An eye opening conversation with podcast legend Tim Ferriss

28:12It is. And perhaps stronger with the absence of video. Yeah, I think potentially stronger if it's just audio. Because my imagination is filling in the gaps for who I think you are, what room you may be in, the relationship you're having with the guest. I'm actually working more, which might make me more engaged. If you don't have the video, you can imagine yourself as another person seated at the dinner or the table. It's a little easier to use your imagination for that. and I'm very fortunate. The vast majority of, of listeners I ever bump into are super cool. I'm very fortunate. I feel very fortunate.

28:44And they'll say, I'm sure this is really strange because I know so much about you and you know, nothing about me and you must have people come up to you and they think they know you. And if I'm being honest, I mean, sometimes I'll just say this. I'm like, if you listen to me three hours a week, you probably know more about what's going on in my life than most of my close friends. Right. You actually do on some level know me, which creates an interesting dynamic. And usually it's fine. Sometimes it gets pathological and super weird. And I don't suspect that any of these warnings will stop anyone from seeking fame.

29:19But I do think it's worth trying to inspect the desire to become famous and ask yourself, if then, you know, if I'm then famous, then what? Right. So like, what is the consequence or what are the consequences or the benefits of fame that you are looking for? And look at alternatives to that. I think fortunately for me, in some respects, as I sort of segue into different chapters in my life, I think the half-life of fame is just going to get shorter and shorter and shorter. Interesting. So the ability to create the durability of a George Clooney, as we remember George Clooney, or say an Oprah Winfrey, as we think of Oprah, I hesitate to say it's impossible, but it's going to be very hard to build that type of dominance and sustain that type of dominance.

30:15There will be some exceptions, maybe the Kardashians, but by and large, I think the half-life of fame is going to be very short. So as there is an ever exploding just font of videos, audio, AI is going to multiply this dramatically. It will be very, very increasingly hard, I think, to vie for sustained attention from a dedicated audience. I wonder if that changes in the independent versus like traditional path. Meaning if you're an athlete and you're at the top of your game and you're in live sports content regularly and ESPN is covering you and other outlets are covering you, if that's more of a sustained version than if you're independently creating.

31:11You know, or if you're, you know, I agree with you that what you're saying, I fully agree. I look out at who was very popular on YouTube five years ago versus today and which creators have, you know, stood the test of time. And it's a small group. It's been very hard to do this sustainably. I think both from audience interest trends, but also from sustainability of creation. When you're independently creating, you don't have an infrastructure around you. We actually, we have a term for it where we call it the paradox of permission, where if you aren't in this traditional environment where someone gives you a permission to stop, like if someone orders a TV show or a show from you, they say you can do eight episodes and then you stop and then we'll reevaluate.

31:54Um, what's beautiful about independent publishing is it's a permissionless environment. You can just do it yourself, but there's also no one there to give you the permission to be like, you can go on break now. Yeah. You know, you, you have the permission to pivot if you want, you have the, you know, permission to, to evaluate this for a second. Like you're just kind of going and not knowing when to stop, which I think is what shortens the half-life. So I wonder if those other environments where the craft isn't creating, the craft is doing something else like playing sports or acting, um, or being a musician if it's longer because of the other coverage.

32:29Yeah. So a few things that come to mind from that. One is actually something that Whitney Cummings is comedian here in LA said ages ago when I interviewed her in his Venice. So I, this is all, uh, geographically triggered for me, but she said something along the lines of, and I'm not going to get it totally right. But then Whitney, I apologize if I'm misattributing this to you, but if art imitates life, you have to have a life. So when you can, in a permissionless environment,

33:06really embrace the freedom of being able to work whenever you want, wherever you want, for most people, what that is going to turn into is working all the time, wherever you are. and you don't have someone to stop you other than yourself. Much more problematic than people might expect. There are ways you can contend with that and plan for it or around it, but that's a real risk for sure. And I would say that my guess would be, and I think this is already happening, is that let's just say we started with BBC 1, 2, 3, and we started with ABC, NBC, CBS. and in that environment you had these kings and queens of media right so you have the oprahs you've got the the howard sterns and that then became in a sense highly i don't want to say decentralized but distributed so all of a sudden you have user-generated content anyone who wants to create a podcast can use an rss feed anyone who wants to upload videos to youtube can upload videos.

34:09And for a while, I think the average or even avid consumer of this content could kind of sort, pick and choose, use discovery to find a handful of people they relied on as their sources of information or entertainment. I think the volume is so high now that it's inevitable that curators are going to become very important once again. And I don't think that'll take the form of someone of the reach of Oprah. I think that's getting like half the country to tune in to a live interview is going to be close to impossible, but you will have, whether it's via Substack or YouTube or otherwise, you will have like a thousand niche Oprah's and they will be the curators for a category.

35:02I think that's inevitable because otherwise people just run out of cognitive bandwidth. And the paradox of choice exhaustion is so overwhelming that they can't function. So I do think that that's part of the reason why I test everything myself. And this seems like maybe a strange bit to tie into this, but it's so easy to destroy your credibility if you recommend anything or anyone. And for me, that is, I don't want to say the scarcest resource, but I want to have impeccable credibility and reliability with my audience, especially anyone I might consider in my 1 ,000 true fans to cite a Kevin Kelly-ism.

35:49If people haven't read 1 ,000 true fans, they should. It's a short article by Kevin Kelly on kk.org. You can find it. I do think about that because that is a sustainable competitive advantage for me. Yeah. As I watch where the puck, where the puck is going. And I think that's too niche curated sort of mini Oprah's in different categories. And I'm not attached to being that, but I don't want to remove that optionality if there are easy ways to prevent it. like test all your fucking products and services before you promote them. It's pretty straightforward. It takes a lot of time, but it's pretty straightforward.

36:31I think that's, that's challenging though. Cause it takes time. And you know, again, as a young YouTube creator, I remember the first brand deal we were offered. It was$800. And at the time no one had paid us to do anything. And so it was like, uh, yeah, for sure. Yeah. You know, like it depends on your, on your circumstances. Yeah. And it was, um, Skillshare, right? Yeah. Skillshare at$800. Um, I hadn't taken a course on Skillshare, but it seems great. Yeah. You know? Yeah. And they'll give me 800 bucks to do it, and I get to keep making YouTube videos. And, you know, that was like a moment where we saw the light.

37:03Yeah. And we proved a model, I think, that this was worthy of being advertised on. Yeah. And it showed other people, this is something that you can do. It gave us the ability to even see what it felt like to be in the advertising business. Sure. I think what you just said is an incredibly important thing to say, which is your credibility is a scarce resource. And it's not easily renewable. It's not renewable. And the foundation of this entire business that we're all in is credibility and trust. Like your audience is trusting you. They're trusting that you're going to show up when you say you're going to show up.

37:37I'm going to make a weekly show. They're trusting that the content is relevant to them when you upload something. They're trusting that an advertiser that you work with is valuable and relevant to them as well and credible. So I'm curious if you can break down some of the anatomy of a good advertising relationship and a good ad as well. Sure. That's a great question. This is why I'm here. The anatomy of a good ad partner. So first I would say that we handle almost all ad sales internally. So I never outsourced all of my advertising or sponsorship to an agency. I think that's a viable option. But in my case, a lot of creators should just focus on getting really good at producing whatever the content is.

38:30Yeah. And not become the CEO of a business or a side business that is advertising. I just happen to be very, very comfortable with that. And I know how it works. And I felt like I could train someone to be very good at it. So I was like, we're going to handle it internally because ultimately whatever the, whatever the slice might be, 15 to 30 % gets very expensive as you start to grow. If you're successful. And I was like, I think we can do that internally. We do work with agencies one degree out, maybe two or three who have been very effective and easy to deal with. For me, easy to deal with is very, very high up.

39:05So first would be, and I do this a lot. It's product or service first. before I even consider the relationships or anything like that. If it's, if it seems to be a prospect and I've trained my team at this point, they know very quickly whether something has a snowball's handsome chance in hell of, of being appealing to me. So I, we, I only end up seeing maybe 10 to 20 % of, of what comes in anyway. And then at that point I will either use it myself or if it's something that I can't use myself because it's a some software as a service for mid to large fintech companies. That's going to be impossible for me to personally test.

