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Monkey Business

Monkey Business

Swinging Through the Wall Street Jungle
by John Rolfe 2000 288 pages
3.97
5k+ ratings
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Key Takeaways

1. Investment Banking: A Grueling Rite of Passage

This story is about the dues that all junior investment bankers have to pay.

Paying the dues. Junior investment banking is characterized by extreme demands and a painful rite of passage. Associates must endure long hours, constant pressure, and often demeaning tasks to potentially reach the coveted senior levels. The authors describe this journey as crossing a vast, hot desert towards a potentially illusory oasis.

Survival strategies. To survive the "gauntlet," young bankers either fully embrace the culture or maintain a sense of humor while keeping one foot grounded in reality. However, even with humor, the intense pressure and demands can lead to significant personal strain and a loss of mental equilibrium, leaving them "blistered" despite the potential rewards.

Costs vs. benefits. While the compensation and perks are high (private jets, best hotels, doubling salary), the authors ultimately found the required unwavering devotion and the nature of the work (often mindless paper processing) to be "way out of whack." They left banking for roles they enjoyed more, realizing the high pay compensated for a job that fundamentally "sucked."

2. Recruiting: The Deceptive Mating Dance

Hello, sucker!

The machine's objective. The Wall Street Investment Banking Machine is a relentless recruiting force targeting top students from prestigious universities and business schools. Its sole purpose is to fill the pipeline with analysts and associates, who serve as the "serfs and indentured servants" of the industry, providing the bodies needed to throw at potential business.

The allure of money. Business schools become fertile ground for this recruitment, with placement surveys highlighting exorbitant starting salaries in consulting and investment banking. Students, often driven by the desire for financial advancement, engage in a "two-year mating dance" with recruiters, sometimes sacrificing camaraderie and noble ideals for a shot at the high-paying jobs.

Shameless self-promotion. The recruitment process involves highly scripted presentations, cocktail parties, and interviews where candidates are expected to demonstrate eagerness, knowledge (even if faked), and a willingness to conform. Recruiters, despite their polished facade, often see through the pretense but play the game, dangling the promise of prestige and wealth to secure commitments, sometimes even resorting to "exploding" offers or leveraging personal connections.

3. The Hierarchical Food Chain

The higher a monkey climbs, the more you see of his ass.

A strict pyramid. Investment banking operates on a rigid hierarchical structure, resembling a pyramid where each level rests on the one below. The further down you go, the more primitive the "species" of banker, with senior managing directors at the top and analysts at the bottom.

Roles and misery levels:

  • Managing Directors: Source business, paid the "big bucks."
  • Senior Vice Presidents: Process deals, close to the "brass ring," often smell "gamey."
  • Vice Presidents: Processing robots, trapped by high salaries but miserable due to lack of life outside work, like "caged animals."
  • Associates: Lives "suck," take aggression from VPs, barely human, communicate by "grunting."
  • Analysts: "Monkeys," at the bottom of the "shit heap," mentally, emotionally, and physically abused for 2-3 years.

Passing down the pain. The hierarchy ensures that misery is off-loaded downwards. Managing directors give orders, senior VPs perpetuate panic, VPs shove a "hot poker" up the associate's ass, and associates, in turn, make the analysts' lives miserable. This system creates a perverse dynamic where those higher up have "institutional authority to kick my ass."

4. The Mindless Processing Work

Being assigned to create a pitch book is a punishment.

Beyond advice and capital. While bankers theoretically provide financial advice and raise capital, a significant portion of junior bankers' time is spent on "mindless processing," particularly creating pitch books. These documents, designed to win new business, are often unoriginal, plagiarized, and filled with hyperbole and aggressive valuations.

The pitch book anatomy:

  • Overview: Shamelessly strokes the client's ego.
  • Capital Markets Update/Strategic Considerations: Justifies the deal or explains market conditions (often with jargon).
  • Valuation: The "heart" of the book, often reverse-engineered to meet a target value ("doggy-style valuation").
  • Expertise: Spins "league tables" (rankings) to make the bank look like the top player, often through creative data manipulation and footnotes.

A painful creation. Creating pitch books is described as an "unholy creation," akin to illuminating a holy manuscript but resulting in "three-week-old potted meat and smelly cottage cheese." The process involves endless revisions, often dictated late at night by senior bankers, turning associates into "master fax operator and word processor[s]."

5. The Critical Role of Support Staff

To get on their bad side was to commit hari-kari.

The unsung heroes. While bankers focus on deals and pitches, the support staff, particularly the word processing department and the copy center, are critical to getting anything done. Associates quickly learn that their success depends on these individuals, who hold significant power despite their lower position in the hierarchy.

Word processing woes. The word processing department, staffed by "struggling actors and actresses and the Christopher Street fairies," is essential but temperamental. Associates spend 40-50% of their time on word processing tasks, navigating errors and rewrites. Getting on their good side requires being "nice" and showing "respect," as they cannot be bought with money.

The copy center bottleneck. The copy center, run by "patriotic Puerto Ricans," is where major bottlenecks occur. Unlike word processing, associates cannot do the job themselves, making them dependent on the copy center staff. Rudeness is met with deliberate delays, forcing bankers to rely on subtle bribery and relationship-building ("lap dances down at Shenanigans") to get priority service for their urgent, last-minute jobs.

6. The Illusion of Glamorous Travel

Traveling is a bitch.

Dream vs. reality. Junior bankers are promised glamorous travel opportunities, jet-setting to exotic locations to close deals. The reality is far less appealing, involving constant, stressful trips, often one-day excursions or red-eyes in coach class, carrying heavy bags and battling airport hassles.

