#1071 - Bill Gurley - If You Hate Your Job, This is How to Start Over

Summary

Modern Wisdom #1071 – Bill Gurley – If You Hate Your Job, This is How to Start Over

Episode Overview

Chris Williamson sits down with legendary venture capitalist Bill Gurley to explore the pervasive phenomenon of career regret and the challenges of starting over, even after years spent climbing traditional success ladders. Drawing from his recently published book, Gurley discusses why so many people feel unfulfilled by their work, the psychological and societal factors that drive career decisions, and practical ideas for anyone wanting to make a brave change, regardless of age. This episode is rich in stories, frameworks, and memorable advice – all aimed at helping people escape the “conveyor belt” approach to life and careers.

---

Main Theme & Purpose

• The main subject is career regret and how to take bold steps toward a more authentic, fulfilling professional life, even if it means starting over later in adulthood.
• Gurley and Williamson analyze why most people stick with unfulfilling jobs, how regret often centers on things we didn't do (inaction), and what mindsets and tactics enable bold career changes.

---

Key Discussion Points & Insights

1. The Origins of Bill Gurley’s Career Regret Research [00:12–04:30]

• Gurley’s Background: Over 25 years as a VC, with a habit for chronicling insights from biographies, led to noticing common regret themes across professions.
• The Career Regret Survey: Informal surveys showed 6/10 to 7/10 respondents wished they’d chosen a different career. The notion of regret, especially “regrets of inaction,” recurred.
  • "They ruminate about what they didn’t try" (B, 03:09).
• Aim of the Book: To give readers the “permission” to pursue what they love, not just what seems safe or prudent.

---

2. Why We Regret Inaction More Than Action [04:30–09:30]

• Open Loops and the Zeigarnic Effect: Williamson introduces the idea that our minds can’t stand unresolved possibilities, which drives rumination about “the one that got away.”

"The main thing that you have is an open loop… we'd rather imagine a catastrophe than deal with the uncertainty." – Chris Williamson [07:18]

• Bezos’ Regret Minimization Framework: Visualizing advice from your future 80-year-old self to guide present choices.

---

3. The Conveyor Belt of Education and the “Resume Arms Race” [09:54–13:41]

• Loss Aversion & Sunk Cost: Many young adults stay in unsatisfying jobs because “tweaking away” from an invested path feels like throwing away years.
• Early Specialization: Kids are pressured to pick a life track at 17, with little time for exploring passions, leading to burnout rather than fulfillment.
• Angela Duckworth's Grit Revisited: Gurley recounts Duckworth’s regret at over-emphasizing perseverance over passion.

"She wished she had positioned [grit] as 50/50 passion and perseverance." – Bill Gurley [13:41]

---

4. Observable vs. Hidden Metrics in Career (and Life) [16:38–18:38]

• Flexibility is Invisible: Many trade hidden values (peace, flexibility, passion) for observable ones (salary, job title).
• Career Fulfillment: Gurley respects those who find meaning outside work but wants his book to empower those unhappy with their jobs or itching for something new.

---

5. Why It’s So Hard to Pivot: Money, Expectations, and Fear [23:25–27:51]

• Financial Traps: Many are “locked in” to high-earning, high-spending lifestyles that restrict risk-taking.
• Parental and Societal Pressure: Cultural norms and family expectations often stifle career shifts.
• Stories as Motivation: Gurley insists that narrative (not just frameworks) helps unlock courage in readers.

"I think these things stick in your brain more… they infect the brain a little bit more." – Bill Gurley [25:50]

---

6. The Power of Obsession & Passion in Work [37:27–41:47]

• Obsession vs. Discipline: When passion is high, discipline is frictionless. Obsession is a pull rather than a push.
• Single Organizing Principle: Williamson and Gurley discuss how founders like Bezos (“Does this make the customer experience better?”) and Musk (“Does this get us closer to Mars?”) use it to keep organizations focused and innovative.

"If it's pointed in the right direction... from the outside, looks like a superhuman amount of discipline. From the inside, feels almost like you haven't chosen it." – Chris Williamson [39:07]

---

7. Indicators for When to Pivot (and How to Get Unstuck) [42:21–46:45]

• 30-Year Fast Forward Test: If you don’t see yourself happily in your current role decades from now, it’s time to make a plan.
• Battle Card Exercise: Lay out several possible career options with pros/cons to simulate pathways before acting.
• Side Hustles: Experiment outside your main job—it's safer and can reveal new passions. Gurley champions Ben Gilbert’s model: always have a side project.

---

8. Peer Groups & Mentors – Learning and Support [48:46–55:54]

• Peer Community: Building “peer groups” with people at the same career stage offers support, honest feedback, and collaborative learning.
• Mentors: Divide mentorship into “aspirational” (study them from afar) and “practical” (target someone two levels above you).

"You should actually... would you share your best ideas with them? You should." – Bill Gurley [51:33]

• Mister Beast Anecdote: Sharing knowledge exponentially increases learning speed (“40,000 hours because we were sharing it all”).

---

9. The Limits of Grit – Grinding without Love Doesn’t Work [60:53–66:46]

• Flow State: Work that feels like “flow” or obsession identifies the right path. Pure grind without love leads to misery (and often, mediocrity).
• Competing with the Obsessed: AI founders are adopting “996” work culture (9am-9pm, 6 days/week) because they love it; Gurley points out you can't compete if you don't feel the same.

---

10. The Dynamics of Venture Capital; Founders vs. Ideas [85:32–99:54]

• What Gurley Looks for in Founders:
  • Product instinct
  • Salesmanship
  • Unreasonable determination (chips on shoulders put chips in pockets)
  • Will they do it “no matter what” (per Jeff Bezos)
• Founder > Idea: Many top companies started as something else and pivoted only because the founder wouldn’t quit.
• Beware Dilution: Founders who raise too often may end up with a tiny share of what they’ve built.

