Teaching Entrepreneurship, class one

This semester is the third time I’m teaching a class at Columbia University’s engineering school. It’s called Managing Technological Innovation, but it’s part of the entrepreneurship minor so I’m teaching it as a class on how to start an innovation driven enterprise.

I’m learning a lot. Not least that I don’t really know how to teach. Despite spending most of the past twenty years helping entrepreneurs or starting companies myself, It’s been humbling how much I’ve had to learn so that I could articulate the things I already know from experience. If you can’t teach something, you don’t really know it, it’s true. That’s generally why I write this blog, because explaining my thinking forces me to think things through. Likewise, I’m going to blog my semester, not to explain the things I’m explaining in my class, but to talk about how I’m teaching it, to improve it for next time, to get feedback from others who have taught entrepreneurship, and also to give some food for thought to anyone else who might be teaching entrepreneurship[1].

First, can you teach entrepreneurship? I ask myself that all the time. I had a disturbing revelation after the Spring semester: some of my most entrepreneurial students–from talking to them and seeing what they were doing outside of class–handed in the worst work. It seems that people who are willing to buck the system and do things their own way are, in the classroom, willing to buck the system and do things their own way.

An example: market sizing. One of the things I teach is the importance of sizing your market. This is not just a financial exercise, but an exercise in stepping outside of your own preconceptions, of approaching a problem rationally. It counteracts the tendency to think that just because a problem is important to you, then it’s an important problem. Sometimes it is, sometimes it isn’t. You need to do a bunch of stuff to find out, and market sizing is one of the cheapest, quickest and least painful things in that bunch of stuff.

But some of the most entrepreneurial students would rather go with their gut than listen to me[2]. To paraphrase William Baumol, “if you can teach it, it’s not entrepreneurship.” But there is definitely a rational way to approach exploring the unknown from a business point of view, and that can be taught. I can’t imbue someone with an entrepreneurial personality (or maybe I can, or maybe they can find one themselves at some point) but I can certainly teach entrepreneurial skills. I consider the question of whether or not you can teach entrepreneurship sterile: you can teach people how to be more successful when and if they become entrepreneurs. That is what I hope to do.

The focus of the class is (a) learning what entrepreneurship is, how innovation happens, why it’s important; (b) learning processes, frameworks, and tools to help fledgling entrepreneurs succeed; and (c) convincing the students that entrepreneurship is an available and important option for them, that you don’t have to be Steve Jobs to be an entrepreneur, that even Steve Jobs wasn’t the Steve Jobs of our legends. These are probably important in reverse order.

I teach 2.5 hours, once per week. The first hour is usually someone from the industry coming in to talk with us. I don’t have the speaker talk about something specific (although I try to order the speakers so that where they are most spiky coincides with what I’m lecturing about on that day). The second hour and a half is me talking about a specific topic with the students.

I’ve used a bunch of different texts over the semesters. Ries’ The Lean Startup, Blank’s Startup Owner’s Handbook, and Livingston’s Founders at Work all came and went. This semester I’m using Christensen’s The Innovator’s Dilemma, Croll and Yoskowitz’s Lean Analytics, and Osterwalder’s Business Model Generation. I have reasons for dropping the books I’ve dropped (Christensen is the only one I’ve kept all three semesters) and I’m constantly reevaluating. I also assign a bunch of reading each class from the internet.

I am ambivalent about grading. I took a course with Deming in business school. His theory was that all it took for people to do a good job was the opportunity to do a good job. For his class, if you wrote the paper he assigned, you got an A; if you didn’t, you didn’t. Without having to think about the grade, I spent more time learning about a subject I actually found interesting. I think that was one of my better papers[3]. On the other hand, my students are busy, very busy. If something isn’t graded, it gets deprioritized (i.e. it isn’t done[4].) Not sure how to square that circle. For the grade in this class, the students have to form groups that come up with a startup idea and use the things we learn in class to develop it over the semester. Each group then presents to the class and submits a write-up of their work. Each student also has to critique one of the other groups’ idea and presentation.

I know my way of grading is less than perfect. I also know that the class setup is less than perfect, the books I use are less than perfect, the material I’m teaching is less than perfect, the way I teach it is less than perfect…none of it satisfies me. I hope blogging the class helps me think it through. I take the teaching very seriously, I feel it’s one of the best ways I have available to do more good in the world than I can do just by myself. I’d like to make the most of that. And I’d love to hear from you if you have thoughts.


