The Myth Of Online Entrepreneurship | Jack Raines

That's what gets missed on this. People are saying go all in on entrepreneurship or you have to do the job. Nobody should ever just quit without being in a spot where they could go a year without working. If you're going to quit, you either need to have a lot of money saved up so you can go in on it, or you need to keep like a revenue stream or an income stream coming so you can experiment with other things. If you need money too soon, you'll make decisions that might be bad in the long term for your side thing, trying to monetize too soon.

Welcome to the Callum Johnson Show. I'm Callum. And today we got my man Jack Raines. How you doing, man?

Good, man. I'm very happy to be here. Appreciate you having me.

I'm happy that we have you. And you know what, um, I'm gonna give you a little intro. So, um, obviously you have the Young Money newsletter, over 43,000 readers. Um, kind of how I know you and like what, what the title is for you in my mind is like the ultimate shitposter. I saw, um, I saw a post that you did in the last few days around paying the Starbucks barista.

Yeah, I was, I was pulling up right now to see how it was doing. Yeah.

And I'm just seeing you in these exchanges with people on Twitter about like, is it real? Did he really do this? You're like, nah, it's real, it's real.

Oh, it's hysterical. It's the most entertaining thing on the internet right now.

Yeah, yeah. No one actually does that better than you. Um, and then obviously like you've also run courses and, and been teaching people about like building and monetizing newsletters. Um, I think to be honest, like when it came to I, I had been aware of you for like a little while. Yeah. When it came to getting you on the podcast, I think really what stimulated it was I saw the article that you posted, um, 5 Career-Related Things I've Changed My Mind On. And first of all, it was just really well done and like very authentic, uh, and just helpful to read and valuable. Um, but I think it's such an interesting article in this moment And the reason that I say that is I think if you spend time on Twitter, on social media, um, you hear these stories, right, of these people in their like early 20s, maybe like mid-20s, racking off 10K a month, 20K a month, 30K a month, um, and this lifestyle of being like an entrepreneur, of doing your own thing and being able to do it at like a really young age. And have it just be super successful, I feel like the way it's portrayed is like it's easy. And when I read your article, I felt like I was actually getting the real perspective. Yeah. And the balanced perspective, not just of like someone that's made it, but someone that's doing it and can kind of report back on like, this was my real experience. Um, so to be honest, that was one of— that was where I wanted to start. And I'm actually gonna, I'm gonna read out like a section from that article and then we can, we can kind of talk through it. Um, so point 1 is work and traditional jobs aren't prisons you should seek to escape. From 20, from 2020 to 2022, I had a jaded view of traditional employment. After 18 months of responding to emails in my PJs while eating Cinnamon Toast Crunch, feigning interest during Zoom meetings and rearranging spreadsheets, I came to believe that employed folk such as me only had two options. The first one was work for yourself. The second one was escape the labor force entirely. However, over the last year, I've had a change of heart. So here's where I want to begin. Um, explain to us what is the change of heart? This episode is brought to you by Free Agency. If you want to take your career to the next level, Free Agency is a company that you should check out. They manage and represent talent in the tech industry, and they provide you with a dedicated talent agent to help you find, engage, and win top-of-market roles that will maximize your earning potential. No more leaving money on the table. Stop job searching alone and start building your dream career today with Free Agency. Anyway, back to the show.

Yeah, I, I think it's— I went from one extreme to the other, where like coming out of undergrad, um, we can get a little more into all of this later, but I knew that I was going to business at Columbia University, but I had to work 2 or 3 years before I started. So at that point I was very much on this traditional path of I went to an okay undergrad school, I got into a very good MBA program, and I need to just do a job for a few years. And then after business school, like consulting, investment banking, kind of like what we talked about before the show started, like what you were thinking when you moved to New York. Like I had a very, I'm going to win this traditional employment game. And then when COVID hits, um, like I'm starting my career in February 2020 when I finished school the December before that, and I'm working a typical, um, like financial analyst job, pretty normal, like first finance job out of college. But after one week in the office, COVID hits and we're going remote. So then I'm stuck there doing what like a lot of other people my age were doing in their first job, and they're sitting in their apartment on a computer updating spreadsheets. And looking back now, I think a big part of the reason I hated the experience was no companies were actually ready for that change and didn't really know how to like do remote employment, especially with new employees. Like I never really got onboarded, hadn't developed that chemistry. If I'd been working there for 6 months, I would have my work friends and my group and would be in my rhythm, but I never got to establish that. So between that, I made some money trading stocks during COVID I was sitting there a year and a half later. Where I had enough money where I just really didn't need to work for a year. Like I could cover my expenses. And the last 18 months had just been such a, like a monotonous Groundhog Day of same thing over and over again. And I really think it was just, I was going stir crazy from being in my apartment too long, just feeling like locked on a screen, moving my mouse to appear like I was working. Like it was ridiculous. So at that point I went from thinking, oh, I want to do this, like get really good at this business school promotion, next job to thinking, This is a ridiculous way to spend 40 years just doing tedious tasks for some company and then retiring and dying. So I went from being like a very Type A, I want to win that traditional employment game, to screw all that. I am just going to go travel, figure something else out after business school. Like jobs are like, jobs are a trap basically. Um, since then I haven't come all the way back to thinking, okay, I'm going to go like get an investment banking job afterwards. Frankly, for my LinkedIn content, it would cause some red flags and any kind of like onboarding meeting anyway. Um, but, uh, there's, there's definitely like, there is a lot of value and like appeal to regular jobs. There's nothing wrong with stability and getting paid, like getting paid a good wage to work 50 hours a week or whatever, and then that leaves you free time to do whatever you want. And most people should do traditional jobs. Like, not everybody can just be a freelancer, do this or do that. Like, we, like, we need people doing stuff, and not everybody has to make their job a passion project. Like, I think you should look at your life holistically, and if your job is something that you like maybe a 6 out of 10, but it gives you the money and the freedom to pursue the things that you really love without being forced to make a living from those things. Like, that's a good balance too. Um, so I mean, I'm, I've pretty much established, I've hit a point now where I've like basically figured out how to make a living from doing my own thing. But I also think there's a ton of value in people doing like regular jobs, like, like jobs shouldn't be vilified. It was just my experience with my job happening at the beginning of COVID It just wasn't a great experience. So that gave me a pretty jaded view. Yeah, but I'm a lot more— there's nuance. Like, it's not black and white. Like, there's a lot of gray area in careers and employment. There's a lot of different paths people can take that work. Just depends on the person.

Yeah, no, see, and that's what I like. I like that you add the nuance because I think so many conversations, especially online, are very like black and white. Um, you know, I want to key in on one thing. I want to key in on something that you said, and it's a phrase that you used, and and I actually think it's really apt, which is the traditional employment game. And I remember coming into, um, I remember coming into the workforce and like starting to work out of college. I had this very like idealistic view, I guess, of working. I did not see this as a game at all. For me, it was like you come in, you work hard, the people that work hard and like perform the best get promoted and get the jobs and whatever, um, get the best roles. And I remember having a conversation with someone who was 20 to 30 years more experienced with me than I was, uh, because I was just frustrated at the time, like, seeing other people just get better opportunities, right? Um, and I remember she said to me, she was like, Callum, you need to start looking at this as a game. And when she said it, I didn't even really get what it meant. I was like, this isn't a game to me. Like, I'm trying to like win. Like, I'm trying to really produce something here, um, like build the life that I want. Like, it was— it meant something to me. Um, but really what she said was so true because when you think about what a game is, any game, you take basketball, you take football, uh, the NFL, whatever you want to take, there's certain rules. And the people that play to the rules and are the best within those confines they win.

Yeah.

Um, and so you might be doing a bunch of things in your job or in your work that has no impact on the actual final result or the rules that matter for that game. And so once you start seeing it as a game, I think things change. Um, and it almost starts to raise questions of like, what game am I playing? What are the rules? The people that are like successful in this domain, what is it that they're doing to a higher degree than everyone else? Um, and it really brings me to the fact of like just knowing the game that you're playing. And I think you actually make a point of it in point 2 of the article. Uh, and point 2, I'll just read it out, is what you want to do is so much more important than what you want to tell people you do. And I almost see that as like, what game are you playing? Like, a lot of people are playing a game that it doesn't— what that game maps to, it doesn't hit any of their goals, it doesn't build them the lifestyle they want, it doesn't— it's like, um, a lot of times it can be like an ego thing, or you're just looking around at your peers and it's what they're doing, or it's like cool to say that you're like, I have this job, or I work for this company, I went to this university. Um, and one of the things you said, you said you shouldn't do the job you want to tell other people you do, you should do the job you want to do. I'm kind of curious from your perspective, like, how did you come to that realization? Like, what's the story behind that line?

