Matt Ruby on How to Rebound From Rejection

In Chapter 6 of 19 in his 2012 Capture Your Flag interview, standup comedian Matt Ruby answers "How Do You Deal With Rejection?"  Ruby, a self-appointed rejection expert, offers tips on how to get through those moments.  He learns along the way that putting up with the bad parts helps you get to the good parts.  He notes the importance of having a positive self-image that is grounded so you understand why you are getting rejected when trying to hit your goals. 

Matt Ruby is a standup comedian and comedy writer based in New York City.  He produces a video comic strip at Vooza.com, co-produces the weekly show "Hot Soup", co-hosts the monthly show "We're All Friends Here", and writes a comedy blog "Sandpaper Suit".  Ruby graduated from Northwestern University. 

Matt Ruby on Learning the Realities of Working in Comedy

In Chapter 7 of 19 in his 2012 Capture Your Flag interview, standup comedian Matt Ruby answers "How Are Your Comedy Career Aspirations Changing as You Gain Experience?"  As Ruby gains experience performing comedy, he gets more exposure to what life looks like working in comedy.  Experience allows him to look beyond the glamorized life of a working standup comedian.  He learns the costs and benefits of the standup lifestyle and begins finding new options - writing, directing, producing - that emerge as he builds experience. 

Matt Ruby is a standup comedian and comedy writer based in New York City.  He produces a video comic strip at Vooza.com, co-produces the weekly show "Hot Soup", co-hosts the monthly show "We're All Friends Here", and writes a comedy blog "Sandpaper Suit".  Ruby graduated from Northwestern University. 

Matt Ruby on How Personal Priorities Change With Age

In Chapter 8 of 19 in his 2012 Capture Your Flag interview, standup comedian Matt Ruby answers "How Are Your Personal Priorities Changing as You Get Older?"  Ruby notes how personal connections are becoming more important to him as he gets older.  Also, he notes how before he wanted to experience a lot of little things and now he prefers to do big things while getting things done with his work.  He talks about how mortality is a motivator and Matt Ruby is a standup comedian and comedy writer based in New York City.  He produces a video comic strip at Vooza.com, co-produces the weekly show "Hot Soup", co-hosts the monthly show "We're All Friends Here", and writes a comedy blog "Sandpaper Suit".  Ruby graduated from Northwestern University. 

Matt Ruby on How Confidence Can Make You More Creative

In Chapter 9 of 19 in his 2012 Capture Your Flag interview, standup comedian Matt Ruby answers "How Is Your Creative Toolbox Changing?"  Ruby speaks to the instinctual skills he uses to twist jokes on stage and take the audience on a journey.  For Ruby, the confidence that comes with having more control on stage allows him to ultimately perform at higher levels for his audience. 

Matt Ruby is a standup comedian and comedy writer based in New York City.  He produces a video comic strip at Vooza.com, co-produces the weekly show "Hot Soup", co-hosts the monthly show "We're All Friends Here", and writes a comedy blog "Sandpaper Suit".  Ruby graduated from Northwestern University. 

Matt Ruby on How to Use Deadlines to Achieve Writing Goals

In Chapter 10 of 19 in his 2012 Capture Your Flag interview, standup comedian Matt Ruby answers "How Are You Learning to Better Manage Your Time and Commitments?"  Ruby acknowledges he spends too much time responding to other people - for example using social media - that doing his own thing.  To be more productive, Ruby uses deadlines to achieve his writing and comedy performance goals. 

Matt Ruby is a standup comedian and comedy writer based in New York City.  He co-produces the weekly show "Hot Soup", co-hosts the monthly show "We're All Friends Here", and manages a comedy blog "Sandpaper Suit".  Ruby graduated from Northwestern University. 

