Silicon Valley Girl$8B Investor: The Only Career Move AI Can't Replace | Bill Gurley
EVERY SPOKEN WORD
35 min read · 6,797 words- 0:00 – 2:32
Intro: Bill Gurley
- BGBill Gurley
The thing to do right now is to run as fast as you can.
- MMMarina Mogilko
[instrumental music] This is Bill Gurley, the legend who backed Uber and Zillow, who's lived through every major tech cycle for over twenty-five years, and he says this one is different.
- BGBill Gurley
So there is a 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 ten said yes.
- MMMarina Mogilko
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?
- BGBill Gurley
Like, I would warn all of your listeners that-
- MMMarina Mogilko
Bill, welcome to Silicon Valley Girl.
- BGBill Gurley
Thanks for having me on. Greatly appreciate it.
- MMMarina Mogilko
Thank you. I had a question planned, but there's news, uh, that just came out.
- BGBill Gurley
Oh, no.
- MMMarina Mogilko
Block, the parent company-
- BGBill Gurley
Yeah, I saw that
- MMMarina Mogilko
... of Jack Dorsey is laying off nearly half of its staff in deliberate and bold embrace of AI.
- BGBill Gurley
Yeah.
- MMMarina Mogilko
Should people be scared?
- BGBill Gurley
Well, I'm gonna say yes, but I'm gonna qualify it a little bit. And the AI tools are out there, they've been out there for two or three years now. They're not gonna be put back in the box. They're not gonna 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.
- MMMarina Mogilko
Okay.
- BGBill Gurley
And, and know what it's possible of in your field. Know the edge of what it's possible of in your field. Um, use it as much as you possibly can, 'cause one thing I've learned just in my own endeavors, the, the types of prompts that you think of giving it increase the more you use it. Like, 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, that, that, that are. It's new in that it's hitting white-collar workers, which I think people had viewed those jobs as safe, um, which m-may have been a mistake. And, and look, if, if you've been replaced, I would really... and this gets into this new book I'm [laughs] 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.
- MMMarina Mogilko
Okay. So yeah, we're gonna see a lot of this type of news. You said that playing it safe,
- 2:32 – 3:54
Why "Safe" Career Advice Is Dangerous
- MMMarina Mogilko
and you mentioned safe jobs, we considered them safe. We thought intelligence is something that's gonna, uh, get us through our life. Um, you say safe is now the highest risk move. Can you explain?
- BGBill Gurley
I think the unfortunate reality is that many advisors 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 twenty twenty-three Gallup poll study that came out and said over fifty percent of people aren't actively engaged at work, and the number that qualifies engaged is, like, twenty-three percent.
- MMMarina Mogilko
Mm.
- BGBill Gurley
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, like, for these things. And I personally believe that all those parents were quite well-intentioned a-and very, um, 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 gonna differentiate yourself m- so much greater than everyone that's around you. I think in many aspects of life, um, the, the economic part comes along if you're really great at what you do.
- MMMarina Mogilko
Can you, can you give me three traits of a person who doesn't play it safe? What do they
- 3:54 – 11:21
3 Traits of People Who Don't Play Safe
- MMMarina Mogilko
do daily?
- BGBill Gurley
Well, first of all, I think having... One of the... I think the k- 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. Um, Danny Meyer, who's a famous restaurateur in New York and the, the man that started Shake Shack, um, 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. And his uncle is the one that kinda brought him back. Um, 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.
- MMMarina Mogilko
Yeah.
- BGBill Gurley
Like, you're not spending... Like, the, 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, there's-- 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.
- MMMarina Mogilko
Yeah.
- BGBill Gurley
Which is a great test as to whether you're tilting against the, the wrong, the right thing or not.
- MMMarina Mogilko
So basically, don't listen to everyone around you? Uh-
- BGBill Gurley
I mean, there's extreme forms of this. I, 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 decision he possibly... [laughs] I mean, you can take that to an extreme, right?