39:53But I will back channel. I will talk to their investors, which they generally don't know. I mean, I just know a lot of people in tech. So I will back channel. I will also sometimes, let's just say they're in New York. Hypothetically, I'll wait until after business hours on like a Friday and then put up a post on social, which is if you have used and I will not use the X, I don't want to tag them and then have them maybe flood the comments with seeded responses. I will say attention to anyone who's used X from one to 10, no seven allowed. How strongly would you recommend it to a friend? Pros and cons, question mark.

40:32And then I'll look at it. And if it's, if it's, it has to be eight or higher or it doesn't make the cut. So just as an example, and I've, I've turned away millions and millions, probably tens of millions of dollars. Wow. If things don't pass in terms of product and service, it's very simple. This is also how I've approached most of my investing, which is not investment advice. Please God, don't try to imitate what I did in early stage. It's a dangerous game. but would i could i be a power user and super fan of this product or service yes or no it's super binary yes or no would i recommend this to my friends who will give me endless shit if they don't love it right like my cynical salty yeah stubborn friends who would try it once but if they hate it they're never going to let me forget it would i send this to them if the answer is no, do not pass go.

41:28And those early steps, which might seem less technical are the bedrock of starting this entire evaluation process. After that, we will get to say the question of relationship, even before we get to ad read. Are these people easy to deal with? Are they being really problematic? Are they pushing back on our, our insertion order document, right? Are they chewing up a ton of time from my team, which is a very lean team in a way that is kind of a pain in the ass. And if so, they get cut immediately. Even if they've passed the other hurdles, they get cut. I have no time for it. Just in, in life in general.

42:13Now I'm like, I don't have an extremely high burn lifestyle. That's by design. I mean, I like certain nice things, but I'm not crazy about it.

42:25and that gives me the flexibility if you're the average of your relationships and your parasocial relationships and this is something i'm going to have to talk to my team about on a regular basis or that's going to affect them which it will positively or negatively depending on the quality of that relationship and the ease of that relationship if they're a pain in the ass they're gone and i'm very strict about that so if they're reasonable like it doesn't mean they can't have questions or even object to something in a sort of constructive diplomatic way. But if, if they're, if they're difficult in any capacity, they're gone.

43:00And at this point also I've been very fortunate. The agencies we work with just know it's like, Tim is really expensive and he's very strict and you just got to know that going in. I'm like, great. Like primed. They know what they're signing up for. Perfect spot to be in. And if you think it's going to be like a month long negotiation thing where you change all of his terms, like never going to happen. Not in a million years. And let's say though, that they're like, okay, we understand what we're going for here, which is like, we kind of want to reach the audience of Ted and like movers and shakers in 20 different industries that simultaneously, including journalists at all the top like outlets.

43:37If you want to hit, like if you want to hit that crowd and you're not trying to hit mainstream mainstream, you just have to pay up. That's just the way it works, at least with my show. And so then we get to read and I will not agree to taking someone on. And I don't want to make myself sound like a total jerk. I'm not a jerk about it. It's just like what I can do, the best favor I can do to any sponsor is to have as many check boxes on my checklist to ensure that they will be successful long-term before I say yes. Yeah. Also selfishly just saves us a lot of work. Uh, but saying yes too quickly can create an incredible amount of busy work and repair that I just do not ensure that we just do not want to deal with.

44:28Okay. So I get the read. If the read has a bunch of, especially any claims that I think are dubious related to anything scientific, certainly any kind of pseudo medical claims, or if they're like such and such has been rated number one out of blah, blah, blah. My team already knows this. So I'll get it. I'll be like source. I want to see citations. Number one, how who decided number one, what's the assessment was the analytics firm. Did you pay for the analytics to do this? There are many ways to become number one. I'm super rigorous with that stuff. Oh, interesting. And so we get the read and then my team will do a first pass because they know what's, what's going to get, get me all riled up.

45:14And sometimes it's great. Sometimes it's great off, off the bat. Otherwise, you know, we'll, we'll do some modifications and then be like, all right, Tim is going to freestyle a lot of this. Ultimately final cut is up to him. He knows what works for his audience. Are you okay with that? Because if they need me to read something verbatim, it just ain't going to happen. That's not, not how I work. It's also not in their best interest. So it won't sound like me. And then we have, you know, the, the IO, like, I think we're doing mandatory three spots maybe. Cause I mean, I imagine videos are, you have some idea of after you see things finished in post, you have an idea of how you think something might do, but it's, there's so much outside of your control and there's so many variables and it depends on like news cycle, who knows what's happening that week.

45:59I need somebody who can look at a pattern across three, not a single shot, because it's just, it could be misleading either in overperformance or an underperformance. I'm like, I want you to see the performance across three. Then, and it's, you know, it's, it's a premium podcast, so it's expensive. So I'm also vetting. I'm looking at, okay, here's, I don't, I've never talked about this. This is why it's fun to, to, to have these kinds of interviews sometimes. Uh, because of my involvement with startups, I will look at the position of the company from a funding perspective. Are they in a save the Titanic position where they're trying to do like a last Hail Mary to try to figure out bridge financing?

46:47In which case, maybe I don't want to take that risk because this could perform super well and it could still get canned because they end up having to lay off half of their people and cut back on all these expenses. I want to know that if I do everything within my power and my team's power to ensure they are successful, that they have the capacity to stick with us for quite a long time. You mentioned four sigmatics. They're a great example, uh, and of a success, a success story on every level. Yeah. And so I might check some of that. Then I will, uh, also, um, I will look at the read and I will look at where the, the, where the read takes people.

47:31Okay. So if someone is claiming they want to track, which a lot of people do, and that's fine. First of all, there's a lot of slippage, right? Not everyone's going to use the URL. If they're using a tracking URL and they're like get$1 off your new mattress. I'm like, not good enough. They're not going to use it. And then you were going to say your conversions are really bad and you might use it to try to negotiate with us, or you might genuinely believe that it performed poorly, but that's just because you did not provide sufficient incentive for people to use this laborious code that you're asking them to use when they're listening to a podcast as a secondary activity.

48:10It's too big an ask. So I was like, very often I'll, I will negotiate, not negotiate. I'll, I'll just have someone on my team go back to the sponsor and be like, if you're going to use the tracking in that way, you need a better, you need a better deal. And that's it. End of story. So, uh, and, uh, that's, that's one piece of the puzzle. Another is looking at the landing page and going through the process of buying something, looking for technical glitches, looking for browser compatibility. I mean, like we do stuff that I really don't think most podcasts do and looking at optimizing all of the points with potential failure points for conversion so that if we send a bunch of traffic, we have a reasonable belief that it will convert well enough to lead to a sustained engagement with the sponsor.

49:01because it's just a waste of everyone's time. I would say in some cases, especially mine to go to all that trouble of everything I just described and then to send a ton of traffic to a shitty website and then people can't access the right button on mobile. And that has happened, right? And it very rarely happens now because we do a lot of testing. I could keep going. I mean, this is - Yeah, you know what's interesting is we have been talking about the question of how do you vet a brand partner? Because a lot of creators, YouTube creators are running into, you know, working with the brand for a while and then the brand gets into controversy or shuts down.

49:36You know, FTX was a huge one in the creator space. FTX was a big sponsor in the creator space. BetterHelp, which is kind of oscillated and in and out of controversy at times. And I actually believe the current YouTube brand integration is based on the podcast integration. I think it was the closest comp for a lot of brands, which was, You're doing your, your thing, whatever the content is that's attracting the audience. And then here's a 60 second window where you're going to give my brand messaging to your audience in your voice. That's, that's come straight from radio or podcasting. A lot of brands don't even give you visual assets or any visual guidance.

50:16Yeah. Really. And creators have been asking us, like, how do you, we've been saying you should vet your brand partners. And for us, that means going to meet the founders of the company or spending a lot of time. you know we i represented our ad sales all the way up until last year when we signed with an agency um but that even in in that scenario i'm on the calls still i'm not not on the calls it's just become a little bit easier and nicer to have a buffer yeah uh but yeah we vet by personality but everything you just said it was kind of the checklist of like if you want to go all in on vetting which i think again back to the one of the most important things you said is credibility is a scarce resource.

