(upbeat music) - Hello, and welcome to another episode of All The Hacks, a show about upgrading your life, money, and travel. I'm your host, Chris Hutchins, and I've recently gotten a ton of questions from you, and even from friends and past colleagues about time management, delegation, and specifically about hiring and working with an assistant or EA.

So I thought it would be a great idea to invite my friend and founder of Levels, Sam Korkos, who is an absolute expert at delegation, to talk about delegation broadly, as well as the entire process from assessing the need to hire an EA, ways to hire one, how to work with them, and some challenges that may come up.

Believe it or not, Sam has four EAs, including one he's worked with for over 10 years, and yet somehow has never actually had a synchronous one-on-one direct conversation with her. In addition to all that, Sam shares my passion for using software, automation, services, shortcuts, and now AI to outsource, onboard, and optimize so much of his life, and he is so good at it.

So I hope that this is really a masterclass in all things delegation and focusing on what matters. And if you noticed the length of this episode and thought, "Wow, that's way too long," I tried to edit out as much as I could, but I wanted to leave all the good stuff, and there was just so much.

So my goal is that even if you listen to it in its entirety at 1x speed, I think you'll save more than that much time, if not 10, 100, or even 1,000 times more time by putting some of what you learn into place. And to help with that, I worked with the team at Oceans, which is a company I use to find my amazing assistant, Pasani, to put together a guide that covers 10 tactical steps you need to take before, during, and after hiring an assistant to create a paradigm shift in the way you work.

It covers everything from changing your mindset to training yourself to delegate and more. If you wanna check it out, it's totally free, just go to the link in the show notes or go to allthehacks.com/delegate. Or if you're interested in getting an assistant, you can check out oceansxyz.com, and I'm pretty sure that if you tell them you heard about it here, they will hook you up with a deal.

Okay, I am so excited for this conversation with Sam, so let's jump in right after this. Do you all remember episode 122 when I spoke to chef David Chang about leveling up your cooking at home? If not, definitely go back and give it a listen, but one of his top hacks was using the microwave more.

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- I think it's probably the most important skill to develop as a leader, to be able to increase your capacity, to be able to deliver more value. The amount of time that you have in your life is finite. And so the only way at a certain point in your career that you can deliver more value is to learn how to delegate to other people, to be able to extend the number of hours that can be contributed to a certain initiative.

So ultimately everyone who intends to reach some level of success in their life needs to learn how to delegate. That's probably the highest level explanation. - The only pushback I'll give you is you said a leader and guess we could think about leader more broadly. The average person listening might think, oh, this is a skill that's relevant for people who are running companies or managers.

And I would just say, you'll learn this soon enough, but with two kids, I feel like time shrinks because there are more responsibilities at home and it can also become a really important skill for anyone beyond just leaders. And if you expand the definition of leaders bright enough, then I guess it includes everyone.

- Yeah, and it really depends on how abstract we wanna go with this, but like in many ways, you're delegating the labor of growing crops to a farmer and then you're buying their service, you're buying the product from them. So it's just a little, you're already delegating many, many parts of your life, whether you realize it or not.

And so in order to achieve anything bigger than what you would just be able to do by yourself with limited capacity, you have to be able to learn how to work with other people. And that's truly what delegation is. - It's funny, I was gonna ask you about some of the benefits you've seen in your life.

And now I'm like, well, one benefit is you don't have to be a farmer. (all laughing) But how do you think, if you rewind and look at now, becoming great at delegation benefits your life and changes your life in what way? - You can do more things. Often when I'm coaching people that I work with or talking to friends who are struggling with these things, one of the biggest challenges that I found of trying to get people to measure their time, to put things in their calendar and to measure their time, I think the biggest reason why people don't want to do it is that it really, there's an existential dread that comes with it.

When you have this list of all the places you wanna go on vacation in your life, it's like, I wanna go to India, I wanna go to the Bahamas, I wanna go here, I wanna go there. It's like, wow, this would be so amazing. And it's like, great, let's look at the rest of your life and how much time you have.

And it looks like you get to pick four of those. That can be a really unpleasant conversation. And so I think to recognize that you have a finite amount of time, and if you want to deliver on anything of value, you have to figure out how to get better at delegating.

And it doesn't mean that you have to pick one thing or the other, you don't have to say, I want to achieve all of these things. But if you wanna do something like build a piece of software that you sell to people, unless you think that you can do all of it, if you plot out the timeline of you doing all of these things, like doing a podcast, some people just do it all themselves, which is totally fine.

Some people hand off the editing, they delegate that. Some people hand off the promotion, the distribution, they hand off a lot of different pieces. And so you just have to figure out how far do you wanna take it and how much leverage can you get by delegating to other people.

- And if we push in this kind of like product manager way of the five whys, which I'm guessing you're familiar with, it's like, well, you have more time, you can do more things, but like, what's the real benefit? Do you feel more fulfilled in how you spend your days?

Are you happier? - One of the major aspects, and this is coincidentally something I was talking to somebody about today. One of the major benefits of delegation is just learning how to better manage your energy. And this is sort of a, I don't know if it's a woo-woo thing to say, but there are things that take your energy and there are things that give you energy.

And I think we've all experienced that of things that you're excited to do and things that as you're doing them, it's just crushing your soul. And you can do some of those soul crushing things for a little while, but eventually you burn out. And this is maybe a controversial statement, but burnout is a choice.

You choose to do things that you do not like to do. Everything is a choice. Your job is a choice. Everything is a choice. And you can choose whether or not you do it, whether you hand it to somebody else, whether you find something else to do. And so the why of delegation from that lens is you're choosing a path to do a job that requires a daily mode of operation that is sucking the life force out of you.

And so delegation is interesting because oftentimes the things that you find soul crushing are things that somebody else actually really enjoys doing. And then they look at what you're doing. Like in my world, I really like coding. I like programming. I like sitting in a dark room in a cave and just writing code for like 12 straight hours.

And there are people who look at that and say, "That is insane. I could never do that." And then I look at what they do, which is, I don't know, sales. It's like, "I could never do that. It is like my worst life is doing sales calls." But that's what they enjoy.

And there's no right or wrong answer here, but being able to delegate different skills for what different people want allows you to control more of your energy, and it allows you to have more stamina and reduce the risk of burnout. That's one of the major benefits. - When you say it like that, I can't imagine someone listening is like, "Oh, I shouldn't do more of that." Right?

Like, "I want to spend more time on the things I enjoy in life." - Yeah. - I love to highlight businesses that are doing things a better way so that you can live a better life. And that's why I love our sponsor today, Mint Mobile. For example, a few months ago, I got an email about our au pairs phone line saying, "It turns out you don't need unlimited data.

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Why aren't more people doing it in their personal life and their work life? - It's an interesting question. I can say there are many different reasons, some of which are more valid than others. Just from personal experience talking to people who've struggled with this, I would say one is some degree of insecurity where they feel like they don't like doing this thing, and so they assume nobody else likes doing this thing.

So they feel a little bit of guilt handing this task to somebody else who's also gonna hate doing it. But that's not necessarily the case. In fact, in my experience, it's very often not the case. I think some of it also comes from a place of insecurity around some imposter syndrome of who am I to tell somebody else what to do with their time?

And eventually, you just have to get over that, and you have to learn that the only way to get better at how to achieve whatever it is you wanna achieve is to get more comfortable handing off these tasks to other people. Some other recent examples is they feel like these are things that must be done, and they don't have the resources internally to be able to hand them off to other people.

If what your company really needs is sales, and you hate doing sales, but it is definitely the most important thing, and you can't hire other people 'cause you don't have the resources for it, then you might just have to grind through it for a little while. But I think what's important is figuring out what your exit strategy is.

If it's not the thing that you're excited about, you should figure out what the script is. If it really is ROI positive, eventually you'll be able to hire somebody to do it. There are a lot of different reasons why people struggle with it, but in my experience, one of the things that I try to do, I do once a quarter, a think week, which I just stole from Bill Gates, where I take one week off from communications, and I just think and read and write.

And I found that's the right cadence for me to get pulled out of the hyperactive hive mind of work and the day-to-day and see the whole forest and not just the trees. And so when people are in that mode of constantly churning and grinding and grinding, they often lose the big picture of, should we even be doing this thing at all?

Often the answer is just no. It's having that space to zoom out and think about what your major priorities are is really important. - I'm gonna go back through a few of the things you said. So when you talked about the imposter syndrome, one of the things that made me think was about your example about farmers, which was if you ship a package, you are inherently telling someone they need to go and deliver your package.

And I think maybe the more we can normalize the fact that we're delegating lots of things already, right? You buy something at the grocery store, someone has to restock that thing, order that thing. So that was one thing that just made me realize, well, I'm delegating a lot. And so if I'm uncomfortable doing it, I should just get over it.

Like it's just already happened. And I think that's helpful. I think part of it is not feeling like you can tell someone what to do. And part of it is feeling like maybe I don't deserve this or it's too elitist. I don't wanna be the one that tells my family and friends to interface with my assistant.

This happened to us when I had my EA try to get our daughter in for a last minute pediatrician appointment. And I was like, I feel so ridiculous calling the pediatrician's office or having someone else do it and being like, hey, could my boss's daughter get into the appointment?

And I remember when I got to the pediatrician's office, I was talking with the person there and I was like, oh, is this, it was that awkward. I was just curious. And the response was like, no, we do this for the doctors all the time. Like they were like, this is normal.

Like they were more, it was all in my head that it was not normal. Now I will say I've had friends who've pawned me off to their EAs to like schedule a dinner. There is a feeling when that happens of like, well, I thought we were friends. Now you want me to work with this other person.

Any thoughts around that whole kind of attitude and do you just have to get over it? - Some of it is just you have to get over it. I was talking to somebody not too long ago where he's really struggling with this. He's at a point in his life, he has kids.

He has a meaningful amount of personal wealth. He has a lot of responsibilities and he's totally underwater. And I was talking to him, I said, you need somebody to help you manage your household, a head of household. Like this is a role, people do this role. And he said, I can't because my mom would judge me.

Like my mom would not approve of that and it would be really difficult. And I don't know what you do in that situation. It is something that will hold him back for quite some time. Just not being able to get over that hurdle. As soon as he does it, which he will do, it's inevitable because he is so underwater with all of his life responsibilities that there's no way he can manage this.

As soon as he does it, he's gonna wish that he did it five years earlier because it's gonna free up so much of his time. This laundry list of things that he wants to get done that he doesn't have capacity to do will all of a sudden start getting done.

And he'll wonder why he waited so long. I think the answer is probably therapy. It's like how people get through that. But I don't see any other solution other than that. - Let's talk about a few other pain points. One for me was, I didn't think I had enough for someone to do.

And maybe this stems from, and we'll get to how you could actually execute this, hire an assistant, software, all these tools. But I had experimented with single task delegation where you hire a virtual assistant on the hourly or task basis. I had pretty poor experiences trying to do that because there's a certain relationship that needs to be built.

I now understand that. But early on, I was like, well, it's just, it's a lot of, I don't have enough to fill someone full-time, so do I need someone part-time? And it's so much work to ramp them up. It just felt like too much. And it felt like I didn't have enough work to justify it.

So I guess I have a bunch of questions. One, how do you think about that? And I have some thoughts, but also the common thing I hear people say is, well, once you do this, it'll free you up to spend your time on things that can probably add a lot more value, especially when people think, oh, it's gonna be expensive.

