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Podcast Episode Summary: Modern Wisdom #1071 - Bill Gurley - If You Hate Your Job, This is How to Start Over
Podcast Title: Modern Wisdom Host: Chris Williamson Guest: Bill Gurley (Venture capitalist, general partner at Benchmark, former Wall Street analyst)
Episode Overview In this episode, Bill Gurley discusses career regret, finding meaningful work, and the challenges of reinventing oneself professionally. He shares insights from his extensive career in venture capital and explores the psychological aspects of career choices.
Key Themes and Discussions
- Understanding Career Regret
- Statistics on Regret: Gurley mentions that a survey he conducted revealed that around 70% of people would choose a different career if given the chance.
- Inaction vs. Action Regret: Based on Daniel Pink's work, Gurley discusses how people tend to regret actions not taken more than actions taken, leading to a phenomenon called "boldness regret."
- Educational Paths and Career Choices
- Gurley critiques the current education system for pressuring students into "safe" jobs that may not align with their passions, which can lead to burnout.
- He encourages people to pursue what they love and to be aware of societal expectations concerning career choices.
- Framework for Regret Minimization
- Regret Minimization Framework: Inspired by Jeff Bezos, this mental exercise involves imagining oneself at an older age and reflecting on potential regrets to drive current decisions.
- Seeking Mentorship: Gurley emphasizes not only the importance of mentors but also the value of peer relationships for sharing experiences and guidance.
- Passion vs. Perseverance
- Gurley discusses Angela Duckworth's concept of grit, suggesting the need to balance perseverance with passion. He believes that love for one’s work is crucial to avoid burnout.
- Navigating Career Transitions
- Signs of Transition: Gurley suggests asking oneself if they could envision doing their current job for the next 30 years as a litmus test for career satisfaction.
- Exploration of Interests: Encourages individuals to explore hobbies and interests outside of work to discover potential new career paths.
- The Role of AI in the Future of Work
- Gurley discusses the transformative impact of AI on various job sectors, emphasizing that adaptability and embracing new technology are key to remaining relevant in the workforce.
- He believes those who integrate AI into their work processes will have a competitive advantage.
Key Takeaways
- Regret is a powerful driver: Many people wish they had pursued different careers, highlighting the importance of taking bold actions in life.
- Find what you love: Identifying and pursuing passions can lead to greater job satisfaction and success.
- Adaptability is crucial: Embracing AI and new technologies will be essential for future career development.
- Community and mentorship matter: Building relationships with peers and mentors can provide the necessary support and guidance in career transitions.
Additional Resources
- Book Recommendations: Gurley encourages continual reading and learning to stay ahead.
- Personal Stories: He shares anecdotes of successful individuals who reinvented themselves, emphasizing the learning that comes with exploring diverse fields.
Conclusion Bill Gurley's insights provide a roadmap for those feeling stuck in their careers and encourage listeners to take active steps toward fulfilling their professional aspirations. By addressing the fear of regret and promoting the pursuit of passion, he offers a refreshing perspective on career reinvention.
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For more content from Bill Gurley and other guests, visit the [Modern Wisdom Podcast](https://www.chriswillx.com/podcast).
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Journey to Understanding Career Regret
0:45 to 2:52
Bill discusses his background and the inspiration behind exploring career regret.
“and I finished this third one and saw a through line with these other two from people that were in wildly different fields.”
The Impact of Regret and Inaction
2:52 to 4:59
Bill explains the concept of boldness regret and its effects on individuals.
“biggest regrets people have and and and he showed me a graph it actually gets worse as you get older towards end of life are regrets of inaction he calls them boldness regrets it's what you didn't do.”
Current Education and Its Consequences
4:59 to 7:30
Discussion on how the education system influences career choices and regrets.
“I was hoping to bring up one of the many biases I've read about in all the behavioral science books, but I'm going to go to a different place, which is I think we ruminate a lot.”
The Regret Minimization Framework
7:30 to 9:20
Exploration of Jeff Bezos's framework for minimizing regret in decision-making.
“imagine a catastrophe than deal with the uncertainty.”
The Pressure of Career Decisions
9:20 to 11:50
Bill reflects on the pressures young people face in choosing careers and majors.
“We've built this pipeline for these kids that's so intense.”
The Complexity of Passion and Perseverance
11:50 to 14:02
Discussion on the balance between passion and perseverance in career success.
“and you know Height says it he has a chapter called Let the Awesome Play or something Rick Rubin's been pounding on this he talks about it in his We looked at Gene Twangy's work Generations Is that another one?”
The Challenge of Finding Passion
14:02 to 15:10
Exploring the complexities of finding and engineering passion in life.
“Like we taught them to persevere, which is.”
Regret Minimization and Life's Shortness
15:10 to 16:21
Discussing how to avoid regret by embracing life changes and avoiding financial traps.
“Like you're going to get to the end and then it's done.”
The Complexity of Flexibility
17:40 to 19:15
Examining how the perception of flexibility can affect life choices and metrics.
“Because flexibility is actually a really difficult thing to show off.”
Finding Fulfillment in Work
19:15 to 20:26
Discussing the importance of fulfillment in one's career and the potential for change.
“if they're really thriving in something that they may not perceive to be an occupation.”
Show all 49 chapters
Stories of Overcoming Doubt
20:26 to 22:45
Using personal anecdotes to illustrate the power of support and belief in oneself.
“There's a, there's, I don't know if you've seen this, but you know who Steve Harvey is, the comedian who does the talk, does Family Feud now.”
Financial and Cultural Barriers to Change
22:45 to 24:11
Identifying barriers that prevent individuals from making career transitions.
“It's quantifiable, observable, and hidden metrics.”
Fear and the Journey of Change
24:11 to 27:37
Understanding the fear surrounding career changes and overcoming societal expectations.
“You know, it's about as low a rung as you have in that business.”
The Role of Stories in Changing Perspectives
27:37 to 28:00
Highlighting how narratives can influence beliefs and make ideas memorable.
“I have none of those in there for this reason, because I wanted to help people get past the fear by giving them the motivation and the method to do it.”
The Power of Storytelling in Retention
28:00 to 30:20
Explore how storytelling enhances memorability compared to facts alone.
“That's kind of like, you know, the tune from a song.”
Facing the Risks of Starting Over
30:20 to 32:50
Discuss the fears and considerations of starting a new career in your 30s or 40s.
“You know, the idea of not just what am I going to do, but, you know, I should have had my life together by now.”
Real-Life Examples of Career Pivots
32:50 to 37:10
Hear inspiring stories of individuals who successfully pivoted their careers later in life.
“And one night, this is such a, like, it's part of why I love like self-help books and ideas so much.”
Finding Passion Through Continuous Learning
38:40 to 42:00
Understand the link between passion, learning, and career fulfillment.
“Joe Hudson's got this line, enjoyment is efficiency, he says.”
Recognizing the Right Time for Change
42:00 to 45:00
Learn how to identify when it's time to change your job and explore new opportunities.
“I used to be, and it just feels like it's time for me to grow now.”
The Power of Passion Projects
45:00 to 46:40
Discover how personal interests and side projects can reflect your true career aspirations.
“I just keep on thinking about pickleball and I'm really interested in the sport and I'm interested in how it's growing and I love playing it with my friends.”
Turning Passion into Profession
46:40 to 48:20
Hear inspiring stories of individuals who transformed their passions into successful careers.
“You know, if you really love being around that stuff, there's tons of opportunity.”
Navigating Career Doubts with Peer Support
48:20 to 50:00
Understand the importance of peer relationships in overcoming career challenges and doubts.
“New place for coffee, new place to work, to take your calls, your morning walk.”
Building Mentorship Relationships
50:00 to 53:20
Learn how to develop effective mentorship relationships that can guide your career.
“And how much of that is transient that I could just finesse my way out of.”
The Dual Role of Mentors and Peers
54:45 to 56:00
Explore the distinct yet complementary roles of mentors and peers in career development.
“They're struggling with the same challenges you're sharing and sort of going on the journey together.”
The Power of Mentorship
56:00 to 57:20
Learn how to effectively seek guidance from mentors and the importance of studying aspirational figures.
“And so what I encourage people to do is divide mentorship into two different categories.”
Flattery as a Networking Tool
57:20 to 58:50
Discover the role of flattery in successful outreach and networking strategies.
“ish it was so flattering for people to be invited on a podcast you know one of the other things this is such a funny trick that I still use now.”
The Grind vs. Passion
58:50 to 1:01:55
Explore the difference between grinding through work and finding passion in what you do.
“Or is it going to be somebody else looking to get put in touch with the person who handles their partnerships or the, whatever it is.”
Appreciation for Support Systems
1:01:55 to 1:07:15
Understand the importance of acknowledging those who help you along your journey.
“But I don't know that most humans could.”
Continuous Learning in Knowledge Work
1:07:15 to 1:10:00
Learn about the necessity of continuous learning and the differing attitudes towards work across professions.
“a process that you will feel really good about at the end of your life.”
The Work Ethic of Young AI Founders
1:10:00 to 1:11:35
Explore the relentless work ethic embraced by young AI entrepreneurs.
“It actually was developed in China, which means 9 a.m.”
AI: Threat or Opportunity?
1:11:36 to 1:13:24
Discuss the contrasting perceptions of AI as a threat or a tool for growth.
“If you're doing it and it doesn't hurt anybody else, you do to your workload as you wish.”
The Impact of Guidance on Personal Growth
1:14:56 to 1:17:31
Understand how advice can amplify existing traits rather than correcting them.
“So guidance doesn't sculpt us into something new.”
Emotional Work and Regret Minimization
1:17:32 to 1:23:57
Investigate the importance of emotional awareness in decision-making.
“I think when you're—one of the benefits of being 18 is you don't see the end of times at all.”
Imagining Alternate Realities
1:24:00 to 1:25:10
Learn how to visualize different life paths and decisions effectively.
“I think one of the reasons I was a, uh, useful venture capitalist and, um, One of the reasons this regret minimization thing worked for me is I think I'm very good at bringing forward the future in my brain.”
Key Traits of Successful Founders
1:25:10 to 1:27:55
Discover the essential traits that venture capitalists look for in founders.
“And it makes those exercises work better.”
The Determinism of Champions
1:27:55 to 1:29:56
Understand the importance of determination and grit in successful individuals.
“All of his questions were around that one very thing.”
Pivots and Founder Resilience
1:29:56 to 1:31:05
Learn about the significance of founder adaptability through company pivots.
“Well, could you imagine, again, that is, and this is a fucking wonderful little microcosm of exactly what we were talking about.”
The Importance of the Founder
1:31:05 to 1:33:12
Explore why the founder's vision often outweighs the original business idea.
“but they had built this tool to develop the game.”
The Emotional Side of Venture Capital
1:33:12 to 1:35:51
Understand how emotions influence investment decisions in venture capital.
“This thing, the beverage that you're drinking is mine and it's the first big company that hasn't been something that I've directly operated aggressively myself that I've founded.”
Risks of Taking Venture Capital
1:35:51 to 1:38:01
Discuss the potential downsides of accepting venture capital for startups.
“You can't get enough information fast enough through that.”
The Impact of Venture Capital on Founders
1:38:01 to 1:40:23
Explore how venture capital affects ownership and exit strategies for founders.
“typically leads to a C and the ownership that a founder has can shrink pretty dramatically.”
AI's Role in Personal Empowerment
1:40:24 to 1:43:02
Understand how AI can enhance personal and professional capabilities.
“And then before they know it, they're like, what the fuck am I working for?”
The Future of Work and AI Threats
1:43:03 to 1:48:45
Identify which jobs may become obsolete due to AI advancements.
“Like to know whatever industry you're in, there is an edge of what is AI capable of in this industry.”
Innovative Ideas for Starting Over
1:48:46 to 1:50:48
Discover entrepreneurial ideas and strategies in the AI landscape.
“Someone needs to kind of make sure the translation's right, but that's a different job.”
The Value of Diverse Perspectives in Innovation
1:50:49 to 1:52:00
Learn how switching fields can lead to greater innovation and insights.
“So anyway, those are things that pop into my brain when you say that.”
The Power of Diverse Learning
1:52:00 to 1:53:15
Explore how learning from different industries can lead to unique insights.
