Live Work Work Work Die: A Journey Into the Savage Heart of Silicon Valley
by Corey Pein · 23 Apr 2018 · 282pp · 81,873 words
and win. It’s the perfect crime—when it works. In a 2013 Shark Tank–style live investor pitch, the founder of a startup called Zenefits, Parker Conrad, feistily promised “to mess stuff up for two very large industries”—insurance and human resources. “If you’re an insurance broker,” Conrad explained
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who received kickbacks from insurance companies would have every incentive to push worse policies on their clients, ultimately screwing over everybody who paid premiums.) However, Zenefits found a loophole. It was, in Conrad’s opinion anyway, not explicitly illegal for a broker—which
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Zenefits was—to provide its clients with free software and services—as Zenefits did—while at the same time receiving compensation from insurance providers that might otherwise be illegal. Because its clients weren’t paying Zenefits to act as an insurance broker, the compensation
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was kosher … or so Conrad hoped. In most states, insurance regulators failed to notice Zenefits’ egregious end run around consumer protection rules. But Utah regulators did notice. They cited the company for violations and were all set to ban it
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. But where there was cash, there was hope. Coached by the investors who had poured $84 million into the startup, Zenefits “went to the mat” with the government of Utah. Zenefits staged a petition and made itself a techie cause célèbre. Then the company hired “some folks” in Utah, as Conrad put
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state’s largest political fundraising committee; and the former executive director of the Utah Republican Party. After successfully beating back the pesky regulators in Utah, Zenefits joined the unicorn herd with a $4.5 billion valuation in 2015. The management reportedly blew a lot of that money on motivational bacchanals that
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investigation brought to light deficiencies” in company practices—although of course it was state regulators who first pointed out those unlawful “deficiencies.” Sacks then said Zenefits was rebranding as the Compliance Company and would use its experience to help clients stay out of trouble with regulators and avoid waste, fraud, and
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Wolff, Stephen S. Worldwide Developers Conference Wozniak, Steve Xerox X Prize Foundation Yahoo Yarvin, Curtis Guy Y Combinator Yelp YouTube YouTube Kids Zachary, Gregg Pascal Zenefits Zuckerberg, Mark ZunZuneo Zynga About the Author Corey Pein is an investigative reporter and a regular contributor to The Baffler. A former staff writer for
Brotopia: Breaking Up the Boys' Club of Silicon Valley
by Emily Chang · 6 Feb 2018 · 334pp · 104,382 words
$1.2 billion. The list of “begats” goes on. Sacks went on to become COO of the fast-growing HR software start-up Zenefits. When the founder of Zenefits, Parker Conrad, was kicked out amid accusations of cheating state compliance regulations and creating a bro-y culture that led to “sex in
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promoted to CEO. Sacks promptly brought in Peter Thiel as a board member. Even though the valuation of Zenefits was slashed amid the cheating scandal, it still reached $2 billion. (Sacks has since left Zenefits.) And this is just a partial list. The PayPal Mafia became so dominant that in 2017 Adam
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Politics, Nov. 27, 2017, https://stanfordpolitics.org/2017/11/27/peter-thiel-cover-story. “This is college journalism written over 20 years ago”: Kara Swisher, “Zenefits CEO David Sacks Apologizes for Parts of a 1996 Book He Co-wrote with Peter Thiel That Called Date Rape ‘Belated Regret,’” Recode, Oct. 24
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, 2016, https://www.recode.net/2016/10/24/13395798/zenefits-ceo-david-sacks-apologizes-1996-book-co-wrote-peter-thiel-date-rape-belated-regret. “I do believe in diversity”: David Sacks
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Closing the Chapter on Compliance Issues,” interview by author, Bloomberg, Oct. 18, 2016, video, 12:23, https://www.bloomberg.com/news/videos/2016-10-18/zenefits-ceo-on-closing-the-chapter-on-compliance-issues. “sleep and get some air-conditioning”: Max Levchin, “PayPal Co-Founder Max Levchin: Studio 1.0 (02
