There’s no question I enjoy interviewing people, especially interesting ones. When I reached out to comedian Jordan Cooper for an interview, I wasn’t entirely sure which direction it was going to go in. We had a chat for a good long while, so strap yourself in, grab a cup of coffee, and dive right in.
Alex Knight: Just who the hell are you and what you do with your life?
Jordan Cooper: I’m just a visionary game changer out disrupting industries, thought leading the world towards innovating the future. I know, just like everyone else. Boring!
I once tried being a serial entrepreneur, but I ended up always pivoting 360 degrees. No product-market fit, of course. Now I’m working on my startup while starting up my workout. Treadmill desk, you know?
Although we’re in drone mode now (which is even more secret than stealth), I can tell you it’s a photo sharing app. Ephemeral. Whatever that means. Poof! The idea is gone. Should’ve had everyone reading this sign an NDA.
Oh, I also run a choose-your-own-adventure capital fund. Go to page 38 if you’re interested.
But seriously, folks. I’m a journeyman stand-up comic and web designer, doing both for about seventeen years. Sarcastic as fuck. Brutally honest. Without empathy. A righteous douchebag. That’s why I work for myself. Perfect company culture fit.
Alex: How did you get into comedy? Did you realize at a young age that you could make people laugh? Who inspired you, and were you influenced by any family members that had a sense of humour? I’m also curious about your entrepreneurship. You’ve been building a business and name for yourself for quite some time. How does this blend with your pursuit of a standup career, or do you even consider that a possible career you could do full-time? Is there a certain transition point where the light bulk goes on and you think, “yep, I think I could make a living from this? But should I??” What do you consider an acceptable risk when switching paths?
Jordan: Coming from a Jewish family, it’s a fait accompli to have a good sense of humor. We’re not going to be the star quarterback or the muscle car-driving chick magnet, so it’s our keen, clever jokes that garner the respect and attention of others – even from your parents as a young kid. A hearty chuckle at the dinner table from adults always boosted a self-esteem more than shitty finger-paintings posted on the kitchen fridge.
This was especially true since my parents were both naturally funny people. My dad was even in an improv troupe. I remember watching them rehearse in our living room and offering the audience suggestions as well as an eight year-old could. Of course, I barely understood much of what was going on, but between that and listening to my parents’ comedy record collection – comedy was something I pegged in my mind of wanting to do in some capacity.
It was these albums from greats like George Carlin, Robert Klein, Woody Allen and Bob Newhart that really shaped my understanding of structuring jokes and becoming a student of the art and science of writing humor. Not how to be funny, but why something is funny. Anyone can be a natural hoot and have that spontaneous wit, but being the math/computer geek that I am, the more interesting pursuit was the deconstruction and optimization of comedy.
What assumption is being set up in this premise? Who or what is the target of this joke and its relationship to the audience? How hidden or obvious is this punchline the way it’s currently written? Sure, there’s no definitive equation to “funny”, but my creative mind works best where there is some amount of formulaic concepts that apply nearly across the board. For the web folk out there, it’s like the difference between visualizing and mocking up a beautiful design and actually coding it with HTML, CSS, and so forth.
Speaking of web design (yes, a cliched stand-up segue)… I’ve been doing that as long as I’ve done stand-up: about 17 years. Worked in the financial sector during the dot-com boom of the late 90’s, did some long-term contract work for a few major entertainment/information outlets, and essentially freelancing ever since. I hate the term “serial entrepreneur”, so I’ll just describe myself as “narcissistically unemployable”. Unless I actually enjoy the subject matter and/or have some ownership in the business or work that I do, it’s not going to get much effort from me. That probably also explains my progression from starting out with acting, moving to improv, and then settling on stand-up. I hate other people.
Oh, and I’ve done the full-time stand-up thing. It was the main reason why I moved from New York City to Louisville in 2007. It was a centralized location in the Midwest with a much lower cost of living that has about twenty different comedy clubs within a five-or-so hour driving radius. For the next three years I kept my calendar fairly full traveling anywhere and everywhere from frozen ponds in Wisconsin to biker bars in Georgia.
Although it sounds like “living the dream”, the pay as a professional feature comic is barely above the poverty line and still very feast and famine. To supplement my income, I continued with freelance web work as it’s able to perfectly fit in with a nomadic lifestyle. Most weekends I’d spend designing and managing sites on my laptop in a shitty motel room by day, while making drunk rednecks laugh on stage by night.