“like if they enter through the side door.”
Cinematic Passion Projects
1:53:15 to 1:54:49
Discover how the host's passion for cinematography elevated the podcast.
“And it's largely a passion project wing of what we do, but it's cool.”
Navigating Taste and Networking
1:54:49 to 1:55:42
Understand the nuances of taste and networking in creative endeavors.
Connecting with Bill Gurley
1:55:49 to 1:56:42
Find out where to follow Bill Gurley and his professional updates.
“I'm glad that you're occupying some of those high-rises down.”
Transcript
Automatic transcript. May contain errors.0:00Chris Williamson:What got you into thinking about the idea of career regret as somebody that's had a very seemingly successful and fun career? Why did you think about it?
0:09Bill Gurley:I used to, so I spent 25 years as a venture capitalist and the four years before that as a sell side analyst on Wall Street. And through that process, I started writing as a way to differentiate myself. And so I was an early blogger. It was actually a fax. That's how old I am when I started. and I got in the habit of when I had ideas, jotting them down and then, you know, either developing them. A lot of them ended up just undeveloped, but if I developed them, they would become a blog post. And there was a period in my career where I was reading a ton of biographies and I finished this third one and saw a through line with these other two from people that were in wildly different fields.
0:53Bill Gurley:And I jotted those notes down and that thing kind of simmered and breathed and took on a little bit of a life. And I got asked by the dean of the business school here in Austin, University of Texas, to talk to the MBA class one day. And I was like, can I do this? And he said, sure. So I pulled it out and developed it a little bit as a PowerPoint presentation. Anyway, they posted that on YouTube. A few people noticed, some people that have been on your show, James Clear noticed, and he posted it on his website. And people started prodding me to develop it as a book. And a few years ago, I decided to begin retirement as a venture capitalist.
1:34Bill Gurley:It actually takes a while, unfortunately. And in that window, I thought about doing this. I thought about doing a book. And a lot of people wanted me to do a book. A lot of people wanted me to do a VC book or an investment book or a tell-all book on the Uber experience. And I was more drawn to this idea. And a few other people prodded me who said, you know, like, go, go do. And it felt more authentic. It felt like something that could have a bigger impact. And I was drawn to that at this moment in my life. I was drawn to this particular thing. So I spent like six years working with a co-writer and researcher developing and developing it further and making it this way.
2:14Bill Gurley:But you used the word regret. We did, along the way, I launched a survey on SurveyMonkey that said, if you could go back and start over, would you do a different career? And seven out of 10 people said yes. And I eventually took that to Wharton People Analytics, and they did a more scientific version of it, much broader audience, and came back six out of 10, but very similar. and that notion of career regrets interesting I had the opportunity to talk to Daniel Pink who you may know who wrote been on the show about regret about regret and in that book he says the biggest regrets people have and and and he showed me a graph it actually gets worse as you get older towards end of life are regrets of inaction he calls them boldness regrets it's what you didn't do.
3:05Bill Gurley:Like humans are great at forgiving themselves, made a mistake, learned from it, won't do it again, but they ruminate about what they didn't try. And so I, you know, I've thought about this long and hard now since I've been working on it for six years. I fear our current education path has become a bit of a conveyor belt. People like, we're pushing these children into this meat grinder. And we're pushing them towards jobs that are typically called safe jobs, at least before AI. And I think they're learning to grind. That's what Angela Duckworth's been saying. Now, the perseverance part, we've taught them, but if they don't have the love for it, it turns into burnout.
3:52Bill Gurley:And so the purpose of this book that I wrote is hopefully to give as many people permission to go do what they want in life, you know? And, and look, I'm sure it won't touch everybody, but if there's a subgroup of people who read this and have the conviction that they can go succeed in this thing they love, I think that would be a huge impact on the world. Like, I think the people that do that are the people, you know, these people like that are just love what they do and not only are they more successful, but I think they radiate a bit, you know, and spread positive energy.
4:30Chris Williamson:Well, they're mimetic as well. They become a role model for other people. That's right. Go and do, oh, he took a chance on that thing that he wanted to do and wow, it didn't work out and his life didn't blow up or it did work out and he's really happy.
4:42Bill Gurley:That's right.
4:43Chris Williamson:Thinking about the fact that we seem to regret inaction, boldness regret. Yeah. Have you reflected on why you think that is, what it is in the human mind that causes us to prefer decisiveness over...
4:59Bill Gurley:I was hoping to bring up one of the many biases I've read about in all the behavioral science books, but I'm going to go to a different place, which is I think we ruminate a lot. Like our brains, you know, constantly are replaying things in our minds. and maybe that's what dreaming is too. But I think because of that, it's very easy to imagine these what ifs, to build a story, especially a positive story around the what if that didn't get done. And then you compare that to your current life. And unfortunately that can create anxiety, but I do think that might be part of it. You'll be familiar with the Zygonic effect.
5:43Chris Williamson:I'm not, tell me. Oh, cool. So there was a psychologist who began studying waiting staff. And they realized that these waiting staff had unbelievable recall while the tables were still open. You know, you've ever been to a restaurant and you see some waiter come up and they're stood, no pen, no pads, no iPad, hands behind their back. And they go, this guy's crazy. He's insane. I'm definitely going to get something wrong. And sometimes you might go, I'm going to, we'll take the sprouts by extra bacon, no goat's cheese. You want to just see if, oh, all right, I missed a notepad. And the study ended up finding out the Zygarnik effect, which is an open loop, closed loop bias that exists inside of the human mind.
6:33Chris Williamson:While the tables were still open, the servers were able to recall what the orders were very closely. And as soon as they went, nothing at all. You know, a perfect example in almost everybody's life with this. I'm quite bad at this actually, but it still holds true. Hotel rooms. Let's say that you're moving from city to city to city. You're not bad at remembering the hotel room of where you are now. But if I was to say, which hotel room did you stay in two hotels ago? I'd give it 7.35. I don't know. I have no idea. It's the same reason why cliffhangers work at the end of TV shows to get you to watch the next one.
7:10Chris Williamson:Yes, yeah. The open loop. The human mind abhordes an open loop. Yeah. And I get the sense that when it comes to boldness, regret, the main thing that you have is an open loop. Now, the human mind abhors open loops and uncertainty and ambiguity so much that we'd rather imagine a catastrophe than deal with the uncertainty. That's what a lot of anxiety, sort of future projected regret kind of is, right? I don't know what's going to happen, And so I'll imagine the worst thing. And at least for a moment, I have certainty, even if the certainty is horrible. And this is the same thing, I think, in some regards, but in reverse.
7:49Chris Williamson:What could have happened? Yeah. What could I have done?
7:51Bill Gurley:And there's an interesting way to flip it on its head. When Jeff Bezos was trying to convince himself to go start Amazon, he had this incredible job at D.E. Shaw. And David Shaw didn't want him to leave. So he was trying to talk him out of going. And Bezos has this thing. It's on YouTube. You can go watch it. But he self-proclaimed it was very nerdy, but he called it the regret minimization framework. And he just imagined he's 80 years old and was trying to get advice from his 80-year-old self about what to do. So he like put himself in that future place where he might have that boldness regret.
8:28Bill Gurley:And in my own career, I had two different jobs I started and then switched before I got into venture capital, which was definitely my dream job. And in both of those cases, a couple years in, I paused and reflected. And I only thought about this as I've been promoting the book. I paused and reflected, do I want to do this for 30 years? and was able to like fast forward that in my brain. And I was unhappy with that reflection, which encouraged me to think about what's next.
9:09Chris Williamson:When it comes to the regret minimization framework, which I love and I kind of can't believe isn't bigger. I'm aware it is among people that read the sort of stuff that you do or maybe I do. Yeah, yeah. It is a really wonderful idea. and um i guess jeff's got other stuff that he can be well known for so perhaps you know well it's
9:30Bill Gurley:it's actually quite synonymous with the uh the uh one of the seven habits of highly effective people begin with the end in mind it has it has a similar kind of when looking at the regret minimization framework what are the things that what are the common pitfalls that you've seen
9:50Chris Williamson:people do, even both inside of their career and outside of it. You must have reflected on this a lot.
9:55Bill Gurley:Yeah, I have. One thing that I think, especially with the modern young people, I think one problem that I think exists, because we've built this, I call it in my book a conveyor belt, Jonathan Haidt called it a regret, or I'm sorry, a resume arms race. We've built this pipeline for these kids that's so intense. I think when they get to their first job, they feel like it's the result of all this investment. And they feel like tweaking any way away from that is throwing away the investment. Does that make sense?
10:33Chris Williamson:Like a loss aversion type thing?
10:34Bill Gurley:Yes, yes, yes. I invested all of this to get to this college, to get to this degree. And if I move away from that, did I just waste all that time. And, you know, this is despite the fact that there's a lot of studies that have been done, like, I won't get the numbers exactly right, but like five years after college, 40 % of people are no longer working in the field that was their major. And that number gets bigger at 10. But it doesn't mean that they don't feel trapped or that that number might not be higher if they didn't feel trapped. And when I mentioned this to young people, there is this weight.
11:16Bill Gurley:There is this weight they feel, like an obligation to, especially maybe -
11:21Chris Williamson:Decisions that they locked in when they were 17.
11:23Bill Gurley:Yes. Well, and that's another thing. When I was younger, the colleges wouldn't let you declare a major until the end of your sophomore year. Many schools, you have to apply to the major now. So we've moved the decision of what major are you going to pick from the end of your sophomore year to the end of your junior year in high school. Like that's, you know, three years forward and less time to, there's a lot of people, a lot of smart people that just say we don't allow children enough time to explore. and you know Height says it he has a chapter called Let the Awesome Play or something Rick Rubin's been pounding on this he talks about it in his
12:09Chris Williamson:We looked at Gene Twangy's work Generations
12:12Bill Gurley:Is that another one?
12:13Chris Williamson:Yeah so Generations is really fascinating this stinks of you highly recommend it Okay I will and she talks about extended adolescence sort of twins with some of Height's stuff but you've got a real interesting duality going on, which is in one world, you've got these kids that are sort of being forced to become adults more quickly than ever before. We expect you to know what you potentially, the set of railroad tracks for the rest of your life, the next 30 years of your career, and you're only 17 and you've got to know and apply. And then at the same time, kids are moving out of the house later.
12:48Chris Williamson:They're getting their driver's licenses later. They're getting employment later. They're getting into relationships at lower rates, less alcohol, all of the things that we would have typically associated with being an adult are not present as we're trying to force structural adulthood onto them. They're socially very immature, professionally expedited. And he ties them together? Gene Twangy, yeah, for sure. I think that, oh, actually, no, no, no, no, no. No, great point. And I don't know. And I don't think so. Now, there might be some rebellion going on. Like, oh, God, everything just feels like I need to get my act together.
13:31Chris Williamson:How can I do these other things? Just so much of my cognitive real estate is taken up. I could see that. Maybe that would be a compensatory.
13:38Bill Gurley:Yeah. Like I mentioned, I think when about 10 years after Duckworth wrote Grit, She said that she wished she had positioned it as 50-50 passion and perseverance. And if she could do it again, she'd put more on the passion because she thinks we taught a whole generation of the high performer children how to grind. Like we taught them to persevere, which is. Well, and so I get that.
14:08Chris Williamson:Grit was a massive book. I don't think that she should lay at the feet of her pen the issues of this stuff. but I think one of the reasons why from a personal development standpoint it makes it's a bit more seductive to over-index on the perseverance than the passion is that passion feels more difficult to engineer. Fair enough. So how do I get the thing the line the stuff right it feels a bit more egalitarian Yes. to say no matter what it is you're doing if you hold hard enough you can get I do think it is the hardest question.
14:41Bill Gurley:What is? Finding it like finding it and knowing it you know Knowing it's a little easier, but finding it. There are a lot of 17-year-olds who appropriately, if you ask them, what is your passion? What do you want to do? They appropriately say, I don't know. Because it's the truth. They don't know. But I think that's okay. It's just we shouldn't force the question upon.
15:05Chris Williamson:You've got this line, life is a use it or lose it proposition. Yeah. What's that mean?