Um, the whole thing started when last September Derek Thompson, who writes for The Atlantic, has a couple of podcasts. Um, he's one of my favorite as far as like people who has a newsletter or blog. Derek Thompson is phenomenal. But he wrote a career piece called Your Career Is Just 1/8 of Your Life, and it was like 5 pieces of like career advice from his life. And that was the point that stood out to me was like, that was the first time I heard that. Don't do the job you want to tell other people you do. Do the job you want to do. And he got that from— he got— he had a job offer to— I can't remember what it was. I'm pulling it up now. It was, uh, he didn't go to details on it, but it was a very fancy, like high-up job offer that would pay well. And he was telling one of his coworkers, a guy named James Fallows, about this job offer he had.. And James literally told him that, like, do the job you want to do, not the one you want to tell people. And it hit Derek like a brick. And he declined the job offer that day because he's a writer. He likes writing. He'd been writing for a decade. Like, that was his thing. And it was at a time where I had— like, I knew in the back of my head I like the writing thing. I like what I was doing online. But I was also in my first semester of business school, and there's all these banks and consulting firms and venture capital firms and PE firms, and everybody's talking about recruiting. And you still feel that almost like almost compelled to like, go look at one of these other things because it's like a shiny object. Um, but that article really stood out to me. It was like, I, I know what I like doing and I've found I have enough momentum with it now that I know that it's by the time I graduate from school, I'll realistically hit my escape velocity on being like self-sustaining in the content game. So anything else would be a distraction, even if the short-term, like say the short-term salary coming out of business school is like $300,000 and maybe I'm making $150,000 doing my own thing, but the exponential growth on doing my own thing at this point is just so much higher that anything else would be a distraction that would take away from that. Um, you see it on Twitter too. Like, that's a real-life example. But there's this, like, I think part of it was there was a lot of money getting thrown around the last few years, but everybody wanted to get into venture capital. Everybody wanted to be an angel investor or scout or an advisor for a VC firm. Um, but Tim Ferriss wrote a piece like several years ago about how he stopped actively investing because after his first book, The 4-Hour Workweek, was a hit, he just got very plugged in with a network of people with a lot of access to a lot of deals. And he got in as like an advisor. He got some shares of Uber, Twitter, and some other startups. I think Shopify back when they were small. Um, but one of his friends had told him that like the investing stuff was great. Whatever you do, don't stop writing because you can like change people's lives with what you're writing. And it hit him that he didn't have necessarily an edge as an investor to the point, like he couldn't make the same impact investing. Other people could do the investing that he could do, but as a writer and a podcaster and an interviewer, that was where he could really stand out and make a difference. So between Derek's piece and Tim's piece, Tim's piece, and then just kind of like realizing how I felt about stuff, it just clicked with me that you just see people, once they hit a certain level of success or recognition, they start getting a lot of opportunities to do a lot of stuff. I think that's what screws people over is they get really good at one thing and then they have access to a lot of other stuff and they just try to do it all. Um, and it's— I think it's more impressive when people really lock in on that one thing that's theirs and just own it.

Mm, you know what, that is so, that is so true. And it's interesting, um, even when we spoke yesterday. Yeah. Um, and we spoke about your article about the category of one. Um, And I was saying to you that like even in the podcast game, I look at the, the biggest podcast, I look at like Diary of a CEO or Rogan's Pod, um, even like Call Her Daddy, like all of the, like the ones that get the most listens. I feel like the host has a very detailed, specific understanding of exactly what their edge is. They know exactly why people are tuning in. And they play to that. And I think one of the things I saw, uh, working— and to be honest, I just see it a lot in general— is most people are completely unaware of what their edge is. And I think one of the re— one of the reasons why your content resonates is because it's authentic. And when you're doing something with authenticity, it almost implies that you have an understanding of your edge. Yeah, because you kind of know who you are and you live in that. And so I'm curious, and I think it can be a lesson to the audience, like, what was that journey of you discovering what your edge is?

I think for me, um, like, I started writing Young Money, my finance blog, about 2 years ago to the date, and I didn't really know where I was going with it at that time. Like, I had— at this point, I just quit my job. I was planning on traveling for a good bit. And I was literally trying to get a staff writing job with Morning Brew or another, like, more established publication. And other than a few freelance finance articles here and there online, I just didn't have a big portfolio of work. So I apply, don't get hired. Like, they shouldn't have hired me. That would've been like, I was not a hireable person as a full-time staff writer at that point. But I said I would, like, I told myself I would launch this finance blog and just start writing a couple pieces a week just to prove that I could put out consistent content at like like a, like a high click and what I thought was high quality. And then I would reapply in 4 months and I literally just wanted to do that for maybe 9 months before school started. Um, but I didn't know what I was going to write about other than finance at that point. I thought it would be right about like initially I was still trading stocks a lot. I thought maybe I would write like write-ups on different stocks. And then I realized that would get commoditized. And I also can't actually give a detailed like analysis of a different stock every week like that. One, that would get boring. And two, it just wouldn't be authentic. Um, so then it turned into maybe I'll do like one, like personal finance tip, like Roth IRA versus regular IRA, or should you rent or buy a home? And if you go back to my really early stuff, some of it was more along those lines. Do one of those and then a more just general, almost philosophical but money-related piece where it was kind of like talking about life, but through the lens of finance, like why people should worry, like why people should spend more money when they're younger to maximize life experiences. Stuff like that. But it took probably 3 or 4 months of just writing a lot of stuff to figure out what I actually liked and what people were responding to. And you have to put a lot of stuff out there early to, like, basically to get a big enough sample size. It's like the scientific method. If you're experimenting anything, the bigger your sample size is, the more observations you have, the more accurate your takeaways are. Um, and you also kind of hone your voice. And it hit me that like two people that I really liked how they wrote, they were putting out like regular blog-like content, were Tim Urban who writes Wait But Why, and then Morgan Housel who's a partner for Collaborative Fund, an author, and he writes like a blog on their site. Um, I just like their voices. I liked how Tim— I liked how he broke stuff down. He used very casual language to explain like really big picture stuff from black holes to why do people procrastinate, but he drew stick figures on all his stuff. And the art was terrible, but like it was his style. And then Morgan was taking this really quantitative thing, finance, and writing very un— like very qualitative pieces about it. But everybody else was like breaking down like earnings per share and like what's the revenue growth going to be. And he was talking about like human behavior, but how it relates to money. And I kind of took some stuff from both of them and then just injected my own voice. Like I'm a almost sarcastic bro-y type of like voice when you read my stuff. Yeah, but pulled it all together and that's what it turned into. But it was because I really liked reading their content and then it just clicked that I should probably write the stuff that I like to read and then to get the tone right. And then I, I just kind of realized that I would rather write about just broader stuff that I'm thinking about than pigeonholing myself and like writing about stocks or personal finance or whatever. Like a lot of my stuff relates to like career-related stuff or money, but I just didn't want to get stuck in this little hole where this is the only thing I can write about forever. But it was a matter of like the pieces that were the more philosophical pieces were the ones that like people were like sharing on Twitter before I had a big audience. So it was just taking it. I never had this like master plan. It was just you're subconsciously thinking all this stuff through, getting this feedback, seeing the content you like, and then it all comes together and turns into what you produce.

Mm-hmm. Oh man, this is such an interesting point, which is like I think when you say the traditional employment game, yeah, uh, a big part of the appeal is like the certainty, and every step is clearly laid out. So it's like, you go to these set of universities, going to those universities allows you to then apply to this set of jobs. Once you've done those jobs for like 2 years, you can then do this next set of jobs, like literally like 5 to 10 years in the future. Everything is mapped out. And so I think for people who are used to being like high achievers and like working on something and they're used to getting a result from it, there's something very comforting about knowing like, if I put in the work, get the grades, I'll get this result. If I work here and do well—

Drew one of, uh, Drew like a graphic that basically exemplifies it. I've used this a couple of times, but it's like, uh, it's literally like, that's the path. Yeah.

Yeah. And so I think you mentioned like the first 3 to 4 months you were almost finding your style. Yeah. And I think, I think the thing that like scares a lot of people, um, and the reason why even though the traditional kind of work game might not be for them, they stick with it, is because at least I know what I'm getting here. Yeah. And so I'm curious from your perspective, like those first 3 months As someone who was like at one point fully bought into the traditional game, like what did that even feel like? Were you like, oh fuck, like this is not working? Or you were just like, I'm just gonna keep doing it?

