That’s right, I was just an intern. It feels so funny to say this now, because I always felt above the deprecating title. I suppose this was how they wanted you to feel, even as an intern: delusionally elevated.

Hubris is what makes Wall Street everything it is and isn’t: a mechanism of the functioning world markets while contributing to the dysfunctional perils of political and economic evil. And, the over-achieving, mostly Ivy League interns are all competing for the same end-of-summer “prize”: a high paying banking or trading position to continue the roles of the men (and all two, maybe three women) who came before them.

I beat myself up mentally during the time I was trying to break into Wall Street. So much that I when I look back, my actions do not feel like me and my words do not sound like me. Eventually, a few smart people and pieces of literature snapped me out of it, but the crowded memories still linger.

The following cringe-worthy recollections seemed appropriate, serious and even prideful at the time they occurred during my short stint on Wall Street. Now, they are telling, reflective and even funny.

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1. During an interview, an interviewer told me I was “intense,” and proceeded to recommend that I “relax.” I grinned, thinking honestly to myself “Yes. I fucking nailed this.”

2. I opened an interview proclaiming, before giving the two colleagues interviewing me a chance to speak, that I had just walked around the block listening to Rage Against The Machine’s “Killing In The Name of.” I then gave them permission to “begin the interview.”

3. I attempted to convince a group of high-frequency traders to use Google Reader for their media intake because it was “faster” than the tools they were already using in their terminals. This clearly wasn’t the case, but I thought it was because I was “internet savvy” and, oh yeah, they were writing advanced algorithms to trade 300 shares-per-second.

4. Barely a few months into my nascent Wall Street career, I wrote a how-to piece for college students eager to compete in finance. Upon publication, I immediately emailed the editor begging to take it down because the comments shit on me worse than I had already shit myself.

5. I signed all thank-you emails “Appreciatively” or what should have read “I hope you appreciate me sounding like a douche in the attempt of writing something different than ‘thanks.’”

6. I would openly tell my managers I was a masochist in hopes that they would assign me more work, while ironically complaining to myself all day how uncomfortable my shoes were.

7. I’d strategically place one “fuck” or “shit” in my enthusiastic “why I want to work here” pitch to the senior male managers. If I was pitching a women or minority, I’d always mention the “great diversity” the organization offered.

8. I used to wake up to so early for the train that the last-shift of b-squad prostitutes were still lounging on my street. I would shake my head in disgust, only realizing now that I should have said: ”You and I — maybe-a-lady possibly-a-dude in the five-inch heels and smeared lipstick — our jobs are not that different!”

9. An actual email written back to me once said “try to use ‘please’ and ‘thanks’ in your emails, otherwise they seem a bit arrogant. I don’t care really, but lots of ppl on the street dont like that.” Thanks, asshole.

10. I wrote Michael Lewis a long, self-aggrandizing email and closed with quite possibly the worst question ever. While I won’t reprint my question, Michael’s single-line classic response was “Alex: There’s no good or even useful answer to this question. Best, ML.”

11. This was one of my favorite movie scenes. Okay, it still is.

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I started writing, mostly as therapy, in notebooks during my summers on Wall Street. The reason being wasn’t clear at the time, but it is now: a pen and paper was the only time I could be myself.

As much as I can laugh, mock and narrate my previous, often ridiculous behavior, what bothers me is that it really wasn’t me, not even at the time. It was me being someone else attempting to meet the expectations of a culture where there is no such thing as enough.

Sure, there are plenty of intelligent, rational people that work on Wall Street who enjoy their jobs, make a good living and manage perfectly stable lives outside of work. But for the most part, I found it a difficult culture and career to keep up with where the monetary rewards aren’t in line with the personal job satisfaction, and the only measure of success is a P&L statement.

My jump post-Wall Street to entrepreneurship-land was a selfish decision: I wanted to take the wheel. No bullshit, no acting and no playing dress up. I wanted to be in control, good or bad, of my own fate and monetary outcome.

The concept is popular because its applicability throughout the business food chain is all-encompassing:

Will the starters — the entrepreneurs — be successful with a glorious win or a rough, constructive failure under their belt? Do you hire a previous employee of a failed empire, or do you recruit one that rode the wave to an IPO? Do you invest in the team that has failed marketing a few previous, but promising ideas or that has already built and sold a product?