Matt Ruby on How to Break Out of a Comfort Zone

In Chapter 11 of 19 in his 2012 Capture Your Flag interview, standup comedian Matt Ruby answers "What is Your Comfort Zone and What Do You Do To Break Free of Living In It?"  Ruby notes how his comfort zone is actually being in an uncomfortable place.  His life is always about doing new things, moving to new places, trying new stuff, and hanging out with new people.  After performing comedy for over five years, Ruby finds himself trying to stick with things more often and more fully embrace who he has met and what he has done. 

Matt Ruby is a standup comedian and comedy writer based in New York City.  He co-produces the weekly show "Hot Soup", co-hosts the monthly show "We're All Friends Here", and manages a comedy blog "Sandpaper Suit".  Ruby graduated from Northwestern University. 

Matt Ruby on How Fear Can Be a Motivational Tool

In Chapter 12 of 19 in his 2012 Capture Your Flag interview, standup comedian Matt Ruby answers "Where Did You Learn Your Work Ethic?"  Ruby finds fear motivates him to practice enough to perform at levels that meet his expectations.  He notes how a string of bad shows, where he is not doing as well as he could be doing, pushes him to compare his performance and push himself to succeed.  He notes how technology can be a negative influence on his productivity and how unplugging is important for him to stay on track and produce and practice new comedy material. 

Matt Ruby is a standup comedian and comedy writer based in New York City.  He co-produces the weekly show "Hot Soup", co-hosts the monthly show "We're All Friends Here", and manages a comedy blog "Sandpaper Suit".  Ruby graduated from Northwestern University.

Matt Ruby on Finding Meaningful Work Expressing Yourself on Stage

In Chapter 13 of 19 in his 2012 Capture Your Flag interview, standup comedian Matt Ruby answers "What Makes Your Work Meaningful?"  Referencing what he shared in his 2011 Capture Your Flag interview, Ruby defines meaningful work starting with the truth telling and story telling elements.  He adds that, at a deeper level, being able express himself on stage gives him a pulpit to share.  He follows up that moment of expression by reflecting on what he has done and learning from the experience.  Ruby talks about the flow state he is able to enter working the room. 

Matt Ruby is a standup comedian and comedy writer based in New York City.  He co-produces the weekly show "Hot Soup", co-hosts the monthly show "We're All Friends Here", and manages a comedy blog "Sandpaper Suit".  Ruby graduated from Northwestern University.

Matt Ruby on Adapting Standup Comedy Writing to Screenwriting

In Chapter 14 of 19 in his 2012 Capture Your Flag interview, standup comedian Matt Ruby answers "Which Standup Skills Are Transferable to Comedy Web Series and Which Are Not?"  The transferable comedy skills Ruby sees as most relevant are writing skills.  He shares how character writing is very different between stage and script.  Screenwriting allows for more non-verbal character setup whereas standup comedy character development is personal and mainly verbal. 

Matt Ruby is a standup comedian and comedy writer based in New York City.  He co-produces the weekly show "Hot Soup", co-hosts the monthly show "We're All Friends Here", and manages a comedy blog "Sandpaper Suit".  Ruby graduated from Northwestern University. 

Matt Ruby on How to Improve Comedy Writing Over Time

In Chapter 15 of 19 in his 2012 Capture Your Flag interview, standup comedian Matt Ruby answers "How Are You Improving How You Write Comedy?"  Ruby shares how he is improving how he writes by getting tighter or more precise in his words.  He adds he has developed a better filter for what is appropriate.  Additionally, he notes how he is able to take material in new directions, a development he calls going from "A to C" instead of "A to B." 

Matt Ruby is a standup comedian and comedy writer based in New York City.  He co-produces the weekly show "Hot Soup", co-hosts the monthly show "We're All Friends Here", and manages a comedy blog "Sandpaper Suit".  Ruby graduated from Northwestern University. 

Transcript: 

Erik Michielsen: How are you improving how you write comedy?