It's, well, once you have this time, maybe you can create value elsewhere, but that's so abstract. So I guess let's break it down and say, how do you think about the fact that people don't think they have enough to do? And then separately, we can talk about how do you think about the value of what you could do, but it's very nebulous.

- Yeah, so there's several different branches from that. I think one is that you probably have more things to do than you realize. I have a friend who very recently, finally went over the hurdle, got an EA and immediately saw the value. He's been fighting this for years. He finally got one.

And within about two months, he had three. And his major hurdle was, I just don't feel like I have enough stuff for an EA to do. And then he got one, freed up a ton of his time, got two more within a couple of months. And so part of it is you have to just take the plunge and see if there is enough work for somebody to do, especially if you're in a meaningful leadership role, there's almost always more stuff to do.

I think what helps is if you work with, typically it would be an agency of some kind that is specialized in this, where the EAs are trained to be more proactive. There's a few of them. The one that we work with is Athena. They have a training program to teach the EAs how to make you 10 times more productive.

That's their shtick. And so they are trained to be proactive in finding ways to help you extend your leverage. Whereas if you find one yourself, which is totally plausible and is probably less expensive, it's a lot more effort for you to have to learn how to interact with this person, how to train them onto your systems.

You have to teach them how to do things as opposed to the EA trying to pull and get more value from your time. So I think that's one aspect is having the right pairing, depending on your level of experience. If you're a highly experienced alligator, you can probably go with a less expensive option and you can do a lot of the training yourself.

Another branch of this, of the not having enough to do, is really try to lower the perceived risk of working with an EA. I was talking to my brother about this very recently, where I said, he has a lot of things he needs to delegate. And he said, you should just try hiring a person with this profile and just see how it goes.

And he's like, yeah, but it's gonna be X dollars per year, and then there's this, and then there's that. Imagine, try to frame this as like a two week experiment. And how much is that gonna cost you? And if it doesn't work in two weeks, all you've lost is like $5,000.

Working backwards, do you think it's worth a $5,000 experiment to see if you can delegate all of these parts of your life that you don't really wanna do? The answer is, well, yeah, obviously, it's worth it. But when you project out this, if you view it as a lifelong, fairly expensive commitment, the burden to get over that hump of, I should give this a shot, is just, it can be too high for some people.

So I think lowering that perceived risk threshold is another one. - And that's something that I think happens to us as humans in a lot of ways. I talk to people about, oh, I wanna quit my job. And they're like, well, I'm gonna lose out on my $100,000 a year forever.

And it's like, no, you're gonna lose out on your $100,000 a year until you do something else to replace it. So you could think of it as, if you think it'll take you three to six months, you're taking a 25 to $50,000 bet. And what's possible, and by the way, after tax, maybe it's half that if you live in California.

And so it just kind of changes that perspective. So I think that's a really helpful perspective. And I've told a lot of people that now that I've done this, I've been like, look, commit to, I say three months. I feel like two weeks might be short to really feel the value, though two weeks in, I felt the value.

But even at three months, it's a small, in my opinion, price to pay. And when it comes to what's the upside, it's like, well, you can get a sense of that in those three months. And then I'll just say to the previous thing you discussed about not having too much to do, my exercise I recommend people do is just for a week, just write down every task that you could delegate to someone who has built up enough context in your life.

And at the end of that week, you'll probably have a list that you're like, wow, maybe I do need to. - For sure, yeah, and it sacks up pretty quickly. As you flex that muscle, this is, as I mentioned, a friend who avoided this for a long time and now has three EAs.

Once you flex that muscle and you learn what types of things can be delegated, then you start to see opportunities all around you. It's something when you learn how to program for the first time, and then suddenly you discover all of these things that can be solved in software.

You realize that code can solve all kinds of automation problems. So what are some examples? For software or a delegation? - No, no, for the delegation. - I'll describe it maybe in the more abstract sense, which is people often assume that much more context is necessary than is actually necessary in order to delegate something.

So a recent example that I had is I have a CRM where I keep track of all of my friends and people that I want to stay in touch with. And we had a situation where the locations that people were tagged in were getting a little bit too specific.

Like, do I really want it to say Los Gatos, or do I want it to say Atherton or Bay Area? Because really, I don't need that level of specificity. It makes it much harder to figure out where people are. And so I just mentioned to my EA, 'cause I know that I can delegate this to them, where I said, "Anything that is not a major metro area, "find the nearest airport and assume "that that is the major metro area." 'Cause that's probably where I'll be flying into.

And so they were able to handle that whole task. And in the past, I probably would have said, "There's just too much context." You know, if they're in the Philippines, they don't know American geography, so I'm gonna have to go through all of these myself and fix this. But if you come up with ways where you realize, if I create these rules and these general heuristics, you can delegate it a lot better.

So once you learn what sorts of things don't require such specialized knowledge, and also when you lower that risk threshold of asking somebody to do something in parallel. Another recent delegation that I did was, I totally stole this idea from Wiz, one of our investors, where I thought it would be cool to make custom Magic the Gathering cards for everyone on our team.

And we have a company directory, we have a spotlight article, which has a bunch of background on them. And so I spent maybe 15 minutes doing some demos where I said, "All right, here's what I want you to do. "Go through each person in the company directory, "take their spotlight article, "feed it into chat GPT with a prompt like this "to get some sort of Magic the Gathering style, "like Ben is the marketing sorcerer, "and have some abilities and some cool stuff there.

"Feed his images into Mid Journey, "generate a really cool looking visual "using his actual face, "using the prompts that you just generated, "and then put that onto a Magic card "and then have that shipped." It took me 15 minutes to do that delegation, and it turned out super cool.

And I know enough about how to delegate that now, whereas five years ago, I probably would have said, "This is way too hard. "There's so many intricacies "of what needs to be done here. "I wouldn't know how to use the proper language "to delegate that effectively." So it just takes a lot of practice and you need to flex that muscle.

- So we're gonna come back to that language, but we have a veneer for both kind of work and personal, which I wanna get to that concept, but also hired through an agency. We use an agency called Oceans. Similarly, appreciate the training that I'm not doing, the managing I'm not doing, and that kind of stuff.

But we had started putting together a task list because when you start working with someone, you need something for them to do. And it was interesting because she's based in Sri Lanka, so her day started before we ever met. So she had about four hours of work before we ever met.

And I was like, "Oh, I can't wait to give context on this." And so we put something in Notion that was just like, we need to restain the wood in our backyard. And that was the prompt. And I was like, "I can't wait to give this person more context." And then we go to the first meeting and I was like, "Oh, they already found five people in our general area because they knew where we lived that can do patio staining 'cause you can search that." And they had already emailed them and said, "Hey, what do we need to do to get a quote?" And I was like, "Oh." - Exactly.

- Like I didn't realize how easy this was until I just wrote something. - I totally agree that you think you need more context than you need. I also wanna talk a little bit also about the language and all that. But let's talk briefly about finding this person. So agencies are an option.

You mentioned the one you use, I mentioned the one I use. We both seem to have great experiences there. You can hire these people yourselves. I agree, it usually comes at a lower cost, but the burden is more on you. No matter where you go, I assume you have to do some vetting.

You've hired more EAs than I. How do you think about that vetting, even though an agency might do some of it for you, you still wanna find someone that's a good fit for you. What have you learned in that process? - I would say we generally just set very high expectations for the agency.

I think a lot of the agencies, I've worked with others in the past, they'll give you a slate of candidates. I usually just tell them, "I'm not gonna do this. "So you tell me which of these is the best "for what I wanna do. "And if they don't work, then I'm gonna fire them." (laughing) So I'm putting this on you.

This is not a me decision. This is a you decision. When a friend of mine who was working at McKinsey for a partner, and he wrote up a whole slide deck, and the partner said, "All right, are you absolutely "confident that this is ready to ship?" He's like, "Well, let me double check." And he made some adjustments, he improved it.

He's like, "All right, are you now absolutely confident?" He's like, "I don't know. "Let me do a little bit more work." And he's like, "All right, are you absolutely confident "this is ready?" He's like, "Yes." And he didn't even look at it, he just shipped it. And he's like, "Look, we hired you "because this is what you do." If you work with an agency that you trust, and you let them do the vetting, they're gonna know a lot more about the stuff than you will.

The worst case scenario is you just have to rematch if you work with an agency. I would say, if you end up working with an individual, the best way to do it is probably through real work tasks. So coming up with a task of, it's almost like a scavenger hunt.

It's like, here are five tasks that I often do. Here's a loom explaining what I need you to do, and then just do it. And the times when I have had that done, it is remarkable how wrong some of them can be. And you just know immediately. I would say the most basic thing that you're looking for is ability to follow instructions.

It's like, what I want you to do is download this thing, look up these things, put it in this format, and then you just do none of those things. And you just end up with something completely different. It's like, okay, this is just not gonna work. So at the most basic, ability to follow instructions, if you're assessing a candidate, would probably be the biggest one.

I think the second order to that would be their ability to be proactive in finding new things. I would say, if they follow those instructions and they can come up with ways of saying, and I think it would actually be better if we also did these things, and maybe you hadn't thought of this as well, that's a really good sign, because it's lowering that burden that you have to think through the process.

Like, as recently as today, one of my EAs said, "Hey, I noticed I was doing this process for you, but it's not really getting a lot of engagement. I think we can probably kill this and fold it into this other process." It's like, "Oh yeah, I totally forgot that we were doing that.

I'm on board." And so that level of proactivity is a really important one as well. I'm sure many other things, but those are probably the two biggest ones I'd look for. - Those two were top of my list. And the third was just the ability to ask questions if uncertain.

And this, we'll get to kind of cultural challenges, but there are some people where you give a task and if they don't know how to do it, the kind of default answer is, "Well, let's just do it." And then in some people's, the default answer is, "Well, let me ask a clarifying question." And I think for me, once we built up that expectation, it's like, I'm not always gonna be perfect.

I'm not always gonna give you the context. But if you don't have it, just ask. Like, it's okay. It reminds me of, there are some cultures in Asia where you tell someone something and they'll just nod as if they understood, even if they didn't. It's like, that is not the best quality in an EA, at least for me.

Maybe this varies person to person. - Yeah, it's an interesting one 'cause I definitely hear the clarifying question thing. The nature of these clarifying questions, I've actually had to work with a few EAs who struggle with this, is try to make it so that your clarifying questions, I only have to answer yes or no to.

If your clarifying question puts more work onto me, it is a bad question. So I don't know if you've had this experience, but sometimes the clarifying question will be, you ask them for some basic task. And like, "Well, what about this? What if this happens? What about this? What about that?" It's like, "Oh God, I've just spent 10 minutes clarifying this." Versus, "It's unclear to me what this would be.

How I interpret this is it's probably this. Is this correct?" Yes. "I assume that what you mean by this is this other thing. Is that right?" Yes. And so always trying to get to a point where the resolution is just me saying yes or no, as opposed to putting the burden back onto me for the clarification, where I have to think through all the different implications of different tasks.

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How have you thought about working with people in different time zones, different cultures, versus in-person, versus remote, as kind of a few criteria when hiring someone? - I think it totally depends on the tasks that you need. So the earlier example I mentioned, my brother is looking for somebody to work with.

That would be in-person, because almost all of the things that he needs would need to be done by somebody who is in-person, near where he lives. And so thinking about what it is that you need people to do, in my case, most of what I need, in fact, basically all of what I need, are background accountability-related tasks.

