Although my brother and I are close and we see each other often, I was still excited to have him participate in my monthly, Conversations with Hilary. I was even more excited when his wife, Jennifer, agreed to be part of the monthly series – a two for one. I am biased, but I happen to think my brother and Jennifer are pretty terrific – individually and as a couple. My brother, the founder of PlumpJack, who has also worked his way up in California politics from a commissioner, to supervisor and then Mayor of San Francisco, to now Lieutenant Governor of California and candidate for Governor in 2018. Jennifer is an award-winning filmmaker and CEO of The Representation Project. This highly accomplished pair is expecting their fourth child in the winter, and my two nieces and nephew are just thrilled to have a baby sibling on the way!
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Despite all of their professional commitments, they spend a lot of time together riding bikes, swimming, traveling, enjoying the outdoors and eating pizza with their Grandpapapapa.
I hope you enjoy this Conversations with Hilary as much as I did!
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What do you believe to be your greatest accomplishment?
Our three kids – and we’ll let you know about the fourth after we meet him.
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Do you have a prized possession?
Gavin’s Leica camera. And the horse Jen doesn’t have yet!
With our father
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What qualities do you think others love about you?
Our courage in the face of adversity. Our commitment to social justice. And, our ability to laugh at ourselves.
If you could do anything other than what you currently do, what would it be?
We’d run a wildlife refuge, Safari outfit in Botswana.
What do you like most about what you do for a living/career?
Creating the right conditions that help people overcome life’s obstacles, and achieve their aspirations. Righting social and cultural injustices. Making a difference.
What’s the first thing you do when you wake up?
Gavin grabs his cell phone. Jen runs to a crying child.
What’s your favorite thing to do on a Friday night?
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What were you passionate about in your younger years growing up?
Sports. Nature. Travel. Exploring.
What are you passionate about now?
Making a difference. Raising our kids to be whole, healthy human beings, not limited by stereotypes. Ensuring future generations have agency and are not bystanders in the world.
What’s your favorite season and why?
Summer because everything slows down and we get to spend more time with family and friends.
If you were stuck on a deserted island, what three items would you want to have with you?
A wifi router, electricity generator, and an iPhone so we could FaceTime the kids.
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What’s the #1 most played song on your iPod?
My little Pony’s “Art of the Dress” – From Songs of Friendship. What can we say? Three kids.
If you could have lunch with anyone, living or dead, who would it be? Jennifer: Eleanor Roosevelt, Sargeant Shriver, and Mahatma Ghandi
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If your life was made into a movie, what would it be called?
“I’m Really Busy, Please Leave a Message”
Do you have any regrets?
Don’t we all? But if it doesn’t kill you, it only makes you stronger, deeper, and possibly more interesting.
The first time I met Jennifer
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Freedom means the ability to choose and pursue your destiny.
What are your personal core values?
Hard work, courage, authenticity, kindness, compassion, speaking the truth.