Flipping the Script: How Cara Thomas Is Redefining Entrepreneurship and Embracing Human Connection

Cara Thomas, the Founder and CEO of Flip Mode, is reshaping the way businesses approach growth and creativity.

Cara’s journey began with a personal quest to break free from her comfort zone, which led to her booking a one-way ticket to Mumbai and the creation of her first product, Serenflipity. Rather than following a traditional scaling model, Cara chose a hands-on, referral-only approach, ensuring clients receive unparalleled expertise and an ongoing, collaborative relationship. Ultimately, Cara’s journey is a testament to her commitment of redefining entrepreneurial narratives and her unwavering belief in the power of human connection in business. 

We asked Cara about the problem Flip Mode solves, how her definition of success has evolved throughout her journey as a founder, and what she would tell her younger self if she were to start her entrepreneurial journey over again.

Q: Tell us the story behind your company’s founding. How and why did you start working on Flip Mode?

A: I founded both my consultancy and startup out of a personal need to get out of my comfort zone and get unstuck. I had been working as an innovation consultant for a company that is now part of Accenture. I discovered through my work with Fortune 500 companies that the secret ingredients to creative breakthroughs were playfulness and adventure.

I was in need of that in my personal life, so I booked a one-way ticket to Mumbai and completed 90 adventures that friends, clients, and colleagues had outlined for me. It changed my life, led to unexpected experiences, and sparked the creation of my first product, Serenflipity, an adventure game designed to help people get out of their comfort zones and try new things in everyday life. As I built the startup, I decided to bootstrap it through continuing my innovation consulting practice.

While Serenflipity grew, my innovation practice continued to expand from Fortune 500s to private equity firms and startup CEOs. I began to apply the lean startup principles I had used to build my game and the personal development tools I had been studying to leadership teams at large corporations.

Q: What problem does Flip Mode solve? 

A: When it comes to innovation and product development, we often focus on the mechanics of the idea at hand—iterating and optimizing—and we forget the human aspect of the end consumer, as well as the dynamics of the teams of people who will launch and grow that brand and product. It is people who will be both the creators and consumers of an idea, and it’s critical to champion the human spirit in every decision, whether it’s internal or market-facing.

When evaluating an idea, for example, we go through the traditional metrics of market size, customer need, and differentiation. These are very important, and in addition to that, what I really focus on is whether people within the company are personally excited to bring an idea out to the world. It’s incredibly hard for a new product to survive, so the team’s tenacity, creativity, and resilience are critical for a successful launch in an increasingly tough market.

Innovation is fundamentally a human discipline—it requires creativity, collaboration, and curiosity. While many business executives relegate these qualities to artists, these skills are actually innate to all of us. If we think back to ourselves as five year olds, we all excelled at these areas. I have seen corporate executives embrace these parts of themselves as adults, and witnessed creative breakthroughs, tough and necessary executive team conversations, and tangible metrics, like increased sales and employee retention, happen as a result. 

The integration of head, heart and hands (or thinking, feeling and doing) is what makes sustainable and real change happen.

A: What makes Flip Mode different from other similar companies in the industry?

A: I’ve made the decision to not scale in the traditional way and instead bring on the right partners for each project. I love setting up the right commercial strategy, gathering deep insight and helping companies establish the right culture and behaviors for innovation. This means that I get to take a hands-on approach and bring in vetted collaborators to join me on working with each client. Most agencies work from a leveraged model, with senior talent only having a light touch on a client’s work and focusing more on business development.

I’ve taken a no overhead and referral-only approach, which means that clients are only paying for seasoned, senior consultants they get to build a partnership with over time. This means that many projects become ongoing relationships, and clients often get us as extended members of their team.

Q: What’s the biggest misconception that others have around entrepreneurship?

A: There is a big misconception that you have to completely quit your day job or build your company by raising outside money. One of the best pieces of advice I got early on, when I wanted to leap fully into building Serenflipity, was to continue to earn an income through innovation consulting. It allowed me to keep the lights on, have a financial runway and small amounts to invest in the company’s growth, and to make smarter long-term decisions. When we need funds or cash, or are in a mode of desperation, it’s easier to make a poor long-term decision in the interest of a short-term milestone.

