Author, Entrepreneur, Documentarian, Musician
E. Keller (Kelly) Fitzsimmons is a serial tech entrepreneur, artist, and mother of two. She is author of Lost in Startuplandia: Wayfaring for the Weary Entrepreneur. She is also an award-winning speaker and documentarian (as co-founder of virtual reality production company Custom Reality Services). An active angel investor, she serves on the technology committee for BELLE USA, a venture fund that invests in women-led startups.
She has a lot to share about the experience of writing a book and how to navigate the trials of entrepreneurship
Our conversation covered the following:
- Why most art happens “in post”
- The story of writing Lost in Startuplandia (while sick and unable to read)
- Using a book to serve at scale
- The true costs of resilience
Want to know more?
- Find out more about her book Lost in Startuplandia
- Visit Custom Reality Services (her documentary production company)
Listen to our interview here
Read the Transcript
On the journey of writing her book from a place of crisis
A: Hey Kelly, thanks for joining me on this call. I’ve been a fan of yours since reading your book Lost in Startuplandia, which was such a generous, open, and honest account of your entrepreneurship journey. What was it like for you to write that? Tell me about the experience of that, because you shared some very painful stuff, as well as a lot of hard-earned wisdom.
K: Thank you for that. It was not easy. It was a labor of love. As with all great loves, there was heartbreak along the way, finding new and deeper levels. I started writing the book as an act of sense-making. I was very sick when I started writing it. In fact, I started by dictating it into my phone because I was stuck in bed for about a year, dealing with a series of illnesses that I couldn’t figure out. They would manifest in migraines. I couldn’t read, I couldn’t watch tv. The pain was so intense, all I could do was lay in bed and stare out the window at an oak tree.
That was the context of writing the book. It wasn’t, in the beginning, for anybody other than me, just to understand my journey: what did it mean? Why was I an entrepreneur? Why was I doing this to myself? It was clear my illness was related to burnout, and working too hard, and working past doctors’ orders, and not going to the doctor. It caught up with me in a rather spectacular way. That was why I wrote the book. I would love to say that “It flowed and it was easy.” It was so difficult to remember a lot of the things, I ended up having to call and interview people. If I found a particular entry was overly kind to myself, I would go back and, like, “I don’t think that’s true.”
It was an act of slowly peeling apart my persona and getting underneath it. I didn’t want this to be a book about me. It wasn’t about my journey. I was creating it as part of the arc of the story, but it was trying to get at the underlying, universal human concerns.
Why do we do this to ourselves? Why does anyone want to be an entrepreneur?
A: That’s a point I need to make clear for those who haven’t read the book. It’s not a memoir, it’s a wise collection of advice. The memoir part is the illustration. It is a very personal story. That’s the balance. You started it to process. You started to create the narrative and better understand. At what point did it tip into, “This is a how-to book, a prescriptive book?”
K: I never really figured it out until I got the first draft back from my editor. The first draft was terrible. I’ve heard this from other authors: you get your first draft back and can’t believe you actually wrote these words. In my case, it was heightened because I was sick, and dealing with memory issues. So it was garbled and unclear. What was I talking about, what was I trying to do here?
This is the secret of all art: you figure out what you’re doing in “post,” then you go back and stitch it together so it makes sense.
That’s narratively what happened. At the end of the first draft, I read it and thought, “I think I’m trying to help people. I don’t want anyone else to feel the pain I’m feeling right now.”
That was the initial insight. I ended up rewriting the book from scratch. I almost didn’t use any of the original draft. One, I was out of bed and healthier. We figured out that I was dealing with mold poisoning. We had toxic mold in our house. So I’d gone on the Shoemaker protocol. As I got more well, my brain clarity came back and I could start to stitch it together. So the story is full circle. The context in which it was written was harrowing. But the clarity I had when I knew what I was trying to do—trying to be helpful! Suddenly then I had a narrative thread I could pull through. I knew who I needed to talk to. I knew what kind of advice was helpful and what wasn’t, at least on my own journey. And I tried very hard to write from that point of view.
A: I have to say, something that jumped out at me reading the book was that you decided to write the book when you lost your ability to read. Now, this is completely the opposite direction that most people would go. This floored me—I nearly fell off my chair. “I can’t read. What am I going to do? I’m going to write a book.”
K: That pretty much sums me up: the queen of the unexpected. It is fascinating. If I had been in a clearer state, that might not have been my choice. That really lends itself to understanding just how garbled my thinking was. That seemed like a good idea.
