Modern Wisdom - #1047 - Jonathan Swanson - The Obvious Strategy to Take Back Your Time

Episode Date: January 17, 2026

Jonathan Swanson is an entrepreneur and co-founder of Thumbtack. What if instead of using extra money to buy things, you used it to buy time? Delegation has never been easier, and with AI, you can 10× your productivity without working more. So what does smart delegation actually look like, and which tools make it possible? Expect to learn why buying hours is more important than buying things, why delegating your tasks is so important and the Cardinal sins of delegation, what Jonathan's top themes of being good at delegation are, what it would take to build your best life using assistants and much more… Sponsors: See discounts for all the products I use and recommend: ⁠https://chriswillx.com/deals⁠ Get the brand new Whoop 5.0 and your first month for free at https://join.whoop.com/modernwisdom Get 15% off your first order of Intake’s magnetic nasal strips at https://intakebreathing.com/modernwisdom Get a Free Sample Pack of LMNT’s most popular flavours with your first purchase at https://drinklmnt.com/modernwisdom Get 15% off any Saily data plan at https://saily.com/modernwisdom Extra Stuff: Get my free reading list of 100 books to read before you die: ⁠https://chriswillx.com/books⁠ Try my productivity energy drink Neutonic: ⁠https://neutonic.com/modernwisdom⁠ Episodes You Might Enjoy: #577 - David Goggins - This Is How To Master Your Life: ⁠https://tinyurl.com/43hv6y59⁠ #712 - Dr Jordan Peterson - How To Destroy Your Negative Beliefs: ⁠https://tinyurl.com/2rtz7avf⁠ #700 - Dr Andrew Huberman - The Secret Tools To Hack Your Brain: ⁠https://tinyurl.com/3ccn5vkp⁠ - Get In Touch: Instagram: ⁠https://www.instagram.com/chriswillx⁠ Twitter: ⁠https://www.twitter.com/chriswillx⁠ YouTube: ⁠https://www.youtube.com/modernwisdompodcast⁠ Email: ⁠https://chriswillx.com/contact⁠ - Learn more about your ad choices. Visit megaphone.fm/adchoices

How did you get started in thinking about time and delegating? So my first job out of school was working at the White House, and I worked for the president's top economic advisor. And I got to walk in the West Wing every morning, which was a cool life experience. And I sat next to the president's executive assistance. And as you might imagine, the executive assistance to the president are really freaking good. and it set my bar crazy high for what this client EA partnership could look like. And so when I left the White House to start my first company, I asked myself the question, what if I had an assistant or a team of assistance that was as good as the presidents?

Obviously, I'm not going to become president, but what else could I accomplish if I had that sort of support? And so I hired my first assistant that way and then set out on a journey to build the best team I could to see how it would change my life. life. What were the unlocks that you saw inside of the White House? Like how complex and big is the system of spindly octopuses with their tentacles and everything trying to help get the machine moving? I mean, it's insane. The president has multiple assistance, as you might imagine, there's actually an entire department called advance that plans every minute of the president's life for months in advance. And so if he's going to be in Brazil in three months, there's people deployed months in advance to go scope, prepare everything. And, you know, I think there's just kind of the level of

optimization, which is one thing. But the thing that really struck me sitting next to the president's assistance is seeing the relationship they had. It wasn't just saving him time or doing tasks for him. At the end of the day, he would sit down, lean back in his chair and be like, what happened and he would talk to his assistant and this was one of the people he trusts most in the world there's all these other people jockeying for his attention governor senators and his chiefs but this assistant is the one person who's just like got his back fundamentally emotionally psychologically and you can tell there was a real psychological connection that was very valuable beyond just the work so it's a deep relationship

of trust and kind of awareness I suppose because of how globally you connected that assistant is to everything? Exactly. Like if you have an assistant there in your inbox, they're seeing the lawsuit that's coming, the person that's quitting, the money you just raised, the investor that rejected you, all the highs and lows that are shielded from most of your company and most of the White House, but that assistant sees all of it. And so they're on the emotional journey with you more than really anyone else. Okay, so jump to the And that's the beginning. Jump to the end. What is your current setup when it comes to life with assistants? So I've got a chief of staff and a half dozen assistants that roll into that chief of staff.

Each assistant specializes in different things. So one helps me with work, one helps me with finance, one helps me with my kiddos, house, etc. I wouldn't recommend anyone they start with that many. You start with one and get to capacity and then you keep going to the extent your means and your ambition allows. But in my experience, I just experienced this time scarcity for most of my life of I just want more out of life. I want to spend more time with my family, my kids, do more work. And there's only so many hours in the day. And as I layered on more assistance, I eventually, when I got to six, got to the point where I was like, wow, I have this feeling of time abundance

where so much is taken care of that I can start thinking about new things that I want to do. And that, for me, was the most fundamental unlock. And it's not to say that's easy. It took me a decade to get there. No one's going to turn it on in a day. But it's possible. And it feels really good. And I think that's what most people are looking for in life is more time.

How do you come to think about time then? How do you regard it as a resource or a contributing element of people's lives? it's the most primary asset in the world it's the ultimate currency right uh i think lots of people want more money or want to be popular or uh you know want power if they're in politics i think these are false goals the real goal is to control your time and that's what we all want more of it's the only non-renewable asset you can't get more of it and uh yeah people have different uses of that time it can be to start a business or spend time with their family, but ultimately time is all we've got, and it should be treated as the most fundamental thing in the world. I think this is one of the reasons that this conversation can be pretty uncomfortable

for people, because it sounds like rich founder who began his career in the White House now has a small platoon of people who enable him in position of already material privilege to sort of maximize that reach. even more and to get even further down the line. I think the interesting thing for me when I was maybe early 20s was I started looking at some of the things that I did when I bought my first house when I was 27 and I realized that I really hated cleaning but that a cleaner in the northeast of the UK was 40 pounds every two weeks and that meant that I didn't need to buy a vacuum cleaner because she brought her own vacuum cleaner

and I didn't want a vacuum. And I don't think you need to vacuum your house more than once about every two weeks unless you've probably got kids, in which case it's every day. But as soon as you sort of accept that, well, is my time more valuable than, you know, three hours at 40 pounds per time?

