Disrupted cover

Disrupted - Book Summary

My Misadventure in the Start-Up Bubble

Duration: 24:51
Release Date: October 29, 2023
Book Author: Dan Lyons
Category: Entrepreneurship
Duration: 24:51
Release Date: October 29, 2023
Book Author: Dan Lyons
Category: Entrepreneurship

In this episode of 20 Minute Books, we delve into "Disrupted", a captivating exploration of the world of tech start-ups, written by experienced journalist, novelist, and screenwriter, Dan Lyons. After a remarkable 25-year tenure in technology journalism, Lyons found himself experiencing a drastic career shift. Fired from his editorial position at Newsweek, he decided to test the waters of Boston's vibrant tech start-up scene, landing a job at HubSpot, a bustling software company.

As we journey through "Disrupted", you'll follow Lyons' humorous and somewhat rocky voyage into this new realm, filled with unusual practices such as candy walls and other amusing quirks that depict the peculiar culture he calls 'HubSpottiness'. The narrative strips back the glitz and glamour of start-up life, providing an authentic, behind-the-scenes glimpse into the inner workings of a modern tech enterprise.

This insightful book is a must-listen for those who are keen on understanding the operations of technology start-ups, for potential investors in any start-up, or people who are part of a small business or start-up environment. Immerse yourself in this episode as we unfold the truth behind the start-up world, guided by the wittily raw narrative of Dan Lyons - a writer recognized not only for his extensive journalism career but also for his successful blog, 'The Secret Diary of Steve Jobs', and his contributions to the renowned HBO series, 'Silicon Valley'. Enjoy the journey, dear listeners.

Embark on a rollercoaster ride through the glamorous yet deceptive world of tech startups.

Welcome to Silicon Valley! It's the promised land of the tech world, birthplace of industry titans like Google, Apple, and Facebook, and fertile ground for constant innovation and new ideas sprouting all over. But have you ever stopped to wonder, what's behind this shimmering facade?

In this narrative, we'll unravel the journey of Dan Lyons, who, left jobless in his mid-50s, dived headlong into the whirlwind world of startups at HubSpot — a firm renowned for its focus on inbound marketing and sales. The bumpy ride that followed, fraught with bizarre business antics and questionable working conditions, revealed the startling reality hidden behind the glossy tech hype.

As we dive deeper, you'll find out:

- The peculiar qualities needed to fit into the HubSpot mold,

- The strange but true fact that some people find conversations with a plush toy innovative, and

- The curious meaning of the term "bozo explosion".

The career rebirth of a traditional journalist in the turbulent modern media landscape.

Our tale commences in 2012 with Dan Lyons — a seasoned journalist and technology editor at Newsweek — finding himself jobless in his 50s and facing a drastically different employment landscape. He wasn't alone in this boat. The disruptive force of the internet technology explosion in the 2000s left many veteran professionals questioning their place in the media industry.

The advent of the 21st century saw tech behemoths like Google, Facebook, Zynga, and Groupon soaring to stratospheric heights. Meanwhile, traditional media players — the venerable newspaper and magazine industries — were floundering, caught in a desperate struggle for survival and adaptation.

These ascendant tech companies offered ground-breaking products and services that transformed fundamental human activities — from shopping and socializing to the way we consume news and information.

The power dynamic had shifted. Readers no longer turned to newspapers and magazines for their information fix; everything they desired was but a click away. As a result, print powerhouses like Newsweek were plummeting from grace. Advertising dollars flocked to online platforms, and magazine subscriptions were mercilessly slashed.

This stormy climate led to Lyons's sudden layoff. The bitter irony? This happened right after Newsweek published "The Beached White Male" — an article reflecting on a generation of experienced professionals abruptly left high and dry by ruthless company downsizing.

To secure employment, Lyons had to reinvent himself, propelling him into the bustling universe of startups. The stakes were high — he was a husband, father of two, and the sole breadwinner, making a stable job and robust health insurance non-negotiable.

His journey took him to San Francisco, where he joined a tech-news website named ReadWrite. It was a decent gig, but far from ideal, given that his family was tethered to the East Coast in Boston. But it did offer him a front-row seat to the buzzing start-up scene in Silicon Valley. And a thought emerged — could he transform his career as a writer in the marketing division of a startup?

The intriguing and often puzzling initiation into the startup sphere for a seasoned journalist.

In his time as a tech journalist for Newsweek, Lyons had grown quite familiar with internet titans like Twitter and Facebook. He'd interviewed many of their top brass and was acutely aware of the immense financial windfall that awaited those who got in on the ground floor of such ventures.