Like what would be— honestly, I was just having fun with it. But there's, there's a caveat where my, my floor or my risk at that point, I, I, it was basically risk-free for me to take a shot because I knew that almost as an insurance policy I was going to a very good business school in a year. So I was giving myself one year to just try a bunch of stuff knowing that I could fall back on, like, my worst-case scenario realistically was having a job that's gonna pay me like a quarter million dollars 3 years from then, as long as I did the business school thing. So I had 1 year to just try a bunch of stuff knowing that, like, I basically couldn't lose at that point, and I had enough disposable income that I also wasn't gonna run out of money until I got to that point. So it was like I didn't really have a financial risk because I, like, I wasn't just gonna go blow like $100,000 in a year. Like, I was pretty thrifty. So I knew that my money was going to be fine. I knew my career options were going to be fine. So I didn't do this like burn the ships, I'm going to make this work or bust. Like, I had a fallback plan. So for me, it wasn't— I mean, I would get frustrated at times, you know, I would write stuff and I felt like I was getting no traction, but it was never like an existential fear. Um, and that's another thing where I've kind of been a little more introspective on the value of traditional employment, is that Having a regular stable job buys you the time to try other stuff. Like, if you have— if you know that you have a salary coming in, you're making $100,000 a year, and you have maybe 10 hours of free time per week, like a couple of hours a day to work on your own thing, you could work that regular job for like 3 or 4 years while you're building up. It could be like building your own business, a side hustle. It could be blogging, podcasting, whatever. And you don't have to quit that regular job until, say, your income from this other thing replaces like 70% of your job income, where you're comfortable enough that you can cover your living expenses and go all in. It was just like my time in the traditional world had— like, I was like, I was trading stocks during that, right? Like, I didn't realize this until later, but that was kind of my first side hustle. I wouldn't recommend that people do that. It was just I was bored at home on my computer, but that was me. That was the equivalent of me working on like building out a blog or newsletter or whatever. I was doing that, and that made enough money to buy me the freedom to do this other thing. Otherwise it wouldn't have happened. So I think that, uh, that's what gets missed on this. People are saying go all in on the entrepreneurship or you have to do the job. It's like nobody should ever just quit without being in a spot where they could go a year without working. Like if you're, if you're gonna quit, you either need to have a lot of money saved up so you can go in on it, or you need to keep like a revenue stream or an income stream coming so you can experiment with other things. Because when you do that, if you need money too soon, you'll make decisions that might be bad in the long term for your side thing, trying to monetize too soon. Like I I'm probably under-monetizing all the stuff I'm doing just because I haven't needed to like really put my foot on the gas to make more money, which is gonna be a lot more upside 5 years from now. Mm-hmm.

You know what? And it's like, this is actually the last point you made in your, your article, and like I'm literally experiencing this right now. Yeah. When I left my job, I was like, and this is just kind of my personality, is I have like full faith in my abilities. So I was like, give me like 3, you know, like if I'm working on this full-time because I've been doing the podcast for like a year. Yeah. Uh, I'd already started kind of starting an agency to do like podcasting services as well. I was like, you give me like 3 to 6 months doing this full time, it's gonna work. Yeah, bro, this shit always takes longer than you think. Yeah. And it's difficult. And I think, you know what the, the thing is, I think sometimes the internet can get us messed up because you see these like videos on YouTube of like 'Oh, I made $20,000 in 30 days,' and it might even be true, but a lot of the time what that video is missing is all of the context. It's like the 6 other businesses you started before that which completely bombed, but you learned like the exact framework so that you could actually go and apply it and make that amount of money in that time. Um, I want, I want to get into that from your perspective, like Talk about it just taking longer than you expected to work.

So there's a, there's like a pretty good graphic by Jack Butcher that like floats all over the internet now, but it's like this to like, like describe it audibly. It's like this, like it's like a line graph and it doesn't go up and it's this quote saying, this is pointless right before it turns exponential. But that's how it works. Like as soon as stuff starts popping off, it happens quick, but it takes like, say, say it takes 2 years to hit that point. The first 1 year and probably 9 months it isn't going to, from the outside, look like anything's different, but you're building up a foundation where once you take off, it happens. But yeah, the internet does screw everything up. Like when everybody wanted to get rich quick trading stocks, because you're seeing on Twitter and Reddit, like somebody made like $500,000 on Tesla options and you're missing the 99% of people who got blown up and lost all their money doing that. Or like some people have scaled newsletters and podcasts really quickly, Um, like one example that I wrote about my last piece was the Milk Road was a crypto newsletter. They went from 0 to 250,000 readers in less than a year and sold it for millions of dollars. But Sean Peery had a very successful podcast he was already doing. He had already sold— like, he was one of the founders of Milk Road. He'd already sold a startup or two and had money where he could afford to go in on this. And nobody was really like— Morning Brew and The Hustle were big newsletters that had sold,. But nobody had said, I'm going to make a newsletter about a specific hot topic and put out the daily news every day. Like there wasn't another crypto newsletter doing that, but everybody's seen that playbook now. So all these people are like, oh, it's so easy. Like I can do this with like AI is the new hot topic. There's probably 50 AI newsletters all doing the same thing and it's not going to work because they're all trying to sell the same ad sponsorship slots and the rates, like they aren't getting the same ad prices as they would have if there was just one of them getting all the audience. It's all diluted and it's not as straightforward like that. That path doesn't work anymore. So people see the one-off successes, like you said, they'll miss the context. And then also, if everybody catches on to the same trend at the same time, it doesn't work. Like, you had Sahil Bloom on, on one of your podcast episodes. He was one of the first guys to really lean into the doing the threads on Twitter and all that. And his stuff stood out because the content was good, but not that many people were doing that. But everybody's been trying to copy it where it just looks like cheap engagement bait. But he's already built up a big newsletter and all these businesses on the side. Like, he already won that Twitter thread content game before it became popular and basically got out of it. Um, so yeah, I mean, people get late to a trend. If you're early, you can do it quick, but you have to be like the first one to do that. Otherwise, it's going to be a grind, and you basically just have to outlast other people. That's where I'm at now. Like, I'm not going to get a million readers overnight, but I'm at 43,000. It's growing quickly. But it's because I'm not trying to like get rich quick with it.

Mm-hmm. You know what? I love the, I love the example of Sean with the Milk Road. Yeah, because there's so many levels to the context that people miss, right? So even if you just take the skill set of being able to write, I did Sean's Power Writing course. Okay. Like the, the writing course he did about how to go like viral on Twitter and how to write like effectively. And communicate effectively on the internet. And this guy like really knows his stuff when it comes to like writing in a way that people want to read. So it's not even just that he got the right topic, it's like his skill set was sharp to the point that he could actually execute on the opportunity. And then also, if you also add on to that, his co-host on My First Million is Sam Parr. Who built, uh, The Hustle and sold that for millions. So it's also like he— and he probably has a lot of other people in his network who have also built and sold newsletters. So it's not just that his skill set is on point, it's not just that he literally, um, he almost found like a blue ocean, like he found like a market where there wasn't really anyone doing content in that way. So it was like opportunity plus skill set plus network of like expertise. Like, this is the playbook of how you build a newsletter and then sell it, like in detail. All of those things came together, and that's why with a ton of work put on top of it— like, they were— it was daily, right?

Like, yeah, it was every day.

Yeah, they're putting it out every day, which is a bunch of work. Um, all of those things had to come together for him to have like a multi-million dollar exit from that newsletter.

And it was also all these crypto companies had so much money, they were just throwing— like, they paying a lot of money for ads, like a lot more than they are now. I saw a thread yesterday from like, like there's a lot of newsletter people I follow on Twitter, but about how everybody's doing these AI newsletters, but advertisers just aren't paying the same like CPM that they would have a year and a half ago for crypto ads. And it's like just because you both have 100,000 subscribers, one person can be making like $6,000 an ad, one could be making like $1,500. And that's also going to change how much somebody is going to buy your newsletter for if you're trying to sell it. And people are missing all that, like the market conditions matter too. I mean, there are so many things that lined up well with Sean, and then he also executed perfectly that you could run that playbook, he could run the exact same playbook and it wouldn't have the same end result at this point because the situation's different.

Yeah, and you know what it brings to mind for me is because, you know what, people might hear that and they might be like, oh, so we got like lucky. And it's not that because I think from doing this podcast and having conversations, um, with a lot of like successful entrepreneurs, what you find is that they stay in the arena. So like they stay in the game. Yeah. So like they're either producing content, but they're kind of in— they're like on the ground floor like doing stuff. So they're gonna see it early. Like they're gonna see— because he's writing and he's putting stuff out and even has he has his own like personal newsletter even away from the crypto one. So because he's always putting stuff out into like into the ecosystem, if there is an opportunity, he's gonna see it first versus the person who's like just waiting for the opportunity but isn't writing or isn't publishing, right, or isn't really having conversations with other entrepreneurs or like people in those spaces. You're gonna see it late when it gets shown to everyone else, and by then it's too late. Um, so it's also a lesson of like, and, and that's why what you're doing is good, which is like you're in the game, like you're publishing stuff all the time. So if there is an opportunity, not only have you already honed the skill set to write, but you're gonna see it first. Yeah. And like, I think that's one of the key things that I've learned kind of in this last year, which is it's almost like you have to spend a lot of time like waiting and just like in preparation. Yeah. And then every now and then there's going to be an opportunity. And the people that make it big, they really capitalize on that opportunity. They almost like steal a bunch of like market share, build this thing, and then they're able to kind of capitalize on that however they want.

