FTC 164 | Starting Startups

164: Starting Startups: Life Of A Startup Founder with Kelly Fitzsimmons

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In reality, life as a startup founder is all about dealing with crisis after crisis. Even the most seasoned founders can get disoriented or worse, suffer from overload. Serial entrepreneur Kelly Fitzsimmons was headed for a breakdown at one point until it became a life and death experience. In the throes of despair, she rallied and came back, but not without the scars of a warrior still fresh. She tells her tale not to entertain, but to teach you the way through. In her new book, Lost in Startuplandia, she goes beyond the glitz of Silicon Valley and focuses on you, the founder, just as she was to show you the way back to sanity. She’s here to tell her story and to help you in your own mission of starting startups.

Starting Startups: Life Of A Startup Founder with Kelly Fitzsimmons

We have a very special guest to share with you. Stay focused and lean in as we dive into another expert master class from an industry leader who can’t wait to share. She started six businesses. She has a master’s degree from Harvard. Someone this smart should sail through life and hit the success bell over and over again. In reality, life as a startup founder is all about dealing with crisis after crisis and even the most seasoned founders can get disoriented or worse, suffer from overload. This serial entrepreneur was headed for a breakdown at one point until it became a life and death experience. In the throes of despair, she rallied and came back, but not without the scars of a warrior still fresh. She tells her tale not to entertain, but to teach you the way through. In her new book, Lost in Startuplandia, she goes beyond the glitz of Silicon Valley and focuses on you, the founder, just as she was to show you the way back to sanity. She’s here to tell her story and to help you in your own mission. Welcome, Keller Fitzsimmons.

Thank you so much, Mitch.

Kelly and I have some history. We’ve met several times, but the last time we met, we’ve spend some quality time together. I loved my time with her that I had to have her share with you. She is one incredibly amazing individual. Kelly, how did all this get started for you?

My life took a radical detour. I was in grad school. I was studying Comparative Religion and my focus was Archeology. I was teaching in the field. I was working at that time in the Crimea down in Sevastopol on a very early Jewish synagogue that we had discovered under a cathedral. I loved that work and I couldn’t imagine doing anything but that work. I got a phone call. My dad had invested in a startup and I ended up coming back to Milwaukee to work at that startup. It was a bulletin board system. That dates me a bit. This is pre-World Wide Web and a bulletin board system or BBS was an online community where people would get together to share ideas.

Early communities included like AOL and CompuServe and Prodigy. This one was very aptly named. Its name was Vortex and it pretty much sums how it all went down. I was there for a year and witnessed this chaotic swirling mismanagement and in the end, Vortex sucked itself into non-existence. I was there to witness all this and I walked away from the experience dizzy. Something had coalesced. I had created some relationships. I had gotten an insight of what a startup looks like and I decided to start a company, not in other BBS, but instead I’d seen another opportunity, which was information security.

Bare knuckling through overwhelm is not going to win in the long run. Click To Tweet

As these online systems were coming online, it was very clear to me that there was so much potential for harm. As easily as you are, I could go onto these platforms and systems, someone or something else could come on to ours. That one insight proved to be the starting for me of Sun Tzu Security in 1996. My business plan was quite noble. I would imagine what the founder of Vortex would do and then I would do the opposite. To date, that is my most successful company. Sun Tzu ended up merging with Neohapsis, which was one of the industry leaders in information security in 2003. In 2006, we were purchased as part of an industry roll-up. In 2015, Neohapsis was purchased by Cisco System to become the Security Division.

When I started my software company in 1985, my source of information was CompuServe. What I did is I went onto the lawyer SIG, Special Interest Group and I started to ask lawyers what they thought about my idea. I guess I made an impression, there were a lot of attorneys that got excited about the ideas I was sharing. I chose a few of them and they became my absolute best beta testers. What was interesting about that time is that computers were not very common in 1985. A PC costs $6,000 and came with a whopping ten megabyte hard drive.

I remember it well. I was programming back then. My platform at the time was a Macintosh. It had just hit in 1984 and I was one of the first people to get it. I was only eleven at the time, but I was completely obsessed. I couldn’t imagine a cooler thing in the world than this thing that delivered incredible graphics. There was no more C Prompt and it was this revolution. To this day, I remember the Adobe Illustrator. They had an animation that they did try to sell the early software for Mac. It blew my mind. I couldn’t imagine where we were going and how exciting it was going to be.

I remember that we had been working on a Macintosh version of our time and billing software Timeslips for quite a while. We hired a consultant who would help us deliver the Version 1.0. He was such a disaster that we eventually hired our own Macintosh programmer who was able to reuse a lot of our Pascal code. We had a Mac product. I have an Emmy Award from Macworld Magazine because we won product of the year in our category.

