Breaking VC Stereotypes: Power, Privilege, and Purpose w/ Jesse Draper, Halogen Ventures

Jesse Draper: I started, you know, at the age of about eight, I said I wanted to be a vice president or an actress, and that was because growing up while I interned at startups or watched my dad who was a venture capitalist, I should disclose, um, because you alluded to it, I'm a fourth generation venture capitalist. I think that a lot of preconceived notions come with saying you're a fourth generation of anything.

And, uh, not everyone feels happy about it. There's this whole conversation about nepo babies and I really don't like that term, but also like I didn't choose where I came from, you know, and I don't judge anyone else for where they came from. It's about what you do with it. And so I am a fourth generation, but I'm the first female.

And I think something I've learned even more recently, I'm always learning is that looks a lot different being a female. It's been a very different journey, I think, than my predecessors before me who were male, and I've learned so much from them. But it is a different world for women, and that's amazing and frustrating all at the same time. And you and I are doing great things to change it.

But so I started out saying I wanted to be an actress or vice president. Vice president sounded like, you know, a bigger word than president to me at the age of eight. So I was like, I wanna be vice president. 

SCS: Because that's more important. 

Jesse Draper: Because that seems more important.

It was a bigger word. 

SCS: That's right. 

Jesse Draper: And then I wanted to be an actress. My Aunt Polly, who I'm very close with, she was an actress and she was very successful. She's still very successful. She's on Hacks right now, and she's hilarious. She's so funny. She is a great writer, producer, and I looked at her and thought, okay, that's what women do. 'cause my mom was working incredibly hard raising four children, which by the way, is the hardest job. And I think that the data now says that that's worth like over $200,000 as a salary. So, uh, moms should be getting paid $200,000. So feel good about that. But I wanted to do something different.

And so I thought that was a traditional job for a woman, which is hilarious 'cause it's definitely not, and it's definitely the road less traveled for anyone being a professional actor. But I had that in my head. I was a scarecrow in eighth grade and that was my big moment. I started pursuing acting kind of as a career.

I did classes at ACT in San Francisco and then I went to UCLA School of Theater, Film and Tv. And I always in the back of my head. Knew I had to make it a business. I had my dad telling me things like, well, how is this gonna be a business? How are you going to support yourself? How can you be an entrepreneurial with this?

So I always had that kind of in my head. I went and was an actress. I had some success in some indie movies, and I was on a Nickelodeon show for a couple of years, um, that started as a mockumentary with my family members and turned into a Nickelodeon show that Albie Hecht Picked up and at the Hamptons Film Festival and brought it to Nickelodeon and it was fun.

It feels like a different career now. I mean, it feels like a different person, you know, as you grow, it feels. Yeah. I was like, my early twenties, I was living in New York and working in Brooklyn and Green Point, and through that I just was like, I'm auditioning. I'm spending so much time auditioning and I look just like all the people in this room and they're looking for, you know, a tall brunette or whatever, and I, I just feel like they're all much more talented than I am, which is still probably very true.

And I had this one terrible audition where they didn't even ask my name. They were like, turn around, turn around, click, click. Took pictures. No, no, no, don't speak, goodbye. And then around that time, I then went to the first Twitter conference because you know, I'd been on a Nickelodeon show, I was a z-list celebrity.

And, um. So I was invited to things like that and it was Twitter. It was like something I was familiar with in that it was a startup and I could see this tech thing happening and you know, let me take you way, way back when, where you saw, at the time we called it new media, digital media, like the transferring to Facebook and Twitter and uh, social media and people posting things online.

And that was just the beginning. And I saw something really unique there, and I was very inspired at this Twitter conference. I was like, wow, there's something really cool going on here. And you had Tony Robbins speaking and all these people, it was like the Kobe beef truck guy got like a hundred thousand followers.

And then he'd speak on a panel about how he got a hundred thousand followers and everyone, every celebrity's like, how'd you get a hundred thousand followers? And it was just about how you get the following. But I saw something really cool happening there. I was one of probably five women in that room of hundreds of people at this first Twitter conference, and I can still probably name them today.

It was like iJustine, this girl Sarah Austin. These like very uh, Shira Lazar, these very early women tech mover and shakers. And so while we were some of the only women there, I felt like comfortable with men in hoodies and men in suits, and I just felt like this was something interesting. So I went home, I started one of the first tech talk shows outta my garage.

Mm-hmm. I hired my brothers who I quickly fired. 

SCS: So this looks familiar here. 

Jesse Draper: Yes. She, Sarah's working with her brother who is here, who's lovely and they're partnered on many things. Unfortunately for me, that was the last time I partnered with my brother. Oh no, that's not true actually. We do deals together sometimes.

But they were in high school at the time. Right. And so they got like bored in the middle of interviews and they were like, I have to go to my friend's house. And I'm like, no, no, no. We're interviewing the CEO of Google right now. Yeah. And at the time though, not as many people were impressed by that. It was like I would do red carpets and stuff and like, I'd be like, yeah, no, I have this talk show and, and I'm interviewing the CEO of like Google.

And they're like. Okay. Like whatever. This is 2008, like you hear that now and you're like, wow. You have Eric Schmidt. So I started the First Tech Talk show. Fast forward to today. Ultimately we took the show to tv. We were distributing all over. I did everything we probably shouldn't have done. I didn't lean into YouTube because actually at the time I was on the Nickelodeon show and every time I'd put something up with my essence, Nickelodeon is part of Viacom. Mm-hmm.

