172 Kelly Fitzsimmons: Failing Forward in Startuplandia

Kelly Fitzsimmons is a 4X serial entrepreneur and pioneer in voice recognition technology, cyber security and virtual reality with several 8 and 9 figure businesses and exits to her name. She shares her ups and downs and important advice for women about how to leverage, profit and grow (and never hide) from failure, with a new book out this fall that tells the story of how entrepreneurs bounce back from extreme adversity.

Melinda Wittstock:         Kelly welcome to Wings.

Kelly Fitzsimmons:          Thank you, glad to be here.

Melinda Wittstock:         I’m so excited to have you on. I mean, not only to celebrate your tremendous success as a serial entrepreneur, but also to dig deeper into this world of entrepreneurial failure, because most of us toil there, but the outside world doesn’t necessarily know it. You have a book coming out where you’re talking very openly about a lot of your own failure. Tell us a little bit about that.

Kelly Fitzsimmons:          Yeah, it’s part of the story that doesn’t get told often. We tend to hear and want to hear the stories of success. Those are the ones that we gravitate to, and it’s hard. Who really wants to hear the story of the poor jerk that had his IP stolen, and his startup shut down before he even started? Those stories don’t tend to make the news, so often our failure is in private and there’s this real high body count in entrepreneurship. The vast majority of our startups do not get funded. The vast majority of the funded startups, within three years, upwards of 92% of venture pack startups are out of business. Why?

Why do we go into this with such great optimism, and for me personally, what I found was the failure stories are really important, and we need to get ourselves out there and be willing to get tacky, and to tell it like it is, not our beautiful polished CV, or our wonderful brilliant bio, because it hides who we are, and it gives people a false sense of what entrepreneurship is really like, which is it’s a marathon, and it’s very, very difficult, and for every success we have, there’s so many failures. I decided to come out and really get public about my failures and what I learned from them.

Melinda Wittstock:         Interesting that you talk about the fact that we hide the failure as much as we can, because I think we look at other people’s success and the people who are successful make it look easy, but what’s missing from this story was all the gazillion times they failed, all the pivots, all the setbacks, all the everything that happened before they were an “overnight” success.

Kelly Fitzsimmons:          Success, right. Exactly, I mean you see this all the time. The 20-year overnight success story. The truth is the sausage making process is a sausage making process. It’s pretty gross and awful, and we hide that intuitively. I think women a little bit more so. There’s sort of a newer culture around failure that’s coming up in entrepreneurship around celebrating it, because it is a really important milestone of even getting venture capital that you have a solid failure under your belt, because nobody wants to invest in you unless you’ve already been through the mill, and there’s a good reason for it. You’re a lot more trustworthy, you have gone through something that breaks us, and if you survive on some level, it can’t help but make you a better person in some ways. That is if you pay attention to the lessons of it. It certainly can embitter us, and it does for a lot of people, but for me, I think my failures have actually contributed to my personal growth as a human being and I didn’t feel like that at the time. I certainly spent a lot of years licking my wounds and feeling sorry for myself, but now looking back on it, I am who I am much more because of my failures than my success.

Melinda Wittstock:         Oh my goodness, I couldn’t agree with you more. That’s so true for me as well. I mean, it’s so easy to get into this kind of victim mentality. On the kind of woe is me and it does feel icky when you’re going through it because you think, oh my goodness. You feel like you’re the only person that failed.

Kelly Fitzsimmons:          Yeah.

Melinda Wittstock:         Especially if you failed in isolation, and you’re not sharing and nobody else is sharing, so you feel like you’re the only person who’s messed up, and of course it’s not true, but when you stand back from it a bit, you think, oh my goodness. It was a lesson. It was a lesson. There’s a great saying that I love: It’s kind of like, “When the lesson is learned, the experience is no longer necessary.”

Kelly Fitzsimmons:          Yes, oh I love that. I haven’t heard that particular quote, but that resonates deep. That is so true for me. A lot of my embarrassment around failure was my inability to learn the first time. First time mistakes are forgivable, but repeated failure is really frowned on, like something’s wrong with you. Often, you have to do repeated mistakes, you have to go through the mill again and again to figure out what is the pattern that’s at work? Why do I keep showing up here? Women experience this all the time in dating. We keep showing with the wrong guy and he’s just wearing a different outfit.

Melinda Wittstock:         Right, there’s a pattern.

Kelly Fitzsimmons:          [crosstalk 00:26:01]

Melinda Wittstock:         There are all kinds of patterns in our lives, and this is true [crosstalk 00:26:05] as well.

