my grand ambition is for the next 5050 years of my life is to impact positively a billion people in the world every piece of writing is a call for the kind of person that you want to bring into your life bringing the essence of an idea very quickly and concisely to somebody try to distill it to someone see where you didn't make sense or where
they were like looking confused yeah I call this writing from conversation you're talking to people and you're getting a sense for what's Landing what's not Landing forced constraints are a really good way to stoke cre creativity it was why I love Twitter when I first started was because you had to distill your writing into such little
bite-sized thoughts so what do you do as a Creator to stay on The Cutting Edge of distribution I don't know how many people know this wait hold on hold on that's really good man hey man I'm so happy to be here finally meeting you person I know I know it's great to you this is like the classic Co story friendship I feel like
I've talked to you probably most days since like mid 2020 and we've somehow never met in person Yeah man so I'm thrilled what was the first thing that you ever wrote where you felt an enthusiasm for writing I mean this probably goes back to like way before any of the public stuff I've done so I don't know how many people know
this actually but I wrote I used to write a like what I've been reading newsletter I didn't know it was even called a newslet frankly like I used to I started by sending it out to 10 family and friends because I'm a pretty avid reader I would read kind of like weird books that were off the beaten path and a bunch of family and
friends I'd talk to them about it whenever we'd get together and so then they started saying like oh we want to know what you're reading so I literally like went on MailChimp and I set up like a little thing I like hand typed in 10 email addresses and I started sending out this once a month thing of the books I read with like my little takeaways and
then like a rating on the book this is like probably in 20145 that I started sending that out and every like few days someone would bring it up and they'd want to share it with a friend they'd ask me to like add a friend email I sent it every single month from like when I started until 2020 when I didn't have time to do
it anymore because of new stuff that had taken off so like for five plus years I sent it and it like slowly grew to be I don't know there was probably like 2,000 people or something that were on this list and it was like real people you know like at that point it was like people colleagues work like CEOs of the companies we were working
with Etc um but it was just a true passion thing like labor of love that I was doing and I really got a lot of energy out of it I just didn't know that that would then become a big part of my future like sending out things on a weekly basis yeah have you heard the story of uh Howard Marx no this is sort of what he did so he had a memo that he
used to literally hand mail to people he lick the envelope and everything you know throw the stamp on the top right corner and he wrote it for like a decade without anybody reading it and Morgan howel has this piece called Selfish writing where he says that this is the kind of writing that works really well he was just doing
it for himself he didn't care that people weren't weren't reading and that was just sort of how it was but he genuinely loved it and that's what kept Him going and now he's Howard marks but it started with a decade of no one reading his stuff I'm fascinated by people like Howard marks I mean frankly Warren Buffett is probably the OG of
this where when we think of a content creator we think of um you know some with the Creator economy whatever we want to call it today we think of like a YouTuber like a newsletter writer one of those things and really like the OG content creators Warren Buffett was the OG content creator he started writing
his annual shareholder letters in whatever like 1960 and it attracted an enormous number of people to this Cult of Berkshire Hathaway and it's hard to deny the fact that it has expanded the value the Enterprise value of the things that he's done and built over that period of time to the point now where he has 50,000
people show up in Omaha Nebraska to listen to him speak but he was all based around content that he was creating on an annual basis attracting people to the ideas he was putting out into the world and when he started there was no way that he thought that it would end up where it was right it was just something it was his way of thinking it was
clarifying thinking along the way I imagine Howard Marx was the same I imagine you know the most esoteric Financial writing that I've ever seen that I loved was Grant's interest rate Observer you've never worked in finance but um you know this guy I think his name is Jim Grant and he started writing this thing I imagine when he originally
wrote it it was like Howard marks like a hand mailed letter that he would send on I mean it was interest rates originally was the main thing but he would write this to piece once a month I think and it became the Bible of the fin Cal world where like the biggest fund managers the biggest you know the biggest Ballers on
Wall Street were paying tens of thousands of dollars a year to have access to this thing I don't know what the subscription is now it is extraordinarily expensive to get access and he still writes it it's a Once month thing that comes out but I imagine when he started it was just that was like yes I'm just GNA write the things that I
love writing on a monthly basis send them out to whoever cares and it builds over time this slow slow steady build when you were working in private Equity were you doing a lot of writing there only for myself so I've always been someone who has found my thinking clarified through writing in private equity and in early Consulting and all
these career tracks everything's about like the PowerPoint presentation and I never found that that was a thing that was conducive to me actually thinking clearly about a problem so before I would make a PowerPoint presentation I would actually write a memo if I had to do an investment thesis presentation my first step personally was I would have
to write a onepage memo to myself on why I wanted to do this investment why I thought it made sense and when I did that it would become very clear to me if it was actually a good investment or not if I could really simply clarify why we should be doing the investment yes or no you just immediately know because it
forces you to distill and clarify it was why I love Twitter when I first started was because you had to distill your writing into such little bite-sized thoughts that if you weren't clear on your thinking around it you couldn't do it it just wasn't possible so I I mean I was probably atypical for having a writing habit during my investing in
private Equity days now it's become much more common place I think people are starting to realize that I mean chth kind of popularized the one pager that he was doing during Co around all of his spcs and a lot of his Investments and I think it started to build the idea of written memos rather than PowerPoint
presentations I mean I see more Founders today than ever before pitching their fundraising with a memo rather than a rather than a deck yeah one of the things I'll do if I'm working on a piece and I'm stuck on something I'll have this feeling that whatever it is that I'm writing needs to get shorter more distilled and I will literally pop open
Twitter and I will write that out and try to meet the character constraint and just shorter and shorter and shorter and shorter and I find that to be really useful just the form factor of Twitter to just help me compress my ideas and I think I don't know if you write in Google Docs if you write on the platforms where you're sharing your
pieces but I remember I was once on a walk with Tyler Cowen and he said yeah I write all my blog posts in WordPress directly and then I just hit send and he's like something about WordPress gets my brain into the state of mind that I need in order to do it well that's fascinating um you know it makes me think of uh have you heard of the
creative the creative Cliff illusion no what's this it was this whole study that was done that basically people think that your most creative ideas come early in a creative session so you're like oh I sit down I'm feeling really creative I get my coffee I'm ready to rip and I'm going to sit down and the creative ideas
are going to start flowing and then I'm going to get tired and my creativity is going to fall off a cliff and I need to just move on and if you ask people what they did was they went and asked people to map how their creativity would go over over time and they basically said it was going to go like this like just a
downward slope and what actually happens is that you hit a point where you're like struggling and then your creative ideas start really ramping and it's through that kind of like trudging through the mud of the creative session that you end up unlocking your most creative ideas so for you what made me think of it was that whole idea of like
when you get stuck then you go into Twitter and you start trying to really distill it and work with it like you're allowing yourself to sit with it andge through the mud metaphorically in order to get to that creative unlock Ed Sheeran has an analogy where he says it's like running the water tap and at the beginning it's dirty and it's brown
and stuff like that you need to get the the dirty water out and only later does it become clean I love that running the water tap um that's very very good yeah I I always thought this was a really interesting thing with creativity I forced constraints are a really good way to stoke creativity too forcing yourself to try to write it into shorter
bite-sized things to cut more and more and more I've seen people say you know when in doubt just cut and like if you have any shred of Doubt just cut the thing whatever it is I always found Twitter to be really helpful for that I think I mean for me Twitter made me a much much better writer because of that forced constraint and even though people
say well you were writing threads which allow you to write longer there's still a lot of constraint in having to close off an idea in a single tweet not just have it be like run on from one to the next um and and that does just force you to do different things it was um Dr Zeus was like the famous example of this