And Viacom was in a lawsuit with YouTube because they were like, they're taking all of our IP and content. And so actually that's the reason every time I would post something, they'd take it down. And so I started being like, huh, because you know, you sign kind of your life away as this actor on these shows.

And so I said, okay, I'm gonna get distribution everywhere else. So I was getting passive eyes in, you know, restaurants. The, my gas station attendant was recognizing me. I was one of the first people to do that deal in airports, hotels, you know, and, uh, we were getting millions of views that way. Took the show to tv, were nominated for an Emmy, didn't win.

Lost to Eclipse Show, but were nominated and had incredible entrepreneurs. And through that, you know, you mentioned this earlier, I was only interviewing men in tech. It was Elon Musk before today. 

SCS: So he has to thank you. Yeah. Yeah. He can. Thank you. You know, Elon, if you're listening to this, he. You have Jesse to thank. 

Jesse Draper: He was awesome then, but he had just started Tesla.

And when I say awesome, I don't know, like people have such strong opinions nowaday. He was a great entrepreneur. I'm grateful to him for being on the show. I think both of us wish the, the episode would die. I should disclose that. It's like a Borat style. You know, pink talk show where I'm interviewing these entrepreneurs and not trying to make fun of them.

I'm making fun of myself, but I also put myself in a really ditzy stupid persona that... 

SCS: Why did you do that, by the way, I wanted to ask you that. It was... 

Jesse Draper: Why did I do that? 

SCS: Yeah. It was pretty strong with that ditzy persona, right? 

Jesse Draper: I think I, I was coming off of this Nickelodeon show and I, that was a character I knew I could play.

I wasn't used to playing myself. I was a professional actor. I was like, okay, well I'm a girl interviewing these tech guys. Not that they're not interesting, but I wanted to make what they were doing more approachable. And so I wanted to dumb myself down. And I think that's also, as women, something we tend to do is like, especially back then, like dumb ourselves down and make ourselves look stupid.

Like, oh, can you help me? I don't understand. You know? And it's, I think in some ways it. Helped my career and in other ways it was like the worst thing I could do to be taken seriously. Yeah. And still to this day, I think it actually has affected things in my career. It's brought up to me so regularly in the tech space, took that show out there, realized I was only interviewing incredible men and made an initiative to interview 50% women in tech.

Now, this is like 2008, 2009, when women did not wanna put themselves out there. In fact. It was like the opposite. It was like me asking Meg Whitman to be on the show and her being sort of not wanting to put herself in that scene 'cause she wanted to be taken so seriously. I had Meg Whitman like three times cancel on me and I never got her on the show, but I ended up getting Sheryl Sandberg before she'd written Lean In.

And that was a turning point for the show where the interviews became a little bit more serious. Mm-hmm. With the women, I didn't want them to look stupid. Yeah. I wanted to look stupid. Put it on myself. And I had Julia Hartz from Eventbrite, Beth Cross from Ariat, owned by Gap now, and like Secretariat, you know.

But I'm very grateful to these women forever because, and Jenn Hyman from Rent the Runway, and this was my first, I called it the Rocking Women series, and I just straight outta the gate, that season came out with like six just baller female episodes.

Now all those companies have gone public. Yeah. I looked back and I was like, God, I wish I invested in all those companies now.

Right. But after a few years of doing the show. I started writing small checks, small angel checks, negotiating sweat equity, and some of those did really well for me. And it got to this point where I had my husband and then I have this great little lean in group and they were really encouraging me saying, why wouldn't you start a fund?

You know, why wouldn't you do that? And when I zoom out, I saw this opportunity where. One, I was supporting women by investing in their media exposure. Women in technology specifically is what I was focused on. And then I also realized they needed funding and I was seeing incredible deals come through my show and I'd be like, you're a Series A company.

It's too early for my show, but like I would love to stay in touch and support you somehow. And so that was the impetus for me starting to write checks. One of those checks turned out to be a 26 x multiple return in 18 months. Wow. So I then had a track record. Mm-hmm. It was a company called Laurel & Wolf.

Benchmark came in, marked it up. I sold secondary and everyone else ended up losing their money in that deal, including benchmarks. So I sold at at the right time, still know the founder. I'm grateful to the founder. And then I was off. I pitched all my guests from my show, pitched 500 potential investors.

The first time you raise a fund, I think you don't know what that looks like. You don't know what an investor looks like. I'd have entrepreneur conversations, they'd be like, wait, I have a family office. And I'd be like, oh, I thought you were pitching me, but now I'm pitching you. You know, you just don't know.

Yeah. And so I raised $10.4 million for my first fund, and now we're on fund 3, 75 companies later, we have $5 billion companies. I still feel like we're just getting going. I mean, the, the game of venture capital is wild. And my story is wilder 'cause not many started as an actress. 

SCS: Yeah. So I wanna, I mean so much to unpack that, but I actually wanna start with your choice on your persona.

I know it, it feels icky, but you've not really spoken about this. And I think it's important because look, our children, they're growing up in a completely mobile generation. Yeah. Everything is recorded. You need to think through Yeah. Like the long-term choices that you're making right today. 

Yeah. 

What struck me was, look, you came from a business family, right?

