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Why your cold emails aren't paying off (ft. Marshall Kosloff)

from Best of Luck with Kyla Scanlon

43m 29s

Why your cold emails aren't paying off (ft. Marshall Kosloff)

Marshall Kosslock shares a deep, practical philosophy for building careers and networks in a shifting economy. He emphasizes that true connection is rooted in genuine interest, not titles or formal hierarchy—he walks up to influential figures, shares personal insights about their work, and invites them to informal meetings. His approach is grounded in authenticity and curiosity, where he focuses on people’s potential and projects, not just their credentials. He highlights that career success often comes from taking bold, unconventional leaps—like leaving a stable job to pursue a creative path—while maintaining a safety net through side work. Marshall critiques outdated norms such as unpaid internships and rigid academic paths, advocating instead for self-directed learning and creating a personal body of work through interviews, writing, and public engagement. He stresses that risk is not about jumping without preparation, but about having a foundation and being open to redirecting one’s path. Central to his philosophy is the idea that real value is found in deep, project-based connections, not surface-level exposure. He also cautions against measuring worth by views or clicks, noting that true value lies in meaningful dialogue and shared vision. Ultimately, Marshall’s journey reveals that career building is less about luck and more about preparation, resilience, and the courage to follow one’s instincts—even when they go against tradition.

