Today I am speaking with Jesse Draper. Jesse is a mother of 2 boys, founding partner of Halogen Ventures as well as creator and host of Emmy nominated television series, The Valley Girl Show. Draper is a 4th generation venture capitalist focused on early-stage investing in female-founded consumer technology. Among her 55 portfolio companies, are the Skimm, Carbon38, HopSkipDrive, The Flex Company, Eloquii (recently sold to Walmart) and This is L which recently sold to P&G. She stars on SET's television series Meet the Draper's currently in it's second season.
This podcast series is hosted by Patricia Kathleen and Wilde Agency Media. This series is a platform for women, female-identified, & non-binary individuals to share their professional stories and personal narrative as it relates to their story. This podcast is designed to hold a space for all individuals to learn from their counterparts regardless of age, status, or industry.
TRANSCRIPTION
*Please note, this is an automated transcription please excuse any typos or errors
[00:00:00] In this episode, I had the fortunate opportunity to speak with Jesse Draper. Jesse is the founder of Holligan Ventures and the creator and host of Emmy nominated The Valley Girl Show. Key Points addressed where Jesse's founding of Holligan Ventures and its work as a Los Angeles based venture capital fund focused on investing in early stage consumer technology startups with a female in the founding team. We also unpacked Jesse's extensive knowledge of creating and hosting what was the first tech talk show, the Valley Girl Show, and what the industry was like a decade ago during the show's inception and growth. Stay tuned for my informative talk with Jesse Draper.
[00:00:43] Hi, my name is Patricia Kathleen, and this podcast series contains interviews I conduct with women. Female identified and non binary individuals regarding their professional stories and personal narrative. This podcast is designed to hold a space for all individuals to learn from their counterparts regardless of age status for industry. We aim to contribute to the evolving global dialog surrounding underrepresented figures in all industries across the USA and abroad. If you're enjoying this podcast, be sure to check out our subsequent series that dove deep into specific areas such as Vegan life, fasting and roundtable topics. They can be found via our Web site. Patricia Kathleen .COM, where you can also join our newsletter. You can also subscribe to all of our series on iTunes, Spotify, Stitcher, Pod Bean and YouTube. Thanks for listening. Now let's start the conversation.
[00:01:40] Hi, everyone, and welcome back. I'm your host, Patricia. And today, I am so excited to be sitting down with Jesse Draper.
[00:01:46] She's the founder of Halogen Ventures and the host and creator of Emmy nominated The Valley Girl Show. You can find out more about all of the endeavors that we talk about today and her on Hellgren v.C dot com. Welcome, Jesse.
[00:02:01] Thank you. I'm so excited to be here. I love what you're doing.
[00:02:05] Absolutely. I love what you're doing. So the feeling is mutual for everyone listening. We're going to climb into a quick bio of Jesse. But before we get to that, in case you're new to our series, a quick roadmap for today's podcast, we'll follow the same trajectory as all of them in the series. First, we'll look at and packing Jesse's academic and professional background leading to the launch of Helen Ventures. Any pertinent information that we can garner from that? Then we'll go jump straight into unpacking HelpAge and Ventures. And for everyone listening, all of our nerdy little founders, not crew, is out there. We'll start out the logistics, the who, what, when, where, why funding all of that, the logistical stuff up front. We'll get into the ethos of what they're doing with halogen and how all of it's working. The impetus. Some of the markets that they've service and the populations that they kind of look at working with. And then we'll also unpack the Valley Girls show it is Emmy nominated. It's it's got a really cool impetus. Jesse spoke with a bunch of really fantastic people over the past decade. And I have a lot of production questions for those of you who are looking at it, the medium of kind of mixing in YouTube with everything that everyone's doing has been a very real part of the integration model and as as you could, particularly entrepreneurship and followership. But we'll kind of look at all of that and then we'll unpack other media like endeavors that she and her prolific family that she comes from have done. Then we'll turn our attention towards looking at goals and plans that Jesse has for the next one to three years. This has changed for everyone, entrepreneurs and successful titans alike. Given the recent Koban 19 pandemic and how some of that has changed and what her conversation with her company and herself has been like in reassessing those goals for future plans, we'll wrap everything up with advice that Jessie has. For those of you who are looking to get involved with her, what she does, or perhaps emulate some of her careers. Magical success, as promised. A quick bio on Jessie before I begin peppering her with questions. Jessie Draper is a mother of two boys, founding partner of Logan Ventures, as well as a creator and host of the Emmy nominated television series The Valley Girl Show. Draper is a fourth generation venture capitalist focused on early stage investing in female founded consumer technology. Among her fifty five portfolio companies are the skim carbon 38 Hop, Skip, Drive, the Flex Company and Eloqua recently sold to Wal-Mart. And this is Elle, which recently sold to PMG. She stars on Essie's television series Meet the Draper is currently in its second season. It says here it might be in its third or fourth. We were just talking. We'll get Jesse to clarify that later on.
[00:04:43] Draper was listed by Marie Claire magazine as one of the 50 most connected women in America. Draper has been a contributor to Marie-Claire Matchable Forbes and is a regular investor and tech personality on shows including TLC, Girls Starter, The Katie Couric Show. Fox is Good Day, L.A.. CNBC sees Who Wants to be the Next Millionaire. Invest in Ventor and Freedoms Startup U.
[00:05:10] She proudly sits on the Board of Directors of Enterprise Technology Company Work Blue Fever PREE Madonna, creator of Nale Bought and the nonprofit board biz world. Draper supports the Parkinson's Institute and is very involved with growing UCLA as female entrepreneurship community. Now, Jesse, I know if I am if I stumbled over any of that, you can absolutely clarify. But before we get into unpacking halogen and everything that you're doing there, I'm hoping you can draw us a roadmap for everyone listening or watching the vodcast today of your early academic and professional life that led you to launching Holligan.