Just keeping the lights on, keeping the wheels turning, making sure that I have clear visibility and reporting on everything that's happening in the business. And so that doesn't really need to be co-located. It also really doesn't need to be in the same time zone. I found that if you have no overlap on time zone, it can be pretty rough.

Levels is a remote-first company, but we still say the default time zone expectation is America's, which is basically California to Brazil. If you live in the Philippines, if you live in India, wherever you live, you need to be available for at least that part of the day. We don't have a lot of meetings, so it turns out not to be particularly onerous, but if we're gonna schedule a meeting, the entire team is not gonna orient around, I guess we need to take this at two in the morning to match the schedule of the person who's not in this time zone.

Otherwise, you end up running three different companies, and it's really, really tough. There was a founder of a fairly large, fully remote company that I asked, "Do you have any regrets, "things that you cannot undo at this point?" And his biggest regret was not setting time zone expectations. He said, "We basically have three "fully independent companies, "and coordinating between them is a nightmare." He said, "If I could do it again, "I would just say, you can live wherever you want, "but America's is the time zone, "and you have to adapt to that." - I talked to a few companies when we hired REA.

We went with Oceans. I didn't realize that some of the decisions they made were just by default making them because they knew they were better, and so I didn't know what I was missing had I gone somewhere else. But for example, they asked me two or three intakes, and then said, "We think this person is the best for you." I never even had to think about it, which was wonderful.

- That's awesome. - I didn't realize what I could have had to do. And then the other one was they said, "We think asynchronous and synchronous communication "can work together, "so we are going to have your assistant work "from 8 a.m. to 1 p.m. Pacific "with three more hours asynchronous "while you're not working." And I was like, "That sounds good." I didn't realize the benefit at the beginning, but it is actually very helpful to have someone working when you're not working.

So you're signing off at the end of the day, and you can say, "Here's a few things "that need to get done," and they're done when you wake up in the morning. - Totally. - And I didn't realize the benefit of that. - Yeah, I found it especially useful 'cause I have almost exactly the same time zone overlap in terms of when we're live and when we're not.

And the advantage of rescheduling things in the morning or canceling meetings or anything that would need to happen that would impact my day that they can see before I'm even awake so that it's not a last-minute scramble, it's already handled by the time I wake up, which is super handy for sure.

- One other thing you didn't mention that I thought was worth for some people hearing is if you choose to go the route of hiring this person yourself, you might save 50, 60%. There are companies that will help you find that person, like a headhunter agency. I think one of them's called Shepard, and they'll help you.

There is this weird emotional burden of you are now the employer of record. And you mentioned rematching. If something doesn't work out, just ask yourself the question of, how good are you going to be at rematching knowing that you are gonna result in someone losing their job? If you work with an agency and you rematch, they'll find another person for that or another client for that EA.

So I think that's something that, for me, it's not that I couldn't let someone go. I've done that in the past and it's never fun, but I know that I'm paying a premium to have a lot of the overhead removed. And I just think, especially for someone who's trying this out for the first time, like I was, it has been the right decision for me.

And I'm someone who loves to save money. - For sure. The opportunity cost is real. People often evaluate opportunity cost as $0, but it's not. It's very much not $0. - Yeah, the things that I have now been able to do, both in terms of free time and just other work projects that have actually generated revenue is really incredible.

One of the reasons that's possible is that our EA works both on personal stuff, family stuff, and work stuff. Have you seen that to be successful? I know you've had multiple EAs and I asked myself, should I have done this separately and had two and split their work or had them be part-time?

How do you think about that house, personal version of an EA and work version? - So I haven't done much of the house stuff, but certainly the work and personal. Part of it is for a lot of people, like for me, there's no line between what is work and what is not work.

Like if I have a personal task that I'm going to do, it means I'm just going to be doing less work because otherwise I'm just gonna be working. There's no line of I only work X number of hours. Any minute that I'm spending doing personal things is a minute that is detracting from work that I would be doing.

So that might change once we have kids, which is imminent, but it will definitely change. - Well, the kids will be a personal thing you're doing and you'll say, I want to spend time with my child and I'm not able to work for it, which will actually make the value of all of this just so much higher because inherently you will lose time.

And not only will you lose time 'cause you might just not sleep a lot, there's a lot of reasons you might lose time, but you will want to do other things. And the fact that we had two children and I want to spend time with them doesn't mean that there's less work.

Like nothing magically changes. So you need to get better at this. - We have some memos internally on how to think about this. We encourage people on our team to hand off more of their personal lives or more of their personal tasks to their EAs, even though the EAs are paid for by work.

But it really depends a lot on what the task is and who the person is and what their intent is. So a recent example, one of our executives was really underwater on selling a house, doing taxes, like keeping up with all of these things in their personal life. That was just, it was really a lot in addition to all of their work responsibilities.

We made it super clear, you can absolutely use your EA to help you do those things and really lowered that cognitive load of managing those things. But there is a line and it's fuzzy. It's admittedly a fuzzy line. A really obvious crossing that line is you use your work EA to run your side business to that is revenue generating or has some personal benefit that is unrelated to the business.

You can always rationalize these things. So like, well, if I didn't have my EA doing it, then I would be working on that instead of doing level stuff. But if you're making money on a product and you have costs of labor associated with that, levels should not be paying for it.

You should just have your own team doing that. Everything in the middle is a little bit fuzzy and you just kind of have to use your judgment of is doing this thing, is this in the best interest of the company? Is it the case that you delegating this part of your personal life to an EA?

Is that going to benefit the company? Are we going to have better output from you because of that? And if the answer is yes, do it. If not, don't do it. If you ever have questions, you can always just ask somebody. It's good to socialize these things. Like if you think it's reasonable and you ask somebody and they recoil, it's probably a bad sign and you probably shouldn't do that.

But yeah, just asking around is usually a good way of getting feedback on whether it's appropriate or not. - And if you're someone who's working on your own or just hiring an EA to help you, then it doesn't matter. - It doesn't matter at all. - I'm not actually sure how companies would feel that don't provide EAs to someone hiring their own EA to help scale them at work.

I'm going to throw that into the ether unless you have opinions, but on the personal side, I've talked to a lot of people about our experience, many of whom are a little bit later, have some kids, both adults working, and the value of just having an EA for completely non-work stuff is enough to have someone full-time.

And for costs, for people who are just like, "Wait, wait, wait, how much is this?" I would say, I have not heard of anyone finding an EA directly on their own, fully loaded for less than $1,000 a month. And maybe there's some edge cases. I have not heard of anyone spending more than four or $5,000 a month for someone remote.

And then in person, you could spend $10,000, $15,000. So just for people who have some rough sense of that, I would say for somewhere in the order of, let's call it 20 to $40,000 a year, you could probably find a very talented person somewhere outside of the United States to give you a lot of leverage.

And in our personal life, there are just so many examples of things that I think always sit on that kind of mental burden. So it's like, "Oh, we're gonna go on a trip." As soon as you book a trip, there's like a checklist. You'll learn this. It's like, "Okay, well now we have to notify the dog walker that the dog needs to go somewhere.

Now we need to notify the school that a kid's not gonna be there. And we need to notify the swimming class that that's not gonna happen. And we need to make sure, just double check that our passports haven't expired or are going to expire within six months." Because if anyone doesn't know, there are a lot of countries that even if your passport is valid, won't let you in unless it's six months out.

And so you could almost create this checklist of every time we book a trip and then be like, "Well, this is what we need to do." Or it seems like something crazy to have someone overseas do, but research five healthy meals and order the ingredients for them on Instacart or Amazon Fresh and put the recipes in an app so that we can see them as a meal plan and cook them.

Like that is a thing someone anywhere in the world can do. And the worst case is you might get a meal that's not the exact thing you would have picked yourself, but you spent no time planning it. That was one where we started doing it. And then we experimented with a meal kit company called Green Chef.

And it's just been like, "Oh, this is great." Sometimes we forget to pick the meals and we're like, "Oh, we didn't pick it, but we didn't have to think about it." And so in our personal lives, there've just been like these countless research this, help figure this out, help plan this, find someone to stain the patio furniture, call Delta because our flight was five hours late.

And I know that we need to get some compensation for this, or we need to change this thing. All of those have made it tremendously valuable. I did an episode with Dan Martell who wrote this book called "Buy Back Your Time." And he has a house manager, much like your friend would need.

- I'm gonna write it down. - It's focused a little bit more on business than personal, but he is a expert delegator, which I have a couple of questions about things he does if your experience there matches. But he has someone doing all these things. He wants someone to go pick up dry cleaning.

Obviously, that's something you'd need someone local, but it just opened my mind to the fact that even if you don't have enough work or side hustle projects, you might have enough personal projects. And the freeing up of your personal time might unlock you to start that side hustle project, to start that business, to just spend more time with your kids.

Like there are things that might be not revenue generating, but life fulfilling that all could make this super valuable, even if it has nothing to do with work. And so in our case, it spreads the line of both, but almost has shown so productive, like, "Well, maybe we need to, maybe we want to, "and then how would we split them and how would we do that?" That's a whole other topic, but I don't know.

It's seeing what it could unlock for someone outside of work is powerful. - And it's funny, the idea of, say, getting an EA to help you with work stuff, even if your work isn't paying for it, if it's $20,000 a year and you have a really meaningful salary, it could accelerate you quite a lot in terms of your productivity, and you'd really stand out in terms of where your peers are 'cause you get so much more done.

But it does remind me of something from The Onion several years ago where there's a guy who had basically done exactly this and he outsourced his job to somebody in Minnesota. Then they interviewed that person and he had outsourced it to somebody in the Philippines, and that person had outsourced it to somebody in Pakistan.

The conclusion was 60% of the world's tasks are delegated to one guy in Pakistan. (both laughing) You can definitely get a lot of leverage out of it, for sure. - Yeah, I would say, depending on the type of tasks, I would highly encourage someone to vet this with their employer before handing over their company's credentials or anything like that.

- Most companies would not be cool with that. - Yes, but I could see a world where if you were in sales, which, as you mentioned earlier, you wouldn't be, it could be a place where you could say, "Hey, could I hire someone on my own dime "to help me source leads, to help me cold call," that kind of stuff.

Maybe you get the company to do it, but if not, I could see, especially for people on commission, with the approval of their employer, it could very seriously pay for itself quickly. But we just talked about credentials. You talked about an EA helping with taxes. One of the things that I think a lot of people are hesitant with hiring someone they don't know overseas is how much do you give access to?

You're giving access to your email, or your logins, or your bank account, or in the case of my friend Dan, he actually has his EA on his iMessage, so all of his text messages, everything. How do you think about that kind of access, control, and trust? - You wanna have as few people with access as is necessary to do whatever tasks you wanna do effectively.

It is a security vulnerability. Any person who has access to it is a security risk, and so you have to be very mindful of that. You want it to be as few people as humanly possible. What you give them access to, it's really gonna be a matter of your own personal risk.

And some of this also comes down to, there's a lot more recourse when you have, say, an agency, they vet people. Somebody from one of the agencies we've talked about, it's unlikely that that person is going to copy all of your information and dox you. But if it's just some random internet troll that you don't realize that you've hired, you're not gonna be able to find this person.

