Girl Friday: Jesse Draper
Photography by: Lindsey Freitas
Jesse Draper has built the business empire, Valley Girl Inc., by talking about, well, business. A refreshing twist on typical number-crunching suit shows, her syndicated web talk program, The Valley Girl Show, can be accurately described as “The Ellen DeGeneres Show for business.” A typical day on the set of The Valley Girl Show may involve pink umbrellas, boas, or pom-poms, in addition to any number of silly parlor games for the unsuspecting Silicon Valley entrepreneur. Dovetailing on the success of her show, Jesse has started a networking organization for women in business, revealing her soft spot for helping women navigate the stereotypically masculine working world. I’m sure I am not the first person to be bowled over by Jesse’s unpretentious idealism. She radiates the kind of inspiration that sticks with you, so much so, that you can’t help but want to change the world, too. The Valley Girl Show is syndicated on various news sites like Mashable.com and can be seen on screens across the U.S., but for the really tech savvy, it is also available as an app on Androids and on the iOS family.
Tell us a little bit about your childhood and your path leading you to where you are today.
I always wanted to be an actress, ever since I could remember. I grew up in Silicon Valley around entrepreneurs and technology and although I didn’t study business, I knew the startup industry better than most because I was raised in the middle of it.
He took me to amazing places like the Ukraine where I met President Uschenko, and to the very first Skype board meeting in Estonia
My Dad was very hands-on with my siblings and me. He often took me on business trips with him to learn and observe. He took me to amazing places like the Ukraine where I met President Uschenko, and to the very first Skype board meeting in Estonia. Because of him, I got a different kind of business degree. He is a Venture Capitalist, which means he invests in startup companies that need help getting off the ground, so I would usually see the latest technologies before anyone else did.
After college, I was on a Nickelodeon show called The Naked Brother’s Band for a while. It was an incredible experience, but I realized that although I loved acting, and still do, I didn’t like the audition process. It wasn’t for me. I would wait for hours in a room of identical girls who were all probably just as talented as I was to audition for 30 seconds. I always felt like I could do more with that time.
I would see entrepreneurs I knew on CNN or CNBC being grilled in interviews and I thought, these are some of the smartest and most inspiring people in the world, why isn’t there a more positive and fun talk show, (that I would want to watch), for them? That’s when I started The Valley Girl Show. I started it essentially in my parents’ garage. I had my brothers film my first shows and really had no idea what I was doing.
Every year since, I’ve learned a little more about running a show. When you build something, you are always trying to improve it. I have filmed 120 interviews thus far and I don’t know if I will ever be satisfied. I believe the need for improvement is what keeps me creating.
I have since studied some business, but I am also running one, so when I get a breather, maybe I’ll get my MBA. Or maybe I won’t need to.
I love how you reclaimed the phrase “Valley Girl.” What’s the story behind the name and concept of your web show?
The Valley Girl Show title originally came from my brother Billy. We were toying with the idea of calling it Silicon Valley Girl, but my brother said, “Just call it ‘Valley Girl’!” So we did and it actually brought on a persona all on its own. Since a ‘valley girl’ was a 1980’s ditzy San Fernando Valley persona, we decided to embody a piece of that. Valley girls like to wear pink, so the title was really the introduction to the pink world we have created. I often joke with people and tell them, “If you are going to brand yourself with one color, be very careful with the one you choose because you could be wearing a lot of it!” I could now clothe anyone in sports to eveningwear in pink! Pink has been a really positive color for us! It’s surprised me a lot. I visit offices or speak at business conferences around the world and people will wear pink for me. It’s not the color you typically see in the business world. To me, the color means, ‘we are going to talk business and we are going to have a lot of fun while doing it’. It adds a little spice to the business life.
You come from a family of entrepreneurs, was that intimidating or inspiring?
Inspiring. Definitely. I am a fourth generation entrepreneur, and am the first female to become one in this line. My great grandfather, grandfather and father all started their own Venture Capital firms. My Dad raised all my siblings and me to look at everything as business, so that is what I have tried to do in life.
I went into a completely different field than any of them, so I really didn’t know what I was doing, and frankly, neither did they. I have the most supportive family in the world. My Dad is my number one fan and was the one who encouraged me to start the show in the first place. He said, “Just do it!” On the other hand, I didn’t know many people in media and had to figure out how it all worked. They definitely inspired me to be an entrepreneur by raising me to look at the world through a lens of opportunity; I never felt like I needed to take the normal path; I felt like I could do anything I dreamed up… Apparently that was a very pink business talk show.