[00:05:49] Yeah, I. Hello, everyone. I'm happy to be here. And, you know, I think like most career trajectories, it's it's not you know, it's not a straight line by any means. But it does make sense for you here. Sort of like you have moved me. But I grew up in Silicon Valley, as you mentioned. I'm a fourth generation investor and the first female in line. I didn't think I could go into that profession, although I had many venture capitalists in my blood. And that was sort of all I knew growing up in Silicon Valley. I grew up around incredible entrepreneurs. It was, you know, a very privileged human being. And I. But again, I didn't think I could go into this profession because my mom worked incredibly hard raising four children. And my dad was very he really opens the curtains to me in terms of educating me about startups. I worked with him a little ice or steels for him through my show, like Paperless Post and numerous others. And I I worked at an asset management company just after college, but I just didn't think that I could go directly into that career because I didn't see any women around me. And so I saw my Aunt Polly and they say, you can be what you can see. And my aunt was this very successful actress. And, you know, it's sort of funny, but I thought, oh, as an eight year old child, like, that's what a traditional job for a woman, you know, because she's something and I'm very close to and that's what she does. And she was on the show called 30 Something in the 80s that was really popular. It's coming back on Netflix, actually. Shameless plug. And she I just idolized her. So I went into entertainment and I, I went to UCLA. I studied theater, film and television. And I my dad was always kind of in the back of my head saying, Harvey can make this a business. How is this a career? You know, he was supportive, but he was sort of like, you need to figure out how to make a living doing this. And it's a very difficult lifestyle. If, you know, she's like, it's rare that Polly had such a successful career and still has. And so I went to UCLA after UCLA was on and a glowing show was acting, was going to cattle calls. And I very quickly was like, OK, I love and respect to this profession, but I go to these cattle calls and there's a thousand girls who look just like me and are probably much more talented. And my heart is really good with this world of technology. And so I kind of combined my two passions and I basically said, OK, I have a third season of this Nickelodeon show and then I have a six month hiatus. And instead of auditioning this year, I'm going to go start a technology talk show. I've never seen one. I always thought these people should be idolized. And I say it's the first technology talk show. You know, people can kind of come at me and prove to me that there was one before. But I had the former CEO, Eric Schmidt, in two thousand eight on my show and no one cared. So I bet it was like one of the first in these like early, early days after two seasons of the show online. And, you know, you were alluding to asking about distribution, et cetera. You know, this was my own entrepreneurial print, unreal journey. It was like early days of digital distribution. No one knew what they were doing. It was a complete disaster to get your content out there. And I was looking for eyeballs, but because I was on a no gloating show on Nickelodeon, was owned by Viacom. And I anytime and Viacom was in a lawsuit with YouTube. And so anytime I put something up on YouTube, it would be taken down because my identity was owned at that time by Nickelodeon, essentially like my IP. It was this weird thing that everyone was still figuring out. So I didn't really focus on YouTube, but I was like, where else can I find eyeballs? And so I ended up working with Forbes, Mashable, numerous others, and we created content. I was one of the first shows to do a deal with all those airports and hotels. Now it's much more normal, but we were getting millions and millions of users through those. And I was just it was this really discombobulated situation. After two seasons of the show, we then took it to television, were ultimately nominated for an Emmy, but also after two seasons of the show. So we did a total of. Seasons, sorry, I feel like I'm all over the place today. The world is in shambles. That's right. I'm sure it would be bad not to even address that. These are horrible. I mean, these wonderful protests are going on. But just like there's so much horror in the world right now in the last word of all these problems. So so basically, I sat through the show after two seasons of interviewing incredible men in technology. I was like, this is still the problem. There's a huge problem here. Like, I just didn't viewed men in technology for two seasons. I didn't think I could go into technology because I didn't see any women. And I need to change this. So I made an initiative to interview 50 percent women in technology on the show. And this was like. Long enough ago that it was impossible to get the Meg Whitman's of the world. It is so difficult because they did not want to put themselves out there. This was like a generation of women who were like, I'm not going to help you. I had to fight so hard to get to where I am. And I was dying for mentors. I was dying for advisers. And I just got shot down and shot down again. And I'm forever grateful to the women of fashion technology because once that started booming a little bit, it was Jen Hyman from Rent the Runway. She came on my show. That made it OK for Rebecca Minkoff to come on my show. That made it okay for the guilt girls to come on my show. And that made it OK for Sheryl Sandberg to come on my show before she'd written Lean In, before she had really gotten out there. She was a new CEO at Facebook and that changed my life. I got all of a sudden it was like celebrities and Jessica Alba and the CTO of the United States of America and like really put me on the map. And it was a fun, silly talk show. Very different than most technology talk shows. But I started doing this like Rock in Women series. And I look back to that first Rock and Women series. It was so cool. It was Sheryl Sandberg. It was this woman, Beth Cross, who started area. If anyone is a horseback rider, that's like the biggest horseback riding brand. It was really a heart. So I'm still pretty close with from Eventbrite, which has now gone public, like looking at these women, just like me chills. And that was the beginning of this journey that I was just striving for more for women. I grew up again in this family of investors, and I knew what a good deal looks like. And I was sending my dad all these deals because they pitched the show as a technology company. And I'd say you're too early for the show, but maybe you should go talk to some investors. I know. And then I was like, I can do this. I don't have any money, but I can do this. And so I, I started seeing some deals. I'd say you're a little early for the show. Love what you're doing. Can I write you a Penneys check? A thousand dollars, a thousand dollars, whatever I could afford at the time. Sometimes I would negotiate sweat equity and get some advisory shares and, you know, help them with PR and media exposure. And I created this nice little track record. I'm one of those companies I sold for a twenty five X return in less than 18 months on the secondary