Well, yeah, maybe it is. Or maybe I just really hate cleaning or doing the gardening or whatever it might be. As soon as you accept that, I think it becomes just one straight line from, well, there's little ways that I can claw back my time by using money or whatever other resource I need to trade for it in order to be able to not have to do something I don't want to do so I can do something that I do want to do. And I, in some ways, although a Navy SEAL team of assistance sounds quite unachievable for most people,

it is a single lineage from I have a cleaner or a gardener or someone who washes. my car, straight to, I have an army of people and a chief of staff. Yeah, look, I grew up in the Midwest in farm country, farm boy. We had no assistance or house cleaners or anything like that around, so I know how it sounds. But it's possible to get leverage without spending any money, right? You can use chat GPT to get started. We can talk about that. You can delegate to your friends, right?

if you don't have a single dollar to spend on an assistant, you can get a group of four friends together and say, hey, let's all babysit each other's kids one night a week, or you just got a free babysitter for those other three nights. So there's ways. That's such a clever idea. Ways to get leverage for all of us. And my recommendation to people is you start small

with whatever resources you have and you learn to delegate to an AI assistant. People talk about prompt engineering. That's just delegation. And as you get really good at that and you have the resources, then you can upgrade to an assistant with company like ours or an in-person assistant, which is even more expensive or, yeah, a fleet of assistance that runs your whole life. I've worked with, you know, billionaires who have teams of 50. It's totally mind-blowing. And that's out of reach for almost all of us. But I think everyone can take the first couple steps and you go as far as you want or you're able. Let's begin at level zero then. Let's say that. someone thinks, okay, I believe that time is pretty important. What is the, what is some of the

zero cost or very low cost ways that people can start to do that and then we can build up toward the platoon? Yeah, so level zero is you delegate to friends and family, cost you nothing. And this is group work. So you get together, you do the babysitting, you get together and you say, hey, I want to meet more friends in dinner parties. I'll plan one, dinner party once a quarter. If these other friends You also do it once a quarter, and now you get a monthly dinner party, making new friends, and you're only doing a couple times a year. So that's level zero, and that's where everyone should start. The next level above that is 20 bucks a month, chat GPT. You know, they're trying to be a human assistant. It's limited in what it can do today, but you can use it like a coach, like a, you know, a limited assistant. And so, you know, if you want to exercise more, you can go to chat GPT and say, you can use it like a coach, like, you know, a limited assistant. And so, you know, if you want to exercise more, you can go to chat, every day, ask me if I've exercised, and check in with me and give me a report card at the end the week. It can do that. Twenty bucks a month, you'll learn how to leverage it more and more over time. Once you have the resources for five, ten bucks an hour, you can go to Upwork or a company like

that and hire someone directly. If you've got $3,000 a month, you can work with a company like Athena, where we recruit, train, manage the assistant for you. And then if you want someone in person, just $100,000 a year, and then, you know, it goes up to infinity. This billionaire that I worked with has team of 50. He has eight executive assistants. The executive assistants all graduate from Princeton. It's totally wild and crazy. But, yeah, you start small with whatever resources you've got.

So you think about buying hours being more important than buying things then? Yeah, of course. I mean, what do people ultimately want? They want connection. they want time with their friends, they want time to exercise, time to learn. And that's what gives us meaning. And so, yeah, the most successful people I know, the happiest people I know, they're not buying things. They're not buying cars or clothes, they're buying time.

And the more time you buy, the more you have for everything else in life. Isn't it a strange inversion of how people often think about where their time should be spent, where their money should be spent, that, well, I've worked so hard, I deserve this holiday, but if you look at, what, a family holiday for four people,

I mean, how many sessions of a cleaner is that? I remember Sean Puri got a ton of shit on Twitter. And it is, it's so strange to me, the delegating thing being such a trigger for a lot of people, because it does sound very out of reach. I think it's a having staff,

especially when it's something that you can do for free. You can't fly the plane for free. You can't build the hotel for free. You can't go to the sunny place for free. So the value exchange is more apparent. But when it's you could wash your car for free. You could do the laundry for free. You could do these things.

There's this sort of odd bourgeois, luxurious, opulent kind of thing that's going on. But yeah, Sean Puri basically said, we haven't bought a new. car for a decade or something. There's no new family car. But we've got a chef. And I have a chef that comes around twice a week and cooks for that night and then meal prep stuff for the next couple of days. Just the words, I've got a chef. So out of touch. They sound so horrendously out of touch. I've got a chef. But if you were to say, I got a new car five years ago, you would not say that. But he netted it out. And it was pretty much the same cost. I think to get a new car every five years as it was to keep one for 10 and get a chef that came around twice a week or something.

Yeah, absolutely. I mean, my wife and I joke, we'd burn down our house before we let go of our personal team. They mean that much to us. And I think the words you're using do matter. It's I have a chef that signals this kind of separation. I'm better than you maybe is how someone hears it. another way to say is I help support another person. And I think this is a barrier for lots of people is feeling guilt about delegating of like,

is it okay for me to hand this off? It makes me feel different or it's giving this small little task to someone. But I like to reframe that and say delegation is your way of gifting to someone else. You're giving them a job. You're giving them income. The more we hire, the more we delegate, we literally just put money in other people's pockets. And it's more than money. It's a job and it's meaning and it's something, a craft that they get good at. And so, you know, the more you delegate, the more you give that

gift of meaning to other people. And of course, you get something in return, which is food or time or whatever it might be. Talk to me about the relationship between time and health. I think it's the most fundamental thing. So you hear Brian Johnson talk about sleep being the most fundamental. You got to sleep because if you sleep, then you can exercise. If you exercise, then you eat well. And those are the fundamentals of good health. But why do people not sleep much? It's not because they don't want to. It's because they don't have time. They're working too late. They want to spend time with the kids. And so, in my view, time is actually the most fundamental pillar of health. And learning to control your time, getting sovereignty up for it,

is how you then unlock good sleep and everything else that follows. Where are the places that people are wasting time, or where are they spending time in very low leverage ways, or in what ways is it being sapped and pulled away from them, that they might not realize? Yes, I think for most beginner delegators, they start by delegating things that sap energy and that are monotonous and annoying.

That's renewing a passport or a driver's license, it's calendar, it's inbox, it's paying bills. There's those things that don't require any cognitive, don't require any creativity. It's not why people get up in the morning. And so starting there reduces this just kind of like cognitive weight that you carry. Every day you've got to do X, Y, Z. But you take those things off, and then the things that remain are higher order.