However, despite his seasoned understanding of their operations, nothing could have prepared Lyons for the curious business conduct within startups.

His first brush with this unfamiliar universe arrived when he scored an interview at HubSpot, a software startup nestled in Cambridge, Massachusetts. He'd applied in response to a LinkedIn job post, and though the interview was fairly successful, he found himself puzzled when offered the nebulous role of a "marketing fellow". This didn't exactly sound like a job title.

This ambiguous approach echoed in his conversations with Shah and Halligan — the founders of HubSpot. While they chatted at length, they never really clarified what Lyons's precise role within the company would be.

From their discussion, Lyons gathered that they fancied the idea of bringing aboard a journalist who could help establish HubSpot as a "thought leader" in the marketing realm. However, they never conveyed a clear vision of how exactly he would achieve this feat.

The conversation veered closest to a specific directive when Halligan suggested "missions" for Lyons — a convoluted way of hinting at the enhancement of their blog to boost brand visibility.

These initial encounters at HubSpot left Lyons somewhat disoriented. Nevertheless, he resolved to embrace this novel environment and adapt to new work practices.

There was an undeniable excitement coursing through him about the potential of this startup experience, stirring a readiness to learn about the world of marketing — a field he'd never previously ventured into.

While the salary offered was on the lean side, HubSpot compensated him with stock options — a potentially lucrative reward if the company succeeded.

HubSpot's peculiar cultural codes, offbeat jargon, and unconventional practices — an introduction to startup eccentricity.

April 2013 saw Lyons officially joining the HubSpot team, and right off the bat, he was launched into the company's peculiar rituals, cryptic lexicon, and near-obsessive missions.

He soon discovered that HubSpot wasn't solely fixated on profits; it was on a more profound "mission". The startup aimed to revolutionize the world through their novel marketing software. Moreover, HubSpot's co-founder, Dharmesh Shah, seemed to occupy an almost mystical place in the company, with some employees and clients referring to him as a "spiritual leader".

In his initial days, Lyons received a 128-slide PowerPoint manifesto aptly named "The Hubspot Culture Code: Creating a Company We Love". This document pitched HubSpot as a quasi-utopian enterprise where teamwork trumped individual ambition, and notions of work-life balance were irrelevant, as work was life.

While this was admittedly odd, it wasn't completely foreign to Lyons. Silicon Valley was notorious for inducing a certain devotion in its employees — those working in juggernauts like Google and Apple were infamous for "drinking the Kool-Aid", transforming from regular staff into fervent believers of company values and "world-changing" missions.

At HubSpot, the staff was urged to adopt a unique dialect and dress code as part of their quest for uniform happiness. Therefore, a true "HubSpotty" individual would "make magic" by adhering to the principles of HEART — embodying humility, effectiveness, adaptability, remarkability, and transparency.

The most devout HubSpotters would often sport the color orange and dutifully participate in "fearless Fridays" — a monthly ritual encouraging employees to confront a non-work related fear.

The argot at HubSpot was so puzzling that a company Wiki page had to be created to guide newcomers in decoding it.

Within the corporate walls, conversations would be peppered with terms like SFTC, SLA, or KPI instead of straightforward language like solving for the customer, service-level agreements, or key performance indicator. When someone was in GSD mode, they were ready to "get shit done". Those not in GSD mode might be on the verge of "graduation" — a euphemism for leaving HubSpot, regardless of the circumstances.

The unique workplace culture at HubSpot: A perplexing experience for seasoned employee Lyons.

Though unusual, the customs at HubSpot were intended to encourage team cohesion. However, Lyons, being older, often felt like an outcast amidst this youthful corporate culture.

Lyons was unfamiliar with the open-concept workspace at HubSpot, which stripped employees of any semblance of privacy. Observing the long tables filled with employees, he couldn't help but equate it to the cramped working conditions of Bangladeshi sweatshops — only here, people were huddled over laptops rather than sewing machines.

Another peculiar aspect of HubSpot was the imposed "fun" within the workspace, a phenomenon Lyons hadn't previously encountered. The workplace boasted multiple zones resembling play areas rather than traditional office spaces.

These included a "nap room" complete with a hammock, a section with unused musical instruments intended for impromptu jam sessions, and a conference room that moonlighted as a recreational area equipped with ping-pong, foosball, and pool tables, as well as video games.

HubSpot's prized "candy wall" was another oddity that left Lyons bemused. An entire wall in the cafeteria was dedicated to glass cases filled with an assortment of candy bars and junk food.