market. And that was like just a huge moment for me where I realized. The show was going OK. I was barely breaking even. Media is still pretty broken, although everyone's eyes are on online. So this is it's booming right now. But I was like, there's something wrong. I've never been on television. I've been online. No one knows how to make this a really profitable business unless you're selling tons of swag. And we were too, you know, early to, like, have that brand recognition. And so we. So I just sort of put the show on pause. I had to be I got married, had a baby simultaneously while raising my first fund. So I used the track record from those little angel investments I'd made to raise fund one. I pitched five hundred investors, closed, maybe 50 of them. And the first people I went to were these people I had created relationships with through my talk show. And so Alexis, moving from Gilt Group was one of my first investors, you know, and I got this nice group of people who had watched and gotten to know me through my sort of media channel. And that was how I began to build my network in terms of raising capital. We're now on our second fund and we've invested in 62 companies, all female founded. There has to be a female on the founding team of five. We've had about six exits to date. Two were one hundred for one hundred million dollars. And that's still pretty early in terms of our trajectory. And I just want to keep thinking about investing in women as an opportunity. A lot of women are going out and saying, oh, poor me, I'm a woman. Invest in me. This is an opportunity. This is not a charity case. Investing in women is not charity. You are going to make a lot of money. Women raise half as much capital. They double the return. And and so that's where proving that out day by day. I'm also really proud of the fact that because I went off of I live in L.A., we I went off of the traditional Silicon Valley Road, which I literally grew up on and totally love and respect. But again, there was no gender diversity whatsoever. And I'm I put out this. We are investing in women. And it was like this bat signal. This magnet for thousands of female deals because women are looking for women investors is they're starting companies that often men don't relate to. And you need we need men. There's not a man hating club we need, especially because they control the majority. But we really need people to invest in more women. And so I started thinking about, oh, wow, we're getting all these women from all over and we're investing in the best deals and completely just that was our beginning strategy. And we have over 60 percent minority led companies because we were looking for the best. And I'm so proud of that, especially today, because it is so important to we always say, you know, invest in diversity. We invest in diversity of gender, race and age. And I think that diversity breeds success. And it's really important to give everybody a shot. We are we're very easy to get a hold of. You can hit me up through the website. You can, you know, purchase through the website. You can find me on Instagram. I'm taking pitches through Instagram at Jessee. See Draper dot com. Jessica Draper from all over the place today. Goodness, Patricia. But I'm I at. But we take pitches everywhere because I never want people to feel like you have to have an introduction to me. I think it's really important that everyone has a shot and we might miss out on the next, you know, Uber or something even better if we don't look at every deal we possibly can. And so anyway, that is my that's how I got here.
[00:18:24] Now you're here.
[00:18:26] I well, I think it's interesting when you talk about the culture of, you know, you can see we can get into the statistics that everyone's heard a million times over about the consumer dollars and the power that women and women identified non binary.
[00:18:38] Those communities have in what they're spending and how they're not taking advantage over that power and things like that. But you and I were talking off the record before we started filming about this kind of I was kind of baptized into the concept a little bit too late for my comfort. But this concept of the lifecycle of the female entrepreneur and founder and how the matriculation should naturally turn into when I say female, I mean female identified non-binding as well. Pretty much anyone other than the white man. It's kind of been represented and spoken about as 50 years. Not that I don't care about them, I just don't. Not speaking to them right now. The responsibility that they have in the life cycle about eventually matriculating all the way through and becoming investors themselves and becoming, you know, part of this like giving back into that system where they invest in. Melinda Gates has talked recently on a very open platform. Is this being one of her major issues and concerns as of late? And I think that it's so important to kind of unpack that. And one of the most interesting things, we have all these correlations and nothing is causation and a member never claiming that. But there are these correlate of values. When you say, you know, we were just looking for the best and we wanted it to be female or some kind of woman involved in the original founding of it and to have it all of this and also be represented and, you know, minority representations in populations as well as just it's proof, as you're saying, diversification works and it drives. And, you know, there's a lot of different. I come from a huge psychology and sociology background. So a large part of me wants to pass out like who? It's because those people fought harder. It's because they were more used to hearing those because they had to do that. And then if that is neither here nor there and it's again, it's all correlation. But I do think that there is truth in that and people can talk about it all day long. But until you put your effort and your money down as you have, the change is not yet happening. And I think that there's been a lot of discourse in the communities that I have spoken with in women investors and ventures and things of that nature where there's still a lot of chat. There was a lot of hyper conversation about the Metoo movement, you know, and how people were terrified that it was just going to go away, it was going to get all this publication, were going to take down a whole bunch of horrible abusers. And then it was just going to kind of go back to business as usual.
[00:20:49] There wasn't gonna be any law, there wasn't gonna be any change and things like that. And I think the same thing is true with investment.
[00:20:55] And I'm looking at changing the seat at the table, as Gates said, you know, putting the change out there is your your fund has been and talking about it, I think is a crucial part of the process because we can all have these summits and discuss things as women and female identified individuals. But until we start putting those things into motion, it won't change for our children's generation. And that's my goal. You know, mine is is happening right now and playing out well. But my daughters need to come up in a different world where they see people looking like us and female identified individuals at the table, because when I was coming up, I didn't see nary one female in tech until Oriana with Huff Post, like I did not I did not know of one.
