This is the first in a new series of Connected Comedian interviews I’m doing with comics from around the country who are members of the Connected Comedy community. They’re designed to help other comedians learn from what’s working for them (or not), and to help you get a sense of how your peers are handling some of the same challenges you may face with your career.

If you’d like to be featured in a future interview, shoot me an email and let me know.

Today’s interview is with Chicago comedian Ryan Budds.

Tell me a little bit about your background in comedy and where you’re at with your career right now?

I got hooked on the idea of standup comedy around 13-14 when my brothers sat me down to watch Eddie Murphy’s Delirious for the first time. I cried laughing, I think for the first time in my life I was completely envious of somebody’s ability to make others do that with jokes.

Six years later, I started doing comedy in 2006 at an open mic in my dorm’s basement in college. I won a radio contest to open for Dennis Miller about 9 months in and got a good tape out of it that later got me work with different agencies like Funny Business. I’ve featured for them ever since, pretty frequently, while trying to work a day job after college.

I quit that job in January of this year to do comedy full time and have been loving my quality of life since then. I work pretty consistently on the road and locally in Chicago at clubs, bars, and random gigs.

How many “fans” do you think you have at this point in your career? I don’t just mean how many people you have following you on social media, but how many do you think are actually paying attention and really care about what you have to say and what you’re doing? How many do you have a connection to that you think will support you in some way? (It’s ok if this is a small number)

I’d say there’s at least 100 people who really care about what I’m doing who aren’t close friends and family. The people that constantly post on content I put online seem to be mostly the same people, and they seem to join in after seeing me live or meeting me somewhere I recently performed.

I don’t know that these people would necessarily buy any/all merch that I released, but these are the people I think would definitely pay to see me at a show in their area. I randomly get emails and messages from people who enjoyed my set somewhere or liked the free album download I gave them for signing up for my email list. I’d like to see this number grow obviously, so I’m trying to think of ways to make that happen.

As far as your career goes, what are you doing right now that you think is working well?

I’m cultivating different opportunities and turning them into comedy-related ventures. I’ve been hosting these trivia nights at bars for a friend who runs a company called YesIAmShow.Biz that produces these nights in the city, and I’ve brought that idea into the south burbs to fill the nights where I’m not booked for paid shows (Sun-Thurs). We call it Standup Trivia, as it’s a trivia night hosted by a comic, and we try and make it more fun and engaging than other trivia nights.

Setting up these locations and hosting them three times a week has really helped me in terms of income, “stage” time, and networking. I try new bits out at these nights frequently and casually, in the same way you might do to a friend you’re running a new joke by. Along with that, I’m pretty solidly booked at clubs, one-nighters, and a few colleges this fall. I’m moving to LA with my wife in October, so the next three months are really busy, but in the best way possible.

What are you having problems with? What’s the most challenging thing for you at the moment?

The most challenging thing for me right now is trying to figure out how to make the biggest impact on people. I’ve gotten to a point where I’ve been relying on the same set for a good 6 months and it needs to be drastically changed. I try and do it once a year, to throw out old ideas and focus on just new material, but I honestly get lazy with it sometimes and it really bothers me.

I’m trying to focus on a daily writing regiment where I do an hour, 2 hours, everyday no matter what. But that can fall by the wayside pretty quick. Another challenge comes with this move to LA. I’ve been doing this in the Midwest for over 6 years, so I feel like it’s a good transition time, but you sometimes hear about being seen by industry too early out West. I’d like to think I’m prepared for anything, but you never know, and that can be a scary feeling.

I’m trying to make sure I have a ton of material in terms of jokes, spec scripts, and video content to showcase myself in a good light when I get out there. I constantly hear the phrase “what else you got” coming from friends of mine who already live out there, usually from the mouths of agents or managers, so I want to make sure I’ve got a lot of bases covered with what I have to offer people.

