WTF Is an Entrepreneur?

08.05.10 | 21 Comments

CATEGORIES conversation starter, ideas, rabble rousing, theatrical ecosystem

“I think that artists are, in fact, small businessmen. They’re entrepreneurs.” Rocco Landesman in an interview with Bryan Reesman in Stage Directions August 2010 issue.

I’m serious about the title of the piece. Look, I trained as an actor and a poet. (Yes. Honestly.) When I was in school I was learning all I could about analyzing text—whether that was to make sense of a T.S. Eliot poem or a Chekhov play so I could act it. Either way—that’s what I focused on.

Which is not to say I’m fiscally ignorant—I also took the requisite econ courses, I know how to balance a budget. I have a prudent cash reserve. I know how to forecast earnings, save for expenses, etc., etc.

But I still don’t think I think like an entrepreneur. MORE distressing to me—I’m not even sure what that means. How DOES one think like an entrepreneur? What are the qualities of an entrepreneur? Do I already possess them, and simply don’t know how to act on them? Do I not view my circumstances in an entrepreneurial way? How can I change that?

That’s the big thing for me. How can I change that? How can I begin to think entrepreneurially? (Or even recognize when I am?) And this isn’t just because Rocco is harassing every artist out there to be an entrepreneur—because he’s not harassing us to become something, he’s saying we ALREADY ARE. So what about my current behavior is entrepreneurial? Because if I want to succeed as an artist (and I do), then theoretically I need to learn better, more successful tactics of behaving entrepreneurially.

So I did the first thing I always do when confronted with something like this. In my finest analyze-the-text tradition, I went to the library. I checked out a bunch of books about starting a business and becoming an entrepreneur. Most of these books had a section that listed the “qualities” of an entrepreneur. (One of which was “impatience”—if I disliked waiting in line, I might be an entrepreneur. Maybe, but that’s also the character trait of a petulant child. How does that translate into running a successful business?)

One thing that did stand out to me in all the lists of entrepreneurial traits was the idea that entrepreneurs A: Always think they’re right and B: Have a need to be in charge. And that got me thinking about all the small theatre companies that have popped up everywhere. How many of them were formed because of dissatisfaction with current offerings in their community? How many times have I been tempted to start a theatre company to show people how it’s really done? Unfortunately, I’ve never been able to get over the hurdle of expenses in operating a small theatre company. I don’t want to risk that much of my money in what is, essentially, a losing venture. (Not that this is unique to theatres—how many small businesses fail within the first five years?)

Which brings me to another trait of entrepreneurs: Risk-taking. There are actually a couple different schools of thought about this. Some people say that entrepreneurs have a stronger stomach for risks. So, at first glance, my inability to risk starting a theatre company precludes me from being an entrepreneur. But other people take issue with the idea of risk-taking. They say entrepreneurs aren’t any more likely to take risks than anyone else—but that entrepreneurs HAVE carefully weighed the risks, and developed a solid-plan for success based on research and observation of past failures and successes. In other words, they take very calculated, very measured risks—risks that have a high chance for reward. So what makes a successful entrepreneur is not their gung-ho, damn-the-consquences attitude to risk taking, but actually their preference for risk aversion. What makes a successful entrepreneur is someone who actually hates risk, and will do everything to minimize it. Penn Jillette (of the famed magician duo Penn & Teller) originally didn’t want to be a magician. He actually wanted to be a rock musician. But when he surveyed the field he saw that the number of people applying to be a rock star was HUGE (duh) and that it was filled with absolutely incredibly amazingly gifted talented people, which he could never compete with. Then he looked at the field of magicians. And saw two or three people. He decided that field had a high ratio of reward to risk, and took it.

One thing that everyone seems to agree on is that passion plays a huge part in successful entrepreneurs. If you don’t have a passion for the field of business you’re entering into, you’ll never survive. And that doesn’t take any translating into the theatre side of things.

So what about you? What traits are typically entrepreneurial in your view? How can they be applied to theatre? Tell me how can I sharpen my entrepreneurial thinking!

