Alex Lieberman — On Voice, Unicorns & Intrinsic Motivation | Episode 192

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[Music] the big unlock of our business and especially our newsletters is we're basically looking for a unicorn every time 5 to 7,000 filled out forms of that application there have only ever been 12 people that we thought could actually touch the newsletter to run a company you have to be self-aware every time I have a business idea that I think is somewhat interesting I put it out on

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social if my risk is one out of you know 500,000 people following me are going to do that I'm willing to go along that risk every every single day if we don't have any competitors like in 12 to 18 months we're we're in the wrong Market yeah if you can cover your name and replace it with any other person's name it probably means that it's not high specificity enough and it doesn't pull

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from enough lived experience what is the cost of you not believing in yourself of you not believing you have the tools to create any outcome you want to create you're the author here you get to write a whole different story if you want to well hello everyone it's Jim o shaas with yet another infinite Loops I have been looking forward to talking to today's guest for a very long time I

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think we will have a lot to talk about and we have a lot of shared Vibes I would call them my guest today is Alex liman the founder and former CEO of morning through and he also has a new company story art which we're going to talk about in a minute uh Alex man I I like I love you I love you too thanks so much for having me y you know you your path to me was just so cool and interesting because it

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it highlights a lot of things that I often when I'm giving advice to people and you know about writing write for yourself write for one person uh do it in an entertaining Manner and and you do all of that and more if you wouldn't mind for the very very few of our listeners and Watchers who don't know about morning Brew can can you give us the origin story because I think it's so

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cool yeah absolutely well thanks again for having me pumped to do this um one thing I will say about origin stories that are very interesting is you say them so many times that uh your memory of the story or me your memory of the origin is the story you've told versus the origin so I I cannot confirm nor deny if this is the actual origin of morning Brew because I've now repeated a

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thousand times and I may just be saying the story but my memory of morning Brew is you know at the University of Michigan I went to Michigan quick context on my background um I went to Michigan after growing up in a suburb of New Jersey um and I went to a private school in New Jersey from third grade to 12th grade uh didn't like my uh private school experience much and I wanted

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something very different Michigan was about as different as it got I was the first person in seven years to go to Michigan and I always dreamed of working on Wall Street uh I come from a Wall Street family my dad was a mortgage Trader for City Group my mom was ran the repo desk at namora my grandpa ran fixed income at credential so like I didn't know anything other than Wall Street and

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uh it's funny because growing up my dream was to be the world's greatest traiter I had no idea what that meant I just knew I wanted to be like my mom and dad and so the Michigan path was very much just the next step on this journey to reach that Pinnacle so I was in the business school at Michigan did the classic internship thing after each year after my junior year of college I

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interned for Morgan Stanley interned on the agency mortgage back security trading desk I got a job offer so I got into my senior year at Michigan have my job lined up that I was going to do after college had all this free time and basically I was spending way too much of my time playing FIFA or NHL on Xbox and I was like I need to do something to keep my brain sharp for when I go uh back to the

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trading desk and I started writing a daily business newsletter partially driven my by my desire to not basically lose all of my knowledge around the markets and the other reason was I was helping students prepare for job interviews I would always ask them how do you keep up with the business world every student would say I read the wall Journal but it's dense it's dry my

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parents told me to do it so I do it and I was writing this newsletter the original newsletter was not called morning Brew it was called market corner it was a PDF that I would put together every day so I'd literally go to Microsoft Word I'd go to the template Builder I'd select a newsletter template I'd write the thing it would take me four hours a day there was no logo for the company I ripped off a logo from

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Google of a baron a bull fighting that still had the water mark going across and there was no website you you were incapable of signing up if you wanted to sign up for the newsletter you have to reach out to me personally and say hey Alex can you punch in my email address to your list sered so that's what I did by myself for two or three months yet it somehow worked uh after two or three

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months of doing it 300 or 400 people were subscribed which at the time was impressive to me because it was impossible to sign up for the thing I sent out an email to that list saying I'm thinking about taking this project a little bit more seriously does anyone want to help one of the first emails I got was from this guy named Austin Reef who uh was in the business school at

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Michigan was actually in the same fraternity as me but we didn't know each other and he was like yeah I'm interested in this I have ideas for how to make this thing better we met up in the business school and from the get-go I was just fascinated by Austin's brain like we could not be more different thinkers or at least our default setting for how we think is very different and

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so I brought Austin on basically after a week of talking as a co-founder for this thing that we didn't even think about as a business yet and I think that's the beauty of this thing is we didn't think about it as a business for basically a year and a half we launched the first morning brew as a proper email newsletter with a proper landing page in the beginning of 2015 which was my

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second semester senior year at Michigan Austin's sophomore year we launched the thing and then um you know how long eight years later NE here we are today what amazes me about it is it illustrates I think quite nicely uh the idea that you did that because you you wanted to do it it was you were interested in it you did you didn't think oh I'm G to you know do a startup

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and I'm going to get BCS defunded I'm G to do all no what she did was Jesus Christ and I too longtime reader of the Wall Street Journal it's gotten better than it used to be what when I started read I'm an old so I'm 63 what when I started reading the Wall Street Journal literally it Alex it was nothing but text and maybe if you got lucky a little line drawing and and it was to put it

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charitably dry totally and and one of the things that really appeals to me about you and your story is we are seeing this huge ship I call it the great reshuffle but like all the old playbooks they don't work anymore they're collapsing and things like morning Brew are taking advantage of that like Que there's a ton of people who want to know about business news right but they want

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to be entertained at the same time yep and and was that the secret sauce yeah so it's interesting it's funny when when I think about the Wall Street Journal for a while the the the way we would kind of frame in our brain how we would create morning Brew is you know for anyone who's listening if you pick up a physical Wall Street Journal what you'll always have is from page of the paper on

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the left side you'll have this yellow column that b basically is kind of like the highlights and we were like what if our newsletter was basically just the yellow column and it read like you're smart and sociable non- douchy friend was talking to you over drinks over a beer at home like that was kind of the the vibe and it's funny um we thought about voice from day one like the real

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thing was um we we we didn't know a lot about media at all and it was it was a blessing of all the things that we didn't know that we didn't know that's really what gave us the ability to build this business but from day one we basically said this has to read like your smart friend that's talking to you not like a robot that's spitting information at you and it it kind of

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naturally took that form because in the beginning I was writing the thing and it's so funny today that like I create content on the internet I build audience because I was a horrible writer growing up I was like I was actually horrific and so the fact that like writing is one of what one of the things I'm considered to be good at now is is kind of hilarious to me but I Austin and I would

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write this newsletter and we didn't know anything better than just writing like we spoke and I think the the big failure that a lot of writers have is they don't write like they speak they write like they're taught to write uh in journalism school or or whatever and then at some point Austin and I were like okay we're fine at this we're like a b or a B+ but we need to start spending our times on

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growth like actually getting more subscribers to the newsletter and we think there are people who could better execute on the writing this thing and so we set up this kind of crazy system when we were at Michigan and we used this system for probably two years before raising a little bit of money and hiring our first full-time writer and the system was we got college students who

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were subscribed to morning Brew who had some editorial experience to write uh stories for our newsletter so on any given day two or three people would write the stories of our newsletter and then we said to ourselves those are going to be pretty good but we need an editor so we found a guy who uh both was um wrote for the Michigan newspaper but also was working uh did internships in

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finance so knew the markets well he was basically our editor of Mor Bru so he would assign stories and then he would copy edit them but then the third piece that I don't think any companies had ever done or thought of at the time but this was just less like us linearly thinking about how do you add voice we said he's a good editor he'll get these pieces to flow well but there's still no

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voice how do we add voice and so Austin and I literally created a job to description of voice editor that was the name of the job and we went to Michigan and we found the one guy who could add voice to any story and it was a guy who was a uh double or he majored in business but he also was in The Improv troop at Michigan and we gave he basically would take every finished

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story for our newsletter for a year and a half straight and he would add voice to it and we codified what this voice is we literally described if morning Brew is a person how old are they what are their interests what do they do on weekends what's their go-to cocktail what are things they say versus don't say and this was his kind of um his key for being able to edit effectively and

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all of those college students in the early days they did it for free to get exposure in front of uh an existing audience and then the editor and the voice editor we gave I think like a point of equity to um in the early days of that business and then eventually we bought them out of it and I think one of the cool stories is one of those guys he literally paid for business school with

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just that point of equity from The Brew how cool how cool is that did did you ever find that uh there was somebody whose voice was so different like H how do you uh assess somebody's writing ability their voice did you find yourself going when you were getting adding writers to it did you have the voice in your head when you were reading what they were writing or were you happy

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with the voice editor being able to work his magic and yeah yeah so um I would say for the period of time where we're still part in some context I should have provided in the beginning is we we were part-time on it right while we were students at Michigan and then I graduated from Michigan and I worked actually on Wall Street trading mortgages for a year and then I quit my job and so basically from 2015 until