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”: Thiel, Zero to One, 173. “I ended up recruiting”: Ibid. “sex in the stairwells”: Rolfe Winkler, “Zenefits Once Told Employees: No Sex in Stairwells,” Wall Street Journal, Feb. 22, 2016, https://www.wsj.com/articles/zenefits-once-told-employees-no-sex-in-stairwells-1456183097. Mafia’s “dynastic privilege”: Adam Pisoni, “In Defense
The Power Law: Venture Capital and the Making of the New Future
by Sebastian Mallaby · 1 Feb 2022 · 935pp · 197,338 words
similar disasters, but they could hardly count on doing so. In 2014, Andreessen Horowitz had led two investment rounds in an online insurance startup called Zenefits. The company had become one of a16z’s largest positions, and the partnership had agitated for growth: later, the founder recalled his a16z board member
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barking, “You guys gotta get your heads out of your asses, start focusing on going big here.”[4] Goaded to expand by all means possible, Zenefits attained a valuation of $4.5 billion in the extraordinarily short period of just over a year. But by 2016 the company was careening off
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firm’s valuation was slashed by more than half, from $4.5 billion to $2 billion. The Zenefits story did have one redeeming feature. Andreessen Horowitz, being a real venture firm, quickly ejected the Zenefits founder when the legal problems surfaced. A new chief executive was installed, and the corporate motto changed
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from “ready, fire, aim” to “operate with integrity.”[6] But it was easy to imagine a hybrid of the Zenefits and Theranos cases in which a hands-on venture shop invested alongside passive financiers. The passive financiers might be amateurish outsiders, as in the Theranos
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-off to oversee the company responsibly. The following year, this danger turned out to be more than just theoretical. Around the time that Theranos and Zenefits went awry, Bruce Dunlevie of Benchmark was preoccupied with a unicorn called WeWork. Benchmark had first invested in WeWork in 2012, mainly because of its
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tapped into something powerful in the zeitgeist: the aesthetic of a rising generation of workers—entrepreneurial, hip, creative, and transient. By the time Theranos and Zenefits were imploding, in 2016, Benchmark’s WeWork stake had generated hundreds of millions of dollars in paper profits. Along the way, however, something fundamental had
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Dunlevie opposed this move: if the founder veered off track, Benchmark would need the votes to force a change—just as a16z had done with Zenefits. At the same time, however, Dunlevie didn’t want to block the financing: WeWork needed the capital. Balancing these considerations, Dunlevie registered his opposition politely
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billion. The gap between this paper gain and what might be the actual gain was eating him alive: What if Uber went the way of Zenefits or Theranos? Many of Benchmark’s limited partners had already booked profits from his presumed grand slam: endowment investment officers had taken bonuses and bought
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. In 2020, venture-backed IPOs raised $38 billion, by far the largest amount ever.[89] But these were merely hints of change, and the Theranos-Zenefits risk still haunted the venture industry. Whether Son would stick with his new standards was anybody’s guess, and other growth-stage specialists, including Yuri
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TO NOTE REFERENCE 2 Carreyrou, Bad Blood, 16. BACK TO NOTE REFERENCE 3 William Alden, “How Zenefits Crashed Back Down to Earth,” BuzzFeed, Feb. 18, 2016. BACK TO NOTE REFERENCE 4 William Alden, “Startup Zenefits Under Scrutiny For Flouting Insurance Laws,” BuzzFeed, Sept. 25, 2015. BACK TO NOTE REFERENCE 5 Rolfe Winkler
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, “Zenefits Touts New Software in Turnaround Effort,” Wall Street Journal, Oct. 18, 2016. BACK TO NOTE REFERENCE 6
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(a16z), 290–300, 311 Clubhouse, 14 Instagram, 213 Nicira, 293–95, 296, 379 Okta, 295–96, 379 Skype, 297–98, 299 Uber, 353–55, 378 Zenefits, 341–42 Anduril, 403–4 angel investing, 85, 175–76, 311, 316 Facebook, 198–99, 208 Google, 173–76, 178–79, 215 animal husbandry, 1
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revolt, 194–97, 272, 303 YouTube, 10, 12 Sequoia Capital’s investment, 306–7, 309–10, 313 Yozma Group, 396 Yu, Gideon, 273–74 Z Zenefits, 341–42 Zhang Fan, 238–41 Zhang Tao, 244, 246 Zhang Ying, 227–28 Zilog, 432n Zimride, 357 Zingale, Tony, 313 Zoom, 330, 333 Zuckerberg