Transcription

8608 Words, 45343 Characters

English
I look at people based on their potential and what they're interested in, rather than any specific title. There are people who have fancy titles who are boring, there are people who are in turns who are very interesting. Marshall Kosslock is the best networker I have ever met. He just knows everyone. He is really good at building long lasting connections, and it has really paid off his career. Everyone tells you it's who you know, but nobody tells you how to get to know anyone. Welcome to Best of Luck, a show about building a career in an economy where the rules keep on changing. I'm Kyla Skinland, and every week I ask one big question about work, to someone I know can answer it in this episode. How do you build a network on your own from scratch? Support for the show comes from Alpha Space by Yahoo Finance. If you're an investor looking to make smarter, faster decisions, look no further than Alpha Space by Yahoo Finance. Alpha Space is an investment charting and analysis platform built for sophisticated individual investors looking to find the data, market tracking, and news that matters all in one place. You can explore Alpha Space with a Yahoo Finance Gold subscription, and right now your first year is 50% off. Head to Yahoo Finance.com/Kyla. Build as $239.70 for the first year, then $479.40 thereafter. Offer valid for news subscribers in the U.S. Offer ends December 31st, 2026. Marshall has a few official titles. He hosts the realignment, and he's a senior fellow hands-on director, special projects at the news scanner and sensor. I think Tank and DC. For he focuses on how to make the government actually work. But before all that, like all of us, he had a first job. My first actual job was as a model at Abercrombian Fitch in 2011-2012, but it was funny because the word model has actual implications. Because if you were a model, it sounds super cool. You get the card when you're shopping, but what actually is happening is that means that there are regulatory implications to being a model versus a sales associate, so it means that they could fire you based on your looks at other things like that. So it's like a very funny, like you sort of take a step back and look at the world, and there's a dynamic there. Quick recap on his 20s. After college, Marshall moved the DC and did a two-week Think Tank program, then an internship, then a fellowship. Then you took on an entry-level research job in journalism. He worked for PBS on firing line with Margaret Hoover. He didn't love the job. By his own admission, he wasn't too good at it, but he was on the journalism ladder. Researcher today, producer tomorrow, maybe a big network one day, he could have kept climbing. But then he thought about who was actually watching. Well, what I was thinking when I wasn't doing my research work was, wait a second, this is airing at 8.30 pm on Fridays. On PBS, the idea of it, there's any person under the age of 40 who's watching this is like near zero. So what would it look like to build a show of its premise on the same idea of exchanging ideas between different sides, but putting it on a platform that actually matters? So that's when my actual work time was spent doing rather than actual research. He decided to leave to try to build a career of his own in the world of politics and policy. How did you get brave enough to jump? I care, and this is both like a. I was talking about this for my life before I recording what I'm thinking about my life and the role of it luck plays in a career. If you just sort of reset me to 2009 and said, "Hey, Marshall, you know all these things, you know all this direction, you know, take that direction and get to where you are now. I don't think I could pull it off." So there was like a lot of luck there, but I think my personality, which is one that's contrarian, I like doing my own thing, I'm confident in the ways that I'm bright just gave me a lot of resilience because you just have to get really, it's not just that you have to get used to people saying no to you, which is always going to happen in any career or in any life, but you have to just get used to people saying, "I'm not just saying no," because like I can't make this coffee or like this job isn't quite the right job right now. There are no high rings that are open. It's like not only am I saying no, but actually what you're doing is wrong and I actually don't understand what you're doing while you're doing and I'm worried about you. But I just had the resilience because of my personality to sort of just keep pushing past that, but it's also a danger because, and this is why my 20s were kind of difficult because so much of that overconfidence, which is really like if you don't have the experience, you don't have the knowledge and it's just instinct, like that's going to verge from confidence over confidence very easily. It's sort of the, you know, it's a meme now, but it's like the picture of a War 2 bomber but has all like the holes through it. And this sort of idea was like, wow, the bomber made it through and like what you're missing is the fact that like, actually a lot of the bombers didn't make it back. That's how I feel like when you're talking about the things that I'm saying here. Yeah, like almost as survivors. Yeah, there's just like a real business like 99 versions of me that didn't make it through those sort of moments. But I think the things that I've cared the most about is I've always cared about ideas and I've always cared about reading and sort of like thinking about things. So even when I was doing these like short term tactical mistakes, like I probably should have worked harder at that entry level research or job on as hell as you show, I should have actually showed up with more energy and direction and work. What really mattered was that I was like, oh wow, if I work very, very, very hard at a job in traditional media and follow the researcher roles, I'm actually not going to end up where I want to end up. So it's okay that I'm short term under investing. And instead I'm thinking like, oh wow, don't worry about the researcher job. Realize that like you have an opportunity to learn about media, which then led me into podcasting where I'm doing it on my own and taking lessons from that. And I think one thing that impresses me the most about you is you're such a convener of people. I feel like you know everybody and you knew the Vice President. You had JD Vance on your podcast. So how did you, how did you do that? Yes, so that was my, so my first episode on that did from a then co-host Saga and Jenny who hosts breaking points on on YouTube. So JD was our first episode. And I actually met him kind of right as the book came out. He'll be allergy right when he's sort of becoming famous. And I've been thinking about this law because like the thing about my career is that I live in like, it's not just that I do 10 different things is that I live in like 10 different worlds. And something that I've been thinking harder. So like that means tech philanthropy media, the world of think tanks of events like the Aspen Ideas Festival. I've been thinking more about less the specific ideas that these spaces describe and more the ways that these spaces are structured and the sort of social norms in them. So heads up. Marshall is going to talk about the left and the right. This is not a politic segment, but he is going to talk about how he sees rooms being built, who lets who in and who makes time