- MMMarina Mogilko
Yeah.
- BGBill Gurley
Like, don't just go, you know, on quixotic pursuits. But I think if you become a hundred percent convinced that you want to go try something, and, and I have tests in here for whether you're really passionate at that level, um, then yeah, I think you should go try. Like, and I think, I think you'll find you're more successful and more fulfilled.
- MMMarina Mogilko
And I like the continuous free learning. So you're learning not because you're required to, but because it's your passion and you're spending-
- BGBill Gurley
And you're curious about it.
- MMMarina Mogilko
Yeah. And you can't stop yourself.
- BGBill Gurley
Yes. 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, uh, especially about new technology. So, you know, you read an article about Clawbot, and you just can't not-
- MMMarina Mogilko
Yeah
- BGBill Gurley
... you know, boot one and try and figure out what it does. And, and i- if you're that type of person, you're in the right lane.
- MMMarina Mogilko
Mm-hmm.
- BGBill Gurley
Like, like you're so fascinated by the subject that you have to know what's on the edge.
- MMMarina Mogilko
Yeah.
- BGBill Gurley
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, that's being discovered today is not in the models.
- MMMarina Mogilko
It's not, yeah.
- BGBill Gurley
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, you're out in front of what these models are capable of.
- MMMarina Mogilko
Yeah. And through trying new things-
- BGBill Gurley
Yes
- MMMarina Mogilko
... I feel like.
- BGBill Gurley
Yeah.
- MMMarina Mogilko
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, an NN 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. $8.25 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 jet pack, 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-
- BGBill Gurley
Yes
- MMMarina Mogilko
... I know you recently stopped, but what benchmark VC will consider not playing it safe when looking at a founder?
- BGBill Gurley
Well, actually, I think that the venture industry writ large has l- has learned that, that you would never, um, have a, a mindset of safety around choosing a founder.
- 11:21 – 12:58
How to Handle AI Career Anxiety
- MMMarina Mogilko
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-
- BGBill Gurley
Yeah
- MMMarina Mogilko
... to grasp this opportunity." Can you elaborate on that, how much time we have, how much should we be working? [chuckles]
- BGBill Gurley
Yeah. Well, I don't think, I don't think the window's necessarily closing. I just think that this tool kinda came at us so fast, and it's capable of so many different things that it's, it really behooves any individual to figure out what it's capable of in their industry and their role and, and once again to be the person in the organization who knows the most about that-
- MMMarina Mogilko
Mm-hmm
- BGBill Gurley
... and what's possible.
- MMMarina Mogilko
But do you think we might only have, like, a couple years-
- BGBill Gurley
No, I, I don't believe in the-
- MMMarina Mogilko
... before AGI or-
- BGBill Gurley
No.
- MMMarina Mogilko
No? Okay.
- BGBill Gurley
I, I... I'm, I'm not a big fan of these dystopian narratives. There's some interesting research you could go look up that the, the, uh, the anxie- this dystopian anxiety is, like, five times higher in the US than in China.
- MMMarina Mogilko
Oh, really?
- BGBill Gurley
Yeah. And I think part of the problem, and I, I don't fully understand the motivation, but some of... Like, Dario's the biggest doomer of all, and he's got the microphone all the time.
- MMMarina Mogilko
Yeah. He's-
- BGBill Gurley
And it's kind of weird
- MMMarina Mogilko
... always trending.
- BGBill Gurley
And I don't think it's healthy for all the reasons we already discussed.
- MMMarina Mogilko
Yeah.
- BGBill Gurley
So I wish, I wish, I wish that weren't happening.
- MMMarina Mogilko
But maybe also sometimes when I see those headlines, I'm like, "Maybe I should double down and work more." Why not?
- BGBill Gurley
Yeah. Yeah.
- MMMarina Mogilko
Like, it's also... It has a positive angle to it, right?
- BGBill Gurley
Yes. It c- it could. It could spur people into action.
