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Women Of The C-Suite: “Physical health is mental health” with E. Keller Fitzsimmons and Chaya Weiner

Physical health is mental health. I used to loath working out. I didn’t have time for the gym. I wish someone had told me that exercise increases neurogenesis years ago. As a part of my series about strong female leaders, I had the pleasure of interviewing E. Keller Fitzsimmons, a serial tech entrepreneur, artist, and mother […]


Physical health is mental health. I used to loath working out. I didn’t have time for the gym. I wish someone had told me that exercise increases neurogenesis years ago.


As a part of my series about strong female leaders, I had the pleasure of interviewing E. Keller Fitzsimmons, a serial tech entrepreneur, artist, and mother of two. Recently, she published her bestselling book, Lost in Startuplandia: Wayfinding for the Weary Entrepreneur. She is the cofounder of Custom Reality Services, a virtual reality (VR) production company whose first two projects, Across the Line (2016) and Ashe ’68 (2019), premiered at the Sundance Film Festival. Keller is the recipient of the Silvertip PwC Entrepreneurship Award and Speech Technology’s Luminary Award. Her work has been published by Network Computing, InformationWeek, and Inc. An active angel investor, she serves on the technology committee for BELLE USA, a venture fund that invests in women-led startups. Originally trained as a classical archaeologist, Keller holds a master’s degree from Harvard University.


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

In 1995, I started in technology working at a Bulletin Board System (BBS) called Vortex, which turned out to be perfectly named as it sums up how it all ended. After a year of chaotic, swirling mismanagement, we walked in one day to learn that Vortex had sucked itself into nonexistence. In the aftermath, I started my own company, Sun Tzu Security, with a unique business plan. I would imagine what the founder of Vortex would do and then do the opposite. To date, Sun Tzu is the most successful of my companies. I merged it with Neohapsis in 2003 and led the combined firm until 2006. We had not taken on venture capital, so when we were purchased as part of an industry rollup, I was able to pay off my debts and invest the remainder in my next startup, HarQen. In 2015, Cisco acquired Neohapsis.

I have a gift for seeing the potential of emerging technologies. Over the last 25 years, I’ve started companies in three different technology sectors before they had properly coalesced as industries: information security (1996), voice interface (2006), and virtual reality (2012). I keep showing up for the party way too early. VR has been the first to pop within a reasonable amount of time.

Beyond my interest in being at the bleeding edge of technology, I am an entrepreneur because I would be otherwise unemployable.

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

In 2016, we had just premiered our first VR project, Across the Line, at Sundance and our nascent company, Custom Reality Services (CRS), was now touring our work globally. It felt like we were on a rocket ship, counting down to launch. Just prior to Sundance, my mother had died and then, in May, my sister passed away unexpectedly. Two months later, I lost my ability to read.

When I lost my ability to read, I had to resign from my boards and take a sabbatical from work. My self-belief shattered. What if I can no longer be an entrepreneur? Who would I be now? These thoughts haunted me.

As I slowly regained my health, I started focusing on “little acts of courage” to rebuild my self-belief. If I saw someone do something badass, and then I did it, by the Transitive Law of Badassery, I would be a badass too. This led me to take on challenges that scared me, including taking the stage at a live band karaoke fundraiser dressed as Joan Jett and belting out “I Love Rock ’n’ Roll” in front of 200 people. By taking action, I witnessed my own bravery and rebuilt my self-belief. Another act of courage was writing my book, Lost in Startuplandia: Wayfinding for the Weary Entrepreneur, even though I couldn’t read at the time.

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?

Early on in my career, I didn’t know how to act like a CEO. I was 25 and trying to look sophisticated. I needed a mentor desperately but was too shy to ask anyone. So, I watched Star Trek Next Generation and took my leadership cues from Jean-Luc Picard. I would walk around the office and say things like, “Make it so.” It is still cringe-worthy.

I guess the lesson here is choose your mentors wisely, preferably real people.