Silicon Valley seems like a boys’ club. Do you find it difficult to be taken seriously as a woman?
Let me start by saying there are definitely not enough women in technology, or business for that matter, and I often find myself at events where I am the only woman in a room of 60 men. This alone is intimidating. When I started The Valley Girl Show, it was definitely hard to be taken seriously. Not only was I a girl, but I was interviewing these huge executives and wearing a ridiculous amount of pink while doing it. Over time, people have begun taking me more seriously, and some of the same people who were once skeptical are now pitching me guests for the show.
I think that many high-powered women feel like they had to fight and claw their way to the top. They’re afraid to put themselves out there and talk about the fact that they’re women, that they have a family, because they feel like they can only stay at the top by exuding a certain hardened and, ironically, more male persona. The joke is, we are women! Women in business should be able to act like themselves and have a ‘girlfriend’ side. When I do attend these mainly male conferences and events, I make an effort to get to know the few women I do see there. I always go up to any female I see and say “Hi!”
With your job you are often privy to the bleeding edge of technology. What are you excited about in technology today?
Every season of the show, I notice new patterns in technology. A few years ago it was Cleantech and social media. This year, I’m seeing a lot of new e-commerce models and big data companies, and the media business is still changing. No one has quite mastered the digital media model yet. I think there is still much yet to come in the media industry.
One company, (not necessarily in those categories that I am really excited about), about is TaskRabbit, where you can find someone to do anything for you, from a personal assistant to someone to sew a skirt. The best part is [that] you can hire them for as many hours as you want for a decent price, determined by you. They also do a background check, so you know you aren’t inviting a serial killer into your home. I’m obsessed! It’s really saved my life recently because I haven’t had much time lately to run errands, etc.
My favorite app right now is Evernote. It’s like a file system for your brain!
What do you consider to be your life’s passion?
I was put on this Earth to encourage women in the workplace.
How would you describe your style? What role does fashion play in your life?
I love fashion. On the show, we have actually re-evaluated my wardrobe this year and taken it from ‘girly pink’ to ‘pinkified business-savvy.’ I now sport pink blazers and pink pencil skirts.
I also strongly believe that if you travel with one black dress and a swimsuit wherever you go, you can pretty much get through the day in any city.
For my off-camera style, I love Trina Turk and DVF dresses and I like wearing heels that are way too tall, even thought I am almost 6 feet without them. When I am just hanging out, I’m definitely a jeans and tee-shirt kind of girl; I love Gibson fitted blazers and I have too many of them. If you catch me working from home one day though, I guarantee I will be in some sort of sweats, probably lululemon. I also strongly believe that if you travel with one black dress and a swimsuit wherever you go, you can pretty much get through the day in any city. I am walking proof of this concept.
What stores are your sure-fire bets for women working in an office? Do you have a go-to outfit?
For women working in the office, I am a huge supporter of a great black dress. I typically hit up Bloomingdales and Banana Republic when I’m looking for new office wear. I also love wearing a nice colored scarf or accessory of some type when I’m wearing all black.
My go-to outfit would be my black fitted sleeveless DVF dress, (which has had a little too much wear), with a black, white or pink blazer, pumps, a scarf and ballet flats in my purse. (Always.) I also wear very simple jewelry. I love simple pearl earrings and layered pearl necklaces and I’ll dress up the outfit with those sometimes. Cristina V is one of my favorite jewelry designers.
What do you consider to be your hardest won or most treasured life lesson?
Around 5 AM, I opened my eyes to find a man in my room. I didn’t know him. He was a complete stranger.
I’m gonna go with ‘hardest won’ for this. Because women will be reading this, I’m going to potentially over-share, because I think this is important and I’m happy if I can help one female by sharing this story. This was a lesson I learned that changed my life dramatically. This is something I’m not super comfortable talking about in person, but somehow, I feel like I can write it as enough time has now passed.
The day I graduated from UCLA was one of the happiest days of my life. I walked in the ceremony, celebrated with my family and friends and literally felt like I could do anything. I have never been so happy nor been so ready for life! I was on top of the world! That evening I went to bed ecstatic.
I survived because I fought back and I screamed with a voice I didn’t even know was inside of me.
Around 5 AM, I opened my eyes to find a man in my room. I didn’t know him. He was a complete stranger. Without getting into the details, he essentially beat the living crap out of me. The lesson here is I survived because I fought back, and I screamed with a voice I didn’t even know was inside of me. Over and over I asked myself, “What did I do? Why did this happen to me? Was I too happy on my graduation day? Am I being punished?” It took me a long time to learn this lesson and to even be able to talk about it, but after a good amount of therapy and a lot of being afraid of life, I found myself again. I now look at this experience in the most positive way I can, as something that literally kicked me into the real world. I had grown up fairly sheltered and not afraid of anything and, in a way, this brought me into reality.
