Evening Reading | Conversation with Silicon Valley VC Bill Gurley: Don't Play It Safe, Become an "AI-Empowered" Version of Yourself

Source: Silicon Valley Girl

Editor: Felix, PANews

Summary: Any work that can be called a “craftsman’s job” is hard to replace because AI is not good at handling the subtle nuances involved.

Bill Gurley has witnessed countless careers rise and fall over 25 years. The companies he invested in are valued at over $50 billion. Those who lose everything are not the risk-takers, but the conservative ones.

In the Silicon Valley Girl podcast, Bill Gurley mainly discusses how AI is changing work, which professions will disappear first, and what actions can be taken if jobs are already shrinking. PANews has compiled key highlights from the conversation.

Host: I had prepared a question, but just now there was news that Block is laying off nearly half of its staff to boldly embrace AI. Should people be afraid?

Bill: Yes, but with some conditions. AI tools have been around for two or three years now—they’re here to stay and won’t be rolled back or disappear. The most direct advice for anyone in any field to protect themselves from AI’s impact is: try to become an “AI-empowered” version of yourself. You need to understand the boundaries of AI capabilities in your domain and use it as much as possible. The more you use it, the more prompts you’ll think of, and you’ll start to understand its strengths. If you don’t actively leverage it, you’ll fall behind those who do.

What’s novel about this is that it’s impacting white-collar jobs, which many previously considered “safe.” If you’re truly replaced, ask yourself: is this really the work you love and want to do? If not, it might be an opportunity to find what you’re truly passionate about.

Host: We used to think IQ could help us get through life smoothly. But now you say “playing it safe/staying steady is the riskiest move.” Can you explain?

Bill: Unfortunately, many career counselors, mentors, and parents tend to push people toward what they see as “safe” jobs. But if you don’t love your work, according to a 2023 Gallup poll, over 50% of people lack engagement at work, with only about 23% truly “invested.” If you’re in a role you don’t care about and lack motivation to improve, you’re like a sitting target in these changes. Parents’ original intention is to ensure financial stability, but life is only once. If you find something you’re intensely curious about, you can create a huge gap between yourself and others, and economic rewards will follow.

Host: Can you list three traits of people who don’t “play it safe”? What do they do every day?

Bill: First, they allow themselves to pursue careers they once thought impossible. For example, Danny Meyer, founder of Shake Shack, initially planned to go to law school and become a lawyer, but encouraged by his uncle, he faced his childhood hobby of exploring good restaurants and writing diaries, and eventually entered the food industry. Second, they hone their skills and keep learning. If you love something, curiosity drives you to keep learning; absorbing new information energizes you. Conversely, being forced to take classes in areas you dislike only drains your energy. Third, they stay at the forefront of knowledge. AI and large language models record the best practices already written down, but the cutting-edge knowledge being explored today isn’t in the models yet. If you’re someone who masters this frontier knowledge, you’re ahead of the AI models.

Host: When evaluating founders, what behaviors are considered “not playing it safe”?

Bill: I believe the entire venture capital industry has recognized that when choosing founders, you can’t have a “play it safe” mindset. The best and smartest people are highly independent thinkers—they naturally break conventional thinking. Some might seem “crazy” because they’re overly dogmatic or firm in their beliefs, but that’s actually true. And I’m not the only one saying this. If you study VC articles, you’ll find a trend of seeking such personality traits. It traces back to Steve Jobs’ “crazy ones” ad.

Host: It seems now everyone should adopt this “crazy” mindset to succeed because you’re becoming the entrepreneur of your own life, right?

Bill: Yes, I think that’s a good way to put it. Especially in certain fields, this new technology has brought so much disruption that if you don’t take control of your career, you’re likely to face risks. I often say that if you’re a highly proactive person confident in driving your career, these tools are essentially a “jetpack.” If you want to learn proactively, there’s never been a better time—except with AI. And podcasts, like the ones you produce, are everywhere on YouTube, with interviews that allow you to learn at an unprecedented speed. That’s also why I don’t react much to “AI anxiety”—because anxiety can freeze you. The right move now is to run as fast as you can.

Host: Sometimes I scroll through my phone and hear people, including you, say: “We have a window of opportunity closing, so we should work very hard now to seize it.” Can you elaborate? How much time do we have? How hard should we work?

Bill: I don’t think the window is necessarily closing; it’s just that this tool is arriving so quickly, with so many functions, that everyone must figure out what it can do in their industry as soon as possible. I dislike dystopian narratives, like Ray Dalio’s, which are often the most extreme doomsday prophets and tend to dominate the discourse. I believe such talk isn’t healthy. This anxiety is five times higher in the US than in China. While it can sometimes motivate action, it’s more likely to paralyze people. Instead of worrying, the best approach now is to run as fast as you can.