for the intern. This is his perspective and his experience. So I was on the right in the really to mid 2010. So and I need to be very precise about this. This is the only sort of political thing I would say like when I say like the right, I'm not referring to the Republican party because these are kind of two different things because like one is about elections. The other is like an ideological thing so it's like a movement space. So movement spaces are really cool because they're rooted in ideas. Therefore you can basically in any movement space meet big people just by expressing ideas. So if you're in 2015, 2016 and you're just saying like, was this on Twitter? Yeah, no, this is just like in person. So how do you even get in the room? So the origin story here is Ryan Salam is the president of the Manhattan Institute now, but back in 2014, 2015 he was actually my age now. And he had just been appointed executive editor of National Review Magazine and there was a New York magazine piece on him called like Brooklyn's coolest conservative. And I'd read a book of his back in high school and I was at a Google policy event in DC. And I just walked up to him and I was like, Hey, Ryan, like great to meet you. I read your book back in high school. I read all the work you do. And then just sort of went to leave because like when you meet anyone in person, you have to do the like it's like when you meet a celebrity, it's like and these are intellectual thing takes celebrities, but you have to just like you go in, you go out, you're wearing their time. So I went to turn and he was sort of just like, No, like, let's talk. Why are you? He's like, what's up on the phone? And then he gave me an hour of his time. And then he was like, by the way, I meet lots of young people. So I'm hosting people for tacos like next week when I'm back in DC. So let's meet up then. So that was like a really important model for me in terms of how you should interact with other people. And the sense of like just being genuinely interested in people regardless of like their hierarchy because like, and this is why I was saying like idea spaces are different than party spaces. I didn't even have an internship at that point. I was just like in DC after college. Nobody, but just like this person invested time and energy in me. So that's always taught me to be very just like anti-higher article in the sense of like, I look at people based on their potential and like what they're interested in rather than like any specific title. There are people who have fancy titles who are boring. There are people who are interns who are very interesting. So he then introduced me to JD. So this is the Marshall Kostloff method. As far as I can tell, walk up to the scary famous person, say something about their work, leave before it becomes awkward and get invited for tacos. Which raises a question that I had for him because I've never really done that. I'm a digital person and I started my career in a much different pandemic world than he did. Marshall is a lesson for now and a time where we can be in person again. So I assumed Marshall would have never had the problem that I have, which is being really nervous but but he does. How he gets over that after the break. One thing that you've done is you've gone up to people and you've shook in hands. You're very brave in that way. Like somebody like me, I get a bit more nervous when I have to go and introduce myself to people. And I actually built my career pretty much entirely online at first, and then I started going to all these spaces. But it sounds like for you, it was opposite way, where you went to these spaces first, then use online world to build it out a bit more. Is that right? - Yeah, and I think it's, this is where we get into sort of the valley, part of my career, because like I was weirdly, I was weirdly the most confident, like in that 2015, 2016 period, so just like walking up to someone, 'cause I didn't know what I didn't know. But the other problem with thinking is structurally as I do, is that I very quickly fall into over-observing and then overthinking things. And I just thought about things so much that I lost my ability because it was really funny, 'cause like I said, I was a not even in turn mediocre student who's showing up in DC. I'm just like walking up to someone, just being confident. But in the mid-2020s, and you notice about Creator Word, it's like very democratic and then anyone could listen. But there is just like a hierarchy, and there are dynamics, and there are just sort of reviews. So what started to happen to me is I started to be like, man, like that video you did last week, it just did not perform. So if you walk up to this person, they're gonna like maybe have a good interaction with you, and then they're going to like look you up, and they're gonna see that your views were lower, and then they're gonna sort of like not think well of you. So like what I was sort of like working towards is just sort of like rebuilding within reason, the whole point of like hey, like actually, you should just be confident, you should just talk to people like you're nice, you're warm, you're friendly. And-- - And you convince yourself. Like do you say that in the mirror? Like every morning, do you repeat it after my session? - I think I said that to me. I said that to myself like a month ago, I had like a long conversation about this. - With you? - With myself, like I was just like thinking, journaling, not doing, you know. - No, I talked to myself. - In the mirror, so I talked to myself about this, but then like that's where the advice was just like, but stop talking to yourself. So that's where the whole thing was like, your problem was not thinking hard about things. It was actually you not just directing that towards action. And then there's also just like the very obvious you were in the salon in an elementary school, but you had to really understand this in a 30 something, 20 something context of like, but actually, Marshall, any person who would, 'cause this is the problem. There are people, you know this, who would like look up, look you up, and then see low performing video and then decide not worth my time. But the actual conclusion is that is not my person. And your person is a person who would not, my person is a person who would not care about viewcans or just be like, oh, like Marshall said something interesting. During that conversation, that's separate from his viewcans. - I love this perspective because in our world currently, we do judge people by views and clicks. And while I have you, please share and subscribe and give us three thumbs up. But as Marshall says, if a person judges you based off of that, they might just not be your person, which brings me to my next question. Is knowing people a skill? - It is a skill, but it's also a practice where you, knowing people comes naturally to me, but it's actually something that anyone can do. - Are you an extrovert? - I'm an introverted extrovert. So this is actually why I think I really resonate with you, because I sort of have like the, I walk into a room and then I'll just be meeting people but then I'll just like go back to my hotel from like six to like 11 and just like be by myself and I'm totally okay with that. But I think anyone else like, this is the really, really, really good news where you know this, like things are so in-person now after like, you know, that COVID period and that like post-COVID period where just being interested genuinely and other people. So like when you see that part, this is the key thing of like when I'm at Rihon. It wasn't just that I said, "Hey, I saw you in New York magazine saying you're super cool." And that's just like obvious. I read his book in high school and I'm like, I was prepped to talk about it. So if like youth, if you think hard about the space that you're in and you like read that if you need to read, you was into the podcast scene but you don't just like listen to the podcast, you like think about it, anyone can do that. 