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Jacob Coakley

Playwright and editor of Stage Directions magazine. You can find me on Twitter as @stagedirections

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  • maxepunk

    Jacob, I think our stories are quite similar (Theatre and Philosophy for me, but textual analysis is still the game!), Over the past 6 months or so, looking back on my career, and doing my research on what this entrepreneurship thing actually is and is not, I've been seeing that yes, I suppose I've always been following an entrepreneurial streak, creating my own projects when not working for someone else, consulting for others, looking to create my own game. So i suppose in a nutshell that about sums it up, it's that instinct to create your own game, to live life on your own terms. And I believe all artists, in theatre or not, have that instinct. Perhaps entrepreneur and artist are different outlets for a similar need. If that's the case, we can all definitely benefit from learning each other's language.

    there's a great Ted talk about raising kids to be entrepreneurs, check it out, sums it up pretty well, I think: http://www.ted.com/talks/cameron_herold_let_s_r

  • What a great question. I don't have enough experience to suggest a definitive answer, since I don't know enough entrepreneurs and am very young in my own entrepreneurial endeavors. But I'll submit the following as possibilities.

    Good entrepreneurs:

    – Are obsessed. Which is not to say they must live unbalanced, over-worked lives, but that they are drawn back again and again to their interests. They can't not think about them.

    – Are confident in their ability to analyze their circumstances, and work their way toward a good path — which is distinct from believing that they're always right.

    – Don't take any big risks, but do take lots of small risks.

    – Spend a lot of time engaged in “design thinking”.

    – Understand that there are very few real rules.

    – Have no patience for shitty rules.

    – Channel discontent into creativity.

    – See money only as a means toward an end.

    – Relentlessly seek deeper understanding of their domain.

    – Relentlessly leverage what they already have.

  • Thanks for the excellent Cameron Herold TED talk link – hadn't seen it.

  • Happy to see this conversation on 2AMt, Jacob.

    In my 40 years in the professional theatre, I've accumulated a lot of experience on this subject. In my opinion Rocco is correct, yet the E-Question requires a paradigm shift for many artists. I’m an entrepreneur, and 20 years ago would never have imagined using that word to describe my career.

    Check out the Kauffman Foundation in Kansas City, the impressive organization devoted to supporting entrepreneurship. http://www.kauffman.org/Section.aspx?id=About_T

    And I’d love to talk to you about YOU as an entrepreneur!

  • Can I just say “I agree with my wise friend,” and leave it at that?

    My only concern about comparing artists and entrepreneurs is this: the most successful entrepreneurs focus on the value they provide their customers (or, in our case, audiences). They trust that the rewards (monetary) will arrive. Weak entrepreneurs, however, are focused on making a profit — on how much they can earn. I wouldn't want artists to fall into that trap. I don't think it's likely, but I mention it here nonetheless. Never put balance sheets before the product. Have them, but keep them in reserve.

    Oh, and I trained as a poet, but work as a playwright. Same story.

  • AD

    Starting a nonprofit theatre company doesn't have to be a financially risky endeavor for an individual, unless you are talking about opportunity cost in foregoing other possibilities. Smart theatre entrepreneurs typically spread the financial risk to anyone who will bear it–many small stakeholders can insulate the company financially without feeling a significant burden, and their emotional return on investment can be a powerful engine for a company (particularly one that does exciting work) for a long time to come.

  • I think the difference between being an entrepreneurial artist and just an artist is the difference between having control of your career, and staring at the phone waiting for it to ring.

  • Thanks everyone for your comments! Keep 'em coming!

    @Maxepunk – “creating my own projects when not working for someone else” — I think that has a LOT to do with what being an entrepreneur is. Very much like what @Tony Adams says later, having control of your career or staring at the phone. Taking the initiative to move your own career, or your own passions forward by your own steam. What I *do* think we need, though, is more creative thinking around how to do that. The stock answer anyone gets when faced with not getting roles, not getting their work produced, not getting gigs is “Well, start your own company.” And I'd like to think there are more answers than that.

    I'd like to know how to think of these different opportunities, and analyze them, and come up with plans to enact them — that's a practice that's unclear for me. Brainstorming, OK, I can do that. But what goes into analyzing a plan? That's a skill I really want to acquire, as opposed to relying on “a hunch” or “my gut.” Sometimes that's well and good, but I've found that “my gut feeling” is often based on (only talking about myself here) some VERY faulty assumptions I didn't even know I had.