15:09Bill Gurley:Well, I mean, it's tied to the boldness regret, right? Like you're going to get to the end and then it's done. And only if you think in the way that Bezos did with his regret minimization framework are you going to hold yourself accountable for that line. You know, the recognition that life moves much faster than any of us realize and then it's done. And you can get locked in even sooner. If you spend up to your limits, you can freeze yourself in a job that you can't leave. And you can do it with personal commitments as well. My second career was going to Wall Street. And I can't tell you the number of people I worked in with Wall Street that had, for their age, ridiculously high salaries.
16:03Bill Gurley:But they had to place in the Hamptons, the summer lease. They tried to get into the membership club. Like they spent right up to the limit and now you can't switch. You know, you can't switch.
16:14Chris Williamson:Yeah, you're locked in at this very high burn rate, which means you need to keep pouring fuel in the top of it.
16:19Bill Gurley:Yes, yes. I have like for young adults that are lucky enough to have a job with a decent salary, I would heavily encourage them not to spend against it just so they can have the flexibility to do other things, move cities, change jobs, all of which may be the right path for them.
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17:18Chris Williamson:Getting your blood work drawn and analyzed like this would usually cost thousands, but with Function, it's just$499. And right now you can get$100 off, bringing it down to 399 bucks. Get the exact same blood panels that I get and save that$100 by going to the link in the description below or heading to functionhealth.com slash modern wisdom. That's functionhealth.com. slash modern wisdom. Yeah, it's weird, isn't it? Because flexibility is actually a really difficult thing to show off. It doesn't... Even flexibility is only show-offable in so much as you can take a photo of you on a plane or you at a holiday or you at a...
18:00Chris Williamson:Which again is not quite the flexibility that we're talking about here. So I've always thought about this, the difference between hidden and observable metrics. We'll often trade a hidden metric for an observable one. Trade the quality of our sleep for a slightly bigger pay packet. We'll trade the hours of peace that we have on a Saturday for position improvement. will trade, I mean, you know, some people will trade a caring, supportive wife for a very difficult, younger, hot one. You know, the trades are everywhere. Yes. I think that's a good framing. So is many people, especially people who maybe aren't so fired up with their jobs and their careers might think I can get my fulfillment elsewhere.
18:51Chris Williamson:Why should I care about my career? is just the thing that I do from nine to five or whatever, eight to four every day. Why should I try and optimize that? Is being fulfilled at work a luxury?
19:06Bill Gurley:I guess what I would say is I have an immense amount of respect for someone who adopts that mindset, the one you described, especially if they're really thriving in something that they may not perceive to be an occupation. That could be a religious community. It could be volunteer work that they do. Um, I would highlight to them, there might be a career in that, you know, like if they wanted to be around it all the time, but my main goal isn't to tell those people they aren't being successful. Like if they're happy and passionate about that lifestyle, like that's great. I'm not, I'm not casting any, any shadow on that whatsoever.
19:53Bill Gurley:If you are the type of person that is either unhappy with your work, like so much so that it's impacting your quality of life, or even better, if you're someone that has this inkling, this little notion in their brain, but maybe doesn't have the confidence or the permission, they don't feel like they have the permission to go do it, that's who I want to read my book. Like that's who I really, really want to read my book. Um, there's this, there's a, there's a great story that there's a couple of these actually, but I'll, I'll, I'll choose the Steve Harvey one. There's a, there's, I don't know if you've seen this, but you know who Steve Harvey is, the comedian who does the talk, does Family Feud now.
20:34Bill Gurley:Um, he tells this story, did, I think he told it on Oprah, that when he was seven, the teacher asked them to, for, as an exercise to write down a sheet of paper what they wanted to be when they grew up. And he claims he got called last. And the teacher said, the others she read, but for his, the teacher made him come to the front of the room and read it out loud. And apparently he had a stuttering problem, but it said, I want to be on TV. And she thought he was like not taking the exercise seriously. and she condemned him for writing that. So much so that she called his mother and he got in trouble when he got home.
21:16Bill Gurley:So he got sent to his room. He's worried that his dad's going to come in there and read him the riot act. And his dad comes in and sits next to him. Here's the whole story. And he says, here's what we're going to do. Let's take that piece of paper and put it right here in your bed stand and I want you to read it every single day. And you hear a story like that, you know, And I don't think, there's a lot of people, I think that that's a very hard thing to do. I think that for parents, and I'm a parent of three and I've lived through this phase that we're talking about, your intuition as a parent, like some in your DNA somewhere, is to look after the economic welfare of this child.
21:58Bill Gurley:You want them to live a good life. And it's very hard not to associate that mostly with money. And so this thing that Steve Harvey's dad did for him, I think, is kind of a really like a very unique thing. I think it's very hard to do. And I hear a story, McConaughey has a very similar story about when he switched from law school to film school. His dad told him, well, don't half-ass it. And he said that was the last thing. He thought his dad was going to yell at him. And his dad kind of gave him like this push. And that's what I want the book to do. Like if someone has that inkling that they want to go do something that the world may not think they're capable of or think they should do, I'd love to unlock this latent human potential.
22:45Chris Williamson:You know what it comes back to? It's quantifiable, observable, and hidden metrics. Again, the observable metric of financially free, this is how much they earn, this is the track that they would be on. Hidden metric, how passionate are they? Are they happy when they're 35?
23:02Bill Gurley:Yeah.
23:04Chris Williamson:So I guess one of the situations that so many people must be in is someone, one version of them successfully pivots and another version of them stays stuck for life.
23:17Bill Gurley:Yeah.
23:18Chris Williamson:Why do some people successfully pivot and others end up getting stuck?
23:25Bill Gurley:Well, I mean, you could come up with a number of things. One of them is financial, which we've talked about. You could be overspending. There's a different case where you're just stuck financially, like you're living hand to mouth. I have a profile in the book of Jen Atkin, who I don't know if you know, she is probably the most successful hairstylist of all time. Like not only achieved, touched the top rail of that, but then launched beauty products, sold that company. But she moved to LA with$300 in her pocket. And that's not to say anyone can do that, but like there are stories of people with near nothing starting on the very bottom rung and finding their way to be successful.
24:07Bill Gurley:There's this classic meme of starting in the mailroom in Hollywood and David Geffen and Barry Diller, all these people started in the mailroom. You know, it's about as low a rung as you have in that business. So I think it's possible, but you may feel stuck financially. So you may feel that you can't get there. And then the other one, you know, it could be like this perception. McConaughey had this perception that his father wanted him to be a lawyer. It's probably just that Matthew had told him he was going to be a lawyer and he was supporting that. But that weight can be there, too. Like you may feel, I think there are certain cultures where like being a doctor is considered really, in Russia, like being an academic was considered.
24:57Bill Gurley:So you may feel pressure from your family as this is the thing people in my family do. And I've seen that. And I've met people who have that weight upon them. Those are all kind of things that could restrict this movement.
25:10Chris Williamson:What about the fear? There has to be a huge chunk of people that just, what if this doesn't work? It's sort of ambient, ephemeral, this fugue, fog thing that's come down on them.
25:25Bill Gurley:If you allow me to give you a little history of how or why, I would say I spent six years turning the original presentation into a book. and I had this thing I really wanted to achieve, which was to embed as much stories and narrative into it as possible. And I was listening, I know you've had Morgan Housel on. He's the absolute goat. And he was on a podcast called Why We Write talking about the power of narrative. And so the book is divided, it's structured unlike most books. It's divided into two parts, but they interleave. And so every other chapter is a Atlantic size article about someone that started on the bottom rung with intention and made it to the top.
26:15Bill Gurley:And the reason I wanted to include those is precisely for the reason Morgan talks about, which is, I think these things stick in your brain more. Like a lot of the books in the category that have done extremely well in career read like a textbook. Do A, do B, then do C. But they don't have this kind of spirituality to them that I think can infect the brain a little bit more.
26:42Chris Williamson:Does that make sense? It's 100 % correct. I mean, Ben Shapiro's famous line of facts don't care about your feelings is as backward as it could be, that feelings don't give a single fuck about the fact.
26:53Bill Gurley:So we have eight, nine, or 10, I should know the exact number, but I can't recall right now, of these profiles. And I alternated them with the principles. And I wasn't thought about it like candy and vegetables, you know, or something. But you get some of both. It brings the ideas to life. Yes. And I think the reason I told that long story was an answer to your question about fear. I think seeing this many stories, and they're all, by the way, I chose, every one of them from a field that your parents would probably tell you not to go into. I intentionally skipped, you know, investment bankers and...
27:31Bill Gurley:Doctors. Yeah, all the stuff that everyone knows is...
27:35Chris Williamson:Nice linear progression.
27:36Bill Gurley:Yes. I have none of those in there for this reason, because I wanted to help people get past the fear by giving them the motivation and the method to do it.
27:48Chris Williamson:Mm. I hope it works. me too well you're certainly right about changing people's opinions with beating them over the head with frameworks and justifications it just it straight up does not stick yeah um pithy mantras and quotes and stuff can do they're a nice compression algorithm yeah i think for bigger things um but really what you're optimizing for and this i'd be interested to know if you if you agree with me on this i think you're optimizing for memorability yes and i'm just i just don't think that regardless of how well-written, whimsical, insightful something is, it doesn't, the human brain, the keyhole isn't the same, it doesn't retain things quite as easily.
28:36Chris Williamson:The aphorism and stuff is nice. That's kind of like, you know, the tune from a song. It's the lead melody from a song that you can hold on to. But if you give somebody a story, how are you going to forget that?
28:46Bill Gurley:Years ago, and I don't know when it started. Actually, it's funny I just said I don't know where it started and then something popped in my brain I fell in love with these long form non-fiction articles there's a website called Long Reads okay that it has best of and it's a lot of Atlantic stuff that kind of thing the thing that popped in my head was there was a New York Magazine article uh Suge Knight and and uh and Snoop and I think Biggie were on the cover of New York Time Magazine when I was it was in 93 or 94, and it was 20 pages. That may have been the first one that got me into this. But that led me to a book called The New Journalism, and there's another one called The New New Journalism, about these writers that kind of left the being beat writers on newspapers and started doing this longer form journalism and how it brought stories to life.
29:41Bill Gurley:I think Truman Capote's highlighted in that. Tom Wolfe put together the first one. And then the second one has Krakauer and Lewis and like all the modern.
29:52Chris Williamson:Well, now we've seen this pivot into Substack, right? That people that were previously hardcore journalists have made their entire careers on Substack. And then if you're somebody like Barry Weiss, you've done this sort of W-turn thing and loop back on yourself enough and you end up in charge of CBS. You're Matt Taibbi and you end up in charge of the Twitter files or whatever.
30:12Bill Gurley:I'm a huge Barry fan.
30:16Chris Williamson:So talk to me about the risk of starting over in your 30s or 40s. Yeah. You know, the idea of not just what am I going to do, but, you know, I should have had my life together by now. Is it really, you're telling me I'm going to start again at 37? I'm going to be at the bottom of the pile, and I've got all this sunk cost fallacy from before. What are people going to think of me? What's the real risk of starting again in 30s and 40s?
30:40Bill Gurley:Well, I mean, one thing I would encourage you to do, there was this book I read when I was really in, I think back in business school called Shark Proof by Harvey McKay. He wrote, he's known for his sales book, but he wrote a book about careers. And he said to keep your dream job. This was an older book, so he said keep it in a Manila folder and a file, but you could create it in a Google Doc or something. That we're just keeping notes. like, well, if I do it one day, you know, and, and, and everything you learn, people you might talk to, I think you just pile more and more stuff in there and it'll start to feel more real.
31:16Bill Gurley:Like you can, you can begin the process before you make the leap. Right. And then the, the, the second thing, I'm going to say three things. The second thing I would say is if you have some curiosity that's occupying your downtime, that's a really interesting tell. You know, when I was an engineer, I got a computer engineering degree and I was working at Compact Computers in Houston that was a big hot company back in the day. And I was going home at night and I had started, I'd learned about stocks and I was trading stocks. You know, I'd read one up on Wall Street. I had this, I forget It was called this book.