50:55You're protecting that and ensuring success because that is the product you're selling as a business, right? Yeah. It also means that I can have, I mean, I have three, I guess, three full-time employees and two of them have nothing to do with anything content related. The only way you're able to do something like that, and I'm not saying that is the right move, by the way, I think it's probably too small in some respects, but I am obsessed with like elegant process. I get so turned on. It's activating for me. It's fun for me to be like, all right, there are a lot of assumptions embedded in the, in the advice that I'm getting that will result in having this huge expansive team.

51:41Are those, are those accurate assumptions? Like, let me push back and stress test some of those. Okay. What seemed to be creating a lot of this overhead. Let's just remove those and see if people will say yes. Looks like they might. Okay. Fantastic. And the only way that I can do that is by, among many other things, having that type of vetting process. You know, what's interesting is when we, our company lacrosse network got acquired and when we got acquired, we, you know, I was still my job to go out and sell sponsorships. And we used to do five,$10 ,000 sponsorships on the channel. And we had a head of sales at the company that acquired us.

52:22And I sat with her and she was like, we're going to change the model. If someone, if anyone emails us, you're going to reply and say, our minimum spend is a hundred thousand. Do you still want to get on the phone? And we're going to filter. And it was incredible because what she taught me was it's the same amount of work to make a$5 ,000 deal and a hundred thousand dollar deal and a million dollar deal. So you need to identify where the highest, like where is, where are those deals and actually don't spend any time. I would argue that in many cases, the lower the budget, the more talking you're going to have to do.

52:55Yeah. The more challenging it is. Yeah. Because you also potentially, what you don't want to be is someone's biggest marketing spend, you know, or like, yeah. I'm really glad you brought this up. So when I have sponsors who check all the boxes I mentioned, but this is, I'm getting the impression this is kind of a bet the farm type of move. I'm like, don't do it. I'm not going to take your money. Like keep experimenting, grow, do A, B, and C. I really like you. Let's talk then. And sometimes I'll ask, I don't do this super often because some of the other check boxes now help with pre-vetting that looking at say funding.

53:33There are websites online where you can figure out roughly how much money people have raised in places like tech crunch and, and crunch base and so on report these things. But I've turned away a whole bunch of sponsors, including folks who took it to heart, went out, did really, really well, then came back and spent like 10 times more than they were initially planning. Interesting. But had I said yes in the early stages, there's a very good chance they would have ended up roadkill, right? because they wouldn't have had the ability to spread out over multiple episodes. And man, if they had one out of three, let's say the first one, just face planted for whatever reason, you know, like that day Trump did whatever crazy thing and then forget about it.

54:17News cycle. Goodbye. That would have been a potentially fatal financial mistake. It's a weird amount of pressure on the relationship when, when you're their biggest marketing spent. Yeah. And you said something interesting. You said any level of discomfort will compound over time. Yeah. And I think that really applies to the relationship with your partners and advertisers. Yeah, you can think about it like dating. It's like if the honeymoon phase is like uncomfortable, people are being really weirdly demanding, getting upset at small things, this is not going to get better. Yeah, yeah, yeah. At all.

54:51This is before they give me money. Oh, man, this is going to get so much worse. I think that goes for alignment with the product, too. Yeah. You don't really enjoy the product or the people there. It's hard to not be yourself, especially over a long period of time. I'll just to show you how high maintenance I am. There are cases where I will be in talks with a brand. I think I have a little bit of leeway to give this type of feedback simply because of my track record with the early stage tech investing, my involvement with a lot of these companies. But I'm not going to name names, but there are companies that come to me.

55:26They have a really good product, but it has one or two features that are really problematic. and I will in some cases go back and be like, I think this is a great product and they're launching in like two months, right? They don't have a lot of way over. I'm like, but I can't recommend it because this feature and this feature are a real problem. And it's like, if you change those features or like if you can address this and this, then I'm happy to promote it in the ad read. Otherwise, if you have another product, we can consider that, but I can't recommend this one. Wow. Because I know that, well, I don't know.

56:01I do actually, because my audience is large enough. And if you have, you have an audience that's like several times larger than New York city, it's like you, if you experience something is very, very frustrating, you are not going to be the only one, but is it going to be 1 % of my audience? Is it going to be 50? Is it going to be 70? I don't know. And I'm not willing to take the risk. Yeah. Um, so in some cases I'll actually ask for product or service feature development. You don't want to be the face of customer support. Yeah. No. And people will let you know. Yeah, exactly. That happens with us.

56:36That's happened with us. Because I think what's important is you look at the context of a brand integration as a recommendation. I think that's actually a good term because I remember your book, The 4-Hour Workweek, was the first time I'd ever heard the term firing clients. I worked my life as a, as a, you know, kid of immigrants. I lived in this like world of scarcity that if someone was willing to, to pay me for anything, I was willing to trade anything for that. Right. And like coming up as an entrepreneur, we were incredibly niche. We started a business on YouTube in 2011 about lacrosse. Like that's the most niche possible thing you can do.

57:16Uh, And revenue is very scarce. So if someone paid us, it was like, you know, we'll do anything. We'll make sure it's all good and we'll over deliver and we'll. And when I heard that term firing clients, it was the first time I was like, am I in control of this arrangement? And can I be in control of this arrangement? And is it okay for me to set guardrails and be like, I don't like certain styles of working with you, even if there's a lot of money on the table. And I think it's an interesting thing to discuss as young creators start to get traction. There's more opportunity than ever right now to monetize immediately.

57:55How do you set up yourself to be able to hold off on monetization and to be able to say no?

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58:34There are many different approaches to this and many different philosophical, let's just say, foundational beliefs that can set you on different courses. And I'll explain what I mean by that. So the first is there's one school of thought, which is burn the ships, right? Like if you want to create a path for yourself, don't give yourself option B. Burn the ships and put 110 % into it. there is then a school on the opposite end of the spectrum, which is where I would fall, which is have some financial support in place, ideally so that you are not operating from a place of scarcity or desperation such that you can set constraints for yourself.

59:24So let's just say that one of those is I don't want to do all this like middle manager busy work. I want to really focus on interviewing people and like put my life force into a, B and C. If you don't stick to your guns with that, you will get dragged into just like a morass of all sorts of bullshit. And for that reason, it's, it's extremely helpful to have some source of income in your back pocket if you can pull it off. So I would even say for most folks, look, if it is easy to experiment on say YouTube or in a podcast, it's low cost. You can try it out for a while and continue to do whatever you have been doing.

1:00:09There are counter examples of people who have like risked it all and gone for it and succeeded, but there's a survivorship bias. You don't get to hear from the 99 out of a hundred who blew themselves up in some fashion. So money aside, my assumption is that most people who embark on a creative project don't necessarily have lifestyle boundaries in place for a creative project. That's right. What, and I know this is a much longer story that probably takes you back further, but what turned you into that person who was able to have lifestyle boundaries around a creative project? Oh, complete, complete implosion on every level.

1:00:46Yeah. Yeah. Yeah. I didn't, I didn't like sit down and have a glass of wine and like figure out all these existential questions and go, you know what? Cause I start creative projects. I'm going to fix this. No, I just completely like blew apart. I was going to say, cause I was like, I start creative projects, then implode at some point in time. Yeah. I never go in being like, well, to maintain my lifestyle, I'm going to need X, Y, and Z. Yeah. No, I had a hard correction. Yeah. So, so this was, this was a long time ago, but I guess it was 2004. I want to say I was dating this woman. I thought it was going to be, you know, future wife, mother of my children.

1:01:22And then one day she was just like, I'm done. I'm so done. I can't even begin to tell you how done I am. I was like, what, But, you know, call me as a surprise. It should not have been a surprise. I mean, it was just, I was not present at all for anything because I was working all the time. And that led to sort of personal crisis of meaning. It looked at the business, which at the time was sports nutrition. And I thought to myself, all right, if I don't have time, right, this non-renewable resource, it doesn't matter how much money you have. You can't trade that money for anything. Okay, if I telescope out five years, this just gets worse if I continue doing this the way that I'm doing it.