My wife grew up near LA, so we’ve got a huge family support system out there, which helps. My goal is to be able to have a decent enough income so that I don’t have to get a day job that’s not related to entertainment in some way. I’ll do extra work, I’ll audition for commercials, whatever it takes; I just don’t want to be working at some community college like I did for the last 3 years of my life. Going from a ton of good relationships for booked work with bookers in the Midwest to almost zero on the West coast will be hard, and almost like starting over in a way. As long as I can get on stage frequently and get some paid gigs here and there, I’ll figure out a way to survive out there.

It looks like you’ve been posting pretty regularly on your website for the past few weeks – what’s your strategy behind that? How do you decide what to post? What kind of feedback are you getting from it?

For a long time, I had a static website that only showed what new shows I had coming up. No twitter updates, no Facebook anything, just totally the same information on a page that looked really nice but ultimately did nothing. You actually gave me some great website tips about a year ago on how to improve my website, and I took this into consideration, but didn’t make a move on the issues until I started hearing them again and again on the Connected Comedy podcast.

I knew I had to fix these elements of promoting myself, so a friend designed me a brand new site that utilized WordPress and really let me control a lot of the things I wanted to be able to update. I launched the site about three weeks ago and my goal is to update it with some piece of content daily, whether that be a blog, picture, video, etc. For example, I’m doing a thing called Grinstagram every so often that is just a funny/goofy picture I took on Instagram with some story behind it.

I want to give people a reason to check out my site as a whole, rather than just one part of it like my shows calendar. I’m getting really good feedback from it just from the amount of likes and comments I’m getting on posts that I share on Facebook. My hits are pretty strong at about 700 since I launched, which is about 600 more per month than I was getting with that old site. I’ve been using Google Analytics to see what posts are getting more traffic than others, which is neat and beneficial in terms of creating more content.

Just from my free CD download and a spec script I posted of the show Adventure Time! I got some awesome feedback from people who normally wouldn’t have probably seen what I was up to. You can check out an article I wrote on that feedback here. I’ve got the month’s calendar lined up with what I’m going to post each day, that scheduling is how I work best and get things done. And with that schedule in mind, I leave the house every day doing different things going, “Could that be a piece of content for my site?” Having that mind set keeps me thinking like a comedian way more often than not, which is really neat.

I know you’ve got the Between Gigs webseries you’ve been working on. Can you talk a little about how that came about, what you’ve learned from doing it so far, and what the process is like? How do you produce it, how much does it cost, how much time does it take, etc.? 

Between Gigs was an idea that my friend Dale Zawada and I had that would give us something to do during the day when we’re not doing shows. We wanted to make a microseries, something short and quick we could put out every so often, and that quickly transformed into a weekly 2-5 min web series idea. We knew we wanted it to be random and that we’d touch on different aspects of being comedians in many of the episodes like getting booked, bad shows, setlists, stage names, etc.

And we also realized pretty quickly that it helps to have comedian friends as side characters in the episodes, sometimes playing themselves, but mostly playing weirdos and creeps we interact with for a variety of reasons. After a few months, lots of comics were asking us to be part of the show, which worked out great for everybody in terms of promotion and getting things shot quickly.

We have a brainstorm session every few months for episode ideas where we come up with 20-something shows and then each write up about half of them. We produce the show for pretty much zero dollars. We record most of it in my apartment or around my neighborhood with an HD camera my wife and I got for our honeymoon last Sept. It looks decent and the mic is an external attachment I bought for around $100 that picks up nice sound.

All the props we use are things lying around for the most part. We film the episodes usually two at a time and each one takes 1-2 hours depending on what’s involved. Sometimes we have a camera guy (Bryan Christopher, a very funny Chicago comic who plays a future version of me in an upcoming episode) but mostly it’s us and a tripod.

