Thomas Middleditch is an actor and comedian best known for his starring role on HBO’s Silicon Valley where he plays Richard, the struggling startup founder. He started his career doing improv theater for the likes of Second City and UCB, and certainly showed off his improv skills during our conversation.
Silicon Valley is the only TV show that I watch religiously, due largely in part to its authentic portrayal of the startup world that I have one foot in the door of. Thomas lives the same authenticity, and isn’t one to shy away from removing the glamour from working in Hollywood. Whether you’re founding a startup, working your way up the rungs as a comedian, or trying to double your client base, you better remember to enjoy what you’re doing to get through the tough days.
In today’s episode,
- You can’t be passive! If you want things to be happening around you, you have to make them happen.
- If you want to be a good artist, you have to experience life.
- Pursuing your happiness is worth the arduousness, the struggle, the inconveniences, and the trolls. Treat all adversity and every challenge like it’s a buzzer beater shot. Welcome it. Embrace it. Step up.
Enjoy!
If you do the work, you still might fail, but if you don’t do the work, there’s literally no chance to go anywhere.
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Some Questions I Ask:
- Did you think that you were on to something with Silicon Valley when you started? [3:39]
- What parts of this business do you love and what parts don’t you love? [10:30]
- What are some of the things that you love about what you’ve created? [13:14]
- What got you interested in comedy and how’d you get into the business? [19:50]
- How did you go from being bullied to not? [24:00]
- Did you do something to figure out how to be accepted as the weird kid? [24:20]
- What do you ascribe to your change in mindset regarding welcoming adversity? [29:59]
- How did you prove yourself when you went from bigger to bigger market? [31:50]
- What happened when you went to New York? [33:30]
- Tell me about your philosophy on serendipity. [35:30]
- Is it healthy to feel unsettled by not taking every opportunity? [45:25]
- How do you keep the headspace when you do the hard work but it goes shitty? [48:08]
- Are there any environmental protection organizations that you’re a part of that you’re excited about? [51:30]
- How did you get into flying planes? [56:30]
- How much does being a private pilot cost? [58:00]
- So why fly? Is it freedom? Is just is it is an escapism? Is it joy? Is it travel? [60:10]
- Do you love flying because you can get lost in all the different elements that excite you about it? [62:46]
- Can you give any inspiration for the people listening to get them over their next hurdle? [65:40]
In This Episode, You Will Learn:
- Thomas’ thoughts on Canada. [1:30]
- The gripping tale of how Thomas got the starring role of Silicon Valley. [4:10]
- What happens when Hollywood and Silicon Valley collide. [6:30]
- Being an actor and comedian seems like it’s all fun and roses, but like any other job, it can be hard, uncomfortable, challenging work. [14:40]
- How to win and lose at craps. [15:50]
- The show business is a business of coveting and anxiety, which is why Thomas spends a lot of his free time focusing on hobbies like environmental activism and being a private pilot. [18:30]
- How Thomas was pushed into playing comedy sports by one of his 8th grade teachers, Ken Wilson. [20:10]
- How Thomas went from being bullied to being voted valedictorian. [24:00]
- Developing moxie is about setting expectations and accepting the challenges ahead. [28:30]
- If you’re just starting out and you’ve got dreams of being big, it’s probably good to be a bit delusional. [30:12]
- Thomas’ low point, which happened when he moved to New York City, where his only friend was a two year old girl who he babysat. [33:35]
- The chain reactions that led to successes for Thomas. [40:00]
- If you’re just starting out, you can’t be passive! If you want things to be happening around you, make them happen. [45:00]
- What you think is at the top of Success Mountain probably isn’t there, so you better be doing something you enjoy along the way. [49:00]
- Check out NRDC and Sierra Club if you’re interested in joining the fight to save the planet. [51:55]
- Thomas’ thoughts on social media.. Not really a fan. [54:20]
- How Thomas walks the talk, by giving up most meat, donating to environmentally good nonprofits, and investing in solar desalination and electric airplanes. [55:00]
- How Thomas got into flying and how you can be a pilot relatively inexpensively. Check out controller.com and trade-a-plane.com to check out used airplanes for sale. [56:45]
- If you want to be a good artist, you have to experience life. [64:30]
- You don’t have to spend all day doing only what you are 100% passionate about to be happy. Pursue your passions on the weekend. Even for those who are living the dream, some days suck. [71:20]
- “You’ve got to find your happiness, and as long as you don’t have to fuck people over to get it, it’s very worthwhile pursuing.” [73:00]
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