I’m not old enough to remember this city, but from what I’ve learned, Times Square in the 1970s and 80s was banal, beaten to the brim, filled with junkies, sex shops and crime.

The artists and intellectuals — avoiding the pitfalls of eroding midtown — took their hobbies elsewhere. A second cohort of the Beat Generation emerged as young, ruminating artists left to find a place in the city to call home.

They chose to move downtown and New York’s formative renaissance began.

Downtown presented an empty canvas: undeveloped economies, bustling streets with virgin sidewalks, alleys waiting for graffiti and clubs soon-to-be filled with punk-rock and hip-hop. The arts flourished because there were no rules.

The downtown terrain was sprawling enough to suit an incoming of new settlers while empty enough to personalize. Some of our greatest art — still recognized today — was produced in downtown New York during its creative boom.

The evolution of New York’s subculture is a natural process, and downtown isn’t what it used to be. The city has been gentrified, cleaned up and settled by families. It lacks the rugged, do-it-yourself culture it was built on. Yesterday’s graffiti artist has been replaced by today’s stroller pusher. The artists left for newer, emerging habitats.

Where is the counterweight to today’s mass, consumer culture?

Is the internet the new downtown?

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I may or may not come back.

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DJ / producer Mark Ronson told a story recently on a music panel that made me consider those questions. Mark was asked about his creative process in developing and producing a pop single: does he deliberately attempt to devise a piece of music that will appeal to large audiences or does he wait for an idea to strike before hitting the studio?

Mark’s story and response brushed on both:

Amy Winehouse, Mark’s collaborator in 2007, had proclaimed to him that “they want to send me back to rehab!” Mark, taken aback, responded, “No, no, no!” Mark had an idea, immediately followed by a studio session and a first stab at the track’s 1960s-style production.

The result was Amy Winehouse’s majorly successful track “Rehab,” produced by Mark Ronson. A casual conversation about Amy’s drinking problem turned into a catchy, soulful piece of music awarded five Grammys including Record of the Year, Song of the Year, and Best Female Pop Vocal Performance.

At the end of the story, Mark explained that his creative process was not sitting down and forcing himself to create a sound that would be popular with the masses. He simply creates music that is appealing to him when the moment strikes. At times this occurs as a result of a conversation or experience; other times it happens while he is in the studio producing other music.

I don’t believe creativity has an off / on switch. Creative, right-brained people are naturally wired to always be “on.” I do believe, however, that certain environments and states of mind are necessary in enabling the creative process.

Mark Ronson may not sit down and tell himself to “create a popular song,” but he was able to use a random slice of conversation with a talented alcoholic as inspiration for a multiple Grammy winning track. The hours of work, brain power and actual creative process took place in the studio, which you can guarantee was controlled, deliberate and practiced, unlike the spark of inspiration.

Take another example involving Steve Jobs: during a trip to India in 1974 he experimented with LSD, later calling the experience “one of the two or three most important things I have done in my life.” A writer has even said that “thinking differently — or learning to Think Different, as a Jobs slogan has it — is a hallmark of the acid experience.” Similar in theme to the story of Ronson’s conversation with Winehouse, Jobs’ experience with LSD was an inspiration for his later work while unrelated to the actual process of creating.

Inspiration for creativity is cheap and can be found anywhere, whether through conversations with an alcoholic, experimentation with LSD in India, or more conventional means. Creative production, on the other hand, is only as valuable as the person’s willingness to sit down and act on it.

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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.

–

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.

–

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.

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If you want to read other essays I’ve written on music, check out:

• Natalie Portman Says This Post Will Change Your Life
• Led Zeppelin Moments: Where Rock Meets Reality
• Exceeding Psychedelia: No One Here Gets Out Alive
• Attention Deficit: The Album
• The Fame Equation

Thanks for visiting.

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I think there was plenty behind it.

Andy Warhol played the people around him as he did everything else in his life: like a large, sprawling canvas. People were his paint, and he was the brush.

Warhol is often remembered for the people he surrounded himself equally to the iconic art he created. His social circle was hand-selected, resulting in a conglomerate of models, artists, addicts, rockstars and freaks, with many categories overlapping. The same way he encouraged audiences to question what art was applied to his social circle as well.

The gang he kept close was known as the Superstars. The currency exchanged was fame, sex and drugs:

The Superstars would help Warhol generate publicity while Warhol offered fame and attention in return. Warhol’s philosophies of art and celebrity met in a way that replicated the film studios at their most powerful. The actors belonged to the studio and were to do as instructed.

What’s interesting about the Warhol Superstars is that they were a group of aggressive individualists you wouldn’t expect to partake in an enclosed social group. Andy was a magnet that kept the group cohesive, at least for short bursts of time.

To that point, here is a plug and a few related bits:

1. Chris Trela is (re)publishing a book on Warhol called The Autobiography and Sex Life of Andy Warhol. In typical Warhol fashion, the book is not his autobiography or about his sex life. It’s a selection of interviews attempting to explain Andy, much like I tried to do above. Its Wiki provides some history of the book.

