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Molly O'Shea
Founder & Host, Sourcery

The Venture Artist w/ Molly O'Shea

📅 Feb 21, 2025 Jason Levin 58 MIN 1231 VIEWS 176 SEGMENTS · 2 SPEAKERS
Molly O'Shea is a venture capitalist and founder of Sourcery, a newsletter about top VC deals and startup trends (02:51) Why every VC has a podcast (07:10) Why podcasting is a good excuse to meet cracked people (13:30) Internet friendship = best friendship (14:40) Molly's artist-to-VC pipeline (18:50) Learning about what VC does for the first time (22:00) Our high school side hustle stories (24:40) Why good artists shouldn't starve (26:09) The VC trash-talking culture (28:27) Fuck Kanye West (31:30) How to get viral by offending people (correctly) (35:10) "Memes aren't gonna save you if your...

Questions asked in this interview

12
  1. 0:10You met Joe Rogan. How'd that go down?
  2. 2:16So do you want the real answer or like which is we are just self-obsessed and love to hear ourselves talk?
  3. 9:14So yeah, if you're listening to this, you don't need to go become the next Mr. Joe Rogan, right?
  4. 13:51I mean, you know, obviously I could talk a lot about that, but just curious, like how'd you make that switch, figuring out venture capital from a studio art degree?
  5. 27:01Like isn't the goal of every musician to sell out a stadium?
  6. 27:46Acquiring a goon tech startup, goonmaps.com, not too far, right?
  7. 32:42I, I know which one does better, funny memes or like offensive memes?
  8. 39:56I share about my failures, like all my sorts of business failures or, you know, even mental health struggles when I was younger, right?
  9. 42:25I think is it causing you to like more things?
  10. 43:27It's, I mean, it's pretty clear like the AI race is taking off. What's AI?
  11. 53:01But who can tell what's going to happen?
  12. 56:55Like, um, can anybody just start a family office?
Molly O'shea 0:00 ↗
Let's pull up the internet from the basement to the high net. Scrolling, tapping, that we ain't done yet.
Interviewer 0:10 ↗
You met Joe Rogan. How'd that go down?
Molly O'shea 0:14 ↗
It was actually a beautiful experience. It was a lot more chill than it might look. It was like me behind a line of people asking to take pictures.
Interviewer 0:28 ↗
Where was this?
Molly O'shea 0:31 ↗
So this was at the inauguration. I was at a couple of the different balls. We went with a group of people, and this was at specifically the Starlight Ball, and it was full of everyone was there, like really, really incredible people. Kind of like a pinch-me moment. I mean, I live in LA, so I'm used to that, but it was wild. The concentration in fancy clothes, everyone is there. And by the way, like you're tired, you're freezing cold, the glamour, the novelty kind of wore off a little bit, but you're like, this is actually insane.
Interviewer 1:06 ↗
Wow, that must be a magical moment. That's very cool. Was there a feeling like 'we're so back'? Was that going on? Did you have any idea what was coming?
Molly O'shea 1:18 ↗
I don't know. One, I'm first upset that I didn't go as viral as that one girl. I didn't see anybody else, I just saw you looking all glamorous with Mr. Joe.
Interviewer 1:29 ↗
Mr. Joe, yeah.
Molly O'shea 1:33 ↗
Yeah, I like Mr. Joe. No, there was definitely a sense of like, holy crap, something's changing, something's about to change and things are going to get real. Part of it felt like a tech conference. I mean, I've been working in VC for like almost seven years now, and so I'm used to lots of these events where GPs come in and different fund managers and different founders and that kind of thing. But having the pure concentration of literally everyone that he's going to be working with and high-profile names, it was really surreal. I was like, I'm the most irrelevant person here.
Interviewer 2:16 ↗
But you look fly as hell with Mr. Joe. Speaking of Mr. Joe, Mr. Joe Rogan, why does every VC have a podcast? Let's break down this question. A lot of people ask this on Twitter and they just don't understand. They think that VCs just are self-obsessed and love to hear themselves talk, but it's like a lot bigger than that. So do you want the real answer or like which is we are just self-obsessed and love to hear ourselves talk?