It's planning, its goals, its aspirations, and those higher order things are much more exciting, more energy giving. And that is a wonderful challenge. So cognitive offloading is a mental upgrade here in that regard. Exactly. Yeah, the more you offload, the more time you have for the highest order things in your life. You know, I'd like to say assistance like a cognitive prosthetic for remembering, planning, sequencing, and just like inflammation damages your body in health, chronic, two-dos damages or impairs your mind.

and so the more we can free ourselves of those things, the freer and the more upgraded our mind can be. I think when it comes to delegation, a lot of people have a number of icks and concerns, probably quite a lot of hurdles to get over. I certainly know that I did and do, especially if you're agentic, hard-charging, get-after-it-yourselfer,

the prospect of giving tasks to somebody else, I don't know, I seem to have two categories of friends. One are those who can't wait to offload and another are those who can't work out how to do it. So what are the cardinal sins of delegation? So the number one I call pride, this is thinking it's better or faster to do it yourself. This is the cardinal sin of delegation

because it's true. It actually is faster and you will be better at doing something the first time, whether it's sending an email or planning a party. But the hundredth time you do it, you won't be faster and better. And so it takes effort to delegate and to hand that off, but you have to get over the fact that you could do it faster or better, but you could be doing something else. So that's the first thing, which I call pride. The second is guilt, which is real on the other end of the spectrum, which is, I don't even feel good about having this person manage the minutia of my life or wait on hold all day long. And for these people, my reframe is you're giving

this other person a job. And at companies like Athena, we recruit people who are excited to support and take care of you. It's really like a caretaker job. And for them, they get to take care of someone else. And that feels good. And you have to delegate in order to give them that opportunity. The other blockers, I call it selfishness, which is just not opening up your life enough. If you don't give access, your assistant can't really help you. If you don't have access to your inbox, your calendar, the other parts of your life, they have to have the context to really get in. And then you have to be willing to give them lots of hard, sometimes uncomfortable feedback.

It's like, hey, I liked how you did this. Oh, I wish you could have done that better. And giving really detailed continual feedback is something. only top 1% delegators do. Most people struggle because it takes extra work, and you have to be willing to make someone feel a little bit uncomfortable. So you have to learn how to give that hard feedback in a way that's encouraging, supportive.

And then the last blocker for most people is just a lack of commitment. They will try it for a month or try it part-time. I've never seen that really work to get ultimate leverage. The people who get the most leverage are going all in. They're doing it for a decade. They're all in with a full-time person. and you look at the clients we work with, the ones who have really transformed their life,

they're working with the same person for many years. And that person becomes their second brain, knows them like a little sister. That's how I think of my assistant. I've worked with the longest she knows everything about me. And that takes this long-term commitment. So just putting a toe in doesn't give the assistant the required depth of relevant.

resolution to be able to actually look at what's going on in life. They need to be able to see everything and the gains accrue as they start to see more. It's like getting married, but only going on a couple dates. You know, the marriage and I think all good things, wealth, relationships, they compound. And the power of compounding is it gets better and better gradually over time. And that's true with an assistant, the more you do, the deeper and better it gets. Right. Okay. what is your perspective on the difference between a VA and an in-person PA or something? Because what you're talking about here with Athena, a lot of this are virtual assistants,

and presumably people can get these for cheaper, but your virtual assistant might be able to organize a cleaner, but can't be a cleaner. They might be able to organize someone to collect your Amazon parcel, but they can't go and post it themselves. So how do you think about piecing together different assistants in that sort of a way? Yeah, I mean, if you have the budget for both, that's the best. You have someone in person for arms and legs and to run around and help you and someone in the cloud who's virtual. Typically, someone who's virtual is less expensive. You know, Athena, our assistants are based in the Philippines or Kenya where you have great talent at more affordable rates. And in person, you know, if you're in New York or SF or Austin, it's just going to be more expensive. So, you know, I recommend people start virtual and then as you have resources, you can do more. the team and I were just joking, there's these humanoid robots

that are now getting closer and some of them are teleoperated. And we're like, you know, we're not far away from you being able to have a robot in your house that your virtual assistant can actually teleoperate. And so, you can be like, hey, can you grab me a coffee

and they could teleoperate the robot in your house and bring it to your desk? You know, that's, we're getting pretty close to that being a real thing. So that's, it's going to be a fun frontier when that happens. This episode is brought to you by Whoop. I have been wearing Whoop for over five years now, way before they were a partner on the show. I've actually tracked over 1,600 days of my life with it, according to the app, which is insane. And it's the only wearable I've ever stuck with because it tracks everything

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Whoop 5.0 and that 30-day trial by going to the link in the description below or heading to join.wop.com slash modern wisdom. That's join.com slash modern wisdom. What is happening with AI and assistance at the moment? I think the number one use case for chat GPT is coaching, which is probably not far off. What you're doing, it's like help me with this problem. It might be a little bit more closet psychotherapist than a typical assistant. But yeah, what are you guys doing with AI? What's interesting with regards to how that can unlock people's delegation and time? Yeah. So our vision is we merge the best to human, best a machine into one product. And so the human is the U.S. Humans are good U.S. And then behind that human, we're building machine assistance that automate

more and more of it over time. And my analogy is like Tesla was self-driving. Elon built the first cars with steering wheels because you had to drive them. He didn't build them without steering wheels. And as you drive them, you're actually teaching the machine how to drive. And progressively, they automated.

They have assisted steering and auto braking, and then eventually full self-driving. And we view our work is similar. It's going to be fully human. And then gradually the machine will do more and more human will always be in the loop, but the human will do more advanced, more powerful, more creative

tasks over time, and the machine will do the more rote mechanical stuff. And it's effectively the AI will become an assistant to the human assistant, which will increase their memory, allow them to work overnight, do all sorts of cool productivity things.