I had like a comparison to that. I played football, American football in college, and it's one of those things where like when you're practicing, you're like playing out all these scenarios because you never know exactly what play the other team's going to do. But if you're like ready for it, you like that's That's where like the touchdowns, the sacks, and the big plays happen. It's because you've gotten all the reps in, you've been prepared the whole time. So the stuff that looks effortless on the field, like there's so much going on in the background that allows them to do that. Like it's the same thing with succeeding as an entrepreneur. It's like all those little reps just stack on top of each other. So when you do strike, your like chance of hitting a home run or being successful are just exponentially higher than if you just weren't preparing in the background.

You know, it's, um, and it's interesting as well because obviously Netflix, um, just released this series Quarterback. Yeah. And it's interesting seeing like the behind the scenes of Patrick Mahomes and like, because obviously the Chiefs do like some of these crazy plays, right? Like these underhand passes or like just these weird kind of off-the-wall plays. But they're like practicing that stuff and they might not even have practiced it really for that week, but something that they've just put a ton of preparation in and tried and like done extra reps after practice. It's useful for like one moment in one specific game, but sometimes that's the difference. That's the difference between making it through like the divisional round and getting, um, we're getting through the AFC Championship to get to the Super Bowl and not making it. Yeah. Uh, like it's fine lines, especially at the elite level. Yeah.

Um, you were, uh, you were talking about one of your other podcasts how you're a big LeBron James fan. I think it was with Sahil. It was— you were talking about like that Finals loss against the Mavs. Um, but like when they won against the Spurs, that Ray Allen 3— I don't know if you've seen the interviews where he's talking about like how many times he practiced that exact very just random scenario of like catching the ball off a rebound and being able to set his feet behind the 3-point line without having to look. But that ends up like winning them an NBA championship because it was one of those very niche, odd, like probably never going to happen in a game, but it could. And yeah, it's just like that with Mahomes and with the quarterback series. It's insane how much work goes into things that probably won't happen, because they could.

Mm. Man, it's just interesting, 'cause, like, that is really what separates, like, the best, right? Is that they're kind of ready for every scenario. Um, and I think a lot of it comes back to what we were saying at the beginning, is they just love the game. So, for Patrick Mahomes to do, like, a few extra plays at the end of practice, is easy because he loves playing football. For LeBron to, like, practice some weird niche, like, scenario and set a play in basketball, he loves playing basketball, so it's, like, natural for him to do that. Um, and that, that's just gonna play out when you get to those, like, those marginal moments. Um, okay, here's, here's where I want to go, because I think one thing I like about your story is it combines two things, right? You're doing the thing that you like and showing up as your authentic self, which is nice. And it's like, it's refreshing to see that on the internet. Behind the scenes, you are still able to monetize to a certain degree. Yeah. And like I don't know if you're living like the baller-ass lifestyle that like you dreamed of yet, but like you're, you're living in Manhattan and like things are happening. And so we've kind of spoken about how your, your content creation journey and like even the way that you show up and producing that content. I want to talk about the other side of it, which is like the monetization piece. Yeah. And how you make it work in your life so that you can, you can be patient with the content. So speak to me— obviously we spoke about like the first 3 or 4 months you were kind of figuring out the content stuff. At what point did that monetization piece on the writing start to come into play?

So I had a, like, looking back, pretty ignorant idea of how easy it would be to make money with this. There's, um, I'm pretty good friends with them now, but Packy McCormick has a popular newsletter, Not Not Boring, where he writes like a couple of pieces a week on like all sorts of— it's stuff ranging from like breakdowns about companies he thinks are interesting to just trends in like technology and business and whatever. Like, um, and his stuff's good. Like I've been reading his newsletter Not Boring for a couple of years now, but maybe a year and a half ago he had like 35,000 subscribers, like a little bit smaller than mine is now. And companies were paying him like pretty good money. I remember reading on another newsletter or like in an interview seeing what rates he was charging for ads, and he was making like, I don't know, like $2,000 or $2,500 per ad on like 30-something thousand readers. And I was like, that seems like a lot. And then companies were also paying him, I don't know if it was like, and I might have the numbers wrong on this, but like $5,000 or $6,000 for like a sponsored deep dive article where a startup that has like an interesting story wants to get some publicity and also have a piece put out that they can then reshare with their networks. And they would pay him to write a piece about them. He would disclose the whole thing, and he was very open that like he wouldn't write about a company that he wouldn't personally invest in. And he did invest in a lot of these companies. Like there wasn't, there wasn't anything nefarious about it. And he wrote that— there's a very thin line between like taking money for content and keeping it authentic, but he did a very good job of like being very open with everything. But he was making good money from those like sponsored pieces. And I was like, okay, if I can get a newsletter to like, I don't know, 10,000 readers, like I could probably make $1,000 an ad at that point, 2 times a week. That's like $100,000. Maybe somebody would pay me to do like sponsored content, and then it'd be like maybe $3,000 or $4,000 apiece for doing one of those a month. And I'm like, 10,000 readers, maybe I'm making like $140,000. Yeah, that's not how that works at all. But that's what I thought when, when the blog started going. I was like, people are doing this right now. What I missed, like with him for example, was he had built this audience of people very interested in like tech and startups and all that. So like companies were gonna pay him for this type of content because they knew his audience were also the type of people who would invest in these startups or use the products or whatever. Well, I have a much more just general audience interested in my content, but it's not like all these guys are like venture capitalists and this and that. So I completely just didn't even look at the context of that. And like there's, there's no value in me publishing like a business breakdown of a company on Young Money because that's not what people are reading my stuff stuff for. It might— it just wouldn't fit. But I did think that that's what I was going to do. And honestly, that ignorance was probably what got me through the first 6 months because I was like, like, I'm not making money yet, but once I get like 10,000 readers, it's going to be a cash cow. Yeah. But I did— the one thing that helped was, um, Liquidity, which is this big finance meme page that started on Instagram and Twitter that has like probably 1.5 million followers between Instagram and Twitter at this point. Um, it was just an anonymous meme page started by this guy who was working for like an investment bank or private equity firm, and his concept was funny. It was very niche finance humor, but it was good. Like, people who work in finance loved it. And we had just been messaging on Twitter randomly because I found a Spotify playlist called Happensday Sauce. I was playing it at a pool party like 2 years ago, messaged him, told him playlist was good, and then he was like Thanks, you have any song recommendations? And I said, yeah, here's like 10. Um, and then we just were literally chatting about Spotify playlist songs for a pool party playlist for like a month. I launched my blog again, not knowing where I was going to go with it. I see that he has this big finance newsletter called Exec Sum, and I'm looking at it and it has like venture capital, mergers and acquisitions, deal flow, like all the big news headlines from Bloomberg and Reuters. Earnings recaps and some memes at the bottom. And I figured it was probably pretty big. And I'd also just gotten a client from this job offer with Morning Brew. So I figured Morning Brew is like a fully established company. Liquidity is a finance meme page who has a newsletter, but I see he has ads on it, so it must be a business. So I messaged him and I was like, hey, do you want help with your newsletter? And he was like, what do you mean? And I was like, maybe I could write like weekend pieces, I could help edit it, I could do whatever. And he was like, Um, yeah, I mean, I'll pay you like $500 a week to help edit this. And at that point I was just hostel hopping in Europe. So $500 a week, that covers when I'm spending $15 a night on a bunk bed in a room with 10 people. That works. So that, that can cover my cost of living. So I was like, yeah, I'm down. And when I started working for him, I got to see kind of the inside look on how he's negotiating ad contracts and making this much money and this and that. And that's when I saw, like really saw how the business worked from the inside. And I was like, okay, my idea of basically copying Paki McCormick isn't going to work, but if I get a big enough audience, I can still monetize with ads. I can also keep working with him and doing stuff with him. And I ended up pitching this idea of doing these business deep dives like Paki was doing on ExecSum because his audience made sense. ExecSum had a bunch of bankers, people working in finance reading it. Where a company would probably pay decent money to get the exposure to that audience. We've done like, like we just published one on this like asset management platform called Gridline that lets you invest in like private assets, nonpublic assets. And like I, like I write that piece, I get like a 30% revenue cut for those for doing the writing. We publish on this platform, but I pitched the idea that like I was going to do on mine to him because it made more sense. He didn't have the time or bandwidth to write these, but it was a pretty easy sell. It's like, hey, you're going to keep the majority of the money. I'll still get decent money for it. It's valuable for your audience because they're going to learn about like a cool, interesting company and it gets exposure for the sponsor. So it all works. So as far as the business side, like I'm still editing that newsletter, still occasionally doing those like sponsored long-form pieces. And then I'm also monetizing Young Money with ads, but I'm not making— like living in Atlanta, I would be fine, but like living in New York, going out, traveling a good bit, I literally need both. To like, or I would just spend too much money. So that's like, that's the thing that gets missed. Most creators probably have some other revenue stream that isn't their main image. Like ExecSum is my version of a day job where I do a lot of administrative stuff, help negotiate the ad stuff, and like I'm making, I'm making about $60K from that plus like whatever upside I get from sponsored stuff or ads that I sell. Then I'm selling ads on my newsletter for like $1,200 or $1,300 a pop. And I've slowed down to doing one a week. But between both of those, that's like, I don't know, like $120,000. And then there's a lot of other random variable stuff that bumps up on top of that. But having multiple revenue streams makes it where it's a lot more sustainable. Like, I have like a good enough paying job between all of it to like afford my lifestyle, but it's because I'm doing a lot of different stuff. And I would say most people early on are doing a lot of different stuff. Like, any creator that isn't just like already like a best-selling author or has a podcast with hundreds of thousands of downloads a month probably is doing like one-off project work or something to like make more money because it's hard to make money on this stuff.