'Cause that's just showing interest in a person and I think genuine, interesting people could overcome any degree of lack of charisma, shyness, et cetera. - Everything Marshall says requires you to be somewhere in a room, meaning flights and hotels and expenses. A lot of us can't do that for a variety of reasons. I had the same issue. - Yeah, what about for someone, like someone say, like for me, for example, I was in Kentucky. I didn't know a lot of people. I wasn't really able to go to DC or anything like that. 'Cause I graduated 2019 and then spent most of my career in the pandemic, right, building the beginning of it. Do you recommend that people send these cold emails to folks and ask say it on the phone if they're in that sort of situation? - So it's really, really, really hard. And this isn't even just about like the earlier part of the conversation we were talking about, like ideology in this side and that side, this is actually more about the space that you're in. So there are certain spaces where a cold email is just going to work. So like when I was up, I think my intern was, my email was AEI intern one. And I just like emailed like a bunch of scholars like asking just to like meet and they just met. So like this exists in a lot of different industries. There are just spaces where like people are interested in other people, especially young people. And the key thing was like this wasn't just the famous, like can I pick your brain? Can I get coffee, which is just like, there's no industry where like that's a good email to send. I just like worked really hard to like craft like a paragraph. They would like capture their interest and like reflect that like this is a person you can meet with who's like interest. What's again, this kind of back to like interest in people. - Those be specific questions about their work. - It's, this is what it is. It's less questions about their work. If you email an academic or a scholar or an expert and say like, I actually read your book, which they expect like only 200 people at best to have read their line as like my friends and family didn't even read this book. And if you ask them a specific question about that work, this also applies to creative. So like what say there's like a filmmaker who did a film and like no one watched this film. They will be interested and will answer those questions by I think of the most people, they get plenty of time to talk about their work. But if you think hard and structurally, like not just like their work, but what project is this work furthering? So like the way I would think about this is like, okay, so for you as a creator, what say I just wanted to, I'm not trying to sort of throw your name out there for advice. This also applies to me. I wouldn't just like ask about an episode or a specific topic. I would actually say listening, having read to what you're working on, I'm really interested in my career is directed towards this longer term project that I suspect you are interested in. Where do you see this project going? Where could I fit into this project? Like those different things. For example, I remember at the end of your book, you said, for example, I think abundance is an interesting idea. - Before the abundance book are written, yes. - Then yeah, I'm giving up, this is not advice. But this is everything. I would have done this in 2024, if I were an intern, I would have said like, actually not even as an intern, but just like me being a random person in DC, you said, you know, abundance could be, you said could be, I could interestingly go down and I co-produced the annual abundance conference. Or like I'm involved in, there are young people, I would say like, hey Kyla, I think abundance is sort of like missing the ball on this or that. And I think that you've actually gotten this thing correct. I'm curious how you think this sort of work that I'm doing and that like maybe you're interested in, could like fit in, or were there people who like you met, who right after you wrote that end of chapter, I've reached out to you 'cause I'd love to connect with them. Like that's directing a coffee, a meeting, an email towards like a project that in of itself is interesting rather than saying like, hey Kyla on page 10, you said this, like what did you mean by that? 'Cause you just get so many emails that like, it's hard for you to answer all those things. So that's the way, that's why I sort of like pitch for how you should think about reaching out to someone. - Don't ask about people's work, but ask about their project, what their work is in service of. Don't pick brains, offer away for them to think alongside you. Now we're going to go back to the question I ask everyone. The peak, valley and cliff. Every career on this show has a cliff. The moment you jump and can't really see the bottom. Marshall's is recent. And it wasn't taking a risk, it was turning one down. We're gonna finish the section on the cliff. And so my cliff actually happened at the same company that we were working for, we worked for a startup during the pandemic. And I left that startup to start my current job, which is financial education. And that was my cliff. Like where I took this huge leap into the unknown. And so what was your huge leap into the unknown? - So my huge leap, I'm not gonna name names here, but the venture firm reached out for me to work for them in a high profile, really, really relevant job. And the money was great. It was straightforward. No more 1099 contractor things. Just like a straightforward thing. And the leap I had to take was, in many ways, content creation was on paper. My goal was to get into institutions. Because I had weak grades because I wasn't like a good, early career worker, I never. I could have gotten into venture, or finally, - And you're young. - Yeah, one of my 20s. I never could have gotten that. So me using my creator journey, over seven years to get that offer, was a real accomplishment. - A nutrition path. - Yeah, non-traditional path. And it was like a real, like that was one of the things I'd thought really, really, really hard about, which is like you wanna be in these institutions, but you need to do on your own terms, not on the other person's terms. But I just realized that A, I wasn't interested in the work. And there were limits to what I could do if I wasn't an institution. So part of my like talking to myself conversation was, hey, pat yourself on the head, you did it. You did it, but actually, how much of you staying is about comfort and simplicity? And ego, and I told you so to the bosses, you said you'd never succeed. And once I framed it in those terms, I was sort of like, no, it isn't what you wanna do. What you wanna do is still be a creator. This is the thing I'll say too. I've, this is when I really push down people on. I think we are very bad at understanding risk. I think you, in so many spaces, for philanthropy, like early careers, like people really talk about risk. And my