Structure & Style

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Structure & Style

The Structure

The diary comprised 23 entries that are organized in 4 chapters.

The first chapter (Zero to One) describes Bob’s journey from a struggling entrepreneur to a successful VC.
The second chapter (Chaos Monkeys) highlights his transformation as a ruthless investor who embraces the worst of what Silicon Valley has to offer.
The third chapter (Disrupted) focuses on his change of heart.
The fourth chapter (After On) features a more mature Bob who confronts Silicon Valley’s tech community after having relocated back to his hometown of New York.

The diary entries are separated by interludes that bring more context to Bob’s storyline and to the background story surrounding his environment: MIT, Harvard and the tech community. The interludes are metaphorically called “The Breaks” in honor of Kurtis Blow’s The Breaks which was the first certified gold rap song, and the second certified gold 12 inch single in the history of music. The Breaks went on to define the hip hop genre and helped propel Black culture into mainstream America.

An Afrofuturist Character

Bob is a Renaissance entrepreneur and an Afrofuturist who scaled an AI startup out of MIT and who established himself as one of Silicon Valley’s most successful venture capitalists while keeping his African-American roots alive.

Journalist Jamie Broadnax defines Afrofuturism as “the reimagining of a future filled with arts, science and technology seen through a black lens”. The Afrofuturist hero is highly comfortable manipulating breakthrough technologies while staying deeply grounded in the history of his culture.

As an Afrofuturist VC, Bob is an expert of AI, big data and machine learning, combining raw entrepreneurship skills with next-generation tech and corporate finance expertise. Bob sits at the nexus of two worlds: the technology-infused venture capital industry and the African-American culture.

Bob’s initial relationship with Silicon Valley is complicated: he looks up to its leaders yet loathes its fallacious and superficial nature. However, as he becomes more successful and more popular in Silicon Valley, he starts becoming the very thing he was hating.

Stylistic Approach: Metaphors, Easter Eggs & Wordplay

Bob draws on inspiration from his childhood heroes –contemporary investors and hip-hop artists from the 90’s to develop his own stylistic identity by combining elements of the venture capital industry and of the hip hop culture into a clever wordplay exercise.

The hip hop culture is known for its powerful use of metaphors, symbolism and subliminal messages that carry multiple meanings, and Bob’s diary is no stranger to this rule: Almost every line of the diary is a hidden reference to the tech industry, to a VC or to an urban artist’s famous lyrics.

But the puns only tell half of the story: in Bob’s journal, the names of the VCs, their firms their blogs, and just about anything that is connected to Silicon Valley’s culture (including the sayings, idioms and mottos entrepreneurs live by) carry double, sometimes triple meaning that goes beyond the layers of clever phonetics and rhythm patterns.

Sometimes, the reference is hidden in plain sight. For instance, the 23 diary entries refer to x23, Bob’s AI startup. Other times, one needs to look deeper to spot the subliminal message: both the 23 diary entries and x23 point to the human genome which is encoded as DNA within the 23 chromosome pairs in cell nuclei. The human genome is key to cracking life’s code which is a silent theme hovering over Bob’s diary as he embarks on a journey about self-discovery and the purpose of his life.

It is also worth noting that the first chapter’s five entries represent an ode to the five boroughs of New York—Bob’s hometown. Furthermore, there are exactly 212 Easter eggs that are hidden throughout this chapter in the form of shout-outs to famous tech leaders and to startup idioms. Those 212 Easter eggs point to New York City’s area code.

Another example of symbolism lies in the titles of the book’s five chapters which represent the names of five successful books that deal with Silicon Valley’s culture of entrepreneurship. Zero To One was written by Peter Thiel, co-founder of PayPal and of Palantir Technologies and an early investor in Facebook; Chaos Monkey was penned by former Twitter advisor and Facebook product manager Anthonio García Martínez; Disrupted was authored by Antonio García Martínez, co-producer and co-writer of HBO’s hit show Silicon Valley; and After On is a book by Rob Reid, a venture capitalist who founded Listen.com which created the Rhapsody digital music service.

While these five references are honorific, many others in the book follow the tradition of hip hop artists’ veiled jabs at the competition (rap’s so-called ‘beef’ or ‘subliminal diss’). Throughout the book, Bob indeed uses his signature satirical style to call out many investors and tech leaders.