1:01:55and that led to all the experiments that led ultimately to teaching these classes at you know the school i graduated from and then the all the notes from those classes turned into the four-hour work week that was i suppose the cocktail of factors that led to a correction it was not a moment of enlightenment it was more severe punishment leading to i need to change something Yeah. Okay. Interesting. I'm curious if you've had the, the level of depth you go in with your partners, have there ever been deals that are, uh, cash and equity? Like, do you take equity in any of those deals? Do you invest?

1:02:38Not as part of the podcast. Not as part of the podcast. No. Okay. Uh, I've thought about it though. Yeah. I've thought about it. And especially because my life works without the income from the podcast. I mean, the podcast does feed a lot of everything else, which is spectacular. But I have thought actually recently about potential equity, but that brings a whole slew of separate headache that I'm happy to talk about because I've spent a lot of time in the equity world. But I will say historically, no, there's no equity component. It's just straight cash, prepaid. That is something that creators are starting to do.

1:03:16So I'm curious, what are the headaches? Because it is something we are hearing. I hear a lot of creators that go, I'm starting to take equity now. We also, I can, I can talk about that. I've done a lot of equity. Yeah. Just curious your experience with that. All right. So on the equity side, I mean, I've, I've done advising and investing and have probably invested in a hundred plus companies at this point. I mean, over a long period of time. So I started in 2000. And those include Uber. Yeah. Shopify. Yeah. First, one of the first three advisors to Uber in like 2008, Shopify first advisor. And they had like 12 employees.

1:03:51Duolingo first round of investment. It's a long list. Yeah. Yeah. And most of them die, by the way, which is one of the risks we'll talk about. Most startups fail. And in the case of startups, each of the bets that you make needs to have the, the, the capacity of returning all the money you lost and much more over a string of bad luck. String of bad luck could include global recession, could include any number of factors, right? So investing, you put money in, you get some percentage of the company. Generally, it's going to be pretty small depending on the size of the company. And then you go from there and it's kind of zero to zero or one binary generally goes to zero or you make some money.

1:04:38and then you wait. So there's another risk of equity in most cases. And I think if you're in a Mr. Beast or something, you can make requests of companies that fit a different profile. Right. But by and large, if you invest in a company that is growing or going to grow really, really well, but it's early stage, it's seven to 10 years to an exit. Wow. That's a long time. Long wait. It's a long wait. So advising is where you put in sweat equity and there are certain expectations that you want to make sure everyone is on the same page about, like what the deliverables might be as an advisor. What is the work you are going to do?

1:05:18What help are you going to provide or services or exposure? Make that really concrete. And then over time, they will give you equity. The downside there versus investing is you got to work for it. you got to put in time. And I will say that in an advising situation, cause I don't know how these deals are structured. I actually, I would love to know what YouTubers are doing exactly. Like if they're putting in money or if it's like, I will do these things, therefore give me equity. Cause the risk of the ladder as appealing as it seems, because it's like, I don't have to put in any money, but by the way, time energy equals money in a lot of ways.

1:05:57So you are kind of doing the same thing. if you do something along the lines of advising and the company does not work out you can end up being like the hired help for like 10 years right and have no financial return right and how many of those can you afford to have so i don't do i haven't done any advising in a very very long time because i view the downside risk for me now at this point in my life is higher than investing Investing, you know your downside. Right. It's capped at whatever you put in. Interesting. Can you talk a bit about pricing strategy? You spoke about, you know, keeping your rates really premium on your ad rates.

1:06:40And I think a lot of creators who listen to our show and a lot of, I think even entrepreneurs, like, you know, there's the mathematical side of all of this, which is like CPMs, right? And YouTube AdSense gives us a CPM that we fall under. When you go out to sell a brand deal, or a brand partnership, and you're talking pricing, I think there's a lot more nuance to that based on audience quality, how relevant it is to the advertiser. How have you thought about pricing strategy and what advice can you give on how creators can price themselves? Yeah, my pricing has largely stayed exactly the same.

1:07:14I think I could probably increase it in a couple of instances. I think we're at$60 CPMs, something like that. And I think we could probably charge two or three times that for some of what we do. Yeah. Uh, so I've been a bit lackadaisical, maybe lazy in, uh, in toying with it too much. But at the time that was considered insane. Now, because I think when you started, Oh yeah. When I started, so when you started, you started at a$60 CPF. Yeah. I just wanted to be basically the most expensive or one of the most expensive. And I looked at, I think at the time, some of the NPR shows were like$12 CPMs, but they were third party read.

1:07:53So not host read. And the reads were very short. They did not tie into the hosts in any meaningful way whatsoever. And I thought, okay, I assume the conversions on those are quite bad. Do I think my conversions could be four times better? Absolutely. I think they could probably be 10 times better. And therefore, and I do this a lot. I will, I aim for ultra premium. And this is something I talked about even way back in the day, I guess in 2005, when I was writing the four hour work week, there's always a market for the best. Always. When you get into trouble, in my experience is in this bloody middle where you end up negotiating your rates to appease advertisers who are bargain hunting or price shopping.

1:08:43Yeah. So my, my, one of my goals from the outset was to buy approaching long form in the way that I've approached it with complex subjects, with difficult to reach guests or just amazing guests no one has ever heard of. Right. So I am a source of new experts for people who want that type of exposure. I would attract an audience that would be so valuable that I could charge effectively whatever I want and still have confidence that for a certain subset of sponsors, that would make a lot of financial sense or potentially make a lot of financial sense. All of this brings up like quality of audience versus, you know, just size, scale and scope.

1:09:35And I think also quality of partnerships, quality of, you know, quality as like a, as a factor in this career, which I think is something that is often overlooked, especially now that, you know, the biggest difference I would say between podcasting and YouTube from a audience perspective is the public view count. Yep. The public view count creates an, a whole new layer of complexity, right? Like audiences value. A whole new layer of FOMO and all sorts of dynamics. I mean, advertisers value you based on that largely, your subscriber count and your view count, your average views per video. Audiences make decisions on if you are a quality creator based on that.

1:10:20The market kind of can look at you at a glance on YouTube and make that snap decision. It's very different in private environments. You know, like a podcast RSS feed or, you know, we have a newsletter. We know how many people are part of the newsletter. We publicly talk about that. We want people to know what's going on beyond the scenes. But a lot of advertisers or a lot of people in the market doesn't know how many people are there. And I think it's such a different – it's such an interesting – It's very different. It's changed a lot in the context of what we value. Quantity becomes at the top of that list from a value perspective because it's important for your perception to the rest of the market, right?

1:10:59Like if we're getting 10 ,000 views an episode versus 100 ,000 versus 500 ,000 versus a million, all those numbers I just said give you a completely different perception of how big, you know, literally how big our show is, but also like how premium it is and how much it matters in the market and all the above. I find that to be something that's a really interesting trade-off of putting your work on YouTube or somewhere else. Yeah, it's a huge difference. It's a huge difference. And I, for one love being in on a playing field where, because that is not openly transparent on a given platform, the advertisers pay less attention to it.

1:11:40right right it's just it's sort of this invisible factor and ultimately what at least i've seen over the last five years certainly is a lot of these brands maybe it's different because i'm just such an anomaly in how i run the podcast and the rules and policies are so strange i don't think they're strange they're just unorthodox they just care if on their return on ad spend right that's yeah most people are like i don't care what numbers you show me ultimately it's like dollars in dollars out. What does it look like? Great. I'm like, that simplifies things tremendously. And I'm also in a very advantageous position because I started when there was much less noise.

1:12:19Totally. Right. So I was able to reach escape velocity at a time where it was easier in a sense, simpler, maybe both and sustaining that escape is easier than achieving it now for sure. I would also just add one thing to the came to mind to the equity question earlier, which is, I think we are going into a climate where a lot of startups are going to die. Yeah. And I don't think the pain has fully been felt yet by a lot of companies that have raised a good amount of capital from venture funds and that likely it's Q1 2024 when things are going to get really ugly. And a lot of these companies that are spending very, very heavily on podcasts, probably on YouTube, are going to run into some real challenges.