31:57Bill Gurley:You just get this book with all these one-pagers on every stock. That's what I was doing in my spare time. So if you're doing something like that in your spare time, it's calling you. And then the third thing, there's a chapter in the book actually titled Never Too Late. And we list about 20 people that did post-40 pivots, and we go deep on four of them. My favorite being local Austinite Burt Beveridge. um Bert's uh nickname is Tito so that'll that'll tell you who he is but um seismology degree undergrad worked in oil and gas for for several years um ended up down in South America where he got frightened by a few experiences um so he hung that up out of fear and the boom bust cycle became a mortgage broker um didn't really love it you know not sure he equated his identity to being a mortgage broker.
32:53Bill Gurley:And one night, this is such a, like, it's part of why I love like self-help books and ideas so much. He's watching a PBS special that says, take out a sheet of paper, draw a line down it, put the stuff you love to do on the left side and the stuff you're good at on the right, and see if you can find a through line. And he's looking at this sheet of paper and realizes he wants to start a spirit company. He's got like chemistry on the right. It's like hanging out at bars on the left. And he didn't know jack shit about launching a spirit company. And it turns out Texas is probably the worst place you'd ever, at the time, there was no one that had a license for a spirit company in Texas.
33:41Bill Gurley:But of course, Tito's is now the most best-selling spirit in North America. He owns 100 % of it himself.
33:48Chris Williamson:No way. The whole thing's bootstrapped.
33:50Bill Gurley:Yes.
33:54Bill Gurley:Oh, fucking hell. But it's such a great story. Like, it's just such a great story. And now, you know, he's at the phase in his life where he's giving back and launching foundations. And this is my point. Like, I had a young person at John Hopkins raise their hand say, but I don't want to chase my passion. I want to be purpose-driven. And I thought to myself, you know, every profile in the book, these people are touching more lives than they could have ever imagined. I don't want to chase my passion.
34:25Chris Williamson:I want to be purpose-driven.
34:27Bill Gurley:I think it's part of a new movement to just like feel good about yourself. Like my main goal in life is to help other people.
34:36Chris Williamson:serve yeah okay that's interesting well it's like no it's no it's noble on the surface and there's certainly some things you know in the same way this person has high burn rate family to support you don't have the luxury in quite the same way um this person there are some jobs that just suck yeah there are some jobs you're serving your country or you're you know i'm sure lots of people love street cleaning but i would imagine that some people do it more out of a sense of service than they do out of a sense of passion. Um, my only point was these people that are able
35:11Bill Gurley:to climb from the bottom rung to the top and do it in the right way, end up touching hundreds and hundreds of lives.
35:18Chris Williamson:They're serving in a, a, a much more seamless way that's leveraged as well.
35:22Bill Gurley:Yeah.
35:22Chris Williamson:Yeah. Yeah. Yeah. Yeah.
35:23Bill Gurley:I mean, my, one of my favorite on that front is I, many years ago, because I was involved with open table, I met Danny Meyer and who's the famous restaurateur in New York that also built Shake Shack. He has a great book, Setting the Table, if people haven't read it. But if you talk to people in the restaurant industry and they worked even for a year at a Danny Meyer restaurant, it's like meaningful to them. Like it's on their resume. They talk about it all the time. Like there's almost this church of Danny Meyer like for everyone that rolled through it. That's gotta be, that's gotta just feel amazing.
36:01Bill Gurley:What is it about his demeanor or culture or ethos? The book talks about this kind of understated sensibility to his book, to hospitality. Like just trying to read the room on each and every customer and really understand what they're trying to optimize and to help them do that as much as possible. But his journey is about more than that. That's what his book's about. His journey is about being hyper-curious and an excessive learner. Like every single step along the way, including today, he's still doing it. You know, last time I talked to him, he just got back from Europe. He had taken all his chefs on a tour of Europe together, jotting notes, learning, like just constant learning.
36:55Bill Gurley:That's so cool. Which I think is, that's the second principle of my book is continuous learning, but it ties in with the first one. The best test as to whether you found your passion is does the learning feel like free? Like, would you do it instead of watching a TV show? Like, is it something you enjoy so much that continuous learning is just you enjoying life? you know and if you find that you you found you found it you found your passion a quick aside i've
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38:42Chris Williamson:Joe Hudson's got this line, enjoyment is efficiency, he says. I liked it. I think it's really, really true. Yeah. People have this relationship between discipline, motivation, and obsession. Discipline's always there, but there's a lot of friction. Motivation, the friction gets removed a little bit, but it's sort of harder to grab a hold of. You don't really know where it comes from. Maybe it's a rock playlist or maybe the right amount of caffeine or something. And obsession is friction inverted, as opposed to you having to push through resistance. the resistance pulls you toward it. That's exactly right.
39:17Chris Williamson:And the problem, I think, or the reason that obsession is difficult is that obviously if it's pointed in a non-positive direction, that's how you become obsessed with politics or porn or your toxic ex or something. But if it's pointed in the right direction, what from the outside looks like a superhuman amount of discipline from the inside feels almost like you haven't chosen it. I'm not choosing to do this thing. You know, I mentioned before we got started, there's not been a single house I've lived in for a decade that I've not turned one of the bedrooms, including most of the ones that I slept in, into a podcast studio for a decade.
39:55Chris Williamson:My house back in the UK has got a podcast studio in it. The one that I live in right now is still podcasting eight years in a thousand episodes. Every single house has had every Airbnb that I've stayed in. I get there and I fuck, I'm researching hotels to see if the depth of the table can withstand my MacBook, the stand and the a fucking tripod because that's what i want to do that's what i want to do i want to have these conversations so okay i i my entire life gets warped around it i'm sure you'll be familiar with the uh single ordinating principle i think bezos has got one and i think musk's got one and bezos's was always does this make the customer experience better yeah so everything every single decision in amazon was threaded through this sort of single eye needle and uh but Musk says, does this get us closer to Mars?
40:45Chris Williamson:Does this get us closer?
40:46Bill Gurley:And by the way, both of those people did something that is super extraordinary, which is they took an innovative company, grew it to hundreds of thousands of employees, and kept it innovative. It's two of the only examples I know of.
41:03Chris Williamson:They didn't get laden down with diseconomies of communication, lumbering fucking behemoth bullshit.
41:09Bill Gurley:That always lands in big companies. And it must be some heuristic, like the one you described, that allows them. In fact, I was just listening to Elon on Cheeky Pine, I think.
41:23Chris Williamson:With Dwakash. Yeah, this came up.
41:25Bill Gurley:This came up. Like every leader wants to know how he does it. That's why I think Collison was asking him, like, how do you lead? He goes, well, I'm down deep. You can't be deep. There's 200 ,000 employees. and Elon jokes, yeah, there's 200 ,000 employees. You have to have some heuristic, simplifying heuristic that can spread through their brain. Or else just spinning too many plates. Yeah, exactly. Yeah, yeah. It's pretty impressive. It's super impressive.
41:54Chris Williamson:Okay, so career pivot fear. Yes. Someone is in the career, not super fired up. I used to be, and it just feels like it's time for me to grow now. What are the indicators that it's time to move? And what are the things that they should keep in mind to maximize their bravery, give them a little exogenous amount of morale?
42:22Bill Gurley:So on the do you know, I mean, I love this test of do you see yourself doing this 30 years from now? Because if the answer to that is no, you should get busy. What's the line from Shawshank? Get busy living or get busy dying. If you know that's true, well, now is when you should start. I'm not saying quit tomorrow, but start building the plan. And then there's all kinds of things you can do. In Designing Your Life, Dave Evans has this exercise where he says, create three to five scenarios and battle card them of what you might do next. Fill them out. AI can really help, right? You could build a 20-pager on each one of these career paths.
43:07Bill Gurley:What might I like? What might I not like? What are the three things people love in this career? What are the three things? You can steer it at all, right? You can ask people in those fields. You can go find them. So you could role play being in each of these. There's a heuristic in the book that I borrowed from Ben Gilbert at Acquired, a lot of podcasters, where he had side hustles at all his jobs. So at each job he went to, he would ask the employer, if I do it on my own time, can I do this other thing also? And there's something really great about that. One, in each of his cases, he ended up doing something pretty remarkable in the side hustle.
43:48Bill Gurley:At Microsoft, he created Microsoft Garage, which became this way for Microsoft to stay relevant with founders. And he met all these founders. Like all this kind of extra goodies came from that. Um, but I think it all, like, so you learn more, you learn maybe two, you get two shots on goal instead of one. And I think the employer makes you look proactive. So it reflects positively on you. When he ended up at, at Madrona VC, ask him if he could start a podcast and look where that led. And, um, I just had dinner with both of them and, uh, they were in Austin and man, they're happy. Like I got to tell you, like they are really happy people.
44:29Bill Gurley:So similar to you and your obsession and, and they fell into it through that, through getting there through that way. So I think those are some things you can do to, uh, to test. And then look, what are you doing in your spare time? Like, are there any signals there? Um, those are all great ways. I wouldn't quit if you don't know where you're going. That doesn't make any sense.
44:51Chris Williamson:Yeah. Yeah. Yeah. It's such a good shout to say, sort of what are you thinking about in the shower?
44:57Bill Gurley:Yes.
44:57Chris Williamson:What are you doing in your spare time? I keep on fucking watching pickleball drills. I just keep on thinking about pickleball and I'm really interested in the sport and I'm interested in how it's growing and I love playing it with my friends. But even when I'm not playing it, I'm always thinking about it a lot. Maybe there's something going on there.
45:15Bill Gurley:Let me share this fun story I just stumbled on because I'm using some hacker techniques to promote the book, and that led me to talk to this gentleman. And when I pinged him, he said, oh, please send me the book. He goes, I saw the video a long time ago, and it changed my life. And I said, well, tell me that story. And he was a real estate lawyer, and he loved football, and he loved offensive plays and offensive diagrams in football. I love this story because it fits with my thesis that the best stories are in jobs your parents would tell you to never go do. He launches a website to help people like manage and develop football plays.
46:02Bill Gurley:And then he builds software and then he starts a podcast. He has 900 ,000 followers and this is what he does all day now. He talks about offensive football plays with the best and the brightest in the field. He's known throughout the industry. What a great story. Like how awesome is that? It's brilliant. It's so great. Like, I think people don't realize that you can actually, there are careers in a lot of places. A lot of people want to be in Hollywood or music and they think they can't do it because they're not talented. But there's a hundred support jobs for every artist that's out there. And there's tons of work to go do.
46:42Bill Gurley:You know, if you really love being around that stuff, there's tons of opportunity.
46:46Chris Williamson:Especially given that you can fail at a job that you hate. You can underperform in an industry that you don't want to be in. So the prospect of potentially doing okay at one that you love is infinitely better. I think so. I think so.
47:04Bill Gurley:That goes back to life is a use it or lose it proposition. Like, give it a go. And then the other thing to know about failing in that is humans are, like, the research in psychology says humans are really good at forgiving themselves. Like, you're not, the failure's not going to, you're not going to ruminate on it forever.
47:25Chris Williamson:Especially if you tell yourself, well, I'm proud of the bravery to make the call. No doubt. Isn't there some evidence from psychology that humans prefer just making decisions generally? That if you make a decision, you tend to be happier. Let's say it's maybe a slightly less momentous decision between one city and another. The city that you're in now are moving. On average, people that move are happier. And I think part of that is just, well, life is like novelty and variety are pretty fun. it's different and exciting. And even if it's objectively a little worse, subjectively, it's all new.
48:06Bill Gurley:Yes. I liked it. I liked it. I just had a similar life experience. I spent 25 years in the Bay Area living in one type of community. And when I moved to Austin, I moved downtown in a high-rise, completely different repot. And it's invigorating. Like, it's awesome. New place for coffee, new place to work, to take your calls, your morning walk.
48:27Chris Williamson:all that's different. That's great. I agree with that sentiment. So you quit a successful job at Compaq to start again. How do people know when they're plateauing versus they're just a bit bored or something?
48:43Bill Gurley:Yeah. A few people have asked me this question. Once again, I think the 30-year forward exercise gets you away from that because it's asking a different question. One thing I'm really big on is, and there's a different chapter dedicated to this, is developing peer relationships. And we can go into why I think that's such a huge unlock. But one of the benefits of having a group of peers, especially if they're outside your organization, so these are people on the same career path you're on, but are maybe a bit distant, They're at a different company or whatever. And if you have a community like that, that you really trust and support one another, they can help you with that question you just asked.
