who’s an outsider. Because if I’m writing a new book, I talk to people who are New York Times bestselling authors about what they think about my ideas. Most people don’t have access to that.

Scott: Or if I’m trying to run an online courses business, I have friends that make $10 million a year from online courses business. And so when they give me advice, I can be like, “Oh okay, maybe I should do this.” And so I think the extent to which you can get in those communities is very important. And I think that is why we do sometimes see a university to entrepreneurship funnel through certain institutions, like Stanford or MIT or some of these institutions, is because of this ability to go to that prestigious institution, thus leading to the kind of immersive environment that allows this social learning or this type of apprenticeship learning.

Scott: I don’t think it has much to do with the classes, but certainly at those institutions there probably are some good classes. And if they’re paired with an immersive environment, they might be quite valuable. But I think that’s certainly a struggle for lower tier institutions that don’t have that coupling with the business community.

Mo Akif

Mo Akif

The Editor-in-Chief of the McGill Dobson Chronicles. Never having started a lemonade stand as a child and tired of reading blog posts about entrepreneurship without actually doing anything, he was on the verge of giving up and joining a pyramid scheme. Luckily the McGill Dobson Centre decided to adopt him, allowing him to get a closer look at what it takes to build something valuable.