Uh, yes. Women were viewed slightly differently, and so you didn't necessarily have role models. But as you were shaping this, you were sort of finding yourself. What would you have, I guess, done differently? Do you regret putting yourself out in that way? As you said, you know, it still has repercussions today because it is public.

Jesse Draper: I would say like I did have great role models. You know, my dad obviously is a huge role model. My mom and my aunt were incredible role models. In my family. And then I had many others outside, like Sonja Perkins who was at Menlo Ventures and even like my friend Rebecca Minkoff. So I did have great role models like just in my life throughout.

But you know, in terms of the persona of the Valley Girl Show, to be clear, this show that, probably anyone hearing this has never seen and now is gonna go Google the Elon Musk episode where my boobs are out. And it's just like, what was I thinking? I think something I took from my acting, it was a time where Lindsay Lohan and Paris Hilton, where scantily clad on the covers of magazines.

And what I was actually trying to do was say like. Today, by the way, I would say Paris Hilton's a genius, but back then I'd say what I was trying to do was celebrate these brilliant minds. Mm. And it was before these guys were on the covers of magazines. Like I always saw that. I was like, I wanna put these people on the covers of magazines.

I grew up in a startup world. Why aren't these incredible innovators being portrayed as heroes and role models? And so that was something I was trying to do a lot of them. And this is the kindest way possible. I'm a total geek. I'm sitting here like having an interview with you about venture capital, like I'm a total geek.

But I think a lot of them, they weren't used to putting themselves out there. They were not entertainers. So I wanted to be the entertainer to help put them on a pedestal. I think that's what I was trying to do. I was also trying to dumb myself down, which is something I'd been taught to do, make myself small, I hope.

And I'm sure women hearing this can relate, like we make ourselves small. Mm. It doesn't matter if you're scared in a parking garage and some guy comes up to you who you don't know, or if you are in a boardroom and you're the only female on the board. It's just this instinct we've been brought up with to make ourselves small.

And I think my entire journey from that moment has been me trying to make myself. Heard and bigger and take up space as they say, you know? Yeah. That's really, really important. And I think I was always like, oh, just pretend I'm the dumb one. I'm the pink one, I'm the whatever. Mm. And do I regret it? I really am a person who lives with no regrets.

Like I certainly replay things in my mind over and over, as most people do, where you know you're missing something from the first time you witnessed it, and you need to replay it. And I think as you age. You have a different perspective on those moments? Yeah. I mean, when Elon came in, I thought he was pretty incredible.

He was 30 years old, he had triplets. He like hadn't slept. He was like, Hey, I need a coffee. And I was like, where are my parents' garage? So I don't really like have a. Coffee machine, but um, he's like, it's okay. I see microwave. Can I just like microwave a coffee with, I'll just make up my own makeshift latte essentially.

Yeah. And he was just really cool. I really thought he was a, a nice guy. I don't agree with everything he is, but I mean, that interview actually, I don't think it was the biggest interview I did. I think, you know, I had like Jessica Alba. Even Sheryl Sandberg did really well for me and Mark Cuban, but I, I am grateful to him.

And who knew then what he was gonna accomplish. 

SCS: Yeah. Yeah. 

So the reason I picked that up is you also wrote a scathing article, which was really in a moment of frustration about investing in women, it's not a charity. It comes from this place though, that women have been told to play small. To reduce ourselves and therefore, I mean, you know, I'm here also because we were hosting a group of women who are taking out space in their family offices Yeah.

That are using their power of their check. And we did it in a closed door setting. And one of the things that came up during that conversation was that it was very quick for them to be given the charity portion. Yeah. Which now we know we can use Donor Advice Funds to invest, stuff like that. But why are women put in this bucket of charity and how do we flip the script?

And how have you done this? You are doing it right essentially, but what do you think needs to change here for women to really wield the power of their check? 

Jesse Draper: I wrote this article a couple years ago called Investing in Women isn't a Charity and you're gonna have to bleep that too. And it was one of those things that I actually don't think I realized what a life of its own it was gonna take on.

I mean, it's put me on a speaking tour around the world to talk about it because so many women felt that way. Yeah. And especially the women in our industry where we're trying to invest and we're proving ourselves over and over every single day trying to say, look, we're doing this too, don't take us less seriously because we're female, but we are seen always as the check writers to charity because in the past in history books, men passed down the pocket books, to their sons, to their sons, to their sons. And I said...

SCS: Like, Jiro Dreams of Sushi. 

Jesse Draper: Yes, exactly. Exactly.

Jiro Dreams of Sushi. And what about the women? And I actually feel like even in my family who was incredibly supportive, like my dad has funded incredible women, I felt supported, but I also felt like, okay, well. I feel like I'm being put in this philanthropist bucket and I had to fight a little bit to be taken seriously as the investor.

Now we're all on the same page, I think. But that was something I learned. And I actually see in friends of mine whose husband just had some great success at a company and she's an incredible financial mind as well, and I see their family office sort of pushing the money towards women in the philanthropic foundation bucket, and I'm like, make sure all those women in your family are also in the for-profit investment bucket.

That's right. That is so critical because anyone can give away money. Yeah. But can you make it? And women take more calculated risk. There's so much incredible data around investing alongside a woman. And I'm not saying it's women versus men, though some people will still take it that way. Mm-hmm. We wanna invest with men, but we need both of those things.