1:13:27And we'll probably have to cut back a lot in every conceivable area. And many of them will go into business. So there's quite a lot of risk, I think, in equity deals right now, unless you are the lever. Right. Which is happening, right? You brought up Mr. Beast and what he's doing or Logan Paul with Prime. There are so many. Yeah, there are a bunch. I mean, I was with the Shopify guys recently at South by Southwest at their, I can't remember the term they used. Yeah, at the Creator Mart. Yeah, Creator Mart. We were with Harley the next day. Yeah, right. And just walking around and hearing the backstory on some of these companies.

1:14:06It's incredible how much revenue they're driving, which are, in most cases, products and companies that these creators are founding themselves, as opposed to, I don't think, they are other founders' companies that they're taking small equity positions in. So it's a fascinating game. I would just say there's a good amount of risk in taking equity, especially because if you're taking equity, whether it's advising or investing in later stage companies, the valuation is going to be higher. So the percentage you're going to get is going to be lower. And if they don't die, a lot of these companies are going to have down rounds, which means their valuation is going to go down.

1:14:49And depending on your, this is going to get a little technical, but depending on the preference stack and whoever comes in to rescue them, if they have sort of preferred equity, you might get wiped out. Yeah. And those people kind of last money in first money out could cause all sorts of headaches for you later, which is how, you know, I've ended up advising some companies for like seven to 10 years. Yeah. And then end up with like enough money for Chipotle. yeah i'm like literally getting a check i'm like that's 12 and 57 cents awesome so you just need to be aware of of the risk but i a lot of these uh creators i think especially on youtube have tremendous leverage to run really cool experiments yeah yeah it does beget or beg i suppose i'm not sure which it is i guess it could be either the question of do you want to run a business right absolutely yeah yeah that's a big question do you really want to run a business do you or do you just like the idea of running a business because those are different um i do want to zoom into like collaborations collaborations are a massive thing on youtube it's like you know how you grow it's it's a culture and in the interview context like you know this is a collaboration you know and you mentioned like hard to reach guests is was something that you wanted to focus on with with your show early on early on and i think that you have delivered on Um, I vividly remember when LeBron James was on your show.

1:16:13Yeah. I remember that because I was like, so kind of floored by it. I never heard LeBron James in a long form conversation. Yeah. Um, what's that recipe for, you know, interviewing someone or even getting to the interview? Like, how do you get to that collaboration? How do you get to that interview? I would say number one in, in getting big guests is playing the long game. And I can give examples of that, right? Like Schwarzenegger probably took a year and a half in terms of initial contact with someone in his orbit to being in person. Hugh Jackman took more than two years, Jamie Foxx, probably two year plus.

1:16:57Right. And those are Jamie Foxx and Arnold Schwarzenegger are two of the names that I I think led to that early inflection point with respect to the ability to recruit A-listers because A-listers understandably look for credibility indicators in the form of past guests. There are a few things that I've set very early on as policies that I think have been very helpful. So number one, and this was also a differentiator early on because I was doing remote when remote was more challenging to do. Getting someone to a studio, especially if it's someone who's more reclusive is such a high hurdle. I just decided to remove it entirely.

1:17:40So I would say, as I mentioned earlier, it's like, we can record whenever is easy for you. We can do it remotely. It could be, you know, you could be in a sauna, you could be in a robe. We're not going to do video. That was a selling point. And you have final cut as does all, uh, every guest who comes on the show. So that's still, I think a very important and making it as easy as possible for people to say yes. Oh, I'll even say if we record the whole thing and for whatever reason, you're unhappy with it, just can't, no problem. Yeah. And well, we didn't even talk about guest vetting. I mean, you heard about my sponsor vetting.

1:18:21Yeah. There's a lot of vetting. Yeah. There's a lot of vetting. Uh, so by the time we get to booking at this point, we have very high degree of confidence. They're going to be good guests. Right. And we don't make the guests jump through all that hurdles, but we do a lot of background work. And sometimes it's easy. Sometimes it's hard. If somebody has long form audio or video, it makes it pretty easy. Yeah. And if that's not compelling, I don't care how much of an A-lister they are. It's just not going to happen for me at this point. It's not interesting. And if it's not interesting to me and my assumption, it's not gonna be interesting to a bunch of my audience.

1:18:53and that's abusing my privilege of having an audience. So I don't do it. I will generally ask for the guests' favorite long form interviews they've done. It could be text, it could be video, could be audio. And reviewing those is kind of step number one. And then we will, in terms of prep, which relates to the question of making an interview work, go to, for instance, Wikipedia or look at profiles and look at tiny mentions that were glossed over but not expanded upon. Like little tiny nuggets. It could be anything, right? So-and-so is, I'm making this up, right? Like a Russian-French cop lit major at such-and-such university for two years and then switch to something else.

1:19:43Like, okay, I've never seen anyone ask about that. So I might start with something like that, especially with someone who's been interviewed a lot so that they sit up and they go, oh, this isn't an autopilot interview. You've actually done your homework. I will look at their favorite interviews to identify greatest hits in the sense, like if anyone has been interviewed for a period of time, they have material, right? And so I'm basically looking at like the Netflix comedy special to be like, all right, what did they put in? Like, what would I put in the trailer to try to get people pulled in. All right.

1:20:24I want them to be comfortable. I don't want to flood them with a bunch of novel questions right off the bat. With some guests, I'll do that, but very few. I don't want them to feel knocked on their heels too quickly. So I will let them warm up and also engage the audience with one or two greatest hits stories that I'll generally prompt. I don't always do that, but I do it reasonably frequently to make them more comfortable. I will ask them if they have any points or topics they would like to explore, you know, exploratory bullets. Let's just say sometimes they provide it. Sometimes they don't.

1:21:00And then when we get on, I was going to say the phone, but it's not really the phone. Although I have done that sometimes, but if we get on, let's just say some type of recording platform for remote episode and 90 plus percent of my episodes are remote. I really always try to take if they're not in a huge rush. And if they're in a huge rush, I've already made a, right. An error because that's not a great formula for a good interview. Uh, spend five to 10 minutes just talking, let people limber up myself included before you launch to the first question. So I'll talk to them and I'll always say, look, this isn't live.

1:21:43You have final cut. If you want a bathroom break, a water break, whatever it might be, that's very easy. If you want to restate anything, you can just stop and then restate and we'll fix it in post. If you say something and you're like, oh, shouldn't have made that joke about my wife. Let's cut that. We can cut it. This is as friendly as it gets. And then I will ask I'll ask the guest what would make this time really well spent for you what would make this a home run just like I asked you guys before we started almost no interviewers ask interviewees that question ever it's a good and it's so easy yeah and I've had so many guests I mean I would say at least 20-30 % of the guests especially those who do a lot of interviews are like huh I've actually never had someone ask me that yeah it's good and they're like thank you for asking that.

1:22:34And then they think about it and they come back and I'll, because I'll say that can inform how I architect the conversation. And I have very interesting audience that can inform how I direct the conversation towards particular segments of my audience. What would, what would make this, if you look back at a three months from now, it's come out and you say, wow, if some, if somebody else asks me, what is one of your favorite interviews you've ever done? I want this one to be the first one you send. That's a good note. And I'll say, you know, I always like to let people know where I'm going to start so that we don't stumble out of the gate.

1:23:12I'm likely going to ask you about this, da, da, da, da, da. Like, who is Joe Herbert? And why is he important in your life? Does that make sense? Is that a comfortable place to start? And I'll do that before I have the rest of the housekeeping stuff so that they have time to sit with that. And it has time to germinate so that by the time we get to it, it's like, boom, out of the gate. They're in good shape. And I really feel like the tenor of interviews, often not always, but it's decided in the first 10 minutes. So you really want to do everything that you can possibly do to ensure that the takeoff, like taxiing and takeoff is as smooth as possible.

1:23:52So those are a few things. That's really good advice. Your answer just revealed to me how new this career is for Samir and I. Yeah. That was so much for me of like, we did almost nothing. Yeah. Almost nothing on that list. I consider you and I'd have a lot of attention to detail with most of the things we do. But hearing that was so interesting because clearly you didn't start out the gate like that. No. Yeah. It's just stuff I figured out. There's a lot behind the scenes. This like the setup. It's like the gymnast who goes out in the Olympics and does a routine. Yeah. on the, you know, on the parallel bars, didn't just walk out and do, there's like the warm up and everything going into that's really important.

