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Building the Future of Founder Wellbeing with Kelly Fitzsimmons

by Aaron Davis
September 16, 2019

Every week, we shine a spotlight on a founder, designer, researcher or leader in product who is building something that will shape our future. We share these stories to lend our support, spark interesting conversations, and create visibility among a global community of those who are building the future.


Kelly Fitzsimmons is a serial tech entrepreneur, artist, and mother of two. Recently, she published a bestselling book, Lost in Startuplandia: Wayfinding for the Weary Entrepreneur.

She is currently the co-founder 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.

Alpha sat down with Kelly to explore how she is trying to change the work culture of entrepreneurship by revealing truths about what success means, and especially what it can cost when it comes to a founder’s mental health. Below are excerpts and highlights from our conversation:

Alpha: Can you tell us about some things that you’re very proud of in your career, and what you would love for people to know about you?

Kelly: I would say that I have a unique way of looking at technologies, seeing their potential. I tend to show up for really game changing technology innovation very, very early, like way too early.

Showing up before anybody else has been the only real consistency throughout my entire career. Looking around saying ‘where is everybody else?’ and then spending the next five to ten years waiting for the industry to coalesce. There’s good and bad aspects to this superpower, but ultimately I would say that’s the key to my career.

Alpha: What are some examples of how that’s manifested?

Kelly: In 1996, I started an information security firm that was a pure play firm. It was most likely the first in the country, and then when I got completely sick of information security as an industry, about 10 years later, I exited.

Then I went into voice interface, and again, so obvious the technology was ready, however, consumer willingness wasn’t there yet. So, I had to wait a long time at that party for everybody to show up.

Then we ventured into virtual reality in 2012, and I remember it was Jeff, and four other people in a subreddit trying to figure out what to do with this thing called the Oculus Rift, we were part of the original Kickstarter.

So, it’s been a real journey across these different landscapes, but the one thing they all had in common is that they were all in the technology sector, but they weren’t industries in their own right yet.

Alpha: How has experimentation, or the ability to test on learn from your assumptions helped you navigate new industries?

Kelly: Curiosity is the core of it for me. I’m a deeply curious person. I’m always trying to figure out how things work. I also have this unique ability to connect with people who are obsessives. So, they are the ones who go really deep into the technology.

I am the one who is there asking all the questions, and most of the time, what I end up doing is playing the human interface to the rest of the world. Without me, a lot of times the obsessives might just hang out in the basement, and never do anything with their technology. I’ll see the gap, and I’ll wonder why it’s there.

Iteration in traditional product marketing is test, scientific method, evaluate, and customer discovery. I really didn’t learn about that until very late in my career, until I read Steve Blank’s first book, and I’ve been at this for 25 years. So, lots of things and concepts that people hold true today in terms of how you approach starting a business, I didn’t have those tools, they came later in the game for me.

I used instinct, made a ton of mistakes along the way, but a willingness to stay in the pain in spite of it, and that would be really how iteration has been part of what I’ve done. It was much more art than science, if that makes any sense.

Alpha: When you are involved in shepherding a new industry, is your involvement as an educator, or as a pioneer?

Kelly: I would say evangelist. I see it early, I evangelize the market. I’m not a great educator. I don’t have a ton of patience, so if people don’t get it, I kind of move on. There’s better people at this, but the thing that keeps happening is, I’ll call it early, I’ll see it, and I’ll be an evangelist for it, because once I see it, I can’t not see it, and I actually don’t get involved immediately.

So, even though I saw information security really early, I didn’t start my business for at least another year while I sort of sat, and watched, and wondered, and asked questions. With voice interface it was probably three years before I took the leap. With virtual reality, it was also three years. We started tinkering in 2012, but we finally put the company together in 2015, still really early, but it takes a lot of time for me to figure out where we are in the growth curve, where are we in terms of adoption, and does it have a place in terms of the world of business, and it has to be incredibly compelling for me to do that.

Alpha: What is a project that’s maybe a little more recent for you, maybe something in the past year, or a couple of years, that you’ve been obsessed about?

Kelly: In the last year, it’s been related to the world of my book, so I’m completely obsessed with the mental wellness of founders, and am really concerned about the steady state that we’re in as a culture in terms of technology innovation, Silicon Valley, and how startups come into being.

There’s a lot of unchecked assumptions about how businesses are created, and how startups are successful, and unfortunately, almost always, it comes with a tremendous amount of founder sacrifice. The speed of things is getting so much faster that it’s not on a human pace anymore, and so it results in founders experiencing burnout much more quickly, but also in trying to keep up, they are making terrible decisions, because the human mind requires time to process information. What I’m seeing based on the interviews that I’ve been doing, and the conversations I’ve been having with current founders, it’s just a hot mess, and it’s going to get a lot worse before it gets better.

And the things that we’re told as true such as, you have to take on venture capital, you have to scale fast, first mover advantage, really if you unpack these concepts they are not well founded. They support the ecosystem of accelerators, and of early stage investing, and whatnot, but the vast majority of startups really do not, and should not take on early capital.