You have no recourse if they do something that's inappropriate. So that's one of the other risks you have to manage. I don't have a car. I generally just take Uber. I think people often underappreciate how much liability you take on just from driving. It's a very real thing, and you don't have that liability when you're in an Uber.

And so pricing in, liability risk, insurance risk, the cost of the car, depreciation, gasoline, Uber's not as expensive as people think it is. When you calculate all these different forms of exposure that you have, it's very real. So personally, I do give access to a lot of these things, and I give it to as few people as necessary to be able to get a task done effectively.

And I know people who are loathe to give access to basically anything for exactly the same reason. It's just, it's too risky. - I will say a few things I've picked up in giving access. So I think most people listening will have a password manager. And so, you know, that's one way to share access to things.

You could potentially give someone access to an account, but not give them access to the two-factor code. So you know when they're logging in, that's something. I separate email addresses for banking and things where someone could spend money, or in my case, points. Like, let's leave that separate. And so that's one way that I've said, okay, you can have access to my email, but if you needed to, I don't know, send a wire transfer, the confirmation is not gonna come through there.

I know plenty of people that I've talked to separate their phones, so they have two factors coming into one number, and they have regular things coming to another. So you could potentially give someone access to your text messages without giving them access to some of the controls they would need.

Also, there are a lot of financial institutions that actually have access controls. So like, I think in Chase, there are probably plenty of people who have bad experience with Chase. You could actually say like, oh, can I add a person? Can I delegate information and give them only these rules?

Most business accounts already have this built in, but a lot of personal accounts don't. But when you can find one that does, that can be helpful. And a lot of times, you can ask. I remember someone I know just asked if they could have a Wells Fargo business account, but for themselves, because it had all these rules and these tools, but it was like a much worse login, terrible app, but they could set up these kind of procedures.

So that's some of the things I've thought about. You know, with credit cards, I hear someone, oh, they could spend all my money. It's like, well, you also have liability and fraud protection. You can add an authorized user and set a credit limit. So I think there are ways to mitigate some of these things, but also every time you get on the highway, there is some risk that something like, I also have to weigh the risks of being able to have a life where I'm spending time doing what I want.

And sometimes that risk is just worth it. - It's a risk calculation. People in general have a very hard time assessing risk because status quo bias is so strong. Whatever you're used to doing, and you've never experienced some catastrophically bad outcome from normal day to, people really underestimate how dangerous driving is.

It's super dangerous, but we do it all the time. And when you think about it in the abstract sense of like, yeah, we're just going to be whizzing by these multi-ton vehicles going at 70 miles an hour past each other with like people with very little experience driving while texting, you would say that should be illegal.

There's no way that that is allowed. And that's what we do all the time. It's remarkable that it is as safe as it is. And so every day you're making risk calculations. You probably didn't check this morning whether somebody cut your brakes. If that did, that would probably be really bad, but you probably didn't check that.

But if you did, it would decrease your risk that your brakes don't work. Did you check that all of these other aspects of your car are functioning normally every day? Probably not. And that's okay. That's a risk that you take, and it's probably a reasonable one. And so whatever that threshold is going to be for you, you just have to figure out what you're comfortable with and go with that.

- But I will say, even if you don't give up managing your finances to an assistant, there are still a lot of things that you could do to unlock stuff. And for some inspiration, I actually, Athena has these playbooks that I thought are really interesting on their website. I'll link to them in the show notes where it's just like ideas of things an EA could do.

On the personal side, I have a friend who, you know, uses it to be a better gift giver. He's like, I want to track people's birthdays and I want to give better gifts. And I want to make sure I'm more thoughtful sporadically and spontaneously. It's like, it unlocks not just things that they are doing that they don't want to do, but it unlocks things that they wish they could do and can't do now.

I don't know if there's things in your life where you've been able to do more that you never were doing before because of it. - Yeah, for sure. It's less that they are things that I can't do myself. It's more, I would not have been able to prioritize it because I would not have had capacity.

Like the magic card example that I gave. There was no universe where I could justify spending three days of dedicated time to making custom magic cards for everyone on the team. It just makes no sense. But I could justify 15 minutes on the instructions for it. And the team really liked them.

And so there's a lot of those sorts of things where I can't justify doing these things consistently. Like another one, oftentimes when a friend has a baby, I'll send them flowers, which is like a nice gesture. And can I justify myself or all of my friends figuring out what their address is, what the local florist is, what kind of flowers we should get?

I would probably have to spend 100 hours a year on this task. And it's just, I can't justify that. But if I can lower that threshold to 30 minutes a year, yeah, totally worth doing. So that's what I mean when I talk about getting leverage is that you're able to get leverage and you're able to do a lot more of the kinds of things that you really like to do, but it's just hard to justify relative to other priorities.

- Let's go a little deeper on how you onboard people to these things. So you say 30 minutes, 15 minutes here, you gave the example earlier in how you could spend time delegating the magic, the gathering task. What things do you do, tools do you use to make onboarding an EA or anyone that's helping you on your team for that matter, more effective at doing them?

- So the biggest tool is Loom, which is a screen recording tool. And it allows you to capture what it is that is on your screen. It allows you to capture it on content as well. This is one of the struggles of where people delegate in a more traditional sense, which is you have a phone call or you do it on a Zoom call, and then they're taking notes furiously while you're explaining the tasks to them.

And as soon as you end the call, they have forgotten what it is that you told them. The nice thing about Loom is you can record it async on your own time, you can send it to them, they can watch it at 2X, they can watch it again, they can pause it, they can take notes, they can come back to it a week later, and they can refresh on what the task was.

So solving this in content is really the best way to go about it. Other tools, I would say Voice Notes is a really good tool. I often use Signal, they have a good Voice Note tool. The Athena app actually is pretty good. Have you seen that one at all?

- I have not. - It's pretty cool. You don't even need to use Athena for it. My brother actually uses it for an unrelated use case, but it's a cool thing where you open it up and then it immediately starts recording a Voice Note. And you set it up where once you finish recording the Voice Note, it emails it to whoever you specify.

And so if you have an EA, if it's people that you know, however you wanna delegate these things, you just record a Voice Note and then you press Done, and then it just sends it to that email address. It's a very, very simple tool. - I've heard Whisper Notes or Whisper Memos is another very good tool for that same use case, but layering in transcription and a little bit of AI.

I haven't used it, but I know a few people that swear by it as the tool for that purpose. - Yeah, totally. There's a few similar tools like that. Voice Notes are really helpful because the friction of pulling out your phone, writing it out with your thumbs, I have just found is usually too high to get the task out of my head.

And by the time I've opened my phone, I've opened up my email and I've started typing, I've already forgotten what it is I wanted to delegate. If I can just open up my phone and say, "Hey, remember to send that thing to that person." Or, "Hey, I just had a meeting with this person.

Please make sure to follow up with these three people so that they know that that meeting happened and this was the outcome." And then I'm done. I'm convinced that the thoughts that we have are ephemeral. When you write out your ideas, that is the externalization of those thoughts. And those thoughts have now left your brain.

They're now in this artifact. And so the sooner you can get in these fleeting moments of inspiration, the faster you can get them out of your head and into some artifact that can be action, the better. - One other tool that has been really interesting to play with, I don't know if you've used the ChatGPT app with voice.

- No, I haven't. - So you can open up the ChatGPT app now and you can say, "Hey, I'm trying to prep an interview guide about delegation." And it feels like a conversation where the other person is lagging behind you three seconds 'cause it has to think. But I experimented with actually prepping an interview in a voice conversation.

And my only criticism is that you have to instruct it not to give you too much feedback until the end maybe, because they might say, "Oh, here's the guide again," and read through it all and then read through it all. But it synchronizes everything with the GPT website and app.

So you go get the text of it later, but you can actually have a conversation. And I wish I knew the name for whatever, I don't know, phenomenon, psychological principle, something is, but it is sometimes much easier for many people to get something out in a conversation than writing.

Not just the friction and the time, but you actually sometimes get a higher quality product. And so I find that when I'm trying to struggle to think about things, my wife and I all brainstorm an idea together and I'm like, "Wow, I got a lot more out of that." And sometimes she's like, "I didn't even say anything.

I just sat here and you talking to me," similar to kind of rubber duck debugging. It's like just having a person to talk to and audibly bring it out loud can generate something. And so yes, you can record yourself, but I encourage people to check out GPT Voice 'cause you can have that conversation and get feedback.

You can do it in your AirPods. It's almost like a little AI assistant that you have to trigger with the app. - Cool, yeah, I have it on my phone. I just haven't used that. I'll check that out. - You definitely said Loom was important, but I wanna make sure we give it a little bit more emphasis 'cause I've started using it for almost everything.

And it basically, anytime I'm doing a task, I just record it, at least the first time. And so even if I'm not sure I wanna delegate it, I'll be like, "Oh, I'm gonna go set up a new invoice. Let me just record it and I'll go put it in a repository of all the things I do.

Oh, I'm gonna book a flight. Let's record how I search for flights." I don't like to delegate my travel. I think you don't either, but at least there is a video. If I ever wanted to tell someone how I book a flight, I can walk them through the process of how I think about it.

There's no cost. As a early Loom user, I assumed every video had to have me talking with the video and the audio. You can just make a video of you just working. A part of me is like, "Should I just record my whole day?" So that I could, you know, there's an app called Rewind that records your screen all day, records your audio all day, and you can actually go back and search through it.

And it's super interesting for cases of like, "Oh, I was doing this thing. What was it?" And it OCRs everything so you can go search. Not the same use case. And I don't think it's as easy to go back and clip a thing, but it's kind of this idea of like always on.

So I would just encourage everyone, if you haven't used Loom and you have any tasks you wanna share to use it, but also I use it to push back on synchronous meetings. And I wanna take a little tangent here 'cause you've thought about this deeply. I don't think, and I know you don't either, that having a synchronous meeting, and for anyone who's unfamiliar, just like both people are in the meeting at the same time, whether it's a phone call or a video, is really necessary all the time.

- I think it's unnecessary most of the time, yeah. There are definitely use cases where it's really valuable and it is the best. Like we can't do this podcast asynchronously. It wouldn't make any sense. But some of the things that I found that are really useful is when somebody sends a meeting request, I will often send them a Loom in response and say, "Yeah, here's the answers to your questions." And it might take four minutes.

And they say, "Oh, okay, great. "Thank you." It took me four minutes. They probably watched it at 2X. That whole cycle took six minutes as opposed to some scheduled time in the future, 30 minutes of each of our time, where we may not have even delivered on what we wanted to anyway.

So you can skip all the small talk of the conversation and you can just get straight to the point. So proactively sending Looms, I have found has reduced the number of meetings that I need to take by, I don't know, 80%. Just 'cause a lot of times you just don't need to have a call to get basic information that people are asking for.

- And the precursor to that sometimes for me is clarifying that there's actually a purpose. I get a message from someone, it's like, "Oh, we're in this WhatsApp group together. "Would love to connect." And I might write back and say, "Hey, the next two months are crazy. "Like right now I'm on a mission to get 12 episodes ahead "just so that it feels like there could be a break.

"So the next two months are crazy." If there's something you actually want to discuss, feel free to send it over. I'm happy to record a response or feel free to use Loom and make a Loom and we can have a conversation. Especially with kids, there's a lot of times where they're asleep, I'm trying to be quiet.

It's midnight, but I could be responsive. And I find that does two things. Two things positive and one thing negative. Sometimes there are interesting conversations that probably wouldn't happen because the other person didn't really have an agenda but wanted to just connect. Many times that would have been a waste of time.