1:24:33And I view the interviews as a performance sport. That advice will change the way that we operate. Like, I just want to say thank you for that. Cause that, that was really helpful. And I wanted to ask you, um, you know, you've, you've been now you're on the precipice of 10 years, 664 episodes. It's something like that. Something like that at the recording of this, nearing a billion downloads of the show. Have you ever been at odds with the Tim Ferriss persona? Like, you know, like you are, all of my friends, I can say, oh, I'm chatting with Tim Ferriss today and everyone can snap, be like, he experiments.

1:25:16He's into, you know, psychedelics right now. Like there is a being Tim Ferriss and being this public, people have expectations of who you are and what that means to be Tim Ferriss. In the last decade, have you been at odds with that persona? I will answer that. I want to ask you guys a question first. Yeah. This is not a dodge. I've just been, you might've noticed I'm like looking around. How the hell do you guys keep this much in your head? I always have notes. Part of the reason I like to do remote interviews is I have copious notes in front of me. So is this a out of the box ability? Is it a trained skill?

1:25:51Like, do you guys have some routine for actually keeping track of this stuff? You can go first. We are documentary filmmakers by trade. And in doing this, I'm looking at you, but I'm also looking at a timeline and live editing. So I'm like, you said something over there that I want to connect back to. And I can hold that in my head while we continue and then bring this piece over here. So I can do, so I've trained that ability as well just through the podcast. But what I'm wondering is when you come into this, you've prepared and you have, who knows, 12 topics that you might want to touch on. Is that just a natural inborn ability to remember that list of things?

1:26:33I was looking around because I'm like, is there a prompt or something around here? I just wanted to see. What's your answer? Well, there's an element of writing it down, right? So we have research provided to us, interesting buckets. I wrote some of it down so that I could recall it. but there's also this element of if Samir is asking you a question, I have a moment. You have time. I have more time than a solo host to think about where this is going to go next. Right. Or if I want to take it in a completely different direction. Yeah, that's a good point. Some tag team. There's some timing involved.

1:27:02We have a bit of a competitive advantage there. Yeah. It can also be difficult because if I have a direction that I'm ready to go and all of a sudden Samir or you take it in another direction, I have to let that go. Yeah. And we both took improv class, which helped with that separately because of that requirement of yes and both the guest, but also each other. Cause you know, I can be, I can hear you and I'm like, I'm exactly where I want to go next. And then call and ask a question and it's like over there and I have to be fully present. Okay. With maybe my question won't come up in the natural flow of conversation.

1:27:37I have to let that go. And that is a dance that we have to do together, but also with our guest. And the other thing I would say is we're trying our best right now to explore the relationship with preparation and natural curiosity. Yeah, totally. That's a really hard balance that I've noticed. Sometimes when we're overprepared, I'm not even listening to what you're saying. I just know where I'm going and I know where you're going. And there are different styles. There are so many different styles. You do not need to, if people listening or watching, emulate any one person, right? I mean, when I was getting started and I will come back to your question, the, the habit that I have and I always have, which I think is a good one generally is to like research, research, research, research, study, study, study, study.

1:28:19So I was looking at Kerry Gross. I was looking at Howard Stern. I was studying James Lipton of inside the actor studio, actually hired some of his researchers at one point as contractors to read through transcripts of my interviews to point out where I could improve. I've really went after it but if you look at say James Lipton my understanding is he's got his his blue cards and he never deviates from those cards in other words he does not take the side alleys if something comes up and it could be interesting to explore he does not deviate and guess what it worked great yeah now they also did quite a bit of editing so they would record multiple hours and then cut down to whatever it would be 45 minutes or an hour.

1:29:01And then there are others who would come in basically blind, Larry King, blind, like effectively no prep. And he's like, I want to stand in for the audience. Now, maybe that's a very elevated way of saying, I don't want to do research. I don't know, but he was good enough to make it work. I also think then it was easier in a sense, because if you'd made it through the sensors and the, the gatekeepers to a point where you are one of the four interviewers on primetime, you have a lot of license to do things that you cannot do in an environment where you have to vie for attention the way that you guys do or that I do.

1:29:34To answer your question, at odds, have I been at odds with the Tim Ferriss persona? I would say when I feel like maybe I'm getting too comfortable in a lane or fearful that I need to protect whatever identity I have created, which is not frequent but if i think i the way that manifests if i start thinking if the thought occurs to me that i shouldn't do x i really should do more of y but i don't really want to but i can't do whatever this is over here when i start constricting myself in that way i'm like okay this is a bad habit i want to nip this in the bud right now so i'm going to put up some social post that is definitely reflective of my true personality yeah but it's going to offend the shit out of like half my audience.

1:30:21And if they, if they're not willing to accept that, I don't really want to be shaped by them because we do get shaped by our audiences and you have to be very, very, very cognizant of that. It's going to happen no matter what, but you can become, I'll give you an example. Maybe a year ago, it could have been two years ago with my team. We looked at the top 20 performers in terms of total downloads over the first six weeks, something like that for the prior year. And the first three episodes, like the gold, silver, and bronze medalists were all crypto related. All right. So the immediate thought and recommendation from some other people, the consultant types we were working with was double down on crypto, do more crypto.

1:31:11And I thought to myself, let's telescope out. what does this look like if I take that advice? This becomes a crypto show. Do I personally want to talk about this all the time? Answer is no. Everyone's in a blue moon. Yes. And if I double and triple down on this, I think it's, I think it's playing a very short term game and I don't want to play short term. This, this is something I want to play longterm. So by, by, I think pushing back instinctively or, just as a policy against anything that I feel compelled to do, whether it's related to my own identity or direction of the podcast, I prevent getting too attached.

1:31:54And everyone's in a blue moon, right? It's like, okay, it's crypto, crypto, crypto. But then I do a interview. I think it was Dr. Sue Johnson, this late seventies, maybe eighties, uh, relationship slash family therapist in Canada. And this thing exploded, right? Completely bananas. And I was like, thank God. Yeah. that it doesn't all have to be crypto. Yeah. You're following your authenticity. Yeah. I'm following my interest. And, uh, so I'd say that those are, I think about this a lot though, because it's very easy to be shaped by your audience. It's very easy to be shaped by whatever trends or fads are really prevalent.

1:32:32Easy to be shaped by the market. Easy to be shaped by the market. Yeah. And I would just make a couple of suggestions to folks. So part of what has really informed my thinking are there's, a chapter that is in the 22 immutable laws of marketing. It's incredibly outdated in a bunch of ways, but there's one short chapter. It's probably five to 10 pages long called the law of category, which was incredibly impactful for me. And effectively it's just saying, don't be the best, be the only, like, how do you create new categories? The question of how, how can I be a category of one? Yeah. Right. So when people ask me like, how do you feel about your competitors?

1:33:12I'm like, I don't view any of these people as competitors. As soon as you start thinking competitive terms, you're going to start making compromises and succumbing to group think and conforming in ways that you may not even recognize. And that will lead you to be less differentiated, generally speaking. But it's, it's easier for me to sit here and say all this stuff than it is someone who's in hyper growth mode and the first few years of a project. it's like in the beginning you got to buy your first few clients in a sense right when i did my first angel investing i deliberately set out to make myself the cheapest labor on the cap table with all that means is i'm putting in like 10k investment right even if it's a moonshot that pays off like okay so maybe i make 100 grand over 10 years it's not you know sort of net present value of that.

1:34:09It's like, it's just not a huge payoff. And I was like, I'm going to put in a hundred thousand dollars worth of value in terms of my work for this company from advising in like the first two months. And they're going to be like, what the fuck is this guy doing? It doesn't make any sense for him. But what was I after? I wasn't after the payoff of that company. I was after a referral. I wanted a, the strongest possible recommendation from that person to the next CEO or founder. And similarly in the beginning, you, you may, and probably will have to bend over backwards to make sponsors happy, even if it financially ends up making very little sense for you because you're putting in so much time.