Molly O'shea 2:46 ↗
That's the real answer, guys. Plot twist.
Interviewer 2:49 ↗
So what's the real answer? Let's break it.
Molly O'shea 2:50 ↗
Kind of, but not really. I mean, every fund has their own marketing strategy, and it's really important for trying to maintain access to deals and access to founders and continuing to build out relevancy. Relevancy is the number one thing for funds. You can ride on the coattails of very large AUM, you could ride on the coattails of your previous successes, but I think marketing strategy and brand differentiation has gotten really serious over the last couple of years. And more specifically, it's really hard to compete with a Founders Fund or an a16z on that front because they're just machines. Like they've nailed it. I don't know who's the CMO of Founders Fund. I don't know, Mike Solana, I think.
Interviewer 3:40 ↗
Anyways, Mike Solana.
Molly O'shea 3:45 ↗
Like they've cracked the code, like they've killed it, like they did really well.
Interviewer 3:49 ↗
They absolutely killed it. Founders Fund is a machine, they're a marketing machine. They've got, you know, everything from John's podcast and his work to Mike's to, you know, even Jesse Michaels, like, you know, he works with tech, like they absolutely killed it. And I think you're right, that was something that super surprised me about VC, which is like, it's not like VCs have to be competitive. And I thought that, you know, coming into VC was like the founders are all competing for the VC's attention. But when there's a hot startup and there's a hot founder, like founders kind of have their pick, right? And it's weird, it's like, oh, don't they just want the money and that's it? It's like, no, you want somebody who shares your vision, shares your beliefs. You want somebody who can quote-unquote add value, right? Like the whole meme of it. But when you are picking a VC, for a lot of these founders out there, like, you know, somebody with a giant audience, giant distribution, somebody who shares that vision, who you know is going to talk about you and share your company, like that's huge, right? And so that is, yeah, I think that's a big reason why every VC has a podcast.
Molly O'shea 4:50 ↗
And maybe yes, the brand differentiation for the funds is one thing, and then to your point a little bit is like you have to somehow provide extra value to the founders, and maybe that's by having them on your show, but I don't, that's like less than probably 1% of the reason because most of these funds do have really, really good PR and comms teams that help those companies if they want, if they're more consumer focused or if they are riding some sort of train to get them that next leg of funding, to the comms and PR route and get really good announcements out, get a good brand halo effect, like build the vision and the strategy around that. But on the actual podcast side, it's kind of one, yes, it is super fun and it's cool, and like there's a weird mix of VC is just such a small niche world, and VCs are like, they have to kind of be a little famous in one way or another, even if it's, you know, just with like nerds, but you have to attract and you have to stay relevant, and like there's all these different creative ways to do it. I know at least for like me and Sourcery, like I started the newsletter like four years ago, over four years ago, and it was just like a little hobby and I liked it, and then I realized like how much value it was providing for my friends. I started sharing it, they started sharing it, it started growing more, and people, I've built like a community around it, like they'll reach out to me, they'll send me companies, they'll do different things, and then next thing I know, like Eric Torenberg, really great guy, Turpentine is an amazing media company, he was building out his suite of podcasts and he asked me to do one, and I was like, actually, yeah, I do want to do that. I've been working on go-to-market strategy with companies in our portfolios, and video is very clearly the next iteration of how you gain people's attention and what's kind of important on the internet. And so I was like, yeah, that's the next form of media I want to try. Do I have time for that? I'm not sure, but for me, I was also obviously, like we talked about this, I'm a huge nerd, I'm a huge dork.
Interviewer 7:13 ↗
Molly is a dork. Don't be worried, she's a dork, very dorky.
Molly O'shea 7:18 ↗
But like for me, I was thinking, oh my God, these are going to be like expert calls that I can share with people I know.
