Thomas Middleditch: No algorithm for success

Thomas Middleditch: No algorithm for success

Small screen actor by day, entrepreneur by night. Thomas Middleditch, the Canadian star in HBO’s Silicon Valley, doesn’t just play an entrepreneur as Richard Hendricks. He’s actually a real-life investor, environmental activist, and outdoor lover. We ventured out to West Hollywood, where we chatted over teriyaki salmon bowls to talk success, passion, and his master plan in an unconventional movie industry.

Thomas, can you start by telling us a bit about your background and how you broke into acting?

I was fortunate enough to have found a drama teacher that saw something in me and cast me in plays. I was a student in a school with an improv troupe, which was great because it was pretty rare. I’ve been doing improv for over 20 years. I grew up in Canada where there was a sketch comedy group called “The Kids in the Hall”.

The comedians, they were like gods to kids my age. I wanted to be just like them, and that pursuit lead me to Toronto and then to Chicago, thinking that I would be successful in the Second City troupe (editor’s note: the comedy club and school of improv known for producing top talent), but it didn’t happen. Then I went to New York, and now I’m here. Opportunities opened themselves up as I pursued comedy. I could go on forever, but I’ll get boring quickly [laughs]!


No, that’s interesting! We meet a lot of entrepreneurs and successful people, we want to tell their stories above and beyond that.

Yeah, sure! Well, I think about that, from time to time. Allowing myself some time to remember “Now I’m here, but I started out in a small hippie town in Canada doing community theater.” There are a lot of stops and starts. No one is going to hand you things, you have to be proactive, make it happen, and hope that people see that what you make is good. There’s no algorithm, no set way of doing it. Young comedians or performers, they ask me how I did it. I don’t have an answer for them. In hindsight, i know what worked for me. In Toronto, that meant doing sketch comedy and improv as much as I possibly could. In Chicago, it meant the same thing but being involved in places like Second City. In New York, it was the same thing, though I was started to get commercials. I was starting to write stuff.

If you’re proactive, people will notice if you’re a content producer as opposed to just waiting for something to come your way. Part of it is not wanting to be stagnant, but when it comes to comedy, it’s about wanting to do funny stuff and putting it out there in different ways.

So yes, you can go from theater to theater and do it live, but why not make your little whatever? I mean, I was doing it. YouTube was around but it wasn’t the thing it is now. There weren’t channels and a whole culture around it. That’s evolved. It’s kind of foolish to ignore what that could do. There are people who have essentially made their careers on YouTube and have probably made a whole lot more money than I ever have, regardless of what you think of their content [laughs].


Sure! Do you see your life as an entrepreneur? Do you have a master plan? When you started, were you like “in 5 or 10 years, here’s my goal”?

Totally! Earlier on, I had much more defined goals. Overtime, though, you realize that so much is out of your control. It’s more about doing many things you like and hoping they have positive repercussions, than saying “I specifically want to do this,” which doesn’t materialize most of the time. If that was your only goal and it doesn’t materialize, what will you do next?

Of course, I had personal goals like, “Yes, I would like to work with Quentin Tarantino or Wes Anderson, but I’m aware that the chances of that are slimmer than I care to admit.” What I do instead is say that I want to work with directors that impress me. I’d learned to bring the walls down a bit. In an industry as nebulous as this, your version of success has to change quickly because you get put on a totally different path than you thought you would be on. I didn’t know I was going to be on Silicon Valley on HBO. I didn’t know this show would succeed. That wasn’t the plan, so...


How do you deal with this?

It creates a lot more opportunity. In Hollywood, it’s always good to be associated with success. If you demonstrate that what you do is good and that you’re capable, that’s even better. Once you’ve got one good thing, you get a lot more good things. You can never really tell where the good thing is going to come from. A good example is HBO. I was working on an animated show with the co-creators of Silicon Valley because I had made a similar animation and I pitched it to a bunch of people who thought it was great. We were still developing the pilot and they say, “Hey, we’re working on another show with HBO. It’s called Silicon Valley and we think you’d be interested.” That big dream felt impossible. Low and behold, the animation didn’t happen, but because of that relationship, they literally wrote Richard (editor’s note: Silicon Valley’s main character) as a part for me and I got it.