That’s such a big deal. I remember when that was the thing.

Here you were at this point in your life where you had sold or being part of the sale of a successful startup. How much time had transpired from the time you came back from Crimea?

FTC 164 | Starting Startups
Starting Startups: It’s very hard for those who were not part of the dot-com boom to understand the craziness of that time and the magical thinking.


We were in the Ukraine and we were in the city of Sevastopol, which was fascinating because we entered Sevastopol, when we started digging there almost two weeks after it had opened up for the first time. Sevastopol is the home of the Black Sea Fleet. It was a closed city and essentially it had gotten locked in time. The people who lived there could not travel out and nobody other than high-level military brass could go in. When we walked in, we walked into a city that had stopped interfacing with the outside world. It was like walking into the 1920s. It was such an extraordinary experience. Here we are as archeologists and as time travelers. It left such an impression on me. I was planning on going on for my PhD. I saw the future. I was an archeologist. This was who I was. All of a sudden, this interruption. Here I was back in Milwaukee at home in Wisconsin and working at a startup. I was hooked.

I saw the future of what the internet could be and the World Wide Web specifically. I looked at it through the lens of what could possibly go wrong. If there’s any theme to my career, it’s this lens of that could go sideways fast. All the three industries I was involved in, the reason why I stepped into it was out of a desire to be helpful. There were much faster and easier ways to make money in all three categories and I kept going for what was the one that spoke more to my sense of purpose. In the early days it was around safety. It was around a deep concern for businesses going out of business because of intellectual property theft.

This sounded like a great outcome for you. Where in your journey did you manage to go sideways yourself?

The good news is I went sideways pretty fast because I get caught up in the go-go ‘90s. You were there to experience this and you can tell tales. It’s very hard for those who were not part of the dot-com boom to understand the craziness of that time and the magical thinking. I remember an article in Fast Company that said, “Why have one company when you can have two?” I went, “Genius.” I started a second company. Sun Tzu was doing well, so why not go for two? I went from a professional services firm essentially into product. We created a company called PRISM. To date, it is my best named company. It stood for Proactive Remote Information Security Monitoring and it predated the first major player, which was Counter Pain, by several months into the market.

We had a major Fortune 50 as a client. We got strategic investment out of France from another global company that was in the traditional security space and took on essentially venture debt. Loans are to be had, so I went out and got some bank loans. I’m signing all these personal guarantees. I have no idea what this means because I can’t fail. Up until that point, I’d had some significant challenges. It doesn’t sound like it in my bio, but what my bio misses is that I have dyslexia. I didn’t start reading until I was in college. To go to Harvard for graduate school was such an extraordinarily big deal, it was not anything that anyone saw in my future.

When I graduated, my stepmother sent out announcements to all of my middle school teachers, including the principal, who were all pretty much convinced they might be going to jail. I had this extraordinary experience that taught me a lesson and it turned out to be the wrong lesson, which was if I buckled down and tried hard enough, I could do anything. There are some things that can come out of the complexity and randomness of the universe that none of us are prepared to handle. One of those was the dot-com crash. Suddenly the liquidity of the market starting in March of 2000 completely dried up. Where we could get more capital and it was always there, that was no longer true. Certain business assumptions went to the wayside very quickly. If I had been unwilling to look at myself and my involvement in it, I could have told and I did tell for quite some time the story of the dot-com crash.

To be truly self-aware, we have to do a meet-and-greet with our inner demons because they are the ones that are driving the show. Click To Tweet

Everybody got clobbered. I ended up with $5 million in personal guaranteed debt. I spent the next three years working it out. We had an exit and I was able to not just clear my debt, but also have some funds left over to start a new company. That story is super convenient and it makes me sound pretty good, but that’s not the truth. That’s full of lies of omission. The lies of omission were the failure of PRISM was absolutely my fault. I was a very inexperienced CEO. I tell stories about walking around the office trying to look like a CEO and I didn’t know exactly what that meant. I’d watch Star Trek and I’d try to look like Jean-Luc Picard. I would say things like, “Make it so,” and it’s horrifying.