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September of 2016 the period where we were doing it part-time that's when we kind of had this system running and while we had the system I would say we were vetting college students for um being really good at being interested in what's happening in the business world and being able to synthesize it into the most important points of like why does this matter to me as a young business

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person and to write with some level of like what I would just call like strong writing chops like good sentence structure good flow Etc The Voice editor we kept the whole time now the hard part became when I quit my job in 2016 and we raised a small amount of funding we raised 750k from family and friends um and the first hire we made was a writer because Austin and I were like we

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need to we're not going to be the best writers of this we need to hire writer and we can't have this college system now that we're full-time finding a writer a a one full-time writer who could do all of these things was exceptionally difficult it was exceptionally like that is I think the big unlock of our business and especially our newsletters is we're basically looking for a unicorn every

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time and we we basic we still have the same process today which is we had a Google form where we'd say to someone pick uh one business news story that you think the modern business leader needs to know about in order to not be caught off guard in a conversation and synthesize uh that story into 150 to 200 words and write it with a voice that comes off as this smart and sociable

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friend having a conversation with another 20-some year old and I would say over the years we've probably gotten five to 7,000 uh filled out forms of that application there ever there have only ever been 12 people that we thought could actually touch the newsletter and and it's interesting we'll talk about in a little bit but with story ARB the same type of thing I've realized has happened

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which is it is literally like a one in a thousand selection process of writers um because it's so hard right you're looking for someone who's a just a a News Junkie someone who has great um writing chops but the the issue is is writing chops combined with voice is always very difficult because for example there's a lot of journalists that have great writing chops but

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unfortunately unfortunately voice has been trained out of them in J school so you need to find someone who writes with voice almost like a comedy writer or a late night TV writer but also has like the fundamentals of writing and by the way that's why in the early days of morning Brew one of the kind of like places we would do outbound uh Outreach for people to ask them if they want to

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apply for the job is we go to every comedy club in the US message them and say if you have any people who perform standup or improv here who are looking for roles like full-time jobs send them our job description and and so uh can you enumerate uh the Unicorn what are the characteristics of that unicorn out of all the thousands of applications that you got what were the consistent

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characteristics of the unicord you hired yeah so I'll describe to me what like a unicorn story looks like and then I'll describe what a unicorn candidate looks like so to me an exceptionally written story does a few things it has the the the slippery slope that if anyone's ever read like the ad week copywriting handbook which is to me the best book on both copyrighting but in some ways also

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sales because to me they're just different versions of Storytelling it has the slippery slip which means the first sentence hooks you into the second hooks you into the third and so on uh when I think about a great story a great morning Bru story or any great story for that matter it combines a few things it's high specificity so it is very good at painting a picture using specific

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examples specific numbers that push the story forward the the example that I always use for why High specificity is so important is I used to listen to How I built this a lot and the episode I will always remember is the story of Sarah Blakeley from Spanx because there's a story she tells in there where she just got into nean Marcus and she was so excited but they put her rack in

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the back left corner of the store where no one would see it every day for a 100 days she would go into the store take the rack put it by the cast register until on day 101 this the store employees were like maybe the general manager wants it to be here I will never forget that story because of how specific she was and it read like only Sarah could have told that story and so

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to me a great morning Brew story reads as if only the morning Brew logo could be associated with that story and no other company so high specificity is one uh writing that dances is two and you know one of the simplest ways to describe writing that dances is interesting word choice and sentence structure that um isn't picked to sound smart or sophisticated but it doesn't sound basic or something that has been

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read a billion times the second way that you make writing dance is sentence length variation there's a great example that David Perell has put out where he shows basically the same paragraph of writing one is written where every sentence this is the same length the second paragraph which has the same exact words but there's variation in sentence length and it reads completely

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differently and the final piece to grade morning Brew piece is at the end of the day it's not just about saying what is the story that's going on in the world right now so it's not just you know what what is the story about you know Tesla hitting its production numbers in Q4 it's like why should I actually give a [ __ ] as an inform professional and potentially an informed investor so

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that's how I think about creating a great story at the morning Brew level in terms of a great writer to be honest with you um I just think about who who are best writers we've had at morning Brew for a while and our managing editor his name's Neil uh he's been at the business for six years so he was our third employee ever and now he runs the entire newsletter team has writers who

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work alongside him and he actually is now the co-host of Our Daily Show that we launch and I think what makes Neil So exceptional is that he has the most insatiable curiosity for reading the internet and finding like weird and wonky things like I think about the reason he's so good at writing a story is not just because he writes the story but he weaves in other aspects

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of business culture that are just in his brain because he's in this always uh on consumption mode of what's happening in the world and the second thing to me is like he is just great at high specificity and high flow and just to kind of rounded out never was traditionally trained in writing never went to journalism school the only writing experience he ever had was writing for University of Maryland's

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newspaper and that was it that's wild because I I have found very similar things in writers that I really love to read um very very and you know it's a little known fact that newspaper men as they called them back in the day because there were very few newspaper women but most of them like their backstories were hysterical right some of them didn't even graduate high

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school virtually none of the greats like make and and others trained in classic journalist techniques it was it was like literally the really cool multi-interest person and and did did we like does journalism school just prank that Curiosity and that newness out of you yeah it's it's a good question um I don't know for sure since I didn't go to Jay school but I would say that I

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do think that for whatever it does it makes people right for themselves versus right for Their audience in a really interesting way now look I there are some journalists whose writing I absolutely love like you know I'm a huge fan of Barry Weiss writing I'm uh a huge fan of of other journalists as well but also again when I think of my favorite writers I think of like Ben Thompson I

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think of py mccormic I think of David Perell all of these people not traditionally trained um I think it is easier like the the easier path is to be a good writer who's wildly interested and interesting who becomes a better writer than an exceptional writer who's not deeply intellectually curious and interesting who tries to become more interesting or deeply intellectually curious yeah I I that is my own

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experience I I was lucky enough to uh have the Curiosity part uh weigh down uh but was not trained as a writer I was the editor of my high school newspaper and love to write but my wife was trained in journalism graduated Summa Kum La uh with the journalist degree and I'll always remember the first thing I wrote for publication I was trying to get Barons to publish a piece I wrote in

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the early 90s and and I wrote it and and I gave it to my wife and I said you look at this for me ples and like literally it came back and it was nothing but a sea of red and and it was like and then she hands it to me and she I look at it and I look at her and she just gets this little smile on her face I went so she goes so that is maybe the worst thing I've ever read in my life it

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is dry as dust it reads like an academic who failed being an academic what what is why should I be interested in anything you saying here and of course back then much thinner skin I I got so pissed we were on a train going into the City and literally got into this huge fight with me saying yeah you don't care about you know the domain knowledge that I'm trying to get across here and she's like no I honestly

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don't I I want you to tell me an interesting story and this doesn't do it rewrite this [ __ ] thing and give me something that I can actually work with L like literally I didn't speak to her for the rest of the train right that is incredible and know what's the most interesting thing is I think that like that is our natural way that is our natural way of uh communicating

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information information to people and I think it's taught out of us right like just even if this is a very meta example but if you were to just listen back to the last minute of our conversation the way that you just Illustrated this lesson of good writing to me was telling the story with your wife and it was a far better way for me to learn that lesson than you to actually like try to

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methodically and and kind of like it a scientifically break down what it looks like to tell a good story and so it's like it's in all of us it I believe it is taught out of us I agree and one of the things that it but it it actually helped me immensely because it kind of gave me the freedom to okay you're you know what Missy but I stopped being mad at her I said you you're right

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completely rewrote it uh gave it to her read it just came in still lots of red to be honest but it was essentially now now you made me care and she handed it to me and literally like most of her Corrections were much better than me and so that was the piece that I submitted ultimately got published it was the first piece I ever got published professionally um and and what what it

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taught me was you've got to thicken up your skin here buddy because if you're gonna write you are just inviting everyone to you know remember that you know the gift actually that is incredible totally actually to debt right totally and to be honest like the the thing I always say to you know this is a different context than morning Brew but when I'm talking to people who

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either are starting to write um you know internet essays or build a brand online I'm like the number one test really to know if you have written something that people are going to enjoy is like there's kind of two criteria it's one could a fifth grader understand this because I truly believe if you cannot write something for the fifth grade reading level um you're not explaining

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things simply enough which probably means you don't understand it well enough and I and the second thing I would say is if you can cover your name and replace it with any other person's name it probably means that it's not highp specificity enough and it doesn't pull from enough lived experience I love that rule I I I I didn't know that one so thank you I I will be instituting that all my writers that oy Ventures

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could to be delighted that one yeah but it'll be interesting like if you even do a test like go through your own um your own Twitter and kind of cover your name and ask yourself could someone else have written this I know if I do that for myself there are so many that the answer would be no someone else could have written this and I think it's a really good litmus test I agree uh on on the

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idea of finding that kind of unique unicorn we're supporters of David Carell's WR of Passage y uh we big Believers in like writing has never been more important not less and and so my question becomes is that something you can learn is that something you can train into somebody oh um I think that I think that um everyone can be taught to be better at writing so I