[00:21:37] And I hung out with nerds from Atari days up like I was kicking it with with the kids that were playing it, then programing the games, then in their parents garage. And it was always meant and, you know, it was usually always white men. And so even from the visual aspect of the archetype that I saw in person and on TV, you were saying your daughters are clearly going to be fine.
[00:21:59] I'm glad you're even thinking about that. I mean, one of my biggest frustrations, running a fund that focuses on women is that. Fund one. I went out and thought, oh, I'm going to go meet with the female billionaires and all the women investors I can find. And, you know, I'm not saying I sat down with every female billionaire, but quite a few. And what I found is women are more comfortable writing a multimillion dollar check to charity than investing in a fund. And I started asking why. Why are you bragging to me about how you wrote a three million dollar check to that charity you believe in? And why have I had six meetings with you and it's taking you so long to get across the table here. And, you know, they say, well, I don't know that much about venture capital. I prefer if you talk to my husband and it's like meeting six, I now have this rule that after three meetings, you know, you know, if they're in, you know. And I'm like, OK, well, let's meet with your husband, you know, and usually the husband's game. And it's it's fascinating to me. But we started a dinner series. Now you'll have to come to one. And now it's very easy because they're all in to where I was really frustrated that women are not taking enough risk with their capital. And so, anyway, fund, you know, my investors overall are the majority are male. It's probably 60 percent male to female. And that's what's frustrating for me. I, I would love to have, you know, much larger female investor base because of what we're doing. But again, I do love men. I was raised by incredible men. I just got and men control the majority of the capital that we needed changing at those levels. We need it. I walked into a workers comp fund somewhere in the middle of the country and I was like laughed at, like the coffee came out of this guy's mouth. And he's like, I can't believe that you're investing in women. And why would we invest in this fund? You only invest in women. And I was like, OK, well, I guess, OK, I just went back and. So here's why it's a great investment. They raise half as much capital. They double the return. Here's all the data. And I was so grateful because about halfway through that meeting, one of the associates came in and it was a younger guy. And he said, oh, my wife uses that company. And, oh, yeah, I've heard of that one, too. And so I do see it changing. But we need more women in those conversations because these are the pension funds and the did partner investors who invest in capital, in women and make those giant endowments. Those are all run by men. And now they're hiring, you know, a few more women. But we need more women investors. We need more women to understand investing and try. Like, the more you try, you know, big risk equals big reward. Buy some stock. Go on, Robinhood. You like Starbucks? Go buy some Starbucks. That's a public stock. You know, Bitcoin, too, is like one to 17 in terms of female to male. And that is a huge opportunity as well. Like what is Bitcoin? I'm sure everyone's thinking right now on this. Like, go figure it out. You don't have to buy a whole Bitcoin. You can buy a little piece of a Bitcoin. But I think women need to be playing in these circles and taking this risk with their capital. And it makes you feel more comfortable the more you're exposed to it. So I always say like to the men, you know. Bring your sisters, your daughters, your mothers into these conversations, your wives, champion women and wives and significant others should be in every single conversation with your financial manager. I don't care if you don't understand it. Sit there. You will understand it. After you go to a few of these meetings and we'll learn more and you can ask questions about why you're invested in that or what it means to be invested in a real estate fund or whatever it may be. So I just say, like, expose yourself, take more risk with your capital and talk about money. I mean, my friends clam up when I'm like, hey, you guys want to talk about, like, what you're investing in right now. And it's like it's like the air is sucked out of the room. You know, that some people work in finance and it just blows my mind that they don't own any stock. And so I really believe women need to build their pool of capital, build their own family offices, and also know as a woman that you have you own 50 percent of your you know, however, the wealth was created. If your husband worked and you stayed home, you own 50 percent of that. You can decide where that goes. And so I think women just clearly I'm on my soapbox now, but they need to take more risk.
[00:27:02] Yeah. And I think risk aversion is one of the things that, like you were saying, like we need to matriculate out of the next generation coming up.
[00:27:11] You know, it feels like it was baked in and finding out those levels. I think it's bred any kind of a version for me is always bred through ignorance. Right. Anytime you have an exposure, like you're saying, just go along, go to the meeting, become exposed. Make those terms start washing over you. They become very un mystified. Once you hear them enough and you put in the sign value to them those kinds of things, I think that integrating into the high school measurements, you know, young women leaving high school should understand the stock market. And I can promise you about zero point two percent of my entire graduating class from high school, including and the women will probably point zero zero one percent understood or even grasp that the tenants of the stock market, let alone how to how to garner them, you know, and then you say people clam up like even people who are in finance and things of that nature. I do. I think it's based out of fear. Because I think it's fascinating to talk about, especially the areas I don't know of airline ticket until I climb through, but I don't have this kind of like fear based reluctance towards it. And I believe that education is the great equalizer. And so I think that encouraging young women who I run into a lot of artistic circles and encouraging artists like that, that does not give you a get out of jail free card from understanding the ins and outs of the American banking system.
[00:28:29] What are you talking about? We all function in this society, you know, and understanding the tenants, the core tenants of an axiomatic values of some of those are imperative to breaking down the gender bias.