49:33Bill Gurley:Like, am I failing and I'm never going to succeed because I don't have the right talent for it? Do I maybe have a shitty boss? Is their experience different? It's a great group of people to ask those questions of.
49:48Chris Williamson:It's almost like being able to run a little split test of yourself. Yes. What are the things that are different in your experience and how much of those are fundamental to the role? Exactly. Yeah. And how much of that is transient that I could just finesse my way out of.
50:06Bill Gurley:There's 10 other reasons why you should build that group, but it's good at helping with that problem that you just described.
50:12Chris Williamson:How do you deliberately upgrade your peer group without it being transactional? How can you make like-minded friends and peers without them thinking that you're constantly just wanting something?
50:25Bill Gurley:Yeah, it's a tough question because I think the number one reason people are bad at forming these peer groups is they've been taught to be a climber and they've been taught to almost been taught to be a bit sharp elbowed and to outgun the next person.
50:42Chris Williamson:Zero summy.
50:43Bill Gurley:Yeah. And we borrow a lot of our mental frameworks from finite games that have a beginning and an end in a single winner. And careers just aren't that way. Almost any industry, if it's not downhill skiing, there's lots of winners. You know, there's tons of winners. Podcasting is a great example of that. There's tons of winners in Austin. And so if you can build a peer network of like-minded people that you trust, and the great test of do you trust, would you share your best ideas with them? Like that you've learned this new thing that you just unlocked in your job, would you share it with them?
51:24Bill Gurley:You should actually, I believe, but a lot of people wouldn't. And so once you get to that place, it's a really special place. There's a story in the book about Chris Del Conte, who's the athletic director here at the University of Texas. And when he broke into sports administration, he was in the development office. He went to a conference, and it's a great place to meet peers. He went to a conference and met with a couple of other young men who were also at the beginning of their career. They exchanged numbers and started a text group. And over time, they added a few more people to that. got up to like seven, seven or eight.
52:04Bill Gurley:They're all eight, all eight of them are D1 athletic directors now. And they all started on the bottom. And if you follow them along that journey, they're learning elevated each time. Each year they met, each time they texted the problems they were encountering, they were sharing, they were explaining. It got to the point where they would do weekends away with their wives and invite in guests. You know, you talk about external learning. Who's holding many conferences on their own nickel and bringing in external guests to help educate them so that they could rise and thrive together? It's just so, I just like, I get like, there's another story that's perhaps more modern for the younger crowd.
52:53Bill Gurley:Mr. Beast did this when he was 17. He found three other people that were trying to hack YouTube. They were basically trying to figure out the game of YouTube, and they were on a Skype call for 16 hours a day together. And he says if there were a fifth person in that room, they would have made a million dollars also. Like, it was just because the stuff they were uncovering was so usable and just deterministic, just no one else knew it. And he used a phrase I love. He said, you know how they talk about 10 ,000 hours referring to the Malcolm Gladwell book. He says we got 40 ,000 hours because we were sharing it all.
53:30Bill Gurley:That's not the exact math, but it's a cool reflection of the moment.
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54:42Chris Williamson:That's L-I-V-E-M-O-M-E-N-T-O-U-S dot com slash modernwisdom and modernwisdom at checkout. What do you think about mentors? You know, peers are great. They're struggling with the same challenges you're sharing and sort of going on the journey together. That feels cool. It's like a teammate. But presumably there's a good argument to be made. Well, maybe you aim for someone that's already been through the pitfalls. How do you come to think about the role of pitfalls?
55:09Bill Gurley:I think you do both. They serve very different purposes. The co-learning journey, I mean, Peers give you co-learning. They give you support, which I talked about. They give you reflections. You can ask those questions. Is this the same in your job? You're vulnerable with peers. You wouldn't do that with a mentor, right? Especially if you get the peer group in the right place. You tell them, I'm struggling here. So I think it's just a different purpose. I think mentors are extremely important. but I think the idyllic version of a mentor is a bit broken because we encourage a lot of young people to cold call too high where the rejection rate's going to be 98%.
55:55Bill Gurley:Because the CFO of this company doesn't want to be friends with you. Exactly. But it happens constantly. And so what I encourage people to do is divide mentorship into two different categories. Have aspirational mentors. And just like that file folder for your dream job, create one for each of them. Like study them like a kid might study Star Wars characters or something. You know what I'm saying? Like really get enamored with these people that you idolize as aspirational mentors. And one, you're going to learn a lot studying them. And by the way, the resources are amazing right now. YouTube interviews, podcasts, like AI, you can learn faster than you ever could have learned before.
56:41Bill Gurley:So study them. If you ever meet them one day, the fact that you studied them this long is going to prove super useful. And then for the mentors you actually want guidance from, like tone it down a bit, like go two levels below what you thought you were supposed to do. And you're going to meet somebody who's so thrilled that you recognize that they were successful and worthy of giving advice that your hit rate is going to go up 10x or more like the probability that you're going to get them to do the work is so much better like i noticed that
57:16Chris Williamson:when i first started the show in 2018 in still not early it felt late but you know now it feels early ish it was so flattering for people to be invited on a podcast you know one of the other things this is such a funny trick that I still use now. So the world can have this one. I realized that flattery was one of the big drivers, I think, for bringing people on the podcast, especially, no one knows who it is. It's this random British guy asking me if you should come on. I always used to ask people, can you please put me in touch with whoever handles your podcast adverts? And it's some small researcher at fucking University of Arizona.
58:03Chris Williamson:And they're like, oh, well, it's just me that handles my podcast. I'm seen in the echelons of those that would have an assistant or perhaps a receptionist that would handle my podcast ads. I get it. And that's still now. Please pass me on to whoever handles your podcast ads. And that's actually another good one, I think, just generally for any outreach to somebody. You want to be in front of the right person, and especially if you're starting to pitch up toward mentors, that right person who actually handles that thing might not be them. So, uh, you know, reaching out, you please put me in touch with whoever handles bills, uh, inquiries for coffee or whatever it might be to the admin inbox, because the last thing that you want is some complex question that the person who handles the inbound open email thing or the LinkedIn, you know, the, the LinkedIn DM requests, is it them?
58:51Chris Williamson:Or is it going to be somebody else looking to get put in touch with the person who handles their partnerships or the, whatever it is. If it is them, they feel flattered. And if it's not them, the delegate person passes
59:02Bill Gurley:you on to the right department. And, and this isn't in the book, but if you ever meet the delegate person, pay as much attention to them as you possibly can. Like learn all you can about them. Like, like be generous and kind and thoughtful.
59:24Chris Williamson:It will pay off big time. Good story around that from the show. David Goggins. You familiar with David Goggins? I'm not. Okay, so he, ex-Navy SEAL, endurance athlete, probably one of the most sought-after podcast guests on the planet. In the last probably six years, he's done two podcasts. One of them was mine, and the other was Rogan. He brought a brand new book out. His first book sold gazillion copies, brings a new book out. and for nine months, I'm back and forth with a person on his team and checking in, seeing how everything's going, seeing the marketing, this, this, this, this, this. And then he canceled every other podcast appearance except for Rogan.
1:00:07Chris Williamson:And they tried to cancel the one with me as well. And I got this message, really sorry, David's just gonna have to, we're not gonna be able to make it work. And I was like, look, I will do whatever it takes. I'll move heaven and earth. I'll come to you, I'll bring you to me, we'll change the date, we'll do whatever it is. And they said, a couple of days later, I got another reply. Okay, we're in, we'll be able to make it work. And when I turned up, David, he's sort of stern, stern, hard guy, comes up, very nice to meet you. The first thing he says after that is, I just want you to know the only reason that I'm here is because of her, and pointed to the person that I'd been emailing.
1:00:47Chris Williamson:Yep. Precisely.
1:00:53Chris Williamson:So in your framework, loving the grind is sort of a non-negotiable. Yeah. Can someone sort of learn to love grinding or is that innate?
1:01:04Bill Gurley:I don't think so. But, you know, when you were talking about your love of podcasting, you know, the word that popped into my brain and there's a book by this title was Flow. and I just find people that are truly tilting against their passion, they never even think about it as work. And at times, the experience does go into this flow thing, like where when you're done, you don't even remember doing it. Like you're just that much enamored with the whole thing. And because I've felt that and I've seen it, I just, I really don't know how you could do that. I suspect some human is just wired in a certain way where they might be able to do it.
1:01:55Bill Gurley:But I don't know that most humans could. Like, and I don't know. I do think we get a lot of young people to do it for an extended period of time. And, and. The meat grinder thing. Yeah, I meet some, I just yesterday met with five of the top. I helped start this robotics honors program at Texas, and I met with five of them. And they're giving you their background, Eagle Scout, and it's 1580 SAT. Clearly, this human's been programmed to go take the hill on every single thing they do. But I don't think that's the path to greatness. You know what I'm saying? I just don't think just being good at the grind is what it takes to be truly exceptional.
1:02:47Chris Williamson:Brute forcing creativity, sort of white knuckling your way through miserable successes, it lasts for a good while and might be sort of the activation energy you need to overcome some discomfort at the start. But I would agree, I think. Like maybe if you're just so damn competitive, like winning all the time. Winning is your passion. It's a meta passion. That's possible. Yeah, that's interesting. And that's certainly some people, right? They just want to win.
1:03:15Bill Gurley:Yes. I think Michael Jordan would be a good example of this.
1:03:19Chris Williamson:Have you heard Novak Djokovic's interview where he's asked, why are you so good at tennis? And he says, I just like hitting the ball. I love that. Yeah. Um, whereas, you know, Jordan invented rivalries. Yeah. He invented slights against himself. There was, was it 92 or 93? Very driven human being. He wins some, I think it's his induction into the hall of fame. And during that speech, this, this is the moment that you've worked at supposedly your entire career for.
1:03:49Bill Gurley:He takes a shot at somebody, right?
1:03:51Chris Williamson:He spends the entire speech just revealing all of the slights that from his past and this person and this person, they couldn't believe that. You're even at the moment where you've broken through escape velocity. You're out in space. I don't love that much. It's not the energy that I have. Yeah.
1:04:18Bill Gurley:There's a counterexample to that. There's this thing you can find on YouTube where Shaq was on that famous show that he does with Kenny and Charles and Ernie. And Inside the NBA, I think it's called. He's at the All-Star thing, and there's all these legends there. And he just kind of goes off on his own talking. And he talks for like five minutes, and they don't interrupt him. and he's telling his story of how he made it and all the people that influenced him along the way and how he views all these legends as idols. And he just goes on. He's just thoughtful, like gracious for four or five minutes.
1:05:03Bill Gurley:And Ernie's crying by the time he's done. And I love watching it. I've watched it probably 10 times. I just love the notion that you carry that much thankfulness for the others that helped you get where you are. And I think in conveying that, it makes him look like remarkable. It really does. Like that his brain's wired that way. I felt very proud of him. I have no reason to be proud of him. And he probably couldn't care less that I am proud of him. But I like that. I like that version better.
1:05:44Chris Williamson:It feels much more pro-social. Yes. I suppose the problem is ultimately what matters is performance, especially in an industry like that. You know, if Michael Jordan was some middling or pretty poor quality basketball player calling out all of these people and inventing random rivalries to try and motivate himself to go, people would look and say, you're just bitter. And the same thing with Shaq. If Shaq, who had a version of him that hadn't achieved all of that, was proselytizing about these wonderful people and how grateful, he would be called a suck-up. And this is... That's fair. The medium is the message, but the medal is the message very much for this stuff.
1:06:34Bill Gurley:Well, and look, that is more of a finite game, right? Like that is, and I did use downhill skiing, but there are like those kinds of competitive sports. You may need to be sharp elbow to climb to the top.
1:06:45Chris Williamson:If you're an author, the same thing is not true.
1:06:48Bill Gurley:That's right. That's my main point. And most of the careers, most of us chase, that's not, that's not a reality. Um, but, but I also have a principle always give back, which is why I, I feel warmly about the Shaq thing, which is I think that the minute you move from the first rung to the second rung of the ladder, if you take the time to appreciate the people that helped you with that movement, you will develop a process that you will feel really good about at the end of your life. And your network of supporters will grow faster. You'll have more friends in your corner.