    Maybe I'm placing too much aspiration in the idea that entrepreneurs know how to interrogate their own assumptions, think strategically, and analyze their own plans.

    So I guess I'm agreeing with @Chris Ashworth, above, when he says “Are confident in their ability to analyze their circumstances, and work their way toward a good path,” but would also had a healthy dose of “Spend a lot of time understanding money and how to make it, so they have it as the means toward the end they care about.”

    Those are two skills I need help in, which means I also appreciate what @AD says, too, about spreading the risk among many small stakeholders.

    @Ann Sachs — thanks for that link! I'm definitely going to check the Kauffman foundation. I'm glad you swung by — I was going to DM you today to get your thoughts.

    Lastly, @Gwydions, I am *Definitely* of the school of economics you refer to here — “What value can I provide? What can I give?” I don't want to underestimate the value of balance sheets, but the idea of providing something is deeply inherent to philosophy of economics. Every deal should be win/win. I don't think predatory business practices help anyone. (Which is not to say I don't understand that negotiation is an important art. Add that as another skill to improve…)

  • Thanks for the TED link — and a philosopher, huh? I used to laugh at philosophy majors. Until someone pointed out the fact that I was studying poetry. Then I just cribbed the philosophy students' reading lists. 🙂

  • I love the post and the conversation here. It's something I've dealt with myself.

    I'll be honest, my theatre company exists in part to make the best of where I am right now. We started it because, at the time, there were a number of professional theatre artists living in the area, and all of them had to travel in order to work. There are fewer of them here now, but we're still here. And we program a balance of what the community wants and what we'd like to do, which has worked nicely so far.

    But I can't just be a playwright or a sound designer, I also have to put on my Professor Harold Hill hat and sell the thing. If I want it to grow, I have to beat the bushes. I work in marketing anyway, and it's all part of what I do for others, but at times, it's been hard to do it for myself. (I'd like to think I'm getting better about that nowadays…)

    I think part of being a good entrepreneur is recognizing opportunity. Locally, it was in noticing not only the amount of talent available, but also how underserved this part of the state was in terms of the arts. Certainly, there's been an element of that in developing 2amt.

    And part of it is being brave with your ideas. There was a time I'd think of an idea, then think, gosh, it would be really smart if someone did that. Now, I step forward and say, hey, here's an idea, why don't we try it? Some are good right out of the box, and some are improved by the people I work with. But they won't go anywhere unless I open that box and bring them out.

    This site is actually a pretty good box…hm…

  • This site, I would think, is a fantastic example of exactly what we're all saying folks should do. I admire the heck out of you for having done it.

  • Lisa

    Interesting post, but you can't learn how to cultivate an entrepreneurial mindset from a book. I see your struggle to figure it out as a result and admire your earnest effort to.

    But the reality is developing an entrepreneurial mind is a lot like how you learned how to create your art form- with the regular guidance of a highly skilled teacher and mentor over a period of time whom you admire and trust.

    Having worked for more than 20 years to help artists develop their own entrepreneurial abilities, I can tell you it takes about two years of effort, at a minimum, to begin to regularily think like an entrepreneur.

    Lisa Canning,
    Executive Director of The Institute for Arts Entrepreneurship

  • Brendan McCall

    Hi Jacob

    Thanks for posting this blog about “WTF is an Entrepreneur?”. I got it forwarded to me from a colleague, and I´m happy to throw my hat into the ring for this topic of conversation.

    I´ve been doing performing arts for over 25 years (directing, acting, choreographing), and it is only lately that it seems “entrepreneur” and “artist” have been linked in a lot of public forums, from conferences and blogs to news articles and conversations by the proverbial water-cooler (whether it be virtual or actual).

    One thing I´ve noticed in these conversations is how “the arts” are grouped together, as if each discipline and art form has the same process, expression, form, impact, economic potential, social value, marketing strategies, popularity, influence, etc. A novelist´s art form is nothing like that of a stage director, nor is a composer´s the same as that of a choreographer or a sculptor´s or a puppeteer. I applaud you for focusing your lens on theater, which is ironically so prevalent and yet so under-represented in the broader “arts & entrepreneurship” conversation.