Yeah, you know, um, oh no, I like this a lot. And, and the— I remember when I, when I left my job, um, he's come on the podcast and he's also just like a friend and like he gives me advice as well, uh, Ayman Al-Abdullah. So he was the former CEO of AppSumo. Okay, um and I remember when I told him I left my job, he told me— he gave me a piece of advice which is so true. He was like, in this like first year, year or two, your, your only thing you're trying to do is just survive. Yeah. Like once you leave your job, the thing that you don't want to do is have to go back to your job. So you just need to like find little creative ways to like, okay, can make like $1,000 doing this. And he was basically saying you want to focus on doing things that are kind of like adjacent to your main thing. So obviously your main thing is podcasting. Like, what are some like adjacent services or like some holes that you can fill maybe for other podcasts so that you can just survive long enough?

Yeah.

Um, and the whole framework of it is kind of like, this content thing is gonna be a really like long game. Yeah. Like even though we've spoken to like quite a few content creators at this point. I feel like the tipping point is like 5 years minimum. Yeah. For them to like really be making like a lot of progress with just content, it is like 5 years of consistently putting stuff out. Um, and obviously it depends on the medium as well. Like if you go podcasting, might even be longer, um, because of like the growth cycles that happen there. Um, but it's so important just to like be surviving and be like scrappy in that time. I think the second piece of what you said, which is interesting, um, is the fact that, uh, you kind of learned from these other people, like you kind of learned the business of newsletters. Um, and I guess like, I, I'm kind of interested to go deeper into how someone can even kind of get those opportunities or start to get those relationships where, like, because I feel like with creators as well, a lot of the time you don't actually hear a ton of information about how they're really making their money, right? Like, you don't really hear, like, how they're negotiating deals. And maybe you'll hear, like, how much they made, but you won't hear why they were able to charge that much and, like, what went into it. Um, So maybe you can kind of, you can kind of speak to that because I think there's a lot of people who will be listening and they want to do something creative that they care about. Um, but they also want it to be realistic in the sense of like, I'm still making money. Like, I'm not just like living in my mom's basement typing newsletters or like recording podcasts. Um, so what was kind of, what do you think were some of the keys where like you even managed to get those opportunities? To even like sit next to someone that's like kind of running a successful newsletter?

I mean, for me it was tell somebody you like their Spotify playlist and start chatting. But it's, it really is like, that's a very niche anecdote, but like honestly, just being friendly and putting yourself out there. Like you never know in real life when you're just going to start talking to someone who's doing something interesting and then it builds on top of something you're doing. For example, like with my scenario with talking to Liquidity, if I hadn't already been writing a finance blog, I wouldn't have gotten that because he asked me, he's like, do you have any experience like publishing stuff online? And I was like, yeah, like I'm writing this finance blog. I've done some freelance articles. Like I didn't know the business side of a newsletter per se, but like I knew how to like produce clean content that was well organized and put it out. So you could say it was lucky finding that opportunity, but I still don't get it if I wasn't already in a spot that he would have been willing to take a shot with me. Like, I was a very low-risk person because I already knew at least how to publish stuff online. Like, I wasn't completely starting from zero. So it's one of those things where if you have an interest, you just need to go ahead and start doing it. Like, people want to map out a perfect plan. It's much better to start doing that thing, and then when opportunities come up, you just have to take them. But I do think you can kind of like manufacture your luck a little bit by where you put yourself. Like, for me, being very active on Twitter, I I'm more likely to see an opportunity where I can reply to somebody's tweet or message somebody when somebody needs help with something and get my foot in the door. Living in New York City, you are much more likely to have those like encounters that turn into something because there's just so much going on here. If you were trying to like climb the ladder in politics, you should live in DC and be around Capitol Hill. Startup scene, go to San Francisco. Um, for the content thing, like you have to start producing content even if you're getting literally like no listens, no views, whatever. Because if I see that somebody's published 100 blog posts, even if they have like 100 readers, I know that they can put stuff out. Where, say, like, I'm not, I'm not looking to bring anyone on to help me right now, but if I was, if somebody had proven that they could put that much content out and their stuff was clean, as long as I like them as a person, I'm probably down to work with them. If somebody has all these ideas but they don't have any proof of work, it's a massive red flag. I don't want to see a resume, I want to see I want to see stuff that you've actually done. And that's how it was with me with Liquidity. It's like, here, like read these 3 blog posts, tell me what you think. He was like, you're in. Um, so yeah, it really is like, it's, uh, you have to like do some of the work first and then you just have to throw yourself out there at opportunities. And like, I, I probably applied to like 15 writing jobs and didn't get any of them, but this thing with Liquidity stuck and then it just turned into more and more and more. Um, but yeah, it's a combination of just putting yourself out there and actually like just producing content.

Yeah. You know, you know what I was thinking is actually so interesting because we started this conversation by talking about like the traditional work game. And if you think about the structure of that, right? Like even if you wanted to get a job, say in investment banking or consulting, you go through, you do like a bunch of, uh, preparation. So when I was doing consulting, yeah. Uh, you do like all of these case interviews. It's almost like you're practicing like theory of like how to be a good consultant. So you'll just spend a lot of time like preparing and then, um, you get into the interview and I guess it's like your chance to show that you can do more of the theory or that you understood it, but they don't actually know that you're good at the job until you're literally in there. I think this reverses it's almost like a 180, like it's the complete opposite. You need to put a ton of work and actually like show the— prove that you can do the thing a bunch of times before you get any opportunity. But then when your opportunity does come, you're going to be one of the few people that can actually capitalize. Because the thing is, even in your situation, like how many people on the internet, um your moat was in your consistency. Yeah. And in your— in the work that you've done. Like, how many people on the internet would have been able to reach out to that person and be like, oh yeah, I've been publishing blog articles on the exact topics that you would want. Yeah. For months and months. Like, there's probably like hundreds, or like, there's, there's so much work that you can look at. And that's your moat, that's your differentiator, that's how you get your foot in the door. Nothing. That's such a good— I think it's such a good, like, lesson for people. Um, here's where I want to go next. So you're like, uh, your posts like crush it on LinkedIn. I'm just curious, like, what's your, what's your thoughts on LinkedIn? And then also, um, why do you think that, like, your style is just like kind of tearing it up there?