Men, I always say have this like gambling mentality where it's this, I feel good about this, I'm gonna write a check. And by the way, I appreciate that so much when I'm fundraising because I know that they'll meet me, they'll take it into account, they get it, they're like, I feel good about this.

I'm gonna write a check. Right? And then women, I'll spend six meetings. Now we have a three meeting maximum like. Six meetings, like, why can't I get you there? What is the problem? And they're so risk averse. They're like, I feel more comfortable, you know, giving this to this like education charity or this whatever.

And I'm like, well, we can make more money to give to that education charity. And actually you're making more of an impact because mm-hmm. What we do at Halogen, we invest, there has to be a female in the founding team. We make sure there's a female in the founding team. And before you ask, I do have five male CEOs out of over 75 companies and we love men.

There has to be female. I get so many funny questions like, what if a guy works there? I'm like, we need thousands of men working there at a billion dollar company, hopefully. 

SCS: Yeah. So I think it all comes from a perspective. I mean, even the way that I've let all my organizations, it's always been from an inclusive standpoint, right?

Yes. It's the power of diversity that we all have different strengths and it's almost, sometimes I cringe when it's, you know, they call it a women's network, whatever, because frankly we are still in this place where we need to have certain close circles have these conversations about, how do we be, frankly?

Yeah, right. How do we step into our power and just even have these conversations within the family, which I wanna get to because you've said in the past, I mean, you would travel with your dad, you went to China and you were shunned right into a room because it's, it's for men, usually businesses for men, which shaped you.

And now you're in the space where you are getting women to invest. You're saying that investing in women is good business. And also on top of that, you're taking a thesis with Halogen on the future of family, which affects women still disproportionately. So there's some element of where we are, where we have to be, and how we have to work together.

Talk to us a little bit about, you know, your just personal journey on, on figuring out, okay, how do I shape my investment thesis? 

Mm-hmm. 

How do I even have this conversation in my family about, look, I wanna be doing this in this way. Walk us through that, because a lot of women, frankly, are going through a similar path that you are.

Jesse Draper: I don't work with my family other than doing deals like I have my own fund. My dad has his own fund. My brothers, both my brothers have their own funds and my sister is a great investor. So we all work separately, but then like we just did a deal together when it makes sense. But we all have very different thesises.

Yeah. And we all go raise our own LP capital, which is hilarious. 'cause you'll bump into investors and they'll be like, I just met with your brother, and you're like, oh God, which, which investor is gonna write a check to us? I've built an incredible firm. I'm really proud of it. I have an amazing partner named Ashley Balla, who I couldn't survive without another partner in New York named Jennifer Kwan Mandelbaum, and I think you can't do anything alone.

So I would first say that, and then in terms of my thesis, any good investor and venture capitalists, like we're early stage investors, right? So we're betting on the future. What does the next 10 to 20 years look like? We're betting on the future, we're predicting trends, and this is something else I'd say to any woman looking to get into investing or take that first risk or write that first check.

You're gonna learn and you are probably regularly predicting trends that you don't even realize in your life. I started in consumer and I loved like walking into SoulCycle and smelling the lemon, and they've, you know, created such a brand fully with a scent, with the logo, with this like passion, religion, biking thing, and you know exactly what that is.

And I liked to find those next brands that you could just live and breathe. And I would look at regularly. And you know, I think those are things that you can start predicting as you see those behaviors changing. It's a great brand that built a following in a really unique way. Mm-hmm. And I'm looking for more brands like that, and that's kind of what got me started.

So anyway, in terms of thesis, every fund, we went out and said, okay, fund one, what's our overall thesis? Fund two future of work. You know, what's work gonna look like in the next. You know, 10 to 20 years. And then we looked back actually at fund one and two and said. We have 12 investments in childcare and they've doubled in value and they're doing great.

So let's see what happens if we double down on childcare. Like that's an amazing thesis. I went out, you know, you kind of do this thing where you pre-market, you start telling people about what you're gonna raise for. I had a lot of people say, childcare is not that big a market. Is it really a big enough market?

Wow. I don't know. I'm like, well, it's $548 Billion dollars, you know? But I always sort of say like, challenge accepted, we can go bigger now. Everyone's seeing markets in trillions. And so we looked at the family and we said, how do we support the family overall? And that's a $7.5 trillion opportunity. How do you support the family at work, at home, the physical health.

And the financial health of the family. And now this thesis has been amazing for this fund. We have done some incredible investments from the first credit card for childcare and tuition payments where you're supporting the family financially, all the way to childcare benefits for hourly workers. Our company called Mirza, we have head childcare locations. We have Upwards, which has 66,000 in-home vetted childcare locations, the largest network in the country. Our companies are doing incredible work, making incredible change and making an impact. But ultimately, bottom line is these companies are gonna be multi-billion dollar businesses, and I'm seeing every company should be incorporating AI.

I mean, that's on the tip of everyone's tongues. Mm-hmm. I think even when I was running the Valley Girl Show and I was already predicting these trends for my show, like, what's hot? What's new? We were already talking about AI, so it's kind of interesting now. I mean, that was 15, 20 years ago. Yeah. It's not a new thing.

And I think any investor who thinks it's a new thing and is creating a thesis solely around that, I would be kind of concerned writing a check to them because they should have been knowing about AI for a long time. So all of our companies have always been thinking about AI, integrating AI. I think it's ultimately gonna make all of us in the world work smarter, not harder, you know?

