Please enjoy this transcript of another in-between-isode, with one of my favorite formats: the good old-fashioned Q&A.
Books, people, tools, and resources mentioned in the interview
Legal conditions/copyright information
Additional podcast platforms
Listen to this episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, YouTube Music, Amazon Music, Audible, or on your favorite podcast platform.
Transcripts may contain a few typos. With many episodes lasting 2+ hours, it can be difficult to catch minor errors. Enjoy!
Tim Ferriss: All right. Hello, everybody. Thanks for making it. We’ve got lots of questions that were pre-submitted. There’s a lot to cover, and I will begin with saying there are many, many questions about AI. It is certainly the topic of the hour and I would like to provide a few caveats and I’ll do that by leading in with a question. How many of you invested in or even know of, Diamond Rio? Diamond Rio? Anyone? MPMan F10? Come on, now. You guys must remember MPMan F10. These are MP3 players that predated the iPod. And Jobs famously changed it from “speeds and feeds” into “1,000 songs in your pocket.” Also, had the industrial design engineering supply chain wizardry, along with his marketing genius, of course, all to bring to bear on this thing called the iPod, which then produced, you guessed it, some of you wizened, gray-haired folks, but youngsters not realizing iPod leads to podcasting.
Yes. That was the genesis of this podcasting term. And the reason I bring this up is that I do not consider myself a bleeding edge investor or even in a lot of instances, a bleeding edge user. I like to be on the dull edge. And I would say that the iPod is a great example of that because if you looked at some of the technological trend lines, you looked at a few different pieces of hardware that had somewhat de-risked solid-state MP3 players. The timing was right for something to be taken from very, very niche and unwieldy to mainstream. And certainly, we’ve seen that unfold. And I view AI very similarly. And in some respects, it is very amenable to that approach because things are changing so incredibly quickly. If you hated a model three weeks ago, it might do exactly what you need today.
And with all of that, I just want to say I do not view myself as an AI expert. I think if you’re looking for someone who seems to be the Nostradamus of AI, you should read up on Leopold Aschenbrenner. You can look up “Situational Awareness: The Decade Ahead.” It was penned and published online June 2024. And the number of actual hits, predictive hits that Leopold had is staggering. It is just really about as close to clairvoyant as you could possibly be. So Leopold Aschenbrenner, and you check him out, if you’re looking for what’s coming. If you’re looking for what I have observed personally as a muggle, someone who is non-technical, I’m not writing white papers, but I get to watch a very large audience and I have a lot of friends I can lean on, many of whom are technical, I can fill you in. All right. That’s a whole lot of preamble. So let’s hop into it.
All right. First question is from Hugo. “In a world full of tools, systems, and AI, what human abilities or habits are becoming more valuable, not less?” So I’ll try to keep this pretty short. I would say the relational, the tactile, anything IRL, in real life, that can be extended also to, for instance, in my case, informational advantage, offline informational advantage. A lot of the LLMs are slicing and dicing the internet. One might argue all of them are doing that. And whether you are looking at longevity in professional terms, if you’re looking at longevity in creative terms, I think putting on the lens of looking at what you can do in IRL that currently, now that certainly robotics are on the edge of some type of Cambrian explosion, so who knows, maybe it’s iRobot three years from now, but for now, the kind of offline differentiator is a big deal.
And I would say the relational side, certainly the harnessing of awe, wonder, et cetera, nature immersion, which sounds like I’m suggesting everybody disappear off into a commune in the woods or become homesteaders or something. That’s not what I’m saying. But for instance, the fact that I have people I can text for very narrow types of expertise, even though they have the access of a generalist, allows me to have an informational advantage because none of that is online. Conversely, if you’re using ChatGPT or Claude to try to assess a given public company as a good or a bad investment or somewhere in between, you can rest assured that many, many people, perhaps even millions of people have already done this, and therefore you’re going to be reading more or less the same thing as many others. So that’s my stab at that first question. A lot of this is going to boomerang back in future notes. Let me take a sip of my sipping ketones. Excuse me.
This was sent to me by a scientist and he was like, “Mix 10 milliliters into 250 milliliters of water. DO NOT CHUG,” in all caps, written with a marker on this experimental container of ketones. So, we’ll see. If I start seizuring, it’ll make for a great short on social media.
All right. Next question I’m going to take a stab at is, this is from Jeff. “With a pre-throat clearing, not financial advice ‘disclaimer’ already granted to you by virtue of this question, where should a small investor be looking to invest in public markets as AI continues to eat our white collar jobs in the coming months and years?” All right. I know I indirectly already gave the caveat. I am not giving any investment advice because that is a terrible thing to do if you’re not a registered financial advisor and all that stuff. I’m none of those things.
So this is for informational purposes only. Number one, you shouldn’t gamble, and I do kind of view it as gambling, or invest anything you cannot afford to lose completely because AI is moving so incredibly quickly and there’s a lot of whipsaw reactivity in the markets. ChatGPT comes out with something that connects to some type of industry in an oblique way and suddenly six public stocks lose billions and tens of billions of dollars of market cap. There’s a lot of craziness. So as certainly has been said before me, the markets can remain irrational longer than you can remain solvent. So don’t play with anything you’re not willing to lose. There are people talking about what’s been termed halo trades, trying to look for things that are less likely to get disrupted or destroyed, kind of the Warren Buffett approach to non-tech investing by and large, seize candy, railways, et cetera.
But I would say that, initially sparked by conversations with Kevin Rose, and I hesitate to even mention this, but I do think Google is in a very interesting position, Alphabet, the artist formerly known as Google. Alphabet is in an interesting position to, in some respects, kind of own the full stack. Engineers aren’t going to like that I’m using that term, but they have distribution, they have hardware in terms of TPUs. They have incredible, unparalleled access to information. They’ve got Demis Hassabis and DeepMind internally. They’ve got the ability to spin things out like Waymo. There’s just so much going on within Alphabet that I find it very fun and terrifying to take a close look at. And I say that also because it is completely unclear, I would say, how exactly Google compensates for or plans for shifting to some type of ad revenue from AI generated responses or an AI-based, LLM-based platform versus what we use today in the browser, right?
And that’s inevitably going to happen. So the bull case is very exciting for Google and the bear case is also pretty compelling, I would say. But as I’m looking at stuff out there, I tend not to screw around in the public markets. I just don’t feel like I have any advantage whatsoever compared to everybody else who’s fine slicing things. But in conversations with friends and looking at it pretty closely, I do think Alphabet’s pretty interesting. So there you have it. I’m not saying invest in it. You could really lose money and it might be that they lose for a while until they win. It could be they lose completely. So there is that.
Next question’s from David. “What are the top three things you should never use AI for?” I would say any skill you want to preserve in your head, you should probably not use AI for. So I use AI for editing right now. You very quickly end up on a slippery slope. So if I create a rough draft as I did with the self-help trap, for instance, I would then take that, feed it into these models, and give them a personality. You are an editor from The New Yorker. This is your name, right? Maybe it’s a famous editor or the person who worked with Robert Caro, whatever it might be. I mean, that’s, again, not to compare myself to those people, but I want a good editor.
