Jake Weisman and the Love of the Struggle

Though it was only on for two years, Jake Weisman’s The Morning After Podcast, which he co-hosted with Eli Olsberg, was a must-listen and example of what a great podcast could be. Each week, Weisman and Olsberg would bring in a guest from the adult film industry to interview in a manner that humanized them and showed how porn stars are just as multi-dimensional as anyone else.

Weisman ended the podcast a couple years ago to focus on his budding comedy career, and though it was tough for listeners to say goodbye to such a fascinating show, that decision is starting to pay dividends for him.

Weisman has made a name for himself in the Los Angeles comedy scene with both his sketch group, WOMEN, and his standup, which brought him to Montreal last month to perform in the Just For Laughs Festival’s New Faces Showcase.

I caught up with Weisman recently to talk about Just For Laughs, his start in comedy, and how he came to be friends with so many porn stars.

That was very cool to see Bill Burr at your showcase.

Oh my god that was actually one of the best things at the festival for me because he is definitely one of the best comedians ever. I feel like no question. I went up in the middle of the lineup so the first part of the show I was on the side of the stage and I could see the performers and I could see Bill Burr laughing very hard at people and it just put me at ease because people love to focus on the negativity in comedy and how comics take each other down and what they don’t focus on is that a lot of comics support each other. What was so cool about seeing Bill Burr is that he has achieved pretty much the height of comedy or at least standup comedy, in my mind, and he still enjoys it. He still likes new people and he is not threatened by it. He really likes it. He loves laughing. He loves the younger generation coming up and laughing at it. It was so comforting to see him laughing that it completely put me at ease for that show. It was like, “Oh, that’s so great.” He’s the best and he’s still just enjoys comedy because comedy is the purest form and one of the most beautiful things and he just loves it. It was incredible.

You’re in LA. Did you start there?    

I started doing comedy in LA in 2009 in the summer. I moved out here right after college with no intentions of doing comedy at all. I sort of wanted to vaguely make movies. I was actually more interested in documentaries than anything, but I had a cousin who was a line producer for various TV shows and movies and he said, “Yeah I can get you a P.A. job if you move out here.” So I was like, “Alright well I guess I’ll just move out there.” I kind of wanted to move to San Francisco because I’ve always wanted to move to San Francisco but I thought, “Well I can get a job in LA so I’ll figure out how to make movies.”

I had no idea what I was doing. I had taken one film class at the school I went to but it wasn’t really enough. I hadn’t read screenplays or anything I was just like, “I’ll go and figure it out.”  I had complete terror and fear in my body but also wide-eyed optimism that I would figure it out somehow. Then I worked all these different jobs in the film industry – in the art department, in post-production, I made copies of DVDs for Sony for a year, I worked on sets, I worked in offices, I drove around the city dropping packages off, I was an assistant to a director for awhile – I was doing all of these jobs and just wasn’t writing. I’d write like two pages of something and then throw it away. I’d tell people I was writing and I wasn’t.

I just had a lot of shame and I hated myself so much so when I turned 26 I was in the worst place in my life and I was like “something has to change.” I had two friends who were doing standup comedy. One of them is Guy Branum and the other one is Julia Bensfield Luce. I knew them from other parts of life and I was like, “I don’t really know anything about comedy at all but what will get me writing is if I start doing open mics.” I started going to open mics to watch them and then I got the balls to go on stage once and I did it a few more times and got really hooked and I had no idea what I was doing. I didn’t really even know technically what a joke was but I was like, “This is a great feeling.” It was kind of like jumping out of a plane for me because I had never performed or anything like that in my life and I didn’t really know what a drug was. But I was like, “This is a wild experience I can tell my grandkids if I ever have them.” But I’m skipping the kids and going straight to grandkids. [Laughs.] Anyways the point is that I started doing it and I got very hooked and after a few months I was like, “I think I like this better than I’ve liked anything in my life before so I think I’m going to figure out how to do this even though it seems like the worst decision ever and impossible to achieve as a career. But whatever, it feels good so I’m going to do it.”

It didn’t take long for you to get hooked? It just felt right immediately?

It’s kind of the only thing I’ve every done that clicked immediately in terms of loving it. It takes a long time to get good but the addiction of it – just the immediate response you get from crowds or even lack of response – is so gratifying. Because I would try to write these screenplays and I would be however many pages in and I would have no response. I had no idea if it was going well so I was just bummed and didn’t have the resolve in myself to finish things at that point in my life, but with standup you had an immediate reaction to stuff. It just made me want to write and write and write and get better and better and better. It’s such an addiction so I took to it immediately. It was like a huge sigh of relief. It was like, “Oh, maybe this is the thing I’ve been missing my whole entire life.” I feel like up until my late 20s I did not have the ability to enjoy the life I’d been given. Standup really allowed me to have agency to enjoy my life. It was like a huge, “Thank you so much universe for giving me comedy because it’s kind of what I needed all along.”

