THE FINE LINE | with Jesse Draper
The Fine Line | with JESSE DRAPER
Balancing career and motherhood is no small feat, but for Jesse Draper, it has been a catalyst for transformation. As the founding partner of Halogen Ventures, a Los Angeles-based venture capital firm backing early-stage companies with female founders, she has redefined how she approaches time, investments, and leadership — applying the same strategic mindset to parenting as she does to venture capital.
The first solo female General Partner in Los Angeles, Jesse is a fierce advocate for investing in women, believing it’s the key to solving critical issues like healthcare, childcare, climate, and education. Her portfolio includes over 70 game-changing companies, such as theSkimm, Babylist, ThirdLove, HopSkipDrive, and The Flex Company. Her viral Medium piece, Investing in Women Isn’t a Charity, sparked industry-wide conversation, and she’s been recognized as one of Business Insider’s ‘Top 10 Early-Stage Female Investors’ and Marie Claire’s ‘50 Most Connected Women in America.’ Beyond investing, Jesse is an Emmy-nominated host, a Board Member of various companies, and actively champions diversity in venture capital and entrepreneurship.
In this conversation of The Fine Line, Jesse shares how motherhood has sharpened her focus, the importance of investing in the future of family, and the rituals that keep her connected to her three sons amidst a demanding career. From embracing efficiency and letting go of perfection to ensuring her kids see her passion for work, she offers a powerful perspective on navigating ambition and family. She also highlights inspiring women-led companies reshaping industries — proving that investing in women isn’t just the right thing to do, it’s the smartest investment you can make.
How has becoming a mother positively influenced your career?
I’m more efficient. Before I became a mom, I took every single meeting.
Now, I am much more thoughtful about what is worth my time, what will move the needle forward for me, and what I should be spending my time on. I also know that sometimes you have to cancel something to do pickup for the kids — and that is ok.
I also invest in a thesis I have created called ‘Future of Family’ because I realized what a massive opportunity childcare is ($548 billion) to invest in, and no one else was seeing it. We now invest around how to support the family — from their physical health to their financial health — and it’s going really well. We have incredible companies like our billion dollar company Babylist, childcare company Upwards, and adoption technology platform Binti, to name a few.
How do you stay connected with your family while managing a busy career leading Halogen Ventures?
The early mornings are important to me. We are all up by 6:30AM. I spend time with my three sons each morning, cooking breakfast and getting them ready for school. My oldest son is nine and getting really into cooking, so it’s been fun to prepare more gourmet breakfasts with him lately. The three of them love to goof around, listen to music (we are currently into Benson Boone), and get ready for the day together.
I try to do dropoff as often as I can. And I also have zero childcare on the weekends.
I like to be all-in on the weekends with my kids, so they know that the week is for work and school — and the weekend is for fun and anything they want to do with us. We do a silly celebratory weekend dance on Fridays after school to kick that off.
What advice do you have for working moms?
Give yourself a break. Some days you won't clean the house.
If you hire a babysitter or a nanny, tell them exactly what you want done every day. If you aren’t a great communicator, write a list that you can keep adding to.
I find that very capable moms often think it will be easier if they just do it all. But the truth is, there isn’t enough time — and it’s not mentally healthy — to do it all. Make sure you offload what you can to help yourself, and your husband as well.
Processes also help me. I make lunches the night before, put them in the fridge, take them out in the morning… that type of thing. Maximize processes and any help you can afford to take things off your plate. (Also, make sure you teach and help your kids make their own lunches as soon as they can. Teaching them how to do the dishes and take out the trash doesn’t hurt either!)
How do you involve your children in understanding your work, and what do you hope they learn from watching your career?
Someone gave me the piece of advice to be excited when you go to work and make sure your kids see that. You can even say to them, “I’m going to work, and I am excited — just like you are excited to go to school today.”
I’ve learned that if you are visibly dreading going to work, kids will pick up on that and then it will be harder for you to leave them, them to leave you, etc. If you are excited and explain why you are excited to them, then they will be excited for you.
Also, it’s always chaos when I leave. But I have this mental shift that I call ‘shutting the door,’ which helps greatly. Once I leave my house, I shut the door and I leave the ‘mom’ version of me at home. I use that mental shift to let go of any guilt, and switch gears. If I’m stressed, overwhelmed, or can’t bear to turn my mom brain off, I simply tell myself, “Shut the door.”
Who are a few women founders and/or women-owned businesses that you're excited about?
FOLLOW ALONG
Follow Jesse at @jessecdraper and @halogenvc.
Follow Brigade Events and stay tuned for the next iteration of The Fine Line at @brigadeevents.
We’d be honored to include you — or a woman you admire — in this series. If you or someone you know has a story to share, we’d love to hear from you. Reach out to us at carly@ingoodcompanypr.com. Together, we can uplift, support, and redefine leadership for the next generation.
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