Kaytlin Bailey is baking up a comedy tour

Chad White

You know that feeling of wanting to do something so bad that you just go out and do it? Yeah, you do. That’s the kind of chutzpah it takes to do comedy. Standups aren’t as courageous as the regular person but they do have a job to do.

Kaytlin Bailey and the women of CAKE Comedy consider comedy their job. Their working actors and standups but it’s how they make money. They tour for a living, much like musical acts. These women are funny and you can directly help them with a donation to their new Kickstarter. I sat down with Bailey recently to discuss running a tour and dealing with shady promoters.

Why does the CAKE Comedy Tour exist?

Kaytlin Bailey: It exists because when I got to New York after doing comedy for two years. I felt super pouty about the open mic New York scene and wanted to get back out on the road. I come from a campaign background so I put a tour together. And then I bullied, essentially, these other more incredibly more established comics into jumping on board.

We did a Kickstarter and we’ve been touring the country for four years as the Pink Collar Comedy Tour. We had a discussion a while ago about changing the name and rebranding; we want to level up. Abby’s been on TV for two years and Erin’s debut novel came out and the rest of us are chugging along so we’re trying to get to the next level and use Kickstarter to do it.

I did read that you ran field campaigns for a political consulting firm. Are you finding similarities between doing that and being in charge of this comedy initiative?

Bailey: Yes, it’s sort of a similar process. There’s a lot of moving parts. And it’s hard to get people to like an idea and put their money where their mouth is. There’s sort of a similar philosophy with Kickstarter or any other type of campaign. “Hey! You want to see more women in comedy? You want more DIY comedy?” Stuff like that? Then support it!

Why are tours so popular for CAKE?

Bailey:It combines my two favorite things. I love doing standup in new places. I like to travel -- with these girls especially. And I love performing comedy on the road. That’s most comics’ dream; sure we want to get on TV. We want to do all that stuff. But it’s really to make it easier or more profitable to go out on the road and walking into a smoky place with drunk people to tell our ideas to. And see if we can connect them to people in South Carolina and Southern California and South Dakota. That’s the test: seeing if you can get out there and connect. That’s fantastic.

I don’t want to sound like an asshole but that’s kind of pure comedy right there.

Bailey: Exactly

You’re not just in it for the fame. You’re not saying “I want to be Louis C.K. rich” but you’re just doing it to make people laugh.

Bailey: Right. Censorship can happen in a lot of different ways. From explicitly being told you’re not allowed to say something on stage to just not being booked for a wide variety of reasons. Maybe the booker doesn’t like your style of comedy; maybe vagina jokes are stupid; it doesn’t matter. You are interested in grown ass lady comedy, which is what we do and what we’ve been doing for four years.

If you book us, you’re interested in the CAKE Comedy Tour. If you’re showing up at Chuckle Fuckers on a Saturday night to see something advertised as comedy, you have in no way what that means. The term “comedy” is so big, it doesn’t tell you what you want. If you want to support this kind of comedy, come to the tour. Buy a ticket. Come out and see our performers. It gives us the freedom to do the kind of things that we do and build a fanbase that wants to see more of that. It cuts out the middleman. It’s fantastic.

Is writing on the road easy for you? Obviously, you’ve gotten used to it in the four years you’ve done it. I mean is all this moving around growing on you or is it difficult?

Bailey: It was harder before I had an apartment. I was traveling all the time and had no respite. I was essentially couch surfing for many years here in New York. But things have gotten a lot easier now that I have my own base...now that I’m not shuffling around other people’s spaces or other people’s couches. It’s easy. Pack a suitcase. Write on the road.

I love writing with the CAKE girls because we know each other so well. We’ve seen each other’s work grow and change over four years. At the beginning of the tour, I’ll start out with some nugget of an idea that, by the end of a six or ten city tour, is a whole new chunk. I like showing off [for them]. I love these girls. I’ve admired them the whole time I was in comedy. It’s why I reached out and wanted to tour with them.

Are you enjoying as part of career now? Actually making money and not struggling on a day to day basis?

Bailey: Yes. That’s the goal. This is an experiment. This might fail. That’s absolutely the goal. I’m looking forward to not having an anxiety tax when I forgot to calculate tax into my taco order.  

It really is an experiment. Whenever you hear about a tour, it’s always a young comedian going out. I just listened to So Many White Guys with Phoebe Robinson. She just had an episode with St. Vincent and St. Vincent toured for years -- she just got done touring about a year and a half ago -- in order to be a big as she is now. You never see that with comedians. Typically, it’s “Jerry Seinfeld is going on tour.” You never see “Jessie Girl-From-Arkansas is going on tour.”

Bailey: [laughs] Right. Exactly. I think a couple of years ago when we started, I think I was really smart to work with comedians who were more established than me in the beginning. I was a little green for the kind of work I would be doing. But I’ve grown in four years. And I think we, as a group, are ready to take this to the next level. Rather than trying to convince comedy bookers that they should book and all female tour and just give us their budget (I’m tired of that conversation), we’re just going to sell tickets in advance. And if we sell enough, we’ll book a venue. And it’ll be easy because we would’ve already sold the tickets. There won’t be this theoretical conversation.

We sold out Ashville, New Orleans, San Francisco, Seattle, Portland -- we’ve done well in major cities. I’m still having the conversation that bookers can’t sell a female comedy tour. I’m tired of having that conversation. We’re just going to pre-sell and it’s no question of whether or not we can do it if it’s already done.

Something I’ve always wondered, you just named these huge cities and now you’re going to [all of these different cities], how do you decide what cities to go to and who deserves your comedy?

Bailey: The initial tour started in Charleston because I’m unimaginative and it’s my alma mater. I felt very comfortable bullying the theater director at the College of Charleston into giving us a stage during the Piccolo Spoleto Festival. I leveraged the fact that we were in that festival to book us in other cities. From Raleigh and Charleston. Those are the cities I started with because I have family there. It’s very easy to get my mom’s book club to come out and support the Pink Collar Comedy Tour. We did our first couple of tours and then word spread; we started getting really great press. Then the Boston Globe covered us. It’s sort of taken off from there. We go where we’re wanted. We’ll come to your city for $1,000.If you think you can sell 100 $10 tickets or 40 $10 tickets, I don’t care, then we’ll come to your town. Shoot us an email.


And if we can do this Kickstarter thing, we get to know that’s happening before we buy plane tickets. And get out of bed. And buy a bunch of t-shirts that turns out no one wants. I’m tired of being lied to by coked up promoters that think retweeting something to twelve people is a promotion campaign. Put your money where your mouth is and we’ll come to your city. We’re not going to run the risk of performing because no one realized we were coming. Which is something that happens to comedians on the road all the time. Unless you can sell out a theater with a tweet, you’re really dependent on a lot of people on the ground that don't really know what they’re doing- [who] don’t care about the tour as much as you do.

Which is why you guys had this Kickstarter not as a backdrop but a safety net.

Bailey: We’re trying to get to the next level. We know what we can do and can’t do. Rather than showing up to an empty VFW where the promoter gives us a line about how it was packed last week, we are asking people to buy tickets in advance. It’s unusual but not unprecedented. People buy tickets for events in the future. It’s something we used to do as a culture [laughs]. So buy tickets in advance and once we hit that minimum “we’re not going to lose money” threshold, we’re coming to your town. But if we can’t get over that hump, we’re not coming.

Follow CAKE Comedy on Twitter, like them on Facebook, and donate to their Kickstarter (there are several for different cities so just follow them on Twitter to make sure).