Sometimes it's not, and we should talk about that. But I do think that oftentimes it reduces meetings that are not necessary. Like someone we just didn't need to meet. It raises the burden for someone to actually have a conversation, but not in a way that says no. So if I get an email, it's like, "I'm too busy to meet." It's like, "Oh, that kind of feels bad." But it's like, "I'm too busy to meet synchronously." But if you want to record a video, I will get back to you.

So it just kind of makes the whole process easier. I don't know, for me. But I do hate that sometimes I'm missing out. - What I have found is that connecting on Zoom is soul crushing. And so I don't do it, generally speaking. If somebody says like, "Hey, do you want to jump on a 30 minute call?" The answer is almost always going to be no, unless there's a specific agenda of what we will discuss.

I have a much lower bar for meeting somebody for coffee in person. Because even if there isn't a clear agenda, it's much more energizing to just be in person and talking to people. Part of this is also I utterly lack discipline and the ability to wake up at a reasonable hour.

And so I often will schedule 8 a.m. coffees just to force myself to wake up at 7.30. Because otherwise I'll wake up at 10 or 11. And so that's a really helpful strategy to just get me out of bed in the morning. - Having children will also help. - Yeah, for sure.

Yeah, my friends who have kids, they seem to wake up at four or five in the morning now. One interesting thing is that I now delegate a lot more of my travel than I did before. It used to be the case that there was too much nuance in my travel schedule that I've tried delegating and I didn't have much luck.

But now that none of the airlines have cancellation and change fees, it is a much lower burden to effectively semi-automate the process. My entire travel schedule is fixed three months in advance, generally speaking. And so my EAs will see my travel schedule and they will proactively book flights. But they don't necessarily need to be the flights that I will take.

So I can see three months out or two months out, oh, they booked the wrong flight and then I could just change it. It's not a big deal. But at this point, 80% of the time, it's the correct flight and it's not a huge burden to change it. So I would say that I have semi-automated my travel because they can see my schedule, they can book the flights proactively and then I can just change it as necessary.

So I found that to be very helpful. - I know Sam and I have covered so much on the topic of assistance, but I've gotten so much value in my work and even my life from just having an amazing EA. Thank you, Pasini, if you're listening, you are awesome.

And I really hope that any of you who end up hiring one yourself have an amazing experience too. As I mentioned, I found my EA through a company called Oceans and not only have they been awesome to work with on that front, they also spent a bunch of time with me the last few weeks to help me put together a very comprehensive 13-page guide that lays out 10 tactical steps you need to take before, during and after hiring your assistant to really create a paradigm shift in the way you work.

It includes so much of what I've learned this year, some anecdotes and some tips, as well as everything they've learned running a business in the space for the past few years too. It's totally free, so if you wanna give it a read, just go to allthehacks.com/delegate or find the link in the show notes.

And if you wanna find yourself an amazing EA with Oceans, you can head on over to oceansxyz.com. And big thank you to Ian, their CEO, for offering anyone who signs up and mentions All the Hacks $1,000 off their first month. Definitely check both of those out. It seems like with every business, you get to a certain size and the cracks start to emerge.

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That's allthehacks.com/netsuite to get your own KPI checklist. Allthehacks.com/netsuite, N-E-T-S-U-I-T-E. I think if you apply the Pareto principle, like the 80/20 to a lot of things, especially in the world of optimization, I've found that you get to separate the decision from the optimal outcome and unopt outcome. So it's like, well, the example I've used a lot is I had an insurance policy for our home, and then we realized the home had appreciated.

It was like, we need more coverage. I also would like to have the cheapest policy. And so I mixed those two things together and said, well, let's go find the best policy. Now, this happened again later in life, and it was like, let's get a policy that covers the house at the right amount.

And then I can decide whether I want to go through the process of optimizing to save a little bit more. So in your case, it's like, let's book a flight. And then I can decide if it's worth trying to drill in and find the best thing or just take the one that's booked.

And so I've tried to get a lot better at, let's just do the easy 80% of the thing I want, and then separate the decision to optimize from the decision to do the first part. Oftentimes, you can delegate that, like the hard part that you maybe feel uncomfortable delegating is that last 20%.

- Yeah, and the reason why I wasn't able to delegate travel as effectively before is that it used to be the case that in every airline except Southwest, if you book a flight, you're like signing a suicide pact. You cannot cancel this flight or they will charge you $150, like plus a bunch of other fees.

Now there's no change fees, no cancellation fees, no anything, and so the risk of booking a wrong flight is much lower. - Yeah, it's like you might get some credit. - Yeah, which I'm gonna use anyway. - Unless you're booking something obscurely international, where you probably wanna get it right because a Kenya Airways credit might not be that useful to you in the future.

Okay, so when it comes to meetings, you've talked about using Looms as a way to reduce the meetings you have, but I also know that having more relationships, meeting more people is something you're interested in. Yes, you can meet them in person, but how do you think about that entire project of building relationships, networking?

I know you've said you kind of default more of an introverted person. You say you don't wanna be in sales, you'd rather be an engineer. How do you think about building your network and taking meetings that might be a waste of time, but could turn into really powerful connections?

- It's something that really came from the recognition that so many of the good things in my life have just come from people that are around me. And very rarely is it actually something that I did. I put more emphasis on being around people that I care about. There's a lot of spontaneity in these meetings.

There are often people that I don't know very much about, and I meet with them. They're usually friends of friends. There's a, I forget who has this quote, but I think it's a really, it's a useful mindset to come into every conversation, including every conversation with your Uber driver, which is, "Every man is my superior in some way." Some variant of that quote.

It has always surprised me how there were life experiences from people. There are ideas that people have that are really fascinating and often different than your own worldview. And so figuring out how to learn from other people in any context, I think it's just, it's a skill to develop.

And once you get good at it and you really are excited to talk to people and learn from them, it's really energizing. So I appreciate that aspect of meeting new people. I would say I rarely come in with a specific agenda. It's like something that I want out of a person, but it is surprising how often unexpected value comes from these things.

I would say that I'm convinced that the universe is conspiring in my favor. It's just, these things happen in a way that it just seems much too improbable to be random. - And you said, once you get good at it, what does that look like? You're meeting with a random person you don't know.

What do you do now differently than you would have done before? - So I think some of it is you, who was it that I was talking to? He had a good way of describing it. He says he really doesn't like beige conversations. (laughs) Which is just like, yeah, weather is good.

Food, I eat food too, food and weather. And you just kinda, you spend 10 minutes just sort of talking about beige things. And the sooner you can get to a point of asking a more interesting question. The biggest thing is, I think this was in How to Win Friends and Influence People, where he says, it's really important to remember people's names.

The most important trick to doing that, to remembering people's names, is first you have to want to remember their names. (laughs) That's the secret, is you actually have to want to do it. If you don't want to do it, you're not gonna do it. And so I think that's a big part of it, is you have to want to find something interesting in these other people.

If you're just going through the motions, it's not gonna be fun. And so if you learn about somebody's background, where they're from, what they're struggling with, if they have any regrets in their life, what they're excited about, and just the sooner you can get past that initial point of just sort of a conversation that you could place in with any random person in the world, and it would be exactly the same, the sooner you can really start to get value from those and find them a lot more energizing.

- I mean, I guess maybe one of the tactics would be this gratitude exercise you did to find them. - The gratitude exercise that I did, this was several years ago now, I spent some time reflecting. It was in one of these books that I read, they recommended doing an exercise like this, and just writing down all of the good things that have happened to me in my life.

And well, I think I maybe listed a hundred things. And what was so interesting when I was reflecting on this list was how almost all of them were because of people in my life and not because of something that I did. And that was a real wake-up call to realize that a lot of these great things and the people that were impactful on my life in both personal and professional things, they sort of fallen off the radar, and not for good reasons, just 'cause I kind of forgot.

And the nice thing about computers is that they don't forget things. And so where I think a lot of people go wrong, I've tried building a personal CRM product maybe five or six times, and it's very hard. I'm pretty confident that it's not a category that will ever work.

The main reason is when I talk to people about it, what they expect a personal CRM to do is automate all of their personal relationships. And that's not what a personal CRM does. It really just obliges you to spend a lot more time managing your personal relationships. Instead of spending one hour per week, now you're spending 10 hours or 20 hours a week.

But you get a lot more value from it, and it's much more impactful. So I spend an inordinate amount of my time just maintaining these relationships, and talking to people, and trying to see how I can help others. But it definitely takes a lot of time. There's no way to automate it.

- Is there a tool you're using to keep track of it all? You mentioned kind of the renaming of locations earlier. - So honestly, I just use Airtable at this point. There was a really interesting article, forget where it was from, but it was with Peter Boyce from, he's a venture capitalist.

And what was interesting was how, I think it's called Peter Boyce is a People Person, I think is the name of the article. What was interesting is how convergent our CRMs ended up being. He ended up building his own. They're 90% the same. And so there's only a very limited subset of information that's actually useful.

Human brains are pretty good at networked thought. I do think that almost all of this stuff will eventually be solved by some of these new AI tools, because they're much better at contextual networked thought in a way that existing tools have not been. But having lists of people and lists of groups of people, all of my friends who play board games in San Francisco, I have that list.

Location, San Francisco, tag with board games. And I just have subsets of people that I want to stay in touch with on some regular basis, people that I meet up with for coffee. And you just have these lists of people and their interests and their locations. And it's really not much more complicated than that.

And it's just the practice of every Sunday I have a calendar block to just look through the list. That's the whole process. I just look at all the names and I go, oh, Nick. I haven't talked to Nick in a long time. I should send him a note. And then I give him a call.

We catch up. Or it's like, oh, Anthony, yeah. Man, I haven't seen him in like two years. I wonder, is he still in Miami? I'm going to check in. And he's like, oh, just moved to San Francisco. We should get coffee sometime. Cool. It's a real event that happened.

We're meeting for coffee soon. So just learning that practice of just looking through the names, your brain is much better at coming up with connections of other people, things that you're working on, and how it relates to those people than the computer will be, at least with current technology.

So I have a similar list, which I didn't even think of as a personal CRM, which is just I have a subset of my contacts on my phone. And it's called walking calls. And it's basically like if I'm driving or walking, who are all the people that I want to regularly connect with?

And I'll go in and scroll through them. What it doesn't do a good job of-- and there was an app back in the day called eTax, which actually, I think it was Howie Liu who might-- I would have to look it up. But there's a small chance that the person who actually started this company went on to start Airtable.

I'm going to look this up after. But the cool thing it would do was it would sync with your email, and it would sync with your AT&T login, because pre-iMessage, all of your texts were routed through the carrier. And it wouldn't know what's in the text, but it would just know when you last emailed or texted or called this person.

And the one thing that I want a CRM to do well-- and maybe you have an EA do this-- is just I want to find the people that I had let go. And I don't know how many people are in your list, but I imagine it's not 10. Do you have a way to sort it by when you last talked to them?

And is it too much burden to keep that date up to date? It is too much burden to keep that up to date unless it's an automated tool. I had actually, in some of the previous versions of CRMs, I had actually figured out a way to do a lot of those things.

So very tactically, the iMessage on your desktop is just like an unencrypted SQLite database that you can hack into and get all that data. So you can have a script that just figures out when you contacted these people, syncs it with your CRM, and what data you have on them there.