The three lessons I learned through this experience as a female:
- Fight back! In a situation such as this, most women, (and men), freeze up. Take a self-defense class! And, I pray you don’t, but if you ever find yourself in a situation such as this and haven’t taken a class, don’t let this stop you. Fight back anyway! It could save your life.
- Eliminate the risk. Women in general are way too nice. I was raised to say, “Yes!” all the time and to be nice to everyone, even a stranger. I now say a very strong, “No!” every once in a while. When I’m walking alone on the street at night and there’s someone walking behind me that I’m a little nervous about, I follow my intuition and simply cross the street. I eliminate the risk.
- We are resilient. Sometimes it takes a little while, but you can come back from almost anything. When you hit a low point, keep going. You will get through it; time heals all.
What are you most enjoying learning about yourself lately?
I feel like I am always learning something new about myself. Every year when I look back on the past year, I wonder how I could have been so naïve in this situation or that. This year, some of the lessons I’ve learned are:
- I am not a wedding planner.
- Balance in your life takes practice.
- I have no idea where my ‘reading’ time went, but I no longer seem to have time to read books and I need to find it.
- Sometimes I need to unplug.
- I need to take weekends to recharge, and occasionally that means a ‘stay-cation’–meaning no one knows I am in town except my fiancé.
Congratulations on getting engaged! Has that changed you, now that you’re thinking about your future with another person?
Thank you. And yes, I think it has changed me. I am sooo in love with my incredible man!!! It has reconfirmed my relationship in a way I didn’t understand until I got engaged. I really had no idea he was going to propose, but I couldn’t be happier! The one decision as of late that has been a difficult one is whether or not I am going to change my name. As I am a woman in business and a bit of a feminist, I have come to the decision that I am not going to. ‘If he gives up his identity, I will give up mine’ was the decision we came to together. Oddly, he didn’t want to change his name either.
Do you plan to have kids in the future? How do you think you will balance your home life with your career?
I definitely plan to have kids in the future. I recently hosted a women’s networking event with Alexis Maybank, one of the founders of Gilt Groupe who said, “There is no perfect time to start a family,” and
There is never a perfect time. If you’re a working woman, I encourage you to continue working and just assume you will figure out how to handle it all when life happens.
I think that is true about every other thing in your life. There is never a perfect time. If you’re a working woman, I encourage you to continue working and just assume you will figure out how to handle it all when life happens. I’m a little nervous about it because I want to be a hands-on mom. I find comfort in the fact that many other working women, (and men), have learned how to prioritize their family. Sheryl Sandberg, the COO of Facebook, leaves work every day at 5:30 PM to have dinner with her kids. Joan Gillman, president of Time Warner Cable Media says she turns work off the moment she gets home and puts her phone in another room. I do believe [women] can have it all. We just have to figure out what works for us, and when to prioritize family over work. My mom was the most incredible hands-on mother in the world, (and still is), and I aspire to be a great mom just like her!
What advice do you have for younger women who may be following in your footsteps?
So many things!
- Go after it! Whatever you want, just go for it. Know what your goal is and don’t stop until you get there.
- Put it out there! You need to let people know what you want. That means, if you want a talk show, you need to tell people! You’ll be surprised by what comes back to you if you simply ‘put it out there.’ How will anyone know how to help if you keep your dream a secret?
- My Dad always said, “80% of success is just showing up.” That has been truer this year for me than ever before. Attend! And if you can’t, RSVP promptly.
How do you see your future?
And if nothing else, I hope I am happy and have time to read Archie comics and relax every once in a while.
5-10 years down the road, I’ll host a talk show like Ellen DeGeneres, my hero, (or Oprah, or Stephen Colbert, or Jon Stewart), but with a strong focus on business and technology (and fun!). I’ll have a family with a whole bunch of kids, hopefully 3-4 or more. My husband still loves me. I’ll somehow regularly support women in business and women in the workplace. And if nothing else, I hope I am happy and have time to read Archie comics and relax every once in a while.
Girl Friday is a phrase more common to the 1940s and 50s, defined as “a female employee who has a wide range of duties,” and is most recognizable from the film His Girl Friday. Here at Move LifeStyle, we’re resurrecting its saucy vibe for the title of our last column of the week which profiles inspiring women in the workforce. If you like this series, click here for more Girl Friday Interviews.