1:07:27Chris Williamson:You're seen as the pro-social hub as opposed to the person that stepped on a bunch as they come up. Yeah, you'll be able to weather the bad times and enjoy the good times more. Yes. So you talk about honing your craft. Kind of interested in what that looks like in knowledge work when there's no clear scoreboard.
1:07:47Bill Gurley:Well, here's what I would say is, and I think this relates to this college grind. I think some of these kids are so burned out by the time they get to the end of their senior year in college that they can't wait to not study anymore. Like they view it as, okay, 12 years plus four, 16, I'm done. And they're looking for a break from studying. And the best in their field, like Danny Meyer, are studying all the time. And so that's a weird contrast. And there are fields where continuous learning is somewhat required. The medical profession is one where that happens. And obviously, there are fields like ballet where if someone says they work 16 hours a week or a day, we all applaud it, which is weird.
1:08:42Bill Gurley:Because if you said that about an engineering career, they'd say, you're a bad human, you know, but whatever. So this notion of learning constantly in your spare time, I think it's just the best test of whether you're truly obsessed with what you're doing.
1:08:59Chris Williamson:Do you remember when Elon took over X and he did that announcement post and he said, we are looking for people who want to work on the hardest problems possible as long as they can at an unrelenting pace to try and change the world. And there was a lot of quote tweets of this saying, we're throwing it back to a version of work-life balance that is completely primitive. This is abuse. This is horrendous and all the rest of it. And don't get me wrong, there are certainly some bosses and some industries that will drive their employees so hard that it's irresponsible. But if you're stating it up front, what all of those people that quote tweeted it and complained about Elon's horrendous working conditions failed to understand is there are people out there to whom that sounds like a dream.
1:09:53Chris Williamson:they want to work 18 hours a day fueled exclusively on high quality stimulants and
1:10:01Bill Gurley:chick-fil-a especially if they get to hang around with the smartest people and they want to be
1:10:06Chris Williamson:pushing each other and they want they want to send it they want to send the living shit out of it you
1:10:10Bill Gurley:know who's doing that right now which is super interesting the young ai founders they've embraced this meme from China 996. It actually was developed in China, which means 9 a.m. to 9 p.m. six days a week. That's what it stands for. But they used the phrase. And Silicon Valley got lazy in COVID. So you have the situation where the broader culture had moved from being formerly a bit workaholic to being lazy. And despite the fact, you know, they literally aren't coming into the office. You can go in downtown San Francisco and look through buildings, you know, because there's so much cubicle space with no one there.
1:10:53Bill Gurley:And these young kids in this AI world are the ones you're talking about that want that experience. Do with some examples of those. I think almost all of, I'm serious, almost all of the AI companies in San Francisco have this mindset, especially if they have a young founder, like a 20, 22, which is there, but it, it, it, the, I'm agreeing with you. Like this notion that, okay, you don't like it because you don't think there's work-life balance. Do you think it should be illegal for them to do it? Like, like, like I don't, they get to choose their own life.
1:11:32Chris Williamson:It's kind of the argument for drug legalization, but it's workload legalization. Exactly. If you're doing it and it doesn't hurt anybody else, you do to your workload as you wish.
1:11:40Bill Gurley:But I would say this, you do need to recognize that you might one day be competing with someone that has that mindset. Absolutely. And that's where I go back to do what you love. Because if you're sitting next to that person.
1:11:57Chris Williamson:And you're white knuckling it and they're loving every moment.
1:11:59Bill Gurley:Yeah, you're probably going to lose. Because they're at home learning in those extra hours stuff you're not. Like there's no way to keep up.
1:12:08Chris Williamson:Yeah, well, it is, even if every small, if every iteration of you doing a thing degrades your willpower, drive, whatever, even by the tiniest, tiniest, tiniest amount, it is just a single direction trajectory from you to crash land into burnout. Well, and the gap is going to grow.
1:12:30Bill Gurley:And I'll tell you one other thing which I stumbled upon, which I think is an interesting juxtaposition. If you're a grinder, if you followed the path you were told to follow, you went to the school you were told to go to, you got in the program you were told to go to, you became certified as an accountant or an engineer, whatever this thing is you did, but you don't love it. You're in that place you were talking about. I suspect for those people, AI scares the living shit out of them. Like they view AI as - Grind versus grind. It's going to crush me. I'm going to lose my job. Look at this world.
1:13:08Bill Gurley:It's unfair. Now, if you contrast that with someone who is a proactive, independent climber who's trying to build their craft, their world, their continuous learner, for that person, AI is a jetpack. Like they can now do more things faster than they wanted to do, and they can achieve more than they were able to before. They get to run extra fast. Like, so two people maybe in a same station in life, AI looks like the opposite to them.
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1:14:55Chris Williamson:That's timeline.com slash modern wisdom. Can I read you an essay that I wrote? Sure. Cool. So guidance doesn't sculpt us into something new. It exaggerates who we were already. The pattern is almost cruel. The ones who least need the medicine are the ones most likely to overdose on it, while the ones who need it desperately are immune. Advice doesn't land evenly. It finds the path of least resistance and tends to be absorbed by people who already lean in its direction. So I first started thinking about this when considering the post-MeToo instruction of don't be pushy with women. And I realized that it made conscientious, anxious guys even more timid, while the dudes that were blowing through boundaries just didn't take heed.
1:15:36Chris Williamson:Exactly. Or another example of the prescription to just work harder, that gets devoured by the insecure overachiever, who's already bleeding effort into every crack of their day, while the genuinely lazy person just coasts past it unchanged. The call to take more responsibility, encourages the one who always thinks that it's their fault to carry even more of the load, while the ones who constantly point the finger elsewhere never change. There's a bunch of reasons. People filter it through their existing traits. It amplifies predisposition instead of correcting overbalance. We all want to be good, so we sort of over-index guidance that flatters our self-image.
1:16:11Chris Williamson:But I think the most influential one is that the pieces of advice that match our inner fears are the ones that we believe the most. So an anxious man doesn't just hear, don't be pushy. He feels that it confirms the fear. Any move he makes is already too much. The sensitive man doesn't just hear open up more. He feels it confirms the worry that he's emotionally inadequate, even when he's already oversharing. And for what we're talking about, the insecure overachiever doesn't just hear work harder. They feel it confirms the suspicion that they're never enough, regardless of how hard they try. And this to me, the, um, disproportionate way that advice, you could call them advice hyper responders, right?
1:16:54Chris Williamson:The same piece of advice goes in very different directions to two different people. I do still think that developing a grind capacity is important. But if you don't have the passion part, if you don't actually care about it, you can drive really, really fast in a direction you don't want to go. And that's the problem that you will look back on a career where you white knuckled a shit ton
1:17:21Chris Williamson:of lauded but largely unfulfilling wins.
1:17:27Bill Gurley:Yeah. And look, I'm somebody that, I don't think you feel this if you switch jobs at three years, but when you reach a true retirement, and I'll be 60 next year, and when I decided that, okay, I loved every minute of being a venture capitalist, but it's time for me to pass it on to the next generation and move out of the way, it's reflective. Like, oh, shit, I'm there. And I think it's hard when you're 25. I think when you're—one of the benefits of being 18 is you don't see the end of times at all. And that gives you all kind of superpowers to play. um there's some point at which you realize there's an end to all of this and for this particular thing about your career i think the sooner you can feel that the better just because if you do want
1:18:32Chris Williamson:a different at bat like you want to front load that fear a little bit yeah if you can i don't
1:18:38Bill Gurley:know if everybody can.
1:18:40Chris Williamson:Um, well, I certainly know that the regret minimization thing, there's a variety of different exercises that are on George, my housemate. He did this. He did this six years ago. I remember him telling me about this six years ago and I thought it was insane. I kind of still think it's insane now, but I know he still does it. I think it's one morning a month. he's got a reminder on his phone he wakes up he lies in bed and he imagines what it would be like to have no arms or legs viscerally thinks about what it would be like to have no arms or legs for 30 minutes to be grateful is that to to and then to be reborn into this body yes with the arms and the legs.
1:19:26Chris Williamson:So I've been, I've been really pushing hard over the last 18 months, uh, on emotional work, um, trying to get below the neck as I've said. And, uh, I think a big part of it is this, that how many smart people who know all of the insight, they could do an expected value calculation about the likelihood of the success and what is the objective quantifiable, uh, utility of enjoyment versus, but then you've got hidden and observable problem coming through again. But ultimately, what that strategy from George is trying to do, what your regret minimization thing is trying to do, is not really front load more information.
1:20:08Chris Williamson:It's trying to overload emotion. It's like, oh my God, there's a great fucking workbook from Tony Robbins, Unleash the Giant Within, but it's this weird 1994 four audible workbook and it's only an hour and a half long i can't even find it listen i've got it in my audible george's got it in his a couple of our friends that we've sent it to i can't even find it publicly i don't know what fucking it's your hacker friends that have got us under the back and in it he's got this thing where he says imagine what it's cost you in the past imagine what it's costing you now imagine what it will cost you in the future he wants you to overload the pain.
1:20:47Chris Williamson:It's like feel as much of it as possible. All of the rumination and the grief and the wistfulness and everything that from what's happened. And right now, how is it affecting you? How is it limiting your time? How is it stopping your happiness and the future? What is it going to do to you? What's life going to be like if nothing changes for a decade, for two decades, three decades? What are you going to be like? What are your relationships is going to be like the quality of your mind, your health, everything. And then imagine what life could be like if you changed. And he's trying to get you to oscillate between this pain, pleasure principle.
1:21:21Chris Williamson:And I've had to make some, I moved from the UK, I was 32 years, 33, nearly 33 years old with a successful career in the UK, running nightclubs, one of the biggest events companies in the North of England. And it's something I dedicated 15 years of my life to. COVID had just happened and nightclubs were just reopening. The clubs reopened and I didn't want to go back. I just wanted to do the podcast.
1:21:45Bill Gurley:And that was the exercise that you went through. And I presume zero regrets about the movie.
1:21:52Chris Williamson:The best single decision that I ever made in my entire life. But even with that, going back, I don't have the borrowed authority of my fears from back then. So this is a great idea from Morgan. you should i'll send you this once we're done this wonderful blog post he talks about nostalgia and about how we we sort of were unable to see the pains from the past especially when we've moved on we don't see our fears from the past particularly well so him and his wife are talking about when they used to live in new york and they were in their 20s before they had kids and he's saying to his wife wasn't it so wonderful we used to wake up on a saturday we could lie in bed we'd get a coffee we could just walk around we had no response but we were just kids it was so beautiful his wife goes what are you talking about you were miserable you had no idea if your career was going to work we constantly had money problems we didn't know if we were going to make it you were worried about where your future was going and we did it and morgan realized that in retrospect all of his fears that were a waste of time he knows were a waste of time he didn't need to worry So what he sees is how he should have felt knowing how well life was going to go.
1:23:07Chris Williamson:So this, it's the same reason that no one ever believes we're living through a golden era. Golden eras only exist in our memory. And, uh, all of that together, you know, I can't see, I know that I had the fear. I've got the fucking journal. I've got the journals on my Apple notes still of what if I do this thing and it goes wrong and everyone's going to laugh at me and I'm going to have to come back and live in my mom and dad's spare room and I'm going to have a gluten intolerance and a club foot under a bridge and it's all going to be. And yeah, I had it have not gone well. Maybe that would have been the case, but that is the worst possible scenario.
1:23:42Chris Williamson:And there were a million, there's gradations between the best one and the worst one. Uh, but yeah, I, I, uh, I'm really proud of making that decision, but I, even that the best single decision I ever made in my life, I still had to apply a fucking galactic volume of pain and the same amount of pleasure in a desperate attempt to galvanize me to do it so yeah even even decisions which in retrospect feel very obvious i think at the time require the inhuman amounts of motivation to go to get the activation energy
1:24:19Bill Gurley:i get you moving i like the battle card notion i mean it's similar to some of the designing your life stuff, but like allowing yourself to fully imagine the other reality, you know, and, and, and without the comparison, like while you're, while you're doing it, like really imagine every element of it and on its own, and then maybe go back and do the one you have and then battle card. I love that idea. I think one of the reasons I was a, uh, useful venture capitalist and, um, One of the reasons this regret minimization thing worked for me is I think I'm very good at bringing forward the future in my brain.