The road show grind. Road shows, designed to sell deals to investors, are particularly grueling. They involve visiting multiple cities and countries in rapid succession, often with minimal sleep. The travel is tightly scheduled, leaving no time for sightseeing or relaxation, turning cultural landmarks into fleeting glimpses from a limousine window.

Diligence marathon. Due diligence trips, meant to verify a company's operations, can be equally taxing, involving long flights, time zone changes, and often sitting in conference rooms listening to presentations that could have been done remotely. The authors recount a particularly brutal week-long trip across Europe and Mexico, highlighting the physical toll and the inability to escape work demands, even across continents.

7. Drafting: The Painful Process

No passion in the world is equal to the passion to alter someone else’s draft.

The prospectus creation. A major task for bankers is creating the prospectus, a legally required document for securities offerings that also serves as a sales brochure. This involves "drafting sessions" with a large cast of characters including bankers, lawyers (underwriters' and company counsel), and accountants.

A crowded, contentious room. Drafting sessions are characterized by large groups (20-30 people) spending long days arguing over language, often driven by conflicting goals (bankers want sales, lawyers want liability protection). Associates' roles range from passive presence to managing the process when seniors step out, often feeling like they are playing "two-on-two basketball with twenty-five people on each team."

The document's sections. The prospectus includes sections like the Prospectus Summary (full of "bullshit"), Risk Factors (a lawyer's "wet dream" overloaded with irrelevant detail), Use of Proceeds, Financial Data (spun to look good), MD&A (management justifying mistakes), Business (more detail than the summary), Management (balderdash biographies), Stockholders, Underwriting, and Financial Statements (the "real meat and potatoes" with least creative input). The process is slow, painful, and often feels like a waste of time.

8. The Bottleneck: The Copy Center

The copy center is where the bottlenecks always pop up in the pitch book–making process.

The key to production. While word processing prepares documents, the copy center is where they become tangible pitch books and prospectuses. Despite being outsourced and staffed by lower-paid individuals, the copy center holds immense power because bankers are dependent on their ability to produce high-quality, complex documents under tight deadlines.

Power dynamics. Bankers often treat copy center staff poorly, but this backfires when urgent jobs are needed. The copy center becomes a "kangaroo court for assholes," where staff can delay jobs as retribution. Associates learn to build relationships and offer subtle bribes (pizza, beer, cash, or even "lap dances") to get their jobs prioritized over others.

A barbaric process. Despite industrial equipment, assembling pitch books is often manual and prone to errors, especially with numerous color pages. Associates must proofread every copy by hand, fixing mistakes themselves or cajoling the copy center staff to do it, often under extreme time pressure before a pitch or flight. This highlights the disconnect between the high-stakes banking world and the manual labor required to support it.

9. Compensation as a Golden Handcuff

We needed the bragging rights.

The bonus obsession. Compensation, particularly the annual bonus announced in February, becomes an all-consuming focus for junior bankers. The six weeks leading up to the announcement are filled with rampant rumors and calls to peers at other banks to gauge expected payouts, turning associates into "horse traders" assessing their worth.

The illusion of being the best. DLJ strategically tells each associate they are "at the top of your class" and strictly forbids discussing compensation. This tactic prevents associates from realizing they likely received similar amounts and maintains control. The desire to believe they are the best, fueled by arrogance, makes them susceptible to this manipulation, preventing collective action or dissatisfaction.

Fleeting joy. The high bonus numbers (e.g., $209,000 total comp for a second-year associate) provide only momentary satisfaction. The joy is quickly overshadowed by the immediate return to the grueling work, highlighting how the money serves as a "corporate narcotic" and a "golden handcuff," compensating for a miserable existence and making it difficult to leave.

10. The Personal Toll and Loss of Self

There was no longer any life outside the office.

Relationships crumble. The demanding hours and constant work pressure take a severe toll on personal lives. Many associates' relationships and engagements end because their partners cannot tolerate the lack of time and presence, leaving bankers increasingly isolated.

Degradation and perversion. The intense, all-consuming nature of the job can lead to a deterioration of personal boundaries and behavior. The authors describe instances of public drunkenness, vulgarity, and even self-gratification at the office, illustrating how the job can warp individuals and lead to a loss of self-respect and connection to the outside world.

The epiphany. For the authors, the realization of the job's destructive impact comes gradually or through sudden epiphanies. Seeing older, unmarried, seemingly perverted bankers who had made banking their entire life serves as a cautionary tale. The realization that their own lives were becoming pathetic, with no existence outside the office walls, becomes the catalyst for seeking escape and redemption from the "dark underbelly" of investment banking.

Last updated:

Review Summary

3.97 out of 5
Average of 5k+ ratings from Goodreads and Amazon.

Monkey Business receives mixed reviews, with an average rating of 3.97 out of 5. Readers find it an entertaining and candid look into investment banking, appreciating its honesty and humor. Many relate to the grueling work hours and personal sacrifices described. The book is praised for its insights into the industry's culture and practices, though some note it may be outdated. Critics argue it tries too hard to be scandalous and lacks depth in certain areas. Overall, it's recommended for those curious about investment banking or seeking a humorous finance memoir.

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About the Author

John Rolfe is a co-author of Monkey Business, drawing from his experiences in investment banking. He graduated from Virginia Tech, the University of Florida, and Wharton Business School, where he was editor of the Wharton Vulgarian. After working at DLJ, Rolfe spent time at a private investment fund before co-founding an equity-oriented money management firm in 2001. He currently manages the firm from Vermont, where he lives with his wife and two children. Rolfe's diverse educational background and career trajectory in finance provide a solid foundation for his insights in the book.

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