Um, and I'm really excited about, I mean, I use AI for everything from putting together like a diet plan. 'cause you know. I'm always trying to lose those pounds to like putting together a social media plan to putting together like a draft of a deck. Mm-hmm. I mean, I think people don't even realize we just had a company Trust and Will, it's an estate planning online business that's doing really well.

They just put together like a custom ChatGPT for just the board. I'm on the board so I can go be like, what's the revenue gonna be in 2026? Hmm. And just things like that. Yeah. Blew my mind. Where now I'm like, we gotta do that for our fund, for everything. Yeah. 

SCS: Fund three is future family because you're doubled down on what you saw to be the emerging trends of frankly, where America is today, right? Yeah. Like it's kind of sad. We were talking about this, that America's the most developed country and yet childcare, you know. The parental leave situation. Talk to us a little bit about where we are in America today. 

Jesse Draper: Childcare is broken in the United States. It doesn't make any sense, and I think whenever I speak with people from other countries who have great childcare that's provided by the government, they're blown away.

In the United States, 99% of society can't afford childcare for children under the age of six. Children, the ages of zero to six. That's such a critical time to make sure that they're not neglected, that they're well fed, that they have structure, and no one can afford a private preschool. Also, private preschools doesn't condone two working parents typically.

Those preschools are even more unaffordable. We're talking like anywhere between $50,000 and $90,000 a year for a private preschool for a child. Doesn't make any sense. You know, our company Upwards is tackling this in terms of they are basically supporting a network of childcare facilities that are in people's homes that are vetted, and so those are more affordable.

They also offer some government benefits. We have a company tackling like childcare benefits for the hourly workers who can't afford the childcare. Say you're working at Costco in the early hours, you need childcare for that. You need to pay for that. Your salary may not support that. And so Mirza is one of our companies that's tackling that and sort of plugging the government in and making sure these corporations know they have that access to those corporate benefits.

But it's broken. I mean, even, lemme just tell you, my kids go to school in Los Angeles, major Metropolitan City. We're in public school. Even at a public school. I have two days that are shorter. So two days, my kids in public school get out significantly earlier. Like just nothing makes sense, you know?

Mm-hmm. Even the summertime, three months off, parents have to then pay extra for their camps and things like that. It's just not doable for two working parents, but you have to have two working parents to provide for these children. Yeah. It's making people not wanna have children, and it is just broken in every which way.

I mean, I'm barely even scratching the surface. There are so many issues that we need to solve. We need more, you know, government support. We need better public school education that also has more normal hours, where also recreational activities, such as sports, et cetera, are incorporated into the school day.

Versus then if you want your kid to play soccer, you want your kid to play basketball, you have to shuttle them around after school to all these extra activities like. Why aren't we just putting all of that in school where they learn all the sports and you can lean in as they get older. Um,

SCS: So that's where Hop, Skip, and Drive comes in, right?

Jesse Draper: Yes. Hop, skip Drive is a great transportation company we're invested in that helps you be super parent where you can get your kids to different activities and it's a safer Uber essentially for children and also the only Uber service that fingerprints their drivers. Interesting. So you can think about that next time you get into a Lyft or an Uber.

Yeah. There's so many issues in society. We are. Completely failing families today in the United States. 

SCS: So what are your priorities? I mean, childcare was one. The financial? Mm-hmm. Like. Construct around it is one what, what else can we look forward to as you're launching this fund, right? 

Jesse Draper: Yeah, so we're about to close this fund.

We did a big study on what families wanted and something that was very surprising to us, but shouldn't have been, is they wanted more scheduling tools. Mm-hmm. They wanted more financial management tools and so we actually leaned in there and found this great company, Kina Rewards, which is the first credit card for tuition payments.

It'd be an equivalent of like a healthcare card of sorts or an insurance card. It's like a rewards program as well. So we're looking at a lot of companies that solve the financial piece too. And then we're also looking at the healthcare piece. The last resort for families will be going into the hospital for anybody.

We'll be going into the hospital post covid. No one wants to go in the hospital. What are the at-home diagnostics tests? How do we make sure that families can afford those and that they're covered by insurance? Who are the new insurance providers. And so we're looking at that as part of our thesis too.

SCS: Yeah. And what's the business opportunity here? I mean, we are, we're always excited by, yes, the impact that you'll create, but for your LP that's investing in it, what's the exit runway for a company like this? 

Jesse Draper: I found this really secret, exciting pocket where. You know, it's undercapitalized and has been undercapitalized because primarily I think women see this more than men.

You'll have these conversations and they're like, you know, what do you mean? I have kids and it's like, not a problem. And I'm like, well, does your wife stay at home? Yeah. Okay, cool. Well, I don't have a stay at home wife, so it's like very different for me working and running a company. And those conversations are important to be had, but in terms of the opportunity, these are gonna be billion dollar companies.

These are massive opportunities. You know, I'm talking about healthcare, I'm talking about FinTech, I'm talking about, I mean, the tuition alone, like one of the founders started SoFi and so there, I mean, this is an incredible opportunity too. The tuition payments, I mean, that's hundreds of thousands of dollars a year for some families. So that's a really, really big opportunity.