1:25:02Bill Gurley:Like extrapolating back, if you will. Almost like a life NPV kind of thing. Yeah, yeah, yeah. Just able to do that.
1:25:11Chris Williamson:It's like reverse time travel.
1:25:12Bill Gurley:Yes. And it makes those exercises work better. You know, the fact that I somehow can do that in my brain.
1:25:20Chris Williamson:um so speaking of that you're a very successful investor what were you looking for in the founders that you invested in what were the traits what was the global yeah decision framework and
1:25:34Bill Gurley:and a lot of vcs say the same things over and over so i'm a little hesitant but i'll do it anyway um the one that took me the longest to fully recognize is how important product product instincts are. So that's critical. Like, like new, most of these companies are riding some new wave, like this AI wave and the product surfaces of the new thing aren't as well understood as the ones of the old thing. Think about the mobile movement. So you're predicting. And you need instinct to get that right. Like you just need instinct about humans and how humans like to interface with things and a whole bunch of stuff.
1:26:15Bill Gurley:So product's a big one. Salesmanship is a huge one that people probably don't think about enough. But if you're a founder, you're selling to new investors. You're selling to employees. You own the company culture and the perception of the company. You're striking deals. You're selling to customers. You're just out selling all. You're the number one sale, you're the chief salesperson for your company. And if you're no good at it, you will struggle. So that's another one. Determinism, you know, and it kind of goes back to everything we're talking about with chasing your dreams. But, you know, Josh Wolf at Lux Capital says chips on shoulders, put chips in pockets.
1:27:00Bill Gurley:And like someone that maybe failed a couple times got a point to prove oh man you want to feel that like you want to feel that they're never going to give up a bit of grit yes like not a bit like you want you want top one percentile yeah you want to be afraid a little bit about how determined they are you know what was that line
1:27:27Chris Williamson:uh is this person going to do this no matter what was that bezos bezos i i asked bezos you found
1:27:33Bill Gurley:that. I asked Bezos once how he could be such a successful angel investor because he's running the largest employment account company in the world. There's other shit to do. Yeah, exactly.
1:27:45Chris Williamson:He has less time than you to scrutinize.
1:27:47Bill Gurley:No, way less. And he said the only thing he looked for is the determinism. Is this person going to do this no matter what? And all of his questions. And that's so cool. All of his questions were around that one very thing.
1:27:59Chris Williamson:What if this? How would you approach that? How have you in the past done the gut over?
1:28:03Bill Gurley:Why are you doing it? What if this comes up? What if someone offered you this?
1:28:10Chris Williamson:I had a conversation with a friend a few years ago, and he gave this wonderful example of champions. He says, everybody looks at champions to try and find what they have that other people don't have, but they've got it completely backward. Champions miss something that normal people do have, which is an off switch.
1:28:29Bill Gurley:Yes.
1:28:30Chris Williamson:And when you're talking about a zero-sum game or a game that's more competitive around a world, you're looking for somebody who will go to unreasonable lengths. And I suppose this is why strong ethics, too, if you care about the ethics of the companies that you're going to invest in, because that chip on shoulder, that determinism.
1:28:51Bill Gurley:Could push you right across the line.
1:28:53Chris Williamson:Very, very.
1:28:54Bill Gurley:And a lot of these people live on the line. Yeah. It's just, it is what it is. When you said that, I couldn't help but, and it's horrible, the accident she had, but I couldn't help but think of Lindsey Vonn. Like, she had a— Who's that? Lindsey Vonn's a downhill skier that's 41, 42, and is in the Olympics right now. Okay. And, you know, she had retired a while back and came back, trained again. Her trial times were highly competitive. but early when she got to Italy she injured her ACL and she put on a brace and said I'm gonna compete anyway and unfortunately had an accident went to the hospitals had three surgeries snapped a shit yeah but but to be in your 40s and coming back in some ways somewhat injured and I'm like I'm going anyway I'm sending it anyway look I I didn't know about this story.
1:29:55Chris Williamson:This just happened like a week ago. I kind of like it. I kind of like it. What a way to go out. Yeah, okay. Yeah, fair enough. You're going to be laid up. Better to burn out than to fade away. Well, could you imagine, again, that is, and this is a fucking wonderful little microcosm of exactly what we were talking about. What about that open loop? Yeah. Would my ACL have held up?
1:30:16Bill Gurley:Yeah.
1:30:17Chris Williamson:Would it have held up? Am I going to go back at 45? No. I'm not going back at 45. No, no, it's the last shot. this is it.
1:30:23Bill Gurley:Yeah. So I kind of like it.
1:30:26Chris Williamson:Fair enough. I'm sure that her surgeon doesn't like it. Or maybe he does if he's paid well, but I'm sure her physio and her strength and conditioning coach don't like it. Yeah. Going back to the founder thing, is the founder more important than the company to you in some ways? Would you bet just on a founder that this person will find a thing?
1:30:45Bill Gurley:Well, here's one proof point that would speak to this is there are multiple companies that the original idea completely failed and the founder was able to pivot to something entirely new and be wildly successful. Slack is an example. It was a game company and the game failed, but they had built this tool to develop the game. I didn't know about that. It's so cute. Discord, who's one of our companies, was also a game company that failed and launched this Skype alternative for communicating during games that became wildly successful. And for any venture capitalist that's been through one of those pivots, they're famously known as pivots now, it's all about the person.
1:31:37Bill Gurley:Like, it's all about the founder. There's also a data point that most venture capitalists will quote, and I'm sure it's not scientific, but a new CEO hires a 50-50 bet at best. So why, if you're doing positive, like trying to run MPVs, would you even take the risk of hiring a CEO because you're going to, there's a 50-50 chance you'd just get a bad apple, in which case it's all toast. So, yeah, there's, and that lore goes beyond me. I mean, I think the founder mythology, if you will, is quite high in Silicon Valley for all those reasons. Now, there are times where you have no other option, and there's way more stories.
1:32:26Bill Gurley:This is kind of an odd fact, but companies that serve businesses have a much higher success rate of replacing the founder than companies that serve consumers. Why do you think that is? My best guess is consumers are more fickle and that product thing is just more artistic. It's like a taste again. Yes, more like a movie than a business. I love that idea. And business products are more systematic. You can algorithm that down to— Steve Jobs once said that the difference is the buyer in a business isn't the user. And he made that point. and that may be it. That may be the essence of it.
1:33:12Chris Williamson:That's cool. This thing, the beverage that you're drinking is mine and it's the first big company that hasn't been something that I've directly operated aggressively myself that I've founded. One of the interesting elements that I've seen with this, we did a raise last year, we raised$3.44 million and right now we're in the middle of raising$6.5 million. I'm watching Luke, who is one of the co-founders. Today, he drove from Portsmouth on the South Coast to Leeds, which is five and a half hours away, fucking forever away. Drove to Leeds for one investor meeting to just sit down with this guy. And when you think about, as you're sort of reeling off all of these different traits that you would have, sort of the obsession, the determinism.
1:34:03Chris Williamson:And, um, what's been cool is to see, you almost get to learn what people think of you when you do fundraising, when you're trying to get cash to inject into a business that's yours, you almost see in the responses from people. And, uh, a couple of times sent the deck out, this was in the first one. So we send this deck out and it's all sexy and it's got numbers and the projections and all the rest of it. One of my friends sent a reply to the deck and he made a meme. Have you seen the Midwit meme? Are you familiar with this? On the left-hand side is sort of a Neanderthal guy and on the right-hand side is a sage that looks like a Jedi.
1:34:42Chris Williamson:In the middle is a guy that overcomplicates everything and he's sort of screaming and getting. The joke is that the guy on the left and the guy on the right always agree. If it's going to the gym, it's lift weights, eat protein. Lift weights, eat protein. The guy in the middle, I must ensure that my scientifically accurate pre-digested way is consumed within a 30 minute and he replied with that meme and he said uh the guy in the middle said uh read the deck make expected value calculation check against finances and the guy on the left and the guy on the right said i bet on chris yeah i bet on chris i bet on chris and it was really interesting to see do people look at you or luke who's my guy or james who's one of the other co-founders do they look at you and go So I just, you'll make it work no matter what.
1:35:30Chris Williamson:And that was cool. It's the first time that I've experienced it.
1:35:32Bill Gurley:You can take that too far. I've met with founders who are anti-deck. I even wrote a blog post called In Defense of the Deck. Because they walk -
1:35:41Chris Williamson:Got to make sure that you don't misspell one of those words, but yes.
1:35:44Bill Gurley:They walk in the room and just want to chat. And you know nothing about the business. You know jack shit. And I don't want to learn about the business through a prompt with this human. Like, it's too hard. You can't get enough information fast enough through that. So I – and in this blog post, which I'd encourage people to find, I show Steve Jobs, Mark Benioff, Jeff Bezos in front of a deck. It's good enough for them.
1:36:13Chris Williamson:No, no, no. I don't disagree. I'm not advising people. People are prepared. If you're fucking investing in Nutonic, please scrutinize them.
1:36:18Bill Gurley:But I want to say one other thing about this because I think it gets more to the point of what you said. Most people perceive venture capitalists to be making investments the way maybe a buy-side public investor might be. If it's positive IRR and I'll make 14%, I'll do it. But venture capitalists have a limited number of boards they can go on, probably two a year. and so they don't have unlimited shots on goal. They can't fund everything that's over 12 % hurdle rate. They have to fall in love and it goes back to what we were saying with stories and all this stuff about people. Like they're going to pull the trigger because they have an emotional positive bias to go do this thing.
1:37:07Bill Gurley:And that taps in. It's about Chris for sure but they also need to kind of love the category and love the idea and want to spend 10 years working on the problem. Like all those things. Like it needs, they have to flip from zero to one in their own head, in this human's head. Does that make it harder for businesses that are less sexy?
1:37:31Chris Williamson:Of course.
1:37:34Bill Gurley:Unquestionably. That's why there's like these mid-market PE people. They go do those things. I don't even, I would never be motivated by it, but, but, you know, I'm not, not necessarily shitting on them too bad. Like somebody, there are, you can make money. There are things to be done, you know, but, but I also would say, and I think this is important. Um, um, there are businesses that shouldn't take venture capital and, um, a series A typically leads to a B and typically leads to a C and the ownership that a founder has can shrink pretty dramatically. And then the exit value, the exit value you need to make the same amount of money had you sold it a hundred percent on sweat equity is now 10 times higher.
1:38:24Bill Gurley:And just make sure you think through all that somehow through the use of these 19 credit cards and everything. The guy behind Tito's.
1:38:34Chris Williamson:100 of his and unbelievable do you know gym shark you familiar with gym no so it's uh probably one of the biggest british companies to activate i'm actually wearing the trousers right now and ben the the ceo and founder is a good friend and um it is a 2.6 billion pound wow company and And it is entirely private. And I think he's still got 75 % of it himself. It's a lot.
1:39:05Bill Gurley:But I would say even if you're going to sell for$20 million, there are far more companies that want to do a tuck-in$20 million acquisition than want to do a half a billion acquisition.
1:39:16Chris Williamson:What's the size of the market you're selling it to?
1:39:19Bill Gurley:Plus, if you're a large public company, you can do a$20 million acquisition without filing anything, without telling anybody. your boss won't care. If you own 100 % of a$20 million company, that's lifetime wealth. Like trying to make$20 million selling a company for half a billion, that's hard because it's hard to sell a company.
1:39:40Chris Williamson:Fewer people that can buy it. It's going to have more scrutiny that goes over the top of it. You've now diluted down.
1:39:45Bill Gurley:You need audited financials. You need like, they're going to have to file an essay. There's all this stuff. It gets really hard to sell a company.
1:39:55Chris Williamson:I don't ever think about the market of selling a company. You think about the market of the company that it sells to. Yes.
1:40:02Bill Gurley:That's so cool. Yes.
1:40:04Chris Williamson:Yes, it matters.
1:40:06Bill Gurley:It really matters. It really matters. And by the way, if you sell that first company for$20 million that you own 90 % of, and you want to go take the big shot and raise money, oh, great. Now you've got freedom, flexibility. You can take all the risk you want. Do it the second time.
1:40:23Chris Williamson:I've seen, I've heard a bunch of different horror stories about founders who've diluted down and diluted down and diluted down. And then before they know it, they're like, what the fuck am I working for? No doubt.