But our view is the human touch is real and is going to last for a long time, no matter how much some of the AI promoters would like to say otherwise. But the combination is going to be a pretty cool thing. Yeah, that's cool. Around the, I can do it better or I keep finding frustration

when getting somebody else to do a task on my behalf, that can last for maybe a bit longer than you might want. How does someone navigate that challenge day to day? I think some of those expectations stating, I think some people think you just delegate and it works, and that's not the real world. The real world is you delegate and the first

version doesn't work or it's not exactly what you wanted, and then you give feedback. And you do it again, and the next time's a little better, and you have to have a high tolerance for failure, for iteration, but as long as you have a high tolerance for those things and you just continue

compounding improvements, then it gets better and better over time. But yeah, I think like most things in life, there's no easy button. You've got to invest in the partnership and, you know, we tell clients who work with us, if you just want to show up and want everything, your life to be perfect, it's not going to work. You have to invest, and the more you invest, the better your partnership will get. And in fact, if you look at the best assistance at Athena, the kind of top 1%, they just so happen to work for the clients who are the best at Delft. not a coincidence they've become so good because the client is so good at exporting their thinking

giving feedback praise and recognition helping build up their confidence when they make mistakes helping correct them and steer them and it really is a marriage of sorts and so as long as both parties are really invested in it it can be super powerful but if it's one-sided ain't going to work how do people get better feedback i think this is something that lots of humans struggle with. So number one thing is do it more often. People just don't do it enough. The number two thing is you need to be way more detailed. Hey, this was good or hey, that was not good, not helpful. Helpful feedback is very specific and it's very timely. It's, hey, this task you did, I liked, because you were super fast, you were detailed, XYZ, or hey, next time I'd like you to do this

differently and be very specific. So that's just the most. You need to be doing it constantly and needs to be very detailed. The other thing that is not obvious to lots is that you should really be exporting your own personal algorithm and your own thinking as you delegate. So kind of a novice way of delegating would be, hey, will you plan a dinner party for Chris and me when I'm in Austin next week? That's probably not going to be organized the way you want because there's not much detail there. The better way to delegate would be to say, hey, when I have dinner parties, here's what I like them to be. I want to be six to eight people. I want there to be a variety. Here's where I go to find party invites. I go look for people who have this to order of company or these source of interests.

You basically create an algorithm or a process. The person can follow step by step. And then they have like real guidance for executing. And then they execute. And then you go back to that process and say, hey, there's three steps in here that we miss. They will refine this further. That's continue to tweak the algorithm. People who are kind of engineering minds, this comes very naturally, but for other people, you have to learn how to do it. It makes sense to say not just this is the thing that I want, but this is how I typically get there. If you have a person who helps you do meal prep or helps you with your emails or something, you don't explain to them, well, actually, I like my eggs to be a little bit firmer. So typically what I do is,

or when I send a reply, I tend to put two signatures in because it actually shows it differently on the thread. And I think that link's important to show a little bit of reputation. So this is how I do it. I suppose it allows people to see your thinking. Exactly. In AI world, there's this concept of context engineering. This has become very popular to make the models more performant. You have to pipe in all the context because the models are very smart, but they don't have context. And the same is true with delegating to an assistant or otherwise, is like, if there's not enough context, it's impossible to do it well. And so your job as a delegator is to export all the context you have. And what's not obvious is that you have a million

times more context than you could possibly realize. And it's just sitting there and it takes practice to export that. And that's why these things compound over time, because there's no way to export at all on day one, but over the course of compounding for months and years, you eventually get there. How do people build a tolerance for inefficiency? Because especially if you're the sort of person who thinks, I might get a cleaner. I might get a cleaner for a little bit. Or I'm going to, I'm going to get someone to do the gardening because I fucking hate it. And I kind of suck. And I really wanted to spend my time on Sunday mornings with the kids instead. If you're the sort of person who is prepared to make that cognitive leap, you're also

probably a perennial over-optimizer in any case, which means that when you see inefficiency, that is a particular bug bear to you. So how do you improve your tolerance for inefficiency? I think part of is just realizing it's the right trade. So, you know, does Michael Jordan mow his own lawn. No, but you know what? I bet if he did, he'd be effing amazing. And whoever does it is never going to reach his level potential, but he could just be doing something else. And so it's like, do you want to do something else, even if something's done inefficiently? That's just something you have to accept. Another kind of framing I have is Elon sometimes talks about teams being the vector sum. So the company is a vector sum of all the humans involved.

And, you know, it's just a fancy way of saying there's inefficiency because these vectors are not perfectly aligned. And the only way to get more output is to have a higher tolerance for inefficiency. And that's just a fundamental rule of the universe is if you're focused on more and more output, there's going to be more and more inefficiency because more humans are involved. Right. Okay. So inefficiency is a price that you need to pay to increase output. overall. I mean, I remember in university learning about dis-economies of scale and one of the biggest ones being communication, that you know everything that you need to know by design of the fact that you already know it and you're the only person that needs it communicating to. As soon as you

got two people, well, they need to know what you now know and some of it gets lost in translation. And as soon as you scale up to 13, there's lots that gets missed and lost. But your total capacity for overall output has gone up, even though the efficiency is less. 13 people in a team is less efficient than one person 13 times in 13 different companies, but the total output of the company that's got 13 staff is greater than any of the individuals that have got one. 100%. Yeah.

You know, how do you, another way of asking this question is how do you measure your life? Do you measure it by efficiency, or do you measure it by how many times you're going to date with your wife? or how many times you exercise, or how much you spend time doing a hobby. Those outputs are what you actually care about. You don't care about the inefficiencies that were involved in creating those outputs.

You just want that good life that you want. Wow. Yeah, okay. What about the relationship between leverage and ambition? Because it seems to me that lots of people who are very ambitious lean into their leverage, but I get the sense that it can become a feedback loop as well. So how do you come to construct

ambition and leverage? Yeah, this is one of the more counterintuitive things that we discovered as we've coached clients on delegation, which is most people assume that powerful people or successful people have all this

leverage and that's how they become ambitious. That's why they have all this ambition. Or because they have all this money, they can create all this leverage. But what we see in practice is that People's ambition clearly grows linearly as their leverage grows. And the reason for this is pretty clear.

When you are overwhelmed by life, when you have more than you can possibly handle, your ambition just narrows because you're trying to get through the next 24 hours. But to the extent you take this cognitive load off, you share it with someone else, this partner or assistant, you now have the cognitive space to think about bigger goals, bigger aspirations. And so as you unlock more leverage, your ambition actually grows. I've seen this in my own life during times with my first company Thumbtack when we're just drowning with all the work and the challenges.

