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Women Of The C-Suite: “Have bold humility”, With Sheryl O’Loughlin, CEO of REBBL

Have bold humility. To be bold is to step into the unknown with true curiosity and quiet strength, to proudly say “I’m here and I matter”…


Have bold humility. To be bold is to step into the unknown with true curiosity and quiet strength, to proudly say “I’m here and I matter” and, at the same time, approach the world as a student with a desire to always learn and improve. Holding this tension of bold humility is so important as a leader during times of confusion or chaos — being able to have compassion for others and know when to ask for help, to understand your own power and recognize where you need others to lift you up, to have both an explorer’s and a beginner’s mindset.


I had the pleasure to interview Sheryl O’Loughlin. As a child, Sheryl was best known for rushing everywhere and being too impatient to pour milk into a glass before drinking it. As an adult, Sheryl is no less eager. She served as the CEO of Clif Bar, where she introduced the world to Luna bars; she was the cofounder and CEO of Plum Organics; and she is currently CEO of REBBL super herb beverages. One of her favorite roles was mentoring budding entrepreneurs when she was the executive director at the Center for Entrepreneurial Studies at the Stanford Graduate School of Business. 

Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

In high school, I was interested in psychology because I wanted to help people. When my single mom told me that she couldn’t pay for college anymore, I decided that in order to secure my financial future, I would go into business and study the mind through marketing instead of psychology. I felt like a sellout but was terrified of running out of money. I started working at major food brands because I wanted to learn how to be a great marketer and, at that time, those companies were the ideal place to learn not just marketing but how to run a business. This eventually led me to become the CEO of Clif Bar & Company, where I was exposed to a business model that used the power of business to improve the lives of people and the planet. Realizing that business and making a positive difference in the world weren’t mutually exclusive, that you can work for social and environmental justice and pay the bills, changed everything.

After ten years, I yearned to start my own company, one that would uphold this higher purpose for business. This led me to be the cofounder and CEO of Plum Organics, a business dedicated to nurturing kids from the high chair to the lunch box. While riding the highs and lows of Plum, my husband, Patrick, who is also an entrepreneur, had the idea of opening an indoor play space where families could be active and get healthy food. We ended up financing the venture ourselves and, long story short, it failed in a big way. Between this devastation, starting Plum from the ground up, and figuring out how to claw our way back to financial health, I was so blinded with stress I could barely see my hand in front of my face. After that, I was sure I never wanted to be an entrepreneur or CEO again.

That is, until REBBL came along. I starting serving on the board at REBBL, and the more I drank those exquisite plant-based beverages and learned about the company, the more excited I became. I saw in REBBL the magic of the other great brands I worked for — a phenomenal product, a passionate team with grit, and a purpose that was the company’s guiding light. I remembered how much I love the food industry, how it’s so creative and real, and how I liked being part of something that, at the end of the day, I can touch and feel and see on the shelves, that my friends and family can enjoy. The joy I’d felt about working for a company that was dedicated to making a difference returned to my life.When the board asked me to become CEO in 2015, I agreed on an interim basis just to help through fundraising. But, then, I fell so passionately in love and here I am today, having the time of my life, learning how to live fully and weather the inevitable ups and downs of running a company.

Can you share the most interesting story that happened to you since you began leading your company?

My life was flipped upside down in October 2017 when my family and I lost our home in Santa Rose in the Tubbs fire. Losing your worldly possessions puts everything into perspective, and as you do during any personal tragedy, you have to take things step by step. If you think too far ahead, you lose your mind. Now, as the CEO of REBBL, this lesson continues to be relevant. The company is rapidly expanding, and we’re learning to take each challenge one methodical step at a time, with purpose and patience. For every new retail opportunity, we pause to consider whether it’s the right outlet before committing. We also keep our company’s mission close to our hearts and never lose sight of what’s important.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I started my career, dot matrix printers were the thing. As you may or may not remember, the paper had those perforated strips on either side, which helped to hold it straight as it came out of the printer — which it did very, very slowly. Anyway, my whole life I have always gone very fast, always wanting to get to the next thing. One afternoon, I was printing my consumer promotions budget and somehow the paper went askew and everything ended up printing lopsided. I decided that I didn’t have time to reprint so I gave this cockeyed document to my brand group to review. Apparently, I had also put my coffee cup on top of it because it had a huge coffee ring right over the numbers. Later, the brand group framed it for me as a joke. I was so embarrassed but I learned my lesson on slowing down (well, maybe just a bit!).

