170 MINISODE #MeToo, #VCs and Leveraging #Failure: 4X Serial Technology Entrepreneur Kelly Fitzsimmons Advises on Raising Money and Avoiding Isolation

Kelly Fitzsimmons is a 4X serial entrepreneur and pioneer in voice recognition technollgy and cyber security software with several 8 and 9 figure businesses and exits to her name. She shares important advice for women in tech seeking funding, inspired by her own harrowing #MeToo attack by an investor which sent her into depression, isolation, shame – and now recovery with a new virtual reality company and a new book out this fall.

Melinda Wittstock:         Welcome to Wings Kelly.

Kelly Fitzsimmons:          Oh, thank you Melinda. Happy to be here.

Melinda Wittstock:         I’m so excited to talk to you and I always love to start these Friday minisodes with that is inspiring you most right now?

Kelly Fitzsimmons:          What a great question. I have the blessing of going back over a series of interviews that I’ve conducted over the last two years of very successful entrepreneurs, many of whom are friends of mine, and re-listening to their experiences around failure. Some of these failures were so public and so painful. I’m so inspired by them and their ability to carry on. Not just move past it, but in two of these stories, really come out on top. For me, they’re gold. There’s just so much gold in their wisdom on coming out on the other side. That’s what’s inspiring me right now.

Melinda Wittstock:         That’s so wonderful. I mean, what a great segue into challenges, because as entrepreneurs, we all contend with failure. It’s part of the process.

Kelly Fitzsimmons:          Right, it is. Failure, we talk about it in such abstract terms, but it’s a very concrete thing and it’s at the root of so many of our phobias and fears, and for a lot of folks, the reasons why they might go into entrepreneurship. They might choose what they see as a safe corporate job. Entrepreneurship is all about going from one failure to the next, and to badly quote Winston Churchill, with increasing enthusiasm.

Melinda Wittstock:         I love that.

Kelly Fitzsimmons:          It’s true. Our ability to weather those storms and take the lessons learned really provides us a crucible for personal development. If we’re doing it right, at least in my opinion, we come out on the other side as better people. There’s nothing quite like the mirror of failure to break through some of our most resistant and difficult to see blind spots, and/or discover the patterns that we run when we’re in survival mode that really harm us. That they’re vestiges of childhood that aren’t serving us well, and they’re very hard to see unless we’re in the thick of it and willing to look and say, “What could I do better?” Failure for me is my greatest teacher, and although it’s one of the most painful and unforgiving teachers, it has proven to be an exceptional guide for me.

Melinda Wittstock:         Yeah, it’s almost like entrepreneurship is extreme therapy.

Kelly Fitzsimmons:          I love that. It is. It is, because if you don’t want to look at the hard stuff, you’re doomed to repeat it over and over, and if you’re in this for any period of time and you refuse to grow as a person, you’re going to be out, sick or dead within 20 years. There’s just no other outcome. It’s just too painful.

Melinda Wittstock:         Gosh, this is really true. What’s a big challenge for you right now, because all of us, we always have challenges and I like to de-stigmatize failure, but also de-stigmatize challenge. If we talk openly about these things, it kind of gives permission for other people to do the same, so what’s a challenge for you right now?

Kelly Fitzsimmons:          I have dyslexia, and this is a life long challenge. In eighth grade, I was not able to read and my tutor at the time, exasperated as she was, told my mother, “I don’t think Kelly’s every going to learn how to read.” That wasn’t true. I started reading in college. I was 20 when it turned on, and about two years ago, I lost my ability to read again. I didn’t know that could happen, and it was one of those very startling things that comes up in life in which you’re not only surprised, but you have to rearrange everything because of it.

I had to step off all my boards. I had to take a sabbatical from work. My reading ability I discovered was at the core of not just the things that I did during the day, but it was very much tied to my identity. It really set off into motion a series of very deep emotional crises around my desire to be seen as smart and capable, and this inability to read, and so how do I reconcile the two? That was really what set me off on the journey in the last couple years.

Melinda Wittstock:         Kelly, how inspiring though, because of all of your success, to overcome something like that. To succeed as a serial entrepreneur is truly inspiring. I want to turn now to this part of the minisode where we talk about your top three go-to pieces of advice. Joined from all that you’ve learned through all these startups that you’ve done, what would you say are the top three for women in business and women in entrepreneurship?