My point is that those type of things can’t be planned. I wouldn’t have gotten that serendipitous, transitional moment if I hadn’t made those cartoons and been proactive making those things that kept me up all night for weeks on my time. It’s really similar to what Richard does in the show with his startup. What’s more difficult is to know when you should be afraid. A lot of people have failed in the business writing scripts and making movies because they stick pretty rigidly to how they think things should be. They become inflexible, and it becomes impossible to work. But if you’re too flexible, you let yourself be governed by your product or anything, and that’s not good either. You have to find the right balance.


How did you balance your show on HBO and your side projects?

It’s been great working with HBO so far. We only shoot for about four months of the year, so how we use the other eight months of the year is up to us. We can be casted in other movies and work on other things. It doesn’t take too many things to eat up all your time. I’m dealing with that right now, and what I’m doing is finding time just to be human. I have other passions, too. I’m a private pilot and I love flying airplanes. I’m also investing in startups. It’s not easy to balance all these and I had to overcome stress.


Speaking of side projects, we understand you have a pilot license. What do you like about being a private pilot?

A bunch of things. Most of all, planes, the sound of the engines. I like researching different planes and flying them in the switches and stuff. Talking on the radio in terms and all that is fun too. Being able to get in a plane and go somewhere is the best feeling. North America has a ton of small little airports you can just fly into. Last year I flew to Zion National Park, it’s the most beautiful thing. It’s hard to convey the freedom and excitement and the challenge of it. 

Tomorrow I fly to San Francisco just for the day, but the next big journey is up to Canada this summer. There’s a little airport in my hometown i haven’t landed in yet, so I’m going to explore the mountains of British Columbia. Or maybe I’ll fly to the East Coast, I’m touring with a friend doing comedy there, so I would fly from here all the way to Connecticut, then New York, D.C., Philadelphia. 


Even been scared?

Yeahhh. One time last year I was flying in Utah, and there was crazy turbulence, I was bouncing all over the place, my head was hitting the plane roof and my wife was not having a good time. I tried landing on a private little air strip. There was the airfield, a little bit of space, then mountains. So with all the with, the turbulence, I tried landing on my final approach. I was about 100 feet from the ground and the wind just pushed me. It was a very scary landing.


You mentioned that you’re investing in startups. What kinds of projects do you invest in and how are you involved?

Everything I invest in in Silicon Valley has to have a green impact, somehow. I want to support environmental causes and be an activist, and my investments are a good way to do so. That said, you can invest in anything from food, such as Beyond Burger, to clean water projects. I’m less interested in apps or manufacturing projects. Again, part of the absurdity of being on the show that I’m on is that I’ve been afforded a lot of success, so through a few contacts, I can go to San Francisco, get a tour of things, then come back. I don’t have millions and millions of dollars, so I take three or four $25K investments a year and that’s already a good deal flow for me!


You mentioned your environmental activism. What else do you do?

I’m trying to put my money where my mouth is in the sense that I’m trying to invest in companies with a green impact. As an actor, I try to make sure that it’s part of the conversation. I also work with organisations. I’m a long time supporter of the Sierra Club. I think there are also individual choices we can make and it might sound absurd for someone who flies a private plane, but I only eat meat once a week, and I don’t eat red meat anymore, either. The list goes on. The movement is gaining steam and it’s becoming more exciting because people are genuinely looking to make more good food.


Let’s come back to your career to wrap this up. You’re basically your own CEO, the entrepreneur of your own career. How have you done this?

I think some people in the entertainment business are in it exclusively for the business element, and there are some people that are in it exclusively for the art. I think a bit of the both is the best way to do it. You have to look at it a bit tactically and sometimes narcissistically, like working on your brand. That’s how it is. Sometimes, I think it would be nice to stop a bit and focus on the man I’m looking at in the mirror.