Google Calendar has an API. When you create an event, when you cancel an event, whatever you do, there's webhooks that you can tie into. So you can then see, oh, I had a calendar event with this person, and that shows up. There's a lot of ways that you can do this stuff.

But the reality is just I didn't really-- I didn't use it. It was a lot of work, and it just didn't add a lot of value. But these are totally achievable things if somebody wanted to build it. And one thing that I've heard you talk about before, which changed my perspective on, I don't know, random meetings, was I think my default assumption was, well, if I'm going to prioritize meeting someone, let's prioritize someone who we have a lot of mutual friends with.

Seemed like it made sense. And then I heard you talk about why the opposite might actually be more beneficial. So the have a lot of mutual friends with, there's a term called network homophily, which is how similar are all the people in your network. And I don't want to say network homophily is a bad thing, but it definitely has trade-offs.

And you limit your exposure, and you end up in a dense network. There's a concept called eigenvector centrality, which is really this idea of it's not just how many people do you know, but it's the second and third order effect of how many people do each of them know.

If you're connected to all of these super connected people in each of these dense networks, you are a much more connected person. You will likely be able to deliver a lot more value in your life. You can use the network connectivity as maybe a proxy for potential quality of the conversation.

But I think there are a lot of other ways to try to inject that diversity into it. In New York, I used to host these dinners. Hopefully, I'll start doing these again in San Francisco, called second degree dinners. Have you ever heard of this format? It's pretty fun. The idea is you start with, let's say you want to end up with 12 people.

So you start with a core group of four people. And each of you invites somebody that you are confident nobody else knows. And then you ask that person to invite somebody that they think nobody else in the group will know. And so you end up with 12 people, most of whom don't know each other.

But everyone whom knows one person. That's right. But everyone knows one person. That's right. And so it is almost necessarily going to be a much more diverse and interesting group of people than you would ordinarily have at a dinner party. Which would be your seven best friends. It would be exactly.

It's your seven best friends. I host a lot of different types of dinners for these sorts of things. And each of them has their own intent. And that one is more like-- it is rare that you would host some sort of event where you have a sculptor, a stand-up comedian, an investment banker.

You just have this completely random eclectic mix of people that would otherwise not have interacted. And those can be a lot of fun. I hope to maybe-- well, I guess maybe I know too many people. I know too many people to get the invite. Though I do fall in this new subset of once you have children, you're like, well, now I need people who are willing to go to dinner at 530.

Or at 9. When the kids are asleep. But I want to circle back. We spent a little bit of time on some tools. We talked about using voice delegation. I think you and I share-- maybe passion is the right word. I'm not sure. But for optimal communication and productivity and tools and everything, let's talk about some of the other tools you use to organize information, access it quickly, and spend less time on things that you don't want to spend more time on.

Yeah, so Notion is a really good tool for keeping track of documentation internally. You probably know this because I imagine you are pretty deep into Notion. But there's the very simple version of there's a page, it's a wiki. And then there's the advanced version of Notion with databases, linking.

You have all of this. Notion is a really flexible, very advanced tool. If you go deep into the inner workings of Notion, there is a lot more functionality in Notion than most people realize. They recently added automation, which I found for the podcast. Every time I source a new deal, a favorite, a tweet, it shows up in a database.

As soon as we start working on it, it posts it to Slack, to a channel. You could do a lot. Do you use it in your personal life also? Yeah, for sure. My wife and I, we do a weekly family priorities where we have a list of some of this just logistics, like travel and expenses.

And some of it is also things that bothered us during the week that we want to talk about. And we have all of it. It's like a weekly running one-on-one doc that we discuss every week. It's been very, very useful. I've gotten so many requests from people to explain-- do a whole episode on how I use Notion.

And I'm like, I don't even know where to start. It feels so personal. It's like, well, I want to take a trip. So I make a database. And I put all the trips in the database. And then each one has a page. And each one has a checklist. And it's like, you could go down these rabbit holes.

But at the highest level, you can combine everything you would normally put in a spreadsheet, but in a database, which could do more. Everything you would put in a document could do more. You can link it all together and search it. And I don't know, that tool-- You can publish it as a website.

Yeah. OK, I know we both use email as kind of a triaging automated system. I'm using Superhuman. I know you have used Superhuman, are considering building something, or building it right now. How do you think first before the systems, just in general, about email? Because I think all of us, work, personal, feel overwhelmed by email.

We'll start with the good things about email, which is email is threaded. And email is quantized. So we'll take Slack as a good opposite example. Slack is effectively a superset of text messaging. It is a relentless firehose of information. Anyone who's worked in a company that uses Slack, if you go offline for like three days, and you come back to Slack, you feel hopelessly behind.

And you have to like scroll and figure out, what did I miss? Because it's just, it's all coming. It's like being in a WhatsApp group. Like I just checked earlier today, there's some thread that I don't, I haven't even checked what it is yet, that must have blown up.

I have like 128 messages on WhatsApp. It's like, am I really going to be able to filter through all of those to see if any of them are relevant? Probably not. You just end up muting them, and then they go away. So the nice thing about email is that because it's threaded and quantized, each idea is encapsulated in one item.

People can respond on that one item, but it doesn't impact you anymore. You could just mute. It's like, oh, I don't want to engage in this topic. And you can delete it, you can mute it, whatever you want to do, but you don't miss all of the information from all of the people.

So the problem with email is that the signal to noise ratio in email is extremely low. Partly because anyone can just send you an email. I was actually talking to somebody about this very recently that all of these marketing agencies with dashes in their URL, like does anybody actually open those?

I cannot imagine that sending this much spam email is delivering value for anybody, but it must be. And there's just so much of it, and it's so hard to stay on top of it. So that's the major problem with email, is that anyone else can effectively impose their priority on you, onto your attention.

I don't have a great solution for it yet. We have really tried a lot of different tools. We ended up building our own comms tool to try to solve this problem. We're planning to externalize it, probably in Q1. My hope is that it'll be a drop-in replacement for Superhuman and Slack, and really any other workplace communication tool people are using.

Almost all of these tools are designed by people who are either social media product managers in their past life, or video game designers. They're not people who are designing tools with deep work as the major focus. That's really been the major effort that we've been working on there. - Within email, one thing that I think has helped, so yes, everyone has access to your inbox.

It can be overwhelming. The more you can view it as a thing that you can process quickly, the less you dwell on it. When I watch some people manage their inbox, it's I open an email, I open it, I think about it. And mine is like, first I'll just go through the inbox, and I'll be like, what can I just quickly delete?

And like, keyboard shortcut, and maybe it's not delete and archive, but it's like J-J-J-E-E-E-J-J. Like, I'm just trying to get everything out. I do like one pass. I know this breaks a lot of people's principles, which is like only touch an email twice or once. But I'm like, one pass, get rid of all the bad stuff that I don't even need.

And that's something that you can usually solve through delegation as well. Then when I'm going through it, it's like, each email is going to go somewhere. It's either going to be quickly replied to, or be filed to deal with later, or be hidden to come back later and dealt with.

Being able to do that quickly, I think is an underrated skill. I think a lot of people are like, well, I don't need to be the productivity export, learn the keyboard shortcuts, superhuman, or any tool like that that I'd have to pay for to just use my inbox. I don't know how to say anything other than like, I think you're wrong.

There's actually really good data on this, which I'm happy to share. Like there's so much data on how much more productive people are using hotkeys, or keyboard shortcuts. Depending on what your role is, there's a bunch of different studies trying for different tasks. People automatically, with a very short period of training, see something like a 10 to 40% increase in productivity for the rest of their lives, just by learning these shortcuts.

If you're in a role where you're doing a lot of manual clicking and typing, and you're in a particular tool a lot, that's on the higher end. If you just process email occasionally, it still is useful. There's a tremendous amount of evidence for why learning these is such a positive thing, and it's everybody needs to do it.

It's really what it comes down to. For very little effort, you get free productivity forever. - And this is not just true for email. Like most apps you use on your computer, and I imagine everyone knows how to copy and paste. - Yeah, exactly. - And like, take how simple copy and paste makes your life.

Instead of dragging your cursor up and clicking the icon, that applies everywhere. I remember working in finance, like I went to an Excel training, and it was like, you can go deep if you're in a specific area, and it will also greatly increase your productivity. But I think at a bare minimum, email shortcuts, which for some reason, even Gmail, you have to manually enable.

So go enable it, go look up, used to be able to buy stickers and put them on your keyboard, but I think you can pretty quickly learn them, is such an unlock. - Yeah, definitely. - And within Slack or whatever app you use, I would encourage that. And then broad computer-wise, just the number of people that I've witnessed not using on a Mac, Command + Tab, Control + Tab or Alt + Tab on a PC, just to be able to jump between windows within an app, within windows outside of an app, maybe Chrome, to be able to switch through tabs or whatever browser you're using.

- Yeah, a few other things related to that, I would say Text Expander, which I know is something that you're familiar with. Text Expander is an awesome one when you're using snippets across all these different platforms. - And the principle there, for people who don't know, you can create a piece of text that is your address.

You can have a shortcut for it to be able to drop your address in. And if you don't wanna download an app and do this, I actually use just the default Mac text replacement. So if I type ch @ symbol, it replaces it with my email address. So there are a few things where I've actually just built it into iOS, which is great, it works on your phone, which I don't know if Text Expander works on your phone.

They might-- - I've used it on my phone. - But that's the hack on a phone, is you can go in and create a keyboard that would just turn OMW into On My Way, or whatever things you might say a lot. Or you can use Text Expander, which has more functionality.

Superhuman has snippets built into it. - Nice thing about Text Expander, I don't use the specific key shortcuts, like ch @. I pretty much exclusively use it, the search functionality. So you can just paste the entire snippet in, and it will just infer as you're typing. You can start the search on Text Expander, and as you're typing in words, it filters it down to the one that you want.

So you don't have to memorize nearly as many hotkeys. - So I use Alfred instead of Text Expander for this. And the thing I love is that it merges your snippets with your history of your clipboard. So with the same keyboard shortcut, I pull up anything I've ever copied and pasted in the last, I don't know how long it goes, 30 days, with a priority for anything that's a snippet.

So I find myself, and the clipboard functionality works with photos. So if I wanna go screen grab three things, I screen grab, screen grab, screen grab, and I can go in and I think it's option command C, pulls up and I'm like, I wanna paste this, paste this, paste this.

And so it combines the two. But Text Expander, I also don't use the keyboard shortcuts for it. It's more about being able to have a database of things that I wanna throw in. And then I use snippets within Superhuman, which I could probably combine those. I can't remember, but I think it includes some HTML or hybrid formatting.

So if you wanted to say like, here's a link to my website, when you paste it, you could actually have the HTML in there. I can't remember if Alfred does that, but I believe Text Expander does. So that's one. - The thing I always try to help people do is instead of using their cursor and going down into their dock to open each app, they do command space and you type the thing.

It's a very coder way to do it, but it's much, much, much faster. Instead of like going down, which of these 40 icons is the one that I want? And it really slows things down when you have to do that. - Yeah, my dock is now like five things.

- Yeah, mine too. - Because I just searched for it. I've disabled spotlight for Alfred, which is like a tool to do the same. There's another tool that if I can find it, I'll put in the show notes that people have recommended. I believe it has-- - It could be Raycast.