Kelly Fitzsimmons:          Right exactly, and so this pattern doesn’t resolve itself until we wake up to it, and go through it. Then we stop falling into the metaphorical hole in the sidewalk. There’s a wonderful poem about this in terms of just, I’m walking down the street, I fall in a hole, I can’t get out, it takes me forever, but finally I crawl my way out. I walk down the street. I fall in a hole, and it keeps happening. Then finally I take another street. I’m not in a place where I’m on a different street. Some of those patterns for me are very recognizable and I’m looking to just really change how I approach myself as an entrepreneur, and to do so with kindness and love, which has never been my M.O., it was always self flagellation and self criticism, which ironically, there’s a great body of research today shows that actually is incredibly hurtful.

If you’re dieting and you fall off the wagon and you start beating yourself up about the chocolate cake, you’re going to eat more chocolate cake, because you have to comfort yourself now. If you’re kind to yourself and say, “Oops, chocolate cake just seemed like a great idea for breakfast”, you are much more likely to stick to the diet. Self kindness and, I found this through the work of Doctor Kelly McGonigal and her book. I believe it’s called Willpower. She has a lot of the research around this, and it’s very counterintuitive, particularly for high achieving women. We tend to be our worst enemies, very self critical, myself included, and so now I’m staring at a vision board that’s right over to the right of me and all over it, it’s got things to remind me to be kind to myself and to celebrate when I make a mistake, because it’s got gold in it. It’s where I’m going to learn. It’s where I’m going to grow, and it might not feel so great at the time, but in hindsight, it’s where all my best lessons have come from.

Melinda Wittstock:         Interesting that we are our own worse enemies. That bully voice that we have inside ourselves, and we all have this. We wouldn’t accept some stranger talking to us like that. Moreover, we wouldn’t talk to anybody else like that, so why do we do this to ourselves?

Kelly Fitzsimmons:          I think in part, this is my theory. I think it’s acculturated. Women are expected to be incredibly gifted when it comes to emotional intelligence. We are held to very high standards in our culture for intuiting things. For understanding the room, for understanding people and being able to meet them at their needs. If you hear in my voice a little trepidation, it’s because these are very difficult things to see when we’re in them. Worse yet, they’re really insidious, because they reinforce that we’re not first, that we are somewhere down the list in terms of importance. Everybody else’s needs in the room come before ours. When we break social code, say we approach the situation too masculine, or we’re too strong or perceived as too powerful, it’s often the women around us that are the first to tear us down.

Melinda Wittstock:         Ah, the crab pot. I heard someone describe this really well, that the reason why crab pots don’t need lids, is because when one is crawling out, the others bring it down. I think women have done that traditionally to each other for years. It’s the reason I started this podcast, to stop that exact phenomenon. We should all be lifting each other up, not pulling each other down.

Kelly Fitzsimmons:          Absolutely. It’s very subtle and not only do we do it to others, but we do it to ourselves. We are our own crab pot. That’s the hardest, ugliest piece of it. We don’t see how we do it to ourselves. We don’t see how we women are our own potential and how we drag ourselves down with unrelenting self criticism. One of the really corny things that I do, and this has actually been a game changer for me and it’s embarrassing to share, but when I feel my judge coming on, and it’s almost always around social situations, boy did I just blow that interview with Melinda. I’m sure I’ll do that afterwards.

Melinda Wittstock:         We all do that right?

Kelly Fitzsimmons:          Right? We all do it. I’m going to be, oh my God, I can’t believe I said that. I actually say out loud, “I love me. Oh my gosh, I love me.” I have to just kind of yell over the voice in my head that wants to tell me how awful I was to reinforce self love, because for entrepreneurship, it really comes down to self belief. We have to believe that we’re this unique creature that’s capable of doing magic. We’re able to bring new things that don’t exist into reality. That self belief is a critical component of the magic that we do. Yet, it’s very easy to lose our self belief through self criticism. For the last, oh my gosh, I’d say five years, I’ve used the, I love me technique, to catch myself when I become self critical and I go into this reflexive mode and over judge myself in terms of my social interactions.

It’s been really helpful. Has it solved it? No, but my judge is a lot quieter. She doesn’t show up like she used to, and so it’s given me some freedom to be able to take more social risk, which is another thing that’s required, and also I think hold women back a lot, is the social risk and being seen as disagreeable or unlikeable. When we are teaming in self belief, we’re more likely to step out there, which is where we need to be as entrepreneurs often.

Melinda Wittstock:         Beautifully said. I want to go back to this conversation about failure and de-stigmatize it. Do you mind sharing Kelly, a specific experience of failure that you went through in one of your companies, because I know that you have overcome tremendous things.

Kelly Fitzsimmons:          Yeah, so if you look at my bio, you’ll see six startups. Five of those are still in business, which is shocking to me.

Melinda Wittstock:         That’s amazing. I mean, that is astonishing, and also you’ve had exits and groundbreaking technology, kind of almost to the point of seizing a category with HarQen. I mean, with all the voice recognition, you are so ahead of the game on that. You have so many accomplishments, so it’s hard for me. I look at you and I think, I never thought that you had failed at anything. Okay?

