The thing to do right now is to run as fast as you can.
This is Bill Gurley, the legend who backed Uber and Zillow, who's lived through every major tech cycle for over 25 years. And he says this one is different.
There is so much disruption coming from this new technology that if you don't take control of your own career path, you're likely at risk. We did a survey where we asked people if you could go back in time and start your career over again, would you do something different? And six out of 10 said yes.
Before AI, the wrong career choice cost you years. With AI, the cost becomes colossal. We have this window of opportunity that's closing. So, we should be working really, really hard right now to grasp this opportunity.
How much time do we have?
I would warn all of your listeners that...
Bill, welcome to Silicon Valley Girl.
Thanks for having me on. Greatly appreciate it.
Thank you. I had a question planned, but there's news that just came out.
Block, the parent company that Jack Dorsey is laying off nearly half of its staff in deliberate and bold embrace of AI.
Well, I'm going to say yes, but I'm going to qualify it a little bit. The AI tools are out there. They've been out there for two or three years now. They're not going to be put back in the box. They're not going to go away. My advice, which is very straightforward for anyone in any field, to protect yourself against AI, be the most AI-enabled version of yourself possible and know what it's capable of in your field. Know the edge of what it's capable of in your field. Use it as much as you possibly can because one thing I've learned just in my own endeavors is that the types of prompts that you think of giving it increase the more you use it. You start to understand what it's capable of and so any lack of leaning into it means you're getting further behind against people that are. It's new in that it's hitting white collar workers, which I think people had viewed those jobs as safe, which may have been a mistake. And look, if you've been replaced, I would really, and this gets into this new book I'm releasing, I would ask yourself, is that the role you really loved and wanted to be in? And if not, maybe this is an opportunity for you to go find that.
Okay. So, yeah, we're going to see a lot of this type of news. You said that playing it safe, and you mentioned safe jobs. We considered them safe. We thought intelligence is something that's going to get us through life. You say safe is now the highest risk move. Can you explain?
I think the unfortunate reality is that many advisers and counselors and parents push people towards jobs that they thought of as safe. And the reason I say it's unfortunate isn't because of AI. If you're unfulfilled at work, there's a 2023 Gallup poll study that came out and said over 50% of people aren't actively engaged at work. And the number that qualifies engaged is like 23%. So if you're in these roles you don't really care that much about and you're not pushing yourself to improve, you're kind of a sitting duck anyway for these things. And I personally believe that all those parents were quite well-intentioned and very worried about the economic stability and viability of their children's lives. But the truth of the matter is you only get one shot at this life. If you can find something that you're just insanely curious about, you're going to differentiate yourself so much greater than everyone that's around you. I think in many aspects of life, the economic part comes along if you're really great at what you do.
Can you give me three traits of a person who doesn't play it safe? What do they do daily?
Well, first of all, I think the number one reason I wrote this book was to give permission. Give people permission to chase a job they might not have thought was either possible or that they might have thought someone would try and talk them out of. And there's examples in the book of that. Danny Meyer, who's a famous restaurateur in New York and the man that started Shake Shack, his uncle told him, 'You should go be a restaurateur.' But he was on a path, poli-sci major, salesman, taking the LSAT, gonna go be a lawyer. And his father had had some problems with economic trouble in businesses related to restaurants and it pushed him away from it. His uncle is the one that kind of brought him back. But his uncle told him, you know, all you do all weekend long is search for the best restaurants and he even journaled. Apparently since he was a kid, he journaled about restaurants, but he had never given himself the permission to think of it as a career and go after it. And the reason you're more protected is if you adore something, you're just constantly learning for free.
Like you're not spending. The second principle in the book is hone your craft. And I talk about continuous learning. And many people I think unfortunately learn in school and they think, 'Oh, I'm done now. I'll go work.' But the best are just always learning about what they do. And for the best that are hyper curious about that subject area, they gain energy in absorbing that new information. Whereas if you're forced to go to a class on something you don't like, you lose energy. It feels tedious.
Which is a great test as to whether you're tilting against the right thing or not.
So basically, don't listen to everyone around you.
I mean, there's extreme forms of this. I got to meet Rick Rubin. He said every single career decision he's made in his life, people around him told him not to do it and they were all the best decisions he possibly made. I mean, you can take that to an extreme, right? Like don't just go on quixotic pursuits. But I think if you become 100% convinced that you want to go try something and I have a test in here for whether you're really passionate at that level, then yeah, I think you should go try. And I think you'll find you're more successful and more fulfilled.
And I like the continuous free learning. So you're learning not because you're required to, but because it's your passion, you're...
curious about. And you've met people I know that are like that. I think everyone's met people that are like that. Silicon Valley's full of a lot of people like that, especially about new technologies. So, you know, you read an article about Claude and you just can't not, you know, boot one up and try and figure out what it does. And if you're that type of person, you're in the right lane. Like you're so fascinated by the subject that you have to know what's on the edge.
And by the way, it's interesting to think about the edge as a place that's safe from AI. So AI and large language models are recording like all the best practices that have been written down, but the stuff that's on the edge that's being discovered today is not in the models. And so if you're competing by being a person who has that knowledge in any field that hasn't been written down yet, you're out in front of what these models are capable of.
Yeah. And three, try new things. Yes. I feel like...