"There are businesses that shouldn't take venture capital..." – Bill Gurley [97:36]

---

11. AI Disruption and Future-Proofing Your Career [102:11–110:56]

• AI as a Tool, Not a Threat: For proactive learners, AI is a “jetpack”; for grinders without passion, it’s a threat.
• Jobs Most at Risk: Roles that synthesize, summarize, or translate text are first in the firing line (paralegals, coders, translators).
• Advice for Young People: Run toward AI; learn the edge of what’s possible in your field; continuous learning matters more than ever.

---

12. The Value of Cross-Disciplinary Curiosity [111:06–114:38]

• Range by David Epstein: Switching industries brings fresh perspectives, enabling breakthrough innovation.
• Seek Far Analogies: Learning from unrelated fields offers unique advantage (e.g., Jobs’ calligraphy class influencing Apple).

---

Memorable Quotes

"The biggest regrets people have... are regrets of inaction. He calls them boldness regrets." – Bill Gurley [02:49]

"It's what you didn't do... that humans are great at forgiving themselves for what they did, but they ruminate about what they didn't try." – Bill Gurley [03:09]

"If you have a job with a decent salary, I would heavily encourage them not to spend against it, just so they can have the flex to do other things, move cities, change jobs. All of which may be the right path for them." – Bill Gurley [16:19]

"You can fail at a job that you hate... so the prospect of potentially doing okay at one that you love is infinitely better." – Chris Williamson [46:45]

"Life is a use it or lose it proposition." – Bill Gurley [15:10]

---

Notable Stories

• Steve Harvey’s Teacher: At age seven, Harvey wrote “I want to be on TV.” A teacher scolded him, but his father told him to read that paper every day—an early example of support for boldness over conformity. [19:07]
• Tito’s Vodka (“Bert Beveridge”): Worked in oil and gas, then mortgages — hated both. On a whim, drew up what he loved and was good at, and started Tito’s Handmade Vodka on credit cards. Now, it’s the top-selling spirit in North America, still 100% owned by him. [33:27]
• Mister Beast’s Peer Group: Four teenagers in a Skype group, sharing everything about YouTube, multiplying their individual learning. “If there were a fifth person in that room, they would’ve made a million dollars, too.” [52:48]

---

Practical Takeaways

How to Start Over:

• Use the Regret Minimization framework: ask “Will I regret not trying this when I’m old?”
• Don’t overspend – financial flexibility creates career flexibility
• Explore side hustles that call to you in your spare time as stepping stones
• Build real peer relationships for honest feedback and support
• Seek narrative proof (stories of people who made big jumps) to emotionally prime action
• Battle card your potential next moves before taking the leap

---

Timestamps for Key Segments

• [00:12] Gurley’s journey to career regret research
• [04:30] Open loops, the Zeigarnic Effect, and boldness regret
• [09:54] The conveyor belt & sunk cost fallacy in careers
• [13:41] Grit vs. Passion, Duckworth’s recalibration
• [19:07] Steve Harvey’s childhood story
• [23:25] Why people get stuck—money, culture, fear
• [25:50] Power of narratives in changing beliefs
• [33:27] Tito’s Vodka origin story
• [37:27] Obsession vs. discipline in meaningful work
• [42:21] When to know it’s time to make a move
• [48:46] Building peer support groups; stories (Mr. Beast)
• [55:08] Mentors: aspiration vs. practical guidance
• [60:53] The limits of grit and “loving the grind”
• [85:32] What makes a great founder? (Bezos’ test)
• [97:36] On taking venture capital
• [102:11] How AI will reshape work
• [111:06] Range and the value of cross-industry thinking

---

For those wanting actionable wisdom and inspiration for leaving an unloved job, this episode is a must-listen. Gurley and Williamson combine decades of experience and the latest psychological research with moving stories and practical frameworks to help you envision—and execute—a better career future.

Transcript

[A]

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

[B]

so i spent twenty five 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 a early blogger it was actually a fax that's how old i am when i started and and i got in the habit of when i had ideas jotting them down and then 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 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 at the 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 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 but you use 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 would you do a different career and seven out of ten 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 ten 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

[A]

he's been on the show about regret

[B]

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 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 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 and we're pushing them towards jobs that are you know 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 you know the perseverance part we've taught them but if they don't have the love for it it turns into burnout 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 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'll be a hu 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

[A]

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 that's right 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 i

[B]

was hoping to bring up one of the many biases i've read about in all the behavioral science books but i'm gonna go to a different place which is i think we ruminate a lot like like our brains you know constantly are 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 like to build a story especially a positive story around the what if i 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

[A]

it you'll be familiar with the zeigarnic

[B]

effect i'm not tell me oh cool

[A]

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 there stood no pen no pads no hands behind their back and they go this guy's crazy like he's insane i'm definitely gonna get something wrong and sometimes you might go i'm gonna we'll take the sprouts but i extra bacon no no goat's cheese but you only just see if if all right mister no no no notepad yeah and the study ended up finding out the zyganic effect which is an open loop closed loop bias that exists inside of the human mind while the tables were still open the servers were able to recall what the orders were very closely and as soon as they went that you 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 where did you which hotel room did you stay in two hotels ago i'd give it seven thirty far 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 yes yeah the open loop the human mind abhors an open loop and i get the

[B]

sense that i see what you're saying

[A]

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 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 what could have happened yeah what could i

[B]

have done and there's 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 de 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 eighty years old and was trying to get advice from his eighty year old self about what to do so he like put himself in that future place where he might have that that boldness regret and in my own career people 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 thirty years and was able to like fast forward that in my brain and i was unhappy with that reflection which encouraged me to to think about what's next when

[A]

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 it is a really wonderful idea and i guess jeff's got other stuff that he can be well known for so perhaps you know well it's

[B]

actually quite synonymous with one of the seven habits of highly effective people begin with the end in mind it has a similar kind of when looking at