[00:28:41] Yeah, it is interesting, having come from the acting career where you make a large you know, I'm just thinking of artists because I've learned a lot about them, especially through being a venture capitalist. We have a lot of celebrity investors in my fund. And it's interesting, when I pitch a potential investor and they happen to be a celebrity and you fall in two buckets, like either one is like the celebrity who made a chunk of change and spent it. And every time they make a chunk of change, they spend it. And then there's the celebrity who is like, I, I know I need to save this. And I am going to learn a little about investing. I am going to find a financial manager. And those are the like, you know, all the biggest celebrities, you know, who've had these like careers of longevity, who are able to then invest in their own pieces of artwork and produce their own movies because they then have the capital to do that. And so I find it's this sort of like up and down thing in terms of how artists invest. And yeah, it's I do know a lot of artists as well who just kind of check out and it's like, no, you will have. You'll have more flexibility in your career, too. Like investing is for everyone. It's not. And you don't have to have millions of dollars to invest. You can go buy a stock for, you know, 20 to 50 to 100 dollars, whatever you feel like putting aside. And I always like to talk about that. There was this Fidelity study done where they studied Fidelity, did this big study and said who made the most money in the stock market? And it was the people who forgot that they were invested in the stock market. So I like to think I like to tell people that so that you can think about how to invest. Don't get hung up. If the market goes up and down, just hold on. You're in your 20s to thirties when you like, you know, most people don't have any cash. They're just starting to try and build their careers, et cetera. Just every once in a while to go put some put some cash in the stock market. Fifty dollars, hundred dollars, whatever you read about some stock, you know, that seemed interesting to you or you believe that, you know, whatever some sort of like you buy some PMG because everyone's scrambling for toilet paper or whatever it is like. Just think about a reason why you might buy that stock because you believe in that company. And then just leave it there, leave it there, watch it grow, and then you take it out as needed. But I think that that's how you should think about investing in the stock market.
[00:31:26] Absolutely. I want to pivot a little bit before we end up rapping because I have my own personal demands from this podcast. And one of them is to pick your brain on my head. The area that is is kind of near and dear to me. And I kind of want to unpack a little bit of what you did on the Valley Girl show because of when it was started. And we got this little preview of you were talking about like nobody was doing it. And it was this weird monopoly between being pulled down off YouTube and all of these different things. I'm curious, when you went to curate, were you the sole curator of your interview? Questions and research? And when you went to speak to these people, where did you draw your inquiry's from? Did you have this written script? Did you look at everything that you guys were garnering about them and think, I'm going to ask them this, this and this? Like, how did you kind of choose you interviewed Elon Musk. You interviewed a lot of like it wasn't just what you got into the flow was like early.
[00:32:21] And they were all such early stage startups. And Elon Musk, I think, and I both probably feel like that is an interview we wish didn't still exist.
[00:32:32] That's what it is.
[00:32:34] I don't know. He was very cool. It was probably one of his first press interviews. No one had even heard.
[00:32:39] Yeah. He looks like a babe in the woods on. Yeah, that I did. Watch that one. Yeah. Jessica Alba too. I was telling you, I was like. She looks good. Then I was like, well, she always looks good. But then I realized it was a little bit older. But I'm curious, how did you kind of curate your interview question process and who did the editing? Did you have any handle in how the editing and production was done or were you simply the host?
[00:33:03] Such good questions. So season one, I, I went to my Nickelodeon show and then filmed it on a hiatus out of my parents garage. It was a disaster. I hired my brothers were much younger than me and duct taped lamps to the wall. It was such a mess. I knew these sort of editor guys from high school who helped me out and put together those first episodes, which I just cringe thinking about. And then after that, I went back to the Nickelodeon show and I I am so grateful because like Alby Hecht, who's now runs HLN, the Ajoy Network. But I basically said to him, I said, hey, can I sit in on production meetings? Like, I don't know how to run a show, it turns out. And he was so nice. He just kind of was like, yeah, sure. So I went in and I learned about, you know, the production design and lighting and just how they thought about that. And then I started studying like The Ellen DeGeneres Show. I mean, she's still one of my idols forever. Like I would just say to me. And just what she did. And I liked that it was so positive. And then it sort of became this like we called it the Valley Girl because of Silicon Valley. But then it became this like a Valley Girl thing where everything turned pink and we just ran with it. It was a very pink talk show. But every season got a little better. So then I came back and I hired a small production team and they helped me film. And that's when I learned about, you know, like a multi camera shoot and how that worked, because on the Nickelodeon show, it's just a different style of filming. This is like, you know, I'd be like, how many cameras do I need? How. What's the least amount of cameras that I need? Yeah. I don't want to pay any more rent movies than I have to. And so we started a three camera shoot. And then every you know, once you create a really solid format and you know what you're doing in terms of format, then you can kind of branch out from there. And just thing came to fruition. Games that people liked to play, we continued to play. We just continue trying to get people to eat. Edible co*ckroaches like that did not go well, you know, like your true story. Like there were things that people freaked out. People are really scared of reptiles. It turns out I just was like this any fun anymore? We're not going to do nothing, but. So you you build upon that, so every season I'd come back with new sponsors or whatever and be like, OK, we can use a lot of the props and things from last season and just like put a nice shine over it, you know, and there are certain seasons that definitely stand out to me, especially once we got to television was just like a different level of production. But then we would you know, I remember we we got a jib, we borrowed someone jib, which is like sort of hanging camera so you can get that cool hanging shot has a tiny, tiny room. And it just made it. It like brought it to a whole nother level. We from the Nickelodeon show, there was a lot of music and I had one of the music guys helped me put together like a music thing is like a valley girl. Little funny sound. Intro song that we cut together some fun clips of the show on. And in terms of the questions, I mean. I'm sure you're asking also because as a talk show host, there is no books on this. Right. I read everything. There was like the art of the interview was like that wasn't helpful. Hi. You know, there's really no books on it. And what I would say, having done thousands of interviews and and also been interviewed thousands of times. I really appreciate that you do your research. I think that says everything.
