Friends - Chris Shimojima

Founder and President, C5 Advisory. San Diego, CA

Mark met Chris during lockdown through an introduction from Drieke and the Kouch Culture team. He quickly became a friend, mentor and collaborator, generously sharing his network and skills with us. We’ve worked together on a few brands, and his experience and thoughtfulness have been invaluable, helping us forge new connections and friendships around the world.

Thank you, Chris!

How would you describe yourself, and what drives you?
Having been born and raised in Tokyo, my bicultural background has significantly shaped who I am. Early in my career, I struggled to balance the Japanese cultural values of group harmony, humility and sincerity with the American values of individualism, competitiveness and informality. It raised a key question for me: how do I establish an identity that is both authentic and effective? It wasn’t until mid-career that I found the answer. I realized that you don’t have to be the charismatic extrovert often portrayed as the ideal American CEO to be a successful leader. As an introvert, I’ve thrived by following a simple formula: enjoy what you do and stay passionate about it.

For me, integrity is the most important guiding principle. It’s the foundation of my actions and decisions.

What pivotal moments have shaped your journey so far?
I have made three pivotal career decisions that have defined my journey.

The first was leaving AT&T to join kozmo.com in December 1999. At the time, e-commerce was still unproven, and it was considered a high-risk move. I was already established in a solid mid-career position as a GM, and few peers at my level were making such leaps. But my instincts told me it was the right path, and I never looked back.

The second pivotal moment was when I chose to leave Nike to become the CEO of Provide Commerce, an e-commerce pureplay owned by Liberty Media. While stepping away from Nike wasn’t easy, the opportunity to lead a company as a CEO was truly a once-in-a-lifetime chance.

The third turning point came after the successful sale of Provide Commerce. I decided to step away from management and shift my focus toward advising and mentoring CEOs and C-suite leaders. It was a natural evolution of my professional endeavours, allowing me to leverage my experiences in a meaningful way.

What is your relationship with Mark and Russell?
I thank the pandemic for connecting me with Mark and Russell. My former colleague from Nike, Drieke Leenknegt, hosted a weekly Zoom room called Kouch Culture during the pandemic lockdown, where I met Mark. Mark and Russell had just kicked off their new venture, Against Time, whose mission I was very intrigued with. This led us to collaborate on a few projects.

What has come out of any relationship and collaborations?
I consider Mark and Russell to be close confidantes of mine. While collaborating on projects is rewarding, we frequently have touch-bases just because we enjoy discussing different topics. Each of us brings different perspectives and insights to these conversations, and I have found them to be tremendously rewarding.

What does being unorthodox mean to you in your work?
I’ve never consciously aimed to be “unorthodox” in my approach. What matters most to me is authenticity. To me, being true to myself is the foundation of integrity, which is at the core of everything I do.

What beliefs have guided you through tough decisions?
Every decision involves multiple stakeholders. While the ideal outcome is one that benefits everyone equally, this isn’t always realistic. The best decision-makers understand how to prioritise the most critical stakeholders while still maintaining a balance that considers others’ needs.

What challenge in your field of work is often overlooked?
Every company that I have advised has inefficiencies in how they work. Yet, most CEOs do not spend enough time on correcting this by re-engineering the company’s processes. With the emergence of AI, companies today have the golden opportunity to rethink how work gets done and, more importantly, what the workplace will be like with AI.

How do you balance creativity with structure / order with chaos?
I think there are many ingredients to drive creativity in a company. It starts, however, with the culture. A creative culture is one that embraces curiosity and focuses more on asking the right questions rather than obsessing over finding the right answer. A creative culture does not penalize mistakes but encourages risk-taking. A creative culture understands that ideas come from every place and everyone, requiring internal processes to facilitate such idea exchanges.

What cultural shifts are you noticing in your field of work?
There is a heightened awareness of the importance of corporate culture that creates a highly engaged workforce.

If you could master any skill instantly, what would it be?
The ability to learn new languages and converse as a native speaker.

What’s one experience everyone should have at least once?
Live for an extended period of time overseas in a different culture.

What has inspired you lately?

“Cured” by Jeffery Rediger, MD.
This book is about real case studies of the “miraculous” recovery of terminal cancer patients and what contributed to their miracle cure. The author is a physician who studied many cases of such spontaneous healing with the desire to find a scientific basis for these phenomena.

“Outlive” by Peter Attia, MD.
Dr. Attia has written a seminal piece on how anyone can lengthen their lifespan with conscious behavioural changes.

I have a message to all the ‘young’ readers of this….read these two books before you hit middle age.

Our current healthcare system focuses on disease treatment and not enough time and effort is spent on facilitating wellness. What the two books espouse is the importance of each one of us ‘owning’ our health. We can minimise or eliminate entirely the chance of developing diseases by focusing on good lifestyle and behaviours. The earlier you start this the better.

What advice would you give to young people starting out in their career?
Read above.
Your health is everything.

Bonus Question from Fi : What’s the most exciting or beneficial thing to come out of an unplanned career pivot?
After we sold Provide Commerce, I made a choice not to pursue another CEO role. Instead, I teamed up with two former colleagues to start Daasity—a move that thrust all three of us into uncharted entrepreneurial territory. We knew there was a “blue ocean” opportunity, so we dove in, learning as we went. It was both exhilarating and humbling, proving that you’re never too old to master new skills or tackle unfamiliar challenges.

At the same time, I began my “second act” as a mentor and advisor to CEOs and C-suite leaders. Serving as a board director, an executive-in-residence at a start-up incubator, and a consultant, I’ve helped leaders refine their vision, strengthen their teams, and grow their businesses. Through these experiences, I’ve found a sense of purpose—my own ikigai—that affirms what my friend Mark Fleming and I once discussed: growing older isn’t a path to irrelevance but an invitation to discover new meaning and contribute in fresh, impactful ways.

Bonus Question
What question would you like us to ask the next person?
If you could pick another profession, what would it be and why?

How can people connect with you, get involved or take part in any of the projects you’ve highlighted above?
Reach out to me via Linkedin: https://www.linkedin.com/in/clshimojima/