Entrepreneurship seems like a thrilling, lucrative adventure until things go horribly wrong and as crisis after crisis hits, even the most seasoned founder can get disoriented. E. Keller Fitzsimmons has been there, done that, starting six businesses over 20 years. Her book is Lost In Startuplandia and the book is an honest personal guide for surviving startup failure.
She is here with us today, sharing her journey, her trials and her triumphs, and of course her invaluable advice with us.
E. Keller Fitzsimmons: The impetus for the book was born out of a really difficult period of time for me. I had gotten very ill, and our doctors were stumped. We really didn’t know what was going on. I was dealing with severe migraines and fatigue that would leave me bedridden for days.
On top of it I lost my ability to read, and this wasn’t a new problem for me. I have dyslexia. I was born with severe ADHD. I didn’t start reading until I was 20, but after 20 my brain rewired itself and I was a slower reader, but I was pretty good. I was able to write professionally and things like that. But all of a sudden my reading comprehension just stopped. It was like autocomplete.
So I couldn’t work. I couldn’t read an email. I could never trust what was on the page. I stepped off the board of the company, one of the companies I had founded. I had a new startup that was about a year in, which is one of those real critical periods of time for a new company. And this is my current company, CRS.
I had to take a six month sabbatical, and it was really an open ended sabbatical. We didn’t know if I was going to be able to come back to the startup.
I spent most days in bed staring at the ceiling. I quickly tired of audiobooks and movies. There was just nothing I could do, and with migraines and such, there’s very little you want to see or hear. So a lot of thinking time, and that’s pretty rare for somebody who comes out of the world of venture-backed startups. If anything, universally we are time starved. We are task rich and strategy poor.
Getting that higher level, quiet thinking time is not typical in that world. So suddenly I had nothing but thinking time. There wasn’t anything else to do, and I started sense-making over the course of my 25 year career in tech startups and thinking about the context, the culture, the people, and about even the concept of what makes an entrepreneur.
In that process I had a discovery. I realized that the one thing that links all entrepreneurs is an ability or willingness to stay in discomfort for unreasonably long periods of time because more than 50% of it is luck and you have to be in the game long enough for the winds to turn in and favor you. And that sort of epiphany felt really profound at the time. I’m like, huh, that’s fascinating. I thought about the hundreds of entrepreneurs that I knew and the successful entrepreneurs I knew. And that was really true.
And there was also a big question around failure and how we handle failure. I had the privilege of being friends with some very successful entrepreneurs, and I knew the backstory. I knew their failure stories, but these were not public narratives necessarily. These were the stories that they would tell in tight circles, particularly around other friends that were entrepreneurs.
I kept thinking the truth is that no entrepreneur that’s successful has ever gotten there without loads of failure.
Our culture, even though we have niceties that we say about failure, about fail forward or fail often, or I want you to fail on somebody else’s dime, so I only fail. I own these fund startups that the founder has already failed. These are things that you hear. They’re pretty trite in Silicon Valley. It’s a lot of, it’s a lot of hooey. Basically. It’s just, it’s not the truth.
Failure is very, very personal. There is deep shame that goes along when we fail, and for a lot of people, they tap out of Startuplandia. Yeah. They just can’t do it. Obviously, I wasn’t made for this.
Then the real kicker. I went to a camp for entrepreneurs, a place called Camp Maverick, which I absolutely adore. I went to camp and I met the founder. I had this extraordinary experience there, and the next year he invited me back as a counselor. At this point I was starting, I had made some good headway on the book and I decided to talk about mental health and entrepreneurship and reveal that my startup failed when I was 29. I was on the hook for $5 million in personal guarantees, and I had no vision for how I was ever going to get out of that kind of debt.
It was just soul crushing. And three years later, I finally was able to exit a startup and was able to repay that debt. I never talked to anybody about the pain I was in. If you had known me at that time, I was in a new relationship with, who is my husband now, Jeff. I was a CEO of a very successful, profitable company, but I was suicidal because I had that debt. That secret debt.
I shared that story at Camp, and over the course of the next two days, I had 16 individuals come up to me and tell me that they had suicidal ideation.
These are very successful entrepreneurs, and I there were only 150 people at Camp. So more than 10% had the courage to come up and say that, which meant there were others.
And then one night, there was a big party and I spent that night out on the veranda with an entrepreneur who was suicidal, and his partner had brought me over. His business partner brought me over because she was really scared for his safety. And we sat there and we talked. And that night she also found out that her previous business partner had just committed suicide.
I went, “Shit, I had no idea.” I had no idea how bad the situation was.