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

We chose a niche in virtual reality early on that intentionally stymied our growth: social justice. We felt strongly that VR was a gamechanger for telling stories that mattered. For the first time, a viewer could walk in another person’s shoes. It was compelling as a vision but was harder to justify as a business. VR is still an emerging industry. Non-profits and foundations, our primary customers, are not known for being early adopters. To be doing social justice work meant that we were eschewing venture capital on purpose, even though there were millions of dollars flooding the early stage VR startup scene. Having taken VC with a previous startup, we chose to take a different route and build a lifestyle company. Now with two critically acclaimed projects, Across the Line (2016) and Ashe ’68 (2019), we can say it was the right choice for us. That said, it felt dicey at the time.

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

I am focused almost exclusively on my book right now. In May, we published Lost in Startuplandia: Wayfinding for the Weary Entrepreneur. My higher intention is to destigmatize and discuss real, heartbreaking failure in a compassionate way. The fact is that failure is a significant part of the entrepreneurial journey. Silicon Valley does a lot of lip service to failure with catch phrases like “Fail fast” or “Fail often” or “Fail on someone else’s dime.” These pat sayings do a disservice to entrepreneurs who are dealing with the reality of losing their dream. Startup culture confuses iteration and failure. Iteration is part of a healthy business model and product development lifecycle and can be approached unemotionally. But when a business fails, it is deeply personal. The loss needs to be processed, grieved, and honored.

Today, I am traveling the country talking with entrepreneurs in an attempt to spark a national conversation. Almost all successful entrepreneurs have weathered countless failures. None of our bios reflect that reality, which leads others to believe that they are the only idiot who has ever made a catastrophic mistake.

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

It all starts with self-care. As women, we are enculturated to put everyone else first. In business, this often means we neglect ourselves because nothing else can give. Or at least that’s how we perceive and justify it.

I did this. I spent a year in and out of the emergency room 54 times. It never dawned on me that I could die. I had a startup that had taken on venture capital. I couldn’t let the team, investors, customers, blah, blah, blah, down. So, I spent my family time either in the ER or locked in my bedroom with a crushing migraine. Our girls were 7 and 5 when I finally stepped down as CEO and focused on my health. Did they get their mom back? Sadly, not entirely. I would spend the next five years fighting to get my health back.

It’s like they say on airplanes, “Put the oxygen mask on yourself first before assisting others.” I think they keep repeating this because the women on the flight never hear it.

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

Effective leadership requires self-awareness, yet that trait is as rare as chicken lips. Years back, my executive coach, Jan Smith, asked me: “How can you lead others when you don’t know what’s driving you?” She was right. I didn’t have a clue what was really driving my decisions.

While 95% of people report being self-aware, a three year study found that only 1 in 10 actually are. Most of us know our aspirational selves, but few of us are open to spending time with our inner demons. It would take a great deal of personal development work for me to finally see that I was desperately afraid of being seen as stupid, crazy, or a failure, I would do ANYTHING to look the opposite. That’s what was motivating all of my decisions — an unconscious drive to always “look good.” This is not the best system for quality decision-making, yet almost all of us do it.

To make clear-headed decisions, we have to wake up to our cognitive biases and shadow selves. None of us sees the world as clearly as we think, which leaves us vulnerable to poor decision-making. We have to figure out what is driving our own behavior before we can effectively lead others.

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?

As a serial tech entrepreneur, my life has been a single-minded pursuit of one goal: impressing my father. Success is a hard thing to gauge. People can succeed financially in business and yet fail as human beings. As an entrepreneur, my dad, Donald W. Baumgartner, set the bar very high with a remarkable legacy. For over 65 years, his company, Paper Machinery Corporation (PMC), has been not just an industry leader but responsible for supplying the machines that manufacture over 90% of the world’s paper drinking cups — Starbucks, McDonalds, Dixie, all of them.

In the 1950s, he made a conscious decision to reject plastics in favor of paper well before most people understood the environmental danger posed by plastics. This would earn him an honorary doctorate from Northland College for his service to the environment.

In 2016, he did something almost unprecedented. At the age of 85, he walked away from over $100 million dollars to turn over the ownership of his company to his very surprised and delighted employees. He did this because he wanted the people whom he credited for his success to achieve their financial dreams too. PMC has line mechanics who became millionaires thanks to this decision.