Interviewer 7:24 ↗
Exactly. So that's one of the great things about having a podcast is you could just bring smart people on. And because you're giving them like free content, you're giving them distribution, like people are just so much more likely to say yes than if you go send them an email and say, can I pick your brain? Can I have a virtual coffee? Like that's some dork stuff. Coming on a podcast, having a fun conversation, they get to share their content, they're happy, right? And you know, similar to you, how we've been able to get big guests on both of our podcasts, same with, you know, my newsletter has led to all sorts of weird opportunities. I just started writing it for fun, sharing my thoughts, has led to, you know, deal flow, right? Has led to all sorts of advertisers and businesses that I've been able to start. So, you know, Jack Butcher has a great line which is like, build distribution, then you can build whatever you want. For us, that's investing, startups, whatever we might want to build.
Molly O'shea 8:15 ↗
Always fun to do it.
Interviewer 8:17 ↗
It's always fun.
Molly O'shea 8:20 ↗
It's really fun, and it's fun to like build these like asymmetric, asymmetric is that a... yeah, I think like asymmetric relationships with people that it would not, like you wouldn't normally be able to just do that. Like it's really hard to just ask anybody for coffee, but if you want to have like a meaningful conversation and share it and give distribution and, you know, highlight them, like I just love having people on and like profiling them and like showing all, like I'm just, I'm like a little soft at heart and I'm like, it's so, like I'm so proud of like people and I just, I think it's really great to like share how much progress they've made and how crazy like the different stories are that they've gotten to that point in their career. And like from the technical standpoint and then also on like the entrepreneurial standpoint, like it's really interesting to hear all those stories.
Interviewer 9:14 ↗
Yeah, I think really like what I'm finding the key to podcasting as well is like curiosity, right? And that's why, you know, Joe Rogan, Mr. Joe, he's such a good podcaster is because he's just so curious about things, right? He wants to learn about people, and being curious and passionate is just like a great way to have a conversation. Like, you know, I could talk to anybody, you know, like I'm having you on, we talk VC stuff, I've had friends on, I'm having one of my best friends from high school on in a couple weeks who's a comedian in Brooklyn, and I'm just so proud of him because he's like, you know, we've been best friends or good friends since we were 16, right? And I knew he's going to be a famous comedian. Now we're 27, he's blowing up, right? He's hosting shows in Brooklyn, working with famous people. It's like I'm just proud and I want to talk to you and let's catch up, right? You know, I tweeted this a while back, but like podcasting is like, it's just an excuse to have a conversation with the homies. Like, you know, like it's hard to have deep convos these days, everybody's busy grinding, but if you get to record it, have some fun, like I'm going to have another founder on who, you know, one I invested in, I haven't seen in a few months, and then another who's like one of my good friends from early days. It's like, let's just catch up and have a good conversation too. So yeah, if you're listening to this, you don't need to go become the next Mr. Joe Rogan, right? I've talked about this before. You could just like start a podcast to have conversations with smart people, you know.
Molly O'shea 10:34 ↗
Yeah, there's also a point to which you mentioned, it's like kind of crazy how some of the ideas and thoughts that you have in a podcast is like you don't really talk about with your friends, and you go like a little bit of a layer deeper and stuff, and that brings like an audience and people like, oh wow, like that's really interesting, like I want to learn more. And so it opens up another layer of thought-provoking information, and people are so addicted to podcasts. Like I was telling Mr. Matt over there about this.
Interviewer 11:05 ↗
Mr. Matt, hell yeah, we call him Mr. Matt.
Molly O'shea 11:12 ↗
I was telling Mr. Matt about this the other day, but my dad was like in a meeting and he was talking with someone about like the inauguration, and he was like, oh, my daughter went, and they're like, that's crazy, like how did she go? Like what's going on there? And he was like, oh, you know, she's just a young hustler, like she's a VC, she has a podcast and stuff. And the guy was like, wait, what's her name? And my dad was like, her name is Molly O'Shea. And he was like, no way. And my mom, by the way, my mom's in the other room and she listens on every conversation he has on the phone, and they have really thick Irish accents. I can't do it, I wish I had an Irish accent, but they had really thick Irish accents, and it turns out to be Conor McGregor's media manager team, and one of them listens to Sourcery.
Interviewer 12:05 ↗
That's amazing.