- MMMarina Mogilko
Yeah.
- BGBill Gurley
It could. But, but, but it also could freeze them, which, which we already discussed.
- MMMarina Mogilko
Totally. Totally. And something also that you, you said, that unlearning what made you
- 12:58 – 14:07
Unlearning What Made You Successful
- MMMarina Mogilko
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-
- BGBill Gurley
[laughs]
- MMMarina Mogilko
... I'm used to it.
- BGBill Gurley
Yeah.
- MMMarina Mogilko
And I've realized that probably, but I'm not sure, probably the next stage of my growth will happen when I learn how to say no.
- BGBill Gurley
Yeah.
- MMMarina Mogilko
How do you decide, and how do you actually do it? How do you unlearn?
- BGBill Gurley
There's a great quote, uh, "Strong opinions loosely held," and I, I really love that, that idea.
- MMMarina Mogilko
Mm-hmm.
- BGBill Gurley
So if you don't have strong opinions, it's very difficult to actually get out there and run every day and, and accomplish things. But don't, 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, you probably are best prepared to know when to let go of something. I know that may, may not be definitive, but, like, I think, I think r- awareness that it could be a problem is probably the most helpful thing possible.
- MMMarina Mogilko
Yeah, so when you start noticing it's actually in your way.
- BGBill Gurley
Yeah.
- MMMarina Mogilko
So in
- 14:07 – 17:45
10 Exercises to Discover Your Real Curiosity
- MMMarina Mogilko
your book, uh, you talked about six principles. Uh, chase your curiosity, and this is where I've paused because I'm like, "Okay, I'm curious about so many things."
- BGBill Gurley
[laughs]
- MMMarina Mogilko
There's this hype and that hype. I want to study this and the this.
- BGBill Gurley
Yeah.
- MMMarina Mogilko
How do you pick out curiosity that, that you can push for for years and it becomes your career?
- BGBill Gurley
Yeah. There's a whole bunch. That chapter that you mentioned, Chase Your Curiosity, I, I went out and studied all the best practices in the field, and there's like 10 different-
- MMMarina Mogilko
Mm-hmm
- BGBill Gurley
... exercises you can run to try ... That I've borrowed from these other great people that have done the research. Um, you know, hobbies are a big one. There's a lot of stories in the book of people that turn hobbies into careers and became very successful.
- MMMarina Mogilko
Yeah.
- BGBill Gurley
Like, if there's this thing that you're doing in your spare time at home. When I was an engineer for, for two and a half years, um, 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. A- a- and 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.
- MMMarina Mogilko
Mm.
- BGBill Gurley
Like, and so look, look out for, for whatever it is that fascinates you. Um, don't feel stuck, like, or don't feel like you have to have an answer to the question. Some of these people, um, 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 and... but ask... wake up and ask yourself every year or so, "Is this it? Is this what I wanna 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, at, a couple years in, I said, "Do I see myself doing this 30 years from now, and how do I feel about that?"
- MMMarina Mogilko
Mm-hmm.
- BGBill Gurley
Just a kind of a reflection.
- MMMarina Mogilko
Yeah.
- BGBill Gurley
And in the first two cases, I got to a place where I immediately knew the answer was no.
- MMMarina Mogilko
Mm. I love that question.
- BGBill Gurley
And then, and then you start looking for something else. Bezos had a similar thing he called the regret minimization framework, where he said imagine your 80-year-old self giving you advice on helping with a, a career choice.
- MMMarina Mogilko
Yeah.
- BGBill Gurley
And they're similar in some ways. You're just reflecting over time.
- MMMarina Mogilko
Yeah. And when you studied those people who are not happy with their jobs, apparently it's six out of 10, right?
- BGBill Gurley
Yeah.
- MMMarina Mogilko
What do you think was the number one mistake that they made? Were they chasing money? I also write a newsletter where I go deeper on AI tools that I use, career strategies, and things I can't fit into a 60-minute podcast. It's free. Link is in the description.