Matt Ruby: I think I’m getting tighter, like in the amount of words that I use, which helps, like the shortest distance between 2 points is a good idea in comedy or in any writing. I think also what do I wanna talk about knowing that. Sort of like knowing what to throw out or what’s just not gonna fit in with the other stuff that I do. You know, just sort of this filter of knowing what’s appropriate or not. I don’t know, when I was starting out, I think a lot of times, like, I would go from A to B with a punch line and I’m getting better at going from A to C, like A to B is just like: oh, yeah, yeah, that’s funny-ish and that’s exactly where people would expect it to go. Whereas A to C is like: oh, I thought it was going in that direction, but I didn’t realize it would go that far, or that twist or that thing. And kind of giving that extra spice or, you know, like a little bit more of like—to me that’s the difference between like a good joke and a great joke is like when it’s like: oh, there’s a little twist that you know you didn’t see coming and it was funny all along the way and then there’s something else on top of that that’s even better, and then that’s I think when you get something delightful.

Erik Michielsen: Could you give me an example of a couple of pieces in a routine that you might use, you know, A to B versus A to C?

Matt: Okay, so I have a joke about how girls will drop the boyfriend bomb on me, and how fast it comes, and so I’ll be like, you know, when I’m talking to a girl, I’ll be like, “Hey, how’re you doing?” And she’ll be like, “My boyfriend says I’m fine.” And that’s A to B, you know. Like that’s fine, it’s funny, it gets a laugh. And then, you know, what I’ve added on to that is like, “Okay, can I get a foot-long chicken teriyaki, please? It’s a really judgmental Quizno’s we got here.” That to me is the C, or the taking it and giving it a twist of like that one extra line that’s, okay, it was a perfectly fine joke, but now to me that’s a more interesting or intriguing, or another layer to it that as opposed to just like a quick in and out sort of like meat and potatoes joke.

Matt Ruby on Why to Work With Teams on Comedy Projects

In Chapter 16 of 19 in his 2012 Capture Your Flag interview, standup comedian Matt Ruby answers "What Do You Enjoy Most About Working With Teams?"  Group comedy writing, performance and production not only provides Ruby a collaborative feeling but also creates an optimistic creative energy that can be positively reinforcing as material gets created and shared or performed. 

Matt Ruby is a standup comedian and comedy writer based in New York City.  He co-produces the weekly show "Hot Soup", co-hosts the monthly show "We're All Friends Here", and manages a comedy blog "Sandpaper Suit".  Ruby graduated from Northwestern University. 

Transcript: 

Erik Michielsen: What do you enjoy most about working with teams?

Matt Ruby: I mean I enjoy hanging out with other people so I think that’s just a constructive aspect on it just from a personal or emotional level I think it’s good to hang out with other people and to work on stuff together, I think, you know, comedy can a lot of times be sort of a lone wolf sort of thing so it’s nice to feel like there’s a group working on something. And then also, you know, it’s just nice to have like a group point-of-view to have like, “oh did you think about it this way?” Or like to have one person come up with an idea and you bounce it off them and then they’re like, well, what if we tried it this way or — like, they’ll take things in a direction that you never would’ve thought of and it could be really like cool and surprising and sort of like an interesting twist to an idea that you had but you never would’ve taken it there. 

And I think it’s, you know, you got more juice behind you. I don’t know, it’s more like being a gang than just a vigilante, you know, there’s more of a group effort and you feel like you can accomplish more and do more, you know. At the very least, there’s this group of people who believes in what you’re doing and is excited about it, so that’s to me like more indicative that other people will be excited about it as opposed to like sometimes when you’re just on your own trying to come up with ideas, like you just don’t — you might think it’s good, but you don’t really know until you release it to the world, and you have to wait, you know, until that happens. Whereas like when you’re producing stuff as a group, at least you’re, hopefully, like pleasing each other or entertaining each other along the way and so you’ve got some clue that you’re on to something.