Host: You also mentioned that “forgetting or abandoning what once made you successful” is very important. How do you do that?

Bill: There’s a saying: “Strong opinions, flexible adherence.” Having strong opinions makes it easier to act, but you should never treat any belief as sacred or unchangeable. If you develop a habit of continuous learning and realize that clinging to old ideas carries risks, you can better judge when to let go of past experiences.

Host: With so many intriguing things, how do you find a direction that can become a lifelong career? And what if you choose wrong?

Bill: You can try turning hobbies into careers. For example, I worked as an engineer for two and a half years, and at night I read Peter Lynch’s “One Up on Wall Street,” started researching and trading stocks—that became my passion, and later I worked on Wall Street. Don’t get stuck because you don’t have the answer; many people find their perfect fit in their 30s or 40s. Give yourself more “shot opportunities,” and annually reflect: “Is this what I want to do for the rest of my life? Will I still want to do this in 30 years?” If the answer is “no,” then it’s time to explore other paths. Jeff Bezos’ “minimize regrets” framework is similar—imagine what advice your 80-year-old self would give about your current career choice. Our survey shows that if we could start over, 6 out of 10 would choose different careers. Many make wrong choices because they listened to professors’ praise or their parents’ advice for financial stability, instead of asking what they truly love.

Host: Can you list some jobs that can resist AI’s impact and those that are about to be eliminated?

Bill: The first to be threatened are language-related jobs, like translation and paralegals, because large language models are very good at reorganizing text. Also, if your work involves repetitive coding, demand will decrease, since code is essentially a language with stricter constraints than natural language. But if you understand how to evaluate why one algorithm is better structurally, or how to streamline code for efficiency, those skills will still be valuable. Still, I’ll reiterate: the best way to be a good software engineer in the AI world is to become someone who knows how all the new AI tools work. Be the one in your organization who actively embraces them rather than resists.

Jobs that can resist AI are those that can be called “craftsman’s jobs,” because they deeply understand the subtle nuances of their field—something AI is not good at handling. Additionally, interpersonal relationships will become even more important. Do you have a strong peer network? Do you have strong mentors? Do you have a robust relationship network? I believe this will be very helpful.

Host: What should ordinary people do now to elevate their AI tools to a new level?

Bill: The most important thing is to try various mainstream models like ChatGPT, Claude, Gemini, etc., and let AI handle more agentic tasks. For example, before a podcast interview, I ask AI to predict what questions the host might ask; or when preparing a TED talk, I use AI to research, prototype, and brainstorm ideas simultaneously. Many people don’t realize how much they can rely on AI. When I gave a speech at NYU, I found that half of the questions students asked could have been directly answered by ChatGPT. Now, for any information query, asking AI is much easier than searching Wikipedia.

Host: How can one find mentors and build a valuable peer network?

Bill: Regarding mentors, most people set their goals too high—trying to find those who are unlikely to respond. I suggest two strategies. First, build a list of potential mentors. Use free online resources (podcasts, interviews, AI queries) to research people you admire, like collecting digital fan profiles. This not only boosts your confidence but also tests whether you’re truly passionate about the field. Second, seek out slightly lower-tier individuals as actual mentors. If they’ve never been asked before, they’ll be pleasantly surprised. Don’t ask “Will you be my mentor?” right away; instead, make specific small requests, like “I’m exploring two paths, and I know you’ve considered both. Do you have any advice?” Or you can create an AI project using personal data and treat it as a virtual mentor for conversations.

For peer networks, aim to find 4 to 6 like-minded people at a similar career stage (preferably outside your organization), and create a WhatsApp or Slack group. Share ideas, expand your learning, and broaden your network. When you have a bad day at work or feel uncertain whether the problem lies with the industry or your current company, this group can help clarify your direction.

Host: How should parents educate children in today’s era? Are cramming classes still useful?

Bill: North America now faces a serious “resume competition.” Parents start worrying about college applications as early as sixth grade, filling children’s schedules with chess, hockey, even volunteering at animal shelters. While teaching perseverance is good, I worry children will be exhausted by the end of college. If they never have time to pause, explore, and discover what they truly want to do, that’s problematic. Universities now require early declaration of majors, which limits exploration. I suggest parents create as many opportunities as possible for children to explore different things and help them find their genuine interests.

Host: For those doing work they dislike but afraid to switch, what’s one thing they can do immediately this week?

Bill: You can run scenario simulations in the digital world about new paths. Set a scenario: “I plan to leave in six months,” and use AI tools to rehearse.

For example, ask AI: “I want to switch to this field in six months. What should I do in my first week?” It will give you a plan. You don’t have to follow it exactly, but this scenario planning can help you overcome hesitation. Do this for three different directions, updating with new data weekly. Once the details are filled in, it’s no longer an abstract idea—you’ll start to see which path you’re more inclined toward.

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