entire career was promised on when there was a risk point. I took the risk. And what I think people don't think about, and this is where me being overly analytical or thinking about structure really matters, whenever I take risks though, I make sure that I've got, you know, a base of support in a foundation. And I just noticed that people don't do that. So for example, like, I just wanted to get a podcast starting in 2018. And part of what I was doing at PPS was I was fundraising to start my podcast. And like meeting people and finding a thing to think they would host me. That's kind of why I wasn't doing a great job with my day job. But I didn't just say, okay, Marshall, are you in legacy media or are you a podcaster? I built a job that I held. And then I like, in my free time and my work time, my work to do that. And I just see so many young people would just sort of see it as either more. So even my cliff was not like, as much of the cliff as you think. And I think people always by not thinking hard about the problem, just like don't say to themselves, like, what does risk actually mean? And what is my ability to take a risk, quote unquote, will also not actually taking a risk? Yeah, like how do you build a safe, you know, self? Yep. And for you, that was having two jobs at once, like a side hustle, yeah. And then meeting an institutional job. Yeah. Yeah. Do you recommend people do that now? 100% because the thing, and this is the thing too, we're like, so much of what's hard right now is as employees. Employers don't have an incentive to like tell employees this and like your mentors, Cornico, cable, but in a different world, don't have the ability to say this. Yeah, very difficult. You have more levers than you think to say, "Hey, this is how I want things to go." So Marshall's secret for taking risks is don't take them, build the next thing while you have the current thing. Never let anyone make you choose before you have to. It's good advice and something that we heard from Kai Ristle too, but now onto some bad advice. Marshall has been given plenty after the break. A story has been waiting a decade to tell. Support for the show comes from Office Space by Yahoo Finance. You shouldn't have to juggle a bunch of random tools and tabs to manage your investments. Alpha Space by Yahoo Finance brings everything together in one easy to use platform. With advanced charting, real-time market data, in-depth Yahoo Finance news, and insights all in one place. You can spend less time searching for information and more time making informed investment decisions. Powered by Yahoo Scout, Alpha Space by Yahoo Finance is a one-stop platform that lets you build personalized dashboard around stocks, turns and data you want to follow, synced with your portfolio for real-time tracking. I really appreciate the news aggregator on Alpha Space by Yahoo Finance. As somebody who reads a lot of news, it makes sure that I'm not missing anything. You can explore Alpha Space with the Yahoo Finance Gold subscription, and right now your first year is 50% off. Head to Yahoo Finance dot com slash Kyla, that's Yahoo Finance dot com slash Kyla. Build as 239 dollars and 70 cents for the first year, then 479 dollars and 40 cents thereafter. Offer valid for news subscribers in the US. - We're gonna talk about some advice that you've been given in the past. So what is the worst advice that you've ever been given? - I've been waiting 10 years to tell this story. The worst advice I've ever been given is, so after I did my internship, I did a two-year like rotational fellowship program where you would go to a think tank and a media organization into Philanthropy to like learn about like conservative spaces in DC, and at my philanthropic job, I was working on Excel spreadsheets and I was terrible at this job in Excel. I was terrible, it was sloppy, and during my quarterly review, I was sort of brought in, and the managers of the fellowship, and this is where bad advice is so dangerous because it's even more dangerous when people are acting in good faith. - Yeah. - You know, so I got the sort of slap on the wrist yellow card for doing poorly at my job, but as an end of the day, they just sort of said like, hey, we think you're so much promised, we're trying to level with you. You have to ask yourself, how are you going to make money at 31 if you cannot do Excel spreadsheets? - Were you that bad at them? - I was that bad at them. - Oh my gosh. It's not even the like, I just wasn't trying. I wasn't trying. I was focused on it, I was reading articles online, and the thing was, totally good faith, totally rational. It's actually very rational to say like, if you look at everyone else and they said, look at ourselves, we have these big deal jobs now. Eventually you're going to run out of fellowships to do, you're going to wake up at 28 and want us to help you find a job, and we're going to know, Marshall can't do spreadsheets. The problem though was, in no way, should my time have been allocated to doing spreadsheets. Because the way we've talked about me like, I'm Marshall, I'm friendly, I'm an in person, I think about people, I think what were people sort of spaced, I think something about our hierarchy, and this was even on the right. So this is me not claiming the right is like perfect on these things. I think because there's such in a, at least in the time, there was such an established path of where you follow a bit like, because the people who tend to run programs, or run HR departments, they are people who follow the rules and follow the path, they really struggle with even conceiving of people who have alternate paths open to them or have personalities that just aren't fit, but are still incredibly useful. So the actual advice that should have been given was not, hey, Marshall, get better at Excel. Get better at Excel, so you could make a living at 31. The advice should have been, okay, where to be open-minded, how do you see yourself being successful at 31? If you are not doing spreadsheets, just try to path-risk. I actually had thoughts, like I had a plan, I had thoughts. So my whole point here is that, like employers, talent agencies, like that's about gray-overly, like talent agencies where it's sort of like the idea of like, talent should go a specific place, like there's an ecosystem. So what I want people to give advice to give is sort of like, especially in an era where there are so many options in the like whole structured path as the weakest has ever been, have the humility to say. More likely than not, I might probably correct. This is like my point where like 99 out of a hundred times, like actually I should have gotten better at spreadsheets, but like what would have been useful for me and still applies, even in a world where I'm doing better at spreadsheets, you say, I could have said, well, I want to launch a podcast, or I want to like, so should we organize people, or I want to like run like a placement program or this or that, then they could have either said, like, wow, Marshall, you're totally right. Here's where we're going to do a switch you out of the spreadsheets thing and put you towards something that actually lets you do that. So you could just maximize yourself now, or they could have said, actually that's really interesting. So let's reframe it. Need you to lock in for the next six months of your of your fellowship. And if you lock in and we reframe this from, Marshall needs to be an Excel Maven too. Marshall actually can work really, really hard and can take feedback. I'm going to work really hard to get you in the next opportunity, but it's actually more structured to your actual point. So like humility and open mindedness about people's key. - What's some good advice that you've ignored? - So in 2010, I was, you know, my mediocre, like flunk out of college student type, and I loved to throw parties. Like that is like my, I threw what parents out of town, like after the best parties in high school. So like when I got to college, I immediately, you know, people are underage drinking, and I was throwing a party. And we got caught by campus PD, and I was getting written up, and I was doing like the meeting for social probation at my university, and at the end of the meeting. 