1:34:50But what do you need? You need referral and credibility. And once you build that momentum, you are in very good shape. assuming you don't destroy your reputation somehow or damage it. Which is surprisingly easy to do if you start cutting corners. That's really helpful. Is there still space in the podcast world for creators? I think so. You just have to compete. I mean, it's a bloodbath out there. Now, I would say that if you are, it depends on why you're going on. Is there room to go in and do interesting things and find incredibly personally rewarding if you approach it the right way? Yes. is there room for creating something that is financially viable if you have the hope of supporting yourself and maybe even your family with a very comfortable lifestyle but not private jets and like flying to con and whining and dining with leonardo dicaprio yeah absolutely right but if your aspiration is the leo this is this is this is all or nothing yeah i either want to be a super celebrity raking in millions of dollars a year or it's a failure, then you're setting yourself up for a psychological implosion.

1:36:07Right. And it's the odds are against you. Yeah. I would say if you on the flip side, read 1000 true fans from Kevin Kelly, you can find it at kk.org and you pick up a couple of other things and you're like, all right, I just want to feel like I am contributing to a community of like-minded people who I really like doing something that I respect myself for doing. Yeah. Try it and do it in the most, in the, in the lightest way possible, right? Cheap, fast experiments. For me, that's the name of the game. I still, I mean, I, I have the resources to do expensive experiments. I very rarely do expensive experiments.

1:36:49Number one, because I think they're, they're not necessary. Number two, I think that you actually create friction for yourself by making things more expensive or having them become projects when really they shouldn't be a six month commitment. They should be a two week commitment. So I really try to hold on to a lot of these things lightly. And also it's like, if you zoom out, it's like, look, this is not my phrasing, but it's like, we're a bunch of monkeys on a spinning rock, like in the middle of the cosmos. Who fucking cares? you know, like try your new YouTube format. Oh my God, the sky is falling.

1:37:26No, it's no, like Alexander the Great. What's his full name? Greatest conqueror the world has ever known. Like nobody knows. Like, you know, like really like this is not going to be in the grand scheme of things. 10 years from now, something that you worry about. So like try it out and you can always put that jacket back on. I love that. I really, really, really enjoyed your ebook of the 17 questions to ask yourself. And, uh, I just wanted to ask if you could talk through some of those questions and where you came up with those. Yeah. Because I find as I go through my creator journey and my entrepreneurial journey, it's like, um, I'm very good at finding solutions to problems or answers to questions that someone brings to me, but I'm not very good at finding the questions I should be asking myself.

1:38:10And I've, I found that to be a very cool ebook that you created and really good questions that make you ponder of what are you, what are you spending your time on what you're doing yeah totally those 17 questions i think they appear in tools of titans maybe tribe of mentors one of those two books those are questions that i have gathered over a few decades and so i'd say number one is just borrow shamelessly whenever you come across a good question capture it somehow i do that i collect questions so if i'm reading an in-flight magazine and then there's an interview and I'm like, huh, terrible interview, but that question's really good.

1:38:50I will literally, I'm not proud of this, but I guess back in the day I would tear out the page. Now I just take a photograph and sometimes they work. Sometimes they completely flub. They don't work at all. That happens too. Fix it in post. That's my recommendation. But those questions have helped me. So I returned to them frequently. And this is top of mind because a younger friend of mine came to me asking me about these 17 questions. And he said, how do you come up with these questions? And I was like, well, first of all, you should notice that some of them are just stolen. And there's one, for instance, which is, am I hunting field mice or antelope?

1:39:31What does that mean? Yeah. The whole story that goes around it is, if you're a lion, you can stay alive by hunting field mice and spending all of your time hunting field mice. but you're much better suited to going after big game and going through intense sort of sprints of focus that allow you to down real significant prey. And so it's just an easy metaphor to ask yourself, am I majoring in the minor things? Yeah. Right. Am I really focused on the one or two things that could change everything? the one or two things that can make everything else easier or irrelevant, or am I just scattered and doing every tiny task that grabs my attention because I don't have a forcing function.

1:40:23So that's one. Then there are others which are older for me. Like what if I did the opposite for 48 hours with respect to business process? Right. So if I'm checking email 10 times a day, what if I checked it no times a day for 48 hours? What else could I focus on? If I currently, and these aren't exactly opposites, but people will get the idea, to do something dramatically different from what you were currently doing. So if you really curtail, let's just say the ability that your team has or an assistant to make decisions that are above a certain dollar threshold, right? Let's just say you let them make decisions, but anything above a hundred dollars, you want to have your say on or a thousand dollars.

1:41:13Remember I'd be like, what happens if you just completely rewrite that for something significantly higher? I'm not saying you should do this. This is hypothetical. if you make it ten thousand dollars for a week and you're like all right i'm going to keep an eye on it so it doesn't run out of control like what actually happens chances are that whatever downside risk you had thought was a prohibitive risk that has led to this policy that actually is very draining for you personally and it makes you a bottleneck could be removed there's very very frequently once you stress test it by doing the opposite for say 48 hours or a week whatever the timeframe might be, you can remove it.

1:41:51Let's see. There are a whole lot of questions. Those are the ones that come to mind for me right now, I think because they're relevant to decisions that I'm making probably in the next handful of months. Are there any others that stick out to you? No, I really like those. I think, you know, the frameworks that you provide, especially with those, the opposite is a really interesting one because it addresses something else I wanted to talked to you about, which was fear setting. Like the opposite is a lot of our actions, I feel like in a day are, are, uh, you live in, in fear of what if you don't do it.

1:42:26Right. Like, so if we're like, let's say we're, sometimes I try and sit and question everything we're doing. Right. Which is similar to that where it's like, what if we, what if we didn't upload the video of this? What if we, what if we, you know, didn't do this show at all? What if we don't upload YouTube videos? What is it like live in the world of just the complete opposite of what you're spending day to day on? And I think it's also allowed me personally to say, what if I wasn't on sales calls? What is the, what is the risk? How do I evaluate that? Cause I think you can get off sales calls.

1:42:58Yeah. But it took me a long time to do it. Cause I was fearful. Yeah. I was very fearful. For sure. Yeah. Yeah. Yeah. What if I, what if I didn't do that? And then you, you look. I've been off sales calls this whole time. You've been off sales calls the whole time. Look at me. You know, but it addresses that. The questions that I would love for you to speak about fear and fear setting, because it's another one of your frameworks that I really appreciate. And I think that as an entrepreneur and as a creator, fear has been such a presence in my journey. And we talk so much about goal setting. Whenever I'm feeling fear, I will goal set.

1:43:33Let me hit pen and paper and say, okay, what am I working towards? What's my North Star? But I want to address the fears. and your framework was the first time I heard of something that allowed me to say, wait, I can actually just write these down and address them. Yeah. Yeah. Happy to talk about that. And another question that I ask myself frequently, which I think would be great for creators to play with is if you had to take a four week vacation, not two, like you can't let things catch on fire and then put on band-aids after four weeks right maybe you can do that for a handful of days maybe a week you can let the house catch on fire and then try to put it out but if you had to take four weeks no computer no phone you are off the grid what kind of systems would you put in place you had to do it what kind of systems you put in place how would you make it work how could you make it work is a really helpful exercise yeah so on the fear side so fear setting first i guess made its public appearance for me at least in the four-hour work week and i've continued to do it probably once a quarter sometimes more frequently depending on what neuroses you know has gripped me at the at the time and uh it's very straightforward so in the same way that you would goal set and make things specific, measurable, achievable, you know, smart, right?

1:45:06Have time bound, et cetera. You're applying a lot of these same criteria to your fears. And therefore the name is fear setting because the, the, the fears really exert the most paralysis and produce the most anxiety when they are nebulous. when they are unclear, when you're just in a room of psycho-emotional smoke. And there are some easy ways to clear that out. I think it was Yoda who said, name must your fear be before banish it you can? Yeah, I wouldn't know. Something along those lines. Sure, yeah. That's for you, Star Wars nerds. naming your fear allows you to defang it in some interesting ways.

1:45:56And this is directly borrowed from, it's, it's a, it's, it's a, it's a slightly user friendlier version or more concrete version of something called a premeditatio malorum, which is an exercise from stoicism. Seneca the Younger has written extensively about this, but the power of negative visualization. In other words, the benefits of imagining the worst case scenario. And some people might say, and I run into this sometimes, they're like, well, like you're just going to manifest the worst thing if you're constantly focused on that. It's not to constantly focus on it. The only way you can avoid constantly focusing on it, I think, is by kind of trapping it on paper in a way that lets you to let's you see how manageable most of your fears are.