    Music and visual arts tend to get a lot more press–usually centered on how many musicians, bands, composers, painters, designers, sculptors, art galleries, photographers, and more are “forming small businesses”, and taking more control of their careers. Part of this may be due to the fact that there is a tangible “product” that audiences / consumers can buy, which is not the same for a choreographer or a stage director or a dancer. I mean, how do you “buy” something that is a performance? By definition, the experience is just that: an experience, something transitory.

    Yet, within theater, we must also be more specific about the kind of theater we are speaking about. Broadway has a different kind of experience that it is selling than Off-Broadway, of course. And theater in big cities like Chicago and New York are different than, say, New Orleans, Oregon, Wyoming, New Mexico, Alaska. What are the links of all of these organizations, both as artistic entities as well as business models?

    For my part: I lived and worked freelance in New York City for 18 years, before moving to Norway 2+ years ago. I still travel between the US and Europe a lot, but my “home base” is different. I have seen a number of interesting things that may contribute to the dialogue that you´ve got going here:

    1) One refreshing thing about the linking between “entrepreneurship” and theater, is that it is a positive “wake up call” for many artists today, particularly those that are just entering the profession, or who are contemplating a career as an actor, director, designer, playwright, and so on. This emphasis on “entrepreneurship” as part of a larger conversation in the US theater community is good, because it dispels the old illusion that “if ya got talent, you´ll make it, kid.” Gone are the days when actors could just hop from one part to another, where everyone could get an agent, and where actors could get “discovered” if they just “got a hit show.” Unfortunately, that is extremely rare, and it´s a taboo subject for many Drama Departments. It is heartening to see that more and more programs (both for students as well as for working professionals) are getting more information on how they can be more self-directed, more independent, more pro-active in their careers. Rather than simply auditioning, for example, why not form your own theater company with a collection of colleagues? Or, if there are no good parts for you that you are auditioning for, why not write your own play or screenplay? If you are not getting hired to direct a play, put one up yourself. And so on.

    These and more tend to be cited as examples of “entrepreneurship”. However, 40 years ago, we called it DIY: Do It Yourself.

    2) The DIY / entrepreneurship conversation in the (performing) arts is linked, I think, to another taboo subject: lack of material resources. In short: as you alluded to, theater is expensive to make, and there is not a big financial return on the investment. So, why do it, in this uncertain age? Why be crazy like that? So, rather than provide more resources at the city, state, or federal level, one could argue that the conversation is turning towards artists to “be more entrepreneurial”. Rather than find more ways to support arts in the community, individual artists–many of whom have struggled and sacrificed for years–are now being told, “Hey: be resourceful, think outside the box, be creative.” This may sound a bit cynical. But think about the source of the individual (Rocco Landesman) whose quotation started the conversation: is he representative of the theater community in the US?

    It would be fascinating to find a way to gather more data about theater in different regions of the US: analyze how many theater companies are in which state, what kind of work they do, who are the successful ones (and how is success defined and measured), as well as how much support they receive from public support (ticket sales, products, investors) and private support (foundations, grants, contributions).

    3) In Scandinavia and Europe, the model is quite different than that of the US. Here, performing arts are very regulated: there are a handful of “institutional theaters” sponsored and supported by the gov´t, with RIDICULOUS budgets, by American standards. And there is a limited selection of choices: you have a national theater, you have a “international” theater, you have a “playwright´s theater”, and so on. But you don´t always find a very dynamic “underground scene”, because there simply are no resources for it. To be independent here is really a strong choice, not just artistically but politically and socially. It runs contrary to the traditions of “old Europe”. I mean, if you didn´t get into the “national school for drama”, which is where the actors are picked from to join the union and be in the institutional theaters…well then, you must not be good enough to be an actor, right?

    However, this mentality is starting to shift, and so it is an interesting time here. Europe´s cultural homogeneity (in places like Scandinavia) is starting to shift, and consequently there is an increasingly diverse population. Oslo, Norway´s capital, for example, has 25% non-native Norwegians in its population. This is a strong number of people, and its effect is being reflected (slowly) in its education, its arts, its politics.

    Plus–Europe, like the US–tend to be conservative during times of economic crisis, like we have been for the past few years. And unfortunately, the area that gets hit initially tends to be the arts. This is true here in Norway, also. Artists are having to learn how to make the work happen, no matter what. Not an easy position, when the community at large thinks that such a notion is LITERALLY foreign, an “American thing”.