'Cause we just had like a very kind of conversation like this, and the sort of administration official was like, you know, is that actually got an impressive what you did with this like college party? I hope that you can use your powers for good and towards something productive. And I thought I took that like, and this is why I become more analytical, I just took that like, kind of literally like, yeah man, I took it seriously, like yeah, like, you're obviously effing around, you need to apply yourself. That's how I interpreted it. But what it actually kind of meant if you took it very literally and analytically was the only thing that motivated you this entire semester was like throwing a freshman year dorm party that brought eight dorms together. And I actually like, hopefully. filled. I was excited. I got out of bed. I was motivated, didn't need like caffeine or like nicotine to get it done. And now so much of what I do is like convene and I throw events and I work in events and for context like Aspen. So the actual takeaway was like using my powers for good and not evil was dude, stop trying to be a think tank walk. Because actually most of my think tank walk is like my deal is that like I understand think tank walks and I read the work that they read. But like it's not actually me writing the research paper. So now it's just sort of like wait using that power for good means become an event producer and convene people and think about how you could build spaces that are conducive and helpful. But I didn't figure that out until two years ago. And like that's where I have some at six that's not because I'm applying a skill that I thought was just like a lifestyle or fun thing to like you know that's a career that you can do. You can party for a career. Party for a career. So I wish I wish it was a very very very good advice that I wish I'd like taken a little more. Okay, wish I'd gone home to my journal and said like what would it look like? To be on the like banking yourself to like use this ability you have towards something pro social and towards like a career. The spreadsheet people told him to be less like himself. The dean of students told him to be more like himself. He heard both stop messing around but messing around is where the beauty happens. We're going to talk about breaking some traditions. So you kind of touched on this throughout the interview but we're going to talk about what still works with these things when it works and when people should think about skipping it. So what do you think about grad school? Grad school is a a trap and a disaster. Only go to grad school. If you reach some arbitrary or literal bar where you cannot keep doing the thing you want to do without a grad degree. So either you don't know enough and you act actually need to study this topic and maybe get a PhD or you're what say I'm like crushing events and I'm at some sort of company or a thing tank and they're like look like this is actually a business line. So like you actually need to get an MBA. If you want to become like the senior VP of like blank. Like that's an example where it's like kind of arbitrary but it's just sort of how the world works. So that's an example of just like that sort of like instinct and applying it. Yeah. What do you think about unpaid internships? So A, they're a societal disaster. This is where those like you would think of an individual scale and a societal scale. My actual solution to this is especially like with like state schools and like private universities at beginning down with this is like they should offer people like aggressive like stipends because it is true that like there are industries where like especially creative industries where like they're actually is like a paid problem. It's like a difficult thing there. So like there are so many things we as a society could do. It's more like just like mandating for example in Congress. One of them paid internships. Congress could just allocate money to get that done. Beyond just because like the the members who pay red this is for DC people. If your member pays for an internship that's them taking from like their own budget because they care that much. They don't have to do that. So like if Congress just sort of said hey here's like a fun to do this. Like that's a very easy thing to do. But on individual level like you kind of sort of have to do it in some industries. But I think what's exciting about like this moment is like you could still do side hustles. You could still like figure things out. So like you want to individual level how to just be creative. And it's unfortunate that like a lot of that creativity is subsidized back. Like on ironically by like your privilege and that just like is an unfair thing of our society. Yeah. I mean I feel like the only people who are not only but the people who I feel like take on unpaid internships are able to are people who have a ton of parental support. It definitely ends up with like a selection bias in those roles. But this is also where it's exciting where like okay so think of think of our work right like we did just start posting one day. So I think what's exciting to the person who can't get an internship ask to choose between like a like like paid like you know job that like you wouldn't try to get if you were out of college. What you can actually do is create a body of work. Yeah. This actually far far more tangible than even the fakest internet. So like this is just genuinely where like because the other part of the crater economy is the like it directs people towards once again towards scale and fame. But what I would think about and what I would have done in college if I were there now is like I always give this advice. I gave a talk of you Tata some students about this for like you know we're talking about intros and emails and like different topics like I would actually just as university undergrad. I would buy a cheap mic and like email 10 professors who like study a topic that I'm interested at or I'd interview with my professors and just use it to like have us like a CV like on a personal website or like on my free sub stack where I'm like hey I'm Marshall here are 10 interviews I did here are three pieces I wrote and that's actually it also like you have more ability to do that on your own time you've ever had. Yeah I don't think everybody can be a creator per se but I think the act of creating online can get you to where do you want to go. Yeah I mean what that requires though is thinking of creation as being less about like you just said views this being your job this being the fame path and more like no this is just about building a transparent way of building legibility with people and by the way if you do those 10 interviews well as