I was just focused on that thing. And there was no space in my mind to consider new aspirations. but to the extent I've gotten more and more leverage every time, you know, what do you want to do with it? Oh, it's like, do I want to start another company? Do I want to, yeah, do more cool things from my friends? And that's how your ambition can really grow. Well, I mean, how many people say that the reason they can't think about the important

is because the urgent is in the way? And I suppose that means that the more time you spend not doing the urgent, the more important stuff you have access to. That seems like a pretty good trade. Exactly. Yeah. You got to do the urgent, so you have the right and the opportunity to do the important,

and to the extent you can offload the urgent, you get more than important, and that's a beautiful trade. Is there a relationship here with willpower as well, that not having to do bullshit means that you can use your willpower on stuff that somebody else can't do? Absolutely. I mean, we also have a limited number, a little amount of willpower and work ethic, right?

It's like I always say I can work 10% more, 20% more, but I can't work 10 times more, and I can't have 10 times more willpower. It's just impossible. I have God and nature has granted me with a certain amount of those things, and so I have to use that limited willpower and limited agency in the best way possible.

and I don't want to be using my limited willpower on my passport or no. It's just not the highest order thing in my life. I would rather be using that to help a friend solve a problem or accomplish something in my business or something else. And so I think you can unlock more willpower into higher order things, the more you unload these more monotonous things. Before we continue, you might not realize it, but mouth breathing at night is wrecking your sleep, recovery and energy the next day.

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start with chat chitpity or in person or whatever it is. And the beginner way to delegate is offload pain. So make a list of all the things that you don't like doing that reduce your willpower that make you unhappy and start there. And this is kind of monotonous stuff. It's like your inbox, your calendar, pain bills, passport renewal, etc. This might take a year to offload all these things. As you offload more of the-

I need to pause there. that the um what a lot of people might assume i think and i know i certainly did when i started working with assistants was this is going to be the immediate fix for me i'm going to introduce this person into my life and i'm never going to have to do anything again but uh being modest with the speed at which this integration is going to happen effectively i think is a a really really good idea yeah look uh my recommendation is you you do this as a new way of living. I think that's the right way to do anything, exercise, meditation, or whatever. If you're doing it for a week or a month, kind of worthless. But if you can do this

for the rest of your life, then it will compound. And yeah, you start with pain, unload, all these monotonous things. And then once you do that, then you start chasing your aspirations. It's how do I, you know, for me, this is how do I make more friends? How do I deepen my relationships? How do I have the best marriage possible, how can I be there for friends in need? And those are the sorts of things that assistant can actually help you with, but you're not going to actually do that unless you've got your passport renewed and your credit card bills paid and everything else done first. So that's kind of the high level, remove pain and then increase your aspirations and go for your goals. In terms of the levels of delegation, the way most

people start delegating is they delegate by task. Hey, will you help order these flowers for my wife's birthday? That's a good way to start, but it's the least powerful way to delegate. The more intermediate way to delegate is delegate by process, is what we've talked about, is like, hey, when I give gifts to my wife, I want X, Y, and Z, here's what she likes, here's what she doesn't, and you're now teaching your assistant how to do things at a higher level. The next level, more advanced delegators do is they delegate by goal. And this takes often years where you've mind-melted with your assistant and give them so much feedback that you can just delegate a goal and they can execute it in the way you want. So this is, hey, I want to exercise more. I want to protect my sleep. I want to spend

more time with this person in my life. Architect my calendar, reject meetings that don't fit this priority. No one can start by delegating by goal. You have to build your way up, but this is where you want to get to. And then the highest level of delegation, I call it clairvoyant delegation, this is the nirvana of delegation. This is where you have given so much feedback and your assistant is so in line with your personal and professional goals that they can anticipate your needs. And the first time you hear about a task is when it's done. This is a level that is very difficult to reach. I would not promise anyone gets this on week one, but this is what you should aspire to get to. And I have glimpses of this now all the time.

It's not something I live in constantly. But my assistant will reach out and say, hey, I know you'd want me to do X, Y, Z. It's already done. Here, you just got to sign this. And that is where you're like, yeah, this is good. And, yeah, it unlocks so much cognitive load that you didn't even have to delegate it. You don't think about it. It was just, hey, it's done.

and now you can go on to do something else. I suppose that's one of the current limitations of AI that by design the prompt needs to be done before the task is completed. I'm not, I'm sure there probably is somewhere, but I don't think any of the LLMs at the moment are going to pop up on a Monday morning and remind you that you need to do the thing

or have done the thing and then tell you that it's been done on your behalf. It's still very sort of top down as opposed to bottom up. Yeah. Yeah. I do think AI is going, A is just going to get better and better.

And I do think there is an opportunity for, and I think lots of AI labs are going to do this. They're going to start watching your screen as you work, and they're going to look at what you're doing, and they're going to proactively offer opportunities for them to help you. And this is, we've built something like this at Athena as kind of internal testing tool, where we watch, this is just using it for internal employees,

but we watch them as they work, and then we automatically offload a task they should delegate, but they haven't vocalized to their assistant. And the person who built this internally, the majority of his delegations are now machine generated. That means he didn't say anything. He's just working on his computer. The machine is effectively watching.

It's identifying things that his assistant could help with, and it sends it to the assistant. Now, of course, the human's in the loop, and is going to say, oh, Chris would want me to help with this. I'll start working on it or this one's worthless. I'll say no. So I do think that is going where the world's going. I think we're getting to a world where you just work, machines watch you,

they identify your goals and then pass it off to a combination of machine and human assistance for the execution. What are some of the potential negative externalities of a world where people outsource incorrectly or they do it too much or what are some of the ways that people can get this wrong? Yeah, I hear some people say you shouldn't delegate your life

and I think that's right like you shouldn't delegate spending time with your kids or with your wife you should delegate the things that you don't want to do to do the things that are meaningful to you So I think that's one way.

The other thing is I think you need to treat your assistant with the respect and love that they deserve, right? This is not just, hey, do this for me. This is, hey, we're a partnership. I want to help you build your life. I want to give you more opportunity, more income. You're going to help support me, and it needs to be a mutual thing. This doesn't happen very often, but we've had to fire a few clients at Athena who just, like, weren't kind to show their assistance. and that's unacceptable to us.

We only want to work with people who are kind and generous with their assistants because our assistants are there to take care of you and they give so much that they deserve that same in exchange. Yeah, I worry, there's been parts of my life where I've got concerns that my tolerance or my resilience for bullshit, which is inescapable,

may become more finely attuned as I don't deal with bullshit on a daily basis. Kind of like, you know, these astronauts that go up to space and they don't need to lift any weight and then they come back down and they're unable to support themselves. Does that make sense? I don't know what you mean.