Molly O'shea 12:07 ↗
So shout out to Doug if you're listening.
Interviewer 12:09 ↗
I mean, we were talking about this earlier. You know, Chain Smokers, I was DMing with them earlier and they said they're big fans of my memes and content. I was like, what is going on right now? It's just from putting weird stuff out on the internet. You know, you never know what happens. Speaking of my dad, he's literally calling me right now.
Molly O'shea 12:24 ↗
Nice, nice. He can hear me. I love it.
Interviewer 12:27 ↗
So I think, no, but I want to say one thing about that. I get hung up about this because I'm very competitive, and I'm sure you're competitive too. Like you're building a really good business. Like I appreciate people might not know that, but you're putting down numbers, like you're doing really well. Part of the numbers of doing podcasts and stuff like gets to me, and I want to make those numbers go up. So please subscribe. But you forget because you're constantly thinking about the numbers that those are people listening to you, and you don't know who they are. It could be anyone.
Molly O'shea 13:00 ↗
And it's always surprising too. Like something that I found with creating content online is the people that you expect to support you the most, a lot of times, like your family, your friends, maybe siblings, they actually don't support you, and it's strangers on the internet that you meet that become your biggest customers and fans and supporters. And you know, maybe they hire you or introduce you to people that change your lives, right? Like it's really a very, very sad but bittersweet thing, creating things on the internet, that you find that like people who are just strangers can be more supportive of you than your like high school friends. And I don't know if you've experienced this, but I certainly have, and it was like a very eye-opening moment where it was like, oh, like I have so many friends on the internet. Like I've made so many friends on X and like LinkedIn and whatever over the last... We met on X a couple years ago.
Interviewer 13:51 ↗
Yeah, it's super eye-opening where it's like, and I think a lot of it, a couple things. One is like people who grew up with you are like, they can't be doing this, like, you know, they like put you down all of a sudden. Oh, you have a podcast? That's, oh no, you could just do things. Cringe is the new cool. And then the second thing is like media is so fractionalized that you might have somebody who lives in a completely different part of the world who has the same information diet as you, and that's actually a better predictor of your relationships and friendships than whether you grew up with them. So for example, like some of my team, right, my employees, my meme lords, you know, they're overseas, right, you know, India, Taiwan, but they understand Silicon Valley tech memes better than most of the people in this city, right? Better than most people in America because of the internet, right? And you know, we get along better than me and kids I grew up with in my neighborhood in high school because we have the same information diet, right? And I think a lot of it comes down to that. I want to switch topics a little bit real quick. So I found out this earlier while we were getting smoothies, Molly studied art, so she's a VC dork. She's got that artsy side. I want to, you know, a lot of my readers, listeners in general, they're like artsy creatives who are trying to figure out how to make money on the internet. Do you have any advice for, you know, going from art to business? I mean, you know, obviously I could talk a lot about that, but just curious, like how'd you make that switch, figuring out venture capital from a studio art degree?
Molly O'shea 15:27 ↗
Yes, this is something that I've hidden for many years because it doesn't make for a good way in the door, especially super untraditional. John Coogan put out that tweet, sure it'd be cool now, but like back in the day when there were no women in VC and like it was a much smaller industry, but all of a sudden there's like five billion jobs and people doing it, and it's going to go back down. But so I come from a long line of artists, okay? It's a whole lineage within my family. My great-grandfather was an artist and developed homes, and then my mother was a creative director and she designs homes now. It's like a mix between art, design, and architecture, really fun. Like I thought I was going to become an architect too. I have too many interests, but growing up, like I was always making things and doing projects and like selling things. I was obsessed with money and I would hide it. Like we would, like I'm from Connecticut, so my mom would renovate old houses, like colonial houses, and in those houses there's really like weird unique beams and like exposed things that you wouldn't normally have in like a cookie-cutter house. And so I would always, I would scavenge and I would take money, like I would find it, I don't know how I got it, but I would find money and I would like hide it away. So I was like obsessed with money, and then I was like obsessed with making money, and I've always wanted to like make money and like do things on my own. And so in middle school I started like making things and selling them. It's just a process of making things and selling them. That's like all it is. That's all I do. That's all it is. And then like in high school, like I kept on doing that too. I'd do little projects here and there. Like I would like infuse my art stuff with that, and with my mom, I would do like custom paintings for her clients, and I would rake it in. Like as a high school student, I was making a good amount of money. And I used that to get into college. I had an art portfolio. Like I was deciding, oh, maybe I'll do the architecture route. I spent one summer at USC in LA doing their summer architecture program, and I would say I finished top of the class, extremely talented, but we spent nine hours of the day in the basement, and like I couldn't foresee myself like nine hours a day in a basement while everyone's like marching around at USC and like having lots of fun, like going to games. And then I also learned, I sniffed this out very early, like in any area that I'm going after, architects don't make that much money.
