DEO Profile: Jesse Ziff Cool

Entrepreneur and author

Maria Giudice & Christopher Ireland
Rise of the DEO
8 min readJul 3, 2019

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Jesse smiles as though she’s shy. At heart, she may be, but in practice she’s an extroverted DEO who has greeted and fed thousands of customers, including Oprah Winfrey, Steve Jobs, and Bill Gates. The creative force behind five unique restaurants and seven cookbooks, she’s dedicated herself to sustainable agriculture and cuisine for over thirty-five years.

We interviewed Cool at her home in Palo Alto, California, after a tour of her vegetable garden, fruit trees, and chicken coop. Sitting in her large and highly functional yet comfortable kitchen, she explained how her career and her life grew out of her passion for good food.

Did any early experiences influence who you are today?

My father was in the grocery business and I had an uncle who was a butcher. Growing up in a Jewish-Italian family meant food was everywhere. As a little girl, I’d go to the refrigerator and make lists of ingredients. Then I’d take those lists to my family and ask what they wanted to eat. My brothers loved it. I’d drag out tables and chairs and make little restaurants outside for everyone. I’d make places for them to sit and eat. There’s so much love and connection that comes from food. When you feed people, you can feel that connection. It’s nurturing.

Do you think of yourself as creative?

Yes, my medium is food. Whenever I’ve needed to take care of myself, my inspiration has always been through food. With it, I’ve created deliciousness and political connection with the environment, and connection with my staff.

I feel creative on many levels. I think of gardening as creative. I connect to my plants, the dirt, my chickens. I also love to cook. My happiest moments are cranking up the music, having something to drink, and cooking for hours.

How do you recognize creativity in others?

I look to see if they have a connection to whatever drives their passion first. If someone is a potter, he should be able to feel the clay. If someone is sensual — if they use sight, hearing, taste, feeling to connect — they’ll find a way to be creative through that connection. It will bring forth an idea, a manifestation of beauty or something deliciously wonderful.

For cooking, it’s similar. I look to see if they understand the ingredients. If they have a sensual connection with the ingredients, then creativity will bound and grow from that connection. Of course they have to have skills — they have to understand how to use salt, sugar, fats, acids, the basic palette. An artistic appreciation and connection flows beyond that understanding.

When I see that someone has a real sensitivity to subtle flavors and doesn’t try to trick the eater with flavors, that’s a good sign. I look for someone who connects to the source of the food, who starts with ingredients — how they’re grown, treated, nurtured, loved. A creative cook will start with a connection to the basic ingredient and then add the right things or do the right things to enhance it.

Do you think of yourself as a good businessperson?

No, I struggled to learn how to be in business. What I know about business came from the old-fashioned ethic of working hard and serving the community, but I didn’t really understand how to run a business. At my first restaurant, Late for the Train, I did everything. I hand-printed every menu, I went to the market, and I cooked the food. I didn’t really think of it as a business. It was more a natural exchange of services.

But I’ve always been really good at counting things. I was taught to have integrity, so I thought of myself as a “waste manager.” I intuitively kept costs down because I found waste disgraceful. I think that’s what kept me afloat when I didn’t know anything about business.

When the economy fell apart in the early 2000s, I was maxed out on everything. An advisor said I should declare bankruptcy, but I couldn’t imagine not paying people back. Instead I started working with advisors and learned the really difficult foreign language called QuickBooks. My advisor taught me to hire people who are different from me. I learned how to be a woman in the business world; instead of giving everything away, I could save money and reach my goal. Now I get it.

Have you made any course corrections in your career?

Most of the time I had no clue what I was going to do next. I just kept doing what seemed right. One day I was sitting with a friend and he introduced me, saying, “Here’s Jesse. She’s an author.” I said, “I’m not author! I’m a restaurant owner.” That was an epiphany. I thought I’d been going around trying to run my business and get publicity, and as part of that I’d written four books.

The epiphany was realizing that I was a restaurant owner and also had become a writer!

Did you overcome any hurdles in building your business?