Kelly Fitzsimmons:          The very first piece of advice I have is if you are out and raising venture capital, never go it alone. It’s a very practical piece of advice, and unfortunately something I had to learn through my own experience, but sexism does run deep, and these are power relationships that can go sideways very quickly. Unfortunately, as many people learned a couple years ago with Nina Burleigh’s article on Newsweek. Her cover article on Tech Has a Sex Problem. Raising venture capital really puts you in this weird precarious position as a woman, and unfortunately, there is plenty of men out there that are willing to take advantage of that and me personally, I was physically attacked and it really did a number on my self-esteem, my self belief, the things that are critical to succeeding in a fundraise.

In that particular case, I ended up ending the fundraise and that company failed, and I was 29 at the time. When it failed, I had personal guarantees totally $5 Million, and I could not see my way out of it. I spiraled into a real depression. It took me about six years to recover fully from that episode, not just the fact that I kept running into and having to work with the person who did it, but worse yet, I had this incredible financial burden that I was carrying on my back that no one, almost no one, knew about. I’m very grateful that I was able to have enough success in business that that was wiped out, and I was able to get more proceeds. That’s what I used to fund Harkin, but it really tripped me up. Number one, never go into a fundraising situation in which you are alone, and don’t accept casual “dates”, such as, “Let’s go grab a drink” or those kind of things. If you do, bring somebody with you from your team. It’s critical.

Melinda Wittstock:         Oh my goodness. It just … My heart stopped listening to you there. What you endured, and just the knock on effects of all of that and then soldiering through that alone. My goodness, I mean …

Kelly Fitzsimmons:          It’s one of the things, and there’s going to be inevitable backlash on the Me Too movement and we’re already seeing it, but unfortunately so many of us have experienced this and up until very recently, none of us talked about it and none of us shared what happened. We got to be careful about over celebrating victim culture. It doesn’t help anybody, but there is strength in talking about it, sharing our experiences, and learning how to get through it. So often, it is breaking the stigma that you did something wrong, or that this is not an acculturated problem, the problem is you. That is not true. This is a culture problem.

Melinda Wittstock:         The practical tip: don’t go alone. Go to the office, all of that, so, so important. What is tip number two?

Kelly Fitzsimmons:          Tip number two is to verify trust, but verify your instinct. This has to do with market validation, so if you’re going out to raise venture capital, women are already in a precarious position. There is over two million businesses started every year. Only 600 to a max 800 receive venture capital. Last year, 2% of them were led by women. We’re talking a max of 16 companies that were funded by women and the CEO chair. This is a real problem, so when we go in, we really have to know our stuff, and market validation is the one piece that is really easy to trip up, because so often we tend to be optimists. We’re going at this because we believe in this future that we see, and it leads to confirmation bias, and so we only see the data that support our hypotheses. We end up getting overly enthusiastic, and discounting unfavorable data that we might be receiving.

I’ve certainly survived confirmation bias. I’ve certainly been able to pull into reality futures that I believed in, but at the same time, it hurt me too when those futures didn’t manifest as quickly and/or in the manner that I thought they were. It’s critical, and it’s a newer skill for me, but I’m constantly course correcting, double-checking my data, checking myself for confirmation bias. The best way I do this is through having a dark cloud. A friend who’s a truth teller. Somebody who really understands the market, the business. Who’s willing to call me to the carpet if I’m getting too many feet off the ground in terms of my optimism.

Melinda Wittstock:         Oh, that is such profound advice and honestly Kelly, I’ve been there with you, big time [crosstalk 00:11:12] confirmation bias, and [crosstalk 00:11:14] one of the most, oh my God, and one of the most interesting moments I had the opportunity to learn from Tom Chi at Google X about rapid prototyping, like with your customers right away, and really getting customer validation at the earliest point. Even if you’re just prototyping with post it notes, talk to your customers then. Don’t wait, and I think a lot of women in particular, I mean we’re a little bit shy sometimes about asking for help, or asking customers. Being willing to accept the no, but the no is kind of what you need to hear and so it’s tricky, so how to balance all of that. What profound advice, and then I guess we’ll segue to advice tip number three.