Give me feedback on this rough draft. What the model will do, because I want to keep you using the model, of course, is it will give you all the feedback and then it will say, “Would you like me to incorporate all of these changes and draft a version that uses all these things?” And that’s where I have deliberately hesitated. I’ve also played around with it, and frankly, it’s very good, but therein lies the danger because if you want to preserve your ability to synthesize, and this will tie into questions shortly about creativity, I do think that it makes some sense to exercise caution, and there are already scientists and researchers looking at the negative cognitive impacts of depending on AI, much like your ability to navigate has probably deteriorated since using Google Maps. And I would say net, each individual is more enhanced, augmented using these tools.
But if you do want to keep certain muscles strong and able, that’s where I would hesitate. And look, you can always change your mind later, but if you lose it, it’s a hell of a lot harder to reclaim it. So that’s where I am at the moment.
Oh, CJ. CJ’s question. “Do you, Tim, think AI is capable of creativity in the sense that humans are?” Well, I would argue here, and I’ve read all these books on creativity, I’ve looked at some research, which tends to be pretty soft, I would say. If I were being less generous, hand wavy about creativity or flow. I mean, I feel like a lot of these are poorly defined. So we could even go so far as to say, I don’t think we understand what creativity is in humans, right?
Could machines have the equivalent of the muse visit them? Is there a way to engineer that? When we create these metaphors for ourselves, are we really just using poetry or abstraction to try to verbalize something that’s actually pretty discreet and replicable if you just operate from a sort of bottoms up approach with reinforcement learning and this, that, and the other thing? Maybe. I just don’t know.
The second question that CJ had though is the one that I think is worth not necessarily spending more time on, but I would underline this because I underline it for myself. “As a writer and with the explosion of AI-generated content out there now, how do you rise above the noise?” All right. It’s pretty simple and I will answer that by way of a story. I was spending time, a little bit of time, drinking a Paloma with a very well-known photographer. He is one of the most commercially successful photographers in the world, and he was laughing and telling a story of how he gets approached by photographers.
They could be amateur, but very often they’re professionals who want to know how they can become better photographers and they’re asking all of these gear related questions. And his answer is, just put more interesting stuff in front of the camera, make what’s in front of the camera more interesting. And the equivalent of that, at least for me as a nonfiction writer, is doing interesting things. Go out in the world, do interesting things, or observe interesting things in real life and write about those things, do experiments, et cetera. I mean, there are many ways to skin this cat. It could be, let’s just say, Travels with Charley, amazing book by John Steinbeck, road trip in a makeshift RV with his dog, Charley.
All right. Incredible book. And as it stands right now, I think it’s a ways off that a humanoid robot is going to get into a car with a canine companion, robotic or flesh and bone, and do something like this. Anything that is analysis-based is relegated to the machines at this point. They’re so good. The AI, broadly speaking, LLMs being one manifestation of that, are just too good. They’re so good. And we’ll talk about how I use some of those tools a little bit later. So do interesting things and write about them. That’s the short answer. All right. There are certain questions where I don’t feel like I have good answers or informed answers. I could make up some bullshit and spin a yarn and make something that seems to hold water, but I’m not going to do that. So I’m going to — I apologize if I’m skipping some of your questions, but I don’t want to give you any type of false confidence in my answers.
All right. So this is a question from Maneal. “How are you keeping up with all the new AI tools? Where do you keep your focus? Have you set up OpenClaw, and if so, what’s your workflow?” Okay. So, I am not keeping up with AI developments. People who do this full-time as the C-suite executive teams of the best known companies in the world have trouble keeping up. So I am definitely not keeping up or trying to keep up. I feel like as soon as I’m doing that, I’ve already lost. So, it’s not how do I win the game, it’s choosing the right game, which might sound cliched, but does that mean I’m ignoring everything? No. With something like OpenClaw, due to security concerns, I let friends of mine be the first — elect to be some of the first monkeys shot into space. So I’m going to read from a friend of mine who I texted, right? This is about this question right before we started recording.
All right. So about OpenClaw, he played around with OpenClaw. His name is Chris Hutchins. He’s been on the podcast. He has a podcast called All the Hacks, which he has used to explore some really fascinating stuff. If you’re a points nerd or like travel, it’s a good one. He goes a lot further than that. But one of his episodes is “I Built an AI Assistant That Works While I Sleep,” and he explains what he did with OpenClaw. However, here’s what he texted to me. “In the last week, Claude’s desktop app has shipped a bunch of features that do a lot of what OpenClaw can do in a more user-friendly way, schedule tasks, remote access, et cetera. So that could be a good beginner way to start. But with all AI projects, I suggest going in with a use case.” This is, again, Chris texting, and then he documented his whole journey with building a basic app through OpenClaw, et cetera, et cetera, et cetera, and leveling up his knowledge each time. We’ll link to that episode in the show notes. You can find it pretty easily.
Here’s what he added to that. “For OpenClaw, I’d say you absolutely don’t need a fancy computer. I ran it on a 2012 Mac mini for the first few weeks, but if you have an old computer and you want to set it up and test it out at home, great, but until you feel confident, one, don’t give it access to things like email, credit cards, et cetera.” And there are some hilariously tragic stories of this gone awry that you can find on your own. Okay, that was my director’s commentary. “Two, don’t install random skills you find on the internet. Three, go to Claude, ChatGPT, et cetera, and get advice about how to set it up securely. Four, every time I’ve gotten stuck, I’ve been able to use Claude Code in the OpenClaw Directory to fix things.” So there you have it. That is by virtue of texting Chris Hutchins, an answer on OpenClaw.
And what I could also do is give some examples of, internally, how we’re using stuff. So I have an employee who is very interested in these tools and I have wanted to encourage that as long as we’re not completely demolishing our own security from the inside out. So he’s played a lot with Claude Code and other things. And I asked him for some use cases that I could share with you. So I will pull those up right now. All right. And this alludes to a term, defines a term that Chris used. All right. So one thing I did — this is my employee. “One thing I did earlier today was build a skill, quote, unquote, “skill,” fancy name for a text file. In this case, inside Claude that will generate the PDF and Word versions of an IO, that’s an insertion order for a podcast sponsor, if I only give it the missing items from the IO, for instance, company name, official company name,” da, da, da, da.
“It fills it out automatically and creates a PDF. It’s a small save in time,” but this is something he repeats a lot, “and there may be a better way to do it, like a template and HelloSign or something.” I also have been working on a project doing a 20-year, roughly 20-year retrospective deep dive and analysis of all my angel investing, right? Are the stories I tell myself about my report card accurate? Are they completely false? Are they somewhere in between, et cetera, et cetera. And for that project, coming back to his text here, it’s been really crazy to just tell it, quote, “Here’s an API key,” and it will figure out how to connect to a given service like Gmail. And if you have an API key for a product, you can easily start using it in Claude as it will simply write itself a script. And one of the wildest things, and this is — I’m paraphrasing here, but it can ingest an absurd amount of data and convert it into something useful, and it can also enrich data in some very interesting ways, right?