How often do you get up now? Do you still do open mics?

Yeah, I still do open mics. I try to get up as much as humanly possible. I also have a sketch group so we meet a lot and we make things. My friends and I are workhorses when it comes to comedy. We do a lot of shows and we do a lot of mics and we are going to keep going until we literally can’t for good or bad reasons. The thing about it is I truly believe…There’s this Roseanne Cash book I think about all the time and I may fumble it a little bit but it’s like, “Talent does what it can.  Genius does what it must.” And I know that I’m not a genius so I feel I have to achieve the talent part of that quote. So it just means you have to maximize what you can. There are some comedians who are geniuses and they almost have this burden to do what they have to do. But if you’re talented the only thing you can control is how much you work. So I always feel like I don’t know how good I can get, but I want to make sure I’m giving myself every opportunity to get as good as I can possibly get. The only way to do that is to go up all the time, write, and think and get better. That’s one of my favorite parts of comedy is you can control how hard you work. You always know if you’re working hard enough. At first that seems like a huge burden, it’s like, “Oh god it takes all this hard work.” But no it’s like, “I might be able to control my destiny a little bit.”  It’s an illusion of control, but still that makes you feel safe.

Are you not working in the industry anymore? Are you full time comedy?  

Yes, well the last job I had before I started doing comedy I was working at a lighting store. Like really fine lighting – mostly European and chandeliers (I don’t know why I’m giving you all this information) and sconces (I had to learn what a sconce was to work there) – I worked there for almost three years and then I got a writing job (that was six weeks), then I left my job and thought I was going to get another one and I didn’t so the last year of my life has been barely making it as a professional comic. I’ll do gigs out of town or I’ll get writing jobs every once and a while on a random pilot or I’ll act in a sketch on a TV show, but I might get cut. All this weird stuff and I’m barely making it by having to borrow money and pay it back but hopefully in the next year or two it will be easier to be working full time. I’m working right now but I’m barely making it and I’m hoping the next year changes.

Montreal will help with that. I’ve heard people say even if you don’t have much of a safety net you just gotta go for it. 

You have to go for it. I’ve had to get weird day jobs in between things this year. This last year I had to do social media for a company in LA. I’ll do all these Internet writing jobs for a while and then once in a while I’ll get a great job that will provide me money for a while. But I feel there’s a thrill in going for it. Being like, “No, I’m going to achieve my dream of being a professional comedian and working entertainment as a performer/writer.” And of course you are going to struggle but you know there are struggles going in. But you’re like, “I’m going for it,” it’s such a fun time. Even though I have no money right now it’s really fun and I’m happier than I’ve ever been even without the money, which has been a great lesson.

I want to ask about your sketch team, WOMEN. Wait, is it sketch group?

I guess you could call it a group but team sounds weirder. You know why team sounds weirder?  Because team makes it sound like it’s a competition as opposed to a group is like a band where you’re just making what you make because you like it.

Good point. People who watch sketches online often don’t have any idea about how much work goes into making even a 45-second sketch. Do you guys have a set schedule? It’s challenging, especially when you have four different schedules to coordinate. How do you guys make it all happen?

It’s very challenging. You see we all do comedy not just as a sketch group. Dave (Ross) and Allen (Strickland Williams) do a lot of standup too. Pat (Bishop) does standup sometimes and he is also an editor. He was a writer, director, and editor for Funny or Die and now he’s an editor on the Birthday Boys. All of us are all doing this other stuff – freelance jobs and Dave was just on Drunk History and Allen writes jokes for a lot of things. But WOMEN is probably our favorite thing to do. We basically email every day and we try to meet at least once a week. We have a lot of things we are trying to get made. We are always calling, texting, emailing, and calling. Sometimes not all four of us can meet up but two of will meet up. There’s a whole bunch of work that needs to be done always so we just try to get it done all the time. It gets very challenging but it is literally the best thing to do. It’s the most fun I ever have so it’s worth it. And the way I feel about it is the reason you should work really hard because the difference is like on a Saturday morning when people are getting up from their hangovers we’re getting up and shooting all day or Saturday evenings. It’s like a seven-day workweek. We just try to work harder than other people.

That is our goal – to work harder and make as much as we can. I’ve always felt this way because it’s so fun but also if you do ever achieve your dreams and make TV, movies or whatever you want to do right now before you’re doing that (hopefully we get to do that and if not oh well) but this is the only time we have complete agency over our own material. So this is the only time before you achieve your dreams where you get to make exactly what you want to make.