So in the course of writing the book, I started to dive into the research. I found a study from UC Berkeley that discovered that entrepreneurs are three times as likely than the average American to have underlying mental health issues such as depression, anxiety, bipolar, ADHD. And for me, with the exception of bipolar, I have all of that. And, and, and I’ve experienced all of that. And when you look at the volatility of the average startup, this is a recipe for disaster.
We don’t track statistics on entrepreneurial suicide. That’s not part of the larger, you know, conversation around the suicide epidemic in the United States.
So we don’t really know. It’s all anecdotal. And unfortunately, since in the process of writing this book, I’ve heard of two other deaths. So there was an urgency for me to get the book done and create a platform by which to talk about this really tough, not sexy, not really even media friendly conversation, that’s desperately needed because the first step to relieving the shame that can lead to the spiral and the depression is for people to know they’re not alone.
Rae Williams: I’d love to know from you exactly what Startuplandia is.
E. Keller Fitzsimmons: Yeah. So Startuplandia is a media creation. If you believe the press around Silicon Valley and startup life, you know roads are paved in gold from the venture capitalists who are writing checks based squarely on napkin sketches. Disruption is worshipped as the godhead. And all of us entrepreneurs are heroes that are slaying the dragons of obsolescence.
And it’s this real hero’s journey story that’s put out there.
For someone who has spent so much time in the tech world and particularly venture backed world, which as a female is pretty rare in the founder position. I got a front row seat for this. And so I realized that it’s particularly after the dot-com crash and then the great recession, I really got to experience from the CEO chair and the founder’s chair, the seedy underbelly of this experience.
And it’s much more like Middle Earth then Shangri la. And that’s not ever covered because it doesn’t fit the narrative for most of us entrepreneurs. We want to tell our hero’s story, and that usually involves act three, our success. And there is an entire literary genre dedicated to entrepreneurs who are quick to claim themselves as the magic and they’ve got this replicateable mojo. And if you just follow their steps, you’ll be successful.
It’s just utter BS.
Part of me writing this book was as a response to that. But there, you know, if act three is glorious enough, you might hear about act one where the entrepreneur is in the garage and their, you know, putting together, you know, their prototype with duct tape and chewing gum and a broken speak and spell and they’re going to change the world, right?
And we never talk about act two, and 98% of the journey is act two, which is the conflict and the struggle. How desperately hard this is and how rarefied real success is. Every entrepreneur has a slide that they’re going to be $100 million in five years.
I know a lot of entrepreneurs who have achieved this, but statistically speaking it’s about six a decade. And that’s shocking. It’s like nobody tells you the math. It’s kind of like the lottery, and it’s incredibly stacked against you.
If you think you’re going to be the next Google or the next Facebook, Twitter, whatever, you are really aiming at the wrong space. Companies tend to exit from between about $20 to $75 million is a sweet spot. And if you don’t know the math, you can really screw up on how you value your company and set up not just yourself but your investors for real disappointment.
Rae Williams: How do we start navigating? I’m assuming Sighting your Summit has something to do with that.
E. Keller Fitzsimmons: In the beginning, almost all of us are rosy eyed and bushy tailed. We’re ready. We’re going to conquer the mountain. I’ve taught classes in entrepreneurship over about 15 years, and one of the things that always surprises me, and it should never surprise me, but it does, is how not seriously the entrepreneur takes the actual idea.
They want to be an entrepreneur.
That’s the category, that’s the dream. But the idea underneath that of why and how they’re going to manifest this dream of being an entrepreneur isn’t really vetted. It’s not based on necessarily in their personal passion.
I have heard “looking for the big idea,” right? And that’s not about the big idea. The big idea that isn’t grounded in your own personal expertise and or passion is not the right idea for you because you really need to care about this on a visceral level. It has to have impacted you somehow.
So typically when you’re looking at your summit, a lot of people start out of anger. Something just went terribly wrong for them. They had a terrible experience. There’s a great story about the founder of The Knot, and it was about her rotten wedding experience. That is very prototypical for successful entrepreneurs, because they know the pain of the problem personally. They’ve dealt with it, they had to work their way through it, and they don’t want anybody else to have to deal with it.
That can be some of the best founding mojo.
Although I will caution, anger is a great motivator to get you started. It is not a great sustaining energy. At some point, passion has to take over, or you’re just so immersed and so loving what you’re doing that the pain of the everyday disappointment and grind that inevitably comes with trying to manifest something from nothing, doesn’t break you in the process.
So this ultimately comes down to really having a great definition of what is your summit? What are you looking for? In our culture, we’re very quick to define financial success as a summit. But having achieved that and coming from a family of entrepreneurs that have achieved it, I can tell you personally, it’s incredibly hollow.
