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Salman Khan and Bill Gates at TED in 2011. (Photo by Steve Jurvetson, via Flickr.)

Salman Khan is known for his educational videos, and his Khan Academy is a non-profit venture, but he has all the hallmarks of an entrepreneur. He made the leap from his full-time job, took a big risk, and built a new organization. He’s tackling a giant challenge, and trying to change the world.

Khan is appearing in Seattle on Wednesday night as part of a tour for his new book, The One World Schoolhouse — about his personal story and the future of education, including the concept of “the flipped classroom.” (Advance tickets for his talk at Town Hall Seattle have sold out, but limited standby tickets may be available at the door.)

In advance of his visit, I spoke with Khan this morning about the evolution of Khan Academy, his entrepreneurial journey, his connection to Bill Gates, the technology he uses, and his current thoughts on technology in the classroom. Continue reading for excerpts, and hope you enjoy the conversation as much as I did.

A lot of people think of you as the guy who does educational videos online. But you’re actually doing a lot more than that these days. Can you give me a snapshot of your work at this point, and where Khan Academy stands?

Part of my joy is that I still spend at least 30 percent of my time still making videos, but that’s me personally. Khan Academy as an organization, the videos are an important part, but just a part. Most of our resources are actually around building the, for lack of a better word, the product — which is the interactive software, the dashboard, the analytics, the tools for teachers, which the videos to some degree only complement. If a student gets stuck on an exercise, the videos are there, and they might be helpful for them. If a teacher sees on the dashboard that a student is struggling, maybe the videos could be a line of intervention. So we have that piece.

We’re almost a 40-person organization. Two-thirds are essentially software engineers working on that type of thing. The other third — I still produce the majority of the videos, but we actually have a few other folks who are producing videos, as well. We have members of our team that go and interface with schools. Khan Academy started as a project for supplemental free tutoring on the web, and we kind of inadvertently started to be used in schools, so we have a team that interfaces with teachers, with schools, trying to understand what’s working and what’s not — communicating that to other schools and teachers. We have experimented with things like summer camps, summer programs, to understand what you can do with the physical environment.

Khan Academy is a non-profit, but you still made an entrepreneurial leap. You left your day job to do this full time a number of years ago. What have you learned about being an entrepreneur?

It’s hard to say how much of your own experience is generalizable. I would say the big, big thing is perseverance. The only reason we’re having this conversation, the only reason Khan Academy exist,s is that there was four years where it was just something that I kept doing. I would meet people who would say, “Why are you doing this? You’re not going to make money off of this. What do you think you’re doing?” I was like, that’s fine, but I really enjoy it, so I’m going to keep doing it. You could tell it almost frustrates them that you continue to do it. “I’m telling you all these reasons that you shouldn’t do it, and this idiot is saying that he enjoys it.” You can’t understate how important that it is.

Different ventures start in different ways. Sometimes it is, you join Y Combinator, you get funding, and you’re off the ground in three months or six months. In my case it wasn’t that. It was four, five years, and I wasn’t suffering those four, five years. I had a job. This was a hobby. I felt like I was seeing progress, I felt good about it. There were people on YouTube who were sending me thank you letters. I felt like, hey, this is doing something. So let me keep going.

But it did require an entrepreneurial leap around 2009, when I wanted to do this full time. I’ll be frank, that was scarier. You see a lot of people who quit their jobs and are not thinking about the repercussions. I thought a lot about the repercussions of quitting my job and doing this. Some people quit their jobs when it’s just a business plan. I would argue that’s almost not advised, at least if you have my mindset. By the time I quit, the site had several hundred thousand people using it every month. We’d gotten some kind of minor external validation at that point. We had some pretty good press at that point, but at the same time it was scary because it was so non-traditional.

I guess that’s the counterpoint — it maybe is less scary to write the business plan and go for venture funding, because that’s such a done thing. Versus starting a non-profit around YouTube videos and this free virtual school. There’s no pattern that you can look at (as a precedent). It’s more like, this is a strange new pattern that I’m trying to prove out.

But isn’t that a hallmark of success? I love the phrase “strange new pattern.” It seems to me that somebody seeing a strange new pattern might actually be looking at opportunity rather than risk.

I think that’s right. As entrepreneurial and creative and revolutionary as we all like to think we are, we all take comfort if we’re fitting a mold, fitting a pattern. I think you’re right, it’s a huge opportunity. But it’s a high-variance situation, is the most rational way to think about it. If you look at the great entrepreneurial stories — and Khan Academy has a lot of work to do before it can fall into that category — but if you think of the Microsofts of the world, there was no such thing as a software company when they started. It was like, “That’s crazy, you’re going to make money off of selling people bits and bytes?” That was strange in the late 70s. But they did it.

Speaking of Microsoft, Bill Gates was key in the early part of your evolution as Khan Academy, in part because he used the videos with his kids and spoke about Khan Academy publicly. What’s your relationship like with him?