[A]

the regret minimization framework what are the things that what are the common pitfalls that you've seen people do even both inside of their career and outside of it you must have reflected on this

[B]

a lot 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 a i'm sorry a resume arms race we've built this pipeline for these kids that's so intense tense 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 is is throwing away the investment does that make sense like a loss aversion type thing 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 in in there's a lot of of studies that have been done like i won't get the numbers exactly right but like five years after college forty percent of people are no longer working in the field that was their major and that number gets bigger at ten but i 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 mention this to young people there is this weight there is this weight they feel like an obligation to especially maybe

[A]

decisions that they locked in when they were seventeen yes well and that's another

[B]

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 we don't allow children enough time to explore y and you know height says it he has a chapter called let them or the loss of play or something um rick rubin's been pounding on this he talks about it in

[A]

his we looked at gene twangy's work generations does is that another one yeah so generations is is really fascinating this stinks of you highly recommend it you read okay i will and she talks about extended adolescence yeah sort of twins with some of height stuff we've got a real interesting duality going on which is in one world you've got the these kids that are sort of being forced to become adults more quickly yes than ever before we expect you to know what you potentially the set of railroad tracks for the rest of your life the next thirty years of your career and you're only seventeen and you got to know and apply and then at the same time kids are moving out of the house later they're getting their driver's licenses later they're getting employment later they're getting into relationships at lower rates less alcohol less casual 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 the socially very immature professionally expedited and he ties them together it's just because gene twangy yeah for sure i think that oh actually 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 everything just feels like i need to get my act together 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 compensatory yeah like

[B]

i mentioned i think about ten years after duckworth wrote grit she said that she wished she had positioned it as fifty fifty passion and perseverance and she if she could do it again she'd put more on the passion because she thinks we taught a whole generation of of the high performer children how to grind like we taught them to persevere

[A]

which is well and so i get that 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 oh how do i get the thing aligned 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

[B]

get i do think it is the hardest question 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 seventeen 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

[A]

question upon you've got this line life is a use it or lose it proposition yeah what's that mean well i

[B]

mean it's tied to the the the the boldness regret right like you're going to get to the end and and then it's done and 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 the the recognition that that life moves much faster than any of us realize and then it's done and and and you can get locked in even sooner if you spend up to your limits you can you can you can freeze yourself in a job like that you can't leave and you can do it with personal commitments as well i my my second career was you know 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 but they had to place in the hamptons the summer lease like 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 yeah

[A]

you're locked in at this very high burn rate which means you need to keep pouring fuel in the top of

[B]

it yes yes i 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 flex to do other things move cities change jobs all of which may be the right path for

[A]

them we'll get back to talking in just one second but first if you have been feeling a bit sluggish your testosterone levels might be the problem they play a huge role in your energy your focus and your performance but most people have no idea where theirs are or what to do if something's off which is why i partnered with function because i wanted a smarter and more comprehensive way to actually understand what's happening inside of my body twice a year they run lab tests that monitor over a hundred biomarkers they've got a team of expert physicians that analyze the data data and give you actionable advice to improve your health and lifespan and seeing your testosterone levels and tons of other biomarkers charted over the course of a year with actionable insights to actually improve them gives you a clear path to making your life better getting your blood work drawn and analyzed like this would usually cost thousands but with function it's just four hundred ninety nine dollars and right now you can get a hundred dollars off bringing it down to three hundred ninety nine bucks get the exact same blood panels that i get and save that hundred dollars by going to the link and in the description below or heading to functionhealth dot com modernwisdom that's functionhealth dot com modernwisdom 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 which again is a 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 sure you know 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 try 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

[B]

think that's a good framing so is

[A]

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 why should i care about my career it's just the thing that i do from nine to five or whatever eight to four every day why why should i try and optimize that is is being fulfilled at work a luxury

[B]

i guess what i would say is i have a immense amount of respect for someone who adopts that mindset the one you described especially if they're really thriving in something that may not may they may not perceive to be an occupation that could be a religious community it could be volunteer work that they do 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 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 too i really really want to read my book um there's this there's a there's a great story there's a couple of these actually but i'll i'll i'll i'll choose the steve harvey one there's a there i don't know if you've seen this but you know who steve harvey is the comedian who does the talk family feud now yep 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 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 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 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 i'm a parent of three and i've lived through this phase that we're talking about your intuition as a parent like the some in your dna somewhere is to look after the economic welfare of this child 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 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 like 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 you know

[A]

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 thirty five yeah 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 yeah why do some people successfully pivot and others end up getting stuck

[B]

well i mean there's a there's a you could come up with a number of things one of them is financial which we've we've talked about you could be overspending there's a there's a different case where you're just you're you're stuck financially like you need you're living hand to mouth there's a i have a i have a profile in the book of jen atkin who i don't know if you know she is probably the most most successful hairstylist of all time like went not only achieved touched the top rail of that but then launched beauty products sold that company but she moved to la with hundred dollars in her pocket and that's not to say anyone can do that but like there there are stories of people with near nothing starting on the very bottom rung and finding their way to be successful there's this classic meme of starting in the mail room in hollywood and david geffen and and barry diller and all these people started in the mail room you know it's it's about as low as rung as you have in that business so i i think it's possible but you may feel stuck financially 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 but that weight can be there too like you may feel i think there are certain there are certain cultures where where like being a doctor is considered really in russia like being an academic was so you may 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

[A]

this movement what about the fear there has to be a huge chunk of people that just i what if this doesn't work it's sort of ambient ephemeral this fugue fog thing that's come down

[B]

on them if you allow me to give you a little history of how or why i would say i spent six years turning the the original presentation into a book and i 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

[A]

he's the absolute goat and he

[B]

was on he was on a podcast called why we write talking about david pearl the power of 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 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 a do b then do c but they don't they don't have this kind of spirituality to them that i think can infect the brain a little bit more does that make

[A]

sense it's one hundred percent correct i mean ben shapiro's favorite 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