I live in Puerto Rico and getting things done in Puerto Rico is a little more difficult. I've heard slightly challenging with the maniana-maniana philosophy. And I am, you know, I'm lucky to have this team that's basically filter between me and the difficulty of getting things done. And, you know,

I do occasionally step outside of that filter. And I'm like, whoa, I've like forgot how hard this is. So look, I think if they're for like waiting in line at the DMV, I just like never need to be good at that. So I don't mind if my skills atrophy. But, you know, if something's important for your work or your skill set or your craft, then obviously you can't fully delegate it. And you need to own that and keep your skills sharp. And so I think if you delegate something like that, I could see that being a negative thing. But there's a hundred other things to delegate that are not core to your highest skill. And all those things, I don't really care if, yeah, my inbox management skills atrophy, just not my, not my focus in life. Yeah, yeah, yeah. In other news,

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How novel of a solution is this, given the expanse of human history, how recent is it? Because it can sound in some ways like, again, a cosmopolitan TikTok generation, Gen Z, chat GPT solution to well people should just be able to sort of go and get it man yeah how how recent is this versus how sort of steeped in history is we did some fun research at Athena we actually used AI to do this we

we got a list of thousand of the kind of grates of history and downloaded 10 biographies and all of them and then looked for how they delegated and across all sorts of of people, Cicero, Newton, Caesar, Einstein, Voltaire, Gates, Churchill, Picasso, Buddha. All of them had personal assistance. And it's not a coincidence because these people did, not 10x, but like a thousand X more than other people have done in history.

And there's this kind of great man view of history that one person does these great things. And there's some truth to that. But the reality is there's actually a team and there's an organization and there's a there's typically an assistant who is helping this person accomplish great things. The history books just don't put those people on the cover. But that's how it's actually happened. And, yeah, it's fun reading these stories. I'm reading a biography of Cicero right now,

and he has an assistant who is, yeah, helping him manage the Roman Empire and trying to protect the Republic. And this guy is not, you know, the person we learn about when we learn about history, but it was important. And so, you know, our view of this is if you want to accomplish small things or great things, it's helpful to have an assistant. There's also funny stories. So Catherine the Great, I think was one of the greats at delegation.

She delegated not just managing her empire and rewriting the laws, but she also had someone, she delegated her dating life. And so she had someone dedicated to first dates and to testing, quote, male capacity. No way. Yeah. And that person kind of was running top of funnel for her. And I'm like, dude, Catherine, you are an OG delegator. Savage.

Holy shit. Insane. That's like P. Diddy's delegation. The Wright brothers, I've got to. two books about them. My housemate George is obsessed. And they delegated the first design of the plane engine for the kitty hawk, right? Correct. Yeah, Darwin delegated this whole army of fact-gathering assistants to collect data for the origin of species.

Edison delegated to an assistant to find the filament for the first light bulb. They found it in Kyoto, and there's actually a shrine that exists in Kyoto today to the assistant who found this. So hang on, hang on, hang on, hang on. So I have not failed. I have just found a thousand ways that I did not succeed. Thomas Edison did not actually technically come up with the design for the filament himself. It was just someone on his team.

He delegated it. He said, I need this filament. Someone needs to go find it. But yeah, he gets all the credit and that's fine. That's how history works. But it's not how. I mean, the Wright brothers, right? I don't think the first design was the one that worked.

But there was a, there's this really cool line. I think it's the photographer who took the pictures of the first flight when the Kitty Hawk was up. And he referred to the Wright brothers as the workingest boys that I ever saw. It's like just like this pure early 1900s Americana kind of sentence. The workingest boys that I ever saw. He's talking about their single-minded nature. their agency, their personal sovereignty, and so on.

But the first engine design wasn't done by them. So it's like the delegatingest boys that I ever saw. Exactly. Look, you know, history doesn't award style points for doing it all yourself. History awards points for getting it done. And the way you get things done is with the team. And for some of us, that's an assistant, for other people, you know, Steve Jobs, he had a team of 10,000 people who are helping him bring the iPhone to life.

But yeah, you shouldn't try to do it all alone. No, if Steve Jobs can't do it alone or Edison can't do it alone, you shouldn't try to do it alone. It's a good point because I think the humility, certainly the humility that I would feel as a Brit, who am I to outsource this? My life's not as difficult. And I suppose it's an obvious criticism to say, well, yeah, the president needs to. an army of assistance. Of course he does. He's the president. But I'm not trying to do that, so I don't need that. But the flip side is, yeah, also, you're not the president. Like,

you don't have the capacity of somebody like Thomas Edison or the Wright brothers. So given that, yeah, your goals are more mediocre and more humble, but so is your ability. And I think compensated appropriately. The user and Napoleon and Lee Kuan Yew needed an assistant. Think how much I need it. They're some of the most high-capacity people in the world. Yeah, you're exactly right. Have you looked at the neuroscience of delegation, like how it appears inside of the brain? Because I imagine that there's a lot of open loops that can get closed off. I also know that there's a hierarchy of how different tasks, new tasks, get attacked with certain areas of the brain. brain, System 1 and System 2 from sort of Daniel Kahneman stuff, it seems like a pretty obvious map

from doing it externally with a different person to what is already happening internally within sight of our brains. Yeah, delegation goes back to origin or species, and our brains have this relentless desire to optimize both energy and energy and information. And because of that optimization, it has, the brain has crafted this hierarchy of tax. distribution where complex novel tasks are tackled by our prefrontal cortex and routine tasks are offloaded to lower and more automated neural structures. So we like to say that it's not that our brain was merely wired for delegation, but it was wired by delegation. And it's just built into our brains from the very beginning. We delegate inside our brains and now we can

delegate between brains. What are these life experiments that you did? You did pretty much every year, I think, for a while, did some wild annual test. What did you learn from doing those? Well, I just, I'm experimental, so I just like trying things and ripping life up. You know, I think one of the first things I did after I left my company Thumbtack where my meetings, I had meetings from 8 a.m. to 10 p.m. all day long, and I felt like I just didn't have sovereignty over my time. And so when I left, I said, I'm going to work with no calendar. Zero meetings.