right he made the bet with the publisher that he could you've never heard this story so uh Dr Zeus wrote I'm and I'm GNA blank on which book it was that he wrote but he wrote a book using only a hundred different words and it became a massive bestseller and then he bet his publisher that he could write a book
that was a bestseller with under 50 total different words used in the book and the publish said no way and he wrote green eggs and ham with 49 different words total and it became you know it sold over 10 million copies it's been this enormous success and so it's the whole idea that forced constraints actually breed creativity he was forced
to be creative and to use words in different ways and rhyme things and um this amazing amazing uh you know explosion of innovation and insights that comes from that forced constraint when you look at your writing what is the thing that you are the most dissatisfied with what is the place where you feel you look at what your work looks like you're like ah
I wish that was better on a regular basis yeah I would say the thing I'm always wrestling with is remaining authentic and keeping the soul in the work and I actually think I do a good job of this but not an exceptional job of this if you think about writers on a spectrum from like the growth hacki grow on social media at
all costs on one end you know that's like here are 10 TED Talks that will change your life a bunch of Chrome extensions that'll change your life that kind of thing right to the most heartfelt Soul induced writers on the other end someone like a Maria papova uh Tim Urban where like you might not hear from them for a while but when the thing
comes you are damn well reading that cuz you know it's going to be incredible I struggle with where I want to sit on that Spectrum I know it's not on this end of the spectrum and I know it's not all the way on that end of the spectrum because I think I need to find the balance because my goals are to reach
people and impact tons of people walk me through the tradeoffs of both sides so on one end of the spectrum on the growth hacky end of the spectrum the positive is you can grow really quickly and reach a lot of people it's a very clear benefit that people have experienced I think the negatives there's a long list
of negatives there's no connection with the people that you're interacting with no one knows who you are no one knows anything about who you are uh no one I don't think is going to durably like buy things from you if you're trying to build a business around that and there's no soul in it like I would not be proud to tell my son that that's what I did
right like that here's something daddy created I'm not going to be proud to show him some like here or 10 you know free university courses that'll change your life whatever right like what he's going to look at me like I'm crazy um so that's one end of the spectrum then the other end of the spectrum you know the
incredible benefit is like people know your soul you're exposing your soul on a daily basis the way you think about the world you know you're Shifting the Overton window around different topics in a real way where you can expand the level of discourse around something I mean Tim's uh you know what's our problem his new book like it's a Tome
that is going to be out there forever and could impact the way that people think about the world and how we solve our problems most people won't ever read it because it's too big andse but the people that do might be the like taste makers of society that do start to shift because they're thinking about the problem differently that's the positive
the negative is the Cadence is impossible to control so your growth is always going to be constrained because you can't be publishing things on a regular basis with that level of Soul involved it's just too you would die like too draining creatively to do that on a daily basis and so you're trading off the reach I think in a lot of cases
uh you're trading off the ability to go and impact you know a billion people with your writing or hundreds of millions of people with your writing so my perspective has always been that I need to find where my place is on that spectrum and how to maintain a level of authenticity and a level of soul in things that I'm putting out into the
world while not giving up what my grand ambition is for the next 50 years of my life which is to impact positiv a billion people in the world and it sounds like a ridiculous number but when you talk about over 50 years it actually isn't that ridiculous if I was saying I wanted to do that over five years pretty
ridiculous but I don't believe in doing anything if I'm not going to do it for the next 30 40 50 years of my life I've been as you were talking about those deeper pieces the word that was coming to mind for me was excavation and those pieces that have have soul you have to excavate reality or yourself and excavation is a good word for this
because you don't always have a plan when you're Excavating something you have a compass a true north of some sorts you're always sort of digging down but surprise is inherent within excavation and you can't really map that out like an archaeologist never really knows when they're going to stumble upon ruin same with a geologist and oil but
there are tools that an archaeologist or geologist can use in order to find what they're looking for it's really a metaphor for Life excavation too right it's sort of you set your true north you set your compass and you go exploring and it's probably the most fun and engaging and fulfilling way to live your life it's probably also a risky way to
live your life it's not highly certain that you're going to find gold along the way or the hell was certainty it's easy to say that I think for us um and it goes both ways right like it's easy to say sitting here you know having a level of financial Comfort having a level of family comfort to say like to hell with certainty I would you know
drop everything to go do this job and for some people they I really don't think they have the luxury of saying to hell with certainty and so I like I often have to ratchet back thing the way I think about the world for that reason some people they need certainty because they need to just provide for whoever it
is in their life for their family for their loved ones it's why I think like when I look at that spectrum of people I totally understand people on every end of the spectrum and I respect it and I have like tons of respect for anyone that's willing to put themselves out into the world and create content whether it's on the hacky end or whether
it's on the Soulful end whatever you choose to do I think the thing is being aware of the game you're playing yeah I mean I could also take the opposite side where I think that there's something in prosperity that takes away some of that excavation you know there's a reason that many of the poorest countries in
the world are the closest to God there's a reason that we have the metaphor of the starving artist when you're starving when you're hungry this is why people who are religious they fast when you don't have the nutrients inside of you and you almost have to like stretch and yearn there's something creatively that you can access have you heard of um phes
yeah thees of my lead yeah of course so there's this amazing story about thees of myus uh that so thees was for those who don't know sort of the philosopher before Aristotle before all of the great philosophers we know of phes was this incredible Greek philosopher and it was before philosophy was cool basically so
no one respected thees he was brilliant deep thinker a scientist before there were tons of scientists that had proliferated and he basically walked through life gaining no respect from those around him because in my mind he was speaking a language that other people weren't speaking yet the language was still money and financial success so
because he didn't have wealth and he hadn't achieved business business success in any way he did not receive the respect from society and there's this great story of thy uh sort of lamenting the fact that he was not gaining the respect that he believed that he deserved and so he decided to change that and predicted
what the next Summer's weather would be on the basis of his scientific calculations and because he knew that it was going to be a warm dry summer he predicted there would be an incredible Olive Harvest and he went and bought up all of the olive presses in the entire region well then it was an amazing Olive Harvest and he had a monopoly on all of
the things that were needed in order to make something of that and became fabulously wealthy at which point everyone all of a sudden respected him and it's such an amazing story to me because on one side it's you need to speak a language that other people understand at a point in time the other piece of it
is there's just a fundamental difference between inputs and outputs for everyone the world is only going to appreciate the outputs where you might be falling in love with the inputs all on the way thees was probably very happy and fulfilled by all of his work his philosophy His science but until he actually generated the outputs that the
world understood there was nothing for him to gain from it societally yeah well I look at someone like Peter teal who was coming to mind as you were saying that I mean Peter is looking in such strange places for ideas and he's willing to entertain things that most people are not and look at the eye that that gives him right the problem with
certainty is that uh insistence on certainty leads to consensus thinking and so much of writing is from breaking away from the consensus whether that's how you write whether that's the stories that you tell whether that's the analogies that you pull from and the compass of curiosity when it's untethered by social expectations can
take you to those places yeah there's a famous saying in investing that applies to Peter teal that the goal is for every to agree with you later um and it's really true I think the same applies to some of this creative work I also am of two minds on this one side of me says yes the best writing comes from non-consensus
thinking the other side of me says there is an amazing world of writing that is taking things that have already been known or said and saying them 10% better and I I would argue that if you you looked at within the non-fiction realm as an example if you look at like the power law successes the you know the 0.001% successes I would guess 95% of those