Of course, there were moments where I got to zero and wasn’t sure I could cover my runway. Those were terrifying and they taught me how to keep showing up, how to be resilient, and how to become balanced in the face of uncertainty. And what surprised me is that those moments provided some of the biggest breakthroughs—from getting a publishing deal to a huge consulting project with a large healthcare company that funded the business for a year.

Q: Have you struggled with self doubt as an entrepreneur? How do you navigate this?

A: Of course. As an entrepreneur, I’m not following a path that anyone else has laid out. And if I were following someone else’s plan or path, I would not be in integrity with my own vision. It’s easy to second guess yourself when you’re on the front lines every moment. When I feel uncertain, I remind myself that I am an explorer, and part of that job description is navigating unfamiliar areas, and being excited about bringing clients into new possibilities and the unknown.

A lot of times, the mainstream entrepreneurial narrative can lead us to think that we should banish self doubt. It will always be there, so it’s what we do with it that matters. Sometimes self doubt or anxiety has good information to share with us, keeps us on the top of our game, and, when harnessed, can drive incredible breakthroughs. If we push it away, instead of addressing it or listening to kernels of wisdom that may be there, it can sabotage us.

Q: Has your definition of success evolved throughout your journey as a founder?

A: When I started my journey, I equated success with money and notoriety. As I’ve grown as a founder and entrepreneur, success today is more about contentment, relaxation, and usefulness.

For me today, it’s not just about the financial goals—it’s about what that income allows me to create, and how I can be helpful to the right clients. Am I able to live a healthy and happy lifestyle and do work that helps others? Am I able to spend quality time and be present with those I love? Am I able to give back to and support those in need?

When I was younger, my goal was to eventually become well known enough to have a black and white illustrated headshot in the Wall Street Journal and a write up in Vogue. I have not built my business in a traditional growth-hacking way and have chosen to stay underground and operate through my networks. I work with clients whose values are aligned, and I focus on doing great work that supports their growth and allows them to shine. For me today, it’s about a “fewer, better” approach.

Q: Have you discovered any underappreciated leadership traits or misconceptions around leadership?

A: Love is one of the most underappreciated leadership traits I have discovered. It incorporates appreciation, gratitude, empathy, genuine human connection and even our power of intuition. When we take the time to get to know others on a personal level and appreciate each other’s values and contributions, it leads to better performance, more impactful ideas and more effective collaboration. When employees feel safe and valued, they're more likely to share ideas, collaborate, and innovate. And when we embrace our own capacity to feel, we become more aware of others’ needs and are able to lead more effectively as a result.

Love as a word can feel fluffy—and challenging to create KPIs around. While the hard numbers and financial metrics will always be central to business, the soft skills, emotional intelligence, and the capacity for love and understanding can be equally critical to a company's long-term success and sustainability.

Q: What would you tell your younger self if you were to start your entrepreneurial journey all over again?

A: I would tell my younger self to embrace her quirks and curiosities. There was a period of time where I kept my personal life separate from my professional life, and tried to act more like a Harvard MBA than my true self. I learned from allowing the more esoteric and spiritual side of me to come out in appropriate ways that it made me better at what I do.

Notably, I discovered a connection between the patterns that arise when one does shamanic journeying work and the patterns that arise throughout the creative process. There is a similar roller coaster feeling, and many teams shy away at the moment where things get uncomfortable. However, I found through my own curiosities about the human experience and personal development journey, that I was able to navigate them through the creative “valley of death” and get them to the other side.

I had a client give me the feedback after a five-day sprint with a 12 person team that, as their guide and facilitator, I had taken the anxiety and uncertainty in a room and transformed it into creativity and connection. It was one of the most meaningful compliments I have received—but that skill set was one that I hid for a long time because I didn’t see its value  through a more traditional business metrics lens. By embracing all parts of myself and bringing all of that to clients, I am able to be more impactful to their businesses.

Cara is a member of Dreamers & Doers, an award-winning community that amplifies extraordinary women entrepreneurs, investors, and leaders by securing PR, forging authentic connections, and curating high-impact resources. Learn more about Dreamers & Doers and get involved here.

The views and opinions expressed herein are the views and opinions of the author and do not necessarily reflect those of Nasdaq, Inc.

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