Obviously there are budgetary concerns because there’s no money, obviously it be awesome to make some stuff with money, but no one can tell us what to make right now and I think people should realize that. Also I want to say that I’m stressed that I said, “We work harder than other people.” [Laughs.] I just meant that we try to work extremely hard because we think right now is the only time we’ll get the opportunity to really do that – like our schedules are getting busier so I feel you just push yourself harder because when else are you going to get to work with people you really love before people have families, houses, and that kind of stuff.

Okay I will edit that out, don’t worry. The quote will be, “Jake Weisman works harder than everybody. Everyone else is lazy.”  


What made you guys gravitate towards each other? There are probably a million guys in Los Angeles that want to do sketches together. How did these particular four guys come together? 

It is weird. I was talking about that recently with Dave and Allen. I’m not exactly sure because – well I know how it happened, but I find it weird that we all have a very similar sense of humor. We try to set a very specific tone of the kind of sketches we do and it’s almost a little crazy. I don’t know why we’re all the same kind of crazy but I do know in the simplest terms we basically all started comedy around the same time in LA. We would just go to open mics and at open mics you just go up to the people you like and say, “Hey great job.” You naturally gravitate towards each other’s company.

Dave, Allen, and I and eventually Pat – well we decided to form the group and then Dave got drunk one night and called me and Allen and said, “Here’s what we’re going to do. We’re going to make one minute sketches and we’re going to call the group ‘Women’ and we were like, “OK.” We didn’t even think about it we were like, “Let’s start doing that.” We started shooting on flip cam for a while because we just wanted to make sketches but we didn’t really know how to make sketches. We just wanted to make something different, I guess. We did that for a while, and Dave and me had been talking about stepping it up a little but we didn’t have a nice camera because we had no money. But then we thought of this guy Pat Bishop who was so funny and a really brilliant guy and I remember seeing him at an open mike and Googling him and seeing that he made a lot of videos. And his videos were so weird, funny, and so dark that I was like, “He seems perfect for us.” We emailed him and asked if he wanted to make a video with us and he said, “I really like what you guys do. I’d love to make a video with you.” Then the first video we made with him was called “New Camera” and he made it look really nice. It’s by far our best sketch to date. So we were like, “Do you just want to be in our group?” and he said, “Yeah.” Through open mics and doing standup I can see who I have a pretty similar sense of humor to and then you just start making stuff together because what else are you going to do?

Did he bring the technical side to it with editing and everything?

Oh yeah. It is the least talked about and probably the most important part of sketch comedy – having someone who is willing to direct and edit. Pat is a really amazing director. He’s an incredible filmmaker. When you have a filmmaker in your sketch group – visual jokes add so much to sketch comedy. Look what Peter Atencio is doing with Key and Peele. It’s genius stuff. It really elevated it to the next level because it’s so cinematic, it’s not just jokes. It’s a visual art form and you should think about it that way. I couldn’t have more praise for Pat as a comedic director, writer, actor, everything and editor. He’s just amazing and he’s a great guy too. He definitely helped us tremendously. He’s probably the most important part of our group.

My friend thinks that your “Improv” sketch is the funniest thing ever.  

Thank you. We actually shot that at a real show.

Yeah, I recognized that – Westside Comedy Theater.  

We didn’t tell the audience we were shooting the sketch. We were just like, “OK we are just going to go on stage and do this. They’re not going to have any clue what’s going on. But it will probably look good as a sketch on the Internet later.” So it kind of ruined the rest of the show because they were like “Who are these guys?” They didn’t understand what it was but it was totally worth it because I think the sketch turned out well.

What was the story behind that? Are you guys not big fans of improv?  

I honestly, man how do I be diplomatic? I’ll say it this way – it’s more of just a funny joke we thought of… The best improv is probably the height of comedy. I think the best improv is truly as delirious as you can feel as an audience member. It’s unbelievable. When I was in Montreal I saw the Improv4Humans podcast and seeing Matt Besser and John Gemberling and Zach Woods – they are so unbelievably funny and so good at improv I don’t think standups get funnier than that but unfortunately most improv is not like that. But the best improv is the funniest people can be.

You’re a triple threat. You excel in standup, sketch, and twitter. That’s a rare breed.

Thank you very much I appreciate it. It’s interesting. I think being a comedian now is different than it was 20 years ago because there are more opportunities to put yourself out there. Obviously we’re talking mostly about the Internet. You can do just one thing, like you can just do standup, but it’s harder now. People expect you to make more things and it’s fun. I think it’s fun. It’s a challenge but I like it.