What do you think makes your company stand out? Can you share a story?

REBBL is known for its organic coconut-milk-based super-herb drinks & elixirs, but many don’t realize that it’s a company that was born from a cause, started by the non-profit organization, Not for Sale. The nonprofit’s founders realized that the old model of philanthropy didn’t work long-term and so made it their goal to identify an innovative, sustainable, market-based solution to prevent exploitation and human trafficking in vulnerable countries across the globe. With other thought leaders, they recognized that many countries plagued by trafficking had the right environments for cultivating nutritious ingredients that cannot be found in the U.S. They hired Palo Hawken to cofound REBBL and serve as Chief Innovation Officer, with the mission of creating a brand that would help to sustain the growth of their social justice project by supporting growers to earn a living wage, have access to health care, water, and education, support their labor rights, and pursue regenerative agriculture to keep their land healthy. REBBL provides this as well as nourishing and delicious plant-based drinks for REBBL fans to live healthful lives.


Are you working on any exciting new projects now? How do you think that will help people?

A perfect example of just how dedicated REBBL and Not For Sale are to the empowerment of local communities can be seen in the creation and inception of one of REBBL’s newest flavors, Banana Nut Protein. When the company visited the Peruvian Amazon, we saw the growers cultivating Brazil nuts and asked ourselves, “How could we use this amazing ingredient in a drink?” We then set about coming up with a sumptuous Brazil nut–based beverage and, over the next couple of years, NFS invested in the community’s development and getting the farms certified organic. REBBL, in partnership with NFS, has supported growers’ resiliency by helping them to create sustainable financial independence, and we all get to enjoy Banana Nut Protein, launched this past summer.

What advice would you give to other female leaders to help their team to thrive?

– Build a team of people who are downright passionate about the company and the work that they do. Hire people who not only have great experience but also have fire and the grit to grow within the company and within their careers.

– Support your team in creating deep meaning and purpose in their work so that it is not just a job but a calling.

– Commit to culture, particularly in times of great pressure. For example, we have established REBBL’s Culture Committee, in which representatives from each department work to make sure the company is a place where every team member feels truly enriched, valued, and supported, and that they have work that is interesting and challenging.

– Respect each employee as a whole person. I believe that every part of us — our work, relationships, hobbies, and health — needs to be nurtured to keep our whole being healthy. I don’t believe in gunning it 24/7, and I don’t expect our REBBL people to either. We all need compassion and support to have the energy to keep a company growing. For that reason, REBBL employees get a strong paid leave and parental leave for adoptions and births, and, in addition to a good health insurance program, a Health Reimbursement Arrangement that gives them access to acupuncture, dietary supplements, and other alternative healing treatments, plus memberships to mindfulness apps and monthly massages. On top of that, everyone owns a piece of the company through REBBL’s stock options plan.

– Nurture relationships and focus on -collaboration. A team is so much stronger when its members value cooperation, encourage one another’s input, and work together as a collective.

What advice would you give to other female leaders about the best way to manage a large team?

– Make a large company or team feel connected on a personal level. I do this by showing I care about each individual — for me, it always comes down to the fact that we all want to love and be loved. Whenever I’m in the office, I make sure to allot time at both the beginning and the end of every day to go around and touch base with each person, even if it’s only for a minute.

– Get involved and stay involved, and nurture your relationships with your team. At REBBL, the whole company gets together once per quarter to hang out as people, not just as teammates. After discussing the topic of the day, we do something fun like make pizza, play in the park, or go for a hike. It’s really important that we all keep learning, feeling connected, and being fully immersed in who we are and what we stand for.

– Show yourself as a real person who makes mistakes and does her best to learn from them. Keeping yourself at a distance or trying to look perfect all the time is neither sustainable nor authentic, and people will see right through the façade. If you’re open about your own flaws, your team will see someone they can trust, and they will be more honest about who they really are, too.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Hands down the person who has helped me achieve success is my husband and life partner, Patrick O’Loughlin. I’ve been happily married to Patrick for 21 years, and we’ve been together for 27! Patrick is an entrepreneur himself and so not only does he understand me on a personal level, he’s a huge supporter of my professional career as well. Patrick helps me to remember my priorities. We’ve established values that are important to us — our health, time together as a family — and if I’m so invested in work that I lose sight of those values, he’s there to get me back on track.