Interviewer 18:14 ↗
No, they don't.
Molly O'shea 18:15 ↗
It's a lot of effort for minimal output, and so like the energy towards like incentive, like it just wasn't computing for me. I didn't get it. I love it, I appreciate it, I think that's great, maybe I can do it later on in life, but like I was like, this is not how I'm going to make money. And so long story short, I went to college for studio art. I got in with an art portfolio. I won a couple of awards in high school. Like I'm pretty talented, I'm not going to lie. Like I can flex on that. Like back in the day, I was a prodigy for sure.
Interviewer 18:56 ↗
No way.
Molly O'shea 18:57 ↗
But I get in there and I went to NYU. I really loved NYU and I wanted to go there because during orientation they were talking about how like theater students, you know, they pivoted and they went into finance and they're on Wall Street, and then like the Wall Street people pivoted and like they're in marketing, like they're doing like all these different things and people are trying things. Now it's a little bit of a joke because like Gallatin, like you can make up your own thing and it's very socialist, but that's fine. And so I went there and I was like, this is great, like I can do some entrepreneurial business stuff while I'm studying art. Turns out I have very low patience and high ADHD, so like I need to be doing lots of stuff at once. I learned very often, like one of the professors was like, yeah, like the common salary when you graduate is like twenty thousand dollars. I'm like, twenty-two thousand dollars? Are you kidding me? I live in New York, like my student housing is like thirty thousand dollars. What do you mean? Like how is that a... what do you do? Like that doesn't make any sense. So I started working at startups, I started my own company, I then like worked at Google's incubator called 30 Weeks here in New York. I was like working freelance and doing graphic design for people. I was just like hustling my butt off, like working like so many jobs at once. And it wasn't until I worked at 30 Weeks, Google's incubator, that I got exposed to venture capital because there was a venture capitalist on the team and he was, you know, he was looking at all the companies and he was making decisions on like which ones to take a bet on and which ones could, you know, do well and make money. And I was like, oh, I want that job. Like that's cool. That's cool. I can learn how businesses work and like make money doing it. Like that's awesome. I don't know what I'm doing building a company right now, but it seems like a low-risk, high-reward thing.
Interviewer 20:56 ↗
And you get like a really good mix.
Molly O'shea 21:00 ↗
And I just like tunnel vision was like, that's, I'm doing that, so I'm going to go do that. And I ended up like cruising through NYU, I graduated early, and then I went down to a family office, I started working at a family office, got exposure to all the different things that I wanted to work on, whether it was like real estate, starting a company, or working in VC. And I just like, gravity was pulling me over to VC because it was like heavily research-oriented, but like also, you know, you're meeting people, it's social, it's like a lot of different things at once, and it just like really fit my personality and I just really liked it.
Interviewer 21:39 ↗
Oh, I love it. That's so cool. Not as untraditional as Daniel Penny and his path to venture capital from the Marines, choking out a dude in the subway to being a 16z partner, but close second, right? No, I love it. So I, you know, started out, I studied English and have always been a creative kid. I was selling stickers in high school that I designed on Photoshop, made like forty grand selling stickers.
Molly O'shea 22:11 ↗
Yeah, in middle school I was like making duct tape wallets and selling them.
