00:00:00 · Paige Finn Doherty, S1, Molly O'Shea
[00:00:00] S0: What was going through your head as Alex Karp is swinging his order on? [00:00:05] S1: He just starts, you know, [00:00:08] S2: yeah, using his skills. And I'm just... You can [00:00:11] S1: see my eyes. I'm like [00:00:14] S0: How was your first time discovering that Jack and Sam Altman were brothers? Was it? Was it? Oh my God. Was it a Bey? Paige. Hello everyone and welcome back to Seed to Harvest. My next guest is someone very special to me. In just one year of full time building, she's interviewed over 200 plus founders, CEOs, executives, and investors across public companies, startups, VC, growth equity, PE, hedge funds on her show, Sourcery, including Alex Karp, Palmer Luckey, the CEO of Anduril, and Brian Armstrong, CEO of Coinbase. I'm really excited today to be sitting down with the wonderful Molly O'Shea to hear more about her transformation from an NYU art student to VC, to one of tech's top podcasters and the lessons she's learned along the way. Molly, welcome to the show and thank you for joining me today. [00:01:12] S2: Thank you, Paige. And thank you for this amazing setup. This is gorgeous. This is gorgeous. This secret enclave. I don't know where we are. Unclear.
00:01:12 · Molly O'Shea, Paige Finn Doherty
[00:01:12] S2: Thank you, Paige. And thank you for this amazing setup. This is gorgeous. This is gorgeous. This secret enclave. I don't know where we are. Unclear. [00:01:24] S0: So I'm excited to get into it. I actually was I was listening to some of your podcasts. You grew up in Connecticut and I remember you were telling me this or not telling me, but you were telling the interviewer this story about how you would hustle in middle school. Like you were super excited to sell things, make money. Can you talk a little bit about your early entrepreneurial origins and then we'll get into the NYU art story. [00:01:51] S2: Of course. So this brings me back to living at the beach in Westport, Connecticut, and starting a lemonade stand with my sister. [00:01:58] S0: No way, you're lemonade stand? [00:01:59] S2: Of course. Think everyone, did you? No. Then I'm not gonna say that. I think you... I think like, you know, starting off entrepreneurial pursuits, and like being independent as a kid. And like, we grew up in Westport, Connecticut, which is gorgeous. It's right on the water, down by Compo Beach, which is like densely populated. And you could just go to the beach and we're cute, you know, little kids. And we're like wheelbarrowing our like lemonade down to the beach and we're hustling people. We're like, you know what? No, I think we're gonna raise prices $5 a cup. [00:02:37] S0: Yeah, like that. Supply and demand.
00:02:37 · Paige Finn Doherty, Molly O'Shea
[00:02:37] S0: Yeah, like that. Supply and demand. [00:02:39] S2: Yeah, exactly. So kind of a little bit of a taste there, but, you know, I grew up and both my parents were entrepreneurs. They both had their own businesses. So I kind of shadowed them as a kid. I remember driving around with my mom while she's like building and designing homes. I'd be at my dad's office and he had a marketing agency. And so he was working with lots of clients and doing all this stuff. My brothers had worked for him for a little bit. Like my sister and I always were talking about like taking over the business and that kind of thing. So even from a young age, I just like saw what it takes and what it's like building a business. And I didn't see any other reality. Like I didn't know like what being in office I this, whatever it would just like know, okay, like you're the main character, right? Like the world kind of conforms to you and you get to do what you want. Like if nails end up in the middle of the day, they just do. Not to say that I literally don't do that at all. Like I'm really bad with that stuff. I am bad at that. I will go for walks and have calls, but, no, I just like saw from a young age like that. And so I think it was just like ingrained in my DNA, seeing both my parents build their businesses and, you know, do things, make money, do all this stuff, like grow and grow and grow and like provide for our family. That, and so it was the only thing I knew. And I started doing my own little things in middle school. I remember [00:04:06] S0: I would like When did you start painting?
00:04:06 · Paige Finn Doherty, Molly O'Shea
[00:04:06] S0: I would like When did you start painting? [00:04:08] S2: I started art as a young, like a young kid, like I probably, yeah, I probably had always done it. Like my great grandfather was a painter. My, my mom's side of the family, they're all artists. Or at least like practice art. My brother's an artist. He's really talented. My mom's an artist. And then she did the Holmes thing and I naturally had that gift too. And I started, and this was like funny in like my like act two, whatever it might be, will probably be like building homes and designing homes. But ever since I was little, I would like draw houses and like books. And I have like tens, if not like 20 plus of these like little black, you know, those like moleskin books. Yeah. And I like taught myself dimensions. Like, And I, I give myself credit because I think that's pretty fucking cool. Like, taught myself how to build a house with three d and like dimensions and like all this stuff and like make it right. And I would build these like little towns and I'd make like these books full of towns and That's so so cute. It's like really cute because you can go back. Like my mom has a bin. I hope she didn't throw them out, but she has like a bin of like all of my old like books and like drawing books. And so I did that. And then like, you know, down the line I started doing painting and more drawing and like portraits. And I obviously went to college for that, but like it really like started with like drawing houses. [00:05:35] S0: Wow, that's so cool. [00:05:37] S2: I didn't know that.
00:05:37 · Molly O'Shea, Paige Finn Doherty
[00:05:37] S2: I didn't know that. [00:05:37] S0: I knew you wanted to be an architect, like you were considering that. And then you started doing commissions in the homes that your mom was designing. What inspired you to go to college for art? How'd you make that decision?
00:05:51 · Molly O'Shea
[00:05:51] S2: Because it was gonna get me in. Honestly, it's like a fair point, but I mean, like I went to school at a very competitive school. Yeah. All my friends were taking AP courses, like going and, you know, studying with a tutor for fun, like competitive, you know, it was just like that kind of dynamic. I was like, what, like what is going on? Like, you know, I'm a competitive person, but like, I have to like inherently feel like comfortable and competitive in some sort of nature. And like, it just like, wasn't studying. Like I knew I was really good at art. So I just put all my time and attention to that. I was taking like courses at Silvermine art center, which is in like Norwalk. And I would go there after school. And I remember this because like, I would, you know, like in the fall and we're approaching fall and it's going to get dark really early. Like I would go to this place, this like art center after school and stuff, and do many different classes from photography to drawing, like figure drawing, which is like really important for learning the skill of drawing and like sculpture and all this kind of stuff. But once I knew that that was obviously my talent, was like, well, I obviously got to use that to get in school. If you know your asymmetric advantage, you have to pour into that and then use it to get into, because like everybody we're going into college, It's like, Charlotte, who has been helping me, she's 16, 17. She's like applying to go to college right now. And she's like phenomenally well educated. She has so many great extracurriculars, right? And so like, she has like her own path, but like I'm seeing through that process, it's like, you know, like probably the kids at her school, like a lot of these kids are like packing in all these things and it's like, what makes you different? Yeah. And so what made me different was the whole art thing. And then like pursuing like entrepreneurial things, whether it was making commissioned paintings for my mom's clients, doing graphic design on my own. In middle school, I would like, this was like, probably not legal, but like, I would like pick the corners, these like metal corners off of the chorus folders and I'd make little pendants into them. Go to the, like the chain store and I'd buy chains and I'd make necklaces and I'd sell the the necklaces.