[B]

the fact yeah so we have eight nine or ten i should know the exact number but i can't recall right now of these profiles and i alternate them with the principles and i thought about it like candy and vegetables you know or something but you get you get some of both and it brings

[A]

the ideas to life yes and i

[B]

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 i 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 doctors yeah all the stuff that everyone knows is is nice linear progression 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 i hope it

[A]

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 does it straight up does not stick pithy mantras and quotes and stuff can do they're a nice compression algorithm i think for bigger things but really what you're optimizing for and i'd be interested to know if you agree with me on this i think you're optimizing for memorability yes and 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 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 onto but if you give somebody a story how how are you how are you going to forget that years

[B]

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 nonfiction articles there's a website called long reads okay that 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 suge knight and and and snoop and i think biggie were on the COVID of new york time magazine when i was it was in ninety three or ninety four and it was twenty pages that may have been the first one that got me into this but 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 i think truman capote's highlighted in that tom wolf put together the first one and then the second one has krakauer and lewis and like all the

[A]

modern well now we've seen 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 bari weiss you've done this sort of double u 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

[B]

or whatever i'm a huge barry fan

[A]

so talk to me about the risk of starting over in your thirties or forties 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 thirty seven 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 thirties and forties well i mean one

[B]

thing i would encourage you to do there was this book i read when i was really i think back in business school called shark proof by harvey mckay 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 in a file but you could create it in a google doc or something that where you're just keeping notes like well if i do it one day you know 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 like you can you can begin the process before you make the leap right and then 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 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 learned about stocks and i was trading stocks you know i'd read one up on wall street i had this i forget what it was called this book you just get this book with all these one pagers on every stock like i was that's what i was doing in my spare time so if you're doing something like that in your spare time like it's calling you you know and then the third thing there's a chapter in the book actually titled never too late and we list about twenty people that did post forty pivots and we go deep on four of them my favorite being local austinite bert beveridge bert's nickname is tito so that'll that'll tell you who he is but seismology degree undergrad worked in oil and gas for for several years ended up down in south america where he got frightened by a few experiences so he hung that up out of fear and the boom bus cycle became a mortgage broker didn't really love it you know not sure he equated his identity to being a mortgage broker 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 he's like hanging out at bars on

[A]

the left

[B]

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 but of course tito's is now the most best selling spirit in north america he owns one hundred percent of it

[A]

himself no way the whole thing's bootstrapped

[B]

yes nineteen credit cards but it's such a great story like it's just such a great story and now he's at the phase in his life where he's giving back and launching foundations and this is my point i had a young person at john hopkins raise their hand and say but i i don't want to chase my passion i want to be purpose driven and i i thought to myself you know every profile in the book these people are touching more lives than they could have ever imagined

[A]

like i don't want to chase my passion i want to be purpose driven

[B]

i think it's part of a new movement to just like feel good about yourself like i'm a i'm my my main goal in life is to help

[A]

other people 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 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

[B]

my only point was these people that are able to climb from the bottom rung to the top and do it in the right way end up touching hundreds and hundreds

[A]

of lives they're serving in a much more seamless way that's leveraged as well yeah yeah yeah yeah yeah i mean

[B]

one of my favorite on that front is many years ago because i was involved with opentable 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 got to be that's got to just feel amazing what

[A]

is it about his demeanor or culture

[B]

or ethos the book talks about this kind of understated sensibility to his book to hospitality like like just trying to read the room on each and every customer and really understand you know what they're 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 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 that's so cool which i think is is is it's also that's the second principle in 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 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

[A]

passion a quick aside i've been using eight sleep for years and i genuinely can't imagine life without it having a mattress that actively cools and heats each side of the bed is a total game changer and the newest model the pod five takes things to the next level it now includes a temperature regulating duvet that works with the smart mattress cover to deliver full body climate control maintaining your ideal temperature from every angle all night long the new base also includes a built in speaker so you can fall asleep to ambient sound rainfall or doctor andrew huberman whatever helps you switch off and with upgraded biometric sensors it now runs nightly health checks identifying disrupted breathing abnormal heartbeats or sudden changes in your hrv it now cools heats elevates and monitors your sleep better than ever which is why eight sleep has been clinically proven to give you up to one hour more of quality sleep every night and if you're still on the fence they have a thirty day sleep trial so you can buy it and sleep on it for twenty nine nights and if you don't like it they'll just give you your money back plus they ship internationally right now you can get up to dollar three hundred fifty off the pod five by going to the link in the description below by heading to eightsleep dot com modernwisdom using the code modernwisdom at checkout that's eightsleep dot com modernwisdom and modernwisdom at checkout joe hudson's got this line enjoyment is efficiency he says i liked it i think it's really really true yeah that people 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 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 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 my house back in the uk has got a podcast studio in it the one that i live in right now is still podcast eight years in a thousand episodes every single house has had one 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 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 my entire life gets warped around it i'm sure you'd be familiar with the 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 so everything every single decision in amazon was threaded through this sort of single eye needle and musk says does this get us closer to mars does this get us closer and by the way

[B]

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

[A]

i know of they didn't get laden down with diseconomies of communication lumbering behemoth

[B]

bureaucracy 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 on cheeky pine i think this dual cash yeah this came up this came up like 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 two hundred thousand employees and elon jokes yeah there's two hundred thousand employees like you have to have some heuristic simplifying heuristic that can spread