Interviewer 22:15 ↗
Of course you were. So did I. I was making t-shirts and selling those. I was buying watches from Alibaba and like selling them and flipping them. So like I've always just loved making things and selling them. And there's a certain point where you love your art and you are trying to figure out like, hey, how do I make money? And it's like this in-between point, right? It's like so scary and it's like, you know, I don't know. I think we both did a good job with this, combining the two where you get to like be artsy but also make money. Like Sourcery, right? Like I've always thought you've had like a good design flair with it, and now it makes sense knowing your artistic background. It's like, oh, that's how you had like the cool colors and the design. Like I've always thought that, really good. So it's cool you can incorporate your art and still make money, right? Like you could do both. You know, now like I get to build software, right? Memore Technologies is, you know, this cool Windows 95 retro design. I'm literally using the same skills when I was fifteen on Photoshop to like go make stuff, right? Like if you look at my Facebook profile pictures from when I was ten, it's literally like my head cut out and like literally memes that I'm making now. Like I'm the same person, just have an audience, can make money with it. Like that's literally it. So if you're making art on the internet, just be patient. Figure out a way to make money with it, but it takes a while. And you can incorporate it in different ways. You're not a sellout just because you go do business. You can incorporate art in that. Andy Warhol has a great quote which is like, you know, good business is the best art, right? I talk about this a lot. It's like negotiating a deal, it's like screenwriting, right? When you think about it, like sending those emails, like you're hopping on the phone, like it's drama, right? Like writing an advertisement, like that's poetry, you know? Like my aunt, she's a well-respected poet and won some awards for some books, but she's broke as fuck, right? You know, absolutely broke and like very, very pompous kind of broke. Well-respected poet. It's like, I'd rather write tweets, write bangers that make, you know, a lot of money. Like, you know, I'm not going to go that path, but you can make money and still be artsy, you know.
Molly O'shea 24:26 ↗
I guess that's my... The problem is though, because I did go to art school, I mean I finished up pretty much all my credits as fast as possible because I just wanted to take as many business courses as I could. But the problem with like the whole culture of art is you're not allowed to make money.
Interviewer 24:45 ↗
No, you're a sellout.
Molly O'shea 24:47 ↗
You're supposed to suffer and then your art will be good once you're dead.
Interviewer 24:52 ↗
It's so sad. It's just such a bad path. And anybody who wants to make money is a horrible person. And like, you know, Jeff Koons was like someone you didn't look up to.
Molly O'shea 25:07 ↗
I'm like, are you kidding me? Like he's a genius.
Interviewer 25:10 ↗
I know. Warhol, minimal effort, maximum output. This is amazing.
Molly O'shea 25:13 ↗
Yes, and like it works, and he's just cooking, and he's doing a great job. And who's to say that's not success? Like I think when you bring up definitions of success, it's all really interesting and relative. And I do think like value is a social construct, but like when you go across different categories too, like even when you go into VC, what is successful for VC? Is it like raising a fifty billion dollar fund over time, or is it having like the most exits? Like what is it? And it's like hard to say because you would also say like, oh, maybe the person who can raise really large AUM is super successful because they're really good at selling, they're good at selling LPs, they're good at building a story and like a firm and like that kind of thing. But then other people would say like, no, it's the person with like the most amount of exits. So it's like, it's a weird thing. And I would say like the one thing that I really don't like about VC is when I mix in with my friends and like we talk, it's like if you bring up anyone, the immediate reaction is, oh, they're not that good, like oh, they're bad, or like you're just automatically like the initial reaction is like to put people down. It's wild in VC.
Interviewer 26:29 ↗
Yeah, for sure. People just don't, they just talk trash about everyone.
Molly O'shea 26:33 ↗
Yeah, it's not healthy. But I don't think that's a secret either. Like people are always just like, you know, it's a very singular player game or single player game, I don't know what the gaming term is. And so it's super competitive and people are always like looking out for each other. But yeah, it's like a weird cultural kind of situation. And I guess like going back to art, it's okay to make money.
Interviewer 27:01 ↗
Yeah, it's okay to make money. You know, selling out, right? Like isn't the goal of every musician to sell out a stadium?