- BGBill Gurley
I think so. I mean, chasing money or, or just doing... Like, like, we, we actually, 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. And then we would ask them, "What did you use in the decision-making?" And, you know, it might be you're at college and a professor tells you, "Oh, you should go into this," 'cause you made an A on a accounting exam or something. Or, or your parents. There's certain cultures where a parent's like, "You gotta be a doctor. You gotta be a lawyer," and you end up in that path.
- MMMarina Mogilko
Yeah.
- BGBill Gurley
Like, there's a bunch of different ways you could end up in a pathway where it wasn't an exercise of you saying, "What is it that I would love to spend my life doing?"
- MMMarina Mogilko
Yeah.
- BGBill Gurley
And so i- i- it is a whole... I think many of these parents and counselors are very well-intentioned. I don't think they're out to, to make a mistake. A lot of them are worried about the economic stability of the child. If you-
- MMMarina Mogilko
100%
- BGBill Gurley
... as you become a parent, like, it's this n- thing that you can't really get out of your head.
- 17:45 – 20:20
AI-Proof vs. AI-Vulnerable Jobs
- MMMarina Mogilko
and top three jobs that won't make it?
- BGBill Gurley
Well, the jobs that, that seem to me the earliest, uh, threats are ones where... So the large language model is really good at language, and so translation, paralegals, like these-
- MMMarina Mogilko
You know I started with language. [laughs]
- BGBill Gurley
[laughs]
- MMMarina Mogilko
That's, that was my whole career.
- BGBill Gurley
Yeah. I mean, those things-
- MMMarina Mogilko
Yeah
- BGBill Gurley
... are, are really-
- MMMarina Mogilko
Mm-hmm
- BGBill Gurley
... you know, we're just organizing text in a different way. Um, tha- those are, th- those are already... It's already happening.
- MMMarina Mogilko
Yeah.
- BGBill Gurley
You know, I think some of the jobs that... I have this interesting theory where almost any job, you could think of it as being an artisan. We all think of Michelangelo as an artisan, and we probably think of a great athlete as an artisan. But do you think of a lawyer that way, or do you think of... And I would say the best in those fields-
- MMMarina Mogilko
The best are. Yeah
- BGBill Gurley
... probably, probably are.
- MMMarina Mogilko
Mm-hmm.
- BGBill Gurley
And so what is it they do? Um, they understand nuance in their field quite a bit, and I think AI is not particularly good at nuance. Um, a lot of people have a theory that, that I think is reasonable that, that human relationships will matter way more. So do you have a strong peer network? Do you have a strong mentor network? Do you have a strong network in general of people who come to you or know you or what you're capable of? Um, that m- that, I think that's super helpful.
- MMMarina Mogilko
Any other markets that you think are dying?
- BGBill Gurley
Um, dying. Um, well, I mean, coding is one where there's a lot of questions that are out there, and I think once again, you know, the thing about code is it's actually a stricter, more constrained version of language than language itself.
- MMMarina Mogilko
Mm.
- BGBill Gurley
Right? The-
- MMMarina Mogilko
So do you think we'll need less coders?
- BGBill Gurley
Certainly if you were the person who was just grinding writing out code, if you were the person that understood, you know, structurally how one algorithm's better than the other or how to reduce code to make something more efficient, like those things I think will still be valuable. W- but I would go back to saying the best way to be a software engineer in AI world is to be the one that knows how all the new AI tools work.
- MMMarina Mogilko
Yeah.
- BGBill Gurley
Like to be the person in your org that's leaning into them, not out. Like you're... Y- if you're a farmer with a tractor and a drone thing and all this stuff, you're gonna run over a farmer with a hoe and a, and a donkey, right?
- MMMarina Mogilko
Totally.
- BGBill Gurley
You're just gonna blow them away, and so you have to think that way about these tools. This one came at us fast, I admit. Um, but you have to, you have to roll around in it.