I’ve been near bankruptcy more times than I’d like to admit. But I was always willing to go out the door and quit rather than not use organic, local produce. So I knew I cared about that principle and I would not change it. I had to learn to design the business around that core belief. Fortunately, the world changed. Now people agree that there should be a connection between food and local growers, so the business is prospering.

Women traditionally didn’t belong in the food industry. This made me stronger and tougher. Women in food can’t have a period. They can’t talk. Can’t cry. Can’t complain. This challenge taught me how to build a business structure that’s also good for people. Our community taught me about the value of longevity. They trust me. I get so much help from everyone. I’m so particular that I used to want to do it all myself. It was really hard to learn to let go of some things.

What’s your leadership style now?

My philosophy at work is “the customer comes last.” By that I mean that if I take good care of my staff, then they’ll take good care of everything else. So I manage from the bottom up. I’m a support for others to get things done. But I also have really high standards. I’m particular and detailed, which some describe as “picky bitch.” I work hard so I expect everyone to work hard. I hope that everyone collaborates, shares ideas, and helps each other to collectively create change. It is also important to balance the old and the new. There is a lovely connection in balancing tradition and innovation that can bring stability and newness.

Is corporate culture important to your business?

On a scale of 1 to 10, it’s a 10. People work hard. They should feel proud of their work. I want them to feel that they’re in the best place they could
be. They eat better, they get the best money, and they’re given responsibility for their team. I have a core philosophy based on the connection of food to the farm — my coworkers have to be able to tell this story. I want them to be themselves and yet a part of our story as long as possible, so we all keep evolving and changing.

We live in a privileged community and sometimes this intrudes on our values, but we try to ignore it. We’re really doing well right now and it’s easy to get the wrong attitude. I keep reminding everyone that we’re here to serve and care for people. Some people ask a lot, but we remind our staff that their job is to care for people.

Do you create this culture or does it just happen?

Both. We do things to attract the best talent. For instance, the primary reason I grew my business was so I could get better benefits for my employees. Because of our employee policy, we attract people who may not have experience, but we can usually help them learn to care for clients. If they can’t — if they’re needy themselves or just want to be nurtured without passing it on — then we bounce them out really fast. If they think they’re going to be taken care of, without giving to the community, they’re gone.

Though we have natural turnover in our business, the culture is much more family-like. We have had people working with us for a very long time … 5, 10, even 18 years! It means that I am a part of it all, but they actually are just as important to the company culture. I believe they know they are a part of our identity.

When did you first realize you could lead others?

In fourth grade, my mother got called in to the school and they told her I was bossy. I wanted to be the teacher. I’d rather rename bossy to “can direct.” I saw things in a way others didn’t and I wanted to manage people. I wanted things to be different. I didn’t fit in until I moved to California.

Jesse visits her backyard chicken coop, a place where poultry and sculpture live in harmony.

How do you deal with risk?

I’m a radical conservative. I’m calculating about the risks I take. I was taught as a child to go as far as you can toward danger, but when you see danger, you stop. I do that. I jump into new ventures and figure out how it works later. I take something on because of an idea … to change and create something new and exciting for me and the businesses. Most often, it starts with a location that is cool or has a reasonable lease. Then I think about the food or a menu before any thought of viability.

I am not afraid to risk. At this point, after so many starts that needed major adjustments, I know that when something doesn’t work, we’ll just keep changing until we find ways to make it work. For some that is risky. For me and my staff, that is just being realistic.

My employees trust me. They trust that together we will figure things out because we always do. I have often said that the best lessons are from watching someone else’s challenges or mistakes and how they fixed them. We all learn this way. That internal business risk, though it might seem costly, is far less costly than not taking any risk at all.

When you’re gone from the scene, what three things do you want to be known for?

One, for truly living the full cycle of sustainability in all aspects of my life and business. Two, for being a lot of fun, for being up for play and adventure at any age. And three, for being both soft and strong: that my children knew they were so loved and that I lived a meaningful, fabulous adventure full of martinis, great food, and a love of life.

To read the next DEO profile go here. The next section in this series is here. To start at the beginning, go here.

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