This Could Be Our Future: A Manifesto for a More Generous World
by Yancey Strickler · 29 Oct 2019 · 254pp · 61,387 words
—fast growth and big valuations defined the mainstream idea of success. In 2014, a New York Times article profiled an HR software start-up called Zenefits, which, the lead sentence explains, is “one of the fastest-growing companies in recent Silicon Valley history.” The profile glowingly notes the company’s fast
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growth, A-list Silicon Valley investors, and a recent $4.5 billion “unicorn” valuation. Zenefits was the newest zeitgeist-shaking success. But in the article, Zenefits’ founder and CEO, a man named Parker Conrad, gives a series of startling quotes that clash with the breathless tone
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than the reality right in front of us. This is perfectly encapsulated in the story’s headline: “Zenefits’ Leader Is Rattling an Industry, So Why Is He Stressed Out?” Why was Conrad stressed? Because Zenefits was a quickly growing service that aggressively raised nearly half a billion dollars in venture capital money
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regulations to keep it up. The Times reported that the company’s board members had been pushing for faster growth. Though extreme, the story of Zenefits is not unusual. To fulfill the hyperexpectations that investors and others have, people run themselves ragged and take dubious shortcuts to get there. Many of
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. We weren’t interested in playing the game others were playing. We had deliberately taken ourselves out of that race. Kickstarter was the opposite of Zenefits and Groupon. While they raised huge amounts of venture capital and set expectations for a big payday, we saw the hypergrowth path for what it
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and Extrinsic Goals,” March 1996). “recent Silicon Valley history”: The New York Times story about Zenefits ran on September 20, 2014. pushing for faster growth: Eighteen months later, the New York Times profiled Zenefits’ downfall as well (“Zenefits Scandal Highlights Perils of Hypergrowth at Start-Ups,” February 17, 2016). “it does seem like
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Williams, J. D., 31 Woodward, Bob, 11 Yahoo, 71, 85 Yale University, 185 YouTube, 55 You’ve Got Mail, 46 Z generation, xiv–xv, 215 Zenefits, 95–96, 100 Zinkin, Harold, 185 Zuckerberg, Mark, 53, 98, 109–10 ABCDEFGHIJKLMNOPQRSTUVWXYZ ABOUT THE AUTHOR Yancey Strickler is the cofounder and former CEO of
Why Startups Fail: A New Roadmap for Entrepreneurial Success
by Tom Eisenmann · 29 Mar 2021 · 387pp · 106,753 words
cut legal, regulatory, or ethical corners. Uber, for example, was accused of encouraging its employees to book and then cancel rides with its rival, Lyft. Zenefits, a licensed health insurance broker, created software that allegedly allowed its new salespeople to cheat on state licensing exams to sustain the startup’s rapid
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that scale too quickly. Some survive by trimming head count, cutting marketing, and refocusing on more loyal and profitable customer segments. Birchbox, Blue Apron, Groupon, Zenefits, and Zynga are examples. However, for Fab and many other startups, such as Beepi, Homejoy, Munchery, and Nasty Gal, the Speed Trap is fatal. The
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: Kate Taylor and Benjamin Goggin, “49 of the Biggest Scandals in Uber’s History,” Business Insider website, May 10, 2019. Zenefits, a licensed health insurance broker: Claire Suddath and Eric Newcomer, “Zenefits Was the Perfect Startup. Then It Self-Disrupted,” Bloomberg Businessweek, May 9, 2016. It helps to have a radar detector
The Optimist: Sam Altman, OpenAI, and the Race to Invent the Future
by Keach Hagey · 19 May 2025 · 439pp · 125,379 words
specialty foods, with no discernable thesis. The one thing connecting the investments was that most of them had gone through Y Combinator, including HR startup Zenefits, supply chain logistics platform Flexport, video chat language learning service Verbling, digital construction marketplace BuildZoom, meal replacement company Soylent, and online divorce service Wevorce. One
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best?’ ” “By late 2014, this heuristic started to not work anymore, because enough people knew to do this,” Thiel said. He and Altman had identified Zenefits—a health benefits broker that gave away free HR software to small businesses in the hopes of making commissions from going on to sell them