If you want to talk to me, call me, let's go WhatsApp or voicemail. And that was one of the most freeing things I've ever done. It's not something you can always do. But I certainly recommend to anyone who has a chance to kind of work without a calendar for even a little bit, it's a beautiful thing. Okay. And what about the delegating by voice solution? Yeah, so there are, there's a hierarchy of how you delegate. And most people delegate with their thumbs on their phone, worst way. Kind of better than that is to delegate with all your fingers on email. But the best way to delegate is by, by the best way to delegate is voice where instead of typing things you voice note and I tried for a year just delegating almost exclusively through voice and voice is way more powerful than other mechanisms of delegating

because you can talk three to five times faster than you can type you can do it between meetings in an uber at the gym and it's I think it feels less arduous as well it's like I've just got this thing trying to work how do I want to say this I've got to type the thing out as opposed to hey, I need flowers. I think I need, what do I need? Flowers. I need flowers. And today, I need flowers today. And then it's kind of done,

as opposed to working out what needs to go through your thumbs. Yeah, and, you know, to the point of how do you give better feedback, the way you give better feedback is you do it by voice. Because if you have to type up a page of notes, you're just not going to do it. But if you can just be like, hey, here's what I liked, and you talk about it as you walk in the park, and you talk all day long.

Yeah, I think it takes some training to learn to delegate by voice. Some people are a little uncomfortable. with it, but if you look at the top delegators at Athena, they all delegate by voice constantly, just all day long. Okay. Start of here, a lot of people have got new resolutions, myself included. One of my big ones is to reduce my time on my phone. How have you managed to reduce phone use, and what are some of the strategies that you've learned around that? So the first thing I tried, you know, there's this time app on your phone that just shares how much time you're in different apps. Weak source.

Weak source. Totally. I tried using that. It's just useless. And so what I, the experiment that worked for me was when I went to buy a new phone, I kept my old phone and I downgraded it to what I call my freedom phone. And I deleted everything from it except the bare essentials. I can Uber, I can make phone calls, but I don't have email, I don't have all my messaging apps, I don't have all the bad things.

And I actually have gone so far that I've banned all new sites, checking the price of crypto, all sorts of other stuff, and my wife has the code, so I literally can't unlock it. So this freedom phone I call is what I take out of the house with me, and it's got the stuff I need, and everything else is totally locked down. the only thing I've done that's worked because it's literally impossible for me to use it for anything distracting. And I don't, for me personally, I don't know about you, but I don't mind if I'm on the phone a lot if I'm like making a phone call to a friend. That's cool. What I don't like is just like passively picking up the phone to check notifications. That's just a waste of brain power and shouldn't

be doing. And this freedom phone that's totally locked down has solved that for me. That is a good point. And, you know, people upgrade a phone every two years, maybe, something like that. And by the time that, you know, two iPhones from now's iPhone comes out, you'll get 300 bucks or maybe 200 bucks at trade in. I don't know what you would get. But I know it's not a, it's not concordant with the amount of value that the device brings. It's certainly not like a $200 for that phone. Like, fucking, yeah, I would.

Even if the battery sucks a little bit. So what I would do is I would actually make the new phone, the freedom phone, and I would make the old phone, because the old phones kind of got to be tethered to. But I've been a proponent of this for quite a while. I think my most extreme was three. One was the cocaine phone. Another was the kale phone. And then a third one was Wi-Fi only. And that was what I actually did morning routine stuff on.

So that was meditation apps, that was Kindle, audible, maybe podcast apps, all my breathworks stuff, my logins for all of the different personal development things I was doing. And I went back home, it's so funny. I was back in the UK over Christmas. And I was back in my old house and I was in my old room, my old bedroom, which people can go back and watch the first episodes from the show ever were recorded in there. And I'm sat on the couch, this little couch that's on the right hand side. And I've got this iPhone fucking, it must be a.

six maybe or a five or something it's ancient technology and i realized it's the only phone that can still control the lights in my house because that was the one that the phillips hue system had been connected to so i'm there trying to fight with this decade old iPhone in a desperate attempt to try and get the lights in my bedroom to turn on and i've been flying i flew from kawai to the uk it's 28 hours or something basically a day and a half plus 11 hours of time change it's a fucking nightmare I get in and then I'm battling with this phone. And in some ways, it was super annoying, but in other ways it was really lovely and nostalgic.

So, yeah, I've tried, I think, as a pretty easy sort of low-entry, accessible way for people to spend less time on their phone. And a good solution here as well is if you do use the old phone, I guess people don't use physical SIM cards anymore, but if you move the SIM to the one that you're allowed to take out of the house, what that actually means is that the old one only work, the cocaine phone only works on Wi-Fi,

which means that if you take it out with you, it stops working, which is, you know, great, but you're cementing yourself, you're tethering yourself to your house. I have a friend who had a real phone addiction,

and he had killed phone entirely and just carried a laptop with him. So when he wanted to call someone or do something, he'd have to open the laptop, and it was a real pain in the ass, and it worked, but yeah, that's kind of, that's real like AA. That's desperate times.

I mean, the other thing is you don't have to have two phones, right? If you don't have the money to buy a second phone or to, you know, use an old phone, just make your main phone the kale phone. Just don't have any of that stuff on it and have it on your computer. And I have, you know, I don't mind if I'm WhatsApp and whatever on my computer because I'm getting work done. But just the passive stuff is what's toxic. Before we continue, getting mobile data while travelling is still way harder than it should be. Public Wi-Fi is sketchy, roaming charges are the worst, and buying SIM cards in a foreign language

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And if you haven't activated your data plan or installed the ESIM, Saley offers a full refund within 30 days, no questions asked. Right now, you can get 15% off any data plan by going to the link in the description below or heading to saly.com slash modern wisdom and modern wisdom, a checkout. What do you do from a distraction limitation standpoint when it comes to your laptop setup? My laptop setup, I kind of let everything go. It's not a problem for me. I'm just like in work mode. And so I let everything through there. Okay.

Is that something you work on? A little bit. Yeah, me and the boys did a big series called Life Hacks back in the day on the show. And a lot of what we were doing was trying to constrain distractions through environment design through digital environment design. And Cold Turkey is a really fantastic solution for this. It's a website blocker. You can schedule stuff in advance.

You can just give it the websites that you use most frequently. And there's a period where Johnny was using something called Frozen Turkey, which is a feature on Cold Turkey that shuts your laptop off. So it's not just blocking certain websites. It literally will not let you get onto your laptop. And you can set certain stuff up. one sort of SOS, I desperately need it. We break glass in case of emergency thing.