The biggest thing I think works for the show is consistency. We’ve put out a new episode every Monday afternoon for the past 7 months, and are planning on filming the rest of the year’s episodes before I move to LA so we can finish with 52 solid episodes of this thing. We’re always ahead of schedule by filming multiple episodes in one week, so we have this bank of shows we can put out for future weeks, which takes some pressure off of having to work every week on it. We get usually around a few hundred hits per episode, and sometimes closer to the 1,000 mark on certain shows.

How did you get Todd Glass to appear in your latest video?

Last year around this time, I was working on a podcast called Joking Off with a comedian friend of mine, Kevin Kellam. We recorded about 30 episodes and had a good time with it, but he moved into the city so it became harder and harder to record so we just stopped.

But around episode 20 or so, I saw one of my favorite comedians, Todd Glass, was going to be in Chicago opening for Sarah Silverman. So, I emailed him asking him to do a really short segment on the podcast and that we’d come to him and it would just take like 15 minutes when he was in town. He never emailed me back. I forgot about it, that was in April 2011.

Literally one year later in April 2012, Todd emails me back saying, “Ryan, I just found a bunch of old emails I never responded to. I’d love to do your podcast.”

I was shocked he took the time to respond to an email that old from some random comic in Chicago, but I was thrilled to hear back from him. I replied saying that I didn’t do the podcast anymore but that I’d love to have him on an episode of this web series I was working on. We came up with an idea for how to get him on it without being the same area (we used voicemails he left us as the basis for the episode) and the rest was history.

We were featured on the front pages of Laughspin and Rooftop Comedy, which was really cool, and people seem to really enjoy the episode. We’re obviously going to try and use this episode as a springboard to get future established comic guests on the show. I’m talking to Jimmy Dore right now, who is interested in doing one. It’s very cool to have this platform to reach out to people like that.

Since you’ve decided to make the move to LA in October, how did you come to that decision? Why did you choose LA as opposed to NY? What are you expecting or hoping will happen once you get to LA? Do you have any specific concerns regarding the LA move as relates to comedy?

Like I mentioned earlier, my wife grew up in the LA area and we’ve got a ton of family out there. Lots of support if something went horribly wrong. That’s a huge plus.

From what I hear for everything I want to do, LA is the place to be. I’ve always heard that NY is the place to go to learn how to be a great comic and LA is the place where you put being a great comic to use. I’m not a great comic yet, I know that, but there are a lot of things I want to do other than just standup comedy. I really want to write for television. I want to write for anything, to tell you the truth.

I love sitting around with comics and coming up with bits and creating storylines and things. A writer’s room is like the ultimate office for me. If I could make a career coming up with ridiculous things that make people laugh with a group of other like-minded people, I’d be set. Doing standup is something I never want to stop doing, but branching out into other areas like screenwriting is definitely something I want to dabble in.

I hope that once I get to LA I can establish myself as a decent comic from the Midwest who knows what he’s doing on and off stage. That would be ideal. And if that leads to gigs in any field that harbors comedic talent, I’ll be extremely satisfied.

You’re 6 years into your comedy career – what do you wish somebody would have told you 3 years ago?

I wish someone would have urged me to never be stagnate, to never get used to things on stage. I had (and still have sometimes) this intuition that if an audience is laughing hard at something, there’s no need to change it. No need to switch up a feature set that works 99% of the time, right?

That’s definitely not the case, and relying on a set like that makes you lazy. I also wish I would’ve have told myself I could do this full time 3 years ago. I had this great job after college that paid great and kept me secure, but I think that struggle of having no set income would have forced me to work harder at being a better comic.

During those first 5.5 years, comedy was a secondary job, the FUN job, but it was secondary because it paid about a third of my day job. I’m really glad I got to the point where I realized I didn’t need those set hours at a desk every day to support myself, but part of me really wishes I would have just dived into comedy head first after college.

How would you describe the Chicago comedy scene right now? What advice would you have for a comedian who may be considering moving there?