[A]

through their spinning too many plates yeah

[B]

exactly yeah yeah it's pretty impressive it's

[A]

super impressive 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

[B]

of morale so do you know i mean i love i love this test of is do you see yourself doing this thirty years from now because if the answer to that is no you should get busy what's the line from shawshank like get busy living or get busy dying like if you know that's true like well now is when you should start i'm not saying like quit tomorrow but like start building the plan like and then there's all kind of things you can do in designing your life dave evans says has this exercise where he says create three to five scenarios and battle card of what you might do next like you know fill them out i can really help right like you could build a twenty pager on each one of these career paths what might i like what might i not like what are the three things people love in this career what are three things you can steer it at all right you can ask people in those fields you can go find them so you could you could role play being in each of these there's a there's a there's a heuristic in the book that i borrowed from from ben gilbert had 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 what's there's something really great about that one in each of his cases he ended up doing something pretty remarkable in the side hustle 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 but i think it all 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 madrona vc asked him if he could start a podcast and look where that led and i just had dinner with both of them and they were in austin and man they're happy like i gotta tell you like they are really happy people so similar to you and your obsession and they fell into it through that through getting there through that way so i think those are some things you can do to to test and then look what are you doing in your spare time like are there any signals there those are all great ways i wouldn't quit if you don't know where you're going

[A]

that doesn't make any sense yeah yeah it's such a good shout to say sort of what are you thinking about in the shower yes what are you doing in your spare time i keep on 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 a you know maybe there's something going

[B]

on there let me share this fun story i just stumbled on because i was i was 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 he said oh i you 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 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 and then he builds software then he starts a podcast he has nine hundred thousand 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 that's brilliant it's so great 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 you know if you really love being around that stuff there's

[A]

tons of opportunity especially given that you can fail at a job that you hate you can 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

[B]

think so 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 gonna you're not gonna ruminate on it forever especially if

[A]

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 someone's let's say it's a maybe a slightly less momentous decision decision between one city and another or 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

[B]

new yes i liked it i liked it i just had a similar life experience i spent twenty five 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

[A]

like it's awesome new place for coffee new place to work take your calls

[B]

your morning walk all that's different that's great i agree with that sentiment so

[A]

you quit a successful job at compaq yeah to start again yeah how do people know when they're plateauing versus they're just a bit bored or something yeah

[B]

a few people have asked me this question once again i think the thirty 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 unlocked book 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 like am i 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

[A]

those questions of 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 absolutely finesse my way out of

[B]

there's ten other reasons why you should build that group but it's good at helping with that problem that you just

[A]

described 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 yeah it's a tough

[B]

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 zero sumi yeah and and we borrow a lot of our mental frameworks from from finite games that have a beginning and an end and 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 and 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 you should actually i believe but a lot of people wouldn't and so if you if you once you get to that place it's a really special place there's a there's a story in the book about crystal 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 like 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 they're all eight all eight of them are d one athletic directors now and they all started on the bottom and if you follow them along that journey they're learning elevated each time the each year they met each each time they texted the problems they were encountering they were sharing they're 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 and mister beast did this when he was seventeen 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 sixteen 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 ten thousand hours referring to the malcolm gladwell book he says we got forty thousand hours because we were sharing it all that's not the exact math but it's a cool reflection of

[A]

the moment you know a quick aside you've probably heard experts like doctor rhonda patrick talk about the benefits of omega three s they reduce hello omega three s there they are they reduce brain function no they don't they support brain function maybe i should take more they support brain function reduce inflammation improve heart health and are backed by hundreds of studies but here's the thing all omega three s are not made the same most brands cut corners they use cheap fish oil skip purity testing throw in fillers and and call it a day but with momentous you know you are getting the highest quality omega three s on the market they're nsf certified for sport and they're tested for heavy metals and purity so you can rest easy knowing anything that you take from momentous is unparalleled when it comes to rigorous third party testing what you read on the label is what's in the product and absolutely nothing else best of all momentous offers a thirty day money back guarantee so you can buy it and try it for twenty nine days if you don't love it they'll just give you your money back plus they ship internationally right now you can get thirty five percent off your first subscription and that thirty day money back guarantee by going to the link in the description below or heading to livemomentous dot com modernwisdom and using the code modernwisdom at checkout that's l i v e m o m e n t o u s dot com modernwisdom and modernwisdom a 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

[B]

i think you do both 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 like especially if you get the peer group in the right place you you tell them i'm struggling here like so i think it i think it's just a different purpose with 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 gonna be ninety

[A]

eight because the cfo of this company doesn't want to be friends with you

[B]

yeah 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 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 you can learn faster than you ever could have learned before 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 ten x or more like the probability that you're going to get them to do the work is so much better like i noticed that

[A]

when i first started the show in twenty eighteen 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 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 you 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 i get it researcher at fucking university of arizona and they're like oh well it's just me that handles my pod 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 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 you know reaching out you please put me in touch with whoever handles bill's 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 linkedin dm requests is it them or is it gonna 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 you on to the right

[B]

department 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 through them oh yeah learn all you can about them like like be generous and kind and thoughtful you know good good it will pay off big time

[A]

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 it 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 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 yep

[B]

precisely

[A]

so in your framework loving the grind is sort of a non negotiable can someone sort of learn to love grinding or is that innate i don't think so but

[B]

you know when you were talking about your your love of podcasting you know the the word that popped into my brain and there's a book by this title was flow and i i just find people that are truly tilting against their passion they never even think about it as work like it and and at times the experience does go into this flow thing like where when 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 i suspect some human is just wired in a certain way where they might be able to do it but i don't know that most humans could like and i don't know i i do think we get a lot of young people to do it for an extended period of time and and i mean the meat grinder thing yeah i meet so i i just yesterday met with five of the top i i helped start this robotics honors program at texas and i met with five of them and like like you know they're giving you their background eagle scout and and it's fifteen eighty sat and all like clearly this human's been programmed to go take the hill like on every single thing they do but i don't think that's the path to greatness like you know what i'm saying i just don't think i don't think just being good at the grind is is what it takes to to

[A]

be truly exceptional 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

[B]

i think maybe if you're just so damn competitive like winning all the time

[A]

is 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 yes i think michael jordan would be a good example of this 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 whereas you know jordan invented rivalries yeah he invented slights against himself there was was it ninety two or ninety three very driven human being he wins some i think it's his induction into the hall of fame and during that speech this is the moment that you've worked supposedly your entire career