So if I’m trying to figure out, okay, via email introductions, who introduced the winners, who introduced the losers, who introduced the zombies that just can’t seem to die after years of struggling, or take off for that matter? And then is there a signal, say, looking at the education levels, the schools, the alma maters of founders? What about single founders versus two founders versus three founders? Things like this. Location, geography, blah, blah, blah, blah, blah, blah, blah, is there any signal to any of this?
Another example, which might apply to more of you, the Google Calendar integration has also been helpful. In other words, updating a calendar entry from Claude or creating multiple at a time, so using Claude to add calendar entries. Now, in my case, I have a bunch of different calendars and different people on my team add to different calendars. One thing that helps us a lot, and maybe someday I’ll share this. For right now, I’m probably not going to, but I have a document, a Google Doc that is the 10 commandments of my calendar basically, and it’s rules around formatting, what to include, et cetera. Secondary points of contact, cell phones, time zone always indicated in the headline, et cetera, et cetera, et cetera. There are lots of different rules, but he can use that or other people on my team can use that to then automatically check calendar entries through Claude Code and fix them as needed.
So some people have joked that The 4-Hour Workweek should be rewritten as The 4-Minute Workweek. I think there’s something to it, and there’s a temptation to do an entire section on use of AI in place of virtual assistants and so on. The problem with that is that as soon as the ink had metaphorically dried on that paper, it would already be out of date, so I’m not going to do that, I don’t think. So there you have it, and the API key is a really important component to all of this.
Also, and I’m sure some of you have figured this out, but with Claude Code, and Chris Hutchins alluded to this as well, for debugging, for instance, we did a website redesign and there was an issue with a form, no idea why, and we wanted to fix it very quickly and we weren’t sure how long it would take for support to get back to us. So he was able to dump all the code at the time into the model and just figured out how to fix it, and there are many, many, many other examples of that. Yeah. And many of these things are not quantum leaps, but they are, much like anything else, just automating little paper cuts so they don’t add up ultimately to a huge gash in your calendar.
Okay. Back to work, Tim Ferriss. All right, let’s look at other things. This is a question from Becky. “What would you say to someone who wants a career jump? Sometimes I feel I get caught in a loop of same pay range, same experiences, same mid-level opportunities. How can I start increasing my income opportunities and skills this year?”
Okay. So I reached out, as I often do, texted a couple of people about this, because this is going to be a huge, huge, mega, mega, meta problem for people moving forward, and it’s going to increasingly, I think, be pervasive. People are going to wonder what they should do next, which then informs upskilling. And there’s a later question so I might as well explore it here related to encodings in the Jim Collins episode, question around encodings. And I might come back to that, but suffice to say, some of these personality tests and things like Enneagram are actually very helpful, and things like StrengthsFinder and so on.
And there are two startups I’m involved with because I recognize just through questions like this from Becky, which are the canary in the coal mine. It’s not really a canary in a coal mine. It’s like there was one whisper, now there are 10, then there were 100, now there are a thousand. This question is coming up more and more, and a lot of folks are going to, in one way or another, need to zig and zag, even though they might not expect it right now, and a lot of that’s going to be due to AI job displacement.
So the two startups that — and again, I mentioned that I’m an investor in these so I’m biased, but the reason that I invested in these is to answer this question, or more specifically, to help people answer this question. So the first one is called Apt, A-P-T, and you can check that out at tryapt.ai. So Tryapt, T-R-Y-A-P-T.ai. I had the co-founder and CEO create a code, so if any of you guys want to try it, ultimately, it does cost money to get all the results and to get this AI-guided mentor around your strengths and so on, which you discover or uncover through the process of going through this. But you can get 50 percent off with TIM50. That’s the code to use. T-I-M-5-0. All right. So if you want to take a look at that, you can check it out.
The other is Oboe, so OBOE.com, and that is entirely focused on accelerating skill acquisition and learning. So I think these two actually go together really well. You could use Apt first and then Oboe, and I’ve played around with both. There’s a lot that’s going to be coming into both of these, but might be worth checking out. Honestly, if I were to tell you to go buy What Color Is My Parachute or something, you might glean something from that, but I feel like in very dynamic times, with so much shifting sand with respect to technology, you probably need something a bit more or benefit from something that is more dynamic and personalized from the get go, as opposed to you having to do lots and lots of heavy lifting with a fixed format. So that’s what I would say, Becky, and definitely let me know what you think, because if something’s broken or if you love something or you hate something, all that stuff can get fixed.
All right, next one. This is from Jeff, and we will do some live questions. These ketones are actually doing something, which is good because it’s 4:00 p.m. and I don’t want to have any caffeine. Yeah, fortunately, it doesn’t taste too much like jet fuel.
All right. Let me do one more. Jeff. Okay, this is the question.
“You’ve worked across books, podcasts, and experiments that each attracted their own communities. What have you learned about proactively shaping a community’s culture, not just growing an audience? And how has direct interaction with people changed the way you enter creative flow today?”
The last piece is probably the hardest answer, but I can tell you that I think that proactively shaping a community’s culture actually helps you to build an audience, but to what end? Not build an audience like, oh, I’m aiming for two million, three million, 10 million YouTube subscribers. I don’t like renting audience in a way that’s dependent on algorithms, and you can look at a lot of the biggest YouTube channels. Their average views per video have cratered, even though they have huge numbers of subscribers. You see that with engagement on X and other places.
However, one thing that never goes out of style is “1,000 True Fans” by Kevin Kelly. You can read it for free at kk.org, and therefore, I will focus on the proactively shaping a community’s culture. In my case, I think it’s pretty simple. I treat a closed community like I would a dinner party at my house. So somebody walks into my house, and this is a shoes free house, because who wants dog shit and bubble gum on your kitchen floor? I don’t, so the shoes come off at the door. So let’s say somebody comes in and they’re like, “No, I’m keeping my boots on.” They come in tracking mud all over the place. They sit down at the dinner table, they kick their feet up on the table and start calling people assholes or something. That person’s going to get dragged by their hair out and then they’re never coming back in.
So that’s a bit of maybe a melodramatic example, but zero tolerance policy for broken windows. Even Malcolm Gladwell and others have written about this, but when these minor infractions are permitted, I’m going to pull out a fancy term that tech people like, the Overton window, the broadness of what is now allowable behavior shift? Or I shouldn’t say shift. It’s a fucking window. It’s not supposed to get wider or shorter, but it moves in a more aggressive behavioral direction. So if you allow minor infractions, you’re going to get moderate infractions. You allow those, you’re going to get major infractions.
So from the very first days of, say, the blog, the comments section has guidelines and it’s like, Remember the Fonzie? We’re going to be cool, like that. If you’re an asshole, we’re going to boot you and blacklist you, and you can criticize me but don’t be a dick to other people, and if you are, you’re gone. It’s zero tolerance and you have to enforce that. If you don’t, people are crafty. They’ll learn how to manipulate you because you are asking to be at least abused by not enforcing your own rules. So that’s the first one. You have to excise the cancers and remove the poison. You just have to, because the default state of pretty much the entire internet now, because it’s been allowed and encouraged through various gamifications on social platforms, is just being loud, obnoxious, awful, so you have to set rules to counterveil that.
