Bill Gurley

Bill Gurley
Born	John William Gurley 10 5, 1966
Birthplace	Dickinson, Texas, U.S.
Nationality	American
Occupation	Venture capitalist
Employer	Benchmark
Known for	General partner at Benchmark, early investor in Uber
Website	[abovethecrowd.com Official site]

John William Gurley (born May 10, 1966), known professionally as Bill Gurley, is an American venture capitalist and general partner at Benchmark, a prominent Silicon Valley venture capital firm based in San Francisco, California. Over a career spanning nearly three decades in technology investing, Gurley has become one of the most recognized figures in the venture capital industry, known for his investments in companies such as Uber, OpenTable, Zillow, and Stitch Fix, as well as for his outspoken commentary on startup valuations, initial public offering processes, and market cycles. His blog, Above the Crowd, has served as an influential platform for his analysis of technology markets and venture capital dynamics. Standing six feet nine inches tall, a former collegiate basketball player from small-town Texas, Gurley followed an unconventional path from Wall Street analyst to one of Silicon Valley's most closely watched investors. In recent years, he has been a vocal critic of what he has described as dangerous trends in private market fundraising and has spoken publicly about the potential for a correction in the artificial intelligence sector.

Early Life

Bill Gurley was born on May 10, 1966, in Dickinson, Texas, a small city in Galveston County located in the Houston metropolitan area. He grew up in the area and attended local schools. Gurley's early life in a modest Texas community would later become a recurring theme in his public commentary, as he has frequently discussed the importance of career exploration and risk-taking, drawing on his own experience of leaving a small town to pursue opportunities in technology and finance.

Gurley played basketball during his school years, eventually competing at the collegiate level. His height of six feet nine inches made him a natural fit for the sport, and his background in competitive athletics has been cited in profiles as an influence on his later approach to business and investing.

Education

Gurley attended the University of Florida, where he earned his undergraduate degree. He later pursued graduate studies at the McCombs School of Business at the University of Texas at Austin, where he received his MBA. His business school education provided a foundation in finance and corporate strategy that would inform his subsequent career as both a Wall Street analyst and a venture capitalist.

Career

Early Career and Wall Street

Before entering venture capital, Gurley worked as a design engineer at Compaq Computer, gaining firsthand experience in the technology hardware industry. He subsequently transitioned to Wall Street, where he worked as a research analyst. During his time in equity research, Gurley covered technology companies and developed a deep understanding of business models, competitive dynamics, and valuation methodologies in the technology sector. His analytical rigor and ability to identify transformative business models became hallmarks of his professional reputation during this period.

Benchmark Capital

Gurley joined Benchmark Capital (later known simply as Benchmark) as a general partner, becoming one of the firm's most prominent investors. Benchmark is known for its equal-partnership structure, in which all general partners share equally in the firm's economics, a distinctive model in the venture capital industry. The firm has historically focused on early-stage investments in technology companies.

At Benchmark, Gurley built a portfolio that included a range of notable technology companies across multiple sectors. His investment approach has been characterized by a focus on companies with strong marketplace dynamics, network effects, and scalable business models.

Notable Investments

Gurley's most prominent investment was in Uber, the ride-hailing company, in which Benchmark invested at an early stage. The Uber investment became one of the most profitable venture capital deals in history, though it also involved significant public controversy regarding the company's governance and the eventual departure of co-founder and CEO Travis Kalanick. Gurley served on Uber's board of directors for several years, and the investment and its associated boardroom dynamics received extensive media coverage.

Beyond Uber, Gurley made investments in a number of other technology companies that achieved significant scale. He was involved in Benchmark's investment in OpenTable, the restaurant reservation platform that went public and was later acquired by the Priceline Group. He also invested in Zillow, the online real estate marketplace.

Gurley was associated with Benchmark's investment in Stitch Fix, the online personal styling service, which raised a Series B round of funding. The company later went public in 2017. Additionally, Benchmark under Gurley's involvement invested in DogVacay, a pet-sitting marketplace that raised $6 million in a round led by Benchmark.

Other investments in Gurley's portfolio included Sailthru, an email marketing and personalization platform that raised a Series B round, and HackerOne, a bug bounty and vulnerability coordination platform that emerged with $9 million in funding. Gurley was also linked to investments associated with Jason Kilar's startup Vessel, which received funding as reported in 2014.

Views on Startup Valuations and Market Cycles

Gurley has been one of the most prominent voices in Silicon Valley warning about the risks of inflated private market valuations and unsustainable fundraising practices. Beginning in the mid-2010s, he publicly expressed concern that many highly valued private companies — often referred to as "unicorns" (private companies valued at $1 billion or more) — were operating under conditions that could lead to significant losses for late-stage investors and employees.

In October 2015, Gurley warned that Silicon Valley was on what he described as a "dangerous path," cautioning that the proliferation of unicorns and the terms associated with late-stage private fundraising rounds posed systemic risks. Earlier that year, in March 2015, he had stated that what he saw as the end of the easy-money era in Silicon Valley was approaching.