Eventually the web stuff became so much more lucrative as road comedy stayed the same, and it felt like spinning on a hamster wheel with no distinct destination. That’s when I started staying home more, accepting only stand-up gigs that were either better, well-paid, or simply more convenient to do. But since I still had a narcissistic need to have a creative outlet, that’s where the blogging, vlogging, tweeting, podcasting and whatever else I felt like producing came to be.
As with anyone that pursues this online shit, I started something, quit it a week later, tried something else, changed it around, pivoted here and there – all under the desire to be validated, to be popular, to have a “successful” site – whatever any of that means. I fell into the trap of actively trying to get to the “transition point” as you’ve stated. It doesn’t work. If you’re reading this and are thinking “Well, I’m not him. I’m special!” Yeah, good luck with that. You’re not special at all. No one cares about you. Seriously. They don’t.
The positive takeaway, however, to that type of cynical realization is the freedom to do whatever you want. Write. Don’t write. Have a flexible schedule. Post intermittently. Do a video. Host a podcast with any format you’d like. The only person who gives a fuck is you, so just aim to please that audience of one. In the process, you’ll likely find others who resonate with your natural voice and start building that community of “fans”. Will you be able to follow your passion, quit your job and make a full-time living with it? Maybe. Probably not. But especially if you already have a sustainable source of income elsewhere, why burden yourself with the pressure to derive money from it at all? If it happens, it happens.
Alex: Most of your life experiences echo mine, and those have been some very challenging times to overcome. With challenge comes pain, and hopefully you can push through that uncomfortable period and learn something. It’s tough and I’ve found it easy to slip into old habits. I’m getting better and feel like I’ve started to take control over my life and what I want to do in general.
In the beginning when I started writing, I knew I liked it and wanted to continue to do it. There was always something to say, but because I didn’t know the best way to run a blog, I quickly looking to other people that were doing it well. Those people were already successful and had built an audience. I tried replicating what they were doing, but after about a year, I got burnt out. I remember feeling like I had wasted my time, that I wasn’t being true to myself.
It took years of iterating through writing to get to the place where I felt like the words on the page were really “me.” And yes, I did do the Daring Fireball linked-list thing at one point — I’m pretty sure most did. About a year ago I started a different weblog because I was nervous, yes, nervous, about alienating my readership if I dared stray from the usual topics I discussed such as technology and design. I don’t know if it was deep introspection or just bitterness from doing it for a while, that I just said “fuck it, I’ll write whatever the hell I feel like. If they don’t like it, they can click the back button.” This was a pivotal and incredibly liberating moment. I haven’t looked back since, still write about whatever I feel like, and the readers keeping coming back. In fact, my readership has grown.
Do you think people can truly sense authenticity, be it through the written word, or perhaps aurally through other mediums like podcasts? What is it about someone that makes them authentic, and how do you quantify that? Moreover, how do you fine “authentic?” This is a word that gets thrown around a lot as advice to the less experienced — “just be authentic and you’ll be fine.” I posit that there are those that don’t know where to start, and perhaps don’t even know how to be themselves. The pressures placed by peers and what society deems as acceptable bears a great weight on many. I’ve known people who’ve stumbled through life not even being cognizant of their own personality. How do you over come that? Is it even possible?
Jordan: Well, I think a lot of folks go down the wrong rabbit hole, in anything they pursue, in any aspect of their life, due to selection bias. “If I take the same path and do the same things that this successful person did, the same result should occur.” Of course, because you’ve eliminated all the others who failed with the same process – because you never hear about them — it creates a very high false sense of confidence and expectations in your endeavour.
I believe this is the root reason why so many writers, bloggers, podcasters, or people in general quit things after a short period of time of getting very little positive feedback or traction. It’s thinking in terms of being the “next X” and looking more at the current culmination of their hero’s body of work, rather than building the foundation of being the first themselves. Between a mix of selection bias, high expectations and unwillingness to risk investing a long amount of time in something that very well may not succeed at all, it’s a toxic brew that hinders any possibility of achieving the same result as your hero.
Hey, it’s the way our human brains are wired – to seek patterns and relational causes for why an event happens. Most of the time, though, there isn’t any reason. Right place, right time. Dumb luck. Complete randomness. These types of things can never be recreated, so it’s a fool’s errand to fight against the inherent unfairness in how the world works. You can do everything right and still lose. You can do everything wrong and still get to fuck the prom queen. The only part of existence that can be controlled is yourself. And if success is basically random anyways, why not just do what you want?