That’s the setup. I’m going to talk about class one in a minute, but first I’m going to do the Academy Award thing and thank people. Skip this part if you’re not interested.

Justin Singer has evolved from sitting in on the class to being the co-teacher and the person I bounce ideas off. He’s also the person who, when my mouth has written checks my brain can’t cash, I can look at and say “Justin can explain that.” He always either sets me straight (“Yahoo didn’t buy Overture for a couple of million dollars, Jerry, it was $1.6 billion”) or comes up with an engaging example that wakes up even the back-benchers (“An example of vendor financing? Consider your high-school drug dealer…”) He’s been completely indispensable.

Chris Wiggins convinced me I could give something back by teaching. He’s been the person who goads me to be better. He’s also been the Virgil to my Dante. Um, no offense, academia.

Christina Cacioppo and Jeff Bussgang were extremely giving with advice and materials from the entrepreneurship courses they have taught. I have credited everyone else whose material I have used (I hope), but their influence was more pervasive, so I want to thank them here.

The people who’ve come to speak at my class make a pretty awesome list. They have (according to the teacher feedback forms) been one of the best things about the class. The willingness of extremely busy people to take a few hours to come and talk to students reminded me how much I love the startup community, because it really is a community. In order of appearance, to date:

Thanks, all of you. I’ll be calling out future speakers as I blog the class they speak in.


The format in these posts: try to describe what I’m trying to do in the class, put the slides in, then talk about what worked, what didn’t, and thoughts about improving it.

Class one is different. Many of the people in the first session are there to check it out but won’t end up taking the class, and many of the people who will end up taking the class are not in the first session. The goals of class one are like the goals of an introduction in a non-fiction book: tell them what will be discussed, tell them why it’s important, tell them what they’ll learn, and tell them what will be expected of them. That lets them make an informed decision about whether this class is for them or not.

In these circumstances, telling them what they will learn has to hit a few highlights. The class is being taught at the engineering school so I make the point that this is primarily a business course. I will not be teaching them several things that are critically important in a startup: how to build a product (that is, the actual engineering part of building a product), how to manage a project, etc. There is a conscious choice here in entrepreneurship education, and different teachers have gone different ways on it. The first way, which seems more popular on the West Coast–so a path I am loath to discount–is to go through a recipe and have the students effectively start a company now: come to class with an idea, learn how to wireframe, show resources that will allow the students to launch a minimum viable product by the end of the semester. It’s a learn-by-doing way of teaching, and can’t help but educate students in learning how to do; the hope is that those students are then more likely to do something after class because they know they can.

Not teaching this way is a tough decision, and I waver on it. If I were teaching in high school or business school, I would have them build a product. If I were teaching a two-semester course, the second semester (or the first half of the first and the second half of the second) I would have them build a product. But I’m teaching in an engineering school. Engineers should know how to, and be confident in, building something. There are some schools, notably MIT, where actually building things is far more a key component of the culture than others, and I recognize Columbia is not necessarily one of them; I went there. The students at Columbia prioritize engaging with the outside world. But I have one semester to help the students get started on an entrepreneurial career that (a) may not begin immediately, and (b) probably should not begin immediately. I have to trust that they are learning how to build things in other parts of their curriculum.

I should highlight what I think is a key difference in philosophy that drives this decision: I prefer my entrepreneurs to have had at least two or three years of real world experience before starting companies themselves. This gives them the opportunity to have seen big real-world problems and garner the knowledge to solve them. Lying in your bed in your dorm room, if you have big problems, you probably don’t know how to solve them; and if you have problems you can solve, they probably aren’t big ones. (There are, obviously, notable exceptions.)

But if this is true, then teaching to the idea of starting a company today is flawed. And, despite the Lean Startup cant, we have not “solved” the problem of starting a successful startup, we simply have a method that is accepted (and, to some small extent, optimized) to the startup landscape that exists today. I’ve spent the last twenty years in and around startups, and in my spare time I’ve read everything I could put my hands on about commercializing innovation over the previous several centuries. I believe that Blank’s and Ries’ startup recipes are extremely useful (and even an excellent articulation of a part of some underlying truths about innovation) but I do not believe that they will be the recipes entrepreneurs follow ten years from now. And if I want my students to be able to start companies five years or ten years from now, then I need to teach them something other than getting a product out the door today. I need to teach them how to think the way entrepreneurs think. There will come a time when ‘Iterate’ is pointless and wasteful. There will come a time when Node.js is regarded like PHP is today (and like ColdFusion was yesterday.) But the underlying ideas of de-risking and the futility of trying to predict the unknown will always be important. Building the right team will always be important. So I try to teach my students how to think about innovation. Right or wrong? Time will tell.