- MMMarina Mogilko
Uh, let's talk about the tools. You said at the beginning of our podcast, become the best AI-enabled
- 20:20 – 22:35
Bill's AI Toolkit
- MMMarina Mogilko
version of yourself.
- BGBill Gurley
Yeah.
- MMMarina Mogilko
Can you talk about the setup? Because we're all, we're all using ChatGPT for search. Uh, we use Nana Banana to gen-generate images. We do basic stuff, right? We maybe plan our trips. What is the next step? What should people be doing to advance their setup?
- BGBill Gurley
Even like when I come on a podcast, I can say, "I'm gonna go see this person, do this podcast, and we're gonna talk about the book. What questions should I anticipate?" And it's like this is my p-- Like, the more you play with it, the more you think about what's possible to do. And, and I was, [laughs] I was at NYU yesterday and, and, uh, the students were asking questions at the end, and like half the questions they asked, I'd be like, "Well, you could ask me that, but I'd probably put that into ChatGPT." [laughs]
- MMMarina Mogilko
Mm.
- BGBill Gurley
Like, I just-
- MMMarina Mogilko
Yeah.
- BGBill Gurley
They don't think, like the-
- MMMarina Mogilko
Yeah
- BGBill Gurley
... people don't realize how much you can lean on it, and that's where I think the more you roll around on it, the more you start to use it. And I've been invited to, to go to give a TED Talk, so I have a new one on that. And I-
- MMMarina Mogilko
Oh, are you going to, to go in April?
- BGBill Gurley
To go to... Yeah.
- MMMarina Mogilko
I'll be there too.
- BGBill Gurley
Cool.
- MMMarina Mogilko
I'll, I'll watch your talk.
- BGBill Gurley
All right. [laughs] And, uh, and I'm like re- you can research and prototype and ideate like simultaneously. I came up with a new theme last night, kicked off something this morning 'cause I wanted it to find like twenty examples of this idea I had and wanted to talk about to, to make it better.
- MMMarina Mogilko
Mm-hmm.
- BGBill Gurley
And I haven't looked at the results yet, but I will later.
- MMMarina Mogilko
So, so you're basically living in, in Claude project? [laughs]
- BGBill Gurley
Yeah. I mean, I... Those were ChatGPT.
- MMMarina Mogilko
Oh, did you?
- BGBill Gurley
But yeah.
- MMMarina Mogilko
Mm-hmm.
- BGBill Gurley
But you could. Yeah. I mean, you're probably better to try them all.
- MMMarina Mogilko
Well, what is something that you do with AI now that you've done manually before and now you can never do it manually?
- BGBill Gurley
Almost any information query whatsoever, like it just seems easier than, than looking it up, and even like compared to a Wikipedia search or something, like you can just get straight to the information versus like scrolling through this thing.
- MMMarina Mogilko
Yeah.
- BGBill Gurley
I haven't set up a Claw bot yet or started getting it to do agentic work on my behalf. I probably should.
- MMMarina Mogilko
Mm.
- BGBill Gurley
Part of, uh, raising my hand and, and stepping away from VC is, is because I grew tired of like that constant FOMO that's required to be successful.
- 22:35 – 25:58
Is Software Dead? What to Build Now
- MMMarina Mogilko
uh, just in general for, for people who are building, since you are investing in them, do you think software is dead?
- BGBill Gurley
I don't.
- MMMarina Mogilko
Why?
- BGBill Gurley
Um, th- there are certain... And, and look, I think there are certain types of software that may be. If, once again, if, if all the software did was reorient text or, or, you know, create an image or whatever, like it could be under threat. The other thing is like, quite frankly, it's not really good at being a database, and it's not great at math yet, and there's new techniques where they're getting it to write code, but how many times have you done a query where there's an error? And de- once again, depending on the type of software, you wouldn't want it writing errors into your CRM.
- MMMarina Mogilko
Absolutely. Sometimes I think about the future where now I mostly talk to my Claude or Cha-ChatGPT. What if I just ask it to create an app for me to solve some particular problem, and I don't need to install any apps?