In April 2016, Gurley escalated his warnings, telling startups to beware of what he termed "dirty" fundraising terms — provisions in late-stage funding rounds that could disadvantage earlier investors and common shareholders. He argued that the structure of many late-stage rounds, including liquidation preferences and ratchet provisions, created misaligned incentives and obscured the true risk profile of these investments.

During the 2008 financial crisis, Gurley and Benchmark had similarly advised portfolio companies to conserve capital and prepare for an extended downturn. He offered guidance on how startups could survive difficult economic conditions without resorting to mass layoffs.

Views on IPO Process

Gurley has been a persistent critic of what he views as structural flaws in the traditional initial public offering process, particularly the role of investment banks as underwriters. He has argued that the conventional IPO process systematically underprices shares, transferring wealth from companies and their existing shareholders to institutional investors who receive favorable allocations. He has publicly advocated for alternative approaches to going public, including direct listings, which allow companies to list their shares on a stock exchange without issuing new shares or using traditional underwriters.

His views on IPOs gained renewed attention in connection with the Figma IPO, which was discussed in a February 2026 report by the Financial Times.

Views on Artificial Intelligence

In January 2026, Gurley publicly stated his view that a "correction" in the artificial intelligence sector was inevitable, warning that the level of investment and enthusiasm around AI could lead to a market adjustment. In an appearance on Yahoo Finance's Opening Bid Unfiltered podcast, he discussed whether AI was creating the conditions for the next market correction.

In December 2025, Gurley appeared on The Tim Ferriss Show, where he discussed navigating the AI era and its implications for technology investors and entrepreneurs.

Career Advice and Public Speaking

In addition to his investment activities and market commentary, Gurley has spoken publicly about career development and professional risk-taking. In February 2026, TechCrunch reported that Gurley advised professionals that "the worst thing you can do for your career is play it safe," arguing that in the current economic and technological environment, excessive caution was a greater risk than bold action.

Gurley has spoken about the topic of career regret, with Entrepreneur magazine reporting that he spent a decade researching the subject. According to the publication, Gurley has emphasized that career regret is a more lasting burden than career failure, and he has encouraged individuals to pursue work they find meaningful rather than defaulting to conventional or safe career paths.

In February 2026, Gurley was scheduled to appear at the Commonwealth Club of California for an event titled "How to Thrive in a Career You Actually Love," described in promotional materials with the framing: "Life is a use-it-or-lose-it situation… Shouldn't you try to spend it doing something you love?"

Above the Crowd Blog

Gurley has maintained a blog titled Above the Crowd, which has served as a platform for his long-form analysis of technology markets, business models, and venture capital dynamics. The blog has been cited by major financial and technology news outlets and has been a vehicle for some of his most influential arguments about startup valuations, marketplace dynamics, and the IPO process. The blog's name became closely associated with Gurley's public identity in the technology investment community.

Recognition

Gurley has been consistently listed among the top venture capitalists in the technology industry. Forbes has maintained a profile of Gurley as part of its coverage of notable figures in venture capital and finance.

In February 2016, Gurley and Benchmark were recognized at the 9th Annual Crunchies Awards, the annual technology industry awards ceremony organized by TechCrunch.

TechCrunch described Gurley in 2026 as "one of the most influential voices in Silicon Valley" over the course of nearly three decades. His commentary on market cycles, IPO reform, and startup governance has been covered by The Wall Street Journal, Bloomberg, The New York Times, Fortune, Financial Times, and other major publications.

His appearances on podcasts and at speaking events have extended his influence beyond the venture capital community. His 2025 appearance on The Tim Ferriss Show and his 2026 engagement at the Commonwealth Club reflect his continued relevance as a commentator on technology, investing, and career strategy.

Legacy

Bill Gurley's career at Benchmark has spanned a period of transformative change in the technology industry, from the aftermath of the dot-com bubble through the rise of mobile computing, the sharing economy, and artificial intelligence. His investment in Uber stands as one of the defining venture capital transactions of the 2010s, both for its financial returns and for the governance challenges it entailed.

Gurley's public commentary on startup valuations, fundraising practices, and the IPO process has influenced industry discourse and contributed to broader conversations about market discipline in the technology sector. His warnings about inflated unicorn valuations in 2015 and 2016 presaged a period of retrenchment in the private markets, and his subsequent commentary on the AI sector in 2025 and 2026 suggests a continuation of this role as an industry watchdog.

His blog, Above the Crowd, has been a model for the analytical, long-form investor commentary that became more common in the venture capital community during the 2010s and 2020s. By publishing detailed analyses of business models and market dynamics, Gurley helped establish a template for transparent, public-facing investor communication.

As of 2026, Gurley remains active as a general partner at Benchmark and continues to speak publicly on topics related to technology investing, artificial intelligence, and career development.