Kelly Fitzsimmons:          Yeah, so this really builds on the first one, but self care needs to be our number one priority. This I had to learn really the hard way. If we don’t take care of us, we’re not capable of taking care of our startups. We become our biggest risk factor. Startuplandia is a marathon, and the older we get, the crazier the impact that high continuous stress can have on our body. Stuff will and can go wrong, and we often get so caught off guard by it, particularly as women. We reach for our adrenals that have always been our faithful friend, and suddenly we put the pedal to gas and there’s nothing there. We are absolutely 100% spent, and we don’t know why. I hear this story too often from friends and other entrepreneurs, but I’ve experienced it now myself on several occasions. Self-case, which tends to fall for women way down the list, needs to be bumped up to number one. One before everybody else, before the start-up, before our children, before everything, because without us, the start-up will likely fail, so we are the largest risk factor.

Melinda Wittstock:         Oh my goodness, so true, so profound. It took me too long to learn that lesson too. The adrenal burnout thing, I know so many women who really put themselves last, paid themselves last, kind of put everything, worked incredibly long hours and ended up really with nothing, and there’s no start-up without you.

Kelly Fitzsimmons:          There’s no start-up. There’s nothing, and I mean, one year, in one of my start-ups, I was in the ER 54 times. I did it on weekends. I mean, so the adrenalin would keep me going through the week, but by the time I took a breath on the weekend, I would collapse and the migraines that I was getting were not treatable. I was blowing past all the medication I could take. I was allergic to a whole class of migraine medication, which made it really tricky, and I just kept soldiering on. By Monday, I would be back in, but who really suffered was my husband and my children, who didn’t see me for almost a year. I really thought I was unbreakable. It was a fallacy of inductive reason, or hyperbolic discounting that up until then, I’d always been able to pull through and soldier on, but the past is not the best indicator of the future. If you try to predict the weather by yesterday’s forecast, you’re going to be wildly off.

That’s what we do all the time, particularly with self care. Yeah, once you get a really good taste of having your health taken away from you, it re-prioritizes how you see the world, and either you recognize health for the gift that it is and see how precarious it is, or you’re really in the delusional state. It’s not something that we really can mistreat and expect to be there for us when we need it.

Melinda Wittstock:         Such profound advice. Kelly, I know you have a book coming out, which I can hardly wait to read. Tell us just a little bit about that, and also how people can find you and work with you.

Kelly Fitzsimmons:          Excellent, so the title of the book is Lost in Startuplandia: Way Finding for the Weary Entrepreneur, and it comes out of my own life experiences, but those of many of my really gifted friends who have been on this road for 20+ years and have seen some spectacular success and some spectacularly public failures. While I’ve had some spectacular failure, a lot of mine was private. Almost no one knew how badly I had failed. In these cases, they didn’t have that privilege. There were on the world stage. Everybody saw them tumble and fall, and how the pick themselves up and dust themselves off and keep going is critical, because the main thing, and I think this is a missing in static literature, is that there is sort of this underlying enthusiasm and survivor bias problem in which we only see the most successful people and tend to have their stories reinforced, and so we go, “Well, I can do that.” We don’t see the body count. We don’t see how many millions have failed for that one person to have broken through. We think that there’s a road map to success, but there really isn’t. It’s completely individual.

It’s a combination of our unique talents, our ability to weather storms, and most importantly, a good deal of luck breaking in our way. It’s like when you try to replicate somebody else’s success formula, you’re doomed to fail from the outset, but conversely, there’s multiple roads to success, and you have to find your own, but there are some surefire ways to fail. The book really concentrates on the lessons learned by myself and others, on what are the way in which we really get lost? It covers topics such as self awareness to the relationships that we surround ourselves with, to self care as I’ve hinted at, and more subtle things too, like decision making and how often we’re just working from gut, because our hair’s on fire.

There’s an entire class at categories of cognitive biases that are around decisions that are made too hastily. Yes, that’s kind of par for the course when we’re traversing this terrain. The book is really a heartfelt attempt to share these hard lessons, and to do it in a way that’s funny and engaging, but at the same time, painfully real, so that I hope the readers have an ability to click in to the things that sound familiar and get to see themselves through other people.

Melinda Wittstock:         How wonderful. How can people get a hold of it? When’s it out?

Kelly Fitzsimmons:          It comes out in October. We will have our website up soon. It’ll be lostinstartuplandia.com, but if they follow me on Twitter, I will be able to send a link, so as soon as it’s available to get, they can get a first copy.

Melinda Wittstock:         That’s great, and we’ll make sure that we update the show notes and so everyone can find it. I will remind all of our listeners to get that book. Kelly, it sounds magnificent and thank you so much for just talking so openly and authentically about your experiences, and putting on your wings and flying with us today.

Kelly Fitzsimmons:          Thank you so much. I really appreciate it.

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