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believe that but I do believe there are certain innate abilities that have to live within you to be an exceptional writer so I think every good every person can be trained to be a good writer I think um there are uh born um traits that make people exceptional writers and I don't think everyone has them and I think honestly that goes for not just writing that goes for any

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career it's the way I think about it is like Morgan howel is an exceptional writer I do not believe that if Morgan howel Had didn't have certain qualities in him his way of thinking his way of um thinking about uh kind of like having this natural intuition around like the Arc of a story I don't believe that he would be an exceptional writer but also you look at Morgan hael and he wrote

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3,500 pieces when he was at mle fool so he put it basically I almost like the way that I view this is um if you if you had a hundred people uh in a in a lineup who wanted to be writers I view it as like there's a ceiling like like say like the the ceiling almost like if I'm looking at a like a player's baseball card and and the ceiling is like 100% that is the very best you could be I would say that

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each person on that line is going to have a ceiling and they're going to vary for some for a few it's 100% for some it's like 70% and I think it's the the amount of effort uh intentional effort um you put in and get you closest to your ceiling but I do believe people are born with 100% ceiling versus 70% ceiling yeah um I I fun story I tried to coach Morgan and come him come have him

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work for me before he was uh anointed as the sage of Seattle uh and and he quite intelligently turned me down it's like yeah no I'm very happy doing what I'm doing over here but you're right I think that like one of his gifts is to take something that you know just on just in the thought process or on the page kind like yeah okay I get that but then he flips it on you and and makes it like

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and kind of shocks you a little bit right in the in the way he puts the story together he he does that with public speaking as well which is a very interesting trait one of the things that I did uh so I've written four books but the book I'm best known for is what works on Wall Street which I intentionally wrote in a dry style why did you do that Jim I once was giving a

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speech right uh about what works on Wall Street and uh I give lots of examples to tell lots of stories and everything and a guy came up to me afterwards holding the book he looked at me and he was dead serious he goes you cannot be the same Jim oasi who wrote this [ __ ] book do you find so so why why did you do that why did you write it in that manner because I was such a data D of so

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many different things about what the book did was like everyone talks about hey Buy Low PE stocks or buy stocks with the best growth and I was sitting there in the early 90s saying where's the proof like I hear all these things I all these interviews with the asset managers they're saying the same thing but is there any empirical proof that that what they're saying actually is right or not

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and so that's how I got the idea for writing the book and because we were going to be covering so much I had to standardize right Y and and and to do that it put me in that drier legs that makes sense yeah but by the by the way one thing I would say to that is um we rote morning Brew in a very voicy way because we thought for the at the time the college student who's interested in

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business it is important for them but I think something to also keep in mind is like not all content is meant to be voicy like I look at content on the spec on kind of this spectrum of what percent information versus what percentage entertainment is it so let's say moring Brew is I'm just going to use number let's say it's um I don't know uh 70% information 30%

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entertainment um as we went into other newsletters so after morning Brew we branched off into industry specific newsletters like marketing Brew retail Brew etc for uh industry professionals and uh job functions and as we thought about let's just say retail Brew our calculist for voice changed for the audience so it became know what we're going to be 85% information 15%

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entertainment why because the person reading retail Brew first of all their reference point is existing uh retail trade Publications were L which are literally 100 and so we don't have to differentiate all that much to be very meaningful but also they're not coming to us necessarily to make themselves like smile and laugh a ton they want to get the information that helps them be better at their

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job yeah I agree and I was coming at it from a Wall Street very specific uh point of view right um and if you know anything about Wall Street you know most wall streeters are really funny and they are I mean to the point where like literally the first time I ever heard a joke was from a fellow wall streer and and I remember the day I'm moving out of one house into the next house and I'm

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packing up boxes and the and the uh space shuttle blowing up disaster happened and like I heard on the R I had a radio on and I heard on the radio like oh my God that's awful my phone rings and landline back then my friend there go I I I go I pick up the landline and it's a buddy on the street who says I said Bud like oh my God oh my God that is incredible Wall Street is the king and queen of too

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soon yes oh W without a doubt yeah it's um yeah to your point it's like uh there's a very specific type of humor by people that are working on trading desks or in investment Banks and it is the definition of mistime humor totally totally love that uh but but the but the idea was that it did get me thinking about like because I passionately agree with you and anything that I write that I really am happy with

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I'm writing it basically for myself let's be honest uh something I'm interested in and you can just tell like write this no interest like H right and it just it just bleeds off the page that you have no interest in what you're talking about and then when you add in the voice which I think is the right way to think about it it just comes alive you know Lulu mury uh who does PR I had

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her on podcast and like she is the queen of the hey [ __ ] face the world is a whole different place now you know corporate speak jargon Etc it it only people are just going to laugh at you I think about it like you know I'm sure you're familiar with the campaign that uh those wonderful people over the bu economic for are trying to do and like they're spending millions that they are

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so tone de so at odds with what regular people are thinking about these issues that I just I'm like to me it's they're spending hundreds of millions of dollars on Meme creation but not the memes that they want totally basic basically the opposite yeah I mean it is so interesting to me that like this is a recent phenomena because people have always been people so it's just such an

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interesting thing like culturally what's changed that people don't want to be spoken to or they now want to officially be spoken to like people versus 20 years ago when there were still people and wanted to be spoken to like people but I also think it brings up this question which is like you know you you have kind of very gracefully managed this balance of both like being a successful industry

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professional while creating content on the internet and building audience and I think it is not only wildly impressive but I'm sure you've seen like building audience has been probably very additive to your life and to your career and so I think people get very excited by that but you know um people come to me a lot of times and be like Alex you know I want to

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build my personal brand on the internet I've seen so many people do it I've seen people raise funds off of it I've seen it uh Drive customers how do I start doing it and honestly like the first question I always ask people is like do you enjoy doing it like do you actually enjoy creating content having your brain always kind of like scanning through ideas Etc because it is a muscle and it

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is a skill and it's like um I think about it like a different form of Entrepreneurship where if you don't like the thing it is going to be absolutely miserable to be a content creator for an extended period of time like you're not you're just not going to do it and and by the way like that's one of the ways that I figured out that creating content and building audience is something I can

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do for my whole career and that I'm pretty good at because often times it's really hard to know like your specific superpowers you'll know a few but sometimes you'll be blind to others because the best way to actually know your superpowers is you ask someone what are your thoughts on this skill set and when they basically say it is horrific like I was talking to a guy the other

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day and he's like there's two fears I have in the world one is skydiving and one is writing content on the internet that other people see you actually start to get a sense of do you like the thing and are you good at the thing because it just doesn't feel like that to you yeah I I immediately flashed on the uh Austin Powers thing where his dad is there and they they I can't this is the wrong

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quote but uh there are two things I can't stand in intolerance and the Dutch yes so good you just an absolute reference machine which also makes you a great writer like that you know going back before to what I was saying about Neil or writer at the brew and like kind of always being in culture and having like the inculture joke like that is a skill set in itself it's like know those

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things it's like why also I listen to like you know when I listen to Sam par and Shawn Pur it's like what I think makes Shawn a great co-host of that podcast is there's always some story or reference that other people will get especially oftentimes that like they've thought about themselves but it's never been stated out loud that I think is such um an incredible skill and one that

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is very hard to teach yeah and and some of that you know you mentioned Morgan writing all the pieces for the mly pool right so some of that just comes from duration as I said I'm an old I'm 63 so I have my my huge Advantage honestly is like I have 30 years more of cultural references than younger people right totally and and and that's a huge Advantage right because will they're

37:45

seeing it the first time and they love it totally but what I will say also is I think the hard thing that I think you've been able to bridge is a as you age keep keeping resonance with a young audience I think it's just diffic difficult right because you know I think about it for my for um my cousin's age she's like you know in um in high school and the way that high schoolers engag with content

38:10

today and like they're addicted to YouTube and a very specific way like that's not the way I ever grew up so it's like I need to somehow learn those habits and so I think to your point the fact that you have 30 years of stories but like you also understand like the meme that the the 30-year-old finds hilarious today is like the skillet itself yeah and uh that's on my list too it it's like

38:35

vonette said to John Irving when they were both teaching at the same very prestigious writer Colony I think in Iowa uh uh basically along the lines of something uh of course you could write in a serious tone but if you're going to write in a serious tone you better be [ __ ] entertaining too right and and I think I that really resonates with me though because like

39:00

honestly with the with the tsunami of stuff that's coming I mean wait it people who thought that was like a few years ago oh no my friend y the tsunami of information that's going to be coming is going to be just like on you know something we've never seen so you've got to have that edge whatever way you can find it and to your point I think think that the more you can make it about what

39:28

you naturally lean into something you say actually move towards things that energize you don't deplete their energy another thing you say you say a lot is basically good writers good CEOs to to run a company you have to be self-aware talk about that a little bit because the people that are the most fun to make fun of like again the folks at World economic Forum they're have zero