This “who gives a fuck” attitude may sound like a very cynical view of life, but I consider it an extremely optimistic position. Once you free yourself from the notion that your life is meaningful, that what you do impacts the world, that you’ll be remembered a hundred years from now, or that anyone currently is thinking of you at all and judging everything you do – that opens up a world of possibilities where you can spend your short time on this earth without much worry, stress or fear.
People blow the smallest of adversities up out of proportion, when in the grand scheme of things, it doesn’t matter much what the outcome is. In the same regard, they’ll overestimate the importance of specific events or occurrences when, in fact, it won’t impact the course of your life much at all. So why consume your time over these situations? The mental effort wasted in these relatively inconsequential decisions could be better spent doing whatever you want that makes you happy. In a logical sense, no one can ever blame you for that.
This fairly narcissistic concept ties well together with what authenticity really is. Being who you are, nothing more nor less. From a purely theoretical view, this might not even be possible due to the observer effect. Just the mere fact that there’s another party present, whether it be speaking in-person, a blog reader, podcast listener or simply a stranger walking on the other side of the street – we will change our behaviour (many times subconsciously) in order to present the most acceptable picture of ourselves based on the company and surroundings. Even if it skews positive, it’s a form of human deception.
The funny thing is, we also are somewhat cognizant of this shift in nature, both in ourselves as well as in others. It’s this awareness that causes us to gravitate towards, put trust in and respect those who seem to exhibit no deceptive markers in their behaviour — regardless if we might not agree wholly in their actions, opinions or resonate well with their personality. We know they can alter, tweak, and water down their presence — because that’s exactly what we lie to ourselves about all the time – but it’s that this person chooses not to. They’re not wearing the mask, the fake smile, the false cheer that we’re so accustomed to being weighed down by — hence why it’s perceived as a very admirable quality.
On the other hand, however, many are scared by authenticity. They’ve spent their whole life obfuscating their true nature under the notion that if anyone saw who they really were, they’d be vilified. Hell, they might not even be who they really are to begin with. Hence why many have a visceral reaction towards those who aren’t afraid to express unpopular opinions or societally unacceptable behaviours – either negatively through condemnation, or positively through silent agreement.
Venturing into stand-up comedy, I’m on the front lines of this psychological and sociological battle. It’s our jobs, essentially, to say the thing that everyone’s thinking but are afraid to say. That’s the “ground zero” from where laughs come from. The collective release of tension and communal acceptance of a viewpoint considered taboo, unbecoming, or not outwardly expressed in polite company.
That’s why it takes a decade or two in comedy to truly “find your voice” as it’s called. Fighting off the natural urge on stage to please the audience, or in your material to sculpt a false caricature or style that will be more likely to get a positive response. Shedding all preconceived notions of what the “correct” way to do things is. Learning how to express your uniqueness, flaws and all, so that others can effectively understand your worldview — not what you think, but the why of what you think. Mastering this craft, this persuasive prose, will enable even the biggest detractors to come onboard while attracting a hardcore following of those who highly resonate with the context, themes and messages you convey.
It’s not as simple as the advice trotted around to “just being authentic”. There’s no on/off switch that you can flick. It’s a constant struggle. Stopping whatever it is you’re working on content-wise to ask yourself: “Am I writing this because it’s what I think… or am I writing this because it’s what I think what other people want to read?” Even if it sometimes is one and the same, there’s a big difference between being genuine and appearing to be genuine.
For instance, I know very well that my incessant use of swear words on my podcast can turn many people off. Hell, I’ve got plenty of e-mails from listeners the past year or so expressing that very fact — in a non-hateful, constructively critical way. If I wanted to, I would have no problem ceasing my four-letter word affliction. Even my regular stand-up act is fairly sparse of expletives. I choose not to, specifically for my podcast, blog and Twitter, because I find it’s the most effective technique for me to be truly honest with my thoughts. That I’m consciously giving myself the freedom to speak without a filter, not to overthink what’s coming out of my mouth, and blocking the instinct to censor feelings for the sake of appeasing others.
It just so happens that this process results in a metric shit-ton of vulgarity. I chalk it up to being a New York native, a blunt east coast type, and also not having much emotional maturity. Instead of having any type of nuance with my tone, I’m used to just being abrasive and direct for the sake of being taken clearly. My emotional dial only has a few notches on it and you’ll know exactly which one by the words I choose to use. The shortest distance between two points is a straight line, right?