And then I'm pretty sure there's another one that he set up where he had to donate money to charity if he wanted to get. That's good. It's like every time you go, it lets you, but then it like just auto debits your account. I think that's what he did for a while. But he was trying to. But then you're like, well, now I'm giving you charity. So I guess. Actually, I should use my laptop more.

Yeah, exactly. It's noble. It's noble for me to do. be a charity you hate. You're going to give to the opposing political party. That'll be good. That'll be good. All right.

So let's say that someone's made it this far and they're at least partly convinced by your thesis. What are the remaining objections typically or what are the fears that people have and how do you overcome those? Yeah, I think number one is fear of failure. Will it work? And that I say it's not going to work on day one. You just got to go for it and it will compound. It will go better over time. The other thing is a lack of control and trust.

Some people have trouble trusting others and letting go of control. And what we say is trust should be built over time. so don't give your bank account access on day one. You start with more limited access, and then you grant more and more access over time. I've worked with one of my systems for every decade, and she has basically access to everything, but that takes a long time to build that trust.

And so you kind of go at your own pace, you don't have to go faster than you're comfortable with, but you've got to give up some control if you want to get more leverage. That's just part of the game. And then I think the... The other fundamental blocker for lots of people is just like knowing what they want more of. And you've got to have this thing that draws you into it because it's going to be activation energy.

There's going to be investment. And so you've got to have a vision for how you want your life to be better. It's I want more time to start a business or I want more time for my family or my kids. And I think if you have that specific goal, then delegation is not about a task, which is kind of the level. It's about unlocking something that's more meaningful to you. What? I'm trying to think about, let's say that somebody onboards an assistant, but they need somebody that's in person or they're not using Athena. What are the best resources for how to train that person?

Is there how to create a great assistant coaching course? Is there some sort of masterclass that people can follow? Where would you anticipate or where would you suggest that people go to for that? There's nothing that's fantastic out there. But if you go to playbooks.adena.com, we've built some of our favorite playbooks for things you can delegate. So you can come look at our website. And, you know, I think the best way is just to get started and to do it yourself. I've watched a bunch of YouTube and read a bunch of books,

and the reality is there's not a lot out there. When we started Athena, our goal was to recruit and train the best executive assistants and just match them with clients. And what we found after we matched the first 10 clients is every single client said the same thing. How do I delegate my inbox? How do I delegate date nights?

And so it became clear to us that we'd have to invest as much in teaching and coaching our clients as the assistance. This is kind of like it's a marriage. we're both in it. And so we've invested a lot in building those playbooks, creating the coaching to help people. And at some point, we'd love to kind of open source that

and share that more with the world. But right now it's all internal. Is it possible? I have to bring this up. Whenever I think about assistance and especially hiring assistants, one of the first things that I think of is an episode of Family Guy

where Stewie made himself a clone that was called Bitch Stewie. Bitch Stewie basically did all of the stuff that Stewie didn't want to do. So he made himself an assistant. And he was a bit sort of slower and kind of, there were a few chromosomes missing. And then Brian saw bitch Stewie and really wanted his own clone. But instead of making it himself, Stewie got bitch Stewie to make bitch Brian. And bitch Brian, like, ear fell off and he turned into a puddle and broke on the floor and stuff.

in your experience, how effective is it to get other members of staff, potentially assistance or other people, to do the hiring, training, like delegating the delegating? Is this still something that needs to be done by the principal? Or is there a way to outsource outsourcing? You can delegate almost everything. Including the active delegation. Yeah, but you have to delegate compulsory. of it. So, for example, if I'm recruiting an executive at Athena, I would not have my assistant interview the CFO. But what I would say is, hey, I'm going to go through my CEROM now,

open a voice note. Here are 30 friends I know who have cool companies, they know CFOs. I want you to pre-draft an email from me to this person asking for an introduction to the best CFO they've ever worked with. And then those emails get dropped in my inbox and I send those out. out and I have my assistant CC herself on the email. So when the responses come back, she can help schedule them. So, you know, my, when people say, like, what can I delegate? It's basically anything. I turn around, I say, what's your top personal and professional goals?

Tell me what those things are. And I'll tell you some ways you can delegate. I'm just like, for you, like 2026, Chris, what are your top personal and professional goals? build a world-class studio go on tour and not need to worry about whether operations back home are continuing and fix my health great and on health

how could you delegate components of that organizing testing speaking to the different doctors updating them on where these numbers are at and whether Chris has completed that course and whether he did those IVs, there's sleep people and there's nutrition people and there's IV people and they all need. It's almost a full-time job. Yeah, I mean, I've done, related to health, one of the first projects, kind of mega projects I did with, my assistant was look through my calendar and my inbox for every doctor's appointment I've had for the last

decade. And then from my inbox, reach out to those doctors and ask for my health records, because it has to come from my inbox, and then centralize all of those test results, all of the doctor's visits, put it in one spreadsheet. And this, you know, I wouldn't just never have done otherwise. It just wouldn't have happened. But now that I have it, I can drop that in the chat GPT and be like, hey, what's, what should I do about my cholesterol? And it can look over the last decade and make real recommendations. So yeah, you can always break it down into product. that someone can help take off your plate. Yeah. Jonathan Swanson, ladies and gentlemen. Jonathan, you're awesome.

Athena's a fucking dope company. I've got a bunch of friends who rely on it, and I think what you're doing to emancipate us from the drudgery of online internet work and to outsource it to people who actually love to do that, I think is really, really cool. If people want to check out more of what it is that you guys do, where should they go? You go to Athena.com, and we'd love to help you get more leverage. And thanks for having me on. You do know that one of my friends who I think uses your service named his daughter Athena. I did not know that, but I had twins this summer, and my wife and I named one of our girls Athena.

Let's go. There's three Athena's in the world now, technically. Jonathan, I appreciate you. Thank you, brother. Thank you so much. If you're wanting to read more, you probably want some good books to read that are going to be easy. and enjoyable and not bore you and make you feel despondent at the fact that you can only get through half a page without bowing out. And that is why I made the Modern Wisdom Reading List, a list of 100 of the best books, the most interesting, impactful and entertaining that I've ever found. Fiction and nonfiction, and there's real life stories, and there's a description about

why I like it, and there's links to go and buy it. And it's completely free. You can get it right now by going to chriswillex.com slash books. That's chriswillex.com Books