are just an idea or set of ideas that already existed that are put into a slightly more beautiful package and delivered habits everyone has known for forever that habits are important it's great to have good habits it's bad to have bad habits there's clear ways to you know shift your habits over time James Clear took that and turned it into
a beautiful package so well written so concise into a clear framework and delivered it to people and it changed the world 10 million plus copies sold you know it'll continue to sell in perpetuity there are very few non-fiction books that I think are TR like it's truly a novel dramatically different Tim Ferris the 4-Hour Work
Week dramatically different no one had talked about those things when he came out with that book I think that's few and far between though I think most of the things that come out that really do create a massive broad widescale impact are just like a slightly better turn on something that people sort of know in the back of their minds yeah I totally
feel that I mean I always think of many of my favorite teachers changed my life I'm in class with them and the ideas are vibrant they didn't come up with those ideas they are taking existing ideas and they're adding life to them and adding life I like that that is what I come back to of if you look at brain studies
of when people are reading ideas that they're already familiar with when people are reading cliches the brain just doesn't light up we become desensitized it feels rot and routine and so much of I think that what you're trying to get at here is that good non-fiction writing can take an existing idea and saturated it with a new flare
and that's what makes it really good yeah so when you say that as it relates to my own writing and how I think about it my entire goal is to if I were to try to distill it into a single sentence is to help people ask better questions about their own life I have long believed that it is totally impossible for to give anyone any answers about how
to live their life because everyone's map of the world their reality is so so different I can't tell a 70-year-old person how to wrestle and you know figure out the answer to whatever it is and the best things in life don't come from finding better answers they come from asking better questions so if I can
help people ask slightly better questions wrestle with the questions in a slightly new or slightly different way I think that can create a really dramatic impact or it can create a tiny impact that has Ripple effects in their life and so when I think about writing when I think about any new thing I'm taking on whether it's book or whether
it's a newsletter or different things I'm putting out into the world I'm always trying to figure out take something that is known an idea that's interesting something that has sparked my curiosity and then what is my way of wrestling with it like how has it applied to my life in a unique or interesting way how
have I struggled with that problem whatever the problem is and how can I help people take the way I've struggled with it and figure out how to struggle with it a little bit better than they were before bring it to the top of their mind a little bit more that I think is where at least for me where I find the gold and when I write something that I
come away feeling really energized by it I can't wait for this to be out in the world that is what it is about the peace that gets me excited what does an epiphany feel like for you when I read listen to or meet with someone and I leave that moment wanting to go Sprint and run around and go crazy that's an epiphany for me when I get so much
energy all of a sudden I had a lunch yesterday uh with a very successful individual who is so passionate about this one pretty weird esoteric thing that I actually wouldn't say was like the most interesting thing in the world to me going into that lunch I left literally wanting to go to the ends of the Earth wanting to like understand
that more engage with it more you know be a part of it in any way that I could that to me is an epiphany like when you leave so energized you need to go run on a treadmill to calm yourself down that's what an epiphany feels like to me yeah what about you wait hold on hold on that's really good man the image that
came to mind for me was um The Yellow Brick Road and The Wizard of Oz okay and that essentially what an epiphany is is realizing that there is a path to some beautiful Tower at the end that you hadn't seen before and you can just run to that Promised Land because that is so much of what for me is an epiphany it's like the world begins to sort of feel
enclosed and it sort of begins to lose oxygen and all of a sudden there's been this infusion of air and I can just race to this promised land and I get so excited about that and the way that you describe epiphany is exactly how I feel it it is a rush of energy and it flows for me from like my gut up and it is a feeling it is not my mind and when I'm
writing for my mind the writing tends to be Bland and sterile when I'm writing for my body and I have that lionesque rush I just want to Roar the Roar resonates with me yeah because what I notice post Epiphany is that my running going crazy is I cannot wait to tell like 20 people about that thing whatever it is like I have to call my
wife I have to text some of my friends that I'll constantly text about these things I have to go share the thing that I was just inspired by because it feels crazy to me for it to be bottled up within me like I need to start going and trying to teach the thing to someone else or talk about it with someone else
uh because it feels like an injustice for that excitement to be bottled up I know in your writing process you don't have much of a Content calendar you get excited about something and you get right to it and I think that it provides a lot of validation to an idea that I increasingly agree with which is that people don't have ideas ideas have
people and that you can literally be consumed by an idea and that idea can inhabit you and what both of us feel deeply is this need to share this need to express this need to teach and if I can't do that I just feel dead I just want to die if I can't have that expression that idea is living inside of me and it has
to get out it's like my mission ideas have people I feel like that's going to stick with me I really really like that it is the challenge I think for most people is they don't give them eles enough time to just sit there's that blae Pascal it's like very cliche quote now that like you know all of Humanity's problems stem from man's inability to
sit in a room alone and it's really true Bill Gates invented his think week because he needed space for an entire week to just escape and to just think and to read and sit with ideas and slowing down like that allowed him to identify the things that were going to dramatically improve the future of what he was building but we all need need a
version of that where we can just sit with the things in our life whether you're a creative person or Not by the way whether you consider yourself a writer or a Creator or if you're just trying to get to that step function Improvement in your life in whatever area you need to create the space to just sit with the idea and to not feel
the need to create movement and progress we live in such a movement and progress obsessed Society I am a huge victim of that over the years I have like had to rewire my brain to be comfortable not making progress on things not having some ambitious goal around a thing because everything I want to be the best
at it I want to get better at the thing I want to hit my time whatever it is and it's really uncomfortable for me to just sit like that but it's the only way that you allow those ideas to take hold because if you spark that idea in your gut and you feel it a little bit and then you go off and do a million other things and you went and play golf and
you go to church you barrage by all sorts of other stimuli the idea never really gets to take hold have you read George gilder's work no I think he's actually out of Stanford so George Gilder is a sort of esoteric libertarian Economist okay and he has a oneliner that I really like which is that all creativity is
surprise that all of innovation is surprise and that the way that you create value is that you create useful surprise you bring useful surprise into the world because if it wasn't a surprise it would already be it would already be priced in if it wasn't a surprise then it wouldn't be Innovation and I think that what you're getting at
here is how do you create space and cultivate a life to generate surprise cultivate a life to generate surprise it's like creating I think in systems a lot and thinking about how you create systems for surprise is an interesting it's a it's a paradox weird it's a weird idea like how do you create systems in your life that
cultivate surprise because I often with my own writing I think about okay what do I do in order to create those moments like the inspiration if I were to distill it like there's a huge component that's consuming you need to open the funnel to tons of interesting ideas at the top end in order to get sparked in order to have those things intermingle
in your mind it's what are you reading what are you listening to who are you spending time with what conversation are you having who are you inspired by what are the environments you're in and then there's that next layer which is what we're talking about which is like that middle layer that everyone overlooks you think oh consume and now
I'm going to write but the middle layer is where the gold is the middle layer is the sitting and thinking or it's the walking and thinking where you're not listening to an audiobook on 2x speed you're not listening to a podcast you're just sitting there and thinking and that I think like the system for creativity
for me is that middle layer it's the just thinking allowing ideas to connect and bounce around in your mind bouncing those ideas off someone to see where did it connect with them where did it Miss the mark how did they react to it like the Fineman technique side of it where you're sort of teaching the idea to a 5-year-old quote unquote that is that
like beautiful sludgy yucky middle layer of creativity that's the real key to the whole system if you will and surrounding yourself with people who ask good questions and open up new Landscapes of Consciousness that's the entire game I mean my if I have one goal in life I don't care much about money paradoxically I've made much more money