- Raycast. I knew it had the word Ray in it as an alternative, which I've heard great things about. The one thing we didn't talk about in depth is calendaring. And you mentioned earlier, like doing an audit, making sure things are in your calendar. I wanna talk about it because I think I'm terrible at it.

On the whole, I looked at this list, I was like, I'm great at Notion, I'm great at email, I'm great at a lot of productivity things. If you look at my calendar, there's like four things on it. And sometimes my EA's like, "Oh, you need to do this thing, "she'll put it on my calendar." And I just don't, I'm like, "Well, why would I do it?

"I can do it later." How have you created discipline to use your calendar both as a place of what to do and as a record of what you did? - I wish I had a better answer other than to have discipline to do that. Let's say I ostensibly set a priority as I wanna make sure that I am spending a lot of time recruiting new engineers.

That's my priority for this month. Having that feedback mechanism of my EA giving you my monthly report and saying, "You spent one hour doing this thing this whole month." That's a real wake up call for me to say, "Oh, wow, I need to move things around." Because my stated priority is clearly not reflected in my empirical record of priorities.

Having that feedback loop, I think, helps with the discipline because it allows me to reorient my time. It probably started much more so in the retroactively capturing what I'm doing. And then I started proactively looking into the future and projecting what I would be spending my time on. So that's probably the order in which that was more of a thing because this whole process for me actually started when I was doing a lot of software consulting work.

And it was just a pragmatic aspect of I need to know who to bill how much time for. That's really where it started for me was I started keeping track historically of how much time I was spending on each project. And then I realized that I now have to project into the future how many projects can I manage at the same time.

And I would add those blocks into my calendar. And I realized I can only support this many projects. So I would say that's probably the order that I would approach it if you were to give it a shot. - And are you naturally not a procrastinator? - I'm very much a procrastinator.

Part of the answer is I create a lot of scaffolding around how I spend my time and what my priorities are. I can give a recent example, something I need to deliver by next Wednesday. I'm not gonna put it on my calendar for tomorrow because I know I'm just gonna not do it.

So I'd usually, I'll put it on my calendar probably for Tuesday. And I think it's gonna take me about four hours. So I block off four hours on Tuesday 'cause I have to deliver it by Wednesday. I'm not gonna be super optimistic about what is gonna happen 'cause I have enough of these empirical records to know how this pattern goes is I'm just gonna not do it until Tuesday anyway.

So I might as well just put it on Tuesday. Being able to project how you're spending your time, it brings procrastination into much more focus. Let's say you know you need to do this by Wednesday and you say, yeah, I'll just deal with this later. I have plenty of time.

But if you look at your calendar and you realize that actually you do not, you don't have any time to do this between now and next week you have to figure out how to move your calendar around that it brings it much more into focus and makes procrastination a lot harder because you would just realize that you either have to cut things from what your current calendar is or you have to bring it further back in time to be able to do it earlier.

My challenge might actually be less that I don't wanna do the important thing but that some random thing has come up that I'm excited about. And to go full circle with an example, recently I realized that someone who as a company we owe money to sent me a bill, sat in the inbox, forgot to pay it.

And I was like, there should just be a system where someone could, you know, when I work with vendors I send them an email to like invoicing at and I send them our invoice and it gets paid. So I was like, oh, I need something like that. And I was like, oh, what are the tools?

Oh, well, QuickBooks can do it and bill.com can do it and Melio can do it and a few banks have it. And it's like, ooh, I wanna go play with all the, and I was like, I just got excited. So to go back, I'm sure many people listening are like that sounds like a horrible task.

I would never wanna spend my free time researching accounting software to track accounts payable. - Sounds like a really good pass to delegate to an EA. - For you, for me, I was like, it was exciting. Like I was, how you might feel programming, I felt evaluating accounting tools.

And so I'm like, gosh, today I have to do this thing but this thing that's really exciting. I think maybe what I need to get better at is like, it's actually less about when I put the time for the thing I do. It's about capturing the thing I'm exciting about and putting it somewhere so that I know I get to do it.

- Yeah, I do this all the time. If I was to show you my calendar now, you would see there's two CSS properties that somehow I just missed that they were released, which is I've been using Flexbox for a lot of things and grid is now a thing. Somehow I missed that, which is a really cool way of orienting items in CSS.

The other one that I missed is clamp. Somehow I missed when that got released, which effectively does away with all these really tedious media queries. And I was super excited when I discovered this. How did I miss that this exists? And I felt really motivated to do it at that exact moment.

But then I looked at my calendar, it's like, I don't have time. So I put an hour on my calendar. The next time I had availability, which was like three days later, I put the links in there. I was able to externalize it and say, I'm not gonna forget about this.

It's in my calendar. I will eventually get to it. And I'm gonna learn these things. - Have you gotten to do that yet? - No, I think it might be today, actually. - We should, I won't keep you from CSS, which similarly sounds like something I enjoy going down rabbit hole.

I think I just enjoy going down learning rabbit holes too much. So that makes it just super challenging. - Yeah, and I think where a lot of people struggle with this and this is certainly where I used to struggle with this, is that it feels like if you don't do it now, it's gonna just fall into the void.

But if you put it on your calendar and you're disciplined about sticking to your calendar, you will get to it. The nice thing about calendars is that things happen linearly. Like time will elapse. You will eventually get to the item and you will have to do something with it.

- I think one example that actually helped when it comes to email, a lot of people that are listening probably leave their email open all day, which I think is a habit that sometimes I'm better and sometimes I'm worse at sticking to. And I thought, gosh, if I close my email, then I'll miss something.

What I found was when I don't look at my email for three hours, it's like I have so much exciting things to see. Like that joy that you would get these little blips of, instead of getting the little blips, you got a big one. And I actually liked it more.

So right now I haven't looked at my email our entire conversation and I'm like, ooh, I'm kind of excited to go see what's in there and probably archive most of it. - So there's a useful tool, not coincidentally, the tool that we're building has a feature called scheduled delivery, which batches your messages.

So that even if you checked, you wouldn't see anything. It actually hides them from you until it's time that you specify. If you write out that you want to process email from one o'clock to two o'clock, it'll just hide everything from you. There's a way to break the glass and get the data if you want it, but it'll hide it from you until that moment.

So you don't feel this urge to compulsively check. There's a tool that I use that really inspired a lot of this, which is called Mailman. I think their website's Mailman HQ. Very, very simple product. All it does is it batches your email. And so you say, I want my email to be delivered to me at one o'clock and five o'clock, and that's it.

And so what's nice is it's useful to think about these things cognitively in terms of dopamine loops. If you check your email and there's nothing there, you don't get that dopamine reward. But if you constantly check, it's like, ooh, new information. Ooh, there's a little dot. Ooh, I can check that.

I feel like I just did something. I marked junk mail as done. I've achieved something. You get that dopamine reinforcement. And what's nice about these tools is that if you check it enough times and there's nothing new there, you eventually just give up. And that compulsive behavioral trait just evaporates.

And you don't feel that compulsive need to check anymore. The data on this stuff is really frightening. There's some data around use of Slack and other workplace communications tools like email. For knowledge workers, I think it was something like 60% of knowledge workers cannot go more than six minutes without checking a communications tool.

I think it was almost half of knowledge workers never at any point get more than 30 minutes of uninterrupted time ever, which I just, I cannot even fathom how people get work done, especially doing software development. It's just impossible. - I regularly miss messages during the workday 'cause I have my phone set to go into work mode, which doesn't surface anything.

I do think that, and I don't know if you're building this into your tool, there are probably a few things, and I don't know how to figure out what they are 'cause I don't have an obvious rule set that it's like, I would like to know about that. You could probably filter it on keyword or sender, but there are some things that I do wanna know about.

And then there are some things like the worst is on Slack. There is no way to have, and if anyone listening knows a way, let me know, a Google Drive integration that will notify you of some things, which like I shared something to someone and it wasn't shared and I meant to share it, but I went and said, anyone can edit it in our org, but I forgot to say with the link.

And I got a push on Slack that was like, "Hey, do you wanna grant access?" I was like, oh, this is so helpful. It was early in the morning. I could hit one button, grant access. But then someone was editing a doc and every minute I got a, "This person edited, this person edited." I was like, I don't, this is crazy.

Suppress it all. I would love to see some ability to kind of filter out that stuff, but let the, you missed a payment, come through that I need to resolve. - The signal to noise problem in communications is just fundamentally hard. We do have some specific heuristics on how we're solving that problem.

When it's intra-org, you can largely trust the other people in your org to be responsible stewards of your time. And so you can't do this with email. Like if you let every spam marketer set the priority, like everything, priority zero, interrupt him immediately. This is the highest priority thing.

You need to work with our agency. It's another one of these. But within your company, people are usually pretty good about setting something to the right level of priority or setting a date in the future. It's one of the things that we were working on is you can say this will become high priority on Wednesday if you haven't done it by Wednesday.

(laughs) You can specify some of these things where you have like an escalation path over some time period. So yeah, it's a fundamentally hard problem and I don't think any of these tools have solved it. - But I've also played with a little is around AI and all these things.

I'm curious how AI has fit into, to go back to our earlier conversation, delegation and how much you or even your EAs have been able to lean into it as a way to become more efficient. - It's incredibly helpful for things like doing meeting summaries. I don't think that we're leveraging it as much as we could be.

It would be interesting, this is maybe a question I should just ask some folks at Athena, is that if Athena is a staffing agency or some of these other companies, if they view themselves as staffing agencies, that's fine. But it would be interesting as this category evolves, if they view themselves much more as a task completion company and the abstraction of having people and staff is actually less important than the completion of tasks on some regular basis, you can imagine a world where you record loom of your workflow throughout the entire day.

And there's some AI process that analyzes that video and then recommends how it could automate half of the things that you did. And it wouldn't require a person and you would just say like, accept. I accept this delegation forever at zero cost. That would be pretty awesome. And I don't think we're that far away from it.

I would bet within the next 10 years, we have something that's fairly similar to that. - Right now, my solution has been to get a good sense of the things that I wanna do and then encourage my EA not to think that using AI is cheating. You know, it's like, this is a tool.

If it can make you more efficient, use it. And I've found that it's not good at necessarily doing things, the execution of things, but it's fairly good at the brainstorming and thinking of things. What topics would I wanna talk about? A use case that I'd never even considered that a friend of mine recently did was, he took all of his biomarkers from his most recent health tests, where he went and got all these labs done.

And he was like, talk to me about them. Here's all of them. Here's everything about me. Here's the history. What can you interpret from this? - Oh, cool. - It didn't even cross my mind to take my blood labs and put them into chat GPT and see what it said.

- And there's lots of use cases you'll find as a parent where you're like, oh, make up a story about a dragon who likes fish tacos, because that's what my child wants to talk about. So you'll get to there. But I've started trying to think about, okay, it could be used for brainstorming.

It could be used for analyzing stuff. And as these app stores and plugins get better and better and it can do stuff, I'm super interested. Right now I'm like, it's not as good at the doing as the thinking, but I hope it gets there. And one tool we didn't talk about, I don't know how much you use Zapier, but I would say that is a tool that for the longest time I looked at is like, how would I use it?

It was almost like an EA. It was like, how would I use it? I would never use it. I would never use it. And then I adopt it and I've got all of these processes, like doing all of these things. Actually the way a friend of mine uses it is in the beginning of his voice notes, he just says like a category.

