For close to thirty years, Bill Gurley has been one of the key figures in Silicon Valley — a general partner at Benchmark whose initial investments in companies like Uber, Zillow, and Stitch Fix played a significant role in shaping contemporary venture capital. Now, after relocating to Austin and stepping back from direct investments, the Texan is applying that same skill for recognizing patterns in a new direction: a book, a foundation, and a policy institute focused on issues he believes he can influence.

The book is titled Runnin’ Down a Dream — a reference to Tom Petty and an assertion that pursuing your passion is not merely idealistic career advice but a genuine competitive approach, which is increasingly critical as AI swiftly transforms the job market. The foundation, named the Running Down a Dream Foundation, will distribute 100 grants of $5,000 each year to individuals who require financial support to take a leap they’re hesitant about.

We connected with Gurley to discuss it all — including his perspective on the surreal reality that many of his former tech peers now wield significant influence in Washington, why he considers the intense work culture embraced by numerous young founders, referred to as the 996 grind, less concerning than it seems, and what the implications of AI are for one’s career. The following has been condensed for brevity and clarity. Our complete conversation with Gurley is scheduled to air Tuesday on TC’s StrictlyVC Download podcast.

What inspired you to write this book?

I went through a period where I immersed myself in biographies — individuals from various backgrounds and eras — and I began to identify recurring themes similar to those I observed in market trends. I took notes on these patterns. A couple of years later, I was invited to speak at the University of Texas, revisited the notes, and created a presentation. They uploaded it to YouTube, which caught the attention of James Clear — author of Atomic Habits — who shared it. That sparked my contemplation about writing a book. During my transition away from venture capital and contemplating my next steps, it became clear that I didn’t wish to write about VC or Uber or any of that; instead, I wanted to pursue something with a broader purpose.

Your research at Wharton revealed that about 60% of individuals would approach their careers differently if they had the chance to start over. Were you surprised by this finding? Why?

When we initially conducted it as a SurveyMonkey poll, we received a response of seven out of ten. Upon conducting a more thorough study with Wharton, we found it was six out of ten. One thing that stands out is our phrase in the book — life is a use it or lose it proposition — and when you’re young, it’s challenging to comprehend that concept. It’s tough to fast-forward through your time and appreciate its value. Daniel Pink has done extensive work on what he terms regrets of inaction — what burdens people the most as they age is the missed opportunities, the chances not taken. This sentiment resonates across various cultures and regions. Moreover, many well-meaning parents prioritize creating economic security for their children over encouraging them to truly pursue their passions. With AI on the horizon, that may not have been the best approach.

Pursuing your passion seems like simpler advice for those with a financial safety net. What would you say to someone living paycheck to paycheck?

Several points. Initially, the book highlights individuals who began from the very bottom and achieved success — [celebrity hairstylist and entrepreneur] Jen Atkins moved to LA with merely $200. The book conveys that you don’t need to begin anywhere other than right at the start. Secondly, if you’re living paycheck to paycheck, I wouldn’t suggest quitting your job. Instead, I’d recommend utilizing your spare time to create a document on your phone detailing what your aspirations might be. Learn. Prepare to leap before you leap. And lastly — this is the foundation’s purpose. The concluding page of the book explains: we will grant 100 awards annually of $5,000 to individuals in that exact situation, who can prove in an application that they have thoughtfully considered their aspirations but need some assistance in achieving them.

You have been a vocal critic of regulatory capture — the concept that large corporations manipulate regulation to solidify their positions.

I delivered a speech on regulatory capture a few years ago — at the All-In Summit — and during that discussion, I expressed my concern that AI companies would attempt to leverage regulation for their protection. I believe that is occurring now. Conversely, there are valid concerns: Jonathan Haidt’s book Anxious Generation has been a bestseller for nearly two years, asserting that social media has negatively impacted children, supported by academic studies. Many argue we should have anticipated the challenges posed by social media and should do so with AI as well. The dilemma is that the entities advocating for AI regulation the most are the companies involved themselves, leading to my skepticism. There’s also a global aspect — if US AI becomes entangled in state-specific regulations while Chinese models operate freely, we’ll end up mired in bureaucracy. I often pose the question: what are your top five regulations in history, and how did they succeed? Do you truly believe individuals at the state level in random states can create effective AI regulations that genuinely work?

It’s quite surreal that several notable individuals from your sector now exert significant influence in Washington. What is your view on that?

It’s quite ironic. If you revisit my regulatory capture discussion, who could have predicted that just a few years later David Sacks would become [special advisor for AI and crypto in the White House]?

In 2018, Mike Moritz from Sequoia stated in the FT that Americans would fall behind China if they didn’t begin working harder. While it was contentious at the time, many young founders here appear to have since adopted a grueling work culture — the 996 ethos. What are your views on this trend?

I find it somewhat appealing, to be honest. I believe Silicon Valley became quite complacent during COVID — people weren’t returning to the office, and the culture softened in a way I had not witnessed in my years there. I’ve been to China six times, and I understand what Michael Moritz described regarding our potential downfall not being due to intelligence but a stronger work ethic. However, here’s the fact: if you examine successful individuals across various fields, we admire it when an athlete practices for 12 hours or when an artist dedicates themselves obsessively to their craft. Nobody criticizes Jordan for lacking work-life balance. Yet, we don’t apply the same reasoning to entrepreneurship. If those founders are passionate about their work and feel this is the critical moment to put in the effort, that’s precisely the essence of my book: discover what drives that feeling within you.

You discuss mentorship in your book. What constitutes an excellent mentor relationship, and how can individuals find one?

The foremost aspect is to eliminate the ideal often suggested in self-help circles: ‘go find a mentor,’ which leads everyone to cold-call someone who’s unrealistic and unattainable, resulting in failure. For those who seem unreachable, I refer to them as aspirational mentors — create a profile of them, similar to my concept of the dream job folder. Collect materials of all their writings, podcasts, interviews, and study their work. You can gain significant insights from figures without direct communication, especially in today’s world. For your genuine mentors, aim two levels down from your initial target. Identify someone — tools like LinkedIn facilitate this — and be the first to contact them and request mentorship, as they will appreciate it. They’ll feel honored that you recognized them. Imagine receiving your first request to be a mentor; it’s a gratifying experience. You’ll have much greater success with this approach than trying to reach too high.

I have a humorous anecdote: I began receiving numerous requests from individuals wanting to enter venture, which prompted me to create a three-page PDF titled “So You Want to Be a VC.” Hidden on the third page was essentially — go do X, go do Y, go do Z, then come back and tell me how it went. The number of individuals who actually engaged with me after receiving that document was a fraction of those it was sent to. It’s amusing how the pool thinned when they were given a bit of homework.

You began working on this book before the full effects of AI were evident. Does that influence how individuals should approach their careers?

If you’re adhering to the conventional route — going through your university’s career center, signing up on a list, waiting for a recruiter to sift through thirty individuals in twenty-minute intervals — you risk appearing like a mere cog. You seem mass-manufactured. For that demographic, AI seems daunting, and rightly so. However, if you are carving your unique path, utilizing the strategies outlined in the book, becoming what I call a candidate of one — someone with an intentionally unique trajectory — then each tool presented in this book is enhanced by AI. The ease of learning has never been greater than it is today, throughout all of human history. If you’re embracing it, if you’re becoming the most AI-savvy individual in your domain, this phenomenon is nothing short of a superpower.