Molly O'shea 27:10 ↗
I would think so, yeah.
Interviewer 27:12 ↗
Yeah, that's the goal, right? It's okay to make money, you know. But when do you push it too far?
Molly O'shea 27:16 ↗
When do you push it too far? I think you push it too far when you do something that's completely against your morals, when you break maybe some laws potentially.
Interviewer 27:28 ↗
Depending on the law, because some... put up a website with one singular...
Molly O'shea 27:33 ↗
No, not that one.
Interviewer 27:34 ↗
Well, that one is definitely... Oh, we're talking Kanye.
Molly O'shea 27:38 ↗
Yes, we're talking Kanye. Kanye pushed it too far.
Interviewer 27:40 ↗
Too far, way too far. He's gone, he's done. He can't come back from that. It's over.
Molly O'shea 27:45 ↗
Yeah, one hundred percent.
Interviewer 27:46 ↗
Acquiring a goon tech startup, goonmaps.com, not too far, right?
Molly O'shea 27:53 ↗
I don't know about that.
Interviewer 27:55 ↗
I don't know, I didn't get canceled. I had my best month ever. I'm chilling. I get like vice categories is one, you know, it's a very good business.
Molly O'shea 28:03 ↗
It's a very good business. Like vice categories in general, like things that sell are like porn and money and gambling and like that kind of thing. To each their own.
Interviewer 28:15 ↗
Okay, like hey, you know, it's a Men's Health data play actually.
Molly O'shea 28:18 ↗
Okay. Do you invest in biotech by the way?
Interviewer 28:21 ↗
I don't want to talk about this.
Molly O'shea 28:23 ↗
All right, we don't have to talk about this. Anyways, back to the important things of Kanye and swastikas.
Interviewer 28:28 ↗
It's kind of sad because like I grew up super hard on Kanye. You know, every Jewish teenage boy, like Kanye was our dude. Like we were nerdy Jewish kids and we just wanted to feel cool, so we listened to Graduation, you know. And when we got our heartbroken, we listened to My Beautiful Dark Twisted Fantasy, right?
Molly O'shea 28:48 ↗
Yes.
Interviewer 28:49 ↗
And like, ah man, it's just sad. It's really sad. You know, our boy Jared, biggest Kanye stan, you know, biggest. And now it's just like, bro, fuck that guy.
Molly O'shea 28:59 ↗
Sad.
Interviewer 29:00 ↗
No, I'm sorry, you can't come back from that. Like it's not cute, it's not funny. It's not even like a troll play. Like no, it's just too far. It's pure hatred and anti-Semitism.
Molly O'shea 29:10 ↗
No, it absolutely is. I don't think there's like any place in society for any jokes on that, even if it was a stunt. Like it's, you just, he has kids and like he has all this stuff. And thinking about that last night, I was just like, I feel so bad for them. I hope they're like okay. Like they're probably getting made fun of and shit.
Interviewer 29:29 ↗
I mean, you would hope that they're shielded from that, but can you really be shielded from that when you're...
Molly O'shea 29:35 ↗
No, you can't. But like I don't know what their social circumstances are because like their family is shielded, whatever. I hope, you know, prayers for Kanye, whatever. Like let's hope.
Interviewer 29:47 ↗
I don't know actually. You know what, fuck Kanye.
Molly O'shea 29:50 ↗
I hope... I don't know why I was saying that. I was saying that before because like I...
Interviewer 29:52 ↗
I was saying that before because like I...
Thought he was just like going through a manic breakdown a couple years ago. I was like, oh, you know, guy needs his meds, whatever. But now at this point, it's, it's, I hope he ends up in jail or, you know, whatever. No, like there are like real repercussions for that. Um, I, I don't think you can play to the cutesy like creative aspect to it. I, I don't think you can play to like, oh, I'm a creative, I do crazy things, like I need to fuel my creativity and blah blah blah blah. I think he just generally like, from my, from my psychoanalysis of the situation, I feel like with the Bianca stunt on the red carpet and he went viral for that, like, you know, when you go viral it sends off lots of endorphins, you feel the rush, like it's a real thing, you're glued to it, you're feeling like you're top of the world, and next thing you know, like, okay, what, what other buttons can I press, like how far can I push things. Like I think he, he's a little goon because he gets attention for it and he, he fuels off the attention, but I think you just, you can't, you can't come back from that one because it's not funny.