I’ll say it’s good, and surreal, from my point of view. He’s incredibly smart and thoughtful and nice. You hear these stories about him being very hard on people or whatever, but I have never seen that. He asks tough questions, and you can’t bullshit him, but if you’re intellectually honest, and you say what you know, and you say what you don’t know, and you’re just honest in that way, he likes that. When I first met him, 90 percent of my brain was saying, “You’re meeting Bill Gates, you’re meeting Bill Gates.” Surreal. Now I would say 20 percent of my brain does that.

There’s kind of a side story, at least for me personally, with this whole experience. I’ve had the opportunity to interface with a lot of less-than-normal (but in a good way) people — people of note, I guess. The big takeaway I’ve had is how down-to-Earth all of them are. But at the same time how smart. It really isn’t an accident that they got to where they are.

Are you still using Microsoft Paint for the virtual blackboard in your videos? No, I stopped using Microsoft Paint, it must be three years ago. I now use this thing called SmoothDraw 3, which is a piece of shareware.

But you’re still on a Windows PC? I’m still on a Windows PC.

Why Windows over Mac? You know, I started on a Windows PC. The funny thing is, a lot of people in our organization use Macs. We’re trying to build a culture in our organization where if you have to communicate something, make a video. That way people can get it on demand. It’s funny, because Macs are normally associated with creative work, and artists. But I’ve actually had trouble getting the same experience on a Mac that I’ve gotten on a Windows PC. I talk about the same experience. For me, when I’m writing, it’s very important that it’s unbelievably responsive. Even a micro-second lag throws it off a bit. I’ve actually had trouble using it on a Mac, period. And on top of that, it’s what I’m used to. I’ll be frank — I think a lot of the long-held reservations about Windows got solved with Windows 7, at least in my mind.

Are you using a Wacom pen? Yeah, that’s exactly right.

Are you on a Windows tablet? No, my primary computer is one where I walked into Best Buy in 2009 and said, what’s the best computer I can buy for 800 bucks? That’s what I got. That’s still my primary computer. I guess it’s getting old now. I just recently got a laptop, but they’re not tablets.

So the input is on a pad next to you on a desk? Yeah. For me, personally, I find that’s much more responsive. I guess I’m a little bit obsessed with this responsiveness. A lot of people have trouble with the Wacom thing, they prefer a tablet, but I haven’t been able to get quite the same responsiveness on a tablet yet.

What is the biggest thing you would have classrooms do with technology to make the impact real, and not just a token?

The thing I would do actually would have nothing to do with technology. It’s related. I would say that the classroom is not for lecture. We have this policy in our company, and in our organization. If you’re talking for more than three minutes, it should be a video. I think that’s a good policy. That works out well. I think that same policy should be true in the classroom. What immediately happens then is that the teachers and students are faced with 60 minutes where they’re forced to interact. If you take the safety and the passivity of the lecture away, you’re like, “Oh, we have an hour to interact with each other every day. What do we do?” And I’m convinced almost any answer to that question is better than a lecture. There are some things I would like to see more than others. I would like to see peer-to-peer tutoring. I’d like to see kids do real projects and real conversations, but pretty much anything you do is better than a lecture. That’s the first thing. I just view technology as a tool for it.

All the time I’m going onto panels, and people get into these weird debates: “Technology is not a solution, or technology is a solution.” I’m like, look, what are you trying to do with the classroom? Let’s not just argue whether we should have an iPad in the classroom or not. I can argue it either way. If you just throw a tablet in the classroom, it’s not going to do anything. But if you’re thoughtful about how you want to rethink the classroom, and the technology helps you do that, I think it can be a huge thing for the classroom.

Why is the Khan Academy non-profit? Why not for-profit? When I made the decision in 2008, there were some VCs, and they wanted me to set up as a for-profit, and it was tempting. But I thought a lot about it, and my previous career was as a hedge-fund analyst. I spent my day and night talking with for-profit companies, thinking about capital structures, thinking about why they do things the way they do, how they raise money, etc., etc. It’s something I thought more about than most people, and probably even more than most entrepreneurs.

For me, at the end of the day, capital structure will dictate what you do, and even with some of those original VCs, you can kind of pretend to be altruistic, Day 1, but especially if you’re taking other people’s money, you actually have a legal responsibility to maximize profit.

Any good business person will say, the best way to maximize profits is to create value for your customers, etc., etc. But at the end of the day, there is one bottom line. I cringe when people say, “Oh, we’re a double bottom-line organization.” The whole reason why that word was invented was that you say, when things hit the fan, what is the thing you care about most. What is your bottom line. It cannot be both profit and your mission.

I enjoyed so many people using these videos. That reward felt like so much, that I didn’t want to mess with that vision. I didn’t want to mess with my own incentives, where I was doing it purely out of joy. As soon as you do a for-profit, if someone comes to you and says, “Hey, we’ll acquire it for half-a-billion dollars,” that’s tempting, but now we say, no, our mission comes first. You actually can’t acquire us.

You can probably tell with the name Khan Academy — I want it to become an institution. When I’m 80 years old, if I said I started the next GE, that would be exciting, if that happened. But if I said, no, I started the next Stanford, that’s even more exciting. What are the institutions that have that staying power, that can stay true to a mission over many, many generations? They’re not for profit.

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