The phrase “first mover advantage” was first popularized in a 1988 paper by a Stanford Business School professor, David Montgomery, and his co-author, Marvin Lieberman. [1]

This one phrase became the theoretical underpinning of the out-of-control spending of startups during the dot-com bubble. Over time the idea that winners in new markets are the ones who have been the first (not just early) entrants into their categories became unchallenged conventional wisdom in Silicon Valley. The only problem is that it’s simply not true.

First movers have a 92% fail rate, only 8% are successful. However, second movers, which are an average 12 years later than the first have a 52% success rate. The only reason I think I’ve had any success is just pure tenacity, and a willingness to stay in it long enough so that I could become an industry expert, and have the brands that I created with my firms mean something, and be valuable.

There are times when you don’t want the clock running, and that really is in that early phase of the product life cycle. You don’t want to take on venture capital until you know exactly how you’re going to deploy it, and how it makes you make more money, or quite frankly, leapfrog the competition in a meaningful way, and almost always exclusively people take on capital, because they want that first mover advantage. That is not a real thing, it was an artifact of the go-go 90’s and it wasn’t grounded on science.

Alpha: How do you think the book, Lost in Startuplandia, will play a role in building a better future?

Kelly: Well, my hope is frankly to save a life. There are so many founders out there that are struggling, and that is completely hidden. We all have bad days. We all have days in which we question our sanity, and think, ‘Why in the hell am I doing this? No one will ever buy this,’ and yet that schism between the game face, and reality, that’s if we are in touch with reality. A lot of founders get pretty ungrounded, but let’s say that we really know the reality of where we are, versus the reality that we have to project, that detachment is a lie, and it can create a real profound moral injury.

It can be disastrous to our mental health, and well-being when we see ourselves primarily as an honest person who’s trying to do good in the world, and yet we know we’re passing something off that isn’t accurate, and true. It can devastate us, and really set up the conditions for clinical depression.

What about the underlying mental wellness of founders to begin with? Berkeley did a study in 2015, and found that entrepreneurs are indeed special, but not in the way that most of us think. Is it our tenacity, our grit? Yeah, a lot of us have these qualities, but what is really under the covers for a lot of us is underlying issues of mental health disorders such as anxiety, depression, ADHD or substance abuse.

And the thing is, was it the chicken, or the egg? We don’t really know, but this is self reporting, and it was three times the levels of average Americans, that’s self-reporting. That’s pretty staggering, and my hypothesis is that we tend to gravitate towards entrepreneurship for lots of different reasons, but a lot of times one of those reasons is, we’re otherwise unemployable, and it’s kind of a running joke among founders, but there’s a lot of truth to it.

So for instance, with me, I struggle with clinical anxiety. I’ve been in recovery from alcohol for 17 years, and I’ve dealt with crushing depression, and suicidal ideation, but probably the most important thing is that I have severe ADHD, and that is a very common diagnosis of people in startups. Why? We love the new, we love the novel, we like to work in chaotic environments, and startups really deliver.

However, the anxiety that goes along with, and the depression that goes along with ADHD as a diagnosis is pretty profound. So again, chicken, or egg, all I can say is that the underlying conditions are not great, statistically speaking for founders, and then you add the volatility of the average startup on top of that, and it’s a recipe for disaster.

So, my passion right now is really trying to spark a national conversation around founder mental wellness, and seeing if we can start a different, more compassionate dialogue around failure, and what does it mean to fail? Because Silicon Valley does a lot of lip service to failure with phrases like: fail fast, fail often, fail on somebody else’s dime. Those phrases just piss me off like nobody’s business, because they talk to the heartbreaking reality of what it feels like for a founder to close a business, and to lose a dream, and that’s what we’re really talking about, losing a dream.

A dream has been lost, and a part of ourselves does go in that process, and we have to grieve, and there’s time required. So, in this time compression culture we live in right now, that’s accelerating it, founders are being put into a really bad box. It’s like a hotbox that’s heating up way too fast, and they don’t know what to do, because the clock’s ticking.

Once you take on venture capital, or investment dollars, you will go to seed really fast, and there’s not the patience, or understanding that humans still work on a human scale, not a machine scale, and so our time to make sense of our emotions, to process hard things, to make good decisions, to strategize, all require the luxury of time, and that is not available in the current model.

Alpha: What do you think that our future needs more of, and something our future needs less of?

Kelly: So, we need more time. We have to figure out how to reorganize the way in which we live to allow for rest, recuperation, nothing-at-stake time. When the labor movement was going for the eight hour work day, the motto said, ‘eight hours for work, eight hours for sleep, eight hours for ourselves,’ and it was like however you define it, right?

And because it is a requirement that we have our own time, and with the advent of mobile phones, and all of these multiple screens, and this sort of mobile world we live in, none of us is ever truly off the grid. I mean, we have to work really hard to get off the grid, and so there is none of this totally off the clock time, particularly in tech culture.

It’s just not acceptable, and yet it’s required for human cognition, for our brains to properly work, and so the thing that I want to see us do is actually make good on the promise of technology. Forever, the promise of technology is to give us more time, to take away the routine chores.