It’s hard to say that to somebody starting out.
Like they’re like, “Yeah, it is for you, but it’s not for me.” But it’s sort of the universal story. You get there and you’re like, “Wait, is this all there is?” And if you’ve burned your relationships and thrown you onto the pyre of sacrifice for achieving this goal of financial success, you have failed. You have failed as a person. Silicon Valley is littered with entrepreneurs that on paper are very successful, but as people, nobody wants to be with them.
That is tough. That is a very tough break. And unfortunately the current narrative around what makes a successful entrepreneur doesn’t tell that story. That there’s two levels to it. You have to first succeed in the business realm, but you need to also succeed as a person. Otherwise that first piece doesn’t matter.
Rae Williams: How do we begin to succeed? What is one thing that people can just take action on immediately that will help them to connect that piece?
E. Keller Fitzsimmons: The importance of relationships. So when I was 29 and at Prism, the company failed. The one that left me with the debt. I had my marriage at the time blow up too. I married at 25 I started my company at 25 and by 29 I was a hot mess. I hadn’t spent any time with my friends. I hadn’t built any of the relationships are connected with family or anybody else. It was just like this utter void of relationships to fall back on when I failed.
And at the time too, I’d also spent nine years not talking to my biological mother.
So it was this just, when I fell I just kept falling. And that’s a very dangerous place to be. That lack of connectedness. But it’s dangerous in two ways. It’s not just dangerous for when you fail, because it really does set you up for depression. The other piece of it is that it fails you because you’re not making good decisions.
Relationships require, if they’re healthy relationships, truth. People’s willingness to share their perspectives with you. I’m not using truth in the capital T sense, but more their perspective. Because good decision making is all about triangulation. As I said earlier, luck is such a huge piece of why any of us are successful, but there’s a second component to it, which is good decisioning.
And if we fail to include others and have trust in others that we can triangulate are our ideas and our decisions with we are making them blindly. And that process is a failed process.
Even though you might get lucky in a decision, turns out, well it doesn’t mean you’re a good decision maker. And that’s the only thing in our control.
So without relationships and the investment in relationships and the investment of showing up as ourselves authentically in these relationships and trusting them as a place where we can get vulnerable about the stuff that’s not working, we really are flying blind.
Developing Social Connectedness
Rae Williams: So when you say social connectedness, does that tie into the relationships with other people and having other people you know to help you to become a whole person?
E. Keller Fitzsimmons: Nobody can help you be a whole person. And that’s really the work we have to do in ourselves. But what they can do is help us be self-aware. So there’s a wonderful book called Insightby Tasha Eurich, which is around self-awareness, and she researched this topic for three years. The discovery was that while 95% of us think we’re self-aware, only 10 to 15% of us actually are.
And the reason for this is that we lack feedback loops. We don’t challenge our internal chatter with external validation, in a real way.
To give you an idea of what this can look like, it means going to your parents and asking, what can I do to be a better human being? What do you see? Actively seeking out people to help us triangulate and find our shadow, because the shadow—or really our humanness, if we’re being honest about it—the stuff that we don’t want the world to see, the messy stuff, it’s really driving the show and it’s behind all of our decision making.
So to give an example, you know, took me years to get at it, but I realized after the failure of Prism that I had a hidden conclusion. It was a story that I had told myself since I was a child. It said that I was a crazy, stupid failure and it was only a matter of time until people figured it out and would abandon me.
And because of that story, it drove all my decisions. So why did I go into information security in 1996? It made me look really smart. Why did I choose to be a startup CEO? Well, you have look pretty sane and buttoned up when you’re a startup CEO.
For the first four years of me being an entrepreneur, it made me look awesome. It was like I was successful. There were articles almost weekly in the area of business journal about how awesome I was.
It allowed me to put forth the persona of how I wanted to be seen in the world, but it was all driven deeply by this fear of being seen as what I secretly believed to be true.
So it’s our hidden conclusions. It’s these stories that we make up as children about ourselves and the negative aspects we see in ourselves.
We might’ve been teased about this, we might’ve been bullied about this, and we’re going into the world like, “I’m going to show them, I’m going to show them I’m not these things.”
And when you use that energy, ultimately it comes back and you will step right into revealing that you are these things, because ultimately it’s our humanness. If entrepreneurship has any asset to it whatsoever, it is incredibly tough. It’s a gauntlet, and it will expose our soft underbelly and the things that we hide.
It’s just too hard and it’s just too public. Unlike people who can hide in ivory towers or in academia or behind a title in a large corporation, where there is positional respect and authority, entrepreneurship isn’t like that.
