Damon Wayans Jr. And Business Partner Kris Jones Talk To Comedy Hype: Live Booking App ‘Special Guest’, Pitching In Silicon Valley, And Working Towards First Comedy Special

Damon Wayans Jr. is someone we’ve covered here at Comedy Hype several times since our start. We were fortunate to catch up to him for our very first interview together and this introduction didn’t just deal with comedy. See Damon along with business partner Kristopher Jones have teamed up to help innovate the landscape of live booking with newest app, Special Guest. The two men recently made an appearance on the Propagate produced show Planet Of The Apps with Apple; to talk about Special Guest. The App’s main goal is to make on-demand booking for live performances easier. We learned a little more about the Special Guest App and of course talked comedy! Turns out that Wayans Jr. is planning to put out his first comedy special!

CH: Let’s jump into the discussion about the App. What is Special Guest and how does it work?

Kris: The traditional booking process is broken. It’s really stacked up against talent if you’re not managed. Damon having been managed most of his career, gets the advantage of being managed but the other 98% of talented comedians and entertainers out there don’t have that same ability. Damon came up with the idea of why not build a mobile app to make it easier for entertainers and comedians to get paid gigs, and that’s when he approached me.

“We make it easier, and more affordable for anyone, anywhere to hire live entertainment on demand.”

Damon: I do stand-up comedy for most of the year if I’m not doing television or movies and usually you make most of your money when you travel… when I’m local I do a lot of open mics still and that’s kind of where I came up with the idea…. at open mics, it’s not just stand-up comedians that’s there. So I was sitting there and seeing all this talent. It just sucked that majority of these people were not going to be able to have the opportunity to show the world what they’re made of or make money off of what they love to do. It needed to be a platform that makes it easy for talent to book gigs and also consumers and customers to discover talent. It’s kind of hard now, you usually have to hear about somebody or be somewhere, in order to find talent. This app will allow people to discover talent and share talent. And you can have them come to wherever you are. You become the venue.

CH: Wow, so would a talent get paid first or do they perform first?

Kris: They would perform first. The cool thing about this is it’s all being worked through your mobile phone. You sign up for Special Guest as a comedian. You upload pictures and some videos that you’ve done. Put a bio and payment information so you can get paid. Then someone discovers you on the app; you then get a push notification (phone will buzz). You can put your rates in the app and even your cancelation policy. All of that paperwork stuff that most entertainers don’t like, we’ve built that in the app. There are ratings and reviews on both the venue and talent. Then you go and perform as scheduled. Once you perform the venue rates your performance and you get paid in 24-48 hours.

CH: You guys both represent two different worlds. Kris you’re an entrepreneur and Damon you’re a performer. What have you both learned from each other that you can apply to your professions?

Damon: A couple of things. I’ve learned tenacity and to not take “no” for an answer. I’ve definitely taken that with me everywhere I go. I’ve always had that but he’s operating on another level. Their whole industry is built on being determined. And taking that attitude to what I do as a stand-up helps makes my road clearer. If someone doesn’t understand it, doesn’t mean that I’m not any good, it just means they don’t understand it and someone will.

Kris: For me I would say is a creative edge that I’ve learned from being around Damon and working with him. It’s sort of like you get a sense of your surroundings and then you just kind of be yourself. If you’ve seen our show on Apple, the guy (Damon) is just funny, he’s just funny. If you also see that show I also came into my own as a problem solver and tenacious. I’ve kind of learned from Damon by being comfortable in your pocket or what you’re good at. Also the idea of staying focused on the prize and you just execute it.

CH: Damon, So many specials are coming out, will we be getting one from Damon Wayans Jr. soon?

Damon: Absolutely I’ve been putting it together piece by piece.. there is definitely some jokes that I want to replace but my hour is really strong… I’m just looking for 2-3 big jokes that I want to have. Then I’ll have all the people come out to see me and whoever values me the most I’ll do it on their platform. The cool thing I like about my situation is not too much of my material is on YouTube or anything. I think that’s pretty cool so a lot of people that will see my stand-up will be seeing me perform stand-up for the first time.

CH: For some people who did catch your rare performance you did back in 2008 on Def Comedy Jam, will your new material have some of that same energy, like physical jokes?

Damon: I’m still very physical on stage. Still like to have a lot of fun. I like dick jokes, I like fart jokes, I like pussy jokes… those will still be in there but I do have smart jokes as well but those aren’t as fun. Stuff that really makes people laugh, honestly are dumb jokes because life is so difficult, especially now that people just like to laugh and not feel attacked. If they do feel attacked you want to feel attacked only for a little bit then the punchline is that everybody is laughing.


Damon On Def Comedy Jam nearly 9 years ago.