39:55

self-awareness least self-aware totally yeah I um you know what I always say is whether this is like a CEO that I I want to work with on a new company that I'm spinning up or a new hire that I'm making is I would way rather so if I if I could choose between two people um that I'm hiring into a job one person has let's say 90 95% relevant job experience like they've done 95% of the

40:24

job that I'm hiring them into but they are woefully unaware uh they are they don't know their blind spots they don't know what they're not good at they don't know what they should delegate towards because they think they're good at everything say the second person um is only at like 45% or 50% but they are incredibly self-aware I will hire vast majority of time the second person and my my reason is is at some

40:50

point the company you're building is going to grow outside of the person person A's competency so sure day one they've done 95% of the job but what about two years ago two years from now where they no longer can patter match everything and now their relevant skills are like 30% but they have no ability to grow into that 70% and so yeah like I mean I also I feel so grateful that I I

41:18

in my own career I've been able to identify like what are the one to three things that I love doing that I think I'm good at and I genuinely believe that everything other than those three things I can find someone else that is significantly better than me that enjoys the thing significantly more and I couldn't imagine a life in which I wasn't constantly looking for those

41:41

things to give to other people because honestly I would be the bottleneck to everything in my life um and so yeah I uh that is like probably number one for any like uh for story ARB um the CEO I brought on for any business uh that I start moving forward and I bring on a co-founder it's like basically when I ask the question of them I actually love asking the question like what are your biggest weaknesses

42:07

everyone hates that question because they're like people are going to use a fake weakness but I actually like to me if you can basically say if you if you tell me a fake weakness I'm actually going to view that as a weakness on your part because it tells me that you're not self-aware of your weaknesses I think things actually get very interesting I agree and like uh they

42:26

when I was briefly at be Sterns they let me interview intern potential intern candidates exactly one time because I think most interview processes actually lead to worse outcomes if you follow them Y and and like there's a joke I tell I use this joke as kind of a sorting mechanism right and and it's a guy uh who's got to figure out what interns to hire and his assistant brings

42:52

in uh 50 of their resumés and sets them on the table and the assistant says to him dude you got to get through these because you know they're due like at the end of the week and he looks at his assistant and he goes hey hey Jack and he goes yeah what he goes randomly pick 25 of those and throw them in the trash and Jack looks at him like are you crazy man these these people work so hard on

43:19

all of this you don't really want me to do that and he looks at him and he goes yeah I do because I'm lazy and I don't hiring unlucky people that is so absurd but yeah to your point I don't know what the business is but there there's something to do around how broken the interview process is like I've even thought about going back to like blind spots I've I realized in the early days of morning

43:43

brew that I had a very clear blind spot or bias in my uh way of interviewing meaning I would always interview and I'd have a better feeling towards people who had a similar uh personality to me people who are more extroverted who are very articulate people who like honestly would be known as the person who crushes an interview because they're a good Storyteller but there's actually an

44:06

irony to all this because actually potentially the best candidates are the ones that can't do that because if they've gotten a job in the past and they were a shitty interviewer it actually probably means their work is really good it's like when you're choosing between doctors and you're talking to two surgeons one is like this really good-looking guy who is a former

44:22

model has beautiful hands and the second guy is like a schlub who like you know you're like I would be afraid of this man holding a knife you actually probably should go with the second guy totally I actually had a surgery not too long ago and that's how I picked the surgery I'm like okay you're you're here which means you're amazing you don't really look the part I'm going with you

44:45

all day long exactly and and that was my first tire at the first company that I started with shy Capital Management I just had lunch with him yesterday great guy named Chris less but the reason I HED him he was good at everything I totally sucked at yeah right and it was just like I knew that I sucked that and like he checked the lit just all the way back totally and honestly that's what I

45:10

feel so like I really think the best decision um there were there were I think two decisions that are one uh rank one and two for the best decisions I ever made in morning Brew one was bringing out my co-founder Austin the second was firing myself out the CEO role and making Austin the CEO um and I think I feel so so like you know I think the skill in hiring Austin that I had

45:35

the little skill I had because it wasn't like a formal interview process we talked for a week like there were so many reasons that it could have been the wrong decision because I was not rigorous with it but the little skill was me just identifying what you talked about with Chris lovess which is Austin's brain was completely complimentary to mine I was the person who was always thinking in terms of the

45:57

next new idea how are we going to uh how are we going to uh sell investors on getting involved in the Brew how are we going to sell employees on joining The Brew how are we going to sell advertisers um like if you've ever uh studied the EOS process which is just like another version of okrs there's two people there's the Visionary and the integrator and I think people live

46:17

somewhere on the Spectrum but I like pretty squarely especially when we were starting the business sat in the Visionary category and Austin which I didn't have the language for this at the time Austin was the integrator like he was the most linear thinker I knew he had better uh just like clearer deep thinking than still anyone I've ever met like like I've met a lot of successful

46:40

entrepreneur I think he's still like top three of any entrepreneur I've ever met and um and so it was just like the way I always visualized it is like I'm just like this insane uh racehorse this Thoroughbred that's running around the track and Austin is the person who put the blinders around my eyes and he's the jockey who's making sure I don't run into the railing for half the

47:04

race and and that you know the the push back I've gotten on that is like Okay C can you com I'm talking about myself like yeah yeah Jim Jim will you like stop talking about the 24 things you just brought up in the last 15 minutes and can we maybe like like these three are interesting so you're right if you don't if you don't have that person like you're just a whirling dervish and and and you're

47:33

like God man and and like like you get you don't really get anything done that's another thing like persistence I think is uh something that's very admirable I I happen to be persistent but I like seeing that and people I'm working with and and the way we kind of pervert I guess the the old interview uh problem is we we we like to look at people as movies not as snapshots right

48:04

like a snapshot okay if it's a great snapshot oh let's hire this person wow they're so goodlooking and this is such a great picture but if the movie version of them you see the the before right and it's not so great the the idea of proof of work is that getting easier now is that easier I I was just talking to someone about this because I was just talking to um

48:30

actually a Founder who's a client of story ARB and he's building a really interesting business uh that's in BBS and one of the things he was talking about with me is just that um you know hiring is really difficult and hir like it um uh it's so easy to hire the wrong people and one thing that I said to him which is true is like I am trying whenever possible now to go from contractor to full-time

48:56

like whenever possible I basically hire someone as a contractor to work on an actual project within the business and after a month I feel like I have so much more clarity around if they're the person and they have so much more clarity of if we are the company so like for example I did that with the CEO of story ARB and and I think this can be done at any level like she was a

49:17

Contracting CEO for the business for a month and so I was like you're going to run this business as if you run the business for a month and after this month we'll learn one of two things either we were in a good fit for each other or you'll have this full-time CEO job but we'll have a lot of clarity around it and so I think that is something that I literally try to do as much as humanly possible the second

49:40

thing that you know maybe this is something that people don't agree with I like making interview processes intentionally long uh and and I just think going back to the point of persistence someone who really wants the job is is going to keep pushing through and also the longer you make the interview process the more you give them aperture into is this the type of work that I want to do or these the type of

50:04

people I want to talk to and so like I actually like making an interview process uncomfortably long and making people self- select themselves out yeah I think giving the opportunity for people to self- select out is key and you you've just also described oan C Ventures hiring process everyone starts out and we use eight weeks um but they're they're there on a trial basis

50:28

for eight weeks but for exactly the same reasons that you uh mentioned right it's like we might be a bad fit for them and it's like if you I've run lots of businesses and i' I've had to let a lot of people go and the thing that really surprised me was like in eight out of ten cases they knew they were wrong there right and some of them just kind of like took it as a relief and and

50:53

what's cool is you watch them go on to find where they fit much better and they do really really well and so this idea oh I got fired or you know that's not fair that's [ __ ] what you're doing if you're doing it this way you're giving people the opportunity to test you out as well yeah I think when I reflect on like within morning Brew what are the biggest mistakes that we made in

51:17

hiring or like what was the cause of the biggest mistakes I'd say one that comes to mind is having the wrong reference point and I think this is something that people don't talk about enough if someone is not doing a good job or like you let's say you have an employee who has grown beyond their depth like they've reached their ceiling within the business and so you're looking to hire

51:36

someone new to come into the business well the risk you run is M let's just say you require someone who's like an SVP level but your current person in the role is like a director level when you start interviewing VPS they're going to sound seem incredible Rel relative to the person you have now but you don't even have the awareness that maybe you need two tiers higher because anyone

52:01

relative to the person you currently have is going to seem exceptional again that's where I think like contract to full-time could be a valuable mechanism as well it's also where I think a valuable mechanism is you having awareness that maybe you have the wrong reference point and you either have an Advisory board or investors who have expertise in that area of the business

52:18

that you call in to the interview process to help you understand if your reference point is going to skew you and still hiring 2 Jun I think the other thing is a rushed hiring process where let's just say you have three candidates let's say you get to down to the final two but there's one who stands far above the rest you give that person an offer and they end up rejecting the offer