- BGBill Gurley
Yeah.
- MMMarina Mogilko
Think about consumer apps, right? I don't know, of like a fitness tracker-
- BGBill Gurley
Yeah, yeah
- MMMarina Mogilko
... language learning, right?
- BGBill Gurley
Yeah, yeah.
- MMMarina Mogilko
Exam prep. SAT was just released on Gemini. So I'm thinking like there's this whole market that's probably gonna disappear.
- BGBill Gurley
That could be true. That could be right.
- MMMarina Mogilko
So-
- BGBill Gurley
But that, but that's happened in the past. There used to be software companies that had massive market share that don't exist anymore.
- MMMarina Mogilko
Yeah.
- BGBill Gurley
So yeah.
- MMMarina Mogilko
How should entrepreneurs be thinking about what they're building?
- BGBill Gurley
Every great entrepreneur recognizes that new technology waves create a ton of opportunity, and one of the reasons Silicon Valley gets so excited when these waves happen, I mean, every single venture capitalist I'm sure that you talk to, all they wanna talk about is AI, right? They don't... I think they've forgotten about the companies they invested in that aren't AI. That's all they wanna talk about. And the reason they have so much attention to it is because the time when new companies, you know, step around and take market share for incumbents are on these transitions, and everyone knows it.
- MMMarina Mogilko
Mm-hmm.
- BGBill Gurley
And so I'm gonna sound so redundant, but you gotta get out there and play with it. Like the-
- MMMarina Mogilko
Yeah
- BGBill Gurley
... I would, I would warn, um, all of your listeners that it's very hard right now to raise venture capital for non-AI plays. I'd like to separate whether you're judging that from the reality. Go back to this circle of influence thing.
- MMMarina Mogilko
Mm-hmm.
- BGBill Gurley
It... The reality is most venture capitalists won't take a meeting with a non-AI company right now.Now you could decide I'm, I'm gonna do it any- I think complaining about that's useless-
- MMMarina Mogilko
Mm-hmm
- BGBill Gurley
... 'cause it is the reality. Um, you could decide, well, I'm g- it'd be a great time to bootstrap one of those companies 'cause VCs aren't paying attention. I think that's a reasonable re- you know, response to that.
- MMMarina Mogilko
Mm-hmm.
- BGBill Gurley
But you need to be aware of that.
- MMMarina Mogilko
Yeah.
- BGBill Gurley
Like, otherwise you're gonna get very disappointed when you go out and try and raise money.
- 25:58 – 30:25
How to Find Mentors?
- BGBill Gurley
I think most people, if you, if you're in, if you're in the mentor game, most people shoot too high, and they go try and get someone who's not gonna say yes to spend five minutes with them. And, and I, I, I would really caution against that type of activity, and I would instead do two different things. Take advantage of all this incredible free information that's out there, and build a list of what I would call aspirational mentors. So these are people you admire in your field, and just study 'em. Like, create a Google Doc, I don't care what, like, and, you know, find a podcast they're on, um, find books, find YouTube interviews, ask AI about 'em, and just build, like, a digital profile of each one of 'em, and be a fanboy the way someone might be of LeBron James, right?
- MMMarina Mogilko
Mm-hmm.
- BGBill Gurley
And I think that exercise will give you more confidence. It'll give you, um, you'll... It also tests whether this is the thing you're curious about or not. If that sounds tedious, what I just described, this, you're not in that-
- MMMarina Mogilko
No, I think it's, it sounds really exciting. I'm, that I'm thinking you can do this for your whole, like, dream career, right?
- BGBill Gurley
Yes.
- MMMarina Mogilko
Or you, like, I'm trying to be this. Here, here are the people that are already doing this. Here is, I don't know, whatever my dream house [laughs] or anything.