It depends what vertical you're looking at, right? Yeah. We only invest in billion dollar markets. Mm-hmm. So childcare is definitely a billion dollar market, as I mentioned, $548 billion, but it is early. And so you're looking at comps and you have the care dot coms of the world, but no one's even seen childcare facilities. I see a lot of opportunities. One of our new investors is the state of Alabama. They were really, really excited about investing in our fund. We're the first out-of-state fund ever to receive funding from the state of Alabama. It's through this great program called Innovate Alabama.

Alabama in the United States is ranked 50th for female founders. So they wanted this to be like a catalytic investment. Yeah. They also love to the future of family thesis and one of our first investments there is a childcare facility company with some tech enablement. We also have one of these called Brella in Los Angeles, and I'm starting to see this as a massive opportunity where people are looking for more cash businesses, and I feel like I've found this magic carpet where all these companies are doing really great, they have great tech, and it's cash instantly because people have to pay for childcare.

There's a big opportunity there.

SCS: And there's a recurrence there. The lifetime value is long. Yes. Because your kid's there for X amount of years. Yeah. 

Jesse Draper: So when you talk about exit value, I mean this one solo in Alabama, even rolling out into all the districts in Alabama that they want. That could be a billion dollar company alone.

Mm-hmm. But when you look at ones across the country in every state right now, you're seeing private equity roll up everything from pest control companies to air conditioning companies, to laundromats, because people want these cash businesses. There's a massive opportunity in childcare, and we need the investment in childcare as well.

SCS: You have completed your fundraising journey. Hopefully. I, well, for this fund, for this fund. Always be closing, right? You're always fundraising. A B, yes. A, B, C, A, B, C. Always know your ABCs. 

Jesse Draper: A, B, RI think it's uh...

SCS: always be raising.

Jesse Draper: Mark Schuster, good friend of mine who runs upfront always says A BR. Yeah, always be raising.

SCS: Always be raising. I like the C because you need a raise and close the conversions. Very important because the six meetings is too long as you said. So true. So what are the lessons learned there? I mean, it's kinda interesting. I know you've been asked by some endowments, uh, look, you're from the Draper family.

Why couldn't your dad, why are you $50 million? 

Jesse Draper: Everyone's like, oh, fund three. It's so easy to raise, like you have a track record, all this stuff. In a lot of ways I felt like that was true. We broke more institutions. I think what I talked about in the beginning, this like preconceived notion, one about where I came from and this judgment more than ever before.

And in some ways I thought, oh well maybe it's 'cause I'm getting to these ranks where like my dad has been or something, but like I still have to go through the processes. I've had someone at one of the large advisors say to me that exact thing, like, Hey, I don't understand. Why can't your dad just give you $50 million?

And I'm like, sorry, does your dad give you $50 million? Is that a thing that dads do? Like I just was not aware. I still have to go through the same processes. And you of all people should know that because you manage all of these LPs and funds like mine pitch you every day and I'm sitting here pitching you and you're just kind of being mean about it.

I mean, I've heard it all and like I think I've gotten much more comfortable speaking openly about it, but I'm proud of my family and I don't know why I shouldn't be. People are making me feel bad. My dad worked so hard. Mm-hmm. He worked so hard and he was like one of the first investors in Tesla and Baidu and all of these amazing companies, Hotmail and like.

I learned so much from him. I don't know why people wanna make you feel badly about that. Mm-hmm. And I watch friends like Patrick Schwarzenegger going through, you know, similar kind of avenues. And you see these kids though I think Patrick is like such a solid human being. He's also a great investor and a great actor.

And like you see these other generational kids, and I don't understand why people give them such a hard time. Like it's about what you do with it. And I don't think it necessarily gave me a leg up in the ways people expected it to. Mm. I think in some ways there's more judgment. 

SCS: And how have you risen to that?

I mean, I've heard you talk about how you've been very hard on yourself and you actually do the meditation of Jesse, I love you. Yeah.

How does this weigh on you? I mean, this is an important conversation though, so we're working with a lot of family offices. We know we're at the cusp. You know, we're going through it now.

The great wealth transfer, right? Yeah. Where women are inheriting and earning their potential. The next generation are coming into power, and there is that. Guilt too. Yeah. While they're trying to make an impact. Yeah. As a fourth generation venture capitalist, how do you come to your own, like what would you say to someone who's going through a similar journey and trying to make it work?

Jesse Draper: A lot of my friends who are kids of venture capitalists, like at Sequoia, other places, like didn't go into that business. I had a great conversation and she probably wouldn't even remember me now, but with Christie Hefner, Hugh Hefner's. Daughter. The first question out of the gate I asked her was, I said, how do you deal with being in the same business as your father?

Like, was that hard for you? And she is a force. She ran the company for many years and she is amazing. And she said it was easier to be in a different city than my father. But also if you can't take it, you shouldn't be in the same business as your father. I certainly can take it, and I have, and I think back then, I mean the articles written about me in my twenties.

Imagine being your most insecure self in your early twenties and having every tech gossip news rag. Yeah. Write about how everything you got was from your dad your entire life, and like that sticks with you your entire life. Mm. So it's like you can't really say anything to me at this point. That wouldn't hurt.