Perhaps the most eccentric practice, however, was the instruction for employees to converse with a teddy bear. Lyons was utterly confused when his manager proudly announced this alleged breakthrough in management technique. The grand idea involved bringing a teddy bear named Molly into meetings to symbolize the customer they were striving to satisfy.

For Lyons, a veteran employee who previously reported to Pulitzer Prize-winning author Jon Meacham, this shift to a boss who considered dialogues with a stuffed toy innovative was indeed a sobering experience.

Lyons's recommendations for change spark friction and challenge at HubSpot.

Three months into his tenure at HubSpot, Lyons found himself grappling with the ambiguity surrounding his role as a marketing fellow. When he made attempts to introduce fresh concepts, he was met with a distinct lack of enthusiasm from the company.

Lyons had assumed his role would involve bolstering HubSpot's company blog. Therefore, he curated content that targeted venture capitalists, CEOs, and prospective investors. However, he soon found out that his intended audience wasn't this sophisticated crowd, but fictional avatars named "Mary the Marketer," "Enterprise Erin," and "Ollie the Owner."

These personas represented small business owners seeking practical marketing advice like "15 Free Stock Photos You Can Use" or "How to Create a Facebook Brand Page." HubSpot's goal was to entice these readers to click on links that led them to online forms, through which they could capture their personal details.

The request to simplify his blog content came as a significant blow to Lyons. Undeterred, he suggested a novel idea — the creation of a separate blog, named Inbound, geared towards high-end content. However, when he presented this idea to middle management, it was promptly dismissed.

Unfazed, Lyons took the proposal directly to the company founders, who enthusiastically endorsed it. But approval from the top brass at HubSpot didn't guarantee implementation. The middle management managed to thwart the idea, maintaining its rejection.

Lyons, however, didn't back down without a fight. The ensuing negotiations resulted in a compromise: Lyons was granted permission to manage a mini "sub-blog" where he could publish more complex articles.

The catch? Lyons would be assigned to the loudest corner of the company — the telemarketing room, aptly nicknamed "the spider-monkey room" by employees, due to its noise and chaos.

The pitfalls of rapid expansion: How start-ups can inadvertently foster mediocrity and adverse working conditions.

Lyons soon found himself confronting the stark reality that HubSpot lacked efficient management. His relocation to the bustling telemarketing room shed light on the harsh realities of working conditions.

He identified a prevalent pattern at start-ups, aptly termed "the bozo explosion." Coined by Steve Jobs, this term refers to the practice where early employees at a start-up, despite their lack of prowess, ascend in ranks purely due to seniority.

These subpar leaders are then bestowed with the authority to recruit, often favoring mediocre candidates to whom they can feel superior. This cycle perpetuates substandard management, as evidenced at HubSpot.

When such mediocrity is celebrated, it can lead to despairing scenarios. For instance, Lyons was once tasked to partake in an overnight "hackathon" aiming to churn out intentionally average blog content.

Inadequate management aside, Lyons's experience in the telemarketing room unveiled another grim reality. Dubbed "spider monkeys," this space was filled with fresh college graduates, crammed into a room, relentlessly cold-calling potential customers. Failure to meet their sales targets could cost them their jobs. To make the high-pressure environment somewhat bearable, an endless flow of free beer was provided.

Contrarily, these telemarketers played a crucial role for HubSpot during this period. The company was on the brink of launching its initial public offering (IPO), primed to issue its debut stock shares.

In this phase, HubSpot was in a frenzied rush to bolster its growth as swiftly as possible. Prospective buyers seldom consider a company's profit margin; they're more interested in its rate of growth. Consequently, HubSpot was caught up in a race against time, striving for expansion and overlooking the mediocre environment that could affect their long-term success.

HubSpot's unique strategy: Employees overlook lack of benefits and job security due to a sense of specialness.

Lyons discovered that the "spider monkeys" weren't the sole casualties of HubSpot's work culture. He was struck by the sheer number of individuals tolerating this demanding environment.

Ever since Google set new precedents for employee treatment in the tech industry, companies like HubSpot have followed suit, forsaking job security and treating their personnel as transient. This results in the absence of long-term contracts, pension schemes or employee unions, underlining an evident lack of employee loyalty.

This ideology also seeped into HubSpot's benefits package and its subpar wages.

One example was HubSpot's "unlimited vacation" offer — a deceptive perk that camouflaged the absence of any structured holiday plan. Consequently, should an employee be fired, HubSpot held no obligations to justify the termination or compensate for unused vacation days.