Kelly Fitzsimmons:          [crosstalk 00:33:04] oh yeah.

Melinda Wittstock:         Oh my God, like you’re my hero.

Kelly Fitzsimmons:          No, well thank you and it also tells me I need to do a better job of outing myself. I need to, and I try really hard to do this, is not let anybody walk away from a conversation with me thinking that I am somehow superior on any level. I always want to show my soft underbelly because that’s really who I am. My big failure, I’ve had so many, but the one that went out of business. I was 29. It was a company called PRISM, Proactive Remote Information Security Monitoring. I started this in 1998, to give you a sense of that, in 1998, seven hackers went before Congress and testified that they could take down the internet in 30 minutes, the entire internet in 30 minutes, and Congress didn’t do anything. Nothing happened.

Melinda Wittstock:         Sounds familiar. Same old, same old.

Kelly Fitzsimmons:          Right, so the Washington Post would later put this as a tragedy of missed opportunity as we’re looking at identity theft and various malware and cyber attacks, and cyber warfare. The craziness that’s going on today. This all kind of actually been prevented if somebody had just listened to these seven people, but it didn’t happen. That same year, I founded PRISM to do remote information security monitoring of large enterprise companies. I got venture debt, and bank debt. Back then, you could get bank debt. The dot.com crash happened two and a half years later, and I had never been through a downturn. I had never seen a crash. I had no, I mean it was, again, an error of inductive reasoning. I had never experienced this,.

Like the turkey on the Wednesday before Thanksgiving, I was in for quite a shock just because the farmer rescues the turkey, doesn’t mean that the farmer’s actually friendly. That’s the same thing that’s true with markets. They do reverse. They do fall out from underneath you. I found myself personally guaranteed on the hook for $5 Million, and it still, as I say it, I can feel the nausea coming up.

Melinda Wittstock:         Coming right, like the, personally guaranteed for $5 Million. Everybody just think about that. How would you feel with that? Right, okay, so there you are …

Kelly Fitzsimmons:          [crosstalk 00:35:32] the 29. I had a condo at the time, and I had some equity in the condo, so I’m going to just go out on a whim and say, maybe it was like $250,000 in equity. I doubt it was that high. I did not have that money. I had been in such a mindset, that of course we couldn’t fail, that I’ll happily sign these guarantees. Never for a second thinking I couldn’t back it up. Oh boy, could I not back it up. The good news was half of that guarantee was through provisions in the contract on the venture debt, that our partner ended up walking away from, but the two and a half million was banked and that was owed, and that had to be paid.

Over the course of the next three years, that was the burden on my back. I will not lie. I was depressed. I had merged a company that I still had, Sun Tzu Security, into a company down in Chicago called Neohapsis, and I was now CEO of this combined company, and I was struggling. I was struggling really badly and I interviewed a friend, a colleague who worked with me back then. She’s like, “I had no idea. I had no idea”, and she was like the closest one to me, what the burden was on my back.

I was suicidal. I really was. I had fantasies about figuring out how to have insurance pay this off, and that I could just disappear into the ether and my debt would be paid. It was really scary. It was really scary to be in that place and to be so bifurcated. I still had my game face on. People closest to me at work had no idea how sick I was, but in three years, we ended up, actually within four, we ended up selling that company and I was able to pay off my debt and have money left over to start HarQen. I ended up starting that company 30 days after that transaction happened. That tells you a lot about where my mental state was, and how off I was.

Melinda Wittstock:         Oh my goodness. You’d also suffered as a woman going out on her own to raise venture capital.

Kelly Fitzsimmons:          Yeah. Yeah, so when Nina Burleigh wrote her article for Newsweek several years ago, I think it was 2015, Tech Has a Sex Problem, I was behind the scenes and helping her source people. I knew so many stories, because I had shared my story in certain circles with other women about how when I was 29 and I was trying to raise venture capital funds for Prism. I was physically attacked by one of my closest advisors and long term mentors. He was 70 years old, I mean I never saw that shit coming.

Melinda Wittstock:         Oh my God.

Kelly Fitzsimmons:          Yeah, I mean I felt totally safe. He’s like my grandfather, and yeah, no, he didn’t think that. I was so devastated by that experience, that I called off the fundraise. I couldn’t actually raise more funds. If I had been able to at that time, I could have saved Prism. I could have saved myself that real heartache. We didn’t have big customers. That’s a whole other story. The key customer at Prism was a Fortune 500 that failed to pay me for 120 days. That was kind of par for the course of this particular company. Yeah, it was a perfect storm.

Melinda Wittstock:         You know, it often is. That’s the strangest thing. It’s not just one thing. It’s a number of different things, and some of them are just beyond our control.