He's like work or food or health. And then he reads this voice note. The voice note gets transcribed through whisper memos or whisper notes and gets sent to a Zapier email, which looks at the first five words. And if one of these words is there, categorizes it and puts it in this place in notion and loops in the right person and all of those things.

And so it's pretty powerful. And I feel like I slept on it for too long thinking it was only a tool for business and realize there's just an infinite number of ways that you can loop together personal things. - For sure. Yeah, it's funny, the use of AI in a lot of these things and viewing it as cheating is, this came up in a conversation, I think as recently as last week within our engineering team, because we were interviewing engineers.

We did a live coding exercise and I don't know if you've seen CoPilot. - Yeah. - But it writes a lot of the code for you. And we had, basically we discovered last week that our live coding exercise no longer works because CoPilot will just give you the answer.

So we weren't sure like, do we make him turn off CoPilot? And I mentioned to the team, we just need to adapt. We need to change the expectations. We need to do adapt our live coding exercise because I remember when I was interviewing for programming jobs years ago, the guy who was interviewing me was more of an old school engineer.

And he felt like my use of an IDE, which I think at the time was Atom, he felt like that was cheating. So we had to move to a whiteboard to do this whole thing. It's like, nobody writes actual code on it. He's like, well, why are you sure that this executes?

It's like, I don't know. That's what my IDE tells me. It's mostly right. If there's any errors, it would tell me. And you just have to adapt and get used to the tools. Honestly, I've been back in the code base for a few months now. These new tools using GPT-4 and CoPilot, I'm legitimately double the productivity that I was before.

That's not an exaggeration. The amount of output, the reduction, and the number of times I get stuck on things, I'm legitimately producing twice as much as I was before all of this stuff was available. - I'm not an engineer by any means, but I would say I'm comfortable enough to figure out what code's trying to do.

And I was like, I have this idea. I want to build a page on our website where I can pull in a list of credit cards. We didn't talk at all about points and miles, which we don't need to, but I'm a nerd about it. And I was like, I want to be able to build a place where we can filter and sort and look at signup bonuses and reference a table of what points are worth and determine how much it's worth and all this stuff.

And I literally built a site that does all of this. And I am 100% sure it was well beyond the scope of what I was able to do on my own, because I feel like when it comes to writing JavaScript, I'm like, nope, I'm not great there. And I was just blown away.

The one challenge is when something breaks, 80% of the time, you could be like, hey, this is how it's broken. Can you help me? And then there's like 20% of the time where you're like, mm, no. And then you do, but funny enough, you think that this tool will do the same thing every time.

So I'll revert to where it started working. I'll copy it into a new chat and say, hey, I have this thing and it's not working. And the same tool that couldn't solve it will solve it. - It will self-reflect when you say, are you sure that's right? And it was like, oh, you know what?

- I missed something. - No, I missed something. Like that is weird. That is super weird. (laughs) Happens all the time. - So we talked a lot about how tracking what you're doing, whether it's time is interesting. I just briefly talked about putting biomarkers into GPT and what you can learn from them.

We could probably have an entire podcast that's completely separate from this about tracking your personal health data and learning from it. And you referenced levels a few times. I mentioned in the intro, can you just spend a few minutes and talk about what you can learn from tracking your own health data and maybe inspire people to dig deeper?

- Yeah, so levels is, we show you how food affects your health using biosensors, like a continuous glucose monitor I've went on here. It's just a patch on your arm. It shows you what your glucose levels are in real time and allows you to connect the dots on how what it is that you're eating is affecting your health.

For me personally, it's really just been more lifestyle focused. I would say for me, it has allowed me to see what I'm eating throughout the day and how that impacts my energy levels throughout the day of am I feeling tired? Are my hands shaky? Why am I not able to focus?

Why do I have brain fog? And you often uncover how many of those things are just because of what you're eating. The simplest example that I can give, which was really my first eye-opening moment was discovering that my super healthy orange juice and oatmeal breakfast was actually the source of most of my problems throughout the day.

And I don't even like oatmeal. It was just, I felt like I had to do it because it was healthy and it was actually causing all of these problems. So there's nothing like having ground truth data when you're trying to make feedback loops on understanding how to improve. So that's the core of the product.

- Yeah, I mean, I have used the product on multiple occasions. And I think the one thing that was the most interesting beyond just seeing how your body reacts is doing it with someone else and seeing that like you're just different. And so for me, I don't know why, but a cinnamon roll doesn't really spike my glucose at all.

And my wife, it is through the roof. You think about a lot of our advice for health is non-personal. And so my takeaway from it was I basically watched everything I ate and how it affected me in a window of time. And my wife did the same thing and both like interestingly and unfortunately, they were very different.

Which is disappointing 'cause it means if we wanna target similar behaviors in our body, we can't eat the same things, which makes life more complicated. But it just makes you question, oh, if someone says this is a definitive health truth, there are some, but there are also others that aren't.

- For sure, this is a very new field. We've only been able to measure these things in real time for single digit years. And so a lot of the studies, it's still unknown to science what normal glucose levels even are. We're actually running the study now. It's the largest study of its kind with about 50,000 people to just establish what normal glucose even is.

Which is hard to believe that we don't know that, but we don't. What's interesting about it is that there are so many things that can impact your health and how your body responds to this. And so much of it is still yet to be discovered. We know that microbiome plays a huge role in this.

There's a lot of really cool studies out of Israel, I think at Iran Sehgal's lab, where they knock out the microbiome of mice. They can effectively replace their microbiome with that of another mouse. And they're able to change how those mice respond to different foods through microbiome transfers. Sleep has a huge impact.

Hormones have a massive impact on cycles throughout the month. How much you exercise has a huge impact. If you did a huge workout, if your muscles can absorb a lot of glucose. There are so many variables that can impact these things. Genetics play a factor. So figuring out what is causing all of this, I think is gonna be a really interesting area of research over the next 10 to 20 years.

- You started off saying it's about how food affects your body, but it's also, sounds a little meta, but it's like how your body can affect how your food affects your body. - Yeah, sure. - And I know like exercising after eating can actually change how your body processes food.

You can see it in the data. And so I guess that's a pitch for walking after you eat. It doesn't have to be a lot of exercise, right? - It's a lot less than people think. You know, just like a short walk after eating, especially like a high carb meal, has a measurable impact on how your body responds.

- I'll put a link in the show notes to where people can go check it out. I remember it used to be invite only, but now I think anyone can sign up. You've obviously optimized a lot of your work life, the tools you use, everything. Anything on the personal side?

- Since, you know, this is all the hacks, I think one hack that is a really useful one that has helped me a lot, just stay present throughout the day, is set alarms for everything. So the first thing I do when I wake up in the morning, I look at every meeting that I have throughout the day, and I set an alarm for when my next action needs to be.

So if I have a 9 a.m. meeting, I set an alarm for 9 a.m. If I have to leave for the airport at 6 p.m., I set an alarm for 6 p.m. And it has allowed me to, for one, not miss meetings and not be late to things. There are a lot of people who just rely on their Google Calendar alerts, and they are so inconsistent, and you end up missing things all the time.

But also it allows you to stay present. We've all been in meetings where you can see the person's constantly checking their watch, like what time is it, do I need to leave right now? If you have an alarm set, it's gonna go off. You can just relax. You don't have to carry that cognitive burden of what if I'm late, how much time has elapsed, how much time do I have left?

It'll tell you, it'll be fine. And so I found that as a tool to just be able to maintain presence is a really good one. - That is super interesting. I've relied on the Google Calendar reminders don't work. I've actually, the interesting thing about Slack, so a lot of people, it's like Slack is the worst thing ever.

For all the hacks, our Slack instance has like three people in it. So it actually really exists more as a place to have a bunch of conversations and find those conversations. And I'm not sure if there's a better tool for that, but it means that Slack isn't that noisy.

And so the Google Calendar push to Slack as a DM, I just have that work, and it sends me a reminder one minute before. But I haven't thought about the fact that in order to guarantee that gets through, you have to let everything else through. And the alarm kind of pushes outside of that.

- The thing about Slack or just communication tools broadly, the fundamental problem that makes communication hard is that the number of people in a communication cluster scales linearly. So you have one person, two people, three people, it's just linear. But the number of edges between those nodes scales polynomially.

So the difference between 10 people and 100 people is not 10 times more, it's like a thousand times more. And so those communication pathways, you very quickly reach a point where you can no longer keep up with what's going on. I've talked to some founders who scaled companies and they say, "You have to treat every doubling "like it's a different company." Because primarily this comes from communication pathways, where it is no longer possible.

At a certain scale, you could spend all of your time, 100% of the day, just keeping up with what is happening in the company and not doing any work. And it would be really bad for company productivity, but you could absolutely do it. That is how much communication is being generated.

So you necessarily have to silo information and you have to figure out where that signal is. So it gets much, much harder once you hit even 20 something people. - This reminds me, and I really hope I'm not misattributing someone else, but I believe it was Bill Gurley, who is a well-known venture capitalist.

And the idea that he presents is when something's not working, you just assume that what you're doing now isn't the right answer. And I think it's a principle I've tried to apply to a lot of aspects of life. It's like, "Oh, communication is kind of broken. "Let's just assume we're not gonna keep doing it "how we're doing it." It's always so easy to just say like, "How do we tweak the thing we're doing a little bit?" But I've now kind of encouraged myself.

It's like, "Oh, if the way we do dinner isn't working, "let's not try to find easier recipes. "Let's see if we can outsource who picks our recipes "or something else." So I've tried to apply this business principle. And a lot of what I'm, because I don't have a job at a company with lots of employees, every time I hear you talk about these business ideas, there's a personal application that I'm processing.

That one was one big one for me, where it's like, "If it's not working, "just don't assume you can fix it. "Maybe assume something else is better." - For sure. - This has been fantastic. I told you before you started that, "Well, we're not gonna go that long. "I like to keep it tight." And there was just too much to cover.

So thank you for sticking around and going down so many paths. - For sure. Thanks for having me. (upbeat music) - Wow. If you made it this far, then I assume you also enjoyed this conversation as much as I did. Sam is amazing. And I am just so excited to be putting all of his knowledge to good use.

Again, if you want a copy of the delegation guide I put together with the team at Oceans, you can find it at allthehacks.com/delegate. And if you wanna check out Oceans or look into finding your own assistant with them, they're at oceansxyz.com. Feel free to let them know I sent you and I'm pretty sure you'll get hooked up with a deal.

Okay, this was a long one. So that's it for this week. I'll see you next week. (upbeat music) I wanna tell you about another podcast I love that goes deep on all things money. That means everything from money hacks to wealth building to early retirement. It's called the Personal Finance Podcast.

And it's much more about building generational wealth and spending your money on the things you value than it is about clipping coupons to save a dollar. It's hosted by my good friend, Andrew, who truly believes that everyone in this world can build wealth and his passion and excitement are what make this show so entertaining.

I know because I was a guest on the show in December, 2022, but recently I listened to an episode where Andrew shared 16 money stats that will blow your mind. And it was so crazy to learn things like 35% of millennials are not participating in their employer's retirement plan.

And that's just one of the many fascinating stats he shared. The Personal Finance Podcast has something for everyone. It's filled with so many tips and tactics and hacks to help you get better with your money and grow your wealth. So I highly recommend you check it out. Just search for the Personal Finance Podcast on Apple Podcasts, Spotify, or wherever you listen to podcasts and enjoy.