The answers to these questions might seem obvious, even trite. Of course, you would bet on the previous success! But recent research could sway you to answer differently.

Bob Sutton, in an article in the Harvard Business Review, summarized one particularly compelling study

Shmuel Ellis and his colleagues have really dug into this issue [of learning from failure] with, first, a field experiment with two companies of soldiers in the Israel Defense Forces, who were tested for their performance on navigation exercises. The critical difference between the two groups was that — following standard practice in the Israeli military — the first company had a series of after event reviews during four days of navigation exercises that focused only on the mistakes that soldiers made, and how to correct them. The second company, in its after event discussions, focused on what could be learned from both their successes and failures.

Then, two months later, these same two companies went through two days of navigation exercises. The results showed that, although substantial learning occurred in both groups:

Soldiers who discussed both successes and failures learned at higher rates than soldiers who discussed just failures.

Soldiers in the group that discussed both successes and failures appeared to learn faster because they developed “richer mental models” of their experiences than soldiers who only discussed failures.

One of the more interesting arguments in this realm would be to determine if the startup and founder ecosystem is engineered like evolution: Does Darwinism apply to early-stage companies and their founders? Does success actually breed more success?

I would define the success of a startup, first and foremost, as the construction of a sustainable, profitable business, followed by M&A transactions and liquidity events. Based on the typical longevity of these events, they must favor success by default. But, what about on a shorter¹ time-span? Do only the strong survive, or is the two-time failed entrepreneur more likely to have a third success over the two-time successful entrepreneur? I don’t have the data or the experience to answer this question, but it’s healthy to wonder how and why a previous experience, if any at all, matters.

My opinion is that we shouldn’t see failure as an excuse for not succeeding. That’s where I see the “failure is good!” research conditioning irrational behavior, which can be detrimental to entrepreneurs. Failure has certainly done more good than bad. Consider the Edsel, Newton or the Bob, all seemingly failures with positive, long-lasting outcomes. But, what about the failure of Lehman Brothers, Bear Stearns and AIG? Have these atrocious events provided financial reform or simply conditioned the banks into believing it’s okay to fail at the financial expense of others?

Failure shouldn’t be celebrated or feared. If necessary, it should be reflected on, but never encouraged. Ultimately, the reward of failure is some experience. The reward of success is some experience and, that one thing that really matters, a successful outcome.

Failure is overrated. Failing is a hell of a lot easier than succeeding. The only thing you need to do to fail is nothing. I’m not arguing that anyone supporting failure as a learning mechanism has done nothing, but part of me believes failure is widely encouraged because the majority of the people preaching are trying to feel better for failing themselves.

The “failure is good!” mantra falls into the same trap that many other claims in entrepreneurship-world fall into: they are supported by a culture of echos rather than hard facts and data.

1. I realize this isn’t a perfect analogy to evolution because studying evolution requires analyzing a long time-spans.

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The standard four-year college plan and budding entrepreneurial skill set have always had a complicated relationship. While some entrepreneurs skip or drop out of college to start a venture, other academic institutions have taken the opportunity to teach entrepreneurial coursework. Starting a venture without a college education in entrepreneurship is feasible, as most factors in the startup process are serendipitous.

Students are ignorant to the amount of control they have over coursework. While certain foundational courses are required by the university, in my experience there has been a buffer of flexibility regarding the courses a student takes and how the credits are earned. With the right combination of courses, students can essentially create their own major. Although my major was labeled “finance,” a large batch of credits I received came from starting my business and working the right faculty and departments to document and vouch for my progress. Plus, figuring out loopholes in the university and exploiting them to your advantage is an experience relevant to being an entrepreneur in itself.

Throw an event:

Affiliating yourself with the relevant social circle can be beneficial in learning and practicing entrepreneurship. Organizing an event or conference with a group of entrepreneurs from a specific industry can be helpful in identifying the local community for that industry at your university. As an event organizer, not only will you have a chance to interact with the majority of attendees, but you’ll be viewed as a connector between them.

Work for a startup:

A hurdle small companies face is executing with limited resources, including people, time and money. Most early stage businesses would be thrilled for a competent assistant to help with business development, marketing, or, if you have the skill set, engineering. The issue with hiring interns, even remote interns, is gauging that an investment of time by the company will be less than the amount of time and / or wealth created by the presence of the intern. This is important to reference for your inquiry.