- BGBill Gurley
Yeah, no, Danny, Danny Meyer did this. Like, when he, when he decided he was gonna go be a restaurateur, he built these 10 profiles of these people. And, like, I think it, I think that exercise of ruminating in that is super helpful. It makes, gives you confidence that it, that it's achievable. It helps, it's disinhibiting, that this may be a tough way to go. And then on, on real mentors, just come down the ladder a couple rungs. If you're the first person that calls someone and asks them to be a mentor and no one else has asked them that before, they're gonna be flattered that you recognized who they were.
- MMMarina Mogilko
But how do you ask them? You're like reach out to them and say, like, "Hey, could you be my mentor?" Or you ask a specific question?
- BGBill Gurley
Uh, well, there's some nuance to that as well, so I wouldn't walk up to someone-
- MMMarina Mogilko
Yeah, because saying mentor is, like, too broad
- BGBill Gurley
... and say, "Will you be my mentor?"
- MMMarina Mogilko
Yeah. [laughs]
- BGBill Gurley
They're like, "Wow, that's a lot of weight." Yeah, I think you approach people with recognition of who they are and, and auth- this authenticity. I wouldn't be overly, like, programmed as you go in, and with a, with a smaller ask to start-
- MMMarina Mogilko
Mm-hmm
- BGBill Gurley
... the relationship. "Hey, I'm working on this problem. You know, there's these two paths. I'm sure you've thought about this before. Any advice on what I should do?"
- MMMarina Mogilko
Yeah. And, uh, when you mentioned that a lot of people ask you things they could ask ChatGPT, I'm thinking now-
- BGBill Gurley
Yes
- MMMarina Mogilko
... before asking people to become your mentor and ask, answer this question, create a project with all their knowledge base and ask that project [laughs] first.
- BGBill Gurley
You, you can, you can have a virtual mentor.
- MMMarina Mogilko
Exactly.
- BGBill Gurley
You could tell, tell AI to, uh, you could dump a book, dump an interview, dump a transcript-
- MMMarina Mogilko
Yeah
- BGBill Gurley
... and create a project around an individual, yes.
- MMMarina Mogilko
Yeah.
- BGBill Gurley
You could-
- MMMarina Mogilko
I do that a lot. AI is my strategic partner 100%.
- BGBill Gurley
[laughs]
- MMMarina Mogilko
Really, really helpful.
- BGBill Gurley
But I, let, let me also mention this, this separate chapter on peers, 'cause this is my favorite-
- MMMarina Mogilko
Mm
- 30:25 – 32:43
Future of The Education
- BGBill Gurley
Yes. Yeah.
- MMMarina Mogilko
This is a very interesting time, right? And I have two kids, a six-year-old and a four-year-old. I was raised, uh, by my Soviet parents-
- BGBill Gurley
Yes
- MMMarina Mogilko
... telling me you have to study, study, and study. That's the only way-
- BGBill Gurley
Yeah
- MMMarina Mogilko
... to grow. That's the only way to build a sustainable life. So I was studying from 8:30 AM to 8:30 PM.
- BGBill Gurley
Yeah.
- MMMarina Mogilko
Will this still apply?... in today's world to our kids, or should I be teaching them something completely different?
- BGBill Gurley
Well, I think the culture you came from is a little different than, than-
- MMMarina Mogilko
It is [laughs]
- BGBill Gurley
... which, which true here. Um, but I still think... I think the thing that's happened in North America, which is a version of that, is it's become so hard to get into universities here that starting in the sixth grade, parents are worried about... Uh, Jonathan Haidt calls it the resume arms race. You're worried about them getting into college, so you want your child-
- MMMarina Mogilko
I'm worried now. Not sixth grade.
- BGBill Gurley
Yeah, yeah. [laughs]
- MMMarina Mogilko
Now. Four-year-old, I'm worried.
- BGBill Gurley
They say start worrying about the college application in... Here, here it's the... I think it might be better if they just studied 12 hours instead. Here, you add in chess lessons, lacrosse lessons, like volunteering at the SPCA. You're like d- And these kids are so scheduled.
