MasterClass lets people learn from legends. Co-founder Aaron Rasmussen explains how he got celebrities to sign on.

The Business of Business: I would love to hear about MasterClass, how you got the idea for it and got it off the ground.

Aaron Rasmussen: It's funny, because MasterClass was actually my third business I'd sold before that. My inspiration for it was I wanted to make this documentary series in 2010 about how creative people actually do the things they do. And it's funny because way back then I wrote a list of who I'd want to learn from. And it was people like Steve Jobs, JD Salinger. One of them was Hans Zimmer, and Annie Leibowitz and James Cameron. Unfortunately, Steve Jobs and JD Salinger passed away. But we ultimately did it many years later, when I teamed up with David [Rogier] and we developed this whole thing together. We did actually get Annie Leibowitz, Hans Zimmer, and James Cameron. I actually directed the Hans Zimmer one myself. 

So MasterClass was really fascinating. In many ways, it's a thing that David and I wanted to just make for ourselves. We thought, this should exist, why should it not? And how does Aaron Sorkin actually write an episode of “The West Wing?” And this idea of democratizing access to genius was just so exciting, and all these great conversations that people get to have one on one. Well, how do you bring that to a large audience? Actually creating that is much easier said than done.

It definitely started out with those first seven months of him and I just in a borrowed office space, just calling Hollywood and asking people if they'd work with us, and James Patterson was the first one to fully commit, and let us film him. And that was amazing. Because at the time, online education wasn't of high production value. It was webcams and classrooms, this sort of thing. And we shot it with Bill Guttentag, who's a two time Academy Award winner, and came out with this beautiful set of footage where there's a drone in New York City, this is back when that was legal to do, before the FAA clamped down. I cut this trailer together from it. And then we were able to show people and they could really understand, hey, this is something different. This is something that is capturing a legacy, and really opening up somebody's knowledge to the rest of the world. And then the rest is history. 

It was an absolutely fantastically wild ride, I had the bizarre combination role of creative director, so I was doing everything from overseeing branding to trailers to literally directing them myself. And then also I was CTO, which led to hilarious situations like me interviewing Christina Aguilera on camera, and then in between reloading film trying to fix the CSS on the homepage so the website didn't go down.

So that's MasterClass. And rarely, I think, rarely do you get to just dream something up, and then have it really deliver all the way to the point that David and I got to learn how Aaron Sorkin wrote “The West Wing.” This was just one of those things where it's like, wow, what if you could really do that? And now everyone can. And I'm super proud of what we created.

The hardest part must have been getting James Patterson, that first name. How do you get such big names to agree to do this?

I mean, even getting to a “no” can be really difficult, right? Because if you're going through agents, you might not hear back from anyone. Being just sort of two unknowns, working on this, the trick is to basically go through any channel you can possibly think of. Do they have a production company? Do they have a clothing company? 

What's interesting is that those people have a sense of their personality. When you talk to the studio head for James Patterson, for example, they know that he likes this sort of thing. He works with co authors, so he likes teaching about writing. And that's kind of the way you can first get in the other thing is you think about it like casting a movie. 

With James Patterson, that was the thing that broke it loose, because then it was this best selling author plus the trailer. And then we got Serena Williams, Usher, Annie Leibowitz, Dustin Hoffman. Once you've got that together, it's a thing. My co-founder David's very good at this, this networking side of it, and going out and getting to these people. Once we launched, it was pretty clear it was going to be a thing. So it definitely shifted relatively quickly to we actually have to turn down a lot of people. Which is very awkward, because it's people that you do want to learn from, but you can only make so many classes and you know, there's a certain audience, etc, etc.

Do you have a favorite that ended up teaching?

It's funny for me, because I have so much beyond the frame knowledge, as they call it, right? Because when you direct it yourself, you might be sitting for three or four days having conversations with these people, and you learn so many great things, you distill those down into a class that might be three to seven hours, something like that. But there's so much outside the class that goes into what you end up loving each one individually for different reasons. Deadmau5 was super fun, that was a really great one. And I happen to love electronic music. And I came away from that thinking, wow, if this class would have existed, I probably wouldn't have quit writing electronic music. Because he doesn't really play piano for most of it. He uses his keyboard to just type in notes. I seriously had this insecurity when I used to play music because I didn't play piano. I couldn't ever really be a good musician. And here I am staring at this person who I think is a fantastic musician. And he's saying, “Man, I just use my computer most of the time.”