[00:37:03] I'll never forget this one interview I had on Fox Business and. We were on camera when I realized she had not done an ounce of research. And sometimes those shows move fast. So we give everyone the benefit of the doubt. But it's like, you know my name. Know what I'm doing.
[00:37:19] Like, know why I'm here? And it's fine in those situations. If you ever are being interviewed, you should just know that as soon people have no idea and just kind of interrupt and like, give them your whole spiel. But I really appreciate people doing the research. I did just we would book and we would film like, you know, a whole season in a week or two and I would do up to five interviews a day. I don't know how I did that in my early 20s. Like, I now think about that. There was I did some international interviews, too, at conferences and stuff. And I remember there was one day I did eight interviews and I was like, I can't do that again, because you're right, you're on camera. People expect a lot of you. You need to be on point. But yeah. So the first probably Four Seasons, I wrote all the questions myself. Of course, I would get input. I would ask PR. I work with the PR teams. I would always try to get different things so like that no one had talked about. So like with Sheryl Sandberg, I found this weird tidbit online somewhere that she had formerly been an eighties workout instructor. And I saw it and I apparently had I broke that piece of news. And if you watched that episode, she is shocked. She's like, I don't know how you bounce. And I was then quoted like three times in The Wall Street Journal or the show was that was the moment I sort of like, wow, this is crazy. It's like according to the Valley Girl show, you know, Sheryl Sandberg used to be a workout instructor. And I think you want to find those tidbits. And for me, I didn't want the PR fight a version. We would interview these CEOs who had been trained and trained and trained. And I would go in with a bunch of questions and know what I wanted out of the interview. And in the beginning, if you watched those first episodes, you know, I mean, they really haunt me because I didn't know how to do an interview. I just write a whole bunch of questions. Then I started being like, OK, these are topics. And here's the questions I'd like to ask under every topic. And then also, can I make it funny? And so, you know, it evolved like anything. No one's good at it the first time or the second or the third time. But I worked really hard on those interviews, especially at the end and then when we were on.
[00:39:37] We were on Fox in local Fox and appearance's go in and we were poached by. CBS CapEx in San Francisco. And when that happened, I was working 24/7 around the clock. The stories I could tell you from that season. I had moved the show to L.A. and then we would have to turn it around and get it to San Francisco. We would have to close caption it. I was not sleeping. I was newly married, had a baby and was contemplating raising this fund. And I my husband finally sat me down and was like, so this is not humanly sustainable. Yeah, you can't actually do this. But that was when I brought on a writer just to help me with, like monologues because the format had changed a little bit and I couldn't turn around these episodes in time. And the writer who I brought on her name is Liz Hanah, and she is currently b hottest like writer in Hollywood. After she wrote the Valley Girl show, she'd probably like, please never talk about this again. She's after her. She wrote the Valley Girl show. She wrote the Post with Meryl Streep. And so now she's written The Long Shot. She's on every cool show coming out as a writer. She's just she's awesome. And I am so excited to continue to watch her career. But she was funny and she did a really good job coming up with some jokes. And you need other people in there, too.
[00:41:00] At a certain point to just get all of the work done. But I really did. Ultimately, if you're an interview host, you're the one saying it at the end of the day. So if someone else is writing your questions for you and you should think about this in terms of moderating panels or giving presentations, like if someone tells you to say something that you don't feel comfortable with, you're representing yourself. So never say that.
[00:41:23] So we had not with necessarily with Liz, but there were situations where someone would say, oh, you have to ask them about that or you just need to go with what you feel comfortable with. And those were the lessons I learned. Mainly like those are more of like public interviews. When you do it in front of a large audience or what have you.
[00:41:42] Yeah. So I did all the writing for the most part until it came on and I did an extreme amount of research. And then also just how do I come up with an idea like I mean, some things worked and some things didn't because I was trying to make technology approachable. And at that time, it wasn't. It was. People just didn't get it. They didn't understand hardware. They didn't understand software. And so I tried to make crazy analogies. I remember we had these, like, equal guys on one time.
[00:42:13] They were running this company called Equal Field. I filled like a wagon with sugar, like equal like the steps, the sugar steps to sarco.
[00:42:23] It's not even funny when I'm telling you about it, but there are things like that were it was just it was fun to come up with and we would come up with just crazy games. And some people still bring up the Fab Cup to me, which was basically just like a rapid fire questions game. And I think we ultimately at the end call it rapid fire questions. But in the beginning we called it the fluff cut because it was this fluffy bucket. And then I learned that that was like a p*rn term. And so you just I mean, yeah, like I could tell you all day, but yes, I, I had my hands on everything. I thought I had to be the last person to really work with the interviews, even when Liz came on. Yeah. I just needed to know these people through and through and really figure out what made them tick. And if I didn't feel like I had enough information, I'd like reach out to their assistant or I would just be like, give me something. Give me some, like, fun fact. Like, I don't know, you know, I don't know anything about this. Yeah.
[00:43:24] And it does. And it differentiates. I mean. Well, back when you were doing it, as well as social media, I feel like I can find any little skeleton. I need to know if I'm looking for something.
[00:43:34] But back in that point, it is I think there was a lot of like old school reach out to even just five years ago. It was just a different game.
[00:43:42] And I think it's it's awesome because it's still the Wild West. But I also think I did a podcast recently where I was interviewed about I've started, you know, five podcasts over the past two years. And people are asking me about, like, you know, you seem to have this down. And and I'm a very organized individual. I get very creative in my organized space, you know?