Yeah. We talk about AI tools constantly, but honestly, most of us don't feel the real value until we see it applied to something very, very specific that changes everything. Something we actually do every day. So, let's talk about outreach. If you're a creator, you need brand deals. If you're in sales, you need leads. If you're a founder, you need investors, partners, customers. And right now, done properly, LinkedIn outreach takes 10 to 15 hours a week. Every single week. This is exactly where AI changes the math. And Linked Helper is the concrete example I want to show you. Most tools are cloud-based. LinkedIn flags them very fast. This one is desktop native. It runs through a real browser, mimics actual human behavior. That's the only way to scale this safely in 2026. But what I find the most interesting is what happens when you connect it to an AI layer and Claude, and instead of sending the same message to 500 people, it reads each person's bio, writes something specific to them. That level of personalization at scale wasn't physically possible a year ago. $825 per month, you get scaled outreach. And instead of your team spending 10 hours a week on manual clicking, they're spending it on work that actually moves the needle and requires creativity. This is exactly what Bill was talking about. AI as a jetpack, not a replacement. You still build the relationships. You just don't waste the hours getting to them. Setup guide and templates are in the description with the free trial available. All right, let's get back to the interview with Bill. Since you've been investing for a while, I know you recently stopped, but...
What would Benchmark VC consider not playing it safe when looking at a founder?
Well, actually, I think that the venture industry at large has learned that you would never have a mindset of safety around choosing a founder. I think the best and the brightest are very independently minded. They think outside of the box naturally. I think if anyone feels... some of them are so dogmatically determined that they might come across as a bit, you know, crazy actually. And I think I'm not the only one that would say this. I think if you go study what venture capitalists have written, there's almost a search for that type of persona. And it goes back to like the Steve Jobs ad about the crazy ones. You know...
It feels like everyone right now should be adopting this crazy mindset to succeed in this world because you're becoming the entrepreneur in your life, right?
Yeah. That's a great way of saying it. There is, especially in certain fields, so much disruption coming from this new technology that if you don't take control of your own career path, then you're likely at risk. And I've often said if you're high agency, if you're a high agency individual who has confidence about driving their own career path, these tools are actually a jetpack. Like if you want to proactively learn, there's been no time in the history of the world where you can learn faster. And you know, it's AI, but it's also podcasts like the stuff you do. There's interviews all over YouTube. Like you can learn faster than ever before. But if you're... This is part of why I react poorly to the AI anxiety because that might freeze you and then you're not... like the thing to do right now is to run as fast as you can.
Yeah. But I also wanted to dig deeper into anxiety because you said something that gives me a lot of anxiety. Sometimes I scroll and I hear people including you say we have this window of opportunity that's closing so we should be working really, really hard right now to grasp this opportunity. Can you elaborate on that? How much time do we have? How much should we be working?
Well, I don't think the window's necessarily closing. I just think that this tool kind of came at us so fast and it's capable of so many different things that it really behooves any individual to figure out what it's capable of in their industry, in their role, and once again to be the person in the organization who knows the most about that and what's possible.
But do you think we might only have like a couple years?
I don't believe in... I'm not a big fan of these dystopian narratives. There's some interesting research you could go look up that this dystopian anxiety is like five times higher in the US than in China.
Yeah. I think part of the problem, and I don't fully understand the motivation, but some of... like Dario is the biggest doomer of all and he's got the microphone all the time.
And it's kind of weird and I don't think it's healthy for all the reasons we already discussed. Yeah. So, I wish that weren't happening.
But maybe also sometimes when I see those headlines, I'm like, maybe I should double down, work more, why it's also... it has a positive angle to it, right?
It could spur people into action. It could, but it also could freeze them, which we already discussed.
Totally. And something else that you said that unlearning what made you successful before is really important. How do you... So, for me, for example, I'm a very hardworking person. I would say yes to every brand deal because I'm used to it. And I realized that probably, but I'm not sure. Probably the next stage of my growth will happen when I learn how to say no.
How do you decide and how do you actually do it? How do you unlearn?
There's a great quote, 'Strong opinions loosely held.' And I really love that idea. So if you don't have strong opinions, it's very difficult to actually get out there and run every day and accomplish things. But don't view any of them as sacred. Like don't think of anything as hard and fast and might never change. And I think if you develop the habit of being a continuous learner and know that there's a risk of this thing, then you're probably best prepared to know when to let go of something. I know that may not be definitive, but I think awareness that it could be a problem is probably the most helpful thing possible.
Yeah. So when you start noticing it's actually in your way.
So in your book you talked about six principles, chase your curiosity. And this is where I've paused because I'm like okay I'm curious about so many things. There's this hype and that hype. I want to study this and do this. How do you pick out curiosity that then you can push for for years and it becomes your career?
Yeah, there's a whole bunch in that chapter that you mentioned, chase your curiosity. I went out and studied all the best practices in the field and there's like 10 different exercises you can run to try that I've borrowed from these other great people that have done the research. You know, hobbies are a big one. There's a lot of stories in the book of people that turned hobbies into careers and became very successful. Like if there's this thing that you're doing in your spare time at home. When I was an engineer for two and a half years, I read this book, One Up on Wall Street by Peter Lynch, and I started studying stocks and trading stocks when I got home at night. I didn't say to myself, 'Oh, maybe that's a sign,' but it was, right? And I ended up going to work on Wall Street. Like, and so look out for whatever it is that fascinates you. Don't feel stuck or don't feel like you have to have an answer to the question. Some of these people didn't find their perfect fit until they're 30 or 40. And so get as many shots on goal. Like it's fine to take a job where you don't know if that's it. But ask, wake up and ask yourself every year or so, is this it? Is this what I want to do the rest of my life? I had a mental exercise that I did in my first two stops in my career where I at a couple years in I said, do I see myself doing this 30 years from now and how do I feel about that? Just a kind of a reflection and in the first two cases I got to a place where I immediately knew the answer was no.