I think because I was wrestling with a breakdown of livelihood—which we’re all dealing with right now, this is the universal problem everybody has right now—but at the time I was pretty alone. Everybody’s off and busy and making stuff happen. My girlfriend Julie [Wainwright] is killing it with the RealReal. I’m watching that rocket ship take off. My friend Eric [Klinker] was over at BitTorrent. They’re all doing the cool stuff. I’m the kid that got left behind. I’m sitting here in bed going, “I can’t hack it. I’m too sick, it’s my fault.” Not knowing that I happen to be in a bedroom full of toxic mold making me worse.
“Who am I now that I can’t work?”
K: As I’m experiencing all of this, there is a piece of me thinking, there’s a story I need to tell. There’s a story behind success, and it’s a story that matters. It was also part of trying to figure out, who am I now that I can’t work. And why am I doing this to myself in the first place?
Right this minute, we’re all grappling with that question. Most of our livelihoods have stopped. We can’t do our routine of busy-ness. So, who are we now?
A: That’s true. We’re all in a bit of that crisis now. If we identify by our work, we may be facing an existential crisis.
K: And an entrepreneur does. I write entrepreneur far faster than I write mother or wife. I don’t think wife ever makes the list.
A: Although, you wrote about your husband’s role: he read all of the transcripts, manuscripts and edits to you again and again because you couldn’t read. What a partner.
K: I have a fabulous partner. That’s why I have to laugh. If anything, that should be one of the primarily roles I identify with. But I’m so bad at it. I’m just not a domesticated female. I’ve always identified much more male. I present very female, but our gender roles are reversed in this family. My husband’s six-foot two. He looks like a big burly guy, but he takes great care of me. He enables me to do this. It’s a traditional caregiver role he played to manifest this, and I couldn’t have done it without him.
Entrepreneurs and the cost of resilience
A: The book is very generous because you talk about the real messiness of entrepreneurship, and the mental fact. I also found it fascinating that entrepreneurship tends to draw people dealing with other issues like ADD that makes them fit less comfortably into the traditional workforce.
K: Years ago, maybe 25 years ago, there was a cover story on Entrepreneur magazine about sociopathy and entrepreneurship. He’s an entrepreneur. He said, “You know what? This rings true!” I said, “Really?” He said, “Yes, most of the entrepreneurs I know are sociopaths.” I thought, “Am I a sociopath?”
There’s truth in this. We’re always looking for the elixir. If only we could figure out how to take Elon Musk and Steve Jobs, Mark Zuckerberg—you name the entrepreneur—and distill the quality so we could teach these to the upcoming generation.
The truth is, what makes most entrepreneurs pretty exceptional is disagreeableness, the inability to get along with other human beings.
A: Unemployableness.
K: Yes, unemployableness. Some of it is mental illness. We see things differently because our brains don’t work the same way. We throw labels around so fast and so hard. I’m not the first entrepreneur to talk about this. I was referencing a study from UC Berkeley on mental health and wellness in 2015. They discover—and this was self-reported, which is fascinating—that at three times the rate of average Americans, entrepreneurs self-report that they’re dealing with ADHD, depression, anxiety, bipolar, and addiction. That’s self-reported.
I can tell you anecdotally, from my experience of meeting probably 1000 entrepreneurs over the last 25 years, this is dead true. These are the conversations we have at the bar when nobody else is around. It’s like that scene in Jaws when everyone starts showing their scars.
A: But we tend to glorify the entrepreneur as these rugged individuals. What you’re saying is first of all, there are scars. Second, they are not getting by as individuals. They are needing help.
K: This reminded me—a girlfriend was talking with me about an entrepreneur who will remain nameless—a famous Silicon Valley CEO. She was working with him as part of the executive team. She said, “He’s best on a scale of one to ten thousand.” When he’s on stage, everybody is like “ahh.” When you try to talk to him as a human one-to-one, there’s no connectivity.
We’re all different, we have our niches in the places we play best.
That grit and resilience we talk about so often is hard earned, and it comes from trauma.
It cuts multiple ways. It’s not just a nice, clean, wow, they’re so resilient. Who, also, is getting hurt in the wake of their success. That’s a big piece that isn’t discussed as widely. Oftentimes it’s women.
Her vision for the book: Serving at scale
A: What would you like to see come from your book being out in the world?