The thing that I like about YouTube and Twitter is that (there’s always negative things about all that stuff) it can make you work harder. It keeps me thinking all the time, “What can I make now?  What joke can I make now? What video can I make now? What can I do? What can I do? Why am I wasting time? Lets do this. Lets do this right now. Lets make something else.” You don’t just have to do standup, you can make a video.

I love the opportunities for creativity now in the modern world of comedy. I think there are way less excuses to succeed now. If you’re not succeeding now than you’re either not working hard enough or you’re not funny. Of course people slip through the cracks but in general there are so many places you can be funny now and I think that’s good. You at least have the illusion of control over things. I think you do have control over things more than you think. If you don’t make it now, “Why not?” Everything is on the Internet you can get all the information you want – you can go up to open mics anywhere, you can listen to podcasts with the top comedians giving you so much advice, you can see how the most famous comics in the world are writing jokes every day on Twitter. You can see that and understand the form of it. It’s the best. I like trying to involve myself in all of it.

The Morning After podcast you did was great. I’m sad it’s no longer around but I’m sure you got a lot out of it and I know you guys explained you just needed to move on. Could you share a couple of the more interesting stories or just some of your takeaways from doing that podcast?  

That podcast I did with Eli Olsberg who is a comedian in LA. I also met him at open mics. We were both telling jokes about porn at open mics and they weren’t the normal jokes about porn, which is just super negative stuff about calling women whores and all this awful stuff, which is so hypocritical and terrible. So we started talking and he came up with the idea. He was like, “Why don’t we just start a podcast where we interview porn stars.”

Another thing is that we both also loved the movie Boogie Nights and even though Boogie Nights in some ways is a cautionary tale it also humanizes people in the adult industry. Both of us were always obsessed with porn but also the reality of porn. We both watched a bunch of documentaries about porn stars and their real lives and I’ve always been fascinated with my obsession with porn and the idea of sex. My mother was a Planned Parenthood volunteer so very early on sex was very normal for me and talked about. I also have a sibling who is gay so I’ve always felt that sexuality is talked about completely in the wrong way in this country and that sort of led to my interest in pornography and what that means morally.

We basically wanted to have a pro-sex feminist podcast. We are two straight men so maybe not ideal for this conversation but in some ways even better because the problem with how people talk about porn is mostly straight men and how they talk about porn. They’ll consume it and then call a woman a whore right after it. It’s the most hypocritical thing in the world. First of all we just thought what a trip it would be to talk to porn stars as comedians and also I really think it could change people’s minds. A lot of people have this thing about porn “It’s so awful and all of these women must have been molested. They all have daddy issues.” This horrible preachy bullshit and I thought if you talk to any of them for 20 minutes I guarantee you’ll feel different about the whole thing.  And I just felt it’s very anti-feminist, I believe, to be against porn and stuff like that and to believe that these women don’t have any agency at all. It wasn’t just women we interviewed. We interviewed transsexual performers, gay performers, male performers, bi performers, and we just thought let’s try to decrease the stigma of sex and porn in this country. There’s no need for it. There’s no need to be against something that these people enjoy doing. There’s just no need.

How did you go about finding guests?

It started with Deena DeArmond, who I’m still friends with. She followed me and Eli on Twitter, I forget why, so we just direct-messaged her and figured let’s start there. We started with her, and she really enjoyed the experience because it was the first interview she’d done where she wasn’t being terrible questions like what her vagina looked like. We were just like “hey, tell us about your life, tell us about your feelings, tell us about  you as a person.” That’s the problem with interviews with porn stars, they’re not looked at as people. After that we caught a lucky break. She called us and told us she was going to a birthday party where a lot of porn people would be and asked us if we wanted to come. So we were there at this bar in the Valley surrounded by people we watched have sex for years.

That had to be crazy.

It was so surreal. I was like, these people must know that I have masturbated to their naked bodies like this week.


But that’s just how they do it. We got some of their numbers and then we got them on, and then that got the ball rolling. They would text their friends and be like “These guys are cool, they’re not assholes, and they’re not a threat,” you know, because we’re both neurotic Jews. Eli was really good about contacting them. It was always a scramble, but it was always fun.

Any projects or goals you’re working on with your standup?

I want to keep doing a lot of standup and sketch and I would like to make TV shows so that’s what I’m gonna try to be doing in the next couple years, and I would like to get on TV for standup. Hopefully that will happen in the next few years as well. I basically want to do everything that every comedian wants to do. I want to write and act in TV shows, and I want to perform on the road, and I want to have a great time.

WOMEN hosts Comedy is Dead XVII on Thursday, Aug. 21 at Hollywood Forever in Los Angeles. The show also features Pete Holmes, Eric Andre, Joe Mande, Jerry Minor, and Kate Berlant.

Phil Davidson writes about, performs and produces comedy.

Jake Weisman and the Love of the Struggle