52:42

because they had another job and they go join that company and they're like oh it's fine we'll go to person number two because they were also in the process you hire that person you realize the Delta between your top one and them was actually huge and you just realize in an in an effort to close out this hiring process you've actually now set yourself back six months because it's going to

52:59

take you four months to realize they're not the right person and so um yeah it's very and but I also think like a lot of these things are just learned experience like I I also think I can say these things until someone's blew in the face but sometimes you just have to go through it make the mistake and you'll feel feel it so much more in your bones by doing that that brings up something

53:19

that I passionately believe and that is some of the best ways to do things and get things done you can Arbitrage all day long because you can shout them from the rooftops and unless you go through it unless you understand it intuitively it does not matter right exactly when I was publishing ww Wall Street I got a a large Investment Bank tried to buy my small company right but the the deal was

53:47

if we buy you you can't publish this book and and I'm like oh that's a do worked for so many levels right like you guys don't understand these aren't Trade Secrets here these are all Arbitrage opportunities we're arbitraging human nature here right exactly and and and it's so interesting to me that that that that dominant mindset still is dominant right like oh no proprietary secret yeah

54:20

it's why it's why to be honest with you it's like something that I just love doing is every time I have a business idea that I think is somewhat interesting I put it out on social right like I've if if you search there's so many times I've written free business idea and I put out an idea and the reason I do that is like I only look at it as net positive the net positive that

54:39

comes out of it is it creates interesting discussion around this idea or people who are already building it and maybe I can partner with them on it or invest in it and I don't have awareness around it already being created people say like the downside is oh someone's going to take the idea and build the thing but I think it goes back to like human nature which is okay let's

54:58

say there are of my whole audience there are 20 people who look at the idea and they're like oh my God Alex that's genius I've never thought about it I'm going to drop everything that I've I'm doing in my life right now and build the thing I think maybe of the 20 there are three or four people that actually have the tenacity to do the thing then I think of those three or four people

55:19

maybe there's one person who has both the skill set the knowledge and the tenacity and if my risk is one out of you know 500,000 people following me are going to do that I'm willing to go along that risk every single day me too and you know it's just amazing to me that uh more people don't act like that I mean when when we were uh we soldas the asset management Franklin Templeton we were

55:45

developing a thing called canvas which was kind of based on something that I had done earlier with thing called met folio but somebody said uh In the Heat of these negotiations right oh and we won't have any competitors and like that stopped me in my track so I went whoa whoa if we don't have any competitors like in 12 to 18 months we're wrong we're in the wrong Market yeah exactly

56:08

we're wrong totally and and this idea that you don't want competitors no God you're wrong if you don't have competitors right yeah I yeah it's so interesting by the way um I'm interested in how you navigate this you know something you mentioned before with something similar to I what I me which is like I have a bazillion ideas I'm like an idea machine but that can be

56:29

kind of jarring for a team or like if not put in the right structure it can be counterintuitive to what you want to do uh you know uh and we can we can talk about like but how I'm thinking about building like my next businesses and kind of my stage outside of the Brew is trying to kind of respect my creativity without holding me back how do you think about because like it sounds like you're

56:55

you're similar in that regard where you have a number of ideas how do you like not hold back your creativity and your ideation around new things you can do within your businesses but also not like how how do you not hold back that skill but also make sure that skill doesn't hold back what you want to do with your businesses one of that's a great question one of the things that I was

57:16

lucky enough to get taught when I was really young by my grandfather who's really successful was it's what he called premeditating and and by that what he was I get an idea and I I do this with ideas too and it's very helpful so you get an idea and then you basically premeditate what are all the things that might happen if this idea works right that are good but then you have another

57:40

line what are all the things that might happen if that are bad if this idea works and then you do it then you do it for the opposite as well right like are there good things that can come from me not for pursuing this idea totally right and and you find out and also you got to write it down you can't it's not like me and you just bullshitting back and forth together you gotta it's a process and

58:06

you got to do it in writing because that I think that's a different way of thinking uh basically and and so it it emerges very quickly when you're doing this process right oh I really don't have this is a bad idea this is that's a really bad idea and it's like the first 10 minutes and then so you scratch that one off the list but then as you continue let's say you get one that's

58:34

really good and it makes it all the way through then I toss it into slack or when we're getting together with teammates and like what does everybody think and totally it's it's very easy because again you know there's a certain type of person who might like that particular idea uh but what I what I really like in terms of pursuing I'll give you an example so we have uh

59:00

infinite media because we share a lot of your uh positions on where things are going right and and so we hadn't even thought about book publisher but all of a sudden it started to be like well duh you know we should probably be in the book publishing uh business as well what was great about it is did the premeditation it really really well of course you idiot it's like slapping me across the face

59:29

why didn't you think they should have led with that Mr author uh but but then when you get when you get the positions from people are very different people but they all like it but bring very different things to it like I like it for this this and this and then all of a sudden like it's just like a magic business plan develops and yeah and and story ARB is a great example well one of

59:55

the things that we're going to offer through infinite books are we completely agree with you in terms of there are people with great stories great lessons great everything but they're too busy right yep not anymore we got writers we've got you know you you you want a book you want a substack you want a YouTube you want a podcast we could package all that up for you exactly and

1:00:20

by the way once you do that you can also launch a business off of the back of the audience that you've built for the person exactly exactly and and so one of the things that's what when I was uh preparing for you I was already excited because I love your stuff but I I've got a great researcher right and so like he finds things that I had found and and one of the things that you said that I

1:00:44

loved and I hadn't seen it until just earlier today you you want to be the co-founder but you don't want to be the CEO of any of explain that a little bit yeah well uh you tell me how deep you want to go into this because I think to if if I was to kind of tell the full story it would have to go back to my like me stepping out of my role as CEO of morning brew and kind of my

1:01:09

revelations in doing that you want me to talk about that I do yeah let's go deep I think that people can learn a lot from that okay so basically the long story short is um me stepping out of the CEO role at morning Brew was probably the hardest decision I've ever had to make in my life um and it was my emotional state for six to 12 months after making that move was probably the lowest I've ever

1:01:43

been in my life like honestly the the the only thing I would say Rivals that was fifth grade to 12th grade uh at my private school being bullied and going to school at every single day and not feeling safe like it's one of those two um and so I'll talk about how I felt and then um why I stepped out of the CEO role and what I learned from it the way I felt stepping out of the CEO role and by the

1:02:09

way I felt very alone in all of this because I never talked to other Founders who have stepped out of their business I had no idea uh I I I didn't feel like this was normal although I've now learned in uh many conversations with people that this is kind of like the most classic feeling that exited Founders have but I felt a few things I felt a loss of identity um I felt like I

1:02:31

didn't know who Alex liberman was outside of morning Brew uh the best analogy I can give for people who haven't experienced this feeling is if you can imagine what it's like for a um a professional football player who's played football literally since they were four years old uh play 10 years in the NFL they retire and then they they are like what do I do now what skills do

1:02:55

I have now Etc it's that feeling the second big thing that I think created um a really shitty emotional state is my motivation changed um I would say probably a year before I stepped out of the CEO role my motivation on a scale of 1 to 10 felt like a two which felt very uncomfortable for me given the first four or five years of morning Brew my motivation felt like a 12 out of 10 and

1:03:21

I wasn't sure why at the time I think as I examine it a lot of the the reason is the things that motivated me in the early years of morning Brew are were no longer going to be the things that motivate me moving forward um I was obviously motivated by kind of partially my love for the game and love for building with morning Brew but I think there were two extrinsic motivators that

1:03:43

played a huge role one was a desire to make a lot of money um and there are reasons for that one is you know uh I never knew kind of my family's financial situation I think because I didn't know that I had a lot of stories about that um the scarcity mindset around money the second is my dad passed away when I was a junior in college and I felt this obligation to take care of my family

1:04:06

whether rational or not so the first was money motivation and we got to a point in morning Brew Journey where I knew we were going to have some liquidity event at some point and money was there there was no longer motivation to make money because I knew it was coming the second was a desire to be liked a desire to feel belonging a desire to feel a part of something I think that comes from my feeling of

1:04:27

not being liked not feeling safe not feeling a part of anything basically for my entire formative years as a kid and to me building a business was like it was the fast track to do that Founders are respected you build this audience on social your business is doing well everyone's going to respect and like you and at some point I think I realized also like that wasn't filling my cup and

1:04:48

so imagine if those things are taking up 80% of my motivation those things deplete all of a sudden 80% of what drives me my motivation goes away the third thing that I think made me feel really unhappy after leaving the Brew is I question all of my skills I had this story of myself that I got very lucky that I was not skillful in building my company that my co-founder was dragging

1:05:12

me along for the eight years and so in leaving morning Brew my story to myself was the money I made from our exit was the only money I would ever make so I have to protect it at all costs and I no skills to actually do this again and I basically dealt with all those feelings for like 12 months um and I got to a few places um one a as I came out of this and by the way like if kind