Matt Ruby on Louis CK Style Influences on Making Better Comedy Videos

In Chapter 17 of 19 in his 2012 Capture Your Flag interview, standup comedian Matt Ruby answers "What Has Louis CK Taught You About Making Better Comedy Videos for the Web?"  Ruby notes how having full control over the creative process allows Louis CK to communicate a more personal point of view.  He notes how Louis CK is able to get more personal in his work on his show "Louie."  Ruby notes how this is also true with Woody Allen films and how the director also keeps ownership over his personal vision.  Matt Ruby is a standup comedian and comedy writer based in New York City.  He co-produces the weekly show "Hot Soup", co-hosts the monthly show "We're All Friends Here", and manages a comedy blog "Sandpaper Suit".  Ruby graduated from Northwestern University. 

Transcript: 

Erik Michielsen: What has Louis CK taught you about making better comedy videos for the web?

Matt Ruby: Well, I think the fact that he makes everything himself and, you know, like writes it, acts in it, edits it, directs it, and has full control over the process I think is, you know, I think you can sense it in the stuff that he makes, it feels more like something that comes from a single person’s viewpoint as opposed to so much of what’s on TV seems like it comes from a room filled with like 20 people that are all trying to agree which is cool but like a little bit more – makes stuff more homogenous and so I think, you know, part of what you see from — I’m thinking specifically the show Louis is that you can— if you do that, you can get stuff that’s sort of weirder, more personal or more—you know I think Woody Allen films have that too where it’s like, oh this really feels like it just came from one person, as opposed to like a committee decided that this was best. 

And I think it’s part of like what makes his stuff special and I think it’s something to—I don’t if I necessarily shoot for it in everything that I do but just something to keep in mind that is like, you know, oh, it’s okay to be cool or—not it’s okay to be cool—but it’s okay to be weird or to you know—sometimes his stuff will just get really absurd or just go off into some weird, you know, fantastical place and then come back to reality and, you know, sort of stuff that if you had a committee deciding on, they’d be like, no, that doesn’t make sense. Whereas like you can kind of indulge whatever your own personal vision for it is, and that’s what makes it unique to you and what you’re making is gonna be more unique.

Matt Ruby: How to Film a Web Comedy Series on a Budget

In Chapter 18 of 19 in his 2012 Capture Your Flag interview, standup comedian Matt Ruby answers "What Has Filming a Web Comedy Series Taught You About Doing More With Less?"   Ruby talks about the importance of communicating a vision to onboard a talented team to work within budget constraints.  He notes the more you have to prove a concept, for example showing them a script, the better chance you can onboard them.  Ruby notes the importance of setting managable and realistic timeframes given the sacrifices team and crew may be making.  Lastly, Ruby notes the benefit of having budget constraints and working cheaply.  Matt Ruby is a standup comedian and comedy writer based in New York City.  He co-produces the weekly show "Hot Soup", co-hosts the monthly show "We're All Friends Here", and manages a comedy blog "Sandpaper Suit".  Ruby graduated from Northwestern University. 

Transcript: 

Erik Michielsen: What has filming a web comedy series taught you about doing more with less?

Matt Ruby: The biggest thing is trying to work with other people and trying to, you know, like, especially if you’re getting people to work for cheap, or free, or you know, like less than they would normally get for doing something, I think you have to kind of give them a vision for why they should wanna do—like, they should be excited for the project, you know, should be making something cool, funny, fresh, something that they wanna be part of, something that if they’re not getting paid anything or a lot right now, maybe down the road could turn into something. 

Thinking about what are their desires or goals and like how can you meet them or how can you guys meet halfway, I think it helps too, to take stuff as far as you can on your own before you bring other people in like if you’ve got scripts to show people, that’s way better than if you just have an idea for a script, and if you’ve actually shot something already, and you have that to show, that’s gonna be even better than a script, so like the more you can kind of prove the concept to people the more I think likely you are be able to get them onboard for, maybe, you know, not what their normal rate is, sort of thing. 

I think also you know you need to realize that there’s a limited window on that, you can’t just keep, you know, milking people, you know people just don’t have the time or the energy, the resources necessarily to donate, you know, all the time, so, you know, like hopefully, you know, you can have something that evolves into something bigger that does have a budget that’s more substantial. 