Not all of those 27 years have been easy. One of our most difficult tests was when we started a business venture that didn’t work out. We lost our savings and then some. It was a time full of anger, distress, and confusion, but we stuck it out and focused on finding solutions rather than dispensing blame. We have been there for each other during the highs and the lows, and I want him to always know how much I love and respect him. We cheer each other on to reach our goals and dreams, and pick each other up when we’ve reached rock bottom. He is my person, and I am forever grateful to have him.

How have you used your success to bring goodness to the world?

I’ve been passionate about health and healthy eating for most of my life, and I have been so fortunate to turn this passion into a successful career that also spreads goodness to the world. When I was at Clif Bar & Company, my teammates and I introduced the Luna Bar, a decadent whole-nutrition bar for women. When I was named CEO, I was able to help build a company with a deep purpose, dedicated to creating nourishing food for busy lifestyles. Plum Organics was also born out of this desire to make organic, nutritious food accessible and delicious while simultaneously harnessing the power of business to improve the world. Our goal at REBBL, and my personal goal, which I wrote about in Killing It: An Entrepreneur’s Guide to Keeping Your Head Without Losing Your Heart, is to give people great food and make a lasting positive impact on people and environments across the globe.

What are your “5 Leadership Lessons I Learned From My Experience” and why. (Please share a story or example for each.)

1: Your self-worth is not the same as your company’s net worth.

I had to learn this the hard way when a company I was involved in went under. When it did, I did too. I stopped eating, stopped sleeping, couldn’t be there for my family and friends. It’s easy to take a company’s failure really personally, particularly when you so deeply believe in its value and mission, and it feels like part of your identity. Through that experience, I learned that we can’t judge ourselves based on the business’s financial trends. At our core, we need to know that we are much more than numbers in a P&L and cash flow statement. We are humans with a whole ecosystem made up of what’s important to us. We have to be vigilant about maintaining a healthy life ecosystem so that when one part is struggling, the other parts can take up the slack.

2. Innovative companies need to foster innovative ideas, people, and culture.

If you want to make innovative products, you have to have a culture that welcomes innovation, which comes from people who bring new points of view, new ways of understanding the world. Examine your vision and ask yourself: Am I creating a culture that appreciates and encourages people with diverse backgrounds, skill sets, talents, and points of view? This is a question that warrants reflection every single day, no matter if the company is just starting out or if it’s been operating for a hundred years. It always comes back to the people, and whether there is equal access to seats at the table.

3. It’s not enough to just love your business, you have to make sure others love it too.

It’s part of an entrepreneur’s job to help the team connect to the company’s purpose, to make it feel personal and meaningful to everyone. This is an active, ongoing process. Invite people to be part of the story, help others find how their personal passions connect with the company’s purpose, and immerse your team in the brand and the consumer’s POV. If you do this, then you’ll create a company culture where people want to work hard and do what’s best for the company.

4. Be a leader who models love, compassion and care.

Everyone wants to feel valued and seen, not just as employees but as people. Do you know what your colleagues love to do with their spare time? Do you know about the people they care about? Nurture the human spirit because there is no separation between a company and the humans who run it — the human spirit is inherent in the business and the company as a whole.

5. Understand that everyone’s life is an ecosystem.

Your personal life is just as important as your professional life — in fact, I’d go so far as to say that you’d be served by not thinking of them as separate entities and instead simply place them under the category of “life.” Having a well-rounded schedule, in which you can spend time maintaining your health, being with your family and friends, and pursuing your interests, will feed your passion for work, and vice versa. You are never too busy for relationships — rather, your family and friends are vital to keeping you grounded, energized, and inquisitive. So be sure to nourish the different parts of your own ecosystem, and encourage your employees to do the same.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

All you need is love. By inspiring love in not only business but in life, we can reach so many people. If people made decisions out of compassion and love in work, how they use your dollars in the marketplace, and in relationships, this world would be a different place.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Have bold humility. To be bold is to step into the unknown with true curiosity and quiet strength, to proudly say “I’m here and I matter” and, at the same time, approach the world as a student with a desire to always learn and improve. Holding this tension of bold humility is so important as a leader during times of confusion or chaos — being able to have compassion for others and know when to ask for help, to understand your own power and recognize where you need others to lift you up, to have both an explorer’s and a beginner’s mindset.

Originally published at medium.com

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