1:05:40

of people are wondering how do you emerge from like this kind of valley of Despair I think one of the ways is it's probably a good time what that time in my life if you've ever felt that way it's probably a good time to uh to to seek help or support in some form whether it's peer support whether it's a therapist whether it's a coach Etc I did all the above during that period of time

1:06:06

but I think also time really is the best teacher like I felt so much emotion leaving the CEO role and I think time is the best way to De to separate emotion from from mind or emotion from like intuition and that just took months I ended up getting a place where I said to myself Alex when you think about what you loved what you truly loved in this journey of building morning Brew what comes to mind

1:06:35

and basically everything that came to mind were the first four years of the business it was the ideation of the company it was the the invention of the product it was me storytelling and selling investors employees and Brands um it was the the feeling of like being in in battle with four or five people as The Underdogs against the 900 pound gorillas of media like those were the

1:06:59

things that felt great to me and so I basically said to myself well if I have the incredible privilege of deciding what I do in my time now why don't I just do those that exact things over and over and over and so you know my my desire moving forward has been build infrastructure that allows me to do basically three or four things ideate businesses talk to exceptional founders

1:07:24

to help go through the idea maze for those ideas or find as potential CEOs for my new businesses create content that that gives me distribution to drive opportunities for my businesses and to focus on helping increase the probability of my new businesses going from zero to one everything else I will give to someone else by having a CEO running the day-to-day of all these

1:07:46

businesses and that's kind of how I got to that point that's a fascinating story and I guess two immediate questions um the first is uh can can can somebody who doesn't have those first two things right like your goal was to make a lot of money uh so that you could take care of things and your family um and but you got that right so that led to the very thoughtful way that you exit it is there

1:08:17

a way somebody without that certainty right uh they don't know they're going to make a lot of money or they you know not sure can can they approach it the same way or you got to go through the other one first it yeah I think part of the question you're asking is like can people in the beginning of their career uh or in kind of their first step before they've realize the extrinsics like

1:08:41

gotten the extrinsics can they just be driven by intrinsics and I think the answer is yes I think I think there are people who are wired intrinsically to do things for their desire to be creative curious and grow uh build connection Etc and by the way I actually think the inic are the best long-term motivator right because everything I just describe the extrinsic I I almost think about it as

1:09:08

like um as uh like a Sprint versus a marathon it's like uh the extrinsics are great at high horsepower for a short period of time the E the intrinsics are the Slow Burn forever um so I do think it's possible and I actually think a lot of I don't know in some ways I feel like the extrinsics often are are driven by these stories we've had for a long time in our lives based on experiences we've

1:09:35

had in our lives for uh in our childhood or early adulthood right it's like these stories I have are because things I experienced as a kid or a college student or a high schooler it's interesting to think about what would be my drive if I didn't experience all of those things so yes I think it's possible I think it's rare um but part of me is uh honestly I'm partly on a on

1:09:58

a a journey to figure out how do you bring that out in people their their intrinsic drive to build because to me it is the healthiest long lasting version and it's funny because for the longest time I always said I loved hiring people who have a chip on their shoulder like uh you know there's always this saying like chips chips on shoulders put chips in pockets and I

1:10:20

think it's true but I think the ISS issue is is when you hire someone who has a chip on their shoulder they are deriving their happiness from someone else's reaction and as soon as that person say gives them the reaction they want then where's the chip on your shoulder goes away and so I actually think chips on shoulders can be helpful for employees who are at your business for a period of

1:10:48

time and maybe the chip never goes away but I think for if you want if you're saying to yourself like you want to invest in an Entre entrepreneur for every business they'll ever run I think at some point that driver runs out it runs out of steam so I wish I had the answer to how do you Channel intrinsic motivation how do you allow people to basically conjure it from day one but I

1:11:10

think if I had that answer I also would have done it and so I'm still on the hunt for for how do you do it yeah and I I think that the uh differential between intrinsic and extrinsic is a really good one to look at because like for most of my adult life even since starting as a teenager I I love the Dow Jing uh by lau and and one of the things I also wrote letters to my kids when uh starting when

1:11:39

my son who's the oldest in the family was like six days old and what was interesting was the the quote that I used was from lau and that was the quote basically was looking at intrinsic value versus extr inic value and and lau is saying yeah if you have power over other people yeah you're powerful but are you master of yourself uh you know if you're if you're looking for happiness outside

1:12:05

of yourself guess what you're never GNA find it you're gonna find it within yourself and and so that has always been kind of something that when I was uh looking for teammates it's really hard to sus out though right yeah I yeah I have a few thoughts on this I think so by the way what one one thought that came to mind is while I don't have the answer for how do you drive

1:12:33

intrinsic motivation I think one of the best resources that I continue to read and like go deeper in because I think it allows you to kind of locate where you're coming from like because I think a lot of times people don't even have awareness of what is the thing that's driving them and I think be able to locate it is the first step is there's this book called 15 commitments of

1:12:55

conscious leadership I don't know if you've ever read it but it's the best book on leadership I've ever read I just continue to read I'm always reading it I'm always just referencing it um it's by this organization that's called the conscious leadership group my executive coach is trained in conscious leadership and it basically talks about all of us are always existing either above the

1:13:16

line or below the line above the line is operating from a place of Love curiosity growth and abundance below the line is from a place of uh fear um uh scarcity defensiveness um Etc and basically goes through how to both um identify whether at any given time you're above the line or below the line but also ways in which you can shift from below the line to above the line as in extrinsic to

1:13:43

Intrinsic or fear-based to growth based and I'm just going to give you an example because I was literally talking about this with my executive coach yesterday and I I think it it was really powerful for me because I don't think people realize actually the the downside of being in uh extrinsically driven or fear driven um like I think people rationally understand that okay maybe

1:14:09

this motivation will only last for a period of time but I don't think people actually realize the cost that it has on their life and so I'll explain what I mean um something that I brought up with my executive coach is that I feel a great deal of anxiety every single day I think about it of how much I have to pay him I I shared this with him um it's the most I've ever spent on like personal

1:14:33

growth it's $6,000 a month and it's like uh 2015 Alex would have literally thrown up when he heard that number but I basically said to myself like this is a really important exercise because if I can't invest in myself when um rationally I shouldn't be worried about paying for this service then what is the point of making money if I'm not going to invest in myself and my family and so

1:15:00

I brought this up with him and you know he asked me this question of like do you do you actually worry finan like I want to he was like I want to get this out um on the table first are you do you worry financially about paying for this service like do you think actually it's going to make you go broke like lead to other really painful trade-offs in life and I said no I do not and he said okay

1:15:23

first thing I'm going to say to you is I'm not going to ever sell you and continue to work with me but what I will say is even if you decide to leave me so you cannot pay the $6,000 anymore I want you to actually understand where it is coming from because otherwise you're going to find the next opportunity next time where you have to pay $6,000 or something and you're just G to have the

1:15:42

same pattern or behavior and so we went through it and he basically asked me like why do you think it is what do you think it is driving this anxiety around not be being um about about paying me this amount each month and I said I think it is because I started by talking L I was like I think it's because of this feeling that I don't have I don't believe in my abilities to build

1:16:06

businesses and I believe that the way that when I stepped out of morning Brew like I shared before that I have this amount that I made from the sale of our business that is going to be the amount that I only ever make and so I have to do everything possible to hoard it protect it at all cost because that's all there will ever be and he asked me to sh like what why do you believe you

1:16:28

can't um build a good business and I tell this story of I had this story that my co-founder did not find me valuable that he felt like I was dead weight I literally visualized like I was weaken at bur I was Bernie from weaken at Bernie and he was just like holding me up while building the company and because I have that story I don't believe I have actually any of the tools

1:16:48

to build a great business so one thing I'll share is when I told him that story he said well do you know that's your co-founder story like have you ever asked him I was and I said no and he said well I'm going to ask you to ask him and and he was like when are you going to ask him by I was like by next session so I had a two and a half hour conversation asking my co-founder what

1:17:05

his story was of me from the business what I will say is any co-founder any person who has someone close in their life who has existing stories of what the other person thinks it is one of the most powerful exercises to call out the story and to see how close or not close you are um but then basically my coach was like okay one I want you to realize that everything you've just shared is a belief and it's

1:17:30

a belief you believe to be true but it's not true it's a story you've had for your entire life and you believe so deeply in it that you just treat it as truth but the second thing I want you to think about is what is the cost of having this belief what is the cost of you not believing in yourself of you not um believing you have the tools to create any outcome you want to create

1:17:49

what's the cost on your marriage what is the cost on your future kids and I said well the cost on my marriage is that I'm going to continue to uh say to myself that I have to work hard not smart because I'm not effective in my work so I have to spend more hours doing it which is going to cause me to be less present to my marriage because because even when I'm at the dinner table with