And that promise has proven false. It actually has made us busier, because now we’ve got some of the chores at home that are taken care of, women can now take their work to the office, and we have both home, and work life, and children. It never created the promised leisure time, and I think it’s high time that technology delivers on protecting our cognition.

We need less artificial demands on time, artificial deadlines, artificial structures that really weren’t thought through. No one ever really thought about it. I don’t think anyone consciously said: we’re going to create labor laws in this country to the point where we are the hardest working country in terms of hours spent at work, of all developed nations, including Japan. In Japan they have a word for suicide by work, by overwork, we don’t even have that word, and yet we work more hours than the Japanese. So, we just kind of fell into this cultural trap of, we have to keep our productivity up, so we’re just going to work ourselves to death, and we’re not machines.

So, what I want us to give up is the culture that celebrates work addiction, that celebrates the person who puts 100 hours a week into their startup that has no relationships, that has no tie to the outside world, is into mass consumption of whatever it may be, whether it’s wealth accumulation, or substance abuse, whatever it is, but they’re not giving back to the community.

They’re not investing in their mental, and physical wellness, they’re truly sucked completely into that entrenched way of thinking, of financial, and success at all means, at all costs, right? Without that self check of ‘what am I actually doing this for? What’s the greater purpose?’ Because the money I can tell you is really hollow. It’s wonderful when you get it for 10 minutes, and then you’re like, ‘okay, why am I not happier? Why did this check in the bank not change everything? Why am I the same person I was yesterday?’

With more money comes more problems, and that’s not, again, part of the larger conversation. It’s kind of hidden by the entrepreneurs who’ve made it, and think, ‘is this all there is? Because if this is all there is, this is kind of shitty. I still feel horrible, and now I have no friends. I’m divorced, and my kids won’t talk to me, great.’

I think there’s a need for us to get really explicit around what are the trades that a founder needs to make, wants to make, should make, can make, and should not make. For example, what are the trades that, by all means that is a point of walking away, and that’s not part of the conversation that we have in tech culture at all.

I would love to see more humanity, and an emphasis on how do we optimize our lives so that our work benefits us, has meaning, and purpose thanks to technology taking on the chore of the soulless grind work that we don’t need to be doing, and how do we shift the culture so that we truly protect nothing-at-stake time, which is the core of our humanity.

Alpha: Is there either a person, or a group of people that has been a significant champion for your work, and how can the readership, and the community around building the future be champions for your work as well?

Kelly: Well today, probably my best champion has been the Maverick community. It’s a summer camp, and I had the real pleasure of meeting its founder, Yanik Silver, four years ago, and it was a life changing experience going to camp, and being surrounded by nothing but entrepreneurs with nothing-at-stake time.

We were able to play, share stories, encourage each other, and so out of that came the ability to finish my book. I had been toying around with it, but it wasn’t until I was at camp, particularly that second year where I saw the need, and the need was really acute. People were struggling. I had been a counselor that year, and had spoken about the mental wellness piece, and my own suicidal ideation when one of my startups failed, and I was personally on the hook for $5 million, and I had like $50,000 in assets, and I had no idea how I was going to get out of it.

And after that talk, I had about 16 campers, entrepreneurs come up to me separately, tears in their eyes, and start talking about their suicidal ideation, and I mean, the camp was only 150 people. So, over 10% of people showing up, that was a pretty significant sample size.

At Alpha, we search for catalytic opportunities to support founders in their efforts to build the future. We asked Kelly how the community can support her and her mission?

My personal mission always is, how can we use technology for good, and I guess another course thread through all my career has been I could always see the downside. We are already at a 50 year high in the US for suicide, that is terrifying, and entrepreneurs are not tracked as a category in terms of the overarching statistic. Based on anecdotal conversations, and also the UC Berkeley study, and some other reports, I know we’re in trouble. What do we do about it? Not just me, but what do we do about it? How can we get at this? To start with, I believe is successful entrepreneurs stepping forward, and saying, ‘My bio is a lie, because it doesn’t talk about my failures, it is a piece of art, but it is not the truth.’

The gaps in it, the time, what I don’t put into my bio says more about me, and my journey than what’s in my bio, I think successful entrepreneurs need to tell it straight, so that the real story of how hard this is, how heartbreaking this is, what the true role of failure in success, so that entrepreneurs who are coming in aren’t left feeling like they’re the only idiot that’s ever made a catastrophic mistake, or that they are completely alone, and nobody has ever been where their have been, because that’s the setup really for people to go into hiding, and for the monsters of mental illness, and suicidal ideation to really take root.


You can find information on Kelly and her book Lost in Startuplandia: Wayfinding for the Weary Entrepreneur, by following her on Twitter, Facebook, and LinkedIn.

If you feel we can lend our support the work you’re doing, please reach out to Aaron Davis, Alpha’s Head of Community, at aaron.davis@alphahq.com

Aaron Davis

Head of Community at Alpha, the platform that enables management teams to make data-driven decisions about users, products, and new markets.