Also, and Jeff, I think you’ve experienced this, if you have a private community of a hundred people or 200 people or 50, it doesn’t really matter, and you charge $5 a quarter, $5 a year, it doesn’t really matter, but if you have some very nominal costs, people opt in who generally want to contribute and be in an environment of positivity. That’s my experience generally. So having some very, very nominal fee at the door I think is incredibly helpful, and you find that also with events.
I’ve done plenty of live events, don’t really do them anymore for a lot of reasons, but very, very rarely in the past, I would throw these live events for book launch parties, hundred people, 200. If people can RSVP to an event, your abandonment rate or no show rate is going to be sky-high. If you force them to pay $1 to hold their spot, suddenly the no show rate goes down to low single digits. So I don’t think there’s any rocket science here, but the tough part is being willing to enforce, and maybe you give someone a two strikes or out policy, but frankly, I find that that can metastasize.
For instance, I have a lovely dog. It was a stray two months ago, adopted her, and she’s really smart. She’s part Anatolian Shepherd, it would seem, and if she realizes, for instance, that she can pit me against my partner and that she doesn’t actually have to listen to sit until the third time, she’s not going to listen to the first two. She’ll just stare at you defiantly and then sit the third time. Humans are the same way. They’ll do that too. If they know they have two strikes, you’re going to get more bad behavior because they know they can get away with it once.
All right, so there you go, and let’s go to — we’ve got plenty more questions, but I am going to — let’s go live to some live questions, and I apologize that there’s so much in the chat, so I’m going to have to — oh, yeah, the crown means top fans. All right. Well, thank you. Thank you, top fan. All right, let’s throw out some live questions and I’ll give it a shot. If you already posted one, please post again because I can’t scroll up and go through hundreds and hundreds and hundreds.
Favorite color? Green, right there. Green, green, green. Specifically, it’s the color of late morning light, like 11:00 a.m. sunlight around August coming through maple leaves. That is the color, the sort of translucent green. All right.
Future of Varlata. Okay, for those who don’t know. Also Coyote. Coyote continues to do really well. I feel like I have done mostly what I can do with Coyote at this point, and it’s in steady state. The reviews on Amazon and elsewhere are great. It continues to sell well through the distribution channels. I wish in retrospect, earlier on, I had really focused on, even though there are plenty of adults who enjoy it, focusing on families that have at least one or two kids in that eight to 15 range, and that would have helped with escape velocity sooner, but hindsight 20/20. I’m really, really happy with how it’s turned out.
And then Varlata, honestly, now that the AI tools are getting good enough, about six months ago, I was planning on creating a movie trailer for effectively a script, I’ve got the whole thing in my head, focused on Tyrolean. If anyone — this is The Legend of Cockpunch. Now I think I will, for obvious reasons, lean towards Legends of Varlata, but focusing on the relationship between Ty and his father and all sorts of craziness that ensues. So I’ve got a whole movie script in my head and concept art that I haven’t really done anything with from some of the top Magic: The Gathering and D&D artists you can imagine, so we’ll see. We’ll see. I could see screwing around with that this summer.
Yes, shout out to Jeff for keeping the CP community humming. Happy to spend some time there as well. All right.
“If I could only pick from the books on the shelves behind you, what book would you want everyone in this group to deep dive into or dive deep into?”
Man, I have those books up there for a reason. I have thousands of books. I’ve donated most of them. These are the ones I keep up for me to look at. Give me a second. I’ll tell you. Okay, great. So I’m going to give answers that may not be satisfying to some folks, but that’s okay. I’ll give you one that I suppose you might expect from me. So one is going to be The Effective Executive from Peter Drucker, classic, old, short, incredible bang for the buck. However, the other books, I would say, again, talking about what you do in a world of AI, do more interesting things. There’s a book back there called Of Wolves and Men by Barry Lopez, who won, I believe it was the Booker or Pulitzer Prize for another of his books called Arctic Dreams. Of Wolves and Men is one of the best nonfiction books I’ve ever read, and it really shattered the mold. It redefined what, let’s just call it nonfiction nature writing could be. It’s just an incredible, incredible book. So there’s one, but again, this is choose your own adventure, pick and choose.
Travels with Charley by John Steinbeck, I mentioned it earlier, is hilarious. Also an incredibly accurate and enjoyable, warts and all, ride through the US. What a quirky, weird-ass country. So that’s another one, pretty fast read. And then there are entire shelves back there related to animal tracking and so on, because I’ve done a bunch of that. I don’t think most of you should probably spend a lot of time on that.
If you haven’t read, I’ll simplify the title here, Alice in Wonderland, you should go read Alice in Wonderland. Read the whole thing, not just quotes from it. I have a collector’s edition back there. And then there are a few actually that I was going to mention for one of the questions you guys submitted as an answer. The 80/20 Principle, Richard Koch, that just never gets old. It just does not get old, and there’s another book of his up there called Living the 80/20 Principle. It might be Living the 80/20 Way, but he really walks the talk, and if you haven’t heard my podcast with Richard Koch, K-O-C-H, he’s also one of the best investors I’ve ever met. He’s had, I don’t know if he’s disclosed the actual amount, but he is — I know a lot of the world’s best investors and he is quietly way up there in the pantheon. So also a practitioner, he’s on the field, so worth paying attention to him.
All right, Of all the places I’ve traveled to, which have been the most breathtaking? There are so many. Queenstown, New Zealand at the right time of year I think is incredible, but you name it, you name it. I think Upstate New York honestly, The Gunks and that entire region where a lot of The Last of the Mohicans, the book certainly, I don’t know about the filming of the movie, but that takes place in that region. You can put me anywhere. I think so many places are beautiful. Take a couple of drawing classes. That makes things much more beautiful overall, like gesture drawing classes. Get some live nudes, keep it interesting. You may get an obese dude with his schwanz all over the place, so just so you know, it’s not automatically going to be a Victoria’s Secret model, but that’s okay. Can’t win them all.
All right. This is from Hilca. All right. I’ll abbreviate a bit because this was a long question. I’m only going to hit the first part here, but, “I’m a bootstrap founder in Replit’s Race to Revenue flying into San Francisco next week to pitch and network for a few days. If you were in my shoes and wanted to squeeze the maximum long-term leverage out of that short trip, what specific things would you do before, during, and after the event to, one, have the right conversations, and two, turn them into real opportunities rather than just great chats?” Okay. “Bonus, how has your bootstrapped versus VC changed lately for tech software?”
I think it’s just getting cheaper and cheaper to make software, so I think we’re going to see a lot of self-funded startups. Good news, barrier to entry technically, also economically is much lower. Bad news, the barrier to attention and actually getting people to use your stuff has never been higher. So there is that, but I do think that we’re going to see huge self-funded bootstrap companies, assuming that there aren’t just a few gods, AKA, super intelligence AI beasts that eat everything. All right.
But coming back to your question about network, this has also never been more true, I think, in real-life wins. Everything else is too crowded. So there is a talk I gave. I don’t think there’s any video. You don’t need video, frankly, but there was a talk I gave at South by Southwest, we’ll link to this in the show notes, but if you search my name and “How to Build a World-Class Network in Record Time,” this will pop up. This is a talk I gave, who knows, seven years ago, 10 years ago at South by Southwest describing exactly what I did at South by Southwest 2007 when I launched The 4-Hour Workweek. And my entire budget for that book for launch and marketing and so on was spent on a few trips to, I think it was Web Summit, maybe something expo, Blog Expo, and then South by Southwest.
