The best skill for your career

Summary

Podcast Summary: This Is Working with Daniel Roth

Episode: The Best Skill for Your Career
Date: March 5, 2026
Host: Dan Roth (LinkedIn Editor-in-Chief)
Guest: Bill Gurley (General Partner, Benchmark Capital; Author, Running Down a Dream)

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Episode Overview

In this episode, Dan Roth sits down with iconic venture capitalist Bill Gurley to uncover the most essential skill for building a thriving, future-proof career. Drawing on his own experiences in Silicon Valley, insights from his new book, and lessons from legendary leaders, Gurley argues that continuous learning—driven by genuine fascination—is the skill that outpaces all others. The conversation ranges from tactical advice for early career professionals to big-picture reflections on reinvention and finding meaningful work at any stage.

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Key Discussion Points and Insights

1. Continuous Learning as the "Infinite Skill"

• Continuous Learning as Antidote to Obsolescence
  • “Continuous learning is the best way to protect yourself from any type of obsolescence. Be the person in your department that knows more about how AI is going to affect that role than anybody else.” (Bill Gurley, 00:00 & 04:29)
• Passion fuels sustainable learning.
  • Gurley emphasizes that fascination or "obsession" turns learning from a grind into a pleasure, enabling ongoing skill-building across an entire career, and not just when prompted by deadlines or fear.

2. The Importance of Alignment Between Passion and Career

• Success stories often involve obsessive learners.

  • The happiest and highest achievers are those who would “go home and learn about something that's going to make your job better the next day instead of watching a Netflix series.” (Bill Gurley, 02:19)

• Quote:

  • "It's imperative to get to a place where you adore what you're doing and then the learning's free." (Bill Gurley, 03:45)

• Gauge your path: If learning feels like a grind, you might be in the wrong lane.

3. Agency and Embracing New Skills (AI as a Case Study)

• It’s never been easier to learn; agency is the differentiator.

  • "If you're the type of person that's high agency who doesn't view a skill set as something fixed but something dynamic, then you're empowered." (Bill Gurley, 05:30)

• AI is both a challenge and a turbocharger.

  • Those who leverage AI become “even more powerful than I was. It's an interesting paradox with people who are like, AI is going to kill me.” (Bill Gurley, 05:30)
  • Roth likens AI to Ripley’s exoskeleton suit from Aliens, an augmenting superpower for the already skilled. (Sam, 05:57)

• Early specialization in trending skills (like TikTok or AI business applications) is a powerful differentiator, especially for young professionals. (Bill Gurley, 04:39 & 05:06)

4. Learning from Others: Mentors and Peer Groups

a) Mentorship (07:16 – 08:06)

• Aspirational mentors:

  • Don’t overreach at first—study high-profile figures from afar and take notes; “They can be mentors from afar. And slowly, over time, maybe they get to meet one of them. Imagine how prepared you are for that meeting.” (Bill Gurley, 06:29–07:16)

• Real mentors:

  • Seek role models just a rung or two above you. It's much more likely to succeed: “If you're the first person, the first time they've been asked to be a mentor, they're going to be flattered... 80 or 90% chance of getting a yes.” (Bill Gurley, 07:16)

• Notable anecdote:

  • Kobe Bryant, already an NBA superstar, sought out Hakeem Olajuwon to improve his footwork. (07:48)

b) Peer Groups (08:09 – 09:07)

• Forge supportive “learning peer groups.”
  • Find 4–8 peers outside your company, "on that same spot on the ladder," to “accelerate all the things we talk about—if four people are learning simultaneously and sharing ideas, you're learning faster than if you're learning by yourself." (Bill Gurley, 08:09–09:00)
  • Share networks for exponential career growth; embrace an infinite mindset.

5. Reinvention and “The Next Act” (09:07–11:50)

• It's never too late for reinvention.

  • Gurley shares his process of stepping back from active investing after reaching the summit of venture capital. He was inspired by Steve Martin's autobiography (Born Standing Up) and the story of leaving the stage at the right moment. (Bill Gurley, 09:41–10:32)

• On shifting to tackling larger societal problems:

  • Gurley is developing a new initiative, “P3,” aiming to address issues like regulatory capture, K–12 education, and US healthcare by applying his skills of "inspection, synthesis, and communication.” (Bill Gurley, 10:32–11:33)

6. How to Find Work You Can’t Ignore (11:50–12:26)

• Follow “the work you can't ignore”—even hobbies can become breakthrough careers.
  • Story of Tito, who founded America’s top vodka company at age 40 by pursuing his longstanding holiday hobby of making flavored vodka. (Bill Gurley, 11:50–12:26)

7. Rethinking Education and Encouraging Quixotic Pursuits (12:33–end)

• Gurley critiques the “conveyor belt” model of education.