Find the engineers:

Engineers are the guts to the web presence of any company. Websites and business applications often go wrong for two reasons: 1) the initial idea was lousy to begin with, and the most common, 2) the idea wasn’t properly communicated to the engineers. The easiest way to communicate with engineers is to learn their language. Find them, hang out, collaborate and possibly sit in on a class or two to learn programming methodologies. You will meet again.

Take random classes:

Entrepreneurs are versatile individuals eager to learn new ideas and concepts to prepare for future endeavors. Starting any project, either on your own or internal to another company, requires knowledge outside of industry. This includes, for example, legal, writing, public speaking and marketing. College is an ideal setting for learning skill sets outside of your major. It only requires you to attend a class that isn’t yours. If the class is large enough, or if the professor doesn’t mind, it’s wise to take advantage of.

Teach a course:

Information acquisition, with the intent to know more than your competitors, is a skill set of an entrepreneur. Teaching a course, specifically a subject matter related to your industry of choice, can be a practice round for educating your future organization and stakeholders. It not only requires you to become a semi-expert on a specific topic, but it forces you to disperse information to a collection of peers who will be graded on their understanding. This is most easily done as a teaching assistant, but could also be organized independently if you can find a group of peers who are diligent to show up to your class every week.

Infiltrate the MBA program:

Most schools with MBA programs, and even some select undergraduate programs, offer an early stage venture capital course. In my experience, these courses simulate a portion of the fundraising due diligence process between entrepreneurs and investors. The startups trade their time for the opportunity be researched by the students with the assistance of a professor with a background in venture capital. In my specific case, I was able to compete with other startups in the course for a potential seed round of funding at the end.

Leverage your professors:

The professors worth taking, if you have the luxury of choosing, are the ones who are veterans of industry. Meaning, professors who have at one point in their career taken the painful path of entrepreneurship and can provide mentorship while you are at the university or enrolled in their course. I’d recommend seeking them and using them as a resource in and outside of the classroom. They’ll be willing to provide support, because at one point, someone did the same for them.

Write for your newspaper:

Part of the entrepreneurial process can involve becoming a thought leader locally. Most college newspapers have a small business section that covers local businesses. College newspapers are enthusiastic to publish stories about their students, and most students like reading about their peers. Contributing to your college paper’s business column is a great incentive to learn about local entrepreneurs while contributing to the university community.

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Entrepreneurship isn’t a choice. It’s a set of skills every student of life needs to be equipped with. And, these skills will only improve with maturity, practice and discipline. The activities I described above can act as entrepreneurial entry points for a career, but don’t necessarily transform you into an entrepreneur. Remember: there is no blueprint. All things considered, there’s no better way to learn entrepreneurship than to start a company. If you don’t need the practice, why not start as a student?

Entrepreneurs are the backbone of industry. They are the risk takers willing to bet their “jobs” on what they believe in. Entrepreneurs leverage limited resources to solve big problems. With the current state of unemployment, there aren’t jobs waiting for students upon graduation. Students may have to create their own jobs, simply because they have no other choice.

Entrepreneurs don’t just talk about starting things; they take action. The beauty of acquiring an entrepreneurial skill set is that it’s beneficial regardless of your field and interest. The above suggestions are meant to be interpretative while displaying the practicality of starting anything. You don’t have to be running a startup to be an entrepreneur; you just need to leading something.

I suspected that Entrepreneur’s Disease might be not just a correlated affliction, but a condition springing out of the very nature of the entrepreneur itself. I’ve heard over and over again that “startups will consume your life. No, really, they’ll totally consume your life, and you can’t even envision the extent of the utter completeness with which every non-startup aspect of your existence will be decimated and the earth beneath it salted.” Sounds like the victims of Entrepreneur’s Disease have not just heard that but embraced it, internalized it and loved it.

As unappealing as the life of someone in the heady midst of Entrepreneur’s Disease might superficially sound to me — and probably sounds to many readers — I must admit my unquashable attractions to (a) bold, audacious moves, (b) complete self-determination, whether it leads to success or failure, (c) endeavors the odds are against and (d) the amassing of fuck-you money. Especially (d). So I probably front like I understand entrepreneurship less than I actually do.