when I stopped caring about money um which is a I think probably a Common Thread among really um successful people but I really care about my currency of life if you will is the interesting people I feel like I can collect in my life and connect with each other and spend time around because I feel more
energy having an amazing conversation with someone I think is really smart oneon-one or being in a room where there's five people having this amazing conversation that I get to be a fly on thewall for than almost anything else in my life in a professional is setting there's um you know like the Michi family uh started funding the the Arts
and designers and artists and architects in 15th C in 15th century Florence and all of them flocked to Florence at one point in time in history because the medich were the first people that were actually funding their work all of a sudden you have this unbelievably Lively discourse in one place at one point in time and what happens the Renaissance
gets sparked you have to find in your own life how to get yourself into that little mini 15th century Florence amen like what is that for your life for a lot of people their college campus is the first time they feel that like they're in an environment with big thinkers and people that they're around and then they leave and they never
experience 15th century Florence again their entire life and my opinion is that all goes to that Benjamin Franklin quote like a lot of people die at 25 and we don't bury them until they're 80 if you lose that if you lose an environment where you are pushed where there are people forcing you to think bigger where there are people that are questioning
your assumptions causing you to think differently about problems talking about interesting problems that you get to listen to if you lose that what's the point I think that we're hitting at two things here the first is people who show you avenues for exploration that you had never seen before and then the second is
that sense of curiosity paired with a kind of radical honesty I was with a friend a few days ago and I was just blabbing through something and he just looks at me he goes cut sh out of your life I get that someone else does this but that's not you cut it out what does your life look like if you just cut sh out and you just live in a way that's
aligned with your nature what does that look like and that interaction maybe took 8 seconds honesty paired with the new space for for exploration and all of a sudden I feel like like I have white space where I was previously stuck it's so funny how he probably hasn't thought about that inter that interaction since
he had it yeah and he left you with one idea that took five seconds and the impact might have 20 years of value on your life that one thing that he said and I think about that constantly with my writing or things that I put out into the world that one tiny thing you say the way you say it can change someone's entire
course of their life without you knowing it you know what I've noticed that I find to be very strange is the sentences that I've written that seem to really impact people are not the ones that I thought were the most eloquent they weren't the ones that I wrote and was like oh wow that's a great sentence often they're just really
mundane things that have come out that then get repeated back to me many months later I'm like that was the sentence and there's a few things there the first is often the pursuit of el of eloquence it's worthy to a point but I think that a lot of us are trained as writers to try to sound like novelists and it's often not worth pursuing but also that
there isn't a huge correlation sometimes between how hard you work on something and how well it ends up doing from a sentence to a piece a lot of people obsess over sounding smart to the smartest people in the room M and I understand it but it's a blinding Pursuit yeah and when you do that when you're focused on that you have to
understand there's trade-offs to everything and if you're trying to sound smart to the smartest people in the room there is going to be a whole lot of people who you are not able to connect with because of the way that you're pursuing things I have never wanted to sound like the smartest person to the smartest people in the room if those
people enjoy the things I'm putting out into the world I want it to be because they feel that it's real they can feel that it's authentic and I think that I've done an okay job of that I think I can always get better and continue to improve on that but I don't want to impress the smartest people in the room by just sounding so eloquent like an
amazing novelist and sharing things I want to be able to impact a regular person that is living their life to be able to live slightly better because of something that they read and that comes with speaking in simple terms that anyone can engage with and anyone can take in any direction that's not talking down to people that's not you know it's
distilling something it's forcing the constraint to use Simple language when you share something I saw Morgan housel on your Show recently and he's talking about that he's one of the best in the world at that he create he took a set of ideas and breathed life into them by making them so accessible to anyone in
the world and smart people think he's amazing and normal people think he's amazing it's because of how much soul that he was able to bring to the stuff that he was putting out I've always really admired that in you know in his writing I think James Clear has done an incredible job with that I think um Tim Ferris is like one of the ogs doing that
and that is a remarkable skill by the way it's very very difficult to do that and to hone that as a skill yeah I think that as a writer you need to have a brutal honesty with yourself when am I using a big word to posture and when am I using a big word because it's accurate and it's adding life to what I'm writing
and it's really easy to deceive yourself there this makes me think of status so my whole uh like my Razor for status if you will like how I cut through the noise on this is would you do this thing or would you buy this thing if you couldn't tell anyone in the world about it that's good and if the answer is no
it's just a BS status game that you're playing that doesn't mean you shouldn't still do it maybe you want to flex on the nice watch or you want to flex on the car or the private jet or whatever the thing is but just know that you're doing it for the flex you're doing it for the status you're not doing it for the utility the same exact rule applies
to writing are you writing that word because you want other people to be like wow David you're so smart or are you writing that word because it adds incremental utility to the sentence that you're putting out well also sometimes what you think is going to impress other people doesn't impress other people the funny thing is
now anti-status stuff is a status play like where you know billionaires or like multi-millionaires love to flex on the fact that they drive a shitty car like you'll see super rich people be like yeah I still drive my you know I still drive my Toyota yeah I still drive this you know like the whole thing with Warren Buffett the whole shtick of like he still lives
in his Omaha house don't worry about the 30 you know multi-million dollar Mansions he has all around the world or the fleet of jets uh he still got this car and eats at McDonald's so it sort of becomes like it's it's almost like you know the the inverse starts to become true too yeah but it is what game are
you playing with the writing that you're putting out into the world who are you trying to connect with who are you trying to impact and are you trying to sound smart or are you trying to create value for people every piece of writing is a call for the kind of person that you want to bring into your life that's how I think about it is what kinds of
people do I want to attract what is the writing that I need to attract those people and there's something about numbers on the internet that make people feel like they're all the same because you're looking at views you're looking at followers you're looking at likes but once you meet who your readers are in person you realize that they're just a
reflection of what you're putting out there I've always found it helpful to create things that I would actually want to consume and I consider myself reasonably smart at least on paper uh but I don't want to consume complicated sounding things that are super dense and super long I want to consume things that get
to the freaking Point yeah and get to it and then leave I like labor the point I mean my biggest lamentation about non-fiction as a category of books is that it is entirely filled by books that you get the point in 15 pages and then there's 185 pages of filler behind it and now having gone through a book process and
selling a book to Publishers I understand why because they want you to write the most narrow version of the topic that you want to write about like when I was going in talking about my book it's like oh well why don't you just pick one you know I wanted to have these five sections like why don't you just pick one of those and just do that
one thing and my whole point to them was that's not gonna that basically is g to be my exact thing that I hate about the book industry it's going to become a book where you could have gotten the point in 10 pages but now I'm giving it to you in 200 good luck go have fun with it and I don't want to do that I don't
want to spend two years of my life working on something that you know 85% of people aren't going to read or aren't going to enjoy or get value from and so that like I just I I often think that when I'm putting something out before I hit send would I want to read this would I get value from this yeah when I look at your email list growth there was a
huge uptick an inflection point in October 2022 what happened so there are two inflection points the first inflection point was when I met you so I'm going to give you I I'll give give you your flowers here I had never thought of email as something that mattered I didn't understand what the Creator economy was let's just be
totally honest around I was working in finance I thought that was the only way in the world to make money I thought that would be my entire life I started writing on Twitter because I had a bunch of time on my hands I was stuck at home I had no life it was during Co and that started to create traction there was something there I loved it I got tons of