When we fail, the world wants to tear us down, and they will see us.
Success in Startuplandia
Rae Williams: So tell me about some of the people who have gotten the most out of your ideas.
E. Keller Fitzsimmons: Yeah, so right now I’m working with a group of artists and we don’t hold it in our culture like this, but musicians are entrepreneurs. If they’re successful, they have to put together an entire business to support their career. I started working with a group called Backline, which is for artists that are Milwaukee based that are looking to break nationally.
It’s a massive process. Getting into it is actually harder than getting into Harvard. The numbers are incredible.
We work with four artists every cohort. I created a companion program around the work and the book and was really at the time for the first cohort workshopping the content to making sure it was relevant and that it made sense.
In the process, one of the artists I was working with really had a breakthrough, and he ended up writing a song. I had pledged not to listen to any of their music while we were in the cohort.
So I had no idea who they were artistically. My purpose in this program was to see them as people and to see them as entrepreneurs that needed to be successful in the world. And I wanted to give them some of the tools and techniques that I learned the hard way so that when they break as artists nationally, they didn’t break his people.
The program was over, and the artist said, “Hey, can you drive me home?” I said, “Absolutely.” And so he figured out how to get his phone onto my stereo and he’s like, “I’ve got something to play for you.” And it starts going, and the lyrics…the tears just started streaming down my face because he had clearly heard what I was trying to give. I had used the program as a context by which to create something incredibly beautiful and powerful, and it’s now coming out in his EP.
There is a deep pride I have in the fact that it resonated so well. But more importantly that that it was helpful to him, not just as a businessperson in a difficult industry, but for him artistically to help unlock something.
A Challenge from E. Keller Fitzsimmons
Rae Williams: So if you had to give a challenge to your readers, what would that challenge be?
E. Keller Fitzsimmons: Turn on the lights. Get real clear about who you are. It’s not our aspirational self. Our aspirational self is who we think we are. It’s a side of ourselves that we constantly do this continuous fan dance to show just the good sides. And in the selfie generation, it’s all about cropping and filters. And that’s never going to get you anywhere.
That’s just your persona and it’s not in charge. It’s just window dressing.
What’s really in charge is the person we are through our actions. And a lot of times we justify our actions. We will be quick to say, “Oh, so and so is so dishonest,” but not recognize our own dishonesty because that’s not how we see ourselves as a person.
We see ourselves as our aspirational self.
One of the things that I challenge a lot of people to do is to try to spend 24 hours doing nothing but telling the truth. Just straight up—and, and lies of omission count. So somebody asks you a straight question, you dodge it, that counts. What people quickly realize is how dishonest we are. And all of us, this is me included.
The research comes back that on average people tell about seven lies per day. And that blows our minds. How is that possible? But then you think about it, your girlfriend asks, “Do I look fat in these jeans?” And you’re like, “You look great.”
We do it all the flipping time, because white lies are part of our social lubricant. That’s how we get through.
Particularly as women, this is really important. We really couch, we dodge. Likability is so important to us as a gender that and culturally in culture, that we will do almost anything but say straight up what’s on our mind.
And so the first step to realizing who we really are is to really get our field notebook out and observe us in the wild. Who are we really if what we really are is our actions? And the other way to get at it too, is to watch the people that you don’t like. Particularly you intensely don’t like.
So they walk into the room, you walk out of the room. What are the attributes about that person that you can’t stand? Here is the really tough part. What you’re seeing is your shadow. That is absolutely a straight up you. And you do these things, it might not be perfectly in the same way, but you do them, and they are what are driving your decision.
So a good friend of mine said, I hate narcissists. And if you looked at him on surface, you’d see he is incredibly generous. He is like one of the most generous guys I’ve ever met. And yet why was he doing that? So no one will see him as a narcissist. He’s activity is driven out of this space and on a level he’s deeply worried about that, but he can’t get there.
You know, sometimes these places are so tender and so tough and our desire not to be seen that way in the world just keeps distorting it. So the more angry it makes you, the more you know you’re on target. So it’s like this wonderful sort of heat seeking missile system. The people that drive us the battiest, they are our mirror. They’re showing us what we don’t want to see in ourselves.
Rae Williams: How can people contact you if they’re interested in learning more or connecting with you?
E. Keller Fitzsimmons: I have a website. It’s lostinstartuplandia.com. There’s a whole contact form, absolutely reach out. I can be followed on Twitter or LinkedIn, and I’m eager to hear and start conversations with people who are going through this. So I really do encourage people to reach out.
I’m also actively seeking to create a platform around speaking on mental health and entrepreneurship specifically, actively looking for opportunities to speak on the topic.