It’s so funny how parallel lives we’ve lived. After I sold Timeslips, I came back to Massachusetts and I figured I would go be an entrepreneur in residence and help VC firms, maybe even run a couple of companies for them. I got zero response when I sent out offers to 30-plus VCs here in the area. I started following up. Nobody would take my call, until finally one young VC did. I said, “Did you get my resume and did you get my letter?” He goes, “Yes.” He said, “We stopped reading it when we reached your age.” I said, “I don’t understand. What do you mean? I just achieve what you want every single one of your CEOs to achieve.” He said, “No, but you’re too old. Most of our CEOs are in their mid to late 20s and you’re 44.” I said, “I got it.” I now understood what I had to do next.

Eventually, they did come to me. They funded me and I ran a firm for VCs called FurnitureFan. We were going after Furniture.com. We were building the largest furniture shopping site in the world, which we did achieve. We had at one point in the year 2000 more traffic than most search engines of the time, but we don’t know if that traffic was real because we were paying people to help generate it. You’ve heard of click fraud. It’s very likely we had a lot of that going on. Here’s the important thing I wanted to point out. I too had no idea how to be a CEO. Readers, this is for you as well. What I could not do is I could not delegate. I had to learn to delegate in order to grow and scale anything because you can’t do it alone. Even in our minds, we think that we can when we know that we can’t. I’m sure you had your experience with that as well.

The good news is with dyslexia, I learned very early on to delegate. That’s probably one of my superpowers because I couldn’t do it alone. I had people who had to help me get into my locker at school. They would come and they’d help me with my combination every single day. I learned that particularly the skill I didn’t have. One, strangely enough, that here I am at 48 still struggling with it but learning and figuring out is I was incapable of taking feedback. I was so scared of being perceived as wrong that I would send out all sorts of messages that you did not want to give me straight feedback. I would beat myself up if I made a mistake and, “Kelly’s hard on herself. She’s got this.” That was one way I signaled. Another way I would signal is I wouldn’t ask for feedback. I would make proclamations. I would say, “This is the mountain we’re going to take,” and wouldn’t even take the time to investigate because I wanted to look decisive. I wanted to look like I knew. I had some singular genius and that I didn’t want their gifts and contributions.

That is not an uncommon young CEO mistake to make. I share it because it is a disastrous one. If you do not have a good feedback system, a trusted feedback system where people are willing to tell you not just the truth but the hard truths, the things that aren’t working, how you’re not working, you are not self-aware. You have no idea how to improve. You are first of, self-blind. Secondly, you’re incapable of making a good decision because a quality decision-making requires triangulation. You got to get the input of others. People have to speak up because we all have blind spots and we’re full of cognitive biases, implicit bias and confirmation bias specifically, where we only see the things that reinforce our held beliefs.

There’s no way around that without triangulation and people willing to give you the hard truth and be your truth tellers. I did not cultivate that in my early career. The real truth of why PRISM failed was there was a lack of feedback loops. I wasn’t in conversation with my team. They saw things, but they didn’t tell me because I had very much made it clear I wasn’t interested in hearing it. The other piece of it was that I didn’t want to be wrong. I didn’t want to be seen as wrong. I never said, “I don’t know. Can you tell me more?” An open-ended question never dawned on me. I only sought to prove how my viewpoint was right. I never tried to do something like figure out how my viewpoint was wrong, which is a much more helpful way to gather other’s input and be a decent decision-maker.

FTC 164 | Starting Startups
Starting Startups: The decisions that we make are almost all emotionally based.


All of these are the lessons that all of us learn as we go through the process of building a company. Kelly, let’s go back to something you said. You mentioned that, “I was $5 million in debt.” I felt like if that were me, I would need to find a dagger to plunge into my heart. How does one handle being $5 million in debt at a time when most of the internet companies around you are failing?

It wasn’t just the internet companies. This is the weird thing about the dot-com crash. It impacted manufacturing too. Here’s the hard piece of the story, which is I felt in my twenties that I was doing this all by myself. I got married at 25 so I could lose my last name. My father was a very successful entrepreneur and manufacturing CEO. I didn’t want anybody to ever credit my success because I had a powerful and successful father. I very consciously didn’t use his name. I was making my own way in success. When I went out to get the bank loans, they asked for a co-guarantor. I had no idea what a co-guarantor was. I asked my dad and he said yes and he co-guaranteed my loans. When the loans were called and the company collapsed, it wasn’t me on the hook. It was my dad on the hook because I had equity in my condo that maybe came up to $50,000. I had no assets to back up that debt. I did not know what I was doing, but my father did.

What happened was that manufacturing went absolutely flat. His company for the first time in 40 years didn’t sell a machine that year. He was nervous and he was angry rightly so at his daughter who had put him in this horrible position. What ended up happening was that over those three years, my dad did carry the debt. He didn’t call my loans, which I would’ve had to declare bankruptcy and a lot of people had it much worse. The real problem was that my relationship with my dad fractured. My father means the world to me. Honestly, the entire quest of being an entrepreneur has been to impress my father. To have that disconnect with him and these awkward conversations and angry conversations and for him to be so disappointed in me, frankly that was what caused me to stumble.