2. The original author, John Wilcock, one of the founders of the Village Voice, wrote a reflective piece on the book worth reading.

3. Warhol’s Wikipedia entry is also worth reading, especially the section on music. I can’t think of many people who had hands in so many areas of culture while making it appear effortless.

4. Have you seen the Blow Job Movie?

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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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I can attest to have always floated between various social groups, never really identifying with one particular array of hipsters, artists, punks, jocks, nerds, bloods or crips. It sounds oddly high-schoolish of me to categorize my now post-college social habits in that fashion, but I can assure you nothing has really changed in how I observe everyday social interaction. It’s still rich with cliques, gossip, self-consciousness, and of course, habitual indulgences.

Indulgences are worthwhile to evaluate because the exercise provides deeper insight into an individual’s personality, habits and behavior. They often fall somewhere in between two ends of the following spectrum: quick hitters and long haulers.

The quick hitter is dangerously near sighted. He spends his paycheck the day it’s received, proudly pushing bank accounts to zero and credit cards to their maximum. The only future he is concerned with is that night, or maybe the upcoming weekend. The quick hitter is prone to addiction, convincing himself that a short-term high will lead to extended pleasure. He lives for material items, addicted to the rush upon the checkout line when the credit card swipes.

The long hauler saves every dollar he earns, reluctant to spend or act beyond basic necessities. He isn’t saving for anything in particular, besides a distant goal that will never be met. The long hauler lacks spontaneity, with meticulous planning and over-preparation reducing any exposure to serendipity. He doesn’t live for any items besides the uptick in his safety bank account. He denies impulse, mistrusts his own instinct, lacks balls and generally lives a caged, dull existence.

As I write this, I realize the process of indulgence distinction is more than a simple exercise in arm-chair psychology; it’s a tool for how to make relationship decisions:

The advantageous strategy is to commit to relationships that fall somewhere in between the two poles of the indulgence spectrum. As I recall the friendships I’ve lost in the past, and the friendships I’ve made more recently, I attribute indulgence habits as one of the reasons why one started or ended. When two people have similar habits, indulgences become transparent to regular behavior. When they become out of alignment, it tugs on the balance and benefits of the relationship.

Quick hitters are blind to the future, and long haulers are ignorant to the present. Both views are equally destructive in losing focus on the happy, more productive medium. Extreme perspectives are distracting, narrow minded philosophies that accomplish very little besides appealing, at best, to sparing occasions of our own selfish entertainment. Quick hitters and long haulers are best kept at a distance.

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Stress can be debilitating. We’ve all felt it wrap its tentacles around our mind and body, holding us back from executing. I’d argue that the use for stress, fighting or flighting, has become less evolutionary useful in the modern world compared to when our objectives were primarily to hunt or gather. Most of us live and work in front of screens, with little use for the reflex to fight or flight digitally.

Does our urge to fight or flight when we’re stressed by a proposal, overflowing inbox or presentation really help get it done? There’s really nothing inherently stressful, by definition, about any of the things we commonly stress about.

I think, in general, this is the hurdle many of us face with mental health: often what our mind and body is telling us isn’t wrong, it’s just out of context.

The way I overcome stress, specifically in the business environment, is convincing myself it’s completely meaningless at the moment. If the evolutionary directions of stress are to fight someone or flight somewhere, and neither of these actions accommodate my current objectives, I can ignore it. Stress, for the time being, is imaginary.

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At one point in my life, I would have told you Allen Iverson was my role model. While I still respect him for certain accomplishments, a turning point of maturity forced me to realign what a role model was and who was worth having as one.

At the close of adolescence, my role models became within reach. These role models, only an email away, included those doing a more professional, lucrative transformation of what I was doing or wanted to be doing in business.

After a period of time, I realized my role models and I were on the same track, just a few laps ahead. I wondered if I could just run a little faster…

–

What happens when role models become peers?

You could seek new role models. There is something intriguing about constantly admiring someone so out of reach that the opportunity of rubbing shoulders is unlikely. The fairytale distance can be seductive and equally motivational in reaching big, ambitious goals. Within the same argument, others might claim that if a role model can realistically become a peer, you aren’t reaching high enough. Who wants to join the club that will accept them as a member, anyway?

You could remain a disciple to your role model, making him feel comfortably superior. While from an outsider’s perspective it may seem that you’ve reached an intellectual limit, there may be more to gain by appearing less aggressive than him. If you aren’t explicitly running ahead of the role model, his guard is down. The dilemma is that without a power strategy, there is a ceiling. With awareness and manipulation of the superiority complex, you are still controlling the chess board.

Finally, you could ignore the level playing field and approach the situation with your arms swinging. Maybe this is what we’re all fighting for: to box in the same ring as our idols. Fuck making friends, just stiff arm them to the end zone.

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