  • Overprogramming kids leads to burnout and stifles creativity and fulfillment. Referencing Jonathan Haidt and Rick Rubin, he calls for more openness to risk-taking and experimentation.

• Final takeaway:

  • "I want them to believe in what's possible and I want to give people permission to go try something that may feel a little quixotic." (Bill Gurley, 12:33–end)

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Notable Quotes & Memorable Moments

• On learning and obsolescence:
  • “Learn to learn, then you're always pushing yourself to a new place.” (Bill Gurley, 00:57)
• On career happiness:
  • “Get to a place where you adore what you're doing and then the learning's free.” (Bill Gurley, 03:45)
• On AI’s impact:
  • “For high agency people that are honing their craft and know where they're running, AI is like jet fuel.” (Bill Gurley, 05:30)
• Mentorship advice:
  • “Just quit shooting so high. There's plenty of knowledge, you know, two rungs above you instead of eight rungs above you.” (Bill Gurley, 07:16)
• Steve Martin story:
  • “He looks up and for the first time the upper row's empty. He never went on stage again. And then he went on to do all the great acting. That was inspiring to me.” (Bill Gurley, 09:54)
• On overprogramming kids:
  • “As parents, we really worry about the economic stability of the individual, but you should probably be more worried about the life fulfillment of the individual.” (Bill Gurley, 12:33)

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Segment Timestamps

• 00:00–02:05: Why continuous learning is the top career skill
• 02:05–03:45: Fascination, side hustles, and joyful learning
• 03:45–05:06: Career alignment and standing out (AI, TikTok expertise)
• 05:06–06:29: AI as superpower and learning through teams
• 06:29–08:06: How to find and approach mentors
• 08:09–09:07: The value of peer learning groups
• 09:15–10:32: Gurley’s personal career transitions and inspiration from Steve Martin
• 10:32–11:50: New ventures: tackling regulatory capture, education, healthcare
• 11:50–12:26: Turning hobbies into careers; the Tito story
• 12:33–end: Gurley’s message—permission for risk and fulfillment, rethinking the education system

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Takeaways for Listeners

• Continuous, fascination-driven learning is the best way to future-proof your career.
• Invest in relationships with mentors and peers. Growth compounds when shared.
• Be bold in following work you can’t ignore—reinvention is possible at any age.
• Challenge conveyor-belt thinking in education and career paths—fulfillment is as vital as economic stability.

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This episode is a must-listen for anyone building, renovating, or reinventing their career. Bill Gurley’s blend of tactical wisdom, real-world anecdotes, and encouragement offers actionable guidance for navigating work, learning, and life.

Transcript

[Bill Gurley]

I think continuous learning is the best way to protect yourself from any type of obsolescence. Be the person in your department that knows more about how AI is going to affect that role than anybody else.

[Sam]

Welcome to this is working where leaders share their strategies for success and the lessons that shape them. As general partner at Benchmark Capital, Bill Gurley has made some of the most legendary bets in tech history. Think Uber, Zillow, Snapchat. But after decades at the top of the VC world, Bill is stepping back to answer a harder question. What does it actually mean to build a career you love? You'll find his answers in the new book Running down a dream. LinkedIn just came out with its skills on the rise. This is our look at the annual most in demand skills. The skills that are getting people hired. And what I hear from people all the time is how do I even know what skills I have? How do you think about this idea of figuring out what is it that you're good at and where you want to invest your time?

[Bill Gurley]

I think one of the the key points of this book here is to encourage people to have the gumption to go try and succeed at a career that is congruent with their passion, or there are better words like fascination or obsession. I think continuous learning is the best way to protect yourself from any type of obsolescence. And I think that it is very difficult to continuously learn if you don't have fascination because you it'll start to feel grindy. Yeah, There's a perception, especially in white collar jobs that, oh, I'm done with college, I'm done learning. Now I'm just going to go work. Right? And the best and the brightest in every field are constantly learning. There's a famous story about Satya Nadella's turnaround at Microsoft and he said he inherited a know it all culture and he told them they had to become a learn it all culture. And I think like that's kind of an infinite skill set. Like if you can learn to learn, then you're always pushing yourself to a new place.

[Sam]

Let's say someone is earlier in their career and they're like, God, I've got so much work to do. Just getting through the day is tough. And now I want to just go home and, you know, hang out. Bill Gurley is telling me that I basically have to put even more work in after I'm done with work.