[B]

for he takes a shot at somebody

[A]

right he spends the entire speech just revealing all of the slights that from his past and this person and this but they didn't believe that i'm getting da da da da you're even at the moment where you've broken through escape velocity you're you're out in space

[B]

i don't i don't love that that much you know i love it's not the

[A]

energy that i have yeah so there's

[B]

a there's a there's a counter example to that there's this thing you can find on youtube where shaq was on the that famous show that he does with with kenny and and charles and ernie and inside the nba i think it's called the 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 thankful like gracious for four or five minutes and ernie's crying by the time he's done and i love watching it i watched it it probably ten 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 maybe in and it makes him look like remarkable you know it really does like that he 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 it was is i like that i like that

[A]

version better it feels much more pro social yes i suppose the problem is 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 true 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 metal is the message very much for this stuff well

[B]

and look that is more of a finite game right like that is and i you you'd use downhill skiing but there are like those kind of competitive sports you may need to be sharp elbow to climb to the top if

[A]

you're an author the same thing is

[B]

not true that's right that's my main point and most of the careers most of us chase that's not that that's not a reality but but i also have a principle always give back which is why i i feel warmly about the shaq thing which is i 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

[A]

your corner 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 well

[B]

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 twelve years plus four sixteen 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 sixteen hours a week or a day we all applaud it which is weird because if you said that about a engineering career they'd say you're a bad human 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

[A]

doing 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 all the rest of it and don't get me wrong there are certainly some bosses in 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 fail to understand is there are people out there to whom that sounds like a dream yes they want to work eighteen hours a day fueled exclusively on high quality stimulants and chick fil a especially if they

[B]

get to hang around with the smartest

[A]

people they and they want to be pushing each other and they want they want to send it they want to send the living shit out of it

[B]

you know who's doing that right now which is super interesting the young ai founders they've embraced this meme from china nine hundred and ninety six it actually was developed in china which means nine am to nine pm 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 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 and these young kids in this ai world eating the lunch are the ones you're talking about that

[A]

want that experience who are some examples

[B]

of those i i think almost all of i'm i'm serious almost all of the ai companies in san francisco have this mindset especially if they have a young founder like a twenty twenty two which is there but 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 i don't choose their

[A]

own life 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 but i

[B]

would say this if you're 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 like do what you love because if you're sitting next to

[A]

that person and you're white knuckling it and they're loving every moment yeah you're

[B]

probably going to lose because they're at home learning in those extra hours and stuff you're not like there's no way

[A]

to keep up yeah well the the 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

[B]

the gap is going to grow and and i'll tell you one other thing which i 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're 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 out of level like they view ai as grind versus grind it's gonna out it's gonna crush me it's gonna i'm gonna lose my job look at this world 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 they're a continuous learner for that person ai is a jetpack like they can now do more things faster that they wanted to do and they can achieve more than they were able to before they get to run extra fast so two people maybe in a same station in life ai looks like the opposite to them a threat

[A]

or a nitrous turbo boost yes a quick aside if you've noticed your energy isn't quite what it used to be even though you eat well and stay active there might be a reason for that as we age our mitochondria which is the parts of our cells that produce energy become weaker and make less energy which is why i am such a huge fan of timeline they developed this pill right here that helps clear out damaged mitochondria so your cells can actually renew themselves and this isn't just theory in clinical trials people saw mitochondrial renewal increase by more than forty percent in just sixteen weeks along with improvements in their overall energy timeline is backed by over a decade of research it has more than fifty patents and is the number one doctor recommended mitochondrial supplement on the planet i started taking it nearly two years ago because it was recommended to me by my doctor and that is why i've used it for so long since way before i knew who made the product and that is why i partnered with them best of all there's a thirty day money back guarantee plus free shipping in the us and they ship internationally so right now you can get up to twenty percent off and that thirty day money back guarantee by going to the link in the description below or heading to timeline dot com modernwisdom that's timeline dot com modernwisdom 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 me too instruction of don't be pushy with women and i realized that it made conscientious anxious guys even more timid yes while the dudes that were blowing through boundaries just didn't take heed 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 they're called 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 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 disproportionate way that advice call them advice hyper responders right 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 that 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 of lauded but largely unfulfilling wins

[B]

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 sixty 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 twenty five i i think when you're one of the benefits of being eighteen is you don't see the end of times at all like and that gives you all kind of superpowers like to to play 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 a different at bat like you

[A]

want to front load that fear a

[B]

little bit yeah if you can i don't know if everybody can well i

[A]

certainly know that the regret minimization thing there's a variety of different exercises that are done george my housemate used to think 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 i 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 he viscerally thinks about what it would be like to have no arms or legs for thirty minutes to be grateful is that and then to be reborn into this body yes with the arms and the legs so i've been really pushing hard over the last eighteen months on emotional work trying to get below the neck as i've said and 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 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 it's trying to overload emotion it's like oh my god there is a there's a great fucking workbook from tony robbins unleash the giant within within but it's this weird nineteen ninety four audible workbook and it's only an hour and a half long i can't even find it listed i've got it in my audible george's got it in his and 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 yeah 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 he'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 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 and i've had to make some i moved from the uk i was thirty two years thirty three nearly thirty three years old with a successful career in the uk running nightclubs one of the biggest events companies in the north of england it's something i dedicated fifteen years of my life to covid had just happened and nightclubs were just reopening and the clubs reopened and i didn't want to go back i just wanted to do

[B]

the podcast and that was the exercise that you went through and i presume zero regrets about the move it's the

[A]

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 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 twenties 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 gonna work we constantly had money problems we didn't know if we were gonna make it you were worried about where your future was going and we da da da 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 so 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 all of that together 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 gonna laugh at me and i'm gonna have to come back and live in my mum and dad's spare room and i'm gonna have a gluten intolerance and a club foot and be under a bridge and it's all gonna and yeah had it have not gone well maybe that would have been the case but that is the worst possible scenario and there were a million there's gradations between the best one and the worst one but yeah i'm really proud of making that decision but 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 decisions which in retrospect feel very obvious i think at the time require inhuman amounts of motivation to go to get the activation energy to