1:46:47And the way you do that is, is straightforward. And I can also recommend if people are more visual, I have a Ted talk that I gave some time ago. Um, it's, it's done quite well. I think if you just search my name and fear setting and video, or if you go to Tim dot blog slash Ted, then you'll find that as well as a script that you can look at. It's very simple. So let's say we'll take the four week off example. So you're imagining taking a vacation, but if you're like most driven entrepreneurs and maybe we should come back to drive at some point, but most driven entrepreneurs, your, your utopian ideals that you have in your head of what entrepreneurship will look like are shattered pretty quickly.

1:47:35and you just end up working all the time. So maybe the idea of taking four weeks off, it seems like a complete impossibility. It's like, okay, well, let's stress test that rather than just saying, I can't do it. I can't do, I can't do it. Like, well, let's test that a little bit. Maybe you're right. You might be right. In some cases you examine your fears and you're like, yeah, that shit's scary. I shouldn't do that. But you should at least cross-examine them first. And the way you do it is very simple. Grab a piece of paper. You can do this digitally, I find it better to do offline because there are so many things that can pull you in terms of notifications and distractions.

1:48:10If you're online, that's also a challenge of YouTube versus podcast. Yeah. Right. Man, are there so many shiny objects trying to grab you in the periphery of that video? Okay. So you have a piece of paper, make, make three columns. columns the first column is listing out all the things that can go wrong so you take four week vacation what are the things that can go wrong and you write them out and make them as specific as possible right so who knows i remember when i first did this is a long time ago but it was like i'm gonna miss a letter from the irs and i'm gonna get in trouble and they're gonna audit me and okay that's one next one is uh some suppliers gonna go out of business this is when i was running the sports nutrition company and manufacturing is going to have an issue and yada, yada, yada.

1:48:59Right. Okay. And down you go in this column and try to come up with at least 10. Okay. That's like the, the, the worst things column. The next column is what you could do to minimize the likelihood of those things happening. Right. So missing the IRS letter, you could redirect those letters somewhere else. There are a number of services that will forward mail or PDF scan them and send them to people like, for instance, your accountant. Yeah. Great. That should solve the problem. Right. And then you go down, all right, supplier issues. Well, maybe if the supplier issues, and this is a real example from, from, uh, from my life, most likely problem scenario was running out of one or two bottleneck ingredients in some of these products.

1:49:47I was like, okay, well, it would be a little expensive, but what if we pre-ordered a stockpile of this so that at least for a period of three months, the likelihood of it running out was effectively zero, assuming no spoilage. Would that solve like 90 % of the supply chain issues? Yes. Okay. So that might fix it. Things you could do to minimize the likelihood of these things happening. third column if this thing happens what could i do to recover from the damage or get back to baseline right so let's say you have one that's really looming large right the whole business fails and like this income that i have that pays for blah blah just disappears okay well if you have a low burn lifestyle which i had at the time uh i can go get a job like serving in a restaurant and if it got really bad, I could ask some friends to like loan me some money.

1:50:49I could go into credit card debt, but it wouldn't be the end of the world as I know it. Sure. Right. It's like, okay, like if this thing happens, what could I do to undo some of the damage or at least get on my feet temporarily? And you just go through the list. You do the same thing, right? Missed letter from the IRS. They get pissed off. What does that actually mean? Probably paying penalties. It's not like they're going to come in a black helicopter and throw me in the back of an unmarked van. No, that's not going to happen. They're just going to be like, okay, idiot. Yeah. We're going to punish you with some fines.

1:51:19Like that's what's going to happen. Okay. Right. So you kind of walk through, if it happens, how could I, how could I undo the damage or get back on my feet? And you just go down the list and in the span of doing this, and you could do this for a relationship, right? Maybe you're considering getting into one. Maybe you're considering getting out of one. You could do this for a career shift. You could do this for launching a new channel. Yeah. Right. You could do that in my case. This is another sort of peak behind the curtain, but just for the purposes of longevity and sustainability, I experiment with podcast formats.

1:51:51I've done all sorts of weird experimental formats. I'll never forget the first time I heard you drunk dialing. Oh yeah. The drunk dialing episodes. I haven't done one of those in a while. Those got a little squirrely. Yeah. I would have people, I would have people fill, fill out a Google form. Wow. Yeah. I haven't done one of those in a while. It just for people that you don't know. And then I would use Skype to just randomly call people. Yeah, I recall. Between this hour and this hour. By the end, it got pretty interesting. It'd be interesting. And then I'd, so drunk dialing would be me like, well, I was supposed to be slowly, but drinking whatever my favorite booze was.

1:52:23Yeah. And those got a little squirrely. Yeah. But if I'm considering doing something like that, it's like, all right, well, what's the worst thing that can happen? Generally not that much. It's so helpful to have it, not just like ruminate in your head, like to just write it out in a framework. It's like, it's incredibly helpful. So yeah. Yeah. If you have anxiety that is being produced by thinking, chances are more thinking is not going to face it. And at least thinking as it ricochets in your head, put it on paper so you can see how fragile a lot of the assumptions are. Yeah, totally. So that's, that's, that's fear setting.

1:53:00And certainly for me, at least as someone who tends to, frankly be very fearful of a lot of things and we could psychoanalyze and unpack shit out of that for ages we won't do that today but it's goals are not the problem right like yeah pressing on the gas in six gear is not the problem it's that i have the emergency brake on a lot of the time so it's like all right how do we drive without having the emergency brake on unless it's absolutely necessary. Okay. And for that reason, I, I typically find fear setting very, very, very, very helpful. Tim, we could keep you here all night. We really could talk to you for a long time.

1:53:44I think it's probably the deep parasocial relationship I have with you from years of listening. I feel like I'm talking to an old friend, but I really appreciate you coming on. I think you imparted a lot of wisdom, not only to our audience, but again, this is a selfish show for us. Like this is an episode that, uh, has been on my bucket list for a long time. And I, you said some things that are, uh, tangibly going to change the way we operate. So I really appreciate that. I woke up this morning and thought to myself, I'm speaking to an Olympic gold medalist interviewer this morning. So I was super excited.

1:54:13Yeah. Well, thanks guys. I mean, you're, you're excellent at what you do. Just a quick question. What would make this interview a home run? I know we're about, you know, an hour and a half in or something, but you know, just, Yeah. I mean, I think, uh, I was, I was thinking that I was thinking that to myself actually coming in. I was like, what would be, I mean, aside from just enjoying the, the dance of seeing how you guys do things and, and hearing novel questions that forced me to think about things differently. I would say there are a few things that I'd love to draw attention to for people who are interested.

1:54:50I started a foundation, I don't know how long ago it was, six to 10 years. Time is a blur for me. A girl called Saisa Foundation, S-A-I-S-E-I foundation.org. People can check it out. So it's a nonprofit foundation that funds mostly early stage science related to basic science, related to psychedelic compounds and then therapeutics. So I would encourage people to get engaged with that space if it's of interest. And you can learn more about that at PsySafeFoundation.org. Just look at the projects page. I think a lot of them are interesting. And if I may recommend people to check out one other thing.

1:55:30So if I had to give up everything except for one way of reaching my audience, the one piece I would keep is actually the email list for a lot of reasons that we will talk about in a round two sometime. But if people want to see what that looks like, I've been doing five bullet Friday, which is this free newsletter. I've been doing it for a long time. God, I don't know how long it's been, but it's like every week for, I subscribed in 2015. Many, many, many years, every week. So it's basically a diary of the coolest things I've come across that week. Like it's the closest to a diary that I will ever come.

1:56:05So I actually go back and read old editions, which is really fun for me. it's a five bullet Friday, super simple. It's like a one pager that I send out every Friday of whatever the coolest things are that I've come across that week. Just go to tim.blog slash Friday and you can try it out. I'll second that recommendation. I'm a subscriber. It's great. Yeah. All right, Tim. Yeah. Thanks so much. Thank you.