1:18:08

my wife I'm going to be working because I feel like that is a justification for overcoming my inabilities or lack of intelligence so it'll put um a distance between my presence and my marriage and for my kid my you know when I have kids me not having self-belief in my abilities will turn into me um into me modeling lack of self-belief and lack of self-confidence which which he's like

1:18:35

and what will that do to your kids the odds are that'll give them them also lack of self-belief and lack of self-confidence and so I thought it was just such a powerful exercise because I don't think people appreciate that when they do things even that they acknowledge are extrinsically driven or fear driven I don't think think they actually appreciate all of the non business or professional related impacts

1:18:57

that it has on their life by having these stories and so I think actually uncovering these stories and understanding the true cost of them the non-financial cost is actually the most powerful exercise people can do I love that example and it fits really neatly with the whole idea of premeditation that's essentially you've just described one of the most powerful parts of

1:19:20

premeditation is exactly that I love the adding in well go ask your co-founder what his story or her story is about you and you're G to find that many many times it is not even close to the story that you're telling yourself I had as a guest will uh store who I discovered through a book our family has a a comingled uh Kindle and somebody else had uh bought this book uh scientific

1:19:48

storytelling by Will store I'm like oh this looks like a good book and so I read read it and like this guy's a genius because essentially what he does is exactly what you just went through right because we tell a story like propaganda really easy repetition repetition repetition that's all you got to do and people will believe the craziest [ __ ] right just keep repeating

1:20:15

it and and what store unlocks in his book is guess what you're the author here you get to write a whole different story if you want to and and and that is a really insightful thing and amazes me that more people why do you why do you think like I'm sure you've shared this story with other people do you find when people are reticent to to embrace that what is that just another story they're

1:20:44

telling themselves yeah yeah I think it's um one I think our our reptilian brains love comfortability like I think uh you know if we if we play the put put the Hat on on me as The Reptilian Brain Hat it says you know I've done a pretty damn good job of the last 30 years Alex has stayed alive and uh you know how how I've done however I've done it he stayed alive so I'm G just do the same exact

1:21:13

thing for the next 30 years because that's my goal I want to just keep him alive so I just think that there's like this deep discomfort with uncomfortable things because it poses a risk to stasis and stasis has been proven to work for us in the past um I also think people feel like it's you know this idea of like manifestation or changing your stories like I think um it's really

1:21:38

unfortunate I think it just like suffers from like a a branding problem because people think it's like feels like spiritual or woo woo but like it it really is like at the end of the day it's like if you believe that that if you believe in propaganda if you believe that you can create a story and repeat it over and over in society and people will believe it what changes about that mental model

1:22:03

to say the same thing for yourself that if you have this story you've repeated over and over why wouldn't you believe it and I I don't think people just appreciate that and I I do think there's actually like opportunity to Rebrand the changing of beliefs and stories in ourselves um and you know one other thing I just want to share that relates to kind of to to bookend like my

1:22:30

journey of kind of refining identity and motivation and self-confidence post Brew acquisition is there's um there's another exercise that I did uh that's Again part of conscious leadership group and it's the exercise is focused on finding your zone of Genius uh and zone of Genius actually in some ways is it's kind of similar to like you know eeky guy um where zone of Genius is basically two things

1:22:59

it's the skills or activities that you spend time on that you are exceptional at and time melts away people understand that but then the next question is like how do I okay how do I know what that is how do I find that and I find that there are two great ways to find that and it's how I've done it the first is this thing called The Best Stuff exercise by conscious leadership group and a PDF

1:23:23

that um people can fill out and by the way I'm no affiliation with the group I just I found it very helpful basically this exercise the best stuff exercise it's a few steps all it says is first list out eight experiences in your life whether it's work whether it's relationships whether it was when you're kid when you were a kid or as an adult where you felt like you were crushing

1:23:47

what you were doing and you were loving the thing that you were crushing and I so you go through the exercise I wrote down eight things I'll share a few examples one was me moderating a panel with Andy Dunn the former CEO of bonobos when he had his book launch event for his book Burn rate the second one was me pitching uh the CMO of JP Morgan on working with morning Brew back in 2016

1:24:13

when I was by far the most Junior most unknown person in the room the third is me building the tajma hall behind my right shoulder out of Legos and that that's like one not at all tied to work and one more would be me talking to the founder of a business that I Angel invested in him talking me through a really difficult Personnel Challenge and us spending 45 minutes on the phone just

1:24:39

like workshopping how to think about this problem and so you write down these eight things and then you write summaries for each each of the things where you write what what was your involvement in the activity what do you believe you excelling at and why did you love what you were doing and so you write those all down then the third step is you find themes what are themes you

1:25:02

can draw out of these eight or nine experiences that are completely disperate in the context of your life and for me I wrote down like six or seven themes it's uh invention it is um storytelling it is coaching uh and there are a few others and then the final step is you take these themes and you basically synthesize a uh a the a hypothesis a hypothesis of what is your

1:25:26

zone of Genius what is kind of like your calling based on the things where you've felt most alive and you've excelled most and the way the sentence I wrote was um mastering coaching creativity and storytelling through the vehicle of business and so I I did that exercise and then basically my way of testing against that exercise is I went to three or four people who know me really well

1:25:55

in my life and I asked them a set of questions one of them was my co-founder Austin and in that discussion I had with him I asked him these questions I said what are my one or two superpowers what are my one or two Achilles heels while running the business with you when did I look most alive in the business when did I look least alive when was I most helpful over the Journey of our company

1:26:17

when was I least helpful and basically I got answers to all those questions and I compared them against my hypothesis and things were pretty spot-on and so I just found that to be a highly valuable exercise that because something I often do is I ruminate on this question of how much am I extrinsically driven by things how much is it truly intrinsic versus extrinsic I think one of the best ways

1:26:37

to get out of that kind of circular reference because you don't actually ever know the answer of how much is it driven by money how much is actually driven by growth is by doing this exercise of like when did people see you at your most energetic where you're not the judge of it and then you compare it to this uh kind of of self assessment you did on your own brilliant and and uh you know I I

1:27:00

one of the reasons I was so looking forward to this conversation is we are so sympatico on so many uh ideas uh another one that I found helpful that I managed to like learn early on was I I learn the ability to treat myself as another person and and I would say okay if I was looking at Tom over there what would what advice would I give Tom and it's really interesting because the first

1:27:30

couple of times you do it feel just like an idiot right Jim you know you're actually talking about yourself you dumb [ __ ] but the more you do it the more the that that illusion takes hold and that person you can name I find naming them something other than yourself is very helpful uh sometimes many them with different sex is also helpful uh but making them so other from you yeah that

1:27:57

it that it really kind of takes I love that yeah and and some of the stuff that comes out is like holy [ __ ] right because we are so much better at seeing the flaws and our strengths in other people and and for some reason we have this blindness to our own skills or and deficiencies much more often our deficiencies is what we're absolutely blind to and because you know like the

1:28:28

lake won effect gison keer is mythical place where all the women are good-looking all the men are handsome and all the children are above average right uh and and like when you look at all the surveys men are particularly guilty of this like uh you know please rate your athletic ability everyone's in the top 10 or 20% absolutely whereas I know I'm in I'm in

1:28:55

Barrel number 10 yeah so it's so it's so funny I yeah it's I feel like I suffer from the opposite side of the spectrum where um and I don't know if this is kind of like falling within the vein of like you know comparison is the enemy of contentment and I'm always kind of uh using people who are exceptional as a reference point in a thing where I feel less exceptional but actually like I

1:29:18

think this was one of the things I realized even in my discussion with my co-founder is I had this story of myself that was you know Alex was you know started this thing and for the first few months he got it off the ground but then he brought co-founder on and he wasn't helpful basically ever after that and I think what happens what I actually find that stories often times can have truth

1:29:41

to them but they are caricatures of what the real truth is and so like the real truth of the story as it was told to me is Alex was at his best and His Highest leverage in the first four or five years of the business where what was required to build a company was willing the thing into existence to having uncanny belief for a thing that didn't really exist yet for um you know for having a product

1:30:10

Obsession to create this kind of new category of product that didn't exist when things shifted to it's more about process it's more about scaling it's more about uh building out a leadership team it's more about having the operating system that's where Alex lost leverage because he wasn't doing the things that came most naturally or excitingly to him and I think what's

1:30:31

interesting is right that second story is the story that I latched on to where I just lost leverage as a co-founder or CEO because I had this story that you look at Bill Gates you look at Elon you look at any of these Founders that basically went from you know garage to ringing the opening bell and you're like well they scaled as a CEO like clearly that is what you have to do and I took

1:30:55

all emphasis away from the first four or five years where which is actually where I was kind of living in my Brilliance and living in my zone like I completely just discounted it to zero and I think part of the reason also is because it's a distant memory from now it was you know five or six years ago now but also to that point of it's so there's a certain brain which my brain actually