[B]

get you moving i like the battle card notion i mean it's similar to some of the design in your life stuff but 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 them i love that idea i think one of the reasons i was a useful venture capitalist and one of the reasons i this regret minimization thing worked for me is i think i'm very good at bringing forward the future in my brain like like extrapolating back if you will like almost like a life npv kind of thing yeah yeah just able to do that and it's like reverse time travel yes and and it makes those exercises work better you know the fact that i somehow can do that in my brain so

[A]

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

[B]

yeah decision framework and and a lot of vc's say the same things over and over so i'm a little hesitant but i'll do it anyway 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 you got to be ahead of market humans and how humans like to interface with things and a whole bunch of stuff so products a big one salesmanship is a huge one there's that 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 people so that 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 with lux capital says chips on shoulders put chips in pockets and like like someone that that maybe failed a couple

[A]

times got a point to prove oh

[B]

man you want to feel that like you want to feel that they're never going to give up it 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

[A]

was that line is this person going to do this no matter what was

[B]

that bezos bezos i asked bezos you found that i asked bezos once how he could be such a successful angel investor because he's running the largest employment count company in the world there's other to do yeah exactly he has less

[A]

time than you to scrutinize no way

[B]

less yep and he said the only thing he looked for is the determinism how is this person going to do this no matter what in all of his questions that's so cool all of his questions were around that one very

[A]

thing what if this how would you approach that how have you in the past and got over why are you

[B]

doing it like you know what if this comes up like what if someone offered you that you know i had

[A]

a conversation with a friend a few years ago and he gave this wonderful example of champions and 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 yes and when you're talking about but a zero sum game or a game that's more competitive found 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 could push you right across the line very very a

[B]

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 it and i it's horrible the accident she had but i couldn't help but think of lindsey vaughn like she had a who's that lindsey vaughn's the downhill skier that's forty one forty two and is in the olympics right now okay and you know she had retired a while back and came back trained again was her 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 going to compete anyway and unfortunately had an accident went to the hospitals had three surgeries snapped her yeah but but to be in your forties and coming back in some ways look somewhat injured and i'm like i'm going

[A]

anywhere sending it anyway look i i i i didn't know about this story

[B]

this just happened like a week ago

[A]

i kind of like it i kind of like it what a way to go out yeah okay fair enough you're going to be laid up better to

[B]

burn out than to fade away well

[A]

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 yeah would it have held up am i going to go back at forty five nope not going back at forty five no

[B]

no it's the last shot this is

[A]

it yeah so i kind of like it 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 well here's one

[B]

one proof point that would speak to this is there are 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 like 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 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 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 fifty fifty 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 gonna there's a fifty fifty chance you just get a bad apple in which case it's all toast so yeah there's and and that lore goes beyond me i mean i think the 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 are there's way more stories 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 in that that that product thing is just more artistic

[A]

you know more like a taste again

[B]

yes more like a movie than than i love that business business products are more systematic yeah yeah and you can

[A]

algorithm that down to steve jobs once

[B]

said that the difference is the buyer in a business isn't the user and he made that point and that may be it like that may be the

[A]

essence of it it that's cool i this thing the the beverage that you're drinking is mine and that's the first big company that hasn't been something that i've directly operated aggressively myself that i founded and one of the interesting elements that i've seen with this where we we did a raise last year we raised three point four four million dollars and right now we're in the middle of raising six and a bit 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 it's fucking forever away drove to leeds for one investor meeting 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 and 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 a couple of times we 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 the 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 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 and in the middle is a guy that overcomplicates everything and he's sort of screaming and getting and 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 whey is consumed within a thirty minute and he replied with that meme and he said the guy in the middle said 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 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 you'll make it work no matter what yeah and that was cool it's the first time that i've you can take

[B]

that too far i've met with founders who who are anti deck i even wrote a blog post called in defense of the deck because they want to

[A]

make sure that you don't misspell one of those words but yes they walk

[B]

in the 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 so i and i in in this blog post which i'd encourage people to find i show steve jobs mark benioff jeff bezos in front of a

[A]

deck like if it's look it's good enough for them no no no i don't i don't disagree i'm not advising people people are prepared if you are fucking investing in newtonic please scrutinize but

[B]

but i want to say one other thing about this because i think it gets more to the point of 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 fourteen percent 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 twelve percent 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 does that taps in it's it's about chris for sure yep but there's they also need to kind of love the category and love the idea and want to spend ten years working on the problem like all those things like it needs it they have to flip from zero to one in their own head yeah in this human's head does that

[A]

make it harder for businesses that are less sexy of course unquestionably that's why

[B]

there's like these these mid market pe people they go do 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 on them too bad like somebody there are you can make money there are are things to be done you know but but i also would say and i think this is important there are businesses that shouldn't take venture capital and 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 one hundred percent on sweat equity is now ten times higher and just make sure you think through all that somehow through the use of these nineteen credit cards and everything bert

[A]

beverly the guy behind tito's one hundred

[B]

percent of his unbelievable do you know

[A]

gymshark are you familiar with gymshark no so it's probably one of the biggest british companies to activate i'm actually wearing the trousers right now and ben the ceo and founder is a good friend and it is a two point six billion pound company and it is entirely private and i think he's still got seventy five percent of it himself it's

[B]

a lot but i would say even if you're going to sell for twenty million there are far more companies that want to do a tuck in twenty million dollars acquisition than want to do a half a billion acquisition what's the

[A]

size of the market you're selling it

[B]

to well plus if you're a large public company you can do a twenty million dollars acquisition without filing anything without telling anybody your boss won't care if you own one hundred percent of a twenty million dollars company that's lifetime wealth like trying to make twenty million dollars selling a company for half a billion that's hard because it's hard to sell