CH: Kris, certain that you also enjoy some comedic relief when you’re not crunching numbers or making calls. Who’s a comedian outside of Damon that you’re checking out when you need that laugh?

Kris: Man I’m like a kid of SNL. I actually do remember when I was a kid and just started getting exposed to comedy… and I never said this to Damon but In Living Color was a huge influence on me man. I just loved it. I always liked black humor, generally speaking, it just speaks to me. My wife and I would go to Caroline’s Comedy Club over the years and we just favor the black comedians. In Living Color was a super big influence on me but I’ve been an SNL guy. Chris Farley for whatever reason… I would just loose it. Watching some of those skits when he would roll up his sleeves when he would jump on the table and break the table. There was just a ton of characters over the years that have emerged from SNL that I’ve admired. I really get comfortable around people that are funny.

It wasn’t hard for me to work with Damon….he and I went to venture capitalist pitches, like major legendary people we would sit across from. He would sniff around for a couple of minutes then he would loosen everyone up with comedy which in turn like I was trying to communicate earlier would loosen me up. Everybody needs to be closer to comedy. I think it should be required reading to unwind and laugh.

Damon: To piggy back off that. I don’t think comedians should have to apologize. I feel like their job is to challenge the group thinking. I think society should value comedians and their independent thinking and allow them to explore and not be held accountable unless you’re just like making fun of handicap people just for being handicap. Comedians should be valued, and they shouldn’t have to live up to the same standards as a politician. Comedians are getting fired from their jobs for being comedians; that doesn’t make any sense. I feel as the world gets darker they should allow comedians to voice their opinions. We’re kind of like the last stand as far being able to speak your mind?

CH: So were you surprised that people were upset over your Fourth of July joke?

Damon: Yes I was very surprised because I make fun of white people all the time. I make jokes on everybody, white people, black people, and Asians. That joke came from just me noticing how much more white people were excited for the fourth of July then everybody else. They put on their American flag shirts and I’m just sitting over here like “Ok”. That’s where the joke came from. Like black people and other people of color they celebrate it because mainly because there’s fireworks, they’re off work and they can eat. Then this whole other section of people just took it so wrong. I’ve never been told to go back to Africa so many times in my life.

Kris: Having sat through this hour set Damon’s talking about; is that a lot of Damon’s humor is intellectual and it requires you to think. You kind of get beat up a little bit but nobody’s safe.

“My jokes are not to make people feel bad and if it does it will just be for a moment.” – Damon Wayans Jr.

CH: Damon, Kris talked about you guys pitching in Silicon Valley. What’s harder, pitching to millionaire investors or going up against a crowd on a Thursday night in LA?

Damon: It’s so different. the difference is that comedy is so different. You know when you’re having a bad set when you do stand-up. But if I’m going to pitch in Silicon Valley, you can have a really good set / pitch but if it’s too early for them and they won’t bite. You’ll leave feeling like you got it and they’ll turn you down. They have a hierarchy, like the guy we’re pitching to is not always the guy who writes the check. So many more levels of business than just a stand-up set.

CH: Is getting investors in Silicon Valley the only place where you can get backing?

Kris: We raised a little over 1.5 Million dollars, and did that over a three-month period. The best place to raise capital is friends and family first. So Damon put in some of his own money and I put in some of my own money. Then you look out to Angel investors. Those are like high network people. We brought on people like Kevin Hart. We brought on Marlon Wayans and couple other comedians and entertainers. We raised like $500K with the first group. It starts at home. If you can figure out a way to leverage what you have and do it on your own I would encourage anyone to do that. Then I would look towards the rich uncle. When I talk to young entrepreneurs I try to get them there and then you start moving up. For Silicon Valley you have to have a polished pitch and really be able to answer some really direct questions. And also to not take things personally. What will happen is that someone will ask me “I want to raise $3 Million” and I will tell them “You have to polish up the pitch” and prepare yourself for the type of Shark Tank that is in raising money.

CH: What’s the overall all goal for each of you with the Special Guest App?

Damon: My overall goal is get this app to working as well as possible and making it a household name. For people to know that if you want quality entertainment you can go on this app and have a great time…You think of Uber before you think of a taxi and that’s what we want the app to do. And to tailor your entertainment interest… It’s also a throwback to live entertainment because I don’t think people leave their house as much and to get people interacting again.

Kris: In a nut shell it’s about being able to democratize the experience of live entertainment. I have a 4-5 year track record of trying to help talented people to get paid for what they do. It pains me to think that the next Damon Wayans, Jr. could be out there as funny as he is, and is struggling to get paid. At the end of the day if we can do that on a scale globally we’re going to build a billion dollar company. And when people think about booking live entertainment they’re going to think of us and see us like a major talent company like a Live Nation.

Check out more information on the App here.