So I— this whole thing started as a joke. And for context, for anybody who has no idea what we're talking about, um, I basically just post satirical content on LinkedIn a few times a week. And it tends to blow up because there's a— if most, most people are on LinkedIn, pretty much everybody has an account because if like, if you're trying to apply for a job, everybody looks at your LinkedIn for your employment history. Like you have to have a LinkedIn to be like professional, especially in any kind of white collar role. But nobody can post anything with any kind of personality on LinkedIn because God forbid you post something a little bit controversial and that prevents you from getting hired. So every single post on there is just people congratulating people for jobs or posting stuff directly related to work, except for the, like, serial— what I call, like, hustle bros that are acting like this whole entrepreneur mindset, but they're really trying to sell you something. It's either like a supplement or a pyramid scheme, like coaching business type of course. My favorite one is the ones who are like coaches who tell you how to be an entrepreneur so you can go coach other people. It's like the— it's like the male version of, like, when, like, a lot of women were doing the Herbalife. Stuff like that was big a few years ago and it's just annoying. It's like you have to escape the 9 to 5 grind, this or that, or people giving like— there's a weird amount of people on LinkedIn that'll like just do anything they can to get LinkedIn clout, like talk about missing their kids' birthdays because they're trying to provide for their family. And it's like, you're not like— you're not a tougher worker. You're just a bad father. Like, come on. But people have no shame on there. So after I quit my job, I had no, like, grand plan with it. I just thought it would be funny to start making fun of those type of posts. So like, I posted this long one. About how I was applying for— this was like 2 years ago, it was the first time I did this. Yeah, it was— I think I copy and pasted it from somewhere else, but how I was like going to a job interview and I saw a dog get hit by a car and I took the dog to the vet and saved its life. And then I had to call the office and say that I was late for the interview because I had to save this dog. And I walk in, guess who's interviewing me? The dog. And it's like, just— it was so stupid, but it kind of blew up. And then I was just sporadically doing stuff like that. Like, I was saving money on my water bill every month by showering with my clothes on so I didn't have to wash clothes separately. It was so stupid. But when it became a thing where it's like, wait, there's actually a little bit of value in doing this other than just entertaining myself. Um, some of my friends had started, like, I had a pretty big network of people on Twitter going into last fall. And then a few of them were like, hey, we would all just rag on LinkedIn. Like, we hated LinkedIn. We thought it sucked. Like, it was the butt end of every joke on Twitter. And a couple of them were like, there's no good content on LinkedIn. And it is really easy to grow a following there and leverage that to get people to buy your products, read your newsletter, do whatever. Because Twitter has so much noise. Everybody's going for engagement on Twitter. There's just not much content on LinkedIn. And I was like, shit, that makes sense. Um, this guy, Daniel Murray, I went on his podcast, uh, Marketing Millennial and his like, like podcast LinkedIn page has like 100,000 followers. And he's just posting like— it's like a lot of it's just screenshots of his tweets, right? Like, it's not like it's taking that much time to do this. So then I was like, all right, I want to get big on LinkedIn. I don't want to do the cringe thing. Maybe if I can just be sarcastic enough, I can still get a big following just off of being funny, which there's gonna be like long-term effects of that where I might get like 1,000 new followers from a funny post. But then those people are following me, and when I post like blog posts or actual like real stuff later, that's more eyeballs that will see that stuff too. So there's like a lot of long-term value in building an audience from anything. And if it's sarcastic content, they already start getting introduced to my voice where while the blog post might not be sarcastic, it still sounds like me. So I say all that to say, I've now been just ripping the most ridiculous scenarios. Like I put one on LinkedIn yesterday that ended up with me saying, like asking them, like thinking it's ridiculous that I have to pay a tip at Starbucks. Telling the barista, I don't think I should tip them, but they should come up with what the tip amount would be. And they tipped themselves $15,000 because it would make me work harder if I paid that much. It was stupid and it blew up. I put a screenshot of it on Twitter and it's got like 10,000 likes and people in the comment section like, this definitely didn't happen. Like, no shit, this didn't happen. You were completely missing that you were part of the joke in this. But it all works to get more eyeballs on my stuff. Without me having to just like— I think humor is a very high level of thinking because if people get it, they almost automatically like you because they think you're funny because you made them laugh. And if people don't get it and then they reply on it, a lot of their network's going to see it through them getting angry about it. So it just really accidentally became a phenomenal engagement growth tactic. But the, like, the whole, like, point of it is I now have like 30,000 LinkedIn followers. And I get a decent amount of newsletter subs from LinkedIn now. I've gotten to the point that I have people emailing me asking if I will write a sponsored LinkedIn shitpost that like promotes their company, which I'm thinking about. I'm going to start doing. I never thought that would be a business thing, but if somebody wants to pay me $1,000 to do a LinkedIn post and it's funny, it's— there's no difference between that and Barstool Sports doing like funny videos that are advertising for like High Noon or something like that. So yeah, I mean, if I can monetize my LinkedIn account directly, that's just another positive from the whole thing.

Yeah, you know what, that is actually— that is actually a skill set that like businesses want, right? Because I'm even thinking, even if you think about like Wendy's, like I think I see like all of their social media.

Oh, they're funny. Yeah, yeah, great. Ryanair is one of my favorites. The Ryanair Twitter account is insane.

Yeah. Um, but to be honest, you know what's interesting as well actually, because I think some of the best marketers online, they've kind of realized that, uh, kind of the nature of the internet is like people like to like dunk on other people. Oh yeah. So they realized that and then they figured out how to like use that almost. It's like a growth engagement hack. And, um, I remember someone was actually talking about Drake and how he does this, like even with like his album covers or like some of his dancing and like stuff he'll do. It will be like kind of cringy, corny, and then people will just be like posting it, or they'll make memes on like his album cover, and it's like free distribution. Oh yeah. And everyone's like, oh, like he's like a dork or whatever, like he just looks like— he's just like lame or whatever, but he's getting all of this like publicity, like you're promoting his shit. Um, I think the thing is, I think the thing with you, like you really understand like the internet and kind of like how to make things go viral and like to create pieces that people will talk about in a good way or a bad way, but people are going to talk. Um, I'm curious, take me behind the scenes of that process. Like when it even comes to the barista post, like how are you even like brainstorming that idea? Like what's going in behind the scenes?

It's not really like, like an active strategy. Like I don't really have a brainstorming session, but there's just stuff that I'll I'll see— it's a combination of like, I'm either terminally online or I'm just on Twitter or LinkedIn 24/7, or like, I'm out and about in the city. Like, I don't have— unless I am sitting down actively writing stuff, like, I'm not just chilling in my apartment that much. So I'm just seeing a lot of stuff. And like, I've noticed over the last really post-COVID, everything has a tipping option now, like stuff that didn't used to. It started as a like, business is slow, we should tip more. And then it just kind of stuck. Like 3 years ago, you weren't tipping to walk up and grab a coffee and leave from Starbucks. Like, tipping was kind of a service thing. It's like now, like, sometimes you get an option to tip at McDonald's, you know what I mean? Like, that just wasn't a thing. And it's become like a joke where, like, where, um, like, I've seen stuff where it said, wow, like, I just got the option to tip on the screen on the back of my airplane seat for, like, like, being able to, like, watch movies on it. Like, stuff like that. It became a thing where people are just joking about it. Or my landlord just gave me this iPad and said to tip for rent. So that whole idea of like making jokes about tipping culture going crazy, it's just kind of a thing online right now. Um, and then on LinkedIn specifically, there's, there's just, it's, it's an evergreen, like really bad personal finance advice that people try to posit as good personal finance advice. And I just kind of combined both of them, but you think it's going to turn into this thing where I don't tip them or I leave like a negative tip to keep more money or something like that., but then I'd put a twist in it where they took themselves $15,000 to make me grind harder. So it almost, it wasn't like an active thing. I just started writing it and it was like, oh, this could be a funny plot twist. What can I do with this? And somebody's probably going to believe this anyway, even though it's so ridiculous. Um, I really think it's just, I've done like probably 100 of these and I've just kind of gotten in a groove of like, I just kind of know what stuff goes viral on LinkedIn. And then I know if I post a screenshot of it on Twitter, Everybody on Twitter loves to just shit on LinkedIn, which just makes it blow up on Twitter. So it's a win-win.

Yeah, yeah. I'm curious, like, in the— when the— like, the first few ones you did, would they just completely, like, bomb? Like, did you have any that were like—

I wouldn't say they bombed, but it's just when you have like 500 LinkedIn followers, it's people you know, you'll get 20 likes and people screenshot and say, this is funny, but what is this? But once you get to about 5,000 and 10,000, I mean, stuff can go nuclear because there's just enough touchpoints that can blow up. But I think the first time I did one, I think I actually still had a job. I had a normal 9-to-5 job at UPS, and I think I posted the thing about— I think I was still working when I did the one about the dog interviewing me, and my actual boss called me and she was like, this is hysterical, but also like, what is this? And are you applying for other jobs? And I was like, no, I just, I just got bored and thought this was funny. Um, I just never really had any shame in it. What the weird thing about the internet is, once you have a big enough audience, you can really get away with anything. Like, as long as I don't just tweet something that's literally just like misogynistic or racist or something like that, like, I can say some edgy or just weird stuff and it's like, oh, it's a bit, like, it's part of his thing. Yeah, if you have 500 followers and you do that, it's like, wow, this guy's really weird. But if you have 55,000 followers, it's like, I don't get what he's doing, but There must be a method to the madness or he wouldn't have this many people following him. So I just kind of had to get through that like cringe valley of where it's like, what is he doing? To, oh my god, it worked. Yeah, there's no bridge across that. You just have to go all the way down and all the way back up.