Kelly Fitzsimmons:          Mm-hmm (affirmative), yeah. [crosstalk 00:39:49]

Melinda Wittstock:         It’s all [crosstalk 00:39:49].

Kelly Fitzsimmons:          Yeah, and also one of the things that we have to recognize is that just because something has never happened to us in the past, doesn’t mean it’s not going to happen in the future. We really discount that, and the likelihood of being surprised like that and then we take what we feel are calculated smart risks, but they’re not, because we don’t have the experience. Conversely, that’s also one of the up sides for women entrepreneurs. We tend to get in the game very late. We tend to feel like we have to prove ourselves in corporate America first. We don’t even show up to the party until our late 30’s or even 40’s to become an entrepreneur. In some ways, that’s really helpful. It’s not helpful when it comes to raising venture capital. We certainly don’t, we run into even more issues in terms of sexism when it comes to raising funds, it’s very hard, even for men over 40 to raise funds for a venture startup. The women that do show up have a lot of experience and have been surprised, and have gone through hard things, so that they’re better suited in a lot of ways to be an entrepreneur.

Melinda Wittstock:         Oh gosh, it’s so true. I’ve noticed this, that we don’t really fit the pattern. VC’s always talk about investing based on pattern recognition, and so the pattern that they recognize is a dude in his 20s with a bunch of other dudes all in hoodies and sneakers in their garages, and they’ve all dropped out of MIT, Harvard or Stamford, and they eat Ramen noodles. There are too many carbs, right?

Kelly Fitzsimmons:          [inaudible 00:41:34] and MSG, who does that?

Melinda Wittstock:         I know, right? We tend to come into our own in terms of startups from 35 on. In fact, really the sweet spot is in our 40s.

Kelly Fitzsimmons:          Right.

Melinda Wittstock:         Whether we just have a lot more confidence then, but then we’ve also, you don’t fit the VC paradigm, because we’ve already hired and fired and done things. We have expertise, we have domain expertise, so it’s harder for a VC to put that kind of, I don’t know, perhaps they perceive that we can’t be controlled. It doesn’t really fit their business model.

Kelly Fitzsimmons:          Right, there’s a lot to that. I mean, the male 20-something is also in a really precarious position. They look and they see Mark Zuckerberg, or Larry And Sergei, or whatnot, and they think, I will be the CEO of my company until it’s a billion dollars or more. What they don’t see, again survivor bias, all of the young 20-somethings, that as soon as the company shows any promise, get thrown out of their own company and replace with somebody who actually knows what they’re doing. That is a very typical founder story. That is not part of the mythos of startuplandia. When people look at the landscape, they really discount the likelihood that they will be with their startup when it reaches success.

Women, conversely, we do tend to stay in control of our startup, and we do tend to have much better survival rates. Springboard, which we both are involved with, has been studying this now for over 16 years, and of the start up companies that have gone through Springboard, I might be a little bit off on this, but I believe our survival rate is over 80%.

Melinda Wittstock:         Yeah, that’s really interesting too, because it bears out, even on Nasdaq data, that companies that have women in the executive team and on the board in insignificant enough numbers wildly outperform by any metric. Earnings, revenue, growth, survival. Female run companies are more likely to survive, and yet it’s so interesting that VC’s really ignore this.

It seems like it’s a broken model, so for women starting out, assuming that they have a company that actually qualifies for VC funding. In other words, it has the ability to scale. It has some sort of disruptive, the innovation about it. Something that’s going to change behavior; in other words, something that’s going to be $100 million, $500 million, or a potential Billion-dollar company. That interest of VC. Of those women, what is your best advice for women that need funding, and are there alternative routes to avoid putting yourself through these, well not only what you went through Kelly, oh my goodness, but to actually even get the money.

Kelly Fitzsimmons:          Yeah, so the good news is that there are investors that have woken up to the fact that from a statics pure data standpoint, women with startups tend to be more successful and tend to have better survivability. For instance, I’m a limited partner in a venture fund called Bell USA, and Bell USA exclusively funds women led startups in technology.

I love paying it forward and I love being involved with a fund that walks that walk. Not just because it’s socially right, but because it’s an awesome opportunity when there is a cultural bias that blinds people to the facts, the stark naked reality that the data points out that women, and we tend to be 35 and up that are running these startups, have a better survivability rate, and have had some massive exits. I mean, in Springboard, we’ve had, I think nine IPOs now. Constant Contact, iRobot, Zipcar. We’re all Springboard companies, and that kind of success is really remarkable and something worth investing in. If the rest of the world is so stuck in their pattern recognition of white dude from MIT in their basement, well thank God there are smart investors out there who get it and are willing to write checks.