1:40:35Bill Gurley:Lickpref is a beast. What's that called? Liquidation preference. So venture capitalists typically take preferred stock and it has a term called liquidation preference, which means in a sale, they get the option to basically treat it like debt. They get paid out first. Wow. In a sale. and so if you've raised in these days these ai rounds if you raise 500 million like common doesn't even participate until you get a sale over that technically now it's often there are carve outs because they have to get something done but the bigger that number gets the more weighty it is
1:41:13Chris Williamson:yeah i mean i i feel fortunate when we did the first raise i bought back in i didn't want to dilute i threw more money in i threw more money in actually and by the way the investors love seeing that love love love seeing i i was like i am not in fact i gained i gained share of newtonic when we did the raise so i bought in a over the top of where i was already while we were diluting down hard to do it was i mean james james wanted a new porsche um and he was very gracious and we shifted some stuff around and i can't remember where else i took it that's awesome but no it was it was cool and um it's been really fun sort of learning about that world and now being able to see what's happening especially in the world of ai at the moment well that's a question what what are you most excited about with regards to the industry of ai and what do
1:42:08Bill Gurley:you think is overblown i would i mean be a little redundant but the thing i'm most excited about is just the personal empowerment. You know, there's all kind of anthropologists that will tell you we evolve with our tools. Humans, like, it's very clear, right? If I had a plow and a tractor and a computer and a chemistry set and the other guys, the guy in Naked and Afraid, like, I'm going to be more evolved than him. I can do more stuff. And this is the latest of those things. And And anyone that is a skeptic, and I've met a lot of like the top academicians that are skeptics and all this, you're no different than the Luddites with the looms in Europe.
1:42:58Bill Gurley:Like you're just not. It's the modern version of that. And the number one thing you can do to future-proof yourself is to run at it. Like to know whatever industry you're in, there is an edge of what is AI capable of in this industry. And you want to be right there. You want to be aware of exactly what that is. And if you are the most AI productive human in your field, you're not getting fired. You're the one they're asking all the questions of. Like what's this capable of? Um, and so I, I, in, in the, in the chapter I have on hone your craft, I say, study the history and study the edge. Like if you can quote from the founding fathers of your industry and you know exactly where the technological edge is, you look like a unicorn.
1:43:53Chris Williamson:You look. Going in the middle is where you die.
1:43:55Bill Gurley:Yeah. I mean, everybody knows the middle. Like I'm just talking about differentiating yourself. Of course. Of course. Yeah. So anyway, I, I find, I mean, I haven't, I, I, I'm anxious. This is also why I was a useful, I use the word useful, venture capitalist. I have FOMO about new shit that I don't understand. So up until at least a year or two ago, if there's an app in the app store in the top 10 I've never heard of, like hives, I have to know.
1:44:26Chris Williamson:You're allergic to ignorance.
1:44:27Bill Gurley:Yeah, I'm coming off of it a bit because I haven't done a claw bot yet, which I feel guilty about.
1:44:32Chris Williamson:Well, you can't get a fucking Mac Mini. That's why. You're not going to be able to buy them. They're all sold out. But I feel guilty about that. Yeah, yeah, yeah. You've got massive FOMO.
1:44:41Bill Gurley:Yes, but it's useful. And so anyway, I think that there – I would also say this about AI. If you're not leaning in, not only – people have said there's prompt engineering skills. Not only are you not learning that, but I find every day I think of a new way to use it and a new way to test what it's capable of. And if you're in it every day, you're helping to explore that boundary and you're all of a sudden learning new things. Do you understand what I'm saying? Like I had this great experience with the concluding chapter in the book. So my, you know, almost done wrapping up, feeling good. And the editor says, Bill, take a shot at the conclusion this weekend.
1:45:35Bill Gurley:So I spent six hours, seven hours. I sent him something. He's like, this sucks. Like first time, like it was really the first critical. He didn't use that phrase. Yeah, I really don't like this. So I asked ChatGPT in the pro version, the$200,$300 a month, whatever it is, write me a 20-page report on the best concluding chapters in nonfiction books of all time and give me a summary of each and what made it special. And in reading through that list, I noticed that eight or nine of the 10 took an orthogonal direction to the book, so it didn't summarize. It brought in a new perspective. And that gave me an idea.
1:46:18Bill Gurley:I then went and ideated on that concept and it gave me a new idea to take it in a different direction and what was the idea editor loved it huh what was the idea um the the not i all right i'll give this one away um the concluding chapter is titled it ain't easy and so the whole book is an exercise in trying to encourage you to go do this. And this is a little warning at the end. Like, it ain't easy. You got to struggle. You got to suffer. You got to be okay with failure.
1:46:56Chris Williamson:In praise of the grind.
1:46:58Bill Gurley:Yes. And the editor loved it.
1:47:00Chris Williamson:Good. I think that's an important message.
1:47:02Bill Gurley:Yeah. So if I don't have AI, I don't do that. Like, you know, and it didn't write it for me. It just gave me a new lens for how to think about it.
1:47:13Chris Williamson:When it comes to the AI thing, what do you think it's going to do to the field of work generally? What areas would you be worried that are going to be obsolete?
1:47:23Bill Gurley:Anything that was synthesizing. I mean, so the LLM, large language model, is really good at text. Really, really good at text manipulation. So if your job involved searching for text, summarizing text, anything like that, paralegals are already under threat. And I have talked to lawyers that have drastically reduced the size of their paralegal force. I've talked to them. That has already happened. Coding, it turns out, is highly structured text, more structured than text itself. right? If you think about it, it's got more. There's more rules. There's more freedom in actual language text than in coding.
1:48:14Bill Gurley:And that makes, and so coding's under threat. And the best people that will write or will generate the most code in the future are the ones that learn to be able to harness that tool the way a farmer learned to use a tractor instead of plowing. And that's your only choice. Like there's no hand hoers anymore. Like they don't exist. And so this text thing's a big deal. You know, if you translated something, that's a dangerous job. Someone needs to kind of make sure the translation's right, but that's a different job. It's more of a editor of translation, right? And that's an opportunity to move upstream.
1:49:01Bill Gurley:Be the one that's best at exercising that with this tool. But the old tool doesn't work. Like, it's not going to be real.
1:49:12Chris Williamson:If you were 21 and starting again with no knowledge or connections, what do you think you'd be focused on? What would you do?
1:49:20Bill Gurley:It would definitely be related to AI. I mean, it just would. Like, I'd be rolling around in it more. I would definitely have already launched 10 claw bots versus now where I don't have that need to see what's possible. I'm fascinated by the agent idea for a personal assistant like a running buddy. I just find that fascinating. Um, I, another one that I kind of am fascinated by, I think someone will build a new CRM from scratch that will be used by small companies that don't have a CRM because it's easier to start with zero in the database. And I think that will be super clever, that product that I don't think you can get there from Salesforce because you've got this huge database with all these fields and forms that no one wants to look at.
1:50:17Bill Gurley:And if you start with that as your construct, I think you'd build the wrong thing.
1:50:22Chris Williamson:Does that make sense? Because you're trying to backwards integrate something that's already a little janky.
1:50:28Bill Gurley:And I don't think the user wants to even see that stuff. That's interesting. And so it should, whatever the storage mechanism is, I don't think it will be visible to the user in the way that a database-type enterprise app historically did it.
1:50:47Chris Williamson:Mm-hmm.
1:50:48Bill Gurley:You know? So anyway, those are things that pop into my brain when you say that. Those are things I'd be playing with.
1:50:55Chris Williamson:I know that you're a big reader. What have been the books over the last couple of years that you have not been able to stop telling people about?
1:51:04Bill Gurley:Um, the second half of Range impacted me in a good way. David Epstein. Yeah.
1:51:11Chris Williamson:Yeah.
1:51:12Bill Gurley:And the book's known for being this antidote to Malcolm, although they're very close friends. In fact, Malcolm's quoted on the cover of Range, I think. But the book, people talk about this generalist versus specialist and this comparing of, you know, these two athletes. But he gets into a very different subject in the second half of the book. He gets into this notion, which I had always heard a phrase called far analogies, but he gets into this notion that people that switch industries or switch careers or switch academic focuses tend to be the biggest innovators of all time. And they come into something with a different mental model than the people that came up through the field.
1:52:01Bill Gurley:like if they enter through the side door. You understand? And it relates to the generalist. They see things differently. Yeah, yeah. And they're able to bring patterns or see patterns other people may not see. And I just find that fascinating. I touch on it in a couple of the chapters. In the learning chapter, in the peer chapter, I say if you make it far enough, you want to stretch the peer to someone that's maybe in a different industry. You want to stretch the learning to other industries. And it's where you find some of the biggest nuggets. It's more noisy. You're wading through.
1:52:40Chris Williamson:It's harder. Less aligned, right? Yeah, yeah. But the insights are power loss, step changes.
1:52:46Bill Gurley:It'd be like you listening to someone talk about great writing technique and get an idea for the podcast.
1:52:54Chris Williamson:you know well one of the things that i did about four years ago when i first moved to america was i got obsessed with cinematography and cinematography obviously there's cameras and videos and stuff here but we started doing this thing called the cinema series and this was shot like a movie and it culminated episode 1000 was me recreating the house from interstellar on a 85 foot video wall the biggest video wall in texas using the same technology that star wars uses yeah and we rendered the entire scene in unreal engine 5 and then did set dressing so we had live elements of dirt on the floor and cactuses and we reversed a fucking airstream in and i sat opposite mcconaughey and i sat him down 11th anniversary of interstellar and we were sat in front of the the house from from the movie and that was because oh i started learning about this and i started getting friends that were from the cinematography industry and i started asking them what would you do if you were trying to elevate a podcast?
1:53:56Chris Williamson:And then we did some cool things. And it's largely a passion project wing of what we do, but it's cool.
1:54:04Bill Gurley:In his famous Stanford graduation speech, Jobs said if he had never taken the calligraphy class, he doesn't know if he builds the iPhone the right way. You know, and the Mac, you know. It may or may not. It may just be kind of nostalgic speaking, but there are things you can borrow from learning far away that can be very impactful. And it's hard to know at the time, like when you're consuming it. That's why I call it a bit of a superpower or advanced level, I think I call it. It's not easy.
1:54:38Chris Williamson:But because you're translating, it's like an exchange rate between something else and this. So is that just cool for them to really take what that musician's doing or is this relevant to me? So I guess taste, discernment and when i think about areas that uh ai can't replicate uh community networking ability taste discernment yes i agree those are the i'm sure there's tons more but those are the ones at least for me with what i do it's not going to build a friendship with this other person that i that i want to hang out with i agree with that it can't choose is this the right guess and you the mr beast approach would be well there are just quantifiable metrics of how this person appears on a balance sheet what's the likelihood of this person being a big play guest or whatever um but that also doesn't account that's a local maxima which is everybody's got the opportunity to operate for that yeah to optimize for that whereas if you're trying to refine for the taste i agree different i can bill gurley ladies and gentlemen bill you're fucking awesome thank you for having me.
1:55:48Chris Williamson:I really appreciate it. A lot of my friends said you're going to love his energy, and sure enough, you're a legend. I'm glad that you're occupying some of those high-rises down. I've always wondered who lived in them. It's good. Where should people go to check out everything you're doing?
1:56:02Bill Gurley:So I've historically spent most time, we were an investor in Twitter early on, so I've developed my X profile the most, and that's where I post most stuff. So it's B-G-U-R-L-E-Y. there's a there's an instagram account that i'm for the first time in my life developing for the book congratulations welcome eagerly yeah it's a different world like i feel like such a neophyte like in twitter i get everything in like i understand instagram's a different language yeah it's a different language i'm figuring it out heck yeah bill i appreciate you thank you sir
1:56:41Chris Williamson:If you are looking for new reading suggestions, look no further than the Modern Wisdom reading list. It is 100 books that you should read before you die. The most interesting, life-changing, and impactful books I've ever read with descriptions about why I like them and links to go and buy them. And you can get it right now for free by going to chriswillx.com slash books. That's chriswillx.com slash books.
From the publisher
Bill Gurley is a venture capitalist, general partner at Benchmark, and a former Wall Street analyst.
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