And there’s an approach described in that that I think is very, very effective, and it’s still surprising to me no matter how many times I talk about certain things, people just don’t follow it. If I’m like, “Hey…” If I wanted to shill some shitcoin and be like, “It’s going to the moon,” people would buy it immediately. But if I’m like, “Hey, here’s this thing. It actually takes some hard thinking and you need to plan for it, but it’s so much more effective long term than all of this hustle culture bullshit three-card monte that you want to do every day for 10 hours,” it’s like the upfront stuff really matters a lot.
In this case, I really recommend this talk, “How to Build a World-Class Network in Record Time.” And that sounds like YouTube clickbait, but it’s actually true. A lot of friends, who are still friends of mine almost 20 years later, came from South by Southwest 2007, and a couple of those events I flew to. These were not just transactional interactions. And there is a way to approach this. You definitely need to study any sessions and attendees beforehand.
The good news is — good news, bad news — is that — have the right conversations? You don’t need to worry about. You have no idea how to have the right conversations. Your goal is to meet people who are hopefully world-class at what they do, simpatico with you, meaning you guys will actually get along. Could be extracurricular interests, side hobbies. It could just be the way the two of you are programmed. And there are other kind of general strategies, like talking to moderators of panels instead of the panelists. Everybody floods the panelists. The moderator gets orphaned. And in many cases, the moderator is just as impressive, and certainly the moderator knows everybody on the panel and lots of people on other panels and everywhere else. So there are a couple of tips in that that I would suggest checking out.
All right. Next question’s from Alex. “My company’s growing quickly. There are a lot of things that I need to be doing to hit escape velocity and be able to hire to manage at the top.” I think that’s manage. It says “mange,” but I assume you don’t want mange. “How do I choose what not to do?”
All right. Well, the good news is we already talked about a couple. So 80/20 Principle, Richard Koch, I would read that. The Effective Executive, absolutely read that, and it’s really going to give you frameworks for better discerning yourself what to do and not do. The other, depending on the scope, current scope and scale of the company and then the ambitions, especially if it’s venture-backed, is to read a book called The High Growth Handbook by Elad Gil, E-L-A-D G-I-L. Arguably, one of the best certainly, angel investors in the last few decades. I mean, his hit rate is absolutely insane. He’s invested in at least 40 unicorns, also a tremendous founder and operator in his own right. You can check him out. Has a pretty wicked biology background on top of everything else. So those are a few that come to mind.
And then maybe last but not least, it’s been a long time since I read it, but The Blue Ocean Strategy, probably worth checking out. Because if you choose to compete in a crowded category, you just have a harder road ahead of you. So creating a category of one in a sense, much like Cirque du Soleil back in the day. I’m expecting you’re not dealing with Eastern European acrobats, but you get the idea.
All right. This is from JC. “When exploring somatic or psychedelic healing spaces, what specific questions or observations do you use to quickly distinguish between a highly competent, grounded practitioner and a narcissistic guru?” Tough. A lot of good actors out there.
The first thing that comes to mind, and obviously with all the usual caveats, these things are powerful, you can definitely destabilize yourself, they’re illegal in most places, et cetera, so don’t break any laws, talk to your doctor, blah, blah, blah, but you could ask practitioners or you could ask someone who’s had two trips and they’re suddenly acting like a messiah proselytizing everybody. You could ask them the same question. But specific to clinicians or practitioners, ask them what types of adverse events they’ve seen. What are the most concerning adverse events that they’ve seen?
A simple way to put that is, how do you handle freakouts? What do you do when somebody really loses their shit? And if their answer is, “People don’t lose their shit. There aren’t any adverse events,” they’re either lying, delusional, or very inexperienced. Maybe all three. Those are not mutually exclusive. So I find that to be a pretty quick, necessary but not sufficient way to use a particular line of questioning to separate seasoned practitioners who are honest from those who are neither of those things.
Of course, do your own homework. I don’t think anyone who’s new to this, and by new, I mean, they have not been doing it more than a decade, ideally multiple decades, makes the fly list for me. It’s just become too goddamn trendy. So I would just say, probably unfairly, but I would be biased towards people who have been doing this since before Michael Pollan’s exceptional book, How to Change Your Mind. That might be the cutoff for before and after.
Let’s go back to live questions.
Yeah, Kumaré. Great documentary. Fred recommended. Everybody should watch Kumaré. K-U-M-A-R-E. I won’t ruin the surprise. Check that out. It’s a great film. I liked it so much that way back in the day, there was a startup called quarterly.co, which sent out boxes of goodies to people who subscribed, and I would hand-curate all these things that I really liked. It was kind of like a 5-Bullet Friday, but on a quarterly basis where you get all my favorite things shipped to you in a box. Very difficult business to make work. But at one point, this also dates me, it tells you how long ago it was, I reached out to the filmmaker who made Kumaré and we figured out a way to make it work that I would ship something like 3,000 USB drives, each of which contain this movie, to my subscribers. That was one of my items that I sent. All right.
All right. Lots of questions about conferences. I don’t have a particular take on conferences these days. I apologize. I’m not tracking it actively. There are always interesting meeting places in person, so I don’t believe that’s outdated. South by Southwest has gotten very large and quite corporate. Doesn’t mean you can’t have interesting interactions, but I would look for the events ideally that are fewer than a thousand people, fewer than 500 even better, if you can.
All right. It’s from Chris. If I “weren’t an author and podcaster, what other careers or industries would you have pursued?” I wanted to be a comic book penciller for ages, and still do. Some, actually, of my art pads right back over there where I love to do live gesture drawings, honestly. It helps me get out of my head. Somebody will be up there, they’ll hold a pose for like 60 seconds at a time and then change, or two minutes or five minutes at a time. You really can’t get in your head. There’s just not enough time for it. So I really, really enjoy that. But I wanted to be a comic book penciller and was an illustrator through a good part of college, helping to pay for expenses, things like that, illustrating books and so on. So the prospects then were not very attractive financially to do that, especially after my extended family paid a fortune on my education. So I shifted gears, but certainly felt a draw towards that.
“What kind of dog is Molly?” Molly is a rescue mutt. She is a Labrador, Bloodhound, and a Pit Bull mix. Then I’m sure there’s a Heinz 57 of other breeds in there.
In terms of training, honestly, I put up some basic training videos on YouTube if you just search my name and dog training, but the books that I have found most helpful are Don’t Shoot the Dog by Karen Pryor. I think everybody should read that. I think the back copy says something like, “Whether you want to stop your cat from jumping on the table, train your dog to do X, or convince your mother-in-law to stop nagging you, the instructions are all the same.” It’s something like that. It’s pretty funny. But Karen Pryor brought clicker training, audible cueing of that type, from marine mammal training, dolphins, orcas, et cetera, to dog training, or at least she’s one of the people responsible for that. Really fantastic book on behavioral change and shaping behavior overall.