That would hurt me. Like, I'm like, yeah. Yeah. I get, I get it. You're gonna say something. Yeah. I think you just need to find your own power and stand in your own light and your own power. And I do something very different than my dad does. Yeah. And I also, again, I'm so proud of him. Yeah. Like I don't want people to make me feel like I shouldn't be. Yeah.

Not just girls. I've had a, I've had some amazing conversations with men about this too. For anyone who's trying to be seen in a family that is well known, just be authentic to yourself. I. It took me a long time to realize I needed to put kind of a bubble around myself and not be affected by any assumptions, and even like within my own family, people pushing me to do different things.

Mm. I found my thing. Yeah. I like doing my thing and I feel strongly that I wanted to solve childcare and I want to invest in women and create the next billion dollar women of the future. Absolutely. That's what I wanna do. And that has nothing to do with my family who I love. 

SCS: Full stop. And so where are we today?

I mean, it was not too long ago that you were Le Petit Hermitage going to this hotel at 9:30 PM 14 dudes, five bottles of wine in, and you're there at 9:30 PM. You wrote this article, what was it, four, five years ago? Investing in Women is not a Charity. Yeah. And now you've done the work, you've proven yourself, you've got some really good exits under your belt, and all of those investments.

Have we changed? Has the market moved forward to see investing in women as good business? And what else is missing here?

Jesse Draper: I don't think we've changed enough. I think that we need to make more change faster, and in order to do that, we need to keep women in the industry. We need to support, solve childcare so that women can stay in every industry, and that is something that we need more.

Women's involvement in. I also would say there are women who are stay at home moms. That doesn't mean you can't like dip your toe in and support female led businesses. If you know you are someone of high net worth, like write a check to a female founder, like you can just support them from afar and still manage your family. I just want more women leaning in overall.

I went to a conference last year. I was in the middle of raising this fund that I was mentioning, and I'd been talking to this big advisor who manages billions and billions of dollars of the world's capital, I would say the largest institutions in the world.

And working with them would unlock a lot of money for me. Mm-hmm. And he was hard to get ahold of. I kept texting him. I knew he was at the conference. I said, can I please like get in touch with you? I ended up bumping into him and I was like, hey, like, can I have 15 minutes? I just wanna give you an update.

And he's like, well, walk with me, and like, what do you need? And I was like, well, I just, he's like, no, I, I don't have enough time. You can meet me tonight or whatever. I'll text you the details. He text me, he says, you can meet me at 9:30 PM at Petite Hermitage in Beverly Hills.

I no longer drink at work events. I never really did. I don't like going to work events past 8:00 PM I actually leave at 8:00 PM because I think women understand this, but like men get a little sloppy and it's like not fun for me anymore. It's also why I wear heels and I'm already six foot tall, and so I'm like six foot four with heels because I'm just like, don't mess with me, don't flirt with me, like I'm married with kids and like I just am here to do business. And no good business gets done, like after a certain amount of wine.

So I was already pissed that I had to show up at 9:30 PM at a hotel on the rooftop. And I was also like, am I going into a hotel room? I mean, if I was like in my twenties and younger and hotter, like I'm sure I would've been more scared. I asked a few people, I said, is this weird? They're like, no, it sounds like, like he's a good guy. I was like, okay. So I show up.

There were like a whole bunch of men, male GPs, who had been having dinner. So they've clearly had like a 6:00 PM dinner. They're like 10 bottles of wine in, and I see all the bottles on the table, and also it's like one of those very low tables. And I'm wearing my heels, probably these same heels I'm wearing today. And so I'm like towering over this table. And they're all like, oh, hey, hey.

And I'm thinking, why the fuck, didn't he invite me to the dinner? Mm-hmm. Like this is unbelievable. Yeah. Is it because I'm a female and he only wanted men around the table, but this is just what we deal with. Yeah. And he got up, he was very kind and polite and like came over and he was just like, wow, it looks like I need to invest in some women.

Mm-hmm. And I was like. Yeah. Yeah, it does. And I was pissed. Usually I'm like, sweet as pie. I was just like, yeah, you do. Then this guy gets up and he's like, oh, hi Jesse, and this is this GP that I just, he's not my favorite, and he is like. Kind of a schemer, I guess I would say. And he's like, oh, are you thinking of investing in Jesse?

And then I was like, yeah, actually his only two good deals I sent to him and they're now billion dollar companies. Like I felt like I had to really prove myself because I had not been part of the dinner. I had not been there like schmoozing with everybody. And it's like I can go to the dinner and have fun and I don't have to drink, but like I can still have fun, participate in the conversation.

I'm trying to get this guy's ear just like the rest of these guys. By the way, my fund's doing better than a lot of them and I was so mad. And this is last year! Yeah, this is now. I mean, the worst story I have was pretty recent, so I was mentioning that fund three was so incredibly hard to raise and it was because like, I can't really believe it, but it was a lot because of this family thing like my dad being an incredible venture capitalist and my grandfather being an incredible venture capitalist, like I just started getting a lot more pestering and I don't think my brothers get that at all when they raise a fund.

So I had been talking to this with my whole team. I'd been talking to this institution that's associated with the government for nine months, which is probably typical for an institution that you're trying to close and we were there, they had called, so you had to have 25 references for each person: 25 references for me, 25 references for my partners. It was like 5 LPs, 5 portfolio companies, 5 all these things.

So we have all these references. They've called all our references. They have done all the diligence they could, and the guy who's been part of this process seeing it through, he basically said, I'd love to hop on a quick casual call with you.