energy out of it so I kept doing it but there was never a plan to like leave I didn't have some Grand strategy I didn't have like here's my approach to growing my Twitter Empire it was just I enjoyed it I was putting it out I started the email because people wanted to just see my Twitter threads in their inbox rather
than reading on Twitter our first call you encourag me to start taking email seriously and the value of creating that connection and that level of depth so that was uh like May of 2021 when I started taking it seriously and I started sending like on a real Cadence sending things out that was the first inflection point the second inflection
point was closer to the end of 2022 as you said um when I hired a team on the back end so up until that point I'd grown it to about 130 140,000 maybe subscribers which was fantastic but I was doing everything I was doing all of the writing obviously because that's what I enjoy most but then I was also doing all the business side of it like
my you know sponsor slots and uh you know any like collaboration posts with people and any uh you know promotional swaps with other writers that were in my similar domain all of that stuff I was doing and it was just an enormous cognitive load that was taking my mind away from the most important thing which was the creative work that I really
enjoyed it was like I was spending probably 80% of my time on things that I hated and 20% on the thing that I loved and I hired a team to actually go handle all of the like operations side of what the newsletter was so who's on that team what are the roles how did you define that the biggest thing was like I needed
a call it a chief of staff effectively um who could oversee all the operations I had worked with my the guy that had done my website for me um I knew really well because IID worked with him for a year is this Shane Shane yeah and we started talking started um explaining to him some of the headaches and some of the pain points with it I had become
really close with Nathan Barry the founder at convertkit we were talking about a bunch of this stuff and so then I told Shane like why I start paying you to manage all of this backend stuff to help me create you know basically like newsletter growth as a service effectively like all the backend stuff that I'm doing to try to manage and grow
the newsletter and what are the different parts of that like how would you map that out yeah so basic like blocking and tackling of we M we manually uh turn newsletters into a website version both for SEO and for it to exist in perpetuity somewhere in a beautiful way not just in a you know automatic landing page way all the
growth stuff so that would be if we run any ads for the newsletter that would be like swaps and collaboration posts uh you know anything now with all the convertkit tools around spark Loop or the Creator Network lead magnets like if you're going to put things out into the world like Tim Ferris was one of the first to do this he did it with like his
favorite books some of those things that drive email Subs in order to get access to some new insight from him things like that that I just wasn't going to have time to do or do well basically I would do them pretty poorly and I would be doing a bunch of things poorly but a lot of it was like let's test and learn
start doing some of these things let's see where it takes us so I hired Shane to start doing that and by January of 2023 we had just driven a dramatic inflection point in the growth you know from probably growing at I don't know 5 to 10,000 a month to 50,000 a month like a true 10x do you know what accounted for most of the
difference the lead magnets was a big jump um having a system around who we did uh collaborations and swaps with some of the tools that we implemented so with spark Loop that was rolling out that now convertkit has acquired at the time it was still independent starting to run paid ads and test what kind of CPA we could get around them and see
whether we could self-fund that with the ad Revenue that was coming in to make it just like a net Break Even thing basically just creating like an infinite Loop where all of the money coming in from sponsors was entirely reinvested I was in a fortunate position that none of the media or platform stuff I do is how
I make money so I don't do brand deals like you don't see me uh you know taking every brand deal that comes my way like I don't sell courses do those kind of things and I have a bunch of businesses that make money and so the newsletter I just said I'm going to run this at break even I want to reinvest every dollar that comes in from ad Revenue into
growing it so let's figure out how to do that Shane here's the Mandate figure out how we can grow the newsletter in a quality way I don't want to you know go and acquire a bunch of fake bot subscribers like let's assess learn figure out who's good what we can pay for them uh Etc so Shane started doing that we generated a lot of success and
by January I went to Nathan and I said you guys should have this at convertkit like this should be a service at convertkit and his response was Services isn't really what they want to get into convert kid as a software company that's what matters for growing the business and for valuation of the business if
they exit but that he was really interested in doing something like that so we actually decided to productize what Shane had done for me and we created and launched a business called paper boy that does this for other people now um so took all of the learnings from what he' done for me and created a product around it that now
it's like newsletter Ops and growth as a service that gets offered yeah it's funny I feel feel like the principles of writing are about as Timeless as it gets and I think the principles of distribution are about as timely as it gets yeah so what do you do as a Creator to stay on The Cutting Edge of distribution and how do you think about
that uh is it talking to other people and how's it changed over time as well yeah I'm constantly trying to learn best practices from other people what's working for them what's not working for them and that applies across all mediums by the way like newsletters one and it's probably my biggest Focus it's what I
get most excited about so I want to know like went deep on what did morning Brew do with their referral program how did they drive so much growth with a referral program in the early days just free effectively you know they're shirts and mugs and stuff but pretty free what are the best practices around paid ads because you can spend a lot of money and
generate a bunch of crappy Subs if you do that wrong you know what what's working around lead magnets like what does a quality lead magnet look like that people aren't just going to feel like you know they just got ripped off like they're actually going to start engaging with the newsletter because at the end of the day what you're actually
trying to do with all of this stuff is generate a quality connection with some new person and whether you pay $2 for that person or whether it's free through a lead magnet whatever what you actually care about is the like adjusted CPA which is adjusted for how much they engage if I get a150 CPA on someone but
they never opened my email that's infinite like I shouldn't have paid I shouldn't have paid anything for that and so I think a lot about adjusted where um you know I know there's going to be channels that areow lower engagement levels and I need to be very quick about pruning those subs from the list I need to be very quick about
testing if they're real and good and all of that is learned just by testing and iterating really really quickly by connecting with other creators having conversations with them what's working what's not and figuring out what I'm willing to do and what I'm not willing to do I'm not willing to write the really cringe uh you know TED Talks
thing or whatever it is even if I know that that's going to drive 5,000 email Subs I won't do it so it's also kind of like finding Within in the constraints of the type of content you are willing to create how has Twitter changed since you started dramatically yeah no kid um when you think about the trajectory of any Market I think Twitter has followed
the exact same thing which is something appears that is a massive Arbitrage and opportunity and the market exploits that opportunity until it no longer exists and when I started writing on Twitter which was May of 20 May 12th 2020 was my first post uh 500 followers out there at the time which is funny to think today
no one had really started writing in the thread format it wasn't enabled even as a feature you had to comment under your own post there was no like add tweet or create a thread where you could post it at once I started doing that because I was interested in exploring ideas in a depth that went beyond at the time 140
characters and it seemed like a good way to do that my second Insight which happened very quickly was from Reading Ben Thompson who I don't know if you've had on here but eventually I'm sure will who has this incredible model with his newsletter blog where he's embedding and like networking ideas unbelievably well David
senra does it with the founders podcast where he's pulling in oh yeah I talked about this on episode blah blah blah and here's how it connects I figured there was an opportunity to do that with Twitter where no one had done that where I could build on ideas that I had written about previously by casing them
back into a new idea that I was sharing and basically create a Twitter native blog and I started doing that and experienced rapid dramatic success without sacrificing my values around what the quality should be I did I never I mean I still feel really proud of this like I never did the uh the like true growth hacky stuff I there were things I did
that were more growth focused but I never did like whatever the trend of the day was around a post but that was the real insight for me was just uh how can I tie together ideas uh in like a meta thread basically where you're connecting to something you had written previously and bringing them together to create a really beautiful consumable piece of
content on a platform that was known for the little bite-size things I started doing that I was probably one of the first grew really quickly all of a sudden the market starts to pick up on an Arbitrage right so more people started writing threads more people started picking up on it com into 2021 threads become like the meme where every