The Chicago comedy scene is diverse. There’s old comics, young comics, comics of all races and backgrounds, and tons of people doing it for fun, full time, or somewhere in between. I live in the south suburbs, so I’m not a guy that’s at like 15 city mics a week because it wouldn’t make sense for me to do that kind of driving to wait on a list of sometimes 60 comics at any given venue.

The great thing about living near a city like Chicago is the ability to perform in literally hundreds of different types of places. You can hit up a swanky club for a showcase set in the heart of downtown or you can eat shit at a dive bar out in some suburb that feels like the South. You can be seen by everybody or nobody all on the same night. All black crowds, all female crowds, gay crowds, none of that’s uncommon.

There’s a ton of opportunity to learn in the city and surrounding area. I would recommend Chicago as a great place to start doing comedy and to learn how to get comfortable on stage in front of as many audiences as ever. Don’t stick with just doing shows in the city, get out into the sticks and see what it’s like to really perform for people that aren’t like you at all. On the flip side, I’m not really a city guy, but I totally see the benefit of being part of the metropolis of comedy that Chicago has to offer and I take advantage of it as much as I can.

For other Connected Comedians who may read this, is there anything in particular you’d be willing to do to help them? And is there anything in particular that you need help with in case any generous readers out there want to help you?

I’d like to help any comic do anything they need help with. I don’t think I’ve ever turned down somebody asking for advice on how to get started, where to perform, how to write jokes, any of that. I try to be nice to everybody I meet, even if they’re a dick but I feel like they have something to offer in some way.

My first impressions of people can totally be turned around after a few jokes and a beer. I’d be happy to promote anybody that wants to do what I’m doing. There’s no class system in comedy, we’re all trying to make it at a thing that’s just fun and rewarding. Sure it sucks sometimes, but like any job, you’ve got to put up with some bullshit every once in a while. Just do your best to not be the bullshitter, and everything will be fine.

I’d like help in promoting my web series, Between Gigs, if anybody wants to repost episode they dig. That would be great. I’d also love to have as many contacts in LA as possible before I move out there, so if you’re from that area and like anything I do, please hit me up so I can hit you up when I’m out there.

Is there a particular article or feature of Connected Comedy that you’ve found the most helpful so far?

I really enjoy the podcast. I’ve said so in a few comments and reviews, but it really helps put the business side of comedy into a perspective that every comedian who’s serious about succeeding needs to hear. The 5 free tips you gave me last year got me motivated to redo my site, so that was really helpful. I’m a big fan of message boards and commenting on topics that lead to big discussions, so the Facebook group is really helpful.

If you could ask me one question, what would it be?

I’d ask what your big goals are with working so hard on a website like Connected Comedy. Helping comics seems to be your thing, but are you ultimately looking at turning your expertise in marketing into a money making business through comedy?

MY ANSWER: When I launched Connected Comedy a couple years ago I started it because I felt like I had a certain knowledge and expertise that many comics needed and that there really wasn’t any central place for them to get it. It was partially an experiment to see if I could use many of the tactics I promote to build my own audience, and then ultimately convert that audience into a business with people hiring me on a consulting basis to help them grow their fanbase and career.

That’s exactly what happened and I’m really proud of how Connected Comedy has evolved and grown – it’s also how I know that the stuff I’m recommending actually works. A few months ago I was actually offered a job running Digital Media and Marketing for The Academy of Motion Pictures (and the Oscars), which was too great an opportunity to pass up so that is now my full time job.

However, I value the Connected Comedy community too much to abandon it, so I continue to share what I know here and have been thrilled with the way many of my readers have helped keep it alive by doing things like moderating the Facebook Group and helping produce the podcast. I still do a little consulting occasionally when I have time (you can email me if you’re interested), but basically I’m just doing this because I love the community and it’s a great way for me to continue to learn.

If you could ask other Connected Comedians one question, what would it be?

At what point would you feel like you’ve “made” it? What the big end goal for you as a comedian? Is it like an HBO special and fame or is it just being comfortable making some kind of living making people laugh?