the undergrad I actually shock the more undergrads like don't do this no one really does the reading anymore if you just like have some niche you're interested in this could be any niche and can demonstrate someone you actually read the book especially as a young person where they're like seeing these Atlantic pieces about how no one else reads this is becoming even more impressive that person will network for you the person be helpful for you it's just like a real like easy path and you can just do this for free. Yeah an active care yeah showing that you care this a little yeah so yes it is who you know but as Marshall pointed out it's not a list of names really it's a muscle you build a habit across the things you read and listen to the person you go up to with an idea for them an email that is about a project they're working on and not just a copy of your resume and if you don't know anyone it's all about communication and being in the rooms to the extent it's possible as much as possible okay now Marshall is going to apply for a job we're going to do a mock interview so you're going to answer a fake job but with your real resume so you are applying to be the new Gandalf the old Gandalf we had to let him go so we're hiring somebody in a mypu and so our first question is a wizard is never late how much of your career has been timing and how much of it has been luck. Hey just to do the cliche you you make your own luck so you position yourself for luck which then leads into timing because something I have and I wish more people had is part of my like thinking hard about risk is that I care about getting things right and part of thinking hard about a problem is like when does timing actually really matter so like me thinking okay yeah I'm getting seven figures of listenership but this isn't what I need to do actually I could do this other thing and it's not actually a risk or a sacrifice because like the timing isn't right for the thing I want to do and then things just sort of like come so like that's just really really about I'd position myself for like timing and then being comfortable with the in-between space which is where most people are very very weak. Most of the job of Gandalf surprisingly it surprises a lot of people's introduction so making sure that doors and elves and men all get along how do you get people together who don't trust one another. So this is where you have to be really really really interested in people so I work really hard and it's maybe let's hard for me but like you can just work at this at really trying to not even understand someone but like have a good frame on them understand like where they're going what their ambitions are etc etc etc and if you do that across enough people you can just say to yourself like oh I'm at this person and they have this problem and this challenge and I'm at this person and they actually have like this interest so like even if they like aren't aligned or they like disagree on things or don't even like like each other I know how this is the CAA thing I know how to package them together and say like hey meet this person you remember how interested I was in like the two of us when we talked this is an actual person who you're gonna get a lot from who could like help solve your problem but in a neutral way so just like having that field and then like putting together is helpful encouraging them to go on a quest together perhaps yes yeah so our previous Gandalf recruited a hobbit he had no experience it was very senior role everything did work out but you know it was a big big jump so how do you personally plan to spot talent in your role as Gandalf the way I spot talent is like I said at the start of the episode completely ignoring titles and focusing on potential because you could say like okay so yes this person is this now but actually they have a couple like traits or ideas or practices that if you zoom those out three or four years they can really be something and I think just doing that versus the approach of like hey I'm at this intern and like I'm to keep track of them kind of but like we'll see if they actually do their thing so like that's the way I think about it okay I mean that all sounds great yeah you get the job of Gandalf thank you I want this job is what I'm really asking for no that's great so the closer here [BLANK_AUDIO] rapid fire, just a quick luck questionnaire. What's something you were sure would in your career that turned out not to matter? - Losing viewership. - What's the luckiest thing that ever happened to you that you didn't recognize as luck at the time? - Failing, oh, not getting into a top-tier college and then like, flowing at all of my jobs. - Yeah, I think the top-tier college one is that, so I went to Western Kentucky and read it like that's not, it was an excellent school. It provided me a ton of opportunities, but I was so worried graduating that like, it wasn't gonna be a theory decision, but it ended up being the perfect decision. I think we put a little too much pressure on school choice. So final question, what do you need luck with right now? - I need luck with serendipity. So I'm organizing events, and I'm going to events like Aspen Ideas Festival. And I need the right person to walk into the right room that I'm in because the things that I'm working on at a broader project level are things that like are not for like, not even like the mass audience, but like the mass number of philanthropists or like billionaires or foundations, but they're like 15 people, who I think will really get what I'm doing and will go all in, but I've only met those people through serendipity and events. So I need the right person to say, you know what, I'm gonna go to that event. I was thinking kind of tired, I'm gonna go. That's the luck I need. - All right, well, Marshall, best of luck. Thanks so much for joining me. - Thanks for having me. - That's Marshall Kossela. He hosts a realignment, he runs rooms for a living, and if you're a philanthropist, he'd love to meet you. I'm Kyla Scanlon. If this episode was useful to you, let us know. And send it to the person who needs to write an email. And thank you for following the show and leaving comments. I try to read them all, and I'm learning a lot. So I wanna start passing on your valuable advice and experiences, starting with this comment from episode one with Kyrystal. I've been at my job for 42 years. Early on, I immersed myself in learning my work. I didn't know it for 30 to 35 years, but I mean myself invaluable. I know this doesn't apply to all cases, but I believe your work/job is what you make it to be. Luck is what happens when preparation meets opportunity. This show is a production of the Vox Media Podcast Network, made with the help of Megan Kunein, Wendy Mullen, Devon Joseph, Kobe Weiss, and Garrett Williams. Our wonderful theme song is "Fraulic" by Jake Serkci's Fuzzle. You wanna stay on top of your finances, but your tracking stocks in a nap. Trends in a browser and breaking news seem to live only in your push notifications. That's no way to manage your finances, and it's also where Alpha Space by Yahoo Finance can help. Built for sophisticated individual investors, Alpha Space is an investment charting an analysis platform that brings everything together in one fully customizable dashboard, so you can focus on information most relevant to you. Head to Yahoo Finance.com/kala as Yahoo Finance.com/kala. Offer valid for new subscribers in the US. Offer ends December 31st, 2026.