Melinda Wittstock:         Yes, and I love Springboard. We were in the same class of 2011 and it’s interesting what you say about Bell USA. Of course, Lauren Flanagan, the founder, she was on this podcast and everybody go and listen to Lauren’s episode, and of course Kay Koplovitz, who founded Springboard. I think she was like episode seven of Wings.

Kelly Fitzsimmons:          Oh good, [crosstalk 00:46:49].

Melinda Wittstock:         You go back and find both Kay and Lauren. There are so many funds all of a sudden now. You think of Aileen with Cowboy Ventures, you think of the stuff going on at Ellevest, Female Founders Fund. They just got a second fund. Oh my goodness, there’s so many all of a sudden. Pipeline Angels. I’m a big believer in intentional living. Setting intentions and feeling them as if they’ve already happened. One of mine is really Big Moonshot, where I just decided I wanted to be the change that I wanted to see in the world, and over the next 10 years, I want to invest 10, no, I will not, I want to. I will invest $10 Million in female founded startups.

The more of us that just set that intention and pay it forward, and that investment can take many shapes. I mean, cash is obviously necessary, but also doing this kind of thing. Really paying it forward, mentoring other women, being there for them, really helping. Throwing business to each other.

Kelly Fitzsimmons:          Right. I mean revenue. Revenue is everything, and it’s incredibly important to be generous. This is the thing where I think women do it well by and large. There was a generational thing where early on there were so few seats at the table, that if we made it through, if we broke through the glass ceiling, we defended our seat. That’s really shifted. It’s not gone. It’s still there. I certainly know too many women that defend the seat at the table, but there’s more of us that really do want to pay it forward, like you said, and invest in each other. One of the best ways to do it is referrals and revenue, and just talking about each other and telling your stories. One very practical tip that I can give, is I’m good at media relationships. It’s just something that came naturally to me, and so very early one, I would cultivate these relationships, not by calling up the local reporters and talking about me, because who wants to hear somebody do that? I talked up everybody else’s startup.

I’d call in whenever I heard a great story, particularly about a female entrepreneur. I’d call in and be like, “Hey, have you talked to so-and-so? I knew that there were reports were looking to represent more women and minorities, and so they needed to know who these people were. I was a trusted source and so I would do that. Sometimes, something as little as an article can make a company’s success, a single customer reads it, shows up at the door and they become one of their top 10 accounts. That’s magic, and it’s a simple, easy five-minute thing to do.

Melinda Wittstock:         What a beautiful thing to do. I think we should all just do that. I’m going to start doing that. I mean, I kind of do that with the podcasts in a way, but why not, because those sort of earned media articles. Also, you know what’s so interesting Kelly? We talk a lot on this podcast about sales and asking of the sale and why that can be so difficult sometimes for women, and I want to get into that a little bit with you in a second, but you know what’s easy for us? It’s easy for us to sell somebody else’s thing. It’s much easier than it is to sell our own, so if we all get together and do that for each other as a true game changer.

Kelly Fitzsimmons:          It is. It’s so easy and it’s magic. If you need a selfish reason to think of it and just to do it, you look like a better person for it. When the media wants to talk to you, you’re going to be the first person they think of. I didn’t do it for those reasons, but I really benefited from it. It’s unfortunate that we have to think about what’s in it for me, but a lot of people do, so that’s what’s in it for you.

Melinda Wittstock:         I just think, at the end of the day, if you’re creating value for other people, you will be increasing your own value.

Kelly Fitzsimmons:          Absolutely, it’s karma. What goes around comes around. Either you can put good out into the world, or you don’t. I think for me, what I’ve learned the hard way, is whenever I’m not walking my walk, being my own worse critic really stinks, and so I know it, and I see me in the mirror, and I just can’t stand what’s being reflected back. Conversely, when I do something nice or help somebody out, I really love this reflective back in the mirror to me. It really helps build my self belief, which like I said before, is a critical part of being successful, because you need those reserves on a day when everybody’s doubting you.

Melinda Wittstock:         Gosh, this is so true. One of the things that women fall into a lot is perfectionism.

Kelly Fitzsimmons:          Oh yeah.

Melinda Wittstock:         It’s kind of the sister of this bully voice that we have. We think that we have to have everything perfect, and it stops us sometimes from asking for help. It’s like cleaning your house before the cleaners come.

Kelly Fitzsimmons:          Oh for sure. There’s so many aspects of it, and it’s really hard to see if you’re doing it, because it’s our armor. Perfectionism is like donning our armor to walk into the arena and do battle. If we’re perfect, our belief system is that we will come out intact. We will prevail. The thing that we don’t notice is that that armor weighs us down. It actually makes it very hard for us to fight the good fight, and we’re walking into an arena where most of the time we’re set up to fail.