Molly O'shea 30:59 ↗
So let's, let's talk, uh, we wanted to talk about this earlier. We were talking, um, about pushing it too far, right? And so Kanye obviously pushed it too far, and that's something, you know, I work with 30 plus brands right around meme marketing. A lot of it is unhinged viral, and that's one of the first things we talk about is who can you not offend, right? And it's actually like a very like, you know, interesting question to ask. So like some, some customers of mine and some clients, right, they can't offend founders, right, but they could offend VCs, so they could go make fun of VCs, but you can't offend founders, right. Other ones you can offend engineers, you know, but you could go, uh, you, you can make fun of product managers, right. And so like that's something that we talk about all the time with, with founders that I work with is like who do we have to be really careful to offend, right? Um, so that's, that's something.
Interviewer 31:51 ↗
Do you think... okay, so maybe I want to break that down. Like, what is the formula for a viral meme? What is the formula for a, a little bit of offensiveness?
Molly O'shea 31:59 ↗
Yeah, a little bit of offensiveness, but not to the point of like, uh, racism. Uh, even like I'd be careful around like sexism generally. Like, uh, unless it's like a girl can be a lot more sexist I think than say a guy or a company. Um, I don't know if that's true, but it feels like it's true. And, um, I think yeah, I think a little offensive is good, but like, or, or even pretty offensive, but okay. I, I don't know, like the formula for a viral meme is, is it funny? Uh, does it kind of, does it piss off the right people and make the, make the right people laugh, if that makes sense? Like you want to offend some people, but you also want to make them laugh at the same time.
Interviewer 32:42 ↗
I, I know which one does better, funny memes or like offensive memes?
Molly O'shea 32:46 ↗
Both. So like memes are like hidden truths, you know, like it is a straight up hidden truth in this funny viral image, and yes it offends like one group, right? You focus on some problem or some silly issue that they have and you're able to like sort of offend them, but it's, it's not deep enough where they like hate you for it, right? That's, I think that's the line, is like it offends you, but like you don't hate them and like want to like ruin their lives, right? Like, uh, you know, Kanye, like no, he should be in jail, but like somebody else making a funny Jewish joke, like I wouldn't think that, right? You know, or somebody makes a joke about marketers, like I, I think it's funny, right? But if they say like marketers are all scammers and terrible people, it's like no, like I'm blocked, right? You know, so like can you push the line without going too far, I think is the thing, right? So yesterday I have a post doing really well right now about like making fun of French founders, right? And my, you know, my wife was like, uh, very, uh, she's like, oh, you're, you're going to get in trouble for that. And then I posted it and like a couple French friends actually just commented and said that's hilarious, like because I didn't go too far, you know, and they know I'm joking. So there's a fine line that you have to figure out where it's like can you offend them without, uh, you know, ruining, ruining their day, like without making it so deep and like attack personal, like can you offend them, uh, in the right way? And it's a very careful thing.

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APA

O'Shea, M. (2025, February 21). The Venture Artist w/ Molly O'Shea [Interview transcript]. Jason Levin. CEOInterviews.AI. https://ceointerviews.ai/interview/3045938/

MLA

Molly O'Shea. "The Venture Artist w/ Molly O'Shea." Jason Levin, 21 Feb. 2025. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3045938/.

BibTeX
@misc{oshea2025_3045938,
  author       = {Molly O'Shea},
  title        = {The Venture Artist w/ Molly O'Shea},
  howpublished = {Interview transcript, Jason Levin. CEOInterviews.AI},
  year         = {2025},
  month        = {feb},
  url          = {https://ceointerviews.ai/interview/3045938/},
  note         = {Speaker-attributed transcript with timestamps}
}