    Many Scandinavians admire the “possibilities” of American artists, and how they can “seemingly do anything.” However, there is also a misunderstanding here, that all theater in the US is profit-driven. The distinctions between not-for-profit theater companies vs. for-profit is unknown to many here.

    In contrast, many of my American colleagues romanticize Europe, believing that “all art is supported on the other side of the pond”, and portraying life here as somehow utopian. This is not the case, either. There are many, many artists in Europe going thru the same convulsions that their American counterparts are doing, just from different origins and contexts. New organizations and alliances are being formed, new committees are being established to find new ways of funding for the arts, new collaborations are being formed. We all have problems, just different variations. And Eden always seems to be “over there”.

    In terms of theater education, I have been dedicated to contributing more business into my arts teaching wherever possible. While it may sometimes get tricky with students, as they often feel that talk of money is somehow a “killjoy”, I think it is vital to preparing them for a successful career. Performing artists, to make it (in my opinion), need to exercise both hemispheres of their brain constantly. And enjoy it, have a taste for it.

    This autumn, I am creating a 14-week program that will work in Oslo, Chicago, and New York with a small group of international students. To date, most are Norwegian, but it is open to students from around the world (the language of instruction is English). During the course, they will learn how to work “entrepreneurially” as a group and as an ensemble, not as an individual, which I think is a key ingredient for a successful theater company. Rather than leaving the responsibility of the company´s future to the Artistic Director or the Board, why not have every member be invested in the company´s direction, quality, labor, etc?

    The program also offers courses in Acting, Playwriting, Directing, and has a number of performance opportunities for their own work, as well as in a couple of planned productions (intentionally of varying styles and aesthetics). We are reaching out to professional artists who are working directors, producers, playwrights, and actors to teach master classes during the 14-week period.

    I´m calling it Ensemble Free Theater Norway, and its total tuition is less than $5K for the entire fall.

    If anyone is interested, feel free to contact me at brendan.mccall.norway@gmail.com

    Thanks again, Jacob, and to everyone who posted! I think this is a wonderful dialogue, and I have forwarded the link to your space to my EFTN students.


    Brendan McCall
    Freelance Theater Artist

  • I have recently started working toward making my freelance art into a business. I feel that unless I begin to think like an entrepreneur I am going to burn out because my art wouldn't be able to support me sanely.
    I recently purchased an e-book for freelancers from http://chrisguillebeau.com/3×5/ I recommend it. One of the best lessons in it is the need to divide your energies up and approach tasks as a Marketing director, personnel director, executive director etc. I don't think that we have much of a danger artists loosing sight of why they do what they do. We are in danger of loosing talented artists to burnout and financial stress.
    I am entering my forth year out of college, I work in a field that is less competitive (props), and I am just starting to get things in order. It would have been very easy to fall through the cracks in those four years and have come out as a teacher or an office worker or any other stable professional. I think it is great that this resource is here and that we are talking about these things. I think that the next step is to get these ideas into the schools so we can plant healthy ideas about money and art sooner.

  • Brendan McCall

    Hi Jesse–

    Great to read your post, and to get a glimpse of your blueprint for your life outside of the university in the field of props. I appreciate the link to the book that you recommend, and will check it out.

    I would only add a comment about “falling through the cracks…come out as a teacher…”.

    In my experience of teaching for the past 16 years, this is far from a “stable profession”. Maybe it is for those that are tenured, and are guaranteed full-time work at a university. However, that has not been my experience, nor that of many others that I know and respect.

    Unfortunately, it is more cost-effective for universities to hire a small number of full time faculty. The majority (around 85%) of faculty on college campuses are “adjunct”, or part-time. They teach 1-2 classes a semester, and are on a semester by semester, or–more rarely–yearly contracts. They never know year to year, semester to semester, if they have a job there.

    There are no benefits, and it often takes years to qualify for health-care coverage, and more long-term contracts.

    For example, I was teaching as an adjunct at New York University for my 6th year, at Tisch School of the Arts…and still did not have any health-care, and could not get more than a semester by semester contract. This was considered normal. I was a bit depressed to discover that many of my colleagues, who were excellent and had been there longer than I had, were in the same boat. They may have been teaching there for years, and had families (children) to support.