Yeah, you know what, you know what? That's an interesting point. And I think, you know what it is? It's things change when you're doing it for like an audience or you're doing it for a crowd. Yeah, then it's entertainment. Yeah, if you're just doing it, no one is responding, then it's like, oh no, this is what this guy actually thinks. So like, this is what he's actually saying. It's, it's no longer entertainment because no one's being entertained. Yeah. Um, okay, you know what, there's, there's two things I want to touch on before we go. The first is, um, and it's kind of funny, so like obviously, um, those two articles, so like kind of the Five Career Create Things, and then the category of one. Um, when I read those, I was like, okay, I need to talk to this guy. Um, and then like, that's almost like the basis of my research and like my understanding of what you've done. But then I'll just start going like down a rabbit hole on YouTube and like seeing like little shorts and like bits and like podcast stuff that you've done. Um, and one of the videos I saw was you talking about losing $150,000.

Oh yeah, that's my favorite story.

Well, since you're so fond of it, let's get into it. How did you lose $150,000? It was $150,000 in a day, right?

Yeah, it was— the specific number was like $100— I think it was $152,872 in like 4 seconds. I mean, it was like the market opened and it was gone. And I knew it was gonna happen. Like, I knew it was like watching a countdown, and I knew I was about to get massacred. Yeah, um, the backstory to that was a lot of people traded stocks during COVID because like, I mean, there was just so much stuff going crazy from tech stocks to crypto to GameStop to whatever. Um, I found these things called SPACs, and I'm not gonna do like a whole 5-minute super detailed breakdown on the mechanics of them. Yeah, but they were their own little bubble, and they were basically an alternative method for companies that were private to go public versus doing a regular IPO or something like that. And there was, there was, there was a bubble there, and a lot of these were just like going up 100%, 200%, 300% for no reason. And I just caught on to that trend really quick. Like, we were talking about these like newsletter trends and stuff like that. It was the same thing. I was just really early on it and was willing to put some money behind it. I was like, okay, I have— I did this in my retirement account. I was like, I have $6,000 in my Roth IRA. If I lose $6,000, like like, yeah, I mean, that sucks, but that's not gonna like kill me. It's whatever. This— that was a gamble I was willing to make. I turned that into like $20,000. I was like, all right. And then $40,000, $60,000, $100,000, $150,000. Then I start taking a lot safer trades. I'm still playing these SPACs. This was in like— this was all within like a 9-month period. So I'm like, okay, I'm only gonna take stuff where I know I can't lose more than 10%. Like, I knew where there was like— like, I could redeem my money for X price. On these stocks no matter what. So like, I never risk more than like 10% of what I'm investing after that. So I'll go all in with like $200,000 knowing the most I can lose is $20,000 and then sell it once I make $20,000 or $30,000. And then it was just a parlay after parlay. But then the bubble popped. I didn't lose money when it popped because again, I was managing my risk. As degenerate as it sounds, I had a very calculated process up to this point that worked, and I was aware that it it was working. But then that game didn't work anymore. Like, I wouldn't have lost money trading those, but like, they just weren't going up anymore, basically. But when you go from $6,000 to $400,000 in like 9 months, you don't sit there and think, wow, like, I just made $400 grand, it's all tax-free because it's in a retirement account. I could cash out, pull like $100K out, pay a little penalty, and just like have a year— like, it's up $300,000 growing tax-free. That's what I should have done. My dad knew what I was up to. He said, you're a dumbass if you don't at least just take half of it off. He's like, yo, just go crazy with like $150K. Go, you're 23, 24, go do your thing. But like, you could leave a quarter million dollars in an index fund, never have to save a penny for retirement. I said, yeah, but if you make 6— I'm up 6,000% in 9 months, another 150%, I'm a millionaire. How cool would that be? So I just start throwing money at random options and this and that, or companies that like went public through SPACs and they were now publicly traded. But with all these trades, I didn't have that like floor. Like, I— anything that I put money in after this point could theoretically go to zero. And I just thought that some company was undervalued based off of all their financials and stuff compared to other companies. And on paper, I was right until they had their earnings report in August 2021. It turns out that they missed their own estimates by like 30%. All of a sudden they weren't really that undervalued anymore. They're kind of overvalued, and the stock dropped like 40% on that earnings report. And I had like $300,000 in that stock, and there wasn't a lot of liquidity trading in like the pre-market hours before the market opened. So I sold a little bit of it, but I was like, damn, I'm about to have to liquidate like $100,000 worth of this right at 9:30 a.m. And I know that I'm gonna be the one who takes the price, but I was like, but if I hold it, it's just somebody else is gonna do it. So I just put in an order to just liquidate all of it when the bell opened, and my account went from like $300K to like $150K like that. And I was looking at that and I was like, well, I was visiting one of my best friends in Pittsburgh and he knew what was going on. He came out and he was like, are you good? And I was like, yep. I was like, I'm just going to keep this in cash for a couple of days. I think I'm done trading and I'm about to go to the gym for like 4 hours. That was the best workout I've ever gotten in my life. It was, but it was okay. It was a, The one silver lining is I still did make money overall, like $6K to like $140K or whatever. Isn't bad. Like, I'll take that. And because I'd made and lost it, being able to cash out and also realizing at that point, like, alright, I just looked back and realized I'd spent like every waking moment just trading stocks, thinking about trading stocks, and then I blew like over half of it. I just realized I could have spent the next 5 years doing this and taking it to zero. And then what? Like, this is, this is a net net win. Like, I have a good bit of money. Like, I've got a pretty solid, like, nest egg for retirement that I'm never going to touch. And I learned a lot about myself, about, like, the whole, like, psychology behind money and all that stuff. Um, I mean, yeah, it was net positive, but it hurts losing when you're making, like, $60K a year and you blow, like, $150K in a day. That's, that's a tough one to wrap your head around.

Yeah, for sure, for sure. And I think, um, Bro, knowing when to stop is such a big thing, isn't it? Yeah, but it's so hard because when you're, when you're winning and you're on a win streak, like, that's the last thing on your mind. Um, you know what, I think one of the things, uh, one of the things that's cool, like, sitting, uh, sitting here with you is you're just like having fun with it. Oh yeah, like, uh, if whether it's the shitposting, whether it's the content stuff, whether it's the newsletter, whether it's the investing, you're just having a ton of fun with that and like sharing it. And so I guess my final question to you is, um, like, where does this all go? Like, what is the culmination of, I don't know, your investing background with the content, with the funny posts on LinkedIn? Like, in your mind, is there like a vision of like, this will all lead to this, or is it more so, I'm just having fun with this thing, man, and like, we'll see what happens?

Yeah, I mean, the Right now I look at it like I have one more year of business school and I almost intentionally don't want to like hyper-commit to anything that's a massive time commitment, like, like quote-unquote traditional job, just because I want to fully enjoy this, like being in school, being with my friends, doing this and that. Like, I like this point of life, but most of the people that are in my social group are about to in a year be back on full-time jobs and stuff, which is when I will not like I'm already all in on this, but we'll have a lot more time to fully commit to the like kind of work side of all this. I'm making enough money right now that I can support my lifestyle. I'm not like saving much more than I'm spending, but like it works. And I know that this is for one more year thing, but continuing to build like a LinkedIn audience, Twitter audience, a newsletter following, there's so many ways that pays dividends where if I want to start a company or if someone wants to hire me in a role where I'm like producing a lot of content, I'm, I'm becoming a more and more valuable asset just by building a bigger and bigger audience. If I want to write a book, like, I've talked to some publishing houses a little bit, and having a big mailing list is how you secure a much bigger advance on a book. They're more likely to say yes. So I don't know for sure what it would look like, like, if I wanted to ever launch a podcast with somebody. I've got a big enough audience that I would be starting at a much higher level than, like, from scratch. Um, I don't know. I mean, the biggest thing is I like writing, I like talking about stuff. I mean, I plan on to some extent keeping my blog, newsletter, whatever you want to call it, going forever. Because one, I like writing stuff and owning my own platform where I have full creative freedom to write whatever. And also I own that email list where that gives me— like, just owning your own distribution list is so valuable for literally anything. And I wouldn't do anything where I would have to give that up or sell that or whatever, because that is like just a permanent call option on just getting eyeballs and stuff I'm doing, which is valuable. But it could be continuing to just do my own thing, like blog, newsletter. You can monetize that with ads. I could add a paywall and like add more content and have like a subscription method. It might be doing some freelancing stuff. Maybe it is going to like work for somebody where I'm still producing a lot of content as sort of their marketing stuff. I don't really know, but it's— I'm at a spot now where like I have options and know I'm gonna have more options as as it goes. So it's, it's a very convenient place to be in because I don't have to say yes to anything. So if there's something where I'm like, yeah, like the money makes sense, the opportunity makes sense, like the amount of like hands-off freedom I'll have makes sense, I'd like to work with these people, yeah, I would, I would take something. It has to fit like every aspect of what I'm doing because I don't really need anything right now, which is a good spot to be in.