The perfectionism trap, and it really is a trap, keeps a lot of women from ever becoming entrepreneurs. That would be so great if they just came over to our side of the party, got out of corporate America, stopped beating their head against the wall, and the real trap is perfectionism. It starts early. It starts in school. We’re graduating at much higher rates than men from high school and college and earning professional degrees. In that context, it’s a meritocracy. Our perfectionism is rewarded again, and again, and again, and so it falls into the air of inductive reasoning. What we’ve done in the past, which was really polish yourselves, and really put ourselves out there in this perfected way absolutely sabotages any possible chance that we have of success when we get out into the arena of life, because perfectionism is not rewarded. Speed a lot of times is rewarded. Calculated risks are a lot of times rewarded. It’s not perfectionism and quite frankly, it’s a false notion. It’s an absolute false notion because what we might perceive as perfect, other people might perceive as whatever. It’s not …

Melinda Wittstock:         Also, there’s a big difference between perfectionism and mastery.

Kelly Fitzsimmons:          Correct. It’s not the same thing.

Melinda Wittstock:         It’s not the same thing, but it gets confused all the time.

Kelly Fitzsimmons:          Well, and this goes back to the work of Carol Dweck, and I don’t know if you ever read her book, Mindset, but she wrote it in 1990’s and in it she really broke through some new ground about why certain people succeed, and why people fail. Her conjecture, which she backed up with a ton of research, had to do with our orientation on a very, very basic thing. Did we see our intelligence and talents as fixed traits, or were we able to grow? A growth mindset sees everything that we come through as an opportunity to learn, and it came from her studying of these kindergartners where she was trying to study failure, and she kept giving them increasingly hard problems and puzzles. Eventually, she kids would break down in tears and they’re like, “It’s so [inaudible 00:54:52]”, and she would study their failure. There is these weird kids that didn’t do that. These weird kids that would be like, “Oh my gosh. This is the best puzzle ever. Can I take it home and work on it over the weekend?” What’s wrong with you?

Those kids over time in a longitudinal study turned out to be so much more successful. It’s not rocket science to see why. They’re constantly able to learn. They’re willing to be beginners. They’re willing to get messy. They don’t see failure as a problem per se. Unfortunately, perfectionism is a fixed mindset. We believe that our talents are finite, so we have to perfect them, so that we can go forth in the world and win, and it’s a zero sum game. Mastery is a growth mindset. Mastery is about learning and loving the love of the game, so my husband Jeff is extraordinary at this. I’ve never seen any human being do this, but he can teach himself anything. By anything, I mean anything.

We were doing virtual reality and I look over and I see him doing all this crazy math, and this is back in 2013. I’m like, “Is that calculus?” He’s like, “Yeah.” I’m like, “Why are you doing it?” He’s like, “I’m calculating parallax errors.” I’m like, “Really? What? Just for fun?” Yeah, I mean he pulled out calculus, retaught himself it so he can solve these problems. The likelihood that I would do that is very, very little, because I do tend to fall back into a fixed mindset and I get really freaked out sometimes being a beginner again, because it’s messy and I don’t want people to see me as, “Oh my gosh. She doesn’t know calculus? She can’t just pull it out?” I have to self check, so perfectionism leads to this very, very stuck place, where we become narrow and brittle experts in a very small place, versus being wide ranging, more Renaissance poly mask, where we’re interested in a ton of things and we’re constantly learning.

You can see how that basic identity, whether or not we see our talents as fixed, and we just have to perfect them and get them to the best, versus my talents can grow and change, and my intelligence is whatever I stick myself to and I have this open mindset and growth mindset. Yeah, I want to be like Jeff. I want to be like, “Hey sure, I can learn calculus. That sounds awesome. Let me go do that.” I’m not there yet. The perfectionist, it runs pretty deep in me.

Melinda Wittstock:         Even the doing, like we don’t necessarily have to do it all to have it all, right? What I think is interesting is the perfectionism sometimes gets in the way of us asking for help or delegating, or right?

Kelly Fitzsimmons:          It gets in the way of everything. If we really look at it clinically and we try to step outside ourselves, or have the courage to ask others around us to point it out to us, which is a much better lens, because this is the water we swim in. We can’t necessarily see how cumbersome and how weighted down we are by perfectionism. There is so much to be learned. I do get quiet. I hide my failures because that comes out of my fixed mindset. It comes out of my perfectionism. I don’t want to be seen as messy there’s a whole part of my psychology that just bristles at the idea, and part of going out and being the poster child for failure in my book is really stepping into this uncomfortable place for me, and saying, “No, no. I can do it. I’m willing to be messy. I’m willing to share my failures and grow as a person.” That is not a natural tendency and I do also fall into the trap of not asking for help or communicating when I need it.

Melinda Wittstock:         Oh gosh, like you and I, like we’re twins. [crosstalk 00:58:54] ’cause I know, seriously.