1:31:15

does it's so much easier to focus on the the places where I felt inadequate yeah and the other interesting thing about that is we often naturally discount within ourselves talents that we because we possess them we think oh well everyone everyone must be good at this right and and you know it's that whole you mentioned earlier work hard versus work smart like I was always a work smart person I and and I

1:31:45

kind of thought well everyone works no not at all abely you are in The Amazing minority uh because yeah I uh I always was like the the person who had the cliche of like you know I'm kind of I I I would always tell the story I'm average intelligence and so I need to compensate with uh above average work ethic and so I think to be in the camp that's working smart I think it's it's

1:32:10

uh an amazingly aspirational thing for most people um and yeah you know I think uh the the other thing the other thing about kind of all of this is um like like we said we we discount ourselves on the things that we're actually good at and I you know something that my co-founder said to me was you know when we were first starting morning Brew I never met someone in my life who is so persistent in making

1:32:44

things happen for themselves like in getting things to happen and I never met someone who was so Unapologetic about what we were building even though uh maybe there wasn't reason to be so confident in it and to your point it's like I would have never necessarily described myself as incredibly resourceful and Scrappy or uh you know uh someone who didn't give a [ __ ] what

1:33:10

other people thought but obviously that is something that is just like that is my way of being and um I think it takes talking to other people to realize your way of being may not be the common way of being totally totally um well uh uh I could talk to you forever matth and I'm already looking at an hour and a half but I do want to ask specifically about

1:33:36

story art because it is it is really close to something we're we're spinning up over at oasi Adventures so I want to compare notes what what what gave you the idea um and and how are you thinking about executing against it yeah so um like I said th this all plays within my desire any companies that uh at least in the beginning I don't have to raise Venture funding for I can cash flow them

1:34:03

pretty quickly um and then if but that doesn't necessarily change the ambition of the business it maybe just change the changes what is the uh at least starting point or the starting business model so the idea for sto story ARB came about because one day I was just sitting and I I was on Twitter Doom scrolling like do and I saw someone talking about their nor their new short form video agency

1:34:26

and I just had this thought and and by the way I talked to someone who had a short form video agency a week prior and he had shared with me how churn was like the hardest part of his business how like they would churn through 40% of their clients every two months I was like that sounds [ __ ] miserable um and I thought about it and basically the thought I had is like I feel like short

1:34:46

form video agencies are in Vogue right now because a lot of people want to be creating short form content they don't actually have the editing chops to do it there's this huge offshore Arbitrage that's happening of using talad in the Philippines orri Sri Lanka to create your content but it feels like a race to the bottom because it feels like the service will be commoditized and you

1:35:06

can't actually track Roi for a client how is a client going to actually think to themselves I can justify this $33,000 every month if it's just based on Impressions versus driving actual relationships or business and so then I had this thought of like Twitter and Linkedin are pretty awesome for driving opportunities like all my opportunities have come through my Twitter and my

1:35:27

LinkedIn but I don't really know of agencies that have used that as the starting point and I actually think it can be uh easier to actually drive our like truly attach leads and revenue to content you are putting out on these text based platforms and so the idea the idea came to me and like my way of building businesses is to do it out in the open and just continue to kind of like scale up risk as I get

1:35:58

validation so the first thing I did I literally posted on Twitter about story AR but didn't even have a name yet there was no business I just said I I I think I said if you're interested in taking your knowledge and and um turning that into content on Twitter or LinkedIn um to build your personal brand you're willing to spend five to $10,000 per month and I think they're your CEO or an

1:36:22

exec and there was like one other filter DM me I got like 15 DMS so I was like okay there's demand now I'm going to go look for Supply I did a tweet the next day and I said if you are a writer who wants to write for executives who are looking to build their audience on social DM me I got a bunch of DMS and then I for the first few months all I did is I made it a matchmaking process

1:36:43

where I basically paired writer who I had qualified with executive and I said to the writer I said tell me what you charge for client I'm going to just pass through the entire cost to you I just want to sit in a slack Channel and watch everything you do for a month or two months so that's what I did they the initial clients paid $3,000 a month they passed it to our ghost riter like I

1:37:04

didn't even have them wired to my bank account I just gave my ghost riters bank account to them and I just observed and then I said to myself okay what is everything I can take off of the writer's plate so they are just focusing on the creative aspect of the job everything administrative or content strategy or reporting on analytics related I will handle as basically the

1:37:24

account manager so there were a few months where basically that Arrangement existed where I got to four or five clients I was conducting content interviews with these Executives I was sharing that with the ghost writer I was handling payments uh setting content strategy checking uh how many leads I was driving for clients Etc and then we got to a point where basically I was

1:37:43

like a full-time content strategist I was like okay now's probably the time to hire CEO and I had I had a traction where I my thought was there's enough legitimacy here where I could hire a very good operator of the business so then I tweeted out and Linkedin posted out I'm looking for a CEO for this business uh for story ARB Meanwhile by the way there is not a website at all

1:38:04

there still is not a website for the company it still does not there's no website for the company today and I got 70 candidates I narrowed it down to um seven people who I took through an interview process one person I thought was the person I put them through a contract to full-time process for a month they were the operating CEO of the business and basically that was the

1:38:26

starting point now what is the thesis for story ARB very simply I want to build what I describe as the media company for the personal Media company for the modern executive so for the professional who has deep industry Insight specifically a B2B executive uh Venture investor private Equity investor real estate investor my whole view is what we were talking about which is actually the best

1:38:53

industry professionals have not built any brand on social because they're too busy building great companies I actually think like the mediocre people like me are the ones building brands on social and so my view is is if I can actually help exceptional professionals become creators but being a Creator is not a full-time job for them we can start with LinkedIn and Twitter then we can grow

1:39:14

into other rented audiences whether that's short form video sure we'll throw that into the mix then we move down to owned audience like um email podcast or communities for the niche that they're in and then what I get really excited about is actual like businesses monetized audience and so I'll use an example for you for you one of our first clients is uh I'll call him like the the

1:39:38

next Nick Huber he's a self storage um developer and investor amazing guy and we've been working with him f for five or six months and we've doubled his audience which is great but actually what matters more is what's who that audience is and what's been driven from it so he 10 thou let's say he has uh 12,000 followers of that 10,000 of them are Real Estate Investors or developers

1:40:04

super high value audience right like I think it's in a lot of ways how uh you know how Patrick thinks about the quality of audience across the podcast Network right for Colossus and so basically with him we built up this great social audience we're also driving leads so we've got a ton of inbound investor interest for his funds so like he can attribute Roi to it to story ARB but now what I'm thinking about is how

1:40:30

do we take over his newsletter so now how do we funnel these people into email build an ongoing relationship for people who want to go deeper in Self Storage but what I get really excited about is what's a business I can launch with him how do I go to him and say hey we've built an owned audience for you let's actually treat you like we treated me for story ARB where I give you half of

1:40:48

this business you give me half I go find a person to run this business we figure out the idea for the business by testing your audience putting ideas out into the world just like I did with story AR and we built for you you look at at it as effectively passive income maybe there's a few hours each month where you have to dedicate to the business but that's it

1:41:08

and it potentially helps reinforce like the the fund or the investment business you're building so an example for him would be like what does it look like to launch a YPO or a Hampton for Self Storage investor what does it look like to launch the first trade show for Self Storage investors and all of a sudden if you're known as the guy who not only has these new lines of business you're also

1:41:28

seeing more deal flow you're seeing more properties Etc and now I've built up distribution for every new business I'm launching brilliant absolutely brilliant uh well we'll be stealing all of that from from you for please do well listen Alex this has been actually surpassed my expect ation this has been so much fun um and if you have listened to our podcast in the past you know that at the end what we do is

1:42:01

we wave a magic magic wand and we make you emperor of the world only a couple rules around that you can't kill anybody and you can't put anyone in a re-education camp but what you can do is we're going to hand you a magical microphone and you can speak two things into that microphone phone and the two things that you speak will incept the entire population of the world 8 billion

1:42:28

people whenever their tomorrow is they're going to wake up and say to themselves or their spouse or their significant other I've just had two of the greatest ideas in the world and I'm gonna act on each one of them not just think about them what two things are you going to incept in the world's population this is going to probably I'm going to get called out from the woo woo crowd but I think if if uh if I

1:42:56

actually thought to myself I have the power for every person in the world to have two thoughts to to live life in a certain way I it like it feels cringey to say but I think it it it is what's true to me which is like if every person could wake up tomorrow and believe and and it's the reality that they love themselves and then the second is that they choose to love others I think

1:43:21

everything would be way better I think um you know the the way that I think about it is like we're building so many incredible things in the world but if we do not have people who have self-belief and um what's going on up here being in a good place for themsel and also if they do not have empathy and love for others what's the point of all of it and so yeah I love myself and I love others

1:43:43

is how I would choose for everyone on this planet to operate through life I love it and there you go you so you already incept me man I love you I love you too thank you so much for having me all right Alex you will definitely be on our return guest roster because this was so much fun love it I'm I'm excited for the return Tour all right Alex thanks so much thank you