I really do love so many different ones in different ways. You know, I found I could go on about this forever, but it is relevant to the entrepreneurial journey. Serena Williams, her understanding of the mental fortitude that you need to accomplish extraordinary things was really helpful, because it was exhausting launching that company. When we asked her questions, like, “What do you do when you're down points? What do you do when you're three points off?” And she said, “You just focus on the next point, and then the next one, and then the next one.” And it's so helpful, because you think there's some crazy magic there. But the answer is actually really simple. And maybe not easy. Focus on the next point, the next point, the next point, the next point, and that's basically what we did up until launch.

Now you have Outlier.org, which has a lot in common with MasterClass. They're both in the Ed Tech sphere, more or less, it seems like Outlier.org even more so. What made you want to leave MasterClass and then eventually found this startup?

My hope with MasterClass is that we create something that 100 years from now would be out, collecting the genius ideas and democratizing access to them. We got it to a really good spot. And I was able to take a very much needed year off actually, because as you might expect, training creative product and engineering plus doing your co-founder duties is exhausting. So, I ended up going out and thinking, hey, do I even want to do another company? Do I want to go and go back and get my PhD? I don't know. But what I did know is that I was missing a lot of information about the world. I have never been to India, and I've never been to China or East Africa or Eastern Europe. So I just got a one way ticket and said, “Okay, let's do this thing.” 

“With Outlier, it's very much a personal mission for me to improve education, to provide the thing that I didn't have growing up, which is really access.”

Now, this is an amazing excuse to go have an adventure and learn scuba diving and take a glider over the Alps and all sorts of other fun stuff. But in those travels, I was thinking about, you know, do I want to do something next? It actually took me quite a while to get around to okay, if I do what is that thing? Because at the time, it was very much “I'm not naive when it comes to this anymore.” Right? That was my third startup. A lot of my first two startups went into the ability to do MasterClass. For my second startup, understanding what a consumer brand was, and how to make people like it. And also what artistic and creative cohesion was. In my first company, that was the hard knocks of business and the out of the gate of college. So when traveling the world, I saw that my personal story, growing up in the middle of the woods in Northeastern Oregon, and going to school at Boston University and having education changed my life was not that unusual. And that access to it was.

I think people see similarities between Outlier and MasterClass, partly just because of this very glossy look, that happens to be the artistic style I like. So some of that is just like the way I see the world. I mean, the background behind me is designed by my team. And we all have this nice vision that we're able to come together around when it comes to Outlier. There's a cinematography magazine that quoted our DP as saying, “It's Hogwarts meets Blade Runner,” which I'm like, yeah, there you go. 

“[Entrepreneurship is] about letting go of the roller coaster. The highs are going to feel less high, but the lows will feel less low.”

So, with Outlier, it's very much a personal mission for me to improve education, to provide the thing that I didn't have growing up, which is really access. It's not to replace any system or anything like that. It's to give an option where there isn't an option. Under the hood, they're vastly different companies. The overall goal with MasterClass, we are unearthing knowledge that you can't get anywhere else. There is nowhere where you can find out how Aaron Sorkin writes “The West Wing.” These people, sometimes it is the only place they'll ever say this. And that's amazing. So if you get a couple things that fundamentally change the way you look at your profession, incredible.

Outlier is completely different. If you want to learn calculus from the ground up, that's what we do at Outlier. And what's interesting is, this information is information that's available everywhere. Whereas MasterClass’s information, that's the only place you can get. You want to learn that stuff, go there. 

With Outlier, you could just go to the library, check out a calculus textbook. If you have the attention span, you can just stare at that thing for three months. And you'll know calculus on the other side. That's not particularly fun. So a lot of what we do is really putting together all this great educational psychology and making an experience that motivates you through it, that gives you people to go through it with, that gives you the best instructors in the world on camera — which is a big difference, by the way, between in person and on camera. You can have a phenomenal instructor in person, it doesn't translate. That's not their fault at all. In fact, a lot of the reason they're good in person is it's this bidirectional communication. 