Also I just think people spend way too much on everything all the time. Like I’m mean, I’m a cheap bastard, so like I just sort of apply, you know, if I’m working on something, a project I conduct it the same way I do my normal life which is like I don’t spend money if I don’t have to, so like if I can use cheap props or film somewhere cheap, or you know, just I think people—when people are spending other people’s money, they spend it in a way different way than when they’re spending their own, so I think it’s just, you know, try to, you know, try to be a cheap bastard, even when you’re working on stuff—I don’t know, I just think—I think having those constraints even when you start out, like knowing, okay, we need to do this all in one location, or with these 3 actors or it needs to be 60 seconds or less, or whatever your limitations are, and be like, okay, well, that’s what it’s gotta be, so now fit into that, you know, box or perimeters, and make it work. 

And you know I think that can—that can actually—you know if you embrace that, it can actually kind of encourage creativity or take you to an interesting place as opposed to being like well, no, I need, you know, 5 locations, and dozens of extras and you know a budget of you know all this money and all that stuff. Whereas like, is that really making it funnier or better? You know I think that’s probably the bigger question is like, okay, well, if this is a little rough around the edges or you know, kind of cutting some corners here or there, is that the thing that’s really gonna make it not as good or is it just gonna make it not as polished? And I don’t always care about polish, like some rough edges are alright for me. Sometimes that’s what makes it interesting.

Matt Ruby on Blending Artistic and Financial Goals in a Creative Career

In Chapter 19 of 19 in his 2012 Capture Your Flag interview, standup comedian Matt Ruby answers "What Part of What You Do is Art and What Part of What You Do is Commerce?"  Ruby notes how making art can become selfish if it does not have some tie back into how it pays the bills.  He notes the challenge lies in building a bridge between the artistic output and the commercial success. 

Matt Ruby is a standup comedian and comedy writer based in New York City.  He co-produces the weekly show "Hot Soup", co-hosts the monthly show "We're All Friends Here", and manages a comedy blog "Sandpaper Suit".  Ruby graduated from Northwestern University.

Transcript: 

Erik Michielsen: What part of what you do is art? And what part of what you do is commerce?

Matt Ruby: Sometimes the way I feel about it is like art is just sort of the selfish, you know, like, say whatever you wanna say, or make whatever you wanna make, and don’t even worry about whether it’s, you know, gonna make you money or you know, what’s the—how does it further your career or whatever else your agenda is. Whereas the commerce-side of things would be like, alright, how am I getting paid? Because you gotta do that too. 

So I think part of the challenge is figuring out how to bridge those two, you know, if you can. Like, you know, how can you get paid or you know have a career or produce something that is, you know, commercially viable to some extent and then also how can you be making art, how can you be making something that you’re proud of or that you think is, you know, part of your vision or something that you wanted to make or see in the world. What’s the—and then how do you overlap those two, and I think, you know, that’s a spectrum that everyone can kind of choose their own point on there, like I’m—I think you—I think sometimes the worst thing you can do is sell out and not sell anything, that’s like the worst option. But, you know, just being a complete artist and, you know, just being completely selfish and no one cares at all about it does pretty bad too. 

So, you know I think having, you know, a modest amount of commercial goals, you know, with what you’re making is, in my mind the right path of like—it’s also validation that like whatever you’re doing is worth something to someone, you know, that like, oh yeah, this is good enough to either you know get paid for or you know if you’re, you know, making a show that people sell ads on or you know someone’s gonna watch it or, you know, something like that is happening to sort of encourage you to do more of it.

Garren Katz on What Gets Easier and What Gets Harder

In Chapter 1 of 15 in his 2012 Capture Your Flag interview, business and personal coach Garren Katz answers "What is Getting Easier and What is Getting Harder in Your Life?"  Katz finds himself stressing less and getting more comfortable with the decisions he makes.  As far as what is getting harder, Katz notes a growing challenge in his life is taking on more responsibilities that come with his desire to live better and more fully. 