[00:44:02] And so I have these these ledgers, which is why I tend to redo systems that I have. But I it's actually a pet peeve of mine. And I used to think it was because I'm a nerd. I love academia. You know, I always did. I have a master's degree in art history, which just means I like to go to lectures. That's pretty much it. You know, I like to just go and sit around those people and talk and and and essentially my issue with podcasting is not that it's the Wild West, that there's all this like anyone is doing anything. It's that the lack of structure. Like I just a lot of times if someone had pulled up a podcast that it was two hours and ten minutes and I was like, girl, you are asking it from me, but I will give it to you. I will give that to you. But I for the first 10 minutes, the host didn't tell me anything about what I was expected to hear. Whether or not there was gonna be more than one or two guests, like I couldn't figure out the format. Was she going to start reading her diary? What was going to happen there? You know, and I'm down with a lot, so I just. But there was no forecasting. And then when she did get her first guest on, I had realized very, very quickly that she didn't even know she hadn't even spoken prior to hitting record, like she didn't know how to pronounce one's name, let alone anything more than a bio that she had scrubbed off line. And I saw in the interview, I keep telling people, you know, I think that there is a slight onus for anybody who's going to get online and interview someone else that you you should do research. And how much that is, is however much time you have or how much you want to invest in it. But as someone put forth some kind of a structure and research, otherwise, let's not call it a podcast. Let's call it your daily musings. My twelve year old has a podcast. It's got more structure than 90 percent of what I find, you know, and maybe that's because she doesn't want to upset me in here. What you're hearing right now. But I think that there is a responsibility to start passing things out and it will probably come, like you said, with your show, eventually you start to find a beautiful narrative. But I do think that podcasts lack research and structure, and it is kind of daunting, especially to be interviewed when you go on someone's show and they're like, so what is it you do?
[00:46:07] Why am I? Did you find my name in the White Pages? How is this happening?
[00:46:12] You know, I completely agree. And people like being able to depend on something. You know, you get like that carpool karaoke show and it's a very simple format thing. Carpool karaoke in the car. And people love it, you know, hook off with a happy show. Very simple to follow. And I think people. Yeah, I think you're you're completely spot on that people need that structure. And I was actually thinking when you in the beginning, when you're like, this is what we're going to talk about. There's that like sort of like just a good general format to go by is tell what you're gonna tell him, tell him and tell him what you told him. And it's like a very simple format for any show and any research paper.
[00:47:02] It's the perfect paragraph.
[00:47:04] I'm bummed we have to wrap up, but I want to turn now towards goals that you have for the next one to three years. And it's important. I will not ever omit or dodge the current contemporary times. And you were alluding to earlier. So not only are we in the midst of the Cauvin 19 pandemic, how we are also in the midst of the tragedy, the pre cursing and post khaja and that tragedy with George Floyds murder and some of the riots that have happened.
[00:47:31] I'm in San Diego. You're in L.A. There has been a great deal of unsettling and disease with American society. And I'm an optimist. I believe that we're going to come out of this better. I hope for the sake of honoring George and as well as the entire community that he is representing, you know that we can do that. But I'm wondering with your company and your your goals reaching forward with both of those two things kind of compounding and coming into our reality, has it shifted or transformed your goals for the next one to three years or have they stayed the course? Have you doubled down? How does anything look for you? I mean, for all of your endeavors, you know, but for halogen in particular.
[00:48:15] I mean, yeah, like our goals changed at the beginning of Cauvin. And I am I'm devastated about what's going on and I'm uncertain about what's going to happen. Now, we may have to completely transform our goals again. You know, we invest in early stage companies and sometimes there's three people with an idea in a room. It's the riskiest asset class, which is why we do 30 deals per portfolio. And, you know, but it hedges in terms of like if you're an angel investor and you invest in a one off deal right now, it's probably not a good time to invest in a one off deal because, you know, at that stage, it's very likely that I'll go under. They say you need to do 10 deals in order to really see some payoff. And so I feel like our strategy has worked thus far where we invest in these early stage companies. We do 30 deals per portfolio, but week one of co bid. When you deal with early stage companies, you're getting the calls first because we move faster, our companies move faster because they're smaller. So we're hearing 60 percent hits to revenue, 90 percent hits to revenue depending on the business. And so we had two in one week talk to all 62 of our founders. We just called them, got a hold of them and ah, one hundred and fifty item checklist for diligence. Quickly transformed into three things. Yeah. And. Does this company have run or cash through January because we don't know how long this is going to last, too? Based on our experience, you know, pretty quickly, like in a year or two, if a founder can perform, and that's something to keep in mind for founders out there thinking about taking on investment, like prove yourself follow through, especially in the first year or two, because your investors won't give you more money if they feel like you didn't follow through in those first couple of years. So we say based on our experience with these founders, can they execute and take this thing all the way regardless? And then the third thing was, is this business covered, sustainable and beyond? And so while we were about to invest in three new very risky deals that we didn't have experience with the founders, I basically said I put those on hold, which was devastating for the founders.
[00:50:40] And I said, hey, I'm not saying we're not going to we just need to go check out our current portfolio. And then we chose our top performing performing deals. We doubled down on those. And then we were we're early stage fund. We don't have billions of dollars to invest. You know, call me in 10 years. And that's definitely one of my goals. But we're still growing. So we have to be really, really thoughtful, as you always should with your capital. But we we tried to support every founder in every in some way. So we invested in some we hosted a pitch day for some and our our investors invested in some of those. We put together a whole list of resources from debt opportunities to credit lines to banks they could talk to. We had someone tracking the SBA loan, which changes still sort of daily. And we also, like, offered everyone a free hour of PR and other business services just to support whatever they needed.