It's been really fascinating to do that too, because it's for credit education. These are actual college credits. They've transferred to Harvard, to NYU, to Georgetown, but they've also transferred to all the other places that we'd expect them to go,  and offset costs for students. And that is a whole different ball of wax.

I'd love to hear about your experiences as an entrepreneur. You mentioned that by the fourth company, you have the option to not do it. What is your advice to entrepreneurs out there, whether they're first timers or serial entrepreneurs?

Well, there's so much advice you can give. I think the most surprising thing, because I've worked with first time founders a few times, I've gotten to see people come up to it. And the biggest thing you have to learn is emotional. It's about letting go of the roller coaster. The highs are going to feel less high, but the lows will feel less low. Instead of being frustrated, you just think, “Okay, what are options?” Now, feel free to ride the roller coaster in your personal life. It's tons of fun to be very emotionally engaged that way. But in your business life, you make the best decisions you can and then you move forward. That being said, it is still incredibly emotionally taxing. 

“Have your personal art on the side. Because when you do need to express things, it's good to have an outlet that isn't just your job.”

So I would recommend treating your mind the way an athlete treats the body. So make sure that you force yourself to rest on occasion, if you, let's say, sprain an ankle emotionally. Let's say something really rough happens to you in your business life or your personal life. Don't run on a sprained ankle, right? Don't expect yourself to get out there and perform the same way you're always performing. You'll just screw things up. And you might  make that ankle have to heal for a lot longer. There's so many other things to learn, product market fit, and managing, and all sorts of things that are part intuition and part intellectual. But I think the trickiest part I've seen for everyone is those emotions, because that's what makes you get that myopia where you're stuck, forcing on one priority. And yeah, you're working 100% of the time, but it's not solving what you actually need to be doing.

It's so easy to get caught up in emotions, when it feels almost as if everything is riding on that company, the success or failure of that, and other people's jobs hanging in the balance as well.

Absolutely. I mean, there's a huge amount of responsibility there. Especially as you hire more people, and they hire more people, you want to see them treat people well. People are choosing to spend part of their life on you. We spend more time at work than almost anywhere else, so spend that person's life wisely. Don't waste that. I think that if you really approach it that way, people appreciate it. I think that it also is a good way for you to frame priority. You're much less likely to give somebody busy work when you're thinking about it that way. Busy work is not necessarily going to push your company forward.

I'm dying to know about your TikTok page, which has, I think, 130,000 followers at this point, which is remarkable. Taking a look at the videos, they're fascinating. So what goes into a video? How do you choose what videos you want to do? And where did you kind of get this idea in the first place?

I've always liked to do art on the side. In many ways. I'm a commercial artist, which is an interesting thing for a CEO to be. You probably see that in the companies I like to make, but I always like to remind my team to have your personal art on the side. Because when you do need to express things, it's good to have an outlet that isn't just your job. And part of the reason is because we make commercial art at Outlier. This is something that we want an audience to love. We want them to be engaged with it. We don't necessarily want our own internal turmoil on everything right? 

So put your turmoil somewhere else. So in this case, the TikTok channel’s pretty funny. It started with me just repairing this fox and I just took a time lapse of it because I like to send stuff to my family. I'm constantly making weird videos. It's just like a fun thing I do. I accidentally got myself stuck snow camping, I wasn't supposed to be snow camping, I got my car stuck, and to spend the night in the snow is incredibly cold, but I have my drone. So I just made a weird commercial for the planet Earth just to amuse my friends and family. It's not something I'm gonna post anywhere. 

So that's basically how TikTok started. I got 1.6 million views on that first one. So I decided to make a rule. The channel that I have, it is only things I want to do. So I post maybe one to two videos a month. Most people are posting three a day. And it's mostly just art that I'm making for my own house like that. If you saw the murder hornet, I've got that in this office. It's just a nice thing to have. And then the most recent one, the fun one is I made this fox sculpture, and it just got commercially produced by Papercraft World. So people are always asking if they can buy my art. I wish, but that's not my job. This is really only for me, and it would be so extraordinarily expensive to hire me to make something. So this company is producing this thing that took me three months to make for $25, which is like the coolest thing because this part of my life, I just want to share it with people.