At the end of the day, I never cared about being liked. I just want to be respected, understood and be regarded as a person with his own sense of personal integrity. That’s why I view it as a compliment when someone would say “that Jordan Cooper’s an asshole… but at least he’s honest.”
Alex: I feel like you have succinctly summarized most of my teenage years and early twenties. Effectively most of us have, and most likely will, continue to go through life with some amount of trepidation of how people will truly understand or perceive us. Even the slightest amount of apprehension could mean the difference between showing people your true identity, or putting on a facade.
Ever since turning 30 back in 2012, I have found that with each passing year, the concern that someone won’t like me for who I am melts away like an ice-cream cone on a mid summer’s day. I initially surmised that my feelings and expectations aligned with an overwhelming amount of the population that’s my age — I was wrong. It seems that I encounter more and more people ever day — some acquaintances, some friends — that still refuse to be themselves. It’s always that you have to “dress to impress,” or do your hair a certain way. I have felt first hand the pressure of people around me tell me that as I get older, I must start “looking my age” if I want to get anywhere. The amusing part is, I’m more well paid and successful than I was 10 years ago. You know what my secret weapon has been? Just being authentic. I present myself how I feel most comfortable, and yet I believe that ultimately translates to more self confidence. I have shed all expectations like an old skin, never to return again.
Oh, and just as a “fuck you” to anyone who doubted me, when I turned 30, on a whim I had multiple piercings put in, died my hair, and started wearing converse sneakers. I figured, this is going to be a fantastic opportunity to weed out al the assholes that I don’t want in my life. I choose my relationships, my friends, and I certainly choose whom I wish to work for. Employment is a two-way street. I’m convinced most people aren’t cognizant of this. It’s always about making the best impression and trying so desperately to appease your prospective employer — your own requirements be damned. In my mind, there’s nothing more toxic than this kind of self destructive behaviour. Dealing with people this way is a sure fire way to landing a job you hate, but won’t be able to get out of for years because you like “security.” Meanwhile, you keep bitching to all of your friends about how much life and work sucks, as if you’re a prisoner, shackled and chained to your desk.
I suppose everyone wants, in some way or another, to please other people — to be liked. Arguably the fairest and easiest way on yourself is probably to just accept yourself and move on. As previously discussed, it can be exhilarating to embrace your true identity. It sounds like in many ways, for both of us, it’s made things easier on us. Touching on your example about fighting the nerve to please the audience, there is a bit of an adrenaline rush you receive from that approval, but I would be willing to bet money that it feels even better when that laughter just comes flows in from you being who you really are. Whilst I’m no stand up comic, I do like making people laugh. Often times the best rewards I’ve received were in situations where I wasn’t trying hard to please anyone, I just started saying things and people laughed. To me, this is always the most fulfilling.
Jordan: Well, of course, no matter how adamant I may be towards projecting a seemingly natural “who gives a fuck” attitude, there will always be an subconscious part of the psyche that ultimately, wants to be liked. I just think the difference between the stereotypical people-pleaser and the authentic individual is purely philosophical. The former sacrifices one’s values and feelings for the sake of conforming to perceived norms. The latter attempts to bend one’s environment to his/her will so that no internal sacrifice is made. “Like me… but on my terms, not yours.”
At the end of the day, however, no one will ever care about you, your work or your creative output more than you do. When I first started in stand-up, I used to watch recordings of my sets, analyze them to death and would end up kicking myself for the smallest of mistakes, missteps or performance quirks. Little did I realize, though, that no one noticed these things besides me. The time I spent trying to quash marginal errors and tweak every joke would have been better utilized churning out more primary source material and keeping the natural creative juices flowing, perfection be damned.
See, you may be able to tell the difference between a B+ and an A-, but others viewing your work will judge it in only whatever capacity they can, and even more importantly, only based on the aspects they value and nothing else. It’s similar to the tech douchebag trope of “only my use case matters” — but it exists for everyone and extends to all areas of life. People don’t care about you. They care about what you provide to them.
I know that may sound Ayn Rand-ian and a very cynical, depressing way of living your life — but to me, it’s inspiring. Why work so hard trying to be liked, pursuing things you don’t enjoy, and impressing people you don’t respect when none of them really give a damn either way? Do what you want then. You’ll be much happier, I’m sure of it. No more stress weighing you down in every decision you make because of the concern of what others think. Fuck ’em.
So, is this the point where I pitch my smarmy motivational seminar at the Marriott and bullshit life coach training DVDs?