you know everyone and their mother is writing threads most of them unfortunately um are bad because in any Market most of the stuff that is going to come out is bad for me it was great because if you're still spending time and you have unique insights and a different you can always still stand out within a market but for a lot of people
it became harder to grow from the thing the market opportuni started getting squeezed and squeezed out fast forward to then Elon Musk takes over a lot has changed since then personally I think for the better I'm really excited about all of the new features that are rolling out the focus on video how quickly
they're shipping new features and changes I think it's a much more challenging time if you're starting out to grow quickly and I think that's a good thing and the reason I think it's a good thing is I think focus on vanity metrics dilutes the quality of what you're doing you are much much better off having 10,000 people that are truly
connected with you because you've created really high value stuff over a year than by reaching a 100,000 people by posting about TED Talks so Kevin Kelly's thousand true fans is like the Bible of this right it's really really true and yet we all still fall victim to this vanity metric mindset so what I've been encouraging anyone that's getting
started now with Twitter that's or that had experienced the rapid growth and is now so frustrated is you just need to completely shift your mindset if you're talking about a thousand true fans why is it your goal to hit a billion people how do you square those two things that's a good question what I want to do is maximum reach that number of people
but create a depth of connection with as high of a possible percentage of them as possible I told you before we came on my number one Initiative for 2024 is to do in-person Live Events where I can create those 15th century Florence rooms for as many people as possible I a big believer that I have benefited dramatically from
being in those rooms and having access to those rooms over the entirety of my life most people never have access to those rooms and I think I'm in a position where I can go and create them so I want to go out into the world and reach as many people as I can with my content and then pull as many people of those as I can into those rooms so that
they can benefit from being around these you know these others and like big thinkers ambitious people because I've seen the benefit that that creates in your life and I know that I can be a part of that slight uptick that slight inflection point in other people's lives one of the strange things about creating
content is that often people read things that you've written that you now disagree with that hold you to those things I was talking to a friend of mine she's a Hollywood actress named Jennifer Morrison and she was uh she was in house and uh she was what Emma Swan played that character and she was one time
walking in New York and someone came up to her and like jumped on her and was like I love this character that you played like 10 years ago and she's like that was me 10 years ago like I'm so different from now and I think that there's this weird way that time shows up when you're riding and when you're sharing your ideas because you're like a
river you're in a state of constant flux constant change constant Seasons but there's something that is set in stone about writing and I find the justos between those two things to be a little spooky actually do you have any idea how long this is actually a genuine question do you have any idea how long it took to
paint the cinee chapel way too long I don't know the reason I asked is because I encountered this exact thing with writing my book you know it took a year say to put together like a d a first draft that I'm reasonably happy with and at the end of that year when I was going through and editing some of the stuff and trimming things down I read things
that I had written nine months ago at the very outset that I was like disgusted by the quality of cringed at like oh my God like who is that that wrote that thing from so long ago and with writing it's kind of funny right you like click delete you change it you make you know rewrite it whatever but imagine painting something that takes
five years to go paint and I think uh I think he didn't allow people to come in and look at it during the process because he didn't want any of any outside perspectives but I imagine when you're creating some massive Masterpiece you're going to go back to things you created at the very beginning of it and you are a totally different person you
have different perspectives on the world different vision for it than what you created at the beginning no matter what you have changed fundamentally from whatever you know systems whatever things have come into your life whatever challenges struggles Devastation whatever um you are fundamentally different and it's a sad thing that we
live in a world where we call people who change their mind in the face of new information flip-floppers it's a negative term politicians who change their mind on something are flip-floppers when in reality the ability to change your mind when faced with new evidence or information is a sign of intelligence that's First Rate
intelligence there's a quote on that but we say that those people or bad you're supposed to just have the same opinion for your whole life I think in order to be a good politician which is ludicrous yeah well I think that this is one thing that is really good about the time and the energy and the dedication that it
takes to write a book is that a book is what persists after all the day-to-day turmoil has been sort of scruffed away and you just look at at my core what do I believe I think that that's what a book is I think that's when you're ready to publish a book one of the biggest challenges I have faced is the transition from being primarily like
social media newsletter to book a lot of these writers they wrote the book and then you know became a big figure and continued some of them I guess were like massive bloggers and so they've probably encountered this but I'm not sure if they talked about it so I'll frame it for you the dopamine cycle is the biggest challenge to going
and writing a book that I've encountered every single other piece of content I've ever created in my whole life had at most a like 2day dopamine cycle meaning from the time I created it and thought about it to the time I got a feedback a hit of dopamine whether it's in the form of likes or retweets or whether it's in the form of responses to the email at
most like two days and take a book and it's two years yeah it's literally too I I am not going to get a single piece of like real live feedback on sales you know how people are talking about it reviews whatever for two years and so the motivation on a daily basis to go and really crawl through the mud to create the thing is so challenging and
no one prepares you for it you don't think about that that that is going to be the biggest challenge you face is that you are in the dark for so much longer than you ever have been in other endeavors within the creative realm yeah how have you thought about structuring time in a schedule in order order for
you to make the incremental progress there then I was terrible about it for the first nine months of the one year so I signed the book deal September 30th 2022 uh had in the original contract at least until September 30th 2023 has an author ever hit their original deadline I didn't and I didn't uh no and that that's a bad thing by the way because I
knew that because every author friend I'd talked to I'd talked to James Clear I'd talked to you know Mark Manson Tim far like all these guys that I really admire i' asked you know and they all said like oh yeah it took me three years to write the first thing or Susan Kane I talked to and she was like I write one
book a decade like if I'm lucky I'll get it done in 10 years so then in your mind you're like oh this deadline's a joke uh so you don't take it seriously just at the outset like you're not taking it seriously and so what happened to me was I basically spent nine months and I had written I don't know 5,000 words on the book which had to be 75,000 full
manuscript uh and then July 1st came around and I basically was like I'm kind of I'm the type of person that hits deadlines like I think of that identify as someone that I don't miss deadlines at least not without a full effort towards it if I missed the deadline I want to have like really given it my all and then I miss
it and so starting July first I decided that the way I was going to do it was that I was going to without fail non-negotiable have two hours a day first thing in the morning which is when my most creative moments are to write and I did that every single from July 1st until September 30th and I got it done um and I needed that like I just
needed to create the structure and create the time pressure and you hear authors talk about this all the time I had lunch with Mark Manson recently and he talks about this like you know he had written 10,000 words and then in the last month he wrote you went to like a cabin in the woods or something and wrote 100,000 words uh Matthew mccon
talks about this with green lights he did the exact same thing so it it's Parkinson's law for sure like the work expands to fill the time allotted for its completion uh I also again come back to what we said at the very beginning that the constraint breeds creativity once you're constrained and you know you have this window and you know you have
to really push hard all of a sudden things just start flowing how will you know if the book is good enough to publish and I'm terrified about this because I don't consider myself an author what I mean is my my future vision for my life is not an author um I don't know if I will ever write another book as long as I live I
try not to plan to far in advance in general in life I didn't seek out to write a book this book was the idea that consumed me and I I all of a sudden I needed to create it I had been getting approached by Publishers for 18 months prior to having this idea to write this book and I just said nope NOP nope don't have
anything they were coming to me with ideas hey you should write about whatever viral TW Twitter thread I had written you should expand that into a book it would be a great book you could sell X copies sure I probably could but I don't want to write it I don't I don't care enough about the thing or whatever it's not consuming me I don't feel like