Kelly Fitzsimmons:          [crosstalk 00:58:54] that we met.

Melinda Wittstock:         This is a life long challenge for me as well, and the more I do these interviews, and the more I get to know these amazingly successful women, all of us in our own way, we all struggle with this to varying degrees.

Kelly Fitzsimmons:          There’s one piece that’s really practical here. We talk about it, but we can’t really change it when we’re in it. There is something that we can change and it’s our language. To keep ourselves out of the trap of perfectionism, it’s very important that we talk differently to ourselves, and a very simple thing we can do is add the words, not yet. I don’t know calculus, yet. I couldn’t do that up until now. You give yourself room and you change your language consciously to create space for learning and growth. Perfectionism is the enemy to learning and growth. It is absolutely the enemy, and it keeps us so, so small.

Shifting our language, and this is again from the work of Carol Dweck, changes everything. Coach used to say to me, up until now. Every time I’d be like, “I am so bad at this.” “Up until now.” That’s right. Up until now, I suck at this, but I’m going to get so much better because I’m willing to become a beginner. Becoming a beginner and perfectionism are in different sides of the teeter totter, so we have to, have to really get at the root cause of it, and the root cause is how we choose to see ourselves as either a person who is capable of growing and learning, or a person who’s got to perfect these set traits, these set talents. We have to use it as much as possible, and this is really a generational thing too Melinda, so we were born in a day and age before neuroplasticity. We weren’t taught this in high school and college. We were taught that if you had a brain injury, you were screwed.

With me with dyslexia, I was told, “Well, that’s just how it is.” I couldn’t figure out why I learned to read. That shouldn’t happen if I can’t fix it. I do hope, my hope for future generations that know about neuroplasticity, know that yeah, the brain changes who are not set in our traits. The problem is it can be intellectual, but if we just keep the intellectual and we don’t do the hard work of changing language, changing self dialogue and also putting ourselves out there and testing things, and failing, we’re going to always be trapped in the tiniest tiny box of perfectionism that’s just ultimately going to suffocate us.

Melinda Wittstock:         This is so true. Kelly, I wasn’t to ask you about being a technology entrepreneur. This is tricky for women, because it can be tricky to change the culture or the bro culture. You got to hire people, engineers and codes, and developers, and so many of them are men. What are some of the challenges that you’ve found in managing them, hiring them, managing them and coming at this as a technology, because I think there are a lot of women who are so suited for this, but somehow tell themselves, or get told that that’s too hard a business, and they go do something else in marketing or something, rather than technology.

Kelly Fitzsimmons:          [crosstalk 01:02:28] marketing tech. Yeah, I mean we’re HR [crosstalk 01:02:31].

Melinda Wittstock:         Yeah marketing and HR, yeah exactly.

Kelly Fitzsimmons:          Yeah, so these are women ghettos, and we fall into it all the time. I have to fight it because it’s so … My actual talents, my genius is in marketing and PR, and so I would have been an incredible PR chick, but because I started when I was 11, and I loved technology, I gravitated that way, but I also gravitated that way out of ego. I didn’t want to be one of many. I wanted to be special and going into Information Security in 1996, I was practically alone as a female. When I look at it, for me, what have I learned? You got to play to your strengths and you got to know what your strengths are, and most of us are really kind of crappy at knowing what our strengths are. We discount them. One of my strengths for instance is positivity. I found this out through the Clifton strength finder test, which I highly recommend that everybody take. It’s through Gallup Poll International.

There’s basically 34 different ways we perceive information. We have a top set of five traits, that if we really give time and attention to strengthening these, we can get to a place of a real mastery, and the stuff that’s at the bottom, which for me is analytical of all things, if we try to play there, we can hope for mediocre at best. When I got my strengths back and I saw positivity at the top of the list, I cried. I was so, so sad that I wasn’t analytical, because I really felt like I needed that in technology. What I learned over time is that I have a lot of skills in terms of emotional awareness and emotional intelligence, and I’m really good at elements of communication, not all, but certain and I was a great interface for our very deeply technical team, many of whom were on Spectrum. They had Asperger’s and they did not feel comfortable with even eye contact, so putting them in front of a customer was too much.

I became the gooey, and I was able to celebrate that role over time. In the beginning, I wished I was them, but as the lights went on over time and my self belief grew, I realized that my real giftedness to this is as a translator. I can take their expertise, their insights, their brilliance and share it with the world, which to a point you made earlier Melinda, it’s something women do very naturally. We can talk about our team so well, but as you probably remember from Springboard, when it comes to talking about ourselves and how awesome we are, we completely fall apart.