My dad accomplished the rare combination of succeeding both financially and as a human being. I am deeply grateful to have such a remarkable role model in my life

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

What I learned the hard way is that entrepreneurs are special, but not in the way most people think. We are often in a life or death struggle.According to a recent U.C. Berkeley study, entrepreneurs are three times more likely to struggle with mental health issues. When these underlying conditions combine with the volatility of the average startup, it’s a recipe for disaster.

In my book, Lost in Startuplandia: Wayfinding for the Weary Entrepreneur, I talk openly about my own struggles when one of my startups failed and left me personally on the hook for $5 million. For three years, I dealt with crippling depression, anxiety and suicidal ideation before finding a way out. I have been touring the country and meeting with founders to spark a national conversation around entrepreneurship and mental wellness. We don’t have numbers for entrepreneurs specifically, but the U.S. is at a 50 year high for suicide. I feel a great deal of urgency to change the way we talk about startup failure.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

1. We matter just for being alive. I have spent most of my life trying to prove my worth. It took the loss of my health to regain insight into what is most important — being alive. Period.

2. Our most important job as leaders is to take care of ourselves. If we are missing sleep and eating poorly, we are a disaster waiting to happen. A lack of routine self-care directly impacts our ability to make sound decisions. As leaders, we are the deciders. If we are discounting ourselves and our health, we are not trustworthy. It’s only a matter of time until we break.

3. Physical health is mental health. I used to loath working out. I didn’t have time for the gym. I wish someone had told me that exercise increases neurogenesis years ago. I may not work out to be a size six, but I will work my ass off to get smarter.

4. There are two things that determine the quality of our lives: luck and the quality of our decisions. We cannot do a damn thing about luck, but we can learn how to become better decision-makers. I was not aware how to do this until late in life. What I’ve learned is that it is all about checking our biases and triangulating with trusted others. Going it alone is never the right decision.

5. Honesty is a critical trait in leadership, but no one ever says why exactly. The reason is twofold. First, honesty is less resource intensive. When we are honest consistently, our mental chatter fades away — nothing to keep straight or manage. We free up countless cycles to focus on what really matters. Second, when we lie or even “just” withhold information (little white lies, lies of omission), we will inevitably treat the other person poorly. We tend to be very critical of the people with whom we are most dishonest. We have to belittle them to justify our deceit. It’s human nature. We all do it and it kills relationships.

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. 🙂

In the U.S., we are working more hours than any other developed nation, including Japan, and yet we are feeling increasingly behind. More work doesn’t make us more productive. There is a point of diminishing returns. We have slipped into a culture that celebrates work addiction and fails to see its universal harm. With technology removing mindless, soulless work, we have an opportunity to ask new questions. How can we optimize work so that it consistently unlocks our greatest collective potential without consuming our individual wellbeing?

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

Henry Ford famously said, “Whether you think you can, or you think you can’t — you’re right.” Self-belief is everything in leadership, but it’s fragile.When my health failed and I lost my ability to read, I surrendered my self-belief and thought I could no longer call myself an entrepreneur.

What I learned over the next three years is that identity is a declaration. We get to declare who we are and what we stand for. We don’t have to have powers vested in us by an external authority. We get to say what we believe to be true about ourselves, but it’s a double-edged sword. When we see ourselves as a victim of circumstance, we have to fight against that declaration to make progress. The story hobbles us. In contrast, we can choose to see ourselves as winners, capable of overcoming the odds, our energy can then be focused on the external challenges in front of us, not our internal ego struggle.

A good example of this is my Aunt Miriam, who I talk at length about in my book. She declared herself a winner, in spite of being 21 with three kids, an alcoholic ex-husband, and no college education. She went on to become a top executive at a Fortune 500 company out of her declaration. She won, because she believed she could win.

We are the authors of our realities.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

I would love to have lunch with Tim Ferris. His passion for psychedelic research is of particular interest. Over the last decade, I have had the honor of knowing and supporting researchers whose pioneering work is providing new approaches for the care of treatment-resistant anxiety and depression.

Thank you for all of these great insights!

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About the author:

Chaya Weiner is the Director of branding and photography at Authority Magazine’s Thought Leader Incubator. TLI is a thought leadership program that helps leaders establish a brand as a trusted authority in their field. Please click here to learn more about Thought Leader Incubator.

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