Yeah, you know what, you're, you're in a great spot. And I think it's, it's like, it's great to see, which is like you have a lot of options before you and things are working, like the flywheel is working, like you're building the audience and the audience is now feeding like all of those different options that you have on the table. If I was to say just a moment where it was not working, or you were just kind of like down on your luck, or you were just like I don't know if this is gonna pan out. Is there a moment that comes to mind when I say that where you're like, the flywheel was almost working the other way? Like, it didn't seem like there was any traction, and because there was no traction, it meant that there was none of these other opportunities.

Yeah.

Was there a moment that just springs to mind for you where you're like, yeah, it wasn't working?

There was, it was fairly early on, but not like a week after I started, like right when I like launched this newsletter, I'd put all over Twitter, LinkedIn, Instagram, like told my friends. I didn't have like a big following. It was like a very normal, just people I knew. But a lot of people knew I was very into the stock market and this and that. So like, I think like 200 people signed up initially just to see what I had to say. And then it just really didn't grow from there for a while. Like it did a little bit, like people were like sharing the stuff, but I hit a point where like I would get like like 3 new readers, 5 new readers a week, and then I would lose that many when I published. So I was just sitting at net zero and I've been talking to Liquidity about working with him, but it just like, we hadn't really, like, it was a, oh yeah, like let's chat. And then our schedules didn't line up and this and that. And it was probably late October, early November of 2021. And I started this thing in July or August. So I'd been doing it for 4 or 5 months and I just had no idea how to grow it. Like I didn't even know what I was doing. I didn't know, cause I didn't start working with lit, like really full time until that December. So I almost just figured, okay, I guess I'll keep traveling for this year, like keep going around doing my thing. And then like when business school starts, I'll go get a job or whatever. And then like on top of that, Columbia University called me and with like the kind of rules or whatever for me to start my business school studies there, where normally with an MBA you have to work a few years before you start business school. For my specific thing, like normally you would work and then apply. I got in out of undergrad. They had a deferred enrollment cohort where you would get in and then work a few years. And then on contingency that you worked a few years, you would start. I only worked 18 months before I quit my job and I was supposed to work 2 full years. So the newsletter stuff hasn't really taken off. And then Columbia's admissions office calls me and they're like, hey, we think you need to defer another year because you've only worked 18 months. Because I had to send an employment update. So I was kind of like, oh shit, I might have screwed up so bad. Um, but I sent them back like a, like a, like 2,500-word email basically explaining that a big part of the reason I quit my job was during COVID there just wasn't anything going on. And then like most financial analysts were just essentially acting like they were working for the majority of the time. And I was like, I at the time thought I might try to work for a hedge fund or something. I was like, I've detailed here, here, and here, and sent links to blog posts about how I explained my trading strategy. I was like, I could talk to a hedge fund manager and explain the intricacies of like the SPAC trades I was making, but I have enough money saved up. It is a much better value for my time to go out and see the world a little bit, meet interesting people, have these experiences, and bring a lot broader perspective into business school than me like looking at spreadsheets all year. And then they emailed me back and they're like, okay, yeah, you can go and come next fall. And then on the blog side of it, um, this guy Nick Majuli, who works for Ritholtz Wealth Management, we're, we're pretty good friends now, but he'd had like 100,000 followers on Twitter, had a big finance blog. He'd been writing for like 5 years. He put this piece out about why it's dangerous to actively like invest in individual stocks and like trade versus index funds or like more longer-term investments. And I just replied to the tweet and I was like, yeah, I have a personal story about this. I blew like $150,000. Here's the story. And I just replied to it and he messaged me on Twitter and he was like like, dude, this is insane. Do you care if I share this on Twitter and like in my newsletter? And I was like, nah, please do. And I had like 400 subs at that point. I got 250 in a day just from him sharing that. And all this happened within like a 2-week period. So it went from, I didn't know if I was getting into business school, no momentum's happening with this, this and that, to the growth thing clicked where I was like, okay, this guy who's already won the game likes my stuff. I just need to interact more with like bigger accounts on Twitter. That are doing what I'm doing. Not in a, hey, please retweet me, but in a, hey, I wrote something related to this thing that you're talking about. So I was like, I didn't know what I was gonna do. And then I realized that like the, my near-term growth path was just being like very interactive and communicating a lot on Twitter and just getting a lot more eyeballs on my stuff. And I, it worked. That was literally, that's what happened. But yeah, I mean, there was like a week or two there where I just did, the writing wasn't working. I didn't know if I was gonna get into Columbia. Like I thought I was gonna have to go get another job for a year at some point. Um, so yeah, that was definitely the kind of rock bottom of the whole thing where I romanticized this, I'm gonna travel and write, and then I was like, oh shit, like this actually probably isn't gonna work. And then it did.

You know what, and just to, just to end, for the, for the person who's in that moment, they're in that moment where like they've made almost like a strategic risk, like they've made a bet. Yeah, and it just doesn't seem like it's working. And they're, they're trying, they're trying different things, they're continuing to, to stay at it, to keep going, um, but they have no clarity on the path and things are just not working. And they're almost— they're not working in a few different ways. So the way that for you it was like, it was almost like the newsletter not working plus Colombia. Like when it stops working in like multiple ways it just hits you harder. You just start to feel this. It's like the reverse momentum. Yeah. Like the amazing momentum you feel when the flywheel is working and you have all these options. What if that was put in reverse and like things are not working and they all seem to not be working together? If you could give the person, and you know what, maybe I'll frame it like this. If you could give the Jack who was in that moment just like a word of advice or like something? Because I think when you're going through a hard time, it's important to just to almost bring things back to the foundation and just focus. So if you were just to be like, just pay attention to this, or like just focus on this, or hold on to this word of advice, what would you tell that person that's going through that moment?

I think, I think there's two things. Um, one, exercise, which seems like completely unrelated, but honest to God, like actually just staying active keeps your head clear to actually— because you— that, that negative flywheel, when you start stressing, then you start sleeping bad, not eating well, not exercising, and then you're just in a bad mental space. You can't even like figure this stuff out if you're not right with that. But then the other thing is like, it's— I also heard Sahil Bloom talk about this, but the Tim Ferriss fear setting thing, just sitting down and writing out, okay, if all this implodes and none of it works, what's my worst-case scenario right now? And like, I did that when I was there. I was like, okay, Okay, if I don't get into Columbia and my newsletter doesn't take off, what's the worst case scenario? Go back, get a job for a year, and then go to Columbia a year later. I would've been 26 going into a good business school. And then on top of that, that would give me another year to keep working on my stuff in the background before that. It would've set me back a year, but it wouldn't have been like the end of the world. Like I still could keep traveling for that year, reapply to a job that summer, explain that I took like basically 9-month sabbatical given the circumstances I was in coming outta COVID. I would be able to get a job then. And once I realized my worst-case scenario was just having a stable job for a year and still like being able to like start at Columbia a year later, even if the newsletter thing didn't work, it just lowered the stakes a lot where it's like, all right, like, well, let's keep chugging away at this thing because if you get to a point where like you're going to need money in 4 months, you'll be able to go get a job. So yeah, like, like for me, it's like exercising just to like be in a good enough mental place to actually think that stuff through without your mind going going to worst case scenario, it's over, and then actually writing out what that worst case scenario looks like. Like, I wasn't going to end up like homeless under a bridge, completely just out of money. Like, that, that just wasn't actually a realistic outcome to any of this. So once you see that your worst case scenario really isn't that bad, it makes it a lot easier to objectively chart a path forward.

Hmm. Nah, that's real, man. It's been a pleasure having you on.

Yeah, man, I appreciate it.

If you enjoyed this episode, please subscribe to the channel.. We're having fire conversations every week on the podcast. Before we end the episode, a quick word from our sponsor, Free Agency. What if I told you there is a good chance you're leaving money on the table in your career? It would kind of annoy you a bit, right? Well, Free Agency aims to stop that. They represent and manage talent in the tech industry. Here's how they do it. First, they provide you with a dedicated talent agent. Think about this as your career quarterback. They understand you and your career goals. Based on that understanding, They bring you suitable interviews at top firms. You focus on smashing the interview, and together with their network, research, negotiation expertise, they will make sure you get a top-of-market salary. Stop job searching alone and start building your dream career today with Free Agency.