Still, I’ve used that to my advantage in technology, and I’ve also, another thing that I have learned, and this is more recently, is you can have a diverse talent pool. A lot of us in technology be like, “There aren’t out there. There’s no women. I can’t find any minorities, and we’re actively searching. I did this at Neohapsis, I really wanted to have more diversity and ended up with one African American guy, and one gal on my team and it was heartbreaking. My current startup, my partner Brad has been doing this for years, and he’s like, “Yeah, you can’t expect them to be there. You got to train them.

In our current company, our mission is to be almost exclusively hiring women and people of color, and teaching them the tools of BR. Our first hire, Maddy, is not a producer and she’s leading the Facebook forum on women in BR. She’s 25. She’s a total rock star, but she was an investigative journalism major in college, and she learned on the job. It is totally possible, you just have to be willing to do the hard work to create that kind of diversity.

Melinda Wittstock:         That’s so interesting. One of my earlier companies, I hired entirely interns. I was changing and upending a business model in journalism that required complete teamwork, and so the only way, this was Capital News Connection, it was before NewsiT, and the only way I could really do this, was to hire people that didn’t have the old habits.

Kelly Fitzsimmons:          Right, exactly.

Melinda Wittstock:         I hired interns and trained them, and like honestly, one of them is now Katie Couric’s producer. One of them is the executive producer of Face the Nation. Another one … You know. They all learned on the job, and it was a great way to do it and not least of which when you’re in a scrappy startup and you don’t have a lot of money at the beginning, it’s a great, great way to go. I love what you’re doing with women and minorities and tech, because creating those cultures where women feel comfortable really being the badness. There’s so much talent out there, so thank you for doing that. I think that’s awesome. I could hae you on again to geek out about all things AR and VR, because that’s such an exciting space. Tell us really briefly what you’re working on with your current company.

Kelly Fitzsimmons:          Yeah, so our current company, we are in virtual reality. We’re a virtual reality production company, and we have about six projects currently going. One of the ones that I’m most excited about is around implicit bias and working with police departments and community organizations to help address implicit bias via virtual reality. Showing things from an alternative perspective, so that we can see how we look through other people’s eyes.

Melinda Wittstock:         Oh my goodness. I’ve got goose bumps. That’s awesome.

Kelly Fitzsimmons:          Yeah, and one of the beautiful things about being in this point of my career, is we get to really choose what we work on. Another one that I’m really excited about is the story of Arthur Ash. It’s the 50th anniversary of his iconic win at the U.S. Open, which made Arthur, Arthur. Today, that stadium is Arthur Ash Stadium, yet there’s a disconnect between the younger generation who really don’t know Arthur, and who he is and as a black champion. Also as a protester, and somebody who put himself out there. Very strong parallels to what’s happening today. Looking at him through, what was it like to be a champion in 1968 in tennis, and allowing people go to back in time and to see the world through Arthur’s eyes as much as we can. That’s another project near and dear to my heart.

We’ve got a lot going on. For me, my number one priority is to keep pushing us creatively to try and do new things that we don’t, even though we’re working in social justice, keep coming at it the same way. There’s so many stories that need to be told, and the audience needs to be the non-traditional audience. Like if they already believe and are excited about the stories we’re telling, we’re preaching to the choir, so how do we get people who don’t know these stories, or may actively kind of be angry about these stories and feel like activism and sports shouldn’t go together. How do we get them to be curious to see our stuff? That’s really the edge of the work that we’re doing, is trying to figure out how to create more conversation and reduce the polarity that we’re seeing out there.

Melinda Wittstock:         How wonderful. Very inspiring. I can hardly wait to read your book, tell us just a little bit about it, and when it’s out and how people can get it.

Kelly Fitzsimmons:          Yeah, so it will be out in all the normal channels. It is coming out in October. It’s called Lost in Startuplandia: Way Finding for the Weary Entrepreneur. It’s designed to be a field guide for when you’re experiencing failure in your startup. It doesn’t have to be cataclysmic failure, it might just be the first time you hit a bump, or it could be you are completely at a crossroads and don’t know what to do. The book is a combination of my story, with several friends who have experienced some very traumatic upheaval in entrepreneurship, and it’s there to help guide you, but also point out that there is no map. That the train changes all the time, and what worked for one, will not work for you, but that there are some surefire ways to fail.

Whether it’s taking care of yourself, or managing your relationships, or most importantly, really getting smart about how you decision. How do you make decisions and what you focus on, and trying to be very, very practical and grounded on things that we’ve learned the hard way about what works and what doesn’t work when it comes to those domains.

Melinda Wittstock:         I can hardly wait to read it. Kelly, what a beautiful interview, and thank you so much for just showing up so openly and authentically, and in sharing your success and also your failure, because all of that just helps pay it forward to some many female entrepreneurs coming up. Thank you very much for putting on your wings today and flying with us.

Kelly Fitzsimmons:          Thank you so much Melinda.

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