The second important thing to convey to the students is that I want them to learn how to build an ‘Innovation Driven Enterprsie’, not a ‘Small/Medium size Enterprise.’ This idea of IDE versus SME is somewhat semantic, but is needed so the students who hope to start non-tech businesses or run their family business know upfront. Most startups are SMEs, and there should be more courses in how to start them, but that’s not what I’m teaching in this course.

Enough philosophy. The key takeaways from class one are:

  • What is technology, what is innovation
  • What types of startups are we talking about
  • Why entrepreneurship
  • What will the class entail, what is the format of class, what are the texts, etc.

Here are the slides.

Thoughts: I’d like to do more in this class. Let’s break it down.

Part one–slide 2–I am trying to figure out their level of knowledge. This was a waste of time. Most of the responses were not helpful. I would have done better asking them directly, out loud, even though they hate admitting they don’t know things. In any case I consider the class to be immersion method. Throw them in the deep end and then teach them to swim. If they don’t know what venture capital is, they will by the end of the class. That said, the disparity in what people know coming into the class can be hard, because it is pretty wide.

Part two–slides 4-12–is defining technology, innovation, entrepreneurship, IDE and SME. This is part basic level-setting but mainly meant to get them thinking about some things they might have taken for granted. Technology is not advanced machinery, it is a process that adds value; this might be advanced machinery, but it might also be a business model. The examples abound. Innovation is not invention or discovery, it is a change in technology. Entrepreneurship is not coming up with an innovation, it is starting a business. This last one is one I like to drive home: you are not an entrepreneur unless you start a business. With the caveat that the business might be non-profit, I do not consider writers, artists, playwrights, etc. entrepreneurs unless they’ve started a business. The idea that ‘entrepreneurs are people who venture into the unknown’ is too broad. That is a the definition of an explorer. Entrepreneurs are a type of explorer, but we’re not teaching map and compass skills in this class. The flip-side, that if you don’t start a business you are not an entrepreneur, is meant to point out that the most important thing is not thinking about it, but doing it. I like this section, I think it works.

Part three–slides 18-25–talk about why entrepreneurship is important. I’m of two minds about this part. One the one hand, I don’t think the students are in the mood for exhortation, they’re just shopping for classes. On the other hand, I want them to understand that entrepreneurship is more than just people building better ways to find a date tonight and split the cost of a pitcher of beer with them; entrepreneurship is about trying to change the world for the better, and there is evidence that it is one of the best ways to do so. This will also be important later as I try to get them to think about bigger ideas than Attractive-Mate-Tonight and Pitcher-Cost-Sharing apps for their final project (and in their lives in general.) I think my primary problem with this section is that I just don’t pull it off that well. Text-heavy slides and demagoguery don’t mix. I need to streamline this so that the points I want to make in class one are made more sleekly and the exhortation to do more and to engage with society for the betterment of all is declaimed right before they walk out the door for Winter break.

Part four–slides 27 and on–is the obligatory details of what they can expect from the class and what is expected of them. The one problem I always have with this is that I end up changing it halfway through and some student didn’t show up to class that day and is confused. I’d like to say this is the inevitable result of ‘driving a car, not launching a rocket’, but it really is just because I get halfway through the semester and find myself either behind or wanting to tinker. Need to fix their expectations about that.

This class usually ends a bit early and I stick around to answer questions.

Next class is on Innovation, as seen through Christensen’s Innovator’s Dilemma.


[1] On the last, I disclaim any copyrights I have on all of the material on the slides contained here and in other posts in the series. Use them as you will (so long as you realize that I don’t own the rights to things of other people I use–these things are credited in the slides.) If you want to give me a shout-out, I appreciate it.

[2] I take this as a flaw in my role as teacher, btw. If my students don’t listen to me, that’s because I haven’t convinced them I’m someone they should listen to. I’m working on that.

[3] Of course, I can’t be sure, since it wasn’t graded.

[4] I have some sympathy. I still have, on my shelf in the stack of ‘next to be read’ books, as it has been since college, my copy of Death on the Installment Plan. I’m told it’s quite good. I’m going to read it next, or right after the other books in that stack, which somehow never seems to shrink.