[00:51:45] My team, Alexis and Ashley from my team, actually one of our companies was growing so fast. So some companies are doing really well. We have this company called Pride. That's like it's like a teenage zoom zoom call. So they're obviously taking off. And they were taking off a little before, but they were growing so quickly that Alexa and Ashley kind of took over their marketing arm for a minute. And now we've helped them put some people in place there. So we were actually helping operate some companies, doing whatever we possibly could. So in terms of goals, we're still hashing those out. But what I'm really proud of is that we put together those goals in one week and we've already executed the plan.
[00:52:27] And that's in two months. We've, you know, invested capital into our best performers and we've supported everybody else to the extent we can. And we continue to do that. And it was not our normal plan at all.
[00:52:42] I do hope, you know, down the road we're on our second fund. I do hope, you know, we raised fund three. We raised fund for and they continue to grow and we continue to grow our team because we're still a startup as well.
[00:52:56] I hope that investing in women is seen more as an opportunity. And I hope we hope that we can help prove that we already are a little with our data that we're collecting on our founders and female founders in general. And and then also just, you know, goals for the world. I hope everyone sees diversity as just an asset to every single business. That's something we're constantly thinking about. So, yes. So that's that's what I would say in terms of our goals. But setting goals is pretty important.
[00:53:28] Yeah. And way to pivot Scullin's 60 companies in one week into transitioning all of that over.
[00:53:33] I mean, do we have a team that all of it. Yes, it was a lot.
[00:53:36] It was I would not want to stare that down on that Monday, and that would be a little bit less. It's a several it's like a whole new cappuccino machine. That's not coffee. I measure everything in coffee cups or especial shots. That's like a machine has a whole nother purchase. That's your own personal barista.
[00:53:53] I'm wondering. So this is my final question. It's my favorite part. And everyone knows who's been listening to me for the past couple of years. But I'm wondering if you walked up to someone in office, a safe social distance or they approached you sometime this week and it was a young woman or a female identified or non binary individual. And they said, listen, Jesse, I'm so glad I caught you. I just finished up learning the entire ins and outs of the film industry. I went to UCLA. I got everything done by buttoned up. I know all bit about it. I've gone to a ton of auditions and I have film industry experience and I've decided I'm going to keep all of that. And I'm also going to pivot now and going to starting my own investment fund and come from a family that's got some background there. But yeah, I'm just going to like, you know, bootstrap it and get going. One of the top three pieces of advice you would give that individual knowing what you know today.
[00:54:49] I would say go for it. I really think especially women, we need more female investors across the board. I would say baby steps just go one step at a time. There are mountains and mountains to climb. And then this goes for fundraising across the board, whether you're fund raising for a fund or for a business, because most people don't have a million dollars to do starting a business in their back pocket. In fact, the majority does. So they typically go raise money. I, I am sort of frustrated when women in particular come to me and say, well, everyone said, no, no one will invest in my company. And I say, OK, well, how many people have you talked to this l. Like, eight. OK, so that's not enough people. I talked to five hundred for my first fund. No joke. And you should plan on going out and talking to at least one hundred. If in 20 meetings you are hearing no's still go back to some of those people and say, hey, like what was the issue here? And it may be such a simple. Fix that, you could, like, throw a slide into your deck that addresses it. And it's no longer an issue. It could be something you haven't thought of before. But definitely listen in those situations. If you plan on going out and having 100 meetings, you'll raise it. You'll raise your your capital, whatever the number is. Just don't get weighed down by the nose. There's going to be a lot of that. And that's in any profession. But somehow it feels very personal when you're raising money and don't look at it that way. Look at it like I kind of talk to these incredible people. And then when they don't invest, say, can you tell me why? And usually shoots, like, has nothing to do with you. It's like, well, actually, like, most of my money is tied up right now, so I don't have any cash to invest. It's like, OK, well that's simple and it has nothing to do with my business or like we already invested too in too many consumer focused funds. And I'm like, oh, OK, I get that. They're trying to diversify their portfolio. I'll go back to their next fund. So I'd just say get through the nose and plan on having a hundred meetings.
[00:57:05] Nice. That's good. And I think you're being realistic, too. That's the scary part. And it's good. It's good to say those things.
[00:57:12] I think people can do at least 40 or you're like 100, 100.
[00:57:17] It'll probably be less so like that.
[00:57:20] Yeah. There's something probably vitally wrong with what you're doing if it's if it's 100 and all knows. But I think that's right.
[00:57:26] That's kind of the attitude of just go until, you know, there's the Hollywood formula. It's not about like, you know, quick breaks and stuff like that. It's like seven years where there's a mathematician that broke down. How long if you audition? Three to four times a week in Hollywood, it takes to make a big role, a main leading role.
[00:57:43] It's like an over. It takes 10 years to have an overnight success.
[00:57:47] Yeah. Exactly. And then it's like everyone's like, oh, they just got here and you're like, no, I've been holding it down a thousand percent. Okay, so I've got go for it baby steps and plan on talking to one hundred people and don't get weighed down by the nose. Just adjust as you go. Those are perfect. I love that Jesse. It went by too quickly. I'm going to have to have you back on. This was fascinating.
[00:58:12] This was so fun. Thank you so much. I really appreciate it. And I'm glad you're, you know, showcasing all of these incredible women because we need more people doing that.
[00:58:20] Awesome. Yes. Thank you. I appreciate that. And for everyone listening, I appreciate you. We've been speaking with Dressy--- Jesse Draper. She's the founder of Halogen Ventures and the host and creator of the Emmy nominated The Valley Girl Show.
[00:58:35] You can find out more about Jesse and her team and her fund on Halogen vc dot com.
[00:58:42] I appreciate all of you listening. I appreciate your time. And until we speak again next time, remember to stay in love with the world and always bet on yourself. Slaínte.