Lyons recognized that these policies were a cost-cutting strategy leading up to the IPO.

Growth, rather than profitability, is a primary concern in the run-up to an IPO. Hence, it was more pragmatic to bolster sales figures using a low-paid telemarketing team than to contemplate pension plans.

What astonished Lyons was the employees' acceptance of these conditions, primarily because HubSpot had fostered an environment that made them feel exceptional.

Despite the lack of job security, low wages, and pressuring targets, employees were primarily focused on the mission for HubSpot. The company cleverly distracted them with free beer, sweets, and games. It cultivated a sense of team spirit — even though anyone could be dismissed suddenly and without explanation. The promise of feeling special turned out to be a powerful motivation for these employees, despite the reality of their circumstances.

Generating buzz: The key to success for tech companies like HubSpot, regardless of product quality or financial outlook.

It might be baffling to comprehend how a company like HubSpot manages to thrive. The answer lies in the power of buzz — a force so potent that it can enchant both employees and investors alike.

Even organizations manufacturing subpar products or struggling with profitability can succeed if they're armed with the might of positive buzz. This can facilitate a successful IPO.

HubSpot is a perfect example of a company with a less-than-stellar product.

There's an inherent irony that HubSpot, which aimed to sell marketing software tailored for small businesses, didn't utilize its product. Instead, it relied on the traditional techniques of telemarketing and cold-calling.

However, none of these shortcomings mattered as long as they could generate sufficient buzz to allure investors during the public offering.

In the corporate world, crafting buzz is akin to "making a movie."

Companies conjure up a mythical narrative for their business. In HubSpot's case, it was the transformative tale of altering lives through its software. Their youthful co-founder was cast as the charismatic protagonist, making his story a heroic odyssey that painted him as overcoming formidable challenges.

By the time the IPO came along, investors were queued up as if waiting for the premiere of a blockbuster movie.

Even a frail prospectus is powerless against compelling buzz. HubSpot's IPO prospectus openly revealed a history of losses and indicated a considerable possibility of not achieving profitability in the near future.

However, HubSpot had successfully created such powerful buzz and a captivating narrative that the IPO turned out to be a resounding success, catapulting the co-founders to the status of multi-millionaires.

How Lyons used buzz to navigate HubSpot's ageist culture and secure a new role.

Lyons played a significant part in sparking HubSpot's buzz leading up to its IPO.

His previous position as the tech editor for Newsweek piqued the interest of numerous tech blogs, who amplified the buzz by reporting on his transition to HubSpot.

Further enhancing the intrigue, Lyons also began contributing as a writer to HBO's critically lauded TV series, "Silicon Valley," during his tenure at HubSpot.

This amplified buzz proved beneficial for Lyons as it helped him retain his role amid HubSpot's prevalent ageist culture.

Lyons, in his fifties, found it challenging to blend in with the youthful HubSpot clan — predominantly twenty-somethings adhering to a frat-like mentality. However, he valued his health insurance.

Despite the ageist mindset, they co-existed. A telling illustration of HubSpot's ageist stance was an interview with one of its co-founders in the New York Times. He insinuated that experience and graying hair were overvalued in tech, expressing his desire to foster a culture that appealed specifically to "Generation Y."

Lyons shared these interview snippets on his personal Facebook page, inciting a wave of solidarity from his followers.

Many individuals shared personal anecdotes of encountering ageism in the tech industry, expressing surprise that remarks that would provoke controversy in most other sectors were tolerated here.

Eventually, HubSpot and Lyons mutually parted ways as HBO's "Silicon Valley" flourished and he was offered a position to write for Gawker Media's "Valleywag".

In an odd turn of events, HubSpot attempted to cast a negative light on Lyons's departure, crafting an internal memo that suggested he was dismissed.

Stranger yet was the fallout when news about Lyons's book surfaced. A senior manager at HubSpot resigned and another was terminated following a failed attempt to covertly secure the manuscript that ultimately involved the FBI's Cyber Division.

Wrapping it up

The core takeaway from this book:

Tech startups often operate in a manner that is less transparent than it appears. Companies frequently drive towards an IPO, seemingly unconcerned about profitability or product quality. In the end, it's usually only a select group of investors and founders who reap significant rewards when these companies eventually succeed. In contrast, the ordinary employee frequently finds themselves at a disadvantage, with minimal job security and a precarious work-life balance.

Disrupted Quotes by Dan Lyons

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