I need to go Sprint down that path the yellow brick road to get to the to get to the castle and then I had this one and I felt that and so what that means for me is that I don't know if this this might be the only book I write in my entire life and that creates such a high bar in my mind for what I want it to be
and that's terrifying to me because it also means that I'm creating unbelievably unrealistic and high expectations for what I assume it is going to do in the world and that's what I'm most scared of I'm most scared of putting something out into the world that doesn't actually impact people in the way that I wanted to and I don't
know that there's a way to get around that where I've come to on it is there's two sides to it one is if this goes really poorly and no one b it no one's really impacted by it I want to have loved writing it truly loved writing it and being involved in it because I will have spent two years of my life or three years of my life on
something that is terrible and doesn't impact anyone if it is fantastic and it changes the world and sells 10 million copies I'm GNA have to talk about this book for the rest of my freaking life so again I better have damn loved the topic because I'm going to have to talk about it for the rest of my life and so in both cases what that distills
down to is feeling that connection with the idea and feeling that true guttural yeah explosion of what it is inside you I had a conversation with a very dear friend and at the time I was just really struggling creatively and I was like I want to be a creative lion I want to publish all the time and write great stuff and he's like
hold on on there Cowboy when you did feel that what was going through your head what was inspiring you to write and I sort of just lightened up and I was like you know this is what it was I'd get really interested in an idea and then I'd try to figure out that idea for myself and then I'd just go share it with other people and i' just do that
again and again and again and again with no regard for how successful that idea was going to be and it was like a 100b vest just lifted off my shoulders and I was liberated to just go run and create and I always think of that conversation because how much of writer block comes down to a deep fear of expectations and
being imprisoned by your own vision of how successful something needs to be that you can't actually let the sludge come out of you that then you fix later on because you're St starting with expectations it's 100% true and in my own experience it applies across everything it applies to the broader longer creative works like books it also
applies to how you think about social media and posting and the obsession with the metrics on how a post does it's inversely correlated to the soul that is in that work if you are constantly thinking about the number of likes that a post is going to get you're not going to create the things that you want to create you won't and I have I have
wrestled with that a ton to the point where now I do not look at the engagement on a post until 24 hours later is that right that was the change I made in my life and it has dramatically improved my happiness and the quality of the things I'm putting out into the world I will not look I will comment under things I'll reply to
people's comments and I'll like glaze my eyes over so that I can't see the performance of a post same thing with newsletters I don't look at open rates until a week later because I don't want I don't want to feel dissatisfied with something that I loved writing because the open rate is 5% lower than I think it should be at a point in time I don't
want that to go impact my day I don't want it to impact the next piece that I write I want it to be pure and I want to be driven by the right thing and that has really changed how I've thought about creating I want to create things again that I want to consume I want to create around real experiences that I'm
having and if there's there's Pro you know I have a million followers on Twitter if I go and have interesting conversation with someone super random interesting crazy I learned a few interesting things and I post about that there's probably not a million people that want to engage with that there's a million people that will want to engage
with some random you know uh platitude that I could put out you know and say like you making money like you know get smarter make money whatever like probably get a million likes on something like that but I don't want to do that I don't want to do that my whole life and spend I can't do that for the next 30 years of my life it sounds
boring it sounds miserable so separating like truly creating space between yourself and what you think the like output focus is supposed to be is really important and I'm I need to do that with the book and it's going to be really really hard what's your editing process like generally on anything mhm um very very light usually most
things that I create um what matters to you the shortest possible version of how I could say something the shortest yeah and I shouldn't I mean you know it's like the most concise version of how I could how I could get an idea across if there's like extra words and extra commas and you know all of any like uh anything that's adding fluff to
something that could have been distilled further um I try to strip out it's the reason that for the longest time I wrote Things First on Twitter and then expanded on them elsewhere because that forces you to have the most distilled version of the idea then you can expand on it and it's going to be much better
um when I get away from that the writing is worse like when I write it in the long form and then I try to distill it it's wor yeah we have an idea and write a passage called the shiny dime you got to find your shiny dime and it's just always a um a reminder to just find that shiny Essence that the smallest thing that you're trying to say because when
you know what that main point is everything else orbit orbits around it it's like a a song right every verse points back to the chorus and until you have that Clarity I think it's hard to write really well now sometimes that shiny dime comes to you before you start writing where you have a nice on lineer you have a nice phrase you have a nice
sentence where you're like that is the essence of what I'm trying to say but I find more often than not it's actually the opposite I throw a bunch of sludge onto the page and it's only in the process of removing of trying to find the needle and the Hast stack so to speak that then later I stumble upon what that thing is and often it takes me
years I have had that exact same experience you have to crawl through the mud in order to find the shiny dime I had this one line um I write a lot about this idea of finding enough in your life yeah the definition is of enough and I crawled through the mud on a piece about this for several weeks and then one
morning I woke up with this thing in my mind of never let the Quest for more distract you from the beauty of enough and I was like oh my God like it synthesized the entire piece into this one sentence for me and now I I say it like there's a lot of people that have you know taken it and it's turned into a thing um but it took weeks for me to all
of a sudden have this one moment where it was like oh more and enough and the ju deposition of these ideas you and I are very similar the way that we talk about ideas you just did it sort of had a shake when you talked about finding that sentence like the truth lies in the body and it's like for both you and I
the body knows and then the head almost receives what the body already knows and I've noticed that multiple times maybe it's an athletic thing it might be have you heard of the centipedes dilemma I have no idea what that is it's exactly this great so the centipedes dilemma is there's a story of a a centipede and a rabbit walks up to the centipede and
says hey which one of your legs is the fastest and the centi starts thinking about oh which leg is the fastest and is completely unable to walk anymore because they're thinking about which leg is the fastest and previously it was this intuitive motion of just like everything flowing together and the second they like threw a kink into it of
trying to think about it it shuts their entire thing down I've believed that to be true in almost anything that I've pursued in life as soon as you start making something a thoughtful process rather than allowing it to flow you lose all ability to like coordinate the beauty around it and so with writing it's the
Reason by the way that I avoid a lot of Technology as it comes to writing I I'm probably on the crazy end of the spectrum but like I carry around a notebook this is how I track all my ideas I don't have notion I don't like do note taking on notion or Rome or any of these fancy networked not take it's literally on a DOT piece of paper mol
skin pocket notebook I don't use uh you know any like chat GPT AI tools to research things like when I'm researching it's very analog and I'm going and looking at things when I edit stuff I print it out on paper and I sit there with a pen and edit it by hand because I have to see it on paper in order to actually like register the
words I can't see it on a screen so everything I do is like I'm trying to maintain a level of almost like childishness around it rather than making it feel like this big technological uh you know thoughtful process nice will you walk me through one of the pages on that I want to get a sense for the messiness the sense of the
play like what are you actually writing down are they fragments are they words are they complete ideas they images so here's like I you're not going to be able to zoom in enough I use a DOT um it's a Dot Plot to like a grid I don't like lines again lines like keep you writing within lines on dot plots I can kind of be like all over the place with
stuff and I'm a terrible artist so I don't try to draw things but here's an example like on one day I wrote current tension and this is just like randomly during the day I think I was out on a walk and I stopped and wrote this down um planning out I need yeah I just say planning out week ahead on weekly call
actually now even thinking back on this no idea what that was talking about like I just had that thought wrote it into my mind more barriers to my time and so for that one it was like too many people have too much access to my time that I'm allowing to just drain my time in different ways 10 minutes here 10 minutes there and then I wrote down