[Bill Gurley]

I think the people once again that are in the right lane, it doesn't even feel like work. The book has a interesting structure. We've interleaved profiles which are stories of success with principles, which are more of the tools of success. And when you read these profiles, and I think this is true of everyone, you know, that's really great at what they do. The learning's free. Like, it's not a grind and it's actually the best test, I think. Would you go home and learn about something that's going to make your job better the next day instead of watching a Netflix series? And if not, there are people like that and you might be competing against somebody like that.

[Sam]

Yeah.

[Bill Gurley]

Angela Duckworth has this new phrase. She says, act like a paramecium, move towards warmth and nutrients, move towards something more exciting. There's an anecdote in here from the guys that run the acquired podcast where one of them would, no matter what job he had, would. Would beg the company to allow him to do a side hustle. And that way he got exposure to two jobs instead of one. And when he was at Microsoft, he launch Microsoft Garage as part of that. And when he got to Madrona, he said to him, do you mind if I start a podcast? And that ended up becoming his life, you know, work. I think he is so happy right now where he is.

[Sam]

They're crushing it.

[Bill Gurley]

I just think it's imperative to get to a place where you adore what you're doing and then the learning's free.

[Sam]

Did that happen to you early in your career?

[Bill Gurley]

It happened. Most inventors, you're scared to death that there's some apparent in the, in the top 10 in the app Store that you don't know about, like, like an intentional FOMO of sorts.

[Sam]

But in that case, it's not being scared. What, what you're describing is being scared, but then going all in. I think for a lot of people it would be, I'm scared and this sucks. And now my, like, stomach is, you know, turning into knots.

[Bill Gurley]

I probably shouldn't have used the word scared like, like, I just developed an instinct to not want there to be information I didn't have.

[Sam]

Yeah.

[Bill Gurley]

The very best way to protect yourself against obsolescence would be to be the person in your department that knows more about how AI is going to affect that role than anybody else.

[Sam]

Yep.

[Bill Gurley]

You're. You're not only going to be a survivor, you're going to be the one they're coming to asking for questions, and you're going to be rising. I'll give you a different example. If you're a young person trying to break in to any field, I guarantee you, if you had immense knowledge of how and why TikTok works. That would be interesting to the employer because the people that already live in that company don't really have any idea how it works.

[Sam]

When we look at our skills on the rise, the AI skills, not surprisingly, are dominating the list.

[Bill Gurley]

Which is, to my point, right?

[Sam]

That's exactly it. And there are two ones. There's the technical skills, which are like, how do you build, you know, large language models? Then there's the AI implementation skills, which are like AI business AI for design, data quality. And we're only a couple years into this. Like those are skills you can still get. You can be at the cutting edge of this today if you want to be.

[Bill Gurley]

There's no doubt it's never been easier to get information in the history of the world. And so if you're the type of person that's high agency who doesn't view a skill set as something fixed but something dynamic, then you're empowered. For high agency, people that are honing their craft and know where they're running, AI is like jet fuel. It's like I'm even more powerful than I was. And it's an interesting paradox with people who are like, AI is going to kill me.

[Sam]

Yeah. I think about it as the image in my mind is always the end of aliens. When Ripley has to put on this exoskeleton to find the alien, like she was already a great fighter, then the exoskeleton helped her. That's how I feel like AI is for people adds this superpower to you. You also talk in the book about learning from other people. Obviously, AI is this incredible superpower. It can do everything. But there is so much power in forming teams of like minded people who are finding a mentor who can work with you. Could you talk a little bit about why that's so important, how to go about doing it?

[Bill Gurley]

Yeah. Let's divide the two pieces. So I have a chapter called embrace your peers and I have a chapter on mentors, but let me do the mentors first. I think people always shoot too high. They have this idea that they're going to ask Satya Nadella to be their mentor and it doesn't work. And then you're like, oh, that's too hard. I really like this idea of aspirational mentors. Make a list of 5, 10 people that are the kind of person you can't get right now, but that you admire for what they're doing in your industry and then study them and every time you see them do A post or every time they do a podcast, like listen, like start to keep notes. They can be mentors from afar. And slowly, over time, maybe they get to meet one of them. And imagine how prepared you are for that meeting.

[Sam]

Right.

[Bill Gurley]

So that's aspirational. And then on real mentors, just dial it down a level or two. On the ladder rung, if you're the first person, the first time they've been asked to be a mentor, they're going to be flattered. You're going to have like a 80 or 90% chance of getting a yes. So just quit shooting so high. There's plenty of knowledge, you know, two rungs above you instead of eight rungs above you.

[Sam]

You have that great example of Kobe going to Akeem Olajuwon.

[Bill Gurley]

Is that who it was?

[Sam]

And asking for help. And Kobe had been in the, in the NBA for 13 years at this point.

