Venture capital legend, Bill Gurley.

Bill Gurley, a renowned investor, shared insights from his new book, "Running Down a Dream," which advocates for pursuing careers aligned with one's fascinations rather than solely focusing on perceived smart choices or financial gain. Gurley believes that individuals who are genuinely fascinated by their work learn faster, achieve more, and are more likely to succeed, especially with the accelerating influence of AI. He distinguishes "fascination" from "passion," explaining that fascination implies an endless curiosity and a willingness to put in the work to understand nuances and drive innovation, which he sees as crucial for disruption in any field. Unlike the often-cited advice to "chase what you're good at," Gurley argues that a deep fascination provides the intrinsic motivation needed for sustained effort and excellence, which he has observed in successful founders he's backed. Gurley emphasized that finding one's true calling might be a multi-step journey, drawing from his own experience of shifting careers from computer engineering to Wall Street before finding his niche in venture capital. He advises young people not to view initial career paths as failures but rather as stepping stones in the process of discovery. For entrepreneurs, he stresses the importance of ensuring long-term commitment to their ventures, advising them to ask if they would be happy working on their current project 15 years from now, given the significant time investment required. Addressing the question of when fascination might turn into stubbornness, Gurley expressed optimism that genuine fascination, coupled with a "learn-it-all" attitude, can lead to success in almost any field. He acknowledged that some fields, like professional sports, demand exceptional innate talent, but even in those areas, there are numerous support roles where fascination can lead to significant careers. He cited the example of a woman who, fascinated by movies but not aspiring to be an actress, became a highly successful Hollywood agent by exploring the surrounding support roles. Gurley highlighted the importance of peer circles for co-learning and shared knowledge, referencing the story of Jimmy Donaldson (Mr. Beast) and his group of YouTube peers who collectively achieved massive success by constantly learning and sharing insights. He advocates for an "open kimono" approach to sharing ideas, believing that more sharing leads to more opportunities and insights returning to the individual. Reflecting on his biggest career mistake, Gurley recounted missing the opportunity to invest in Google at an $80 million valuation, which he now views as a powerful motivator for his subsequent 22 years in venture capital. His most intellectually appealing investment was OpenTable, where he saw a network effect potential when the company had only three restaurants on its platform, which later scaled to 20,000, validating his initial theory. During the Q&A session, Gurley offered practical advice. For someone at a career crossroads, he suggested an "A/B test" approach: dedicating a week to fully immerse in one career path, then another week in the alternative, to discern which one evokes greater curiosity and engagement. On the topic of AI and health tech, he agreed that technology for health is a promising sector, noting recent breakthroughs in cancer research as evidence. He also pointed out a potential shift in drug discovery, where AI could enable a focus on curing diseases rather than just managing symptoms, which has historically been more profitable for drug companies. Regarding consumer demographic trends with AI, Gurley observed a move towards using AI to simplify decision-making for consumers, especially given the "paradox of choice" created by the internet. He also noted a trend towards targeting the high-end market due to greater disposable income. When considering whether to offer products for free or charge, Gurley advised understanding the target market and the potential for a "freemium" model to attract a large user base, but cautioned that this strategy requires a very large potential market. He also mentioned the growing trend of consumer apps being eligible for insurance reimbursement. For founders, Gurley looks for "unbridled determinism," strong sales ability, and an "unfair go-to-market advantage" that allows a company to acquire customers without relying solely on traditional advertising or sales teams. He believes that many successful outcomes stem from companies that find unique ways to reach their audience, often through product-led growth. On the defensibility of software in the age of AI, Gurley suggested that while some commoditization might occur, software that deals with deterministic data and acts as a system of record (like financial ledgers) will remain defensible. He emphasized the importance of founders staying highly curious about AI's capabilities in their specific fields to avoid being outpaced. When asked about the difference between successful and unsuccessful network effect motions, Gurley highlighted the importance of designing a product where the value to each new customer increases significantly with market penetration. He cited Amazon's Mechanical Turk as an example where the value doesn't scale infinitely with more users, unlike platforms where increased participation genuinely enhances the experience. For entrepreneurs in geographically isolated markets, Gurley advised leveraging virtual communities and digital connectivity to compensate for physical remoteness, drawing parallels to Mr. Beast's success with online peer groups. He also shared his perspective on founder quality versus market fit, stating that while both are ideal, great founders can often pivot and succeed even if their initial product fails, as seen with companies like Discord and Slack. Addressing women founders, Gurley acknowledged the historical funding disparities but noted significant progress over his career. He advised plugging into female founder and VC community groups for support and exposure to success stories, emphasizing the need to combine attention on the problem with celebrating achievements to encourage more women to enter the field. Finally, Gurley cautioned against taking venture capital unless a founder is highly confident of a very large outcome. He pointed out that successive funding rounds can rapidly dilute a founder's equity, making it harder to achieve a significant personal return compared to a smaller, self-funded business. He shared the story of Bert Beverage, who built Tito's Vodka into a highly successful company without external funding, retaining 100% ownership.