Garren Katz is a business and personal coach based in State College, PA and advises his national client base on small business management, entrepreneurship, relationships, and personal finances.  He is also an active angel investor in several business ventures.  He earned his BA from Western Michigan University. 

Transcript: 

Erik Michielsen: What is getting easier and what is getting harder in your life?

Garren Katz: I would say life, actually, is getting easier. Trusting myself, trusting that whatever decision I choose is going to work out and it’s going to work out well. Not stressing as much about the little things that really don’t matter. The older I get the more clear, the more in focus priorities become. That’s getting easier. What’s getting harder is as I take on more in life, strengthening that inner accountability to be able to execute, you know, playing a bigger game, living a bigger life. I wouldn’t say that’s dauntingly harder, but it is more challenging. It’s a great challenge but that’s getting harder.

Garren Katz on Finding Nontraditional Career Inspiration

In Chapter 2 of 15 in his 2012 Capture Your Flag interview, business and personal coach Garren Katz answers "What Role Has Family Played in Shaping Your Career Aspirations?"   Katz notes how both his father and stepfather owned their own businesses.  Watching each manage his respective small business teaches Katz to understand job options beyond 9 to 5 careers.  Katz also takes inspiration from his mother, who changes career in her late 40s, and learns to appreciate having a continuing curiosity to expand interest and skills in life.  Garren Katz is a business and personal coach based in State College, PA and advises his national client base on small business management, entrepreneurship, relationships, and personal finances.  He is also an active angel investor in several business ventures.  He earned his BA from Western Michigan University. 

Transcript: 

Erik Michielsen: What role has family played in shaping your career aspirations? 

Garren Katz: You know both my father and my stepfather own their own businesses, so I would say I always, you know, I grew up in an environment where a 9-to-5 job was never the norm, and it gave me a lot of confidence to perhaps not take the traditional -- some of the more traditional paths career-wise. So I think that definitely shaped me the fact that both male—significant male figures in my life own their own business.

 And then my mother, she’s the vice president of a college in the Midwest. She really found her stride later in life, in her late-40s and now is extremely accomplished, and I think that even gave me a lot of confidence to understand that, you know, the journey can be long, and it is exactly that, it’s not this scripted, you know, pap-pap-pap-pap-pap and end up here. You can really find yourself in your 20s, 30s, 40s, 50s, 60s, the opportunity is always there to find yourself and so I think at whatever age you are, you should still be seeking and looking to hit your stride, and even if you think you’ve hit your stride, continue to look because there’s always fantastic opportunities to expand yourself.

Garren Katz on How to Talk About a Career Change Decision

In Chapter 3 of 15 in his 2012 Capture Your Flag interview, business and personal coach Garren Katz answers "How Did You Set Expectations With Others and Yourself Making a Career Change?"  Katz notes how he was uncertain how to talk about his experiences and intentions going through the process.  Over time, Katz gets more clear on his journey and goals and in turn is better able to answer questions about why he did what he did. 

Garren Katz is a business and personal coach based in State College, PA and advises his national client base on small business management, entrepreneurship, relationships, and personal finances.  He is also an active angel investor in several business ventures.  He earned his BA from Western Michigan University. 

When to Leave a Cruise Control Job and Change Careers

In Chapter 4 of 15 in his 2012 Capture Your Flag interview, business and personal coach Garren Katz answers "What Has Been Most Challenging About Changing Careers and Becoming a Coach?"  For Katz it is finances.  Working in sales for many years, Katz finds it easy to be on cruise control.  Moving into coaching, Katz starts from scratch not only from a financial perspective but also from a confidence perspective.  He talks about his experience building a new foundation in his new career. 

Garren Katz is a business and personal coach based in State College, PA and advises his national client base on small business management, entrepreneurship, relationships, and personal finances.  He is also an active angel investor in several business ventures.  He earned his BA from Western Michigan University.