And then listen to my podcast with Susan Garrett. Susan Garrett, G-A-R-R-E-T-T, is impressive because she has won, I want to say, I don’t know, five to 10 national dog agility championships, even though she herself is much older than most of the human competitors who have to kind of run alongside their dogs, and she really, really knows her stuff. So those would be, I would say, two places that you can start, two or three places. All right.
All right. Well, very kind comment here. “All of your works hold so many lessons on protection and nourishment, the root of being a father.” I feel that way. Thank you. My friends have been, my closest friends are like, “Yeah, you know what? You’re going to be a great dad.” So that’s part of the reason why I’m headed that way, even though word on the internet is that I’ve self-helped optimized myself into being single and miserable. That’s not true. So all those trolls can suck a dick. It makes me feel like I’m drinking tequila. Beware of those ketones, guys.
All right. More on my thoughts, this is from Cindy, on Enneagram, dating, and business peeps. I think Enneagram, look, it might be tech-friendly astrology, but I’ve seen it used at Shopify. I’ve seen it used at Dropbox. I’ve seen it used by more than one person to meet very good matches in intimate relationships, and I think there’s something to it. I mean, it is a tool. I would say that I try to be as tool-agnostic as possible, but I found the Enneagram, and there are other options, of course, as one good option for identifying your own blind spots for, say, your partner, and this could be someone you work with, a superior, subordinate, colleague, what your likely blind spots are, where you’re likely to be oversensitive, and therefore how you might want to handle things internally, like meetings, decision-making, conflict resolution. And that’s pretty interesting, and it has been tested on a pretty large scale within places like Shopify and Dropbox, unlike many other things.
So I find it interesting and the app that I mentioned earlier, tryapt.ai, code Tim50 for 50 percent off. I don’t get any affiliate kickback or anything. That’s just to save you guys some money. They incorporate the Enneagram, so, pretty interesting. I was telling them, I was like, “Hey, once you figure out this kind of business career mentoring side, you could very easily have a matchmaking capability built into it.” All right.
Quantum computing I find fascinating, amazing, and terrifying in equal measure. I have not done much in the quantum computing world. I have looked at maybe how certain cryptocurrencies are more prepared to be quantum-resistant than others. I’ve looked at stuff like that. I mean, not to mention all of our other fancy passwords that we currently use and security, but I have not really gone super deep. I feel like that’s an area, much like fusion, where you really want to be as technical as possible wading into those waters. I did a podcast with Steve Jurvetson ages ago, who was one of the first investors in D-Wave, but yeah, I mean, people are talking about AI, but man, when quantum actually hits —
And the joke has been with fusion, for instance, that fusion is always 30 years away. I don’t think that’s true anymore. Now, I could be proven wrong, but I also think that’s true with quantum where people are like, “Yeah, yeah, yeah, that shit’s never going to work.” I’m like, “Ah, we’ll see.” Look at Google’s — excuse me. Look at Alphabet’s investments into quantum computing. It does raise some questions. Very interesting and also pretty scary to imagine what post-quantum looks like. All right.
Bear with. This is a good question. “How do you maintain so many friends despite your countercultural ideologies?” My friends and I, I think, have maybe implicitly, and this is maybe survivorship bias, but agreed that as long as you’re civil, you can disagree on all sorts of stuff, and I surround myself with friends who are going to push back. And this includes my oldest friends. This isn’t just like fancy friends that I’ve accumulated since the podcast or anything. This also applies to my oldest friends from high school and college.
So I would also say that most of my friends are pretty adaptable in light of new information, but if some — I don’t spend a lot of time around blowhards who are like, “I’m an X, I’m a Y. I’m a liberal and that person’s a neocon,” or, “I’m a conservative and that person’s a libtard,” or whatever. I don’t hang out with those folks because that, while I recognize that level of simplicity is appealing in a very chaotic, messy world, it’s not particularly an accurate reflection of reality and the gradations in between extremes and it’s certainly not very helpful unless you are playing the political game and that’s just a quiver, an arrow in the quiver that you have to use.
But otherwise, I just stay away from that stuff, which doesn’t mean I don’t — I certainly don’t steer away from controversy, but I ask myself, “Is this…” And this applies to watching news or social media.
And I know I’ve said this before, but I haven’t had any social media apps on my phone for probably three or four years. And the way I feel about the news in The 4-Hour Workweek is probably 10x more intense now in terms of my selective ignorance around mainlining “news.” Because if it’s not relevant to your life and if you are not going to make a decision differently or take action because of it, or maybe avoid action because of it, if there isn’t some kind of follow-up, you don’t need it is my general feeling.
And that’s going to become not just a, maybe, perceived luxury. I’ve been doing this for decades now, and I wouldn’t consider myself ineffective in the world, but it’s going to become a survival imperative. If you want to remain sane, you can’t doomscroll 24/7. There’s no way. You can’t doomscroll even a few hours a day. So I’ve seen some crazy, crazy physiological data from people on and off of social media, like blood tests and mental health assessments and so on, like HAM-D, CAPS-5, all this kind of stuff. It’s not good, guys.
So I’m getting up on my soapbox now, but yeah, and we were talking about that no-asshole rule. Just because someone disagrees with you does not mean they’re an asshole, but if someone is really throwing sharp elbows for no reason, it’s like they’re out. I very freely have an inflow and outflow of friends. There are certain friends who have remained in the inner sanctum, and I for them too because they reserve the same right, for years and decades and decades now, but it’s like — and people are allowed to have off days, but it’s like if someone has suddenly adopted being an asshole as part of their personality or identity in service of “keeping it real” or something, I don’t have time for that. All right.
Let’s see. Somebody asked about podcast interviewing a female screenwriter. Yeah, sure. Depends on the screenwriter, but was actually reaching out to two female screenwriters not too long ago. Don’t think I heard back. So what are you going to do? But let’s see.
Yes, this is a comment by Tim. “This sounds super simple, but my longest, latest relationships share a common sense of humor. Married for 33 years and that’s foundational. Same goes for oldest and longest-lasting friendships.” Yeah, 100 percent. Humor is just reflective of so many other qualities, and there’s a difference between humor and just like a kind of cynicism, quippy cynicism. I’m not so much into that, but if there’s a fast banter and people also are good at making fun of themselves, not all the time, but in the right dose, it generally bodes well.
What inspired my most recent blog post? @FugacityLabs. This is on “The Self-Help Trap: What I Learned from 20+ Years of ‘Optimizing’ Myself,” optimizing on quotation marks. Might’ve been improving. We split test a bunch of different headlines. But what prompted that is just seeing how, at worst, miserable, at best, constantly anxious or self-doubting so many people are in the self-help, self-development world, and I feel like we are all sitting on a slightly too-warm stovetop of baseline anxiety due to the technological tectonic plates that we’re dealing with, and certainly the kind of algo-driven personalized feeds that will just pour gasoline on your limbic system. And coming back to what we can control, it’s like, okay, sure, I can suggest people delete social media apps off of their phones. Realistically, most people are not going to do that. And there are some upsides. If you have the ability to moderate with these tools, you can stay connected with friends, et cetera, et cetera. Although I become more and more dubious of those defenses.