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a few years, unable to meet the optimistic growth targets required to merit such a valuation and struggling with its relationships in the healthcare industry, Zenefits blew up and the investment went basically to zero. (David Sacks, a friend of Thiel’s from college and a fellow Stanford Review writer and
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, who had spent the prior two years working at Hydrazine, joined Teespring as its VP of business development. The following January, their brother Max joined Zenefits, which was in that same YC batch, moving from Chicago where he had been working as a trader at the Sequoia-backed high-frequency trading
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, 4–5, 7, 135, 140–46, 164, 168, 176, 210, 212, 264, 300 Yuen, Phil, 82 Zaremba, Wojciech, 184, 191, 218 Zefer consulting company, 62 Zenefits HR startup, 138–39, 156–57 “zero-shot” responses, 220–21 Zilis, Shivon, 234, 277 Zodiac Aerospace, 225 Zuckerberg, Mark, 6, 96, 98, 137, 212
The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power
by Max Chafkin · 14 Sep 2021 · 524pp · 130,909 words
-rape-book; Ryan Mac and Matt Drange, “Donald Trump Supporter Peter Thiel Apologizes for Past Book Comments on Rape,” Forbes, October 25, 2016; Kara Swisher, “Zenefits CEO David Sacks Apologizes for Parts of a 1996 Book He Co-wrote with Peter Thiel That Called Date Rape “Belated Regret,’ ” Recode, October 24
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, 2016, https://www.vox.com/2016/10/24/13395798/zenefits-ceo-david-sacks-apologizes-1996-book-co-wrote-peter-thiel-date-rape-belated-regret; Andrew Granato, “How Peter Thiel and the Stanford Review Built a
Traffic: Genius, Rivalry, and Delusion in the Billion-Dollar Race to Go Viral
by Ben Smith · 2 May 2023
. He’d come to believe that BuzzFeed News and I had taken a hard line on one of his companies, a failed insurance startup called Zenefits, specifically in order to prove our independence from him. The thought hadn’t crossed our minds; we hadn’t thought, or realized, he was that
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–86 and Peretti’s speeches, 200 and shifting media environment, 128 and social engagement on Facebook, 272–73 and Upworthy, 181 Z Zaleski, Katharine, 107 Zenefits, 299 Zuckerberg, Mark and backlash against progressive activism, 132 and BuzzFeed’s news and social content, 160–64 and BuzzFeed’s traffic growth, 205–8
Lab Rats: How Silicon Valley Made Work Miserable for the Rest of Us
by Dan Lyons · 22 Oct 2018 · 252pp · 78,780 words
trip to San Francisco I met a group of German businessmen whose companies had sent them on a two-week safari. When I met them, Zenefits, one of the hottest unicorns, had just booted out its CEO, Parker Conrad, in a scandal that involved allegations of cheating on licensing tests and
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letting unlicensed brokers sell insurance policies, as well as having an out-of-control frat-boy party culture. (Conrad and Zenefits would later settle charges brought by the Securities and Exchange Commission that they misled investors; they paid a fine but did not admit or deny
Empire of AI: Dreams and Nightmares in Sam Altman's OpenAI
by Karen Hao · 19 May 2025 · 660pp · 179,531 words
president. Max, who had studied computer science at Duke and worked briefly at Microsoft before becoming a trader, switched to working at another YC company, Zenefits, in 2014. Two years later, he would join Sam and Jack at Hydrazine Capital. During that time, both younger brothers moved in with Sam for
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Yom Kippur, 326–27 YouTube, 34, 51–52, 102–3, 136, 244–45, 334 Yudkowsky, Eliezer, 319–20 Z Zaremba, Wojciech, 59, 152, 181–82 Zenefits, 36 Zilis, Shivon, 63, 320–21, 324, 384 Zoloft, 329, 330 Zoph, Barret, 247, 381–82, 387, 404, 406 Zuboff, Shoshana, 101 Zuckerberg, Mark, 38
Gilded Rage: Elon Musk and the Radicalization of Silicon Valley
by Jacob Silverman · 9 Oct 2025 · 312pp · 103,645 words
Pattern Breakers: Why Some Start-Ups Change the Future
by Mike Maples and Peter Ziebelman · 8 Jul 2024 · 207pp · 65,156 words
Insane Mode: How Elon Musk's Tesla Sparked an Electric Revolution to End the Age of Oil
by Hamish McKenzie · 30 Sep 2017 · 307pp · 90,634 words
Drunk: How We Sipped, Danced, and Stumbled Our Way to Civilization
by Edward Slingerland · 31 May 2021
The Cult of We: WeWork, Adam Neumann, and the Great Startup Delusion
by Eliot Brown and Maureen Farrell · 19 Jul 2021 · 460pp · 130,820 words