[Bill Gurley]

Yeah. Kobe had won three or four rings and three or four MVPs of the league. And in the off season, called Akim Olajuwon and said he wanted to learn more about footwork in the post and flew to Houston and spent time with him. And Aim was flattered, by the way.

[Sam]

All right, so mentorship, you said. And the other one is sort of this.

[Bill Gurley]

The other one's called embrace your peers. And this is something that I feel not enough people recommend. So the idea is if you can find four to eight people that are on that same spot on the ladder, that first rung and have the same ambitions you do against this career. And I think it'd be ideal if they were outside your company, because the part of the point of this group is to accelerate all the things we talk about. If four people are learning simultaneously and sharing ideas, you're learning faster than if you're learning by yourself. If four or five people share the network they've built with each other, that network's getting a lot bigger, a lot faster. A lot of people are taught to be a little more sharp elbowed. And the truth of the matter is, in most fields, there are lots of winners.

[Sam]

Yeah.

[Bill Gurley]

And if you take more of an infinite mindset, like you're gonna, you're gonna get so much value out of doing this.

[Sam]

A lot of the book is focused on sort of people earlier in their career.

[Bill Gurley]

Yeah.

[Sam]

But you also talk about next acts and this idea of going on and doing something else.

[Bill Gurley]

Yeah.

[Sam]

That it's never too late. How do you think about your own next act?

[Bill Gurley]

Well, I'm 59, so I don't know how Many acts I have left. But the venture capital world was my dream job. I got to a point where I knew it was time for me to raise my hand and clear victory.

[Sam]

What was that point?

[Bill Gurley]

It was like three or four years ago. I decided I'm going to stop making new investments.

[Sam]

Was there something that happened in your life that you said it's time?

[Bill Gurley]

I hesitate to say it because it sounds outlandish, but I was watching David Letterman interview Jerry Seinfeld. They both start talking about this book by Steve Martin called Born Standing Up.

[Sam]

Great book.

[Bill Gurley]

I got it that night. By two days I had read the whole thing. Steve spent probably 15 years banging around before his standup act started to work. But he tells an anecdote in the book. He goes from stand up club to arenas and he's in Vegas one night and he looks up and for the first time the upper row's empty. He never went on stage again. And then he went on to do all the great acting. That was inspiring to me. I'd watched other venture capitalists maybe hang around the rim too long and I believe the industry tilts towards youth. So it was my time.

[Sam]

Wow. Okay, so you're feeling like the upper rows might start to be empty out, you're ready for your next act?

[Bill Gurley]

You know, I did this talk at the all in conference about regulatory capture that got 4 million views. So that's surprising you could talk about regulatory capture and get that much attention. And it made me think that I'd love to go tilt against some of the bigger problems in the country. I'm in the infant stages with it. It's going to be called P3. I've funded it and I'm going to partner with a lot of professors to do work. Regulatory capture is something I'm interested in. The US K through 12 school issue is something I'm interested in. The US healthcare system is a big problem. These are big meaty subjects and I don't know if I'll be able to help or not. But in my career I've done a of kind of inspection and synthesis and then communication and I think those skills could be helpful here.

[Sam]

People who are considering their next acts. Also there's a lot of people who are saying I'm not sure where my career is going or I'm not sure how to land another career. Is there advice that you would give them about how to find something? Is there advice that you came across while working on your book?

[Bill Gurley]

Do the work you can't ignore? Yeah, like, and maybe it's Your hobby, Like maybe a lot of people in here turned a hobby into a career. Yeah, you know Tito, the famous Austin beverage, you know, at 40 he had been a seismologist, he had been a mortgage broker. And his, his hobby on holidays was to make flavored vodka for people. People would call him the vodka guy. But he never considered it as a career until one day he did at 40 and he owns 100% of it and it's the most successful spirit company in the country.

[Sam]

It's incredible. If you wanted people to have like one takeaway from your book or a couple takeaways, what are you saying to them?

[Bill Gurley]

I think that our education system has evolved to a place where people feel like they're being run through a conveyor belt. It's become very competitive. It's hard to get into these colleges. And parents are starting to fill their kids schedule by the sixth grade with chess lessons and lacrosse lessons and all this stuff because they're very worried they're not going to get into the right college. The kids are over programmed. You know, Jonathan Haidt has a chapter in his in coddling called the decline of play. And Rick Rubin talks about this as well. He just feels like the creativity of the individual is lost because they're being pressured through this system and then when they get to the end, there's burnout. As parents, we really worry about the economic stability of the individual, but you should probably be more worried about the life fulfillment of the individual. So people on the career ladder, especially young adults, and for anyone that's guiding them, I want them to believe in what's possible and I want to give people permission to go try something that may feel a little quixotic. Sam.