If people were able to, instead of just looking at screen time by app to see what actual usages, the use cases that they’re spending time on with a given app, I think that would be very illuminating. In any case, in lieu of that, what else can you do? What other levers can you pull? And I think the in-real-life relational component is the lever that makes all other levers easier in a way. So that’s what prompted writing that blog post. All right.
Very nice question. How can we help you, whether here or in the Discord book forum? Just try to be — go first with people, to quote Gabby Reece. I interviewed Gabby with Laird Hamilton, one of the kings of big-wave surfing, and I think her billboard answer was, “Go first. Just smile and say ‘hi’ first. Just do that.” I’d say helping the world to be just one percent brighter in some tiny way. Tip the breeze, like leave a $20 as a tip once a month somewhere. I know that’s not necessarily trivial money for folks, but it’s, like, give somebody an absurd tip. If they’re really good, really kind. Or it doesn’t even — like have a nice tea tip of a $10, right? Something like that. It doesn’t need to be money. You get the idea. All right.
Do I have any news to share about The No Book? Yeah. I’m going to put on my diving goggles and get back into it in the next probably month or two, pretty soon. I have a couple of other things, and I’ll have — I foresee at least one big announcement related to other projects coming up in the next few months, but going back in. Wish me luck.
Let’s see. Okay. Let me think about — this is a question from John. “Still love the 17 questions.” People can find those 17 questions. I think they’re in Tools of Titans, maybe Tribe of Mentors, but also on tim.blog. There’s a PDF with the 17 questions I most often ask myself.
“I’ve got one. A question that I would probably add is some version of ‘What is the most generous interpretation of this?’” I have been trained since a wee little lad to be pretty anger forward, let’s just say, if I were a wine. Very anger-forward. And the way that shows up, there are, to get fancy, myriad ways this shows up. One is that some days I can just feel like the entire world is conspiring to make me annoyed. And obviously that’s not true, right? But if it seems like someone is ripping you off, right? Which does happen. Most of the time, it’s probably just a misunderstanding.
So what’s the most generous interpretation? If you feel like your significant other did something to annoy you, or they always do X, they never do Y, like, okay, well, what’s the most generous interpretation of this? And I’m borrowing this from other people, but I feel like that is a very helpful question. And you could pair that with a bunch of other ones. I think Krista Tippett, great podcaster by the way, but Krista Tippett, one of the OGs, On Being, I believe, is her podcast. And I believe it’s Krista. I might be misattributing, but at least I’m not saying Oscar Wilde or Abe Lincoln that she said, “Anger is pain shown in public,” something like that. So you can apply that to yourself too if you’re a little anger-forward. And that doesn’t mean naval gaze, and you have to do 12 years of therapy to figure it out, but what is the most generous interpretation of this, whatever this might be? I would add that to my questions.
Let’s see. Okay. “If you go to a city and you have two days, what are your go-to activities?” Bicycle tour. Bike tour, for sure. One of the best ways to meet locals, figure out what’s fun that isn’t just a glossy photo posted on Instagram or a super expensive three Michelin star restaurant. Bicycle tour. Also hang out with — you don’t have to actually stay at a hostel, but go talk to the manager of a hostel or somebody who works the front desk and has been there for a couple of years. They’ll have lots of great recommendations.
Okay. Where does accumulating wealth fall on my scale of overall success? Zero. It’s like, look — I mean, a lot of wealthy people make a lot of excuses as to why they need to keep making money like, “Well, I could give money now, but if I compound at such and such, compound on an annual growth rate and da da da, and then I’ll give it away when I’m dead basically, or yada, yada, yada.” I just don’t buy it. Working dogs who have been chasing a rabbit around a track their whole lives in sixth gear get very good at chasing something at sixth gear, so they want to continue doing that.
I’m not holding myself up as some enlightened being. I’ve just had the benefit of seeing so many people crash and burn or just end up with this existential malaise because when they actually pause for a second, if they do pause, and sometimes life forces you to pause with a divorce or medical emergency. They have this maybe sense of hollowness or certainly not a sense of fulfillment. I’ve just seen that so many times. It’s like, “Accumulating wealth, who cares?” It’s just like, how many people can give you the full name of Alexander the Great? It’s like nobody’s going to remember you. Nobody’s going to remember me. Nobody’s going to remember us. It’s okay. It’s totally fine. It’s actually very freeing. It’s like everybody should read, I think it’s Percy Shelley, Ozymandias. I’ll let you guys — yeah, Percy Shelley, “Ozymandias.” Everybody should find this. O-Z-Y-M-A-N-D-I-A-S. So good. Everybody should read “Ozymandias.” All right.
All right, what do I prioritize instead of wealth? Relationships. And this sounds so trite, but it’s like there are people who say that and then you go visit them, and you’re like, “Holy shit, their kids hate them, and they never see their best friends.” Or their “best friends” are constantly a different roster because, as Arthur Brooks would put it, “They’re deal friends, not real friends,” right?
But I mean, the past year review really helps to make this point for me over and over again. And if you don’t know what the hell I’m talking about, just search my name and “past year review.” But thinking about it’s like, okay, who are the 10 most important people in your life? Did you spend as much time as you would like to spend with them last year? If the answer’s no, invest in those 10 before you invest in anyone else, right? And track the results. Then you look back, and look at the number of peak positive experiences, energetically, emotionally, whatever it is, over that quarter, that year. It’s not something you have to do all the time. And you’re like, “Oh, yeah, doubling down on those 10 really made my year so much better. Blocking out time with those people in advance made it so much better. Okay, let’s do more of that.” So yeah, that’s about it. Yeah. It might have been Tara Brach who talked about the angers, fear on the outside. Who knows? Some smart person who’s a lot chiller than I am said that.
All right, David, here we go. “As a soon-to-be father, I’m thinking a lot about parenthood. If you started a family, what would be the top three values or lessons you’d hope to instill in your children?”
I have thought about this a lot and I’ve been able to watch what has worked and what has not worked. I think optimism, resourcefulness, and lots of physical activity. Lots of physical activity. You got to run that dog. A tired dog is a happy dog. So yeah, optimism. I think Mike Maples Jr. was the first person who really underscored this. He has a bunch of kids who have turned out well. Optimism’s kind of number one. It’s like the mother quality that enables all else.
Resourcefulness, I would say, I think Maya Angelou actually said courage is sort of the mother quality because everything else at its breaking point depends on it. So I had something which is like no failure only feedback. Just encouraging them to try stuff. Positive reinforcement. Try stuff, try stuff. I mean, this applies to dog training too, but some of my friends who have never had dogs get all pissed off and get their knickers in a twist when I compare kids to dogs. I know they’re not the same, but you know what? Shaping behavior is pretty similar across mammals. Anyway, optimism, courage/try a bunch of shit, it’s fine. It’s just feedback. And then resourcefulness. And I think if you have optimism and you’re willing to try a bunch of stuff, AKA, use courage in certain ways, then I think resourcefulness is a byproduct of that. So those would be the things I would focus on, and lots and lots and lots and lots of physical activity, together as a family, right?
Okay. Let’s see. Rachel, “Thought I’d throw out an odd question this time. Have you ever been on a treasure hunt or geocache? What’s the weirdest, coolest, most unexpected thing you’ve found out in the wilderness? Could be something natural or unnatural.”