During the day, I looked like a very successful CEO because I had merged the healthy companies, Sun Tzu with Neohapsis. I was CEO of the combined company. I’m out there on major stages, very public and speaking and major articles and writing for network computing. On paper, I looked very successful because I was able to hide what had happened, but I knew what was happening and I was suicidal. I was terrified that I was never going to figure this out. Neohapsis was a professional services firm. They don’t exit for the kinds of things that normal tech companies do. I couldn’t see a way out. For three years, I had the facade and the persona of everything is great. We’re doing gangbusters and thank God Neohapsis was very successful during those times. I was running a very profitable company, but I still held that debt.

What ended up happening, I shared this in the book, my biological mother who had divorced my dad years prior stepped in. She called him and she said, “Donald, you’re breaking the kid. She’s going to die.” I don’t think my dad understood how personally I was taking this. How I was desperately trying to figure out how to right this wrong. I was working 100-hour work weeks and I was just beside myself. There was a moral injury I was dealing with, which was there was a deep lie that I was telling. For somebody who considers herself a pretty honest person, how can I carry this lie of this day persona, nobody knows about the debt. I had engineers that were incredibly mad at me at the time. When the transaction happened, they thought they were going to have options in the new company, but they didn’t understand that those options were dramatically underwater. I couldn’t give them to them because it would have been saddled with pretty epic debt. I hit my wall and there was no pretty way to package that. It was a heartbreaking grief.

I completely understand that being a dad, being a founder and suffering from imposter syndrome as I did back then as well. Kelly, everything you’ve told us left their scars and an impression on you. You are an incredibly resilient individual, but you’re also now a much better person than you probably ever were because of it. Not because of the scars, but because of the learning that goes with it. I’d like to turn the floor over to you and have you teach our readers the most important lessons you believe can help other startup founders navigate these shark-filled waters to an island of pleasure and delight which is called the liquidity event. Tell us about that.

Making good decisions can mean seeking the opinion of others, particularly those that do not think like you. Click To Tweet

One of the things that I learned out of this heartbreaking failure is that at the end of the day, as a leader, it comes down to one thing. Our lives and the quality of our lives are determined by luck and the quality of our decision-making. That’s it. We can’t do a damn thing about luck. The universe is full of randomness and bad things will happen to us. I’m sorry to be the bearer of that news, but we can do a lot to improve the quality of our decision-making. I didn’t know in my 20s and in even my 30s that there was such a science and discipline to decision-making. I had even read some of the books by Daniel Kahneman who’s one of the seminal thinkers in cognitive psychology. He was the one who blew up the concept that we make rational decisions. It was his work with Amos Tversky back in 1974 that introduced us to the idea that we are incredibly irrational.

The decisions that we make are almost all emotionally based, each and every last one of us. That was when we came into the world of cognitive biases. What is that? What does that mean? It means that every one of the decisions we make, for the most part, the outcome is luck. We like to think that we have lots of good luck that obviously it’s the quality of our decision-making. The only way we can be sure that it’s our decision-making and the quality thereof is if we have a process and we go through a very rigorous and detailed process, not just for making each decision, but going back in time and checking for hindsight bias. Hindsight bias is that wonderful thing that when we have a good outcome, we think, “Good decision.” If you think about that for any length of time, you’ll quickly see that it’s decoupled.

The quality of our decision-making, if it doesn’t run a rigorous process in which we are including the feedback of others to triangulate so that we can catch our blind spots. If we are not looking deeply into the emotional underpinnings like, “Why are we making these decisions? What is driving me here?” We don’t know what’s at work because it’s our emotions that are leading. The work that Tversky and Kahneman did proved unequivocally that we are terrible decision-makers, each and every last one of us, but we love to think we’re experts at it. How do you know you’re an expert decider? Are you running a process? Yes or no? I mean a sophisticated process, not pro and con list. That hasn’t changed since Ben Franklin and I think we can do a lot better than that. Why am I spending so much time here?