We're like, okay, cool. Maybe we're there. This is so exciting. He hops on the phone and he says, so. You're there. You are on the fence. I wanna get you over the fence. You're doing so great. We called all your references. Your CEOs speak so highly of you. Everything's super positive. Right? Okay. He's like, but in order to get over the fence, we were thinking that maybe you could like nestle your fund under your dad's fund.

Ooh. Or an older, gray-haired male VC and make them a partner. And I'm sitting there being like, wait, we just did nine months of work on this and this is my third fund. It's not my first. And then I have to sit there and be polite and make myself small 'cause I'm a woman. And I, I don't wanna mess with the opportunity 'cause my team's sitting there and like, I don't wanna ruin the opportunity for us.

But I am so mad again, like, I'm like, what the heck? You know? Yeah. And I sit there, I have like steam coming outta my ears and I'm asking clarifying questions like, Hey, like, we have this incredible mentor like Dana Settle from GreyCroft, like you know, she's already a mentor of mine.

Or what about Sonja Perkins? Could I make her an advisor? And I'm asking about women specifically. 'cause I wanted to clarify what he was saying. 

SCS: What is it, that he wanted . 

Jesse Draper: And he was like, no, we really think that it would be better if you did this. I'm like, okay. So this is like, are you trying to tie it to my dad? Are you trying to tie it to a man?

But like, anyway, we ultimately ended the meeting. Mm-hmm. We were very kind and I pr-, I pretended nothing was bothering me. Shut the computer. And my partner and I look at each other and I'm just like, I am so livid. Yeah. And so is she. So we write an email and we aren't thinking we're gonna send it. We're sort of like, let's just write an email and see if something comes out. I don't know. Yeah.

We decide like we could copy every single person at this organization basically, documenting as you should, you know, what happened on that call. Because I was like, I don't know if I'm mad about the sexism or the nepotism like assumptions or the like, I don't know what, it's just so wrong.

'cause I did the work. You're telling me my track records stellar, like you're telling me all these things. And so we write this letter and we say, Hey, here's what happened. Thank you for all the kind things you said about our fund. And then at the end we said, we are discontinuing with your process because we were not aware of the older gray haired male requirement that the SBA of the United States government required, so this was the Small Business Association's SBIC program. And it was like maybe one of the more horrifying things that I've ever 

SCS: Yeah. Experienced. 

Jesse Draper: Experienced. And I was just like, this is unprofessional. And this is the United States government. Yeah. And like this is so messed up.

And so we quickly got a call from all of them. They tried to get us back. They were like, let's you know we need to push this through. I asked him like, they had this new woman come in, they asked him what happened. He basically said so much worse than we actually relayed in the email. So they were horrified.

And since then we've had an administration change. And this woman has quit. That's where we are as women right now. 

SCS: Challenges continue to persist. What needs to change? 

Jesse Draper: Everyone invest in women, like everyone needs to make sure there's a female on the team in the boardroom. It doesn't have to be financial.

It could be like you're advising a woman and you can be a man in advising a woman. You can be like, just make sure that you have equal representation. Also, if you, you know, it seems like you are speaking a lot to family offices. Make sure that women are in the room when you're making the for-profit investment decisions.

Mm-hmm. Make sure that you're educating them just as much as you're educating your sons. We're having the largest transference of generational wealth right now is going to primarily women. We need to make sure that we support that. I'm hoping that the pay gap changes because of that as well. 

SCS: And what is the vision for Jesse Draper in the future?

What is the end game here for you? 

Jesse Draper: We will go raise fund four very, very soon, I'm sure. And we're really excited. We hope to eventually manage a billion dollars for women with many, many unicorns in there. We already have five. Yeah. And so. Keep watching Halogen Ventures. 

SCS: Yeah. Awesome. Okay, and to wrap up here, we play a bit of a card game. Pick three.

Jesse Draper: What is one piece of advice you'd give your younger self? I'd give my younger self a really big hug, and I would say it's gonna be okay and. Stay confident. 

SCS: Love it. Next.

Jesse Draper: What's one thing you wish you knew earlier about wealth or investing? Hmm. I wish I knew how cool Robinhood was. I mean, I don't wanna be an ad for Robinhood or Acorns or any of those, but it's so cool.

You buy a stock in 10 seconds, less two seconds. You can be like, oh, Nvidia sounds cool, and then you just swipe and you like, own Nvidia. I wish I knew how easy investing in the stock market could be.

SCS: And everyone can do that. Yeah. In a small way. All right. Let's just take one final one. 

Jesse Draper: What habit sharpens your emotional intelligence?

Oh, having deep, thoughtful conversations. With my founders, my friends, and my family. I think having going there, mm-hmm. Make sure you go there. Make sure you go to those uncomfortable spots. That really helps with your emotional intelligence. 

SCS: Well, Jesse, thank you for going to many uncomfortable spots emotionally today.

Jesse Draper: So many, so many. 

SCS: Well, that's all of you. And thank you for standing in your life, standing in your power and leveraging the platform that you've built over the years to shine a spotlight on women that are driving business. And we all know through you, again and again that investing in women like you is good business.

So thank you so much for your version of billion dollar moves. 

Jesse Draper: Thank you, Sarah.

SCS: You survived.

Jesse Draper: Thank you, Sarah.