K: My number one thing, when I finally got clarity on why am I writing this book… This sounds heavy, but we’re dealing with a real issue in terms of suicide and depression. We’re at a fifty-year high. We don’t have numbers for entrepreneurs. We don’t know. I know that the stressors people are going through, particularly right now as funding is drying up and revenue is drying up. If you’re a young entrepreneur, the last 12 years have been awesome. They didn’t have to go through the Great Recession. They didn’t go through the dot com crash.
There are things I’ve experience in leadership that make now much more palatable. It’s not palatable, but it’s not unforeseeable. When you have nothing in the background: one day it’s awesome and the next day it’s so not awesome, you get whiplash. This is what makes entrepreneurs at this particular time—this is what I was trying to get at in the book—all of our demons love to dance when these particular times arrive. This is the dark night of the soul.
If you take it personally, and think, I was never meant to be an entrepreneur. I can’t raise money, I can’t keep my employees. If you look at this time, it’s not about us. It’s not personal. It’s a universal experience. All businesses go through cycles. Can you keep your emotions and head about you as best as you can and use this as a time for self-exploration so you get better versus doing what so many of us do: going down the shame spiral and thinking that we’re broken and don’t have what it takes. That’s not helpful.
A: As you write in the book, something about successful entrepreneurs are those with a higher tolerance for pain and failure.
K: At the end, I was like, “What makes an entrepreneur?” That was my big insight. An entrepreneur is someone who can withstand discomfort for unreasonably long periods of time. If you can do that, you’re golden.
A: What kind of response have you gotten from the book?
K: I’m so grateful, it’s been such a gift to me. Our search for meaning, it’s all about taking difficult bouts and giving them purpose. There was a reason for that suffering. The feedback on the book has been so universally positive, with individuals reaching out and connecting with me, that I feel like I did a good job. I never say this to myself. The last thing I ever do is pat myself on the back. But in this case, I know that I did as absolutely well as I could have at this point on my journey.
There will be a different book to write. Some day I’ll read it and I’ll cringe, and I’ll wish I said 10 other things. But for that point of time and who I was when I wrote the story in the book, I really feel that I gave it my all, and that it came through and connected with people, and that it is being helpful. That’s the best I could possibly hope for.
A: Yes, you are serving through the book.
K: Yes. Serving at scale, which is a weird thing. I’m very used to serving one-on-one, where I could be there, and give my enthusiasm or light or joy to someone who’s in a stuck, dark place, going “It’s not about you, this is universal, it’s nothing personal.” At the end of it, they’re like, “You’re right!”
Being able to do that moment with hundreds or thousands of people, opposed to one-on-one, feels really good.
A: Serving at scale. That’s what it’s about. So, what’s next for you?
K: In the epilog of the book, I write about this. I’m walking away from Startuplandia and reevaluating. I came to the conclusion that one of the things I was ready to explore was to hold my identity as an artist, which up until three years ago I couldn’t imagine because it was too scary, too terrifying.
You can hide behind a startup and have this as your creative enterprise. At the end of the day, if it flops or fails, there are so many ways it can break, you don’t have to say, “It was my bad artistry.” When it’s art—as it was with the book, putting something out there that’s so deeply personal—when it doesn’t resonate and doesn’t land, it is hard. It is much harder to take those knocks.
I’m finding, as I’m writing music and working on releasing an album in June, I’m getting to a place where that’s not being so true anymore. Same with the book. If I know I did a really good job and gave it everything I had, I’m proud of the work I’m putting out. It doesn’t mean in ten years I’m not going to hear problems with it, or it won’t sound dated. It will. But I’m proud of it right now. It takes a tremendous amount of courage to make art.
My “Acts of Badassery” is my cheat for self-love and self-trust. It’s working with making music. I’m pushing past my fear, doing it anyway. Every time I’m able to hear one of the bounces of one of the mixes I’m working on and it’s gotten a little bit better, it’s really helping my self-esteem. I’m not going into the dark night of the soul of “Why am I not a gifted artist right now?” You’ve got to earn that.
A: And it always gets better in post, as you said, whether it’s writing or music.
K: [laughing] I’ll find the narrative arc of my songs, and then it will be art. Right now, it’s a little in between.
A: The sense that what comes out, whether it’s book or music, that the first pass is genius. Most of us, that’s not how it works.
K: Never. Even Dave Eggers with book A Heartbreaking Work of Staggering Genius, his first novel. I’m sure he had multiple drafts before he published.
A: I’m pretty sure. Thanks for sharing this. I think your story will be inspiring to people.