Well, a black bear stole a leg from my elk last year. That was pretty annoying. And we found it chewed into all sorts of mangled contortions. That was a bummer. I don’t want to have sloppy seconds after a bear has gotten into your elk leg, just pro-tip. I’ve been on treasure hunts and geo cashes.
I would say the thing that comes to mind, which is somewhat unrelated to your question, is that if people are like, “What’s the most interesting way you’ve lost money?” Because I do get my face ripped off then and again, part of the early stage investing game. I invested in treasure hunters, very famous treasure hunters who were searching for sunken Spanish galleons full of gold bars and all sorts of stuff. And ultimately, one of the people involved just absconded with all of the investor money, and it turned into this like, Where in the World Is Carmen Sandiego? fucking debacle, but makes for a story. So once again, don’t bet money you cannot afford to lose, especially when it involves Spanish galleons.
Oh, good lordy, lordy, lordy. Let’s see. This is coming back to encoding. Cindy. “You and Jim Collins talked about encoding.” This is a term that Jim uses, which is somewhat comparable to strengths, like what are your innate strengths, right? So we spoke about that. “I’d love if you’d go deeper on the topic, share more about how it resonated with you personally and give additional practical advice on how people currently locked into work or career situations can progress with a plan towards living fully within their encoded selves.”
I find that asking your best friends, could be family members, could also be employees. 360 reviews can be very brutal. You can listen to my conversation with Joe Gebbia, co-founder of Airbnb about how brutal that can be. It doesn’t have to be brutal, though. I would say that a couple of questions come up that I have asked close friends, some of my best friends, people who know me really well. When have you seen me at my best, or when do you see me at my best? But it’s good to have practical examples or concrete examples from the past, not just like, “When you tend to do this, you tend to do that.” It’s like, “No, give me an example. When have you seen me at my best? When have you seen me at my worst? What stories or memories come to mind?” Then, “What is easier for me than for other people? What do you see in me that I find easier than most people?”
Jim didn’t like that question, because he wanted it all to be internally, individually referenced, but this is how I do it. I actually do find that aspect helpful, because then you’re not only finding strengths, you’re finding strengths that allow you to potentially compete. And I just like having both, if I can. And then you could ask you to what — this is very closely related to the last one, but, “What strength or ability do I discount in myself?”
There’s certain things. A friend of mine was making a point about something related to startups recently. And I was like, “Yeah, I mean, it doesn’t strike me as particularly special because A, B, and C.” And he’s like, “That’s the problem.” He’s like, “You can’t see it because you’re the fish swimming in the water.” And I was like, “Huh, okay.” And then I bounced it off a few other people, and they’re like, “Yeah, that’s like a fucking weird superpower of yours, and I don’t understand it.” And I was like, “Oh, never really realized.” So, “What strengths or ability do I discount on myself?” This is you using that question for somebody else, or not harness, right? It could be discounting, could just be like, “What strength or ability am I not using that I have?”
And one question that can infer a lot of the answers to these others also is if I weren’t doing X, whatever your current gig is, like, “What could you see me doing?” Right? And I feel like if you ask enough people who know you well enough and who aren’t going to bullshit you, who will also be willing to answer questions about your weaknesses, right? In other words, example given, “When have you seen me at my worst?” If they can’t answer that, they’re not going to give you fully candid advice. So I would say those are a few of the approaches that I’ve used, and I’ve found them very helpful.
Geocaching. A lot of people here into geocaching. Yeah, I mean, sure, it’d be fun. I’ve also dreamed about doing orienteering courses, which I think could be super, super fascinating.
This is the last question. I think it’s a good one to end on. “Is courage external or internal? How do you teach it to kids?”
I think courage is learned. You have to practice it. And if you’re not afraid, it’s not courage, right? If someone’s fearless, they’re, by definition, not using courage. You have to be afraid of something. So you can edge yourself, and you can edge kids into that, right? It’s not like, “Hey, you’ve never been in the water before. Let’s take you up to do cliff diving.” It’s like, no, no. Yeah. I mean, that’s unhelpful fear with severe consequences. It’s like you can stare-step into it.
But I don’t think courage is a decision. I don’t think courage is something you get from reading a book. I don’t think courage is something that you can develop abstractly. I think you have to prove to yourself that you have it, and the only way your subconscious will believe it is if you are actually doing things that are uncomfortable. That’s it, which means it is learnable.
And there may be some set point that contributes to it in one way or another, right? If you’re Alex Honnold, and your amygdala is basically asleep, it’s like, “Okay, well, right, that explains a few things.” But it’s also something that you can very sequentially sort of expose yourself to, just like you would to build a tan or to get stronger in the gym. I think it’s through action, right? It’s like progressive resistance that you develop courage, and it’s very — I’ve seen my friends do this with their kids and this is also why the physical activity is very, very helpful to prove to kids, or help them prove to themselves that they can do hard things, right? Like, okay, sure. You could wait until they can sit down with calculus and try to figure that out. Or you could be like, “Yeah, that thing that you’re nervous about doing,” like hitting a baseball, climbing a whatever, 5’9″ in an indoor climbing gym. “Yeah, okay. Well, let’s get after it.”
All right. I will stop there guys. I appreciate, somebody asked, “When is Alex Honnold coming on the podcast?” I had him on about six months before he free soloed El Cap. So if you want to listen to Alex Honnold before he got media-polished, my podcast is a good way to start. Great guy, but it was before he got polished for prime time. And that’s about it. All right, ladies and gentlemen, appreciate you taking the time, and thanks for all the great questions. And be safe out there. Be just a bit kinder than is necessary. To others, yes, but to yourself also. Go first. Smile. Say, “Hi.” Thanks, everybody.
DUE TO SOME HEADACHES IN THE PAST, PLEASE NOTE LEGAL CONDITIONS:
Tim Ferriss owns the copyright in and to all content in and transcripts of The Tim Ferriss Show podcast, with all rights reserved, as well as his right of publicity.
WHAT YOU’RE WELCOME TO DO: You are welcome to share the below transcript (up to 500 words but not more) in media articles (e.g., The New York Times, LA Times, The Guardian), on your personal website, in a non-commercial article or blog post (e.g., Medium), and/or on a personal social media account for non-commercial purposes, provided that you include attribution to “The Tim Ferriss Show” and link back to the tim.blog/podcast URL. For the sake of clarity, media outlets with advertising models are permitted to use excerpts from the transcript per the above.
WHAT IS NOT ALLOWED: No one is authorized to copy any portion of the podcast content or use Tim Ferriss’ name, image or likeness for any commercial purpose or use, including without limitation inclusion in any books, e-books, book summaries or synopses, or on a commercial website or social media site (e.g., Facebook, Twitter, Instagram, etc.) that offers or promotes your or another’s products or services. For the sake of clarity, media outlets are permitted to use photos of Tim Ferriss from the media room on tim.blog or (obviously) license photos of Tim Ferriss from Getty Images, etc.
Comment Rules: Remember what Fonzie was like? Cool. That's how we're gonna be — cool. Critical is fine, but if you're rude, we'll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration.)