    Meanwhile, a block away, people at Starbuck´s who were fresh out of high school had a better health-care plan that we did, for slinging coffee.

    Many great American artists teach at the university level, whether it be part-time (like Lee Breuer of Mabou Mines, Dan Safer of Witness Relocation, or Aaron Landsman of Elevator Repair Service) or full-time (like Anne Bogart of SITI Company, Andre Serban, or Ron Van Lieu). It´s just another way of diversifying their income, on one level. But I also think that many of these folks really, really enjoy teaching, as do I. We like mentoring people, sharing knowledge, joining minds and spirits in a quest of discovery. We want to have those learning today be better off than we were, when we finished school.

    Sounds like you have a lot of passion for what you do, and what you believe. Maybe one way to get “these ideas into the schools” to “plant healthy ideas about money and art sooner” is for you to teach somewhere, somehow. I bet your passion would inspire others to follow.

  • Lisa – Looks like an interesting site – and school. Can you do me a favor? Can you distill for me what the “entrepreneurial mind” is? I get that I can’t learn how to act from a book — but that doesn’t mean I won’t read Uta Hagen’s Respect for Acting. Are there seriously no well-respected books on what skills being an entrepreneur requires?

  • Thanks, Brendan! Lot to think about here…

  • Brendan McCall

    Thanks, Stage Directions Magazine! Glad that this topic is being picked up!

  • Lisa

    Hi Jacob,
    Sure, there are loads of respected books that can teach you theory and help you reflect what entrepreneurial development requires. Go to EntrepreneurTheArts.com and go into our resource center and you will find many we have identified as being very helpful in this regard.

    But the true development of an entrepreneurial mindset requires action, reflection, redirection and repetition. Understanding characteristics is helpful but irrelevant if you cannot synthesize the knowledge into your daily life. The ability to synthesize, in fact, is a huge problem being recognized in education today. Institutions of higher education are teaching us theory and technique but not how to appropriately apply it. This is certainly true in the arts.

    The agility of an entrepreneurial mind and its ability to take calculated risks and strategically make decisions in a timely manner requires synthesis training which is a kind of mental, emotional strength training. It requires a lot more than just the knowledge of the “exercises” we should know how to do to become stronger.

    One’s level of commitment is in the end always the driving force forward. Becoming an entrepreneur is not for everyone or every artist- no doubt. But without the access to proper training those who vibrantly can be and want to be, will never know they truly can do whatever in life they truly wish to do. And we both know books are great assets; especially in helping you asses how committed you really are to a subject matter.

    The focus of the IAE is to teach you how to apply the skills and knowledge you already have learned, into creating new opportunities for yourself and the community you serve.

    By the way, did you know that Brendan McCall and a number of his students are coming to the IAE this fall for a residency in Chicago?

  • Stkbkr95

    yeah – don’t think you have walked in the shoes of the 501c3 entrepeneur

  • I hear what you are saying, AD, and understand it. Unfortunately, I think many small theatre entrepreneurs today would be hardpressed to find individuals or institutions that are willing to contribute the financial risk to such an unknown quantity as a theater company, in this (American) day and age.

    The economy is hurting, and has done so for some time. There are literally hundreds of theater companies in major cities like New York, Chicago, San Francisco, Seattle, etc. And there are so few private and public granting organizations to support them.

    So, the companies are trying to be clever as possible, trying to wrest the funds that would go to the other 999 companies, and go to theirs. But most of them must rely on personal finance, private contributions (which typically come from friends and family), and a lot of people working for free.

    Many companies don´t last after 5 years. And even if they do, most realize that it is not a money-making scheme. Compare the number of not-for-profit theater organizations in the US (regional theater, off-off-B´way, children´s theater, etc) versus for-profit productions (B´way, Off-B´way).

    Over 10 years ago, back when the economy was doing “well”, an actor living in NYC found it difficult to earn a living with a full contract of an Off-B´way play that ran for 6 weeks in midtown Manhattan. This is a guy with an MFA in Acting from NYU, a roommate up in Inwood, and who spends frugally.

    I think the other side of this conversation on entrepreneurship, as it relates to theater, is that there are systemic problems with the theater industry today, particularly as they affect the talent (actors, directors, playwrights).