- MMMarina Mogilko
Mm-hmm.
- BGBill Gurley
Like... And I, I... What I fear is that they get to the end of the college and they're just burned out, like because they've been to- Angela Duckworth says they've been taught to persevere, like, like we've trained them.
- MMMarina Mogilko
Isn't it good?
- BGBill Gurley
Um, the area where it might not be good is that they never take a breath to explore and figure out what they wanna do.
- MMMarina Mogilko
Mm-hmm.
- BGBill Gurley
It used to be in the US college system, they wouldn't allow you to pick a major until the end of your sophomore year. Now, at many schools, you have to apply to the major as part of the application process.
- MMMarina Mogilko
Mm-hmm.
- BGBill Gurley
And so we're, we're asking people to specialize early and earlier, and then maybe they never had a chance to really figure out what it is they enjoy. And they might have fallen into one of those pathways for random reasons like we talked about before.
- MMMarina Mogilko
So what would be your advice to modern parents?
- BGBill Gurley
Take a deep, deep breath-
- MMMarina Mogilko
Mm-hmm
- BGBill Gurley
... and create as much opportunity for exploration as possible-
- MMMarina Mogilko
Mm
- BGBill Gurley
... for the kids. Just expose them to a lot of different things, and try and get a sense of genuine interest on their part.
- MMMarina Mogilko
Yeah.
- 32:43 – 34:30
Stuck in a Bad Job? Do This This Week
- MMMarina Mogilko
to make a move.
- BGBill Gurley
Yeah.
- MMMarina Mogilko
What is one thing they should do this week?
- BGBill Gurley
I think you can role play this new path you might go towards, and part of this I'm borrowing from a professor at Stanford, Dave Evans. He talks about like battle carding scenarios. So the same exercise we said where you could go study this person, you could say, "Okay, I'm gonna be, be out of here within six months" and create a digital like role play of, okay, I'm... What am I gonna go do? And you could do that for maybe three different directions, right?
- MMMarina Mogilko
Mm-hmm.
- BGBill Gurley
And roll around in it. Like scenario plan.
- MMMarina Mogilko
Hmm.
- BGBill Gurley
Right? What is, what is the first... Then once again, Cha- you know, an AI tool could help you do this. Say, "Okay, I would like to repot myself into this career within six months. What should the first week look like? What..." It'll give you something.
- MMMarina Mogilko
Love it, yeah.
- BGBill Gurley
It'll, it'll spit something out and, and you may disagree with that, you may reorganize it, but the thought process of going through what it might look like will help you e- versus just being frozen, right?
- MMMarina Mogilko
Yeah. And the power is coming back to it every single week with new data. Like, I tried this.
- BGBill Gurley
Yes.
- MMMarina Mogilko
Here's how it worked.
- BGBill Gurley
And if you did the battle card of like three different ones, you know, w- I think you'll start, as you s- fill in the details, you'll start to have-
- MMMarina Mogilko
Vision, yeah
- BGBill Gurley
... a sense of which one you prefer, whereas i- it may just be too abstract at the high level.
- MMMarina Mogilko
Thank you so much.
- BGBill Gurley
Yeah.
- MMMarina Mogilko
I think it was very useful and very practical, and I encour- I encourage everyone to read your book. Can we show it?
- BGBill Gurley
Runnin' Down a Dream.
- MMMarina Mogilko
Love it. I love the name.
- BGBill Gurley
Thank you so much for having me on.
- MMMarina Mogilko
Thank you so much. If you enjoyed this episode on the future of work, you're going to love my recent conversation with the CEO of LinkedIn. We went deep on the exact same topic. Link is right below. Check it out, and I'll see you in the next one
Episode duration: 34:30
Install uListen for AI-powered chat & search across the full episode — Get Full Transcript
Transcript of episode nBM3_AzNYU8
Get more out of YouTube videos.
High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.
Add to Chrome