[A]

fewer people that can buy it it's going to have more scrutiny that goes over the top of it you've now

[B]

diluted down 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

[A]

company 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 that's so cool

[B]

yes yes it matters it really matters it really matters and by the way if you sell that first company for twenty million that you own ninety percent 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 you know do it the second time

[A]

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

[B]

for no doubt liqpref 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 five hundred 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

[A]

is yeah i mean i i feel fortunate when we did the first raise i bought back in i didn't want to dilute oh nice i threw more money in i threw more money in

[B]

actually and by the way the investors love seeing that love love love seeing

[A]

that i was like i am not in fact i gained i gained share of nutonic when we did the raise so i bought in 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 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 cool and 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 are you most excited about with regards to the industry of ai and what do you think is overblown alone

[B]

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 like it's very clear right if i had a plow and a tractor and a and a 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 i can do more stuff and this is the latest of those things and anyone that is a skeptic or and i've met a lot of like the top academicians that are skeptics and all this you are you're no different than the luddites with the with the looms in europe 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 like you're you're the one they're asking all the questions of like what's this capable of and so i i in in the in the chapter i have on hone youe 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 you look going in

[A]

the middle is where you don't yeah

[B]

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'm anxious this why also why i was a a useful i use the word useful venture capitalist i have fomo about new that i don't understand so up until at least a year or two ago if something shit if there's an app in the app store in the top ten i've never heard of like hives like i have to know i

[A]

you're allergic to ignorance yeah i'm

[B]

coming off of it a bit because i haven't done a clawbot yet which i feel guilty about oh you can't

[A]

get it you can't get a fucking mac mini that's why you're not going to be able to buy them they're

[B]

all sold out but i feel guilty

[A]

about that yeah yeah yeah you've got

[B]

massive fomo but it's useful like and so anyway i think that 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 you understand what i'm saying like i had this great experience with the 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 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 this so i asked chat gpt in the pro version the two hundred three hundred dollars a month whatever it is write me a twenty page report on the best concluding chapters in non fiction 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 ten took an orthogonal direction to the book so it didn't summarize it brought in a new perspective and that gave me an idea i i then went and and ideated on that concept and it gave me a new idea to take it in a different direction and what was the idea loved it huh what

[A]

was the idea

[B]

the the not i all right i'll give this one away the concluding chapters titled it ain't easy 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 gotta struggle you gotta suffer you gotta be okay with

[A]

failure in praise of the grind yes

[B]

and the editor loved it good i

[A]

think that's i think that's an important

[B]

message yeah so i if i don't have ai i don't do that that like you know and it didn't write it for me i it just gave me a new lens for how to think about it when it comes to

[A]

the ai thing what what do you think it's going to do to the field of work generally what what areas would you be worried that are going

[B]

to be obsolete anything that was synthesizing i mean so the llm large language model is really good at tech 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 rules there's more freedom in actual language text than encoding 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 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 the 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 move upstream be the one that's best at exercising that with this tool but the old tool doesn't doesn't work like it's not going to be real

[A]

if you were twenty one and starting again with no knowledge or connections what do you think you'd be focused on what would you do

[B]

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 ten clawbots versus now where i don't have that that need to see what's possible i'm i'm fascinated by the the agent idea for a personal assistant like a running buddy i just find that fascinating 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 at and if you start with that as your construct i think you build the wrong thing does that make sense because

[A]

you're trying to backwards integrate something that's already a little janky and i don't

[B]

think the user wants to even see that stuff like 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 it a database like type enterprise app historically did it you know so so anyway those are things that pop into my brain when you say that those are things i'd be playing with i

[A]

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

[B]

the second half of range impacted me and david epstein yeah yeah and the book's known for being this antidote to malcolm although they're very close friends in fact malcolm's quoted on the COVID of range i think but the book people talk about this generalist versus specialists 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 i'd 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 field like if they enter through the side door you understand and it

[A]

relates they see things differently yeah yeah

[B]

and they're able to bring patterns from 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 pier 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 there it's it's more noisy you're waiting through like it's harder

[A]

less aligned right yeah yeah but the insights are powerless step changes it'd be

[B]

like you like listening to someone talk about great writing technique and get an idea for the podcast you know but

[A]

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 one thousand was me recreating the house from interstellar on a eighty five foot video wall the biggest video wall in texas using the same technology that star wars used to and we rendered the entire scene in unreal engine five 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 eleventh anniversary of interstellar and we were sat in front of the house 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 and da da da da and then we did some cool things and it's largely a passion project wing of what we do but it's it's cool

[B]

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 in the mac you know it may or may not it may just be kind of nostalgia 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 but

[A]

because you're translating it's like an exchange rate between something else and this is that just cool for them can i really take what that musician's doing or is this relevant to me so i guess taste discernment and when i think about about areas that ai can't replicate 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 want to hang out with i agree with that it can't choose is this the right guess and you you the mister 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 but that also doesn't account that's a local maxima which is everybody's got the opportunity to operate for that to optimize for that whereas if you're trying to refine for the taste different i can't bill gurley ladies and gentlemen bill you're fucking awesome

[B]

thank you for having me i really

[A]

appreciate it a lot of my friends said you're going to love his energy and sure enough you're you're you're 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 it's good where should people go to check out everything you're doing

[B]

so so i've historically spent most time we were an investor in twitter early on so i've developed my 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 yeah it's a different world like i feel like such a neophyte like in twitter i get everything in like i understand it instagram's a different language yeah it's a different language i'm figuring it out out heck yeah bill

[A]

i appreciate you thank you sir bye i get asked all the time for book suggestions people want to get into reading fiction or non fiction or real life stories and that's why i made a list of one hundred of the most interesting and impactful books that i've ever read these are the most life changing reads that i've ever found and there's descriptions about why i like them and links to go and buy them and it's completely free and you can get it right now by going to chriswillx dot com books that's chriswillx dot com books