Colin has become one of my favorite voices on the internet and is an emerging star through his four quadrants: broadcasting / interviewing, writing / essayism, film / video and sound / music. Subscribe to his blog and listen to his interviews if you don’t already do so. Here are a handful of my favorite pieces and respective quotes:

What It Is

“I’ve realized that charting one’s own course in terms of other, previously-charted courses hurts as much as it helps. As much as claiming that you’re working toward becoming like Joe Icon satisfies others’ questions about your slightly unconventional aspirations, it’s no recipe for originality.”

Thoughtspace

“I’d submit that this all comes down to clarity, the condition that keeps the junk outside the brain’s purview and the meaningful stuff inside. Clarity demands the absence of sonic, visual, informational or personal noise.”

Less

“I also prefer a multiplicity of small, minimally-designed spaces, both aesthetically and intellectually. I fear not that my next place will have too little room, but too much; I worry not that I will have too few possessions to my name, but too many. My dream is to have several available dwellings, absolutely no larger than I require, in select locations across the globe.”

Cargo Cult Creation

“To reiterate what’s been written before: don’t think what they thought, think how they thought. Don’t do what it does, do it how it does it. Don’t think of what it’s about; think of how it’s about it.”

Buffering, Please Wait

“I call this “the buffer.” In this specific case I mean the financial bulwark between you and the dole line, but the importance of the buffer in all resources cannot be denied. Amassing a sizable amount of cash on hand for the proverbial rainy day, coloquially referred to as “fuck-you money” (FYM) — not an expression original to me, though I do use it all the time — is a goal toward which I work.”

I also like his interviews with Philalawyer, Merlin Mann, Ben Casnocha and Andy Mckenzie.

An entrepreneurial career certainly has its perks. You control your own schedule, activity and work inputs, and have the ability to quickly assess a situation to move towards maximizing an output at any given time. With the few layers of organization that exist in an entrepreneurial business, a strategy can quickly become a tactic. The fragile speed is exhilarating, and often blindly addicting.

If you assess a high level executive at a large company, the perks they fight for through the stuffy ranks include those an entrepreneur can amass to almost instantly. The freedom, the attitude, and even the swag that comes along with being the decision maker. Pay schedules typically differ in timing¹ , but the passive independence can be similar.

Corporations can be binding, while the titles are homogeneous depending strictly on age, experience and income. Small organizations, startups and entrepreneurial ventures are free willing, where titles matter the least, but are thrown around the most. I see it all the time, and the autonomous entitlement can be destructive.

It’s easier to claim you’re an entrepreneur than to actually work your way up a corporate rank. Entrepreneurs make bold claims about their market and product, skills and ability, experience and contacts, sometimes before merit exists. Fighting your way up the corporate ladder proves something in a bureaucracy. Crowning yourself with a title is meaningless in a meritocracy like a startup.

It’s not strategy. It’s being self-aware enough to realize what you do, not what you’re labeled, is the only thing that matters.

It’s lonely at the top, and when the best showman can become the champ, it might seem useful to proclaim you’re something that you aren’t. Appearance is deceiving, and talk is cheap. Words are easy to throw around, but even easier to see through when there’s no where to hide.

Entrepreneurship can be a narcissist’s playground. The bigger you come, the quicker you’ll rise, and eventually, the harder you’ll fall.

1. The executive pay is typically linear, while the entrepreneur will ideally hit an eventual home run

Good morning Los Angeles.  In the land of the lotus eaters, time plays tricks on you.  One minute you’re dreaming, the next your dream has become your reality.  It was the best of times, if only someone had told me.

- Hank Moody

There is a shift in perspective–a heavy metal fork in the road–where we choose a path of purpose for our creative content.

The choice typically floats in a thin range between content that pleases just the creator versus content that merely pleases the admirer. Most content creators (artists, musicians, writers, marketers) go through the shift at some point, particularly if they choose their hobby as a business. It’s a cautious zone where instead of putting one foot in front of the other at our own pace, we side-step carefully to satisfy the largest majority of our fan or customer base. To monetize, we must embrace any paying fandom as a gift, and react to it accordingly.