Podcast Summary

Key Points:

  1. Marshall Kosslock builds networks by focusing on people's potential and interests, not titles or hierarchy, which allows him to connect with diverse and valuable individuals.
  2. He developed his network through genuine curiosity, walking up to influential figures, sharing personal interest in their work, and inviting them to meet in informal settings like tacos.
  3. Success in networking comes not from formal titles but from active engagement, showing up with specific project-based questions, and demonstrating genuine interest in someone’s work and mission.
  4. Marshall emphasizes that career growth often involves stepping into the unknown—such as quitting a stable job to pursue a creative or alternative path—while building a safety net through side work and multiple roles.
  5. He rejects traditional career paths like unpaid internships and rigid academic degrees, advocating instead for self-directed learning, creating a personal portfolio, and using online platforms to build visibility and credibility.
  6. A key insight is that risk in career-building is not about taking a leap blindly, but about having a foundation of support and being open to redefining one’s path based on evolving goals and values.
  7. He warns against judging people by metrics like views or clicks, arguing that such metrics reflect only performance, not true potential or value.
  8. The most valuable connections arise from serendipity and shared projects, especially in niche or philanthropic spaces, where few people are aligned with the same long-term vision.

Summary:

Marshall Kosslock shares a deep, practical philosophy for building careers and networks in a shifting economy. He emphasizes that true connection is rooted in genuine interest, not titles or formal hierarchy—he walks up to influential figures, shares personal insights about their work, and invites them to informal meetings. His approach is grounded in authenticity and curiosity, where he focuses on people’s potential and projects, not just their credentials.

He highlights that career success often comes from taking bold, unconventional leaps—like leaving a stable job to pursue a creative path—while maintaining a safety net through side work. Marshall critiques outdated norms such as unpaid internships and rigid academic paths, advocating instead for self-directed learning and creating a personal body of work through interviews, writing, and public engagement. He stresses that risk is not about jumping without preparation, but about having a foundation and being open to redirecting one’s path.

Central to his philosophy is the idea that real value is found in deep, project-based connections, not surface-level exposure. He also cautions against measuring worth by views or clicks, noting that true value lies in meaningful dialogue and shared vision. Ultimately, Marshall’s journey reveals that career building is less about luck and more about preparation, resilience, and the courage to follow one’s instincts—even when they go against tradition.

FAQs

Start by showing genuine interest in people's work and projects, not just their titles. Reach out with specific questions about their ideas or initiatives, which demonstrates engagement and helps build authentic connections.

Yes, knowing people is a skill that develops through practice. It involves being genuinely interested in others’ ideas and being open to connecting with people at any level, regardless of their title or position.

Send thoughtful, personalized emails that reference specific work or projects. Focus on showing interest in their mission or ideas, not just asking for advice, which helps demonstrate initiative and value.

Walk up to them in person, express genuine interest in their work, and leave before it becomes awkward. This approach, as Marshall shares, can lead to invitations like coffee or events, especially if you’re aligned with their values or interests.

Ask about their project and how their work serves a larger goal. This shows deeper understanding and helps open the door to meaningful conversations that go beyond surface-level topics.

Judging people based on metrics like views or clicks. Marshall emphasizes that such metrics don’t reflect true value—some people may not be your person, but that doesn’t mean they’re not valuable or interesting.

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