action points like what am I going to do about these different things there's a an interview with Kendrick Lamar where he's talking about his writing process and this is what he does he carries around a little notebook and it's one word here three words there five words there and for him it's a little different what he says he's
trying to write is an observation just enough that he can go back and find the emotion that he had when he was writing when he wrote that down and the way that memory works this is an intuitive like I got no science behind this but I almost think of memory as hiding inside of doors and it's very dependent on context and the
environment so once you open one door it's like other memories are sort of locked behind that and the reason I feel this way is you ever go back to your childhood home or you go back to your high school you go back to your middle school all of a sudden all those memories get unlocked but like those memories are almost hiding behind the
door of that place I have a very weird memory um I've never thought of myself as having a good memory and then recently I've had a bunch of friends say to me like dude you have a crazy memory on these things it's because I write stuff down yeah and when I write something down once like an idea yeah I remember it basically forever me too and
like even so from this conversation I have this one page of things that I've written down since we sat down and I wrote down excavation in quotes because you talked about excavation I was like oh that's a really interesting way of think about I wrote down poor equal soul from when you were talking about like
the starving artist thing so it's funny like all these these tiny little seeds that I'll then I'll write it down and then what I try to do is my rule with when I'm writing things down like a new idea that I write down that I've um that I've researched or that I've read something about I write it down my rule is that within 24 hours I need to act on
that note and what I mean by Acton is I need to talk about it with someone I need to go have a conversation try to explain it to someone ask them a question about how it connected with them whether I was missing something like see how they uh interact with the idea and then I remember it forever like that thees of my lus thees of my lus um
I read that like I don't know two days ago or something on the plane flight and I wrote it down and then I on a phone call with my wife brought it up and I kind of imediately get to see okay what parts of this story are connecting with someone what parts are missing how like how was I distilling the gist of it well
or not well one of the things I pride myself on that I try to do in writing as well as in any interactions on podcasts whatever is bringing the essence of an idea very quickly and concisely to somebody something that might have taken a long time to bring across like a long article whatever can you bring it in
like two sentences or three sentences and that only comes from doing this like write it down try to distill it to someone see where it took you a long time see where you didn't make sense or where they were like looking confused and then go from there you remember it forever yeah I call this writing from conversation where what you're doing is
you're talking to people and you're getting a sense for what's Landing what's not Landing what are the questions that people are asking and then over time you can just see it in somebody's eyes when that idea is ready to hit publish I remember there was a piece that I wrote many years ago called what the hell is going on and I was
working through the thesis and I was like I'm only going to publish this piece when I talk to like five people in a row whose eyes open up super wide as I explained it to them and I remember I was at dinner with my friend Drew Austin on the East Village in New York City writes a newslet newsletter called kneeling bus and I remember his reaction I was
like it's ready to I've been working on it for months and I just watched his reaction was like my fifth one in a row I was like it's ready to go it's so funny because my dad so my dad is a professor and I asked him what he enjoyed most about it and what he said was he enjoys the look in someone's eyes when they understand the
thing that he is presenting to them like that look where he can feel the aha moment when it connected with them in that way and I thought that was so interesting because it's not an internal thing anymore it's your ability to actually spread to like breathe life behind this idea into other people where you're like Inception of the idea into
someone else you see it in their face you and I have this deeply which is a need to share with other people I thought everybody was like this I have friends who they just figure something out for themselves and they're totally Gucci deeply fulfilled they're deeply fulfilled for me the Fulfillment doesn't happen until I share it sharing is where
the Fulfillment comes I wonder why that is I wonder what that is like a personality trait or personality type that creates that need for uh the connection in order to feel the Fulfillment around it yeah but I I mean I benefited dramatically from being around storytelling family and culture and I feel so grateful for that by the
way that got really lucky with a set of circumstances where covid hit I was writing things took off it was the right time you know I had that conversation with a friend that sparked me to quit my job that led to me moving back to the e Coast that you know my wife and I were fortunate to get pregnant with our son
that changed how I thought about the world like all of these things along the way that it's so much craziness that somehow led to me feeling this really deep sense of fulfillment that I get to have a conversation like this and call it work I mean you you you must feel crazy getting to do things like this I mean it is the most unbelievable
privilege in the world earned privilege but the most unbelievable privilege in the world to get to do something like this on a Saturday morning and call it work yeah amen amen I mean the thing that I think is very hard is to have the people in your life who can help you figure out what it is that you're actually gifted at that's the
first thing and then the second is to have the courage to say this is something I would like to be gifted at but I'm not gifted at that and then once you find those two things to then be able to chase the things that are unique and that are true to your gifts and lack of gifts instead of the expectations of your parents and of your
friends and of society and of the media to do something that is unique and distinct instead of doing what I feel like how you are feeling working in private equity which is far more standard coming out of a place like Stanford than being an online creator we also live in the most amazing time in history to do this you know the the walls of
credentialism are permanently cracked and being torn down on a daily basis and you can create credibility around something without having to go get a $200,000 degree James Clear is not credible to talk about habits because he has a degree in science from some University he's credible to talk about habits because he built an audience of a
million people that followed him for ideas advice and science on habits prior to him selling a book that has sold 10 million copies on habits it's not because he has a degree from somewhere he's some like 80-year-old doctor that's been studying habits his whole life which previously was the thing and I'm sure he got
along the way from people who said like why are you credible to talk about habits so I saw someone tweet at me the other day um that someone like I I often I basically read anything that people send at me cuz I try to to respond to things and especially the criticisms because I'm curious like okay what's the negative feedback what is it like what's
the essence of this and someone said it was an older uh older woman said she was tired of my shtick I yeah that was what she said she was tired of my shtick and I we should do like a read Mean Tweets thing it'd be funny but she said she was tired of my shtick and that I have no credibility to talk about uh to talk
about goal setting or uh achievement and I got the biggest laugh of my entire life about it uh she said goal setting and fitness those were the two things that I didn't have credibility in her mind to talk about and I got such a good laugh out of it and I repli I sent her a DM so I didn't reply public I sent her a DM and I just said I really appreciate
the the the feedback and the cander but I so dramatically disagree with that because literally all I've been doing my entire life is setting goals and achieving them around Sports and Fitness like those are actually if there are two things in my life that I am credible to talk about it's that like I'm not
credible maybe to talk about a lot of other things but those are two of like the things I'm most credible because I've been doing it so I don't need a degree yeah I don't need a degree in goal setting I don't need to have written a book on goal setting I don't need you know a bunch of like scientists to say that I'm the goal setting Guru
I've literally been living that and I have proof like I have stats to show that I have done that my entire life that I can give you if you want to see them and a lot of people read the things and have created goals and achieved them around those things based on the ideas that I've shared so I don't need the degree I don't need those things there's
proof in the entire world both from myself and from people that have engaged with it to do that and so my point with that is we live in an amazing time where you can create your own credibility without going to school without getting the degree without being 80 years old and having spent your entire life and a
you create it by what you're putting out into the world mhm what's your credibility read my stuff yeah read it there's my credibility is that there's a million people that read and benefit from the stuff that I'm giving them on those exact topics and the market will tell you if I'm no longer credible because they won't get value from it and
if they're not getting value from it then no I'm not credible and I'll tell you that I'm not credible to talk about it I'm not credible to talk about a whole lot of things but you don't see me write about them then sorry that gets me fired up we're done baby it was great to finally meet you that was fun that was awesome