Clement Greenberg, a well-known art critic, once described the freight train of art history as taking the rigid path of “self-criticism,” followed by “self-definition,” concluding with “self-definition with vengeance.” And, I think the path to creative, monetary independence is similar. The “self-criticism” is the initial fear of selling out. The “self-definition” is tackling the reasoning behind our creative purpose.¹ The final “self-definition with vengeance” is a combination of both, where we try to anticipate not only the audience’s expectations, but our own expectations, in terms of demand.

An artist will probably tell you their greatest payoff, whether hobby or business, is the value of looking back on the ritualistic process–the so called “struggling journey.” Freud disagrees, who said the greatest payoff for an artist is simply fame, money and beautiful lovers.² Hell, even Warhol was honest. He admitted he would endorse anything for enough money, even putting an advertisement in the Village Voice with his personal phone number.

Regardless, it’s a sort of “be careful what you wish for” mentality. We all want to do what we love for a living, until the lotus eaters decide they want us to do what they love. Sometimes, as much as you may want to, there’s no turning back once you choose a path to take. Do you work for yourself, or do you work for your customers? Do you produce content for yourself, or do you produce content for your fans? If you don’t care, or it’s all the same to you, then you’re lucky.

The ultimate, ideal goal, I suppose, is to travel the road where what we want to create is identical with what we can monetize. No overarching demands besides our own. Just business as usual, where the only real conflict of interest is if it’s self-inflicted.

There’s no right or wrong path; this is simply my self-methodology for making sense of it and how to tackle the various forks in the road. It really breaks down into categorizing personal goals, and deciding specifically how to get there.  Just like business, art shouldn’t create a mirror for the viewer, but allow viewers to see it for what it is. And, the “what” should be up to us.

1. This is the decision of keeping something as a hobby, or doing it for money.
2. Quoted from Tom Wolfe’s The Painted Word

This was my first real job, two years ago, where my morning routine consisted of me waking up early enough that the night’s last round of street hookers were still on their final shift of walkabouts on my lower Manhattan block scavenging for desperate business. No, I wasn’t a pimp. I worked on Wall Street.

The most fascinating aspect of my job and working in New York had less to do with my actual workday, and more to do with the professional culture I was thrown into at a young age. The ride to the subway consisted of me in a dark suit and loosened tie, headphones blaring, with occasional beads of sweat dripping down my face if the subway car wasn’t air conditioned, usually observing the other traveling patrons.

I’d try to identify the people around me, usually scribbling notes to myself: The foreign construction worker in baggy jeans and a stained white t-shirt, who probably spoke little English, but is so happy to have a job in New York. The chef with calloused hands, nodding off to sleep, probably writing his specials menu for the day behind his eyelids. And, the handful of other costumed workers, anticipating the relentless day of established routine in front of them.

“Same hustle,” I’d think to myself.  “Just a different grind.”

Corporate America creates artificial levels of bureaucracy. What seems to be decided by a market, is really only decided by what feels like an irrational, societal force. And, it wraps around to an inherent issue of the recent economic crisis: petty value attributed to worthless junk, with price being determined by how much you could convince a fool to pay for it.

My job, although it felt important, was nothing more than a title. No more or less important than the others riding in the subway with me every morning.

The appeal of working on Wall Street, especially for those in college (like I was), or recently graduated, is created by accounts of ridiculous parties filled with glamor and excess, in addition to the Hollywood caricature of money-fueled machoism. It wasn’t that I didn’t like the work; it was more that I had difficulty identifying with the culture dragged along with it. And, it’s too easy for any of us get lost in routine.

A lot of my job consisted of waiting for the sun to come up, and then go back down. If I learned one thing, it’s that I didn’t want to have to do that anymore. Waiting on something can be painful, especially when it becomes part of your work day. I absorbed valuable experience, in concepts and insight into how the system works. The trick, I suppose, is to monetize it while not stepping into the unnecessary bullshit.

Now, I’m working on my start-up, and a handful of other creative projects, mostly out of New York and Philadelphia. The waiting has ended, especially for the sun to go up or down. And looking backwards, my interests haven’t changed much. Only my motives and priorities.

At first flash of Eden, we race down to the sea.
Standing there on Freedom’s Shore.
Can you feel it now that spring has come?
And it’s time to live in the scattered sun.

- The Doors, Waiting for the Sun