Backing up, what I realized is that in my 20s and my 30s, I thought I was a leader. If a leader means a good decision-maker, I was a terrible decision-maker. Everything I did was based on gut instinct and my gut instinct was very well-attuned to making emotional decisions. What was the basis of these emotional decisions? To be good at this, we have to become self-aware. Self-awareness, most of us know our aspirational selves. We know the things that we tend to do. We can do pattern recognition. We can look back at historicals. We can say, “I tend to do X, Y or Z in these scenarios. If that’s what we mean by self-awareness, most of us are, but that’s not self-awareness. A three-year study by Tasha Eurich that she published in her book Insight found that 95% of us think we’re self-aware. However, only 10% to 15% of us are. That’s a real significant and scary delta.

Tell me what you mean by self-aware. Help us understand your idea and how that applies to what you’re talking about.

Self-awareness is more than aspirational. It is more than pattern recognition. To be truly self-aware, we have to do a meet and greet with our inner demons because our inner demons are the ones that are driving the show. This is our shadow self. This is the person that shows up when everything goes wrong. This is who we are in survival mode. For instance, I know that I’m very strategic. I’ve taken a ton of tasks and every time it comes back very strategic. I’m also very positive. That’s another one of my strengths. I tend to see the best of bad situations. When everything’s going good, strategic and positivity, that’s great. What happens when things go bad?

FTC 164 | Starting Startups
Starting Startups: We tend to attract people who share our opinions and our world view.


When things go bad, I go into Pollyannaism. I go into, “It’s going to get better,” even though I have no attachment to reality and I can get untethered there. With strategy, I become manipulative and I’ll start manipulating to get my way. These shadow qualities are very much driving the show. That meet and greet with our inner demons, most of us are not willing to sit down and look under the hood and ask ourselves the hard question, “What is driving us?” I’ll give you the answer. This has taken many years of personal development work to come to and working with a very gifted executive coach, John Smith, helped me realize that every one of my decisions was designed to make me look good.

It’s interesting that particular thing was driving you because I suspect it drives a lot of us.

If you spend any time with yourself and you look why I made that decision, almost always, it’s designed to make us look good in some way. If going back in time, this particular tendency was well known even to the ancient Greeks. For instance, if you went to the Oracle of Delphi and you are leader seeking advice on what was the most likely outcome. You would go there and you would go to the temple. As you’d walked through the forecourt, you would see these maxims, aphorisms inscribed in stone. One of them was “Know thyself.” Scholars debate what this means, but there are two common opinions. One is it was a check against hubris. The tendency to be overconfident because overconfidence is a key driver to bad decisions. Almost all of us are overconfident in some way. That has to do with a lack of self-awareness, Ergo, know thyself.

The second piece is it was a check against going with popular opinion. The ancient Greeks knew well, as we do now, that the opinion of the multitude, the popular decision tends to be the wrong decision. The right decision tends to be the harder one, the one where we’re not going to be popular or well-liked. That looking-good piece can be subtle but sometimes it’s easier to go with the popular decision. The one that’s most likely to make the employees happy. The one that’s most likely to make the investors happy. The one that you don’t have to argue and fight so hard for it. Most of the time that’s the wrong decision because it’s the easy decision.

It almost implies that you should instead go with the difficult decision even if in your heart you don’t think it’s right. You know about this bias that you talk about. Should I try to make a decision and then say, “Let me just go with the hard one that I don’t think is right because that’s probably the right one?” Help me understand how that would work.

Here’s a simple rubric that I’ve learned that I think is such a great way to approach this problem. Naturally as leaders, we tend to go out and we say, “This is my idea. This is my strategy to get from A to B.” We look for the data that supports our opinion. We talk to people and we ask people and they say, “Yes, boss. That’s the right way to do it. That makes a lot of sense.” What we don’t realize is that we’re almost always leading the witness. They can read us like a book. They’re trying very hard to appeal to us. If they see that we have any inclination on a direction, they want to reaffirm that for the most part.

The moral high ground is huge addiction for those in leadership. It's a good shot of dopamine. Click To Tweet

There are people who are willing to be disagreeable, but they tend not to last long in upper executive management. Our egos tend to win out, they’re just difficult dark clouds that rain on our parade. Those are some of the most important people on our team and dramatically under-utilized. When we go out and we did that typical approach, what we’re doing is catering to confirmation bias. If we look at science as a model, scientific research have to be very careful of bias. They’re doing double blind tests and they’re always trying to make sure that they’re not affecting the quality of the data that they’re getting.

One of the ways that we can do this in executive management is to look for how we are wrong. Dedicate ourselves to “What is it I can’t see” and ask questions through that lens. You’re sure you’re wrong. You’re positive you’re wrong. Figure out how you’re wrong. Doing it that inverse way does this miraculous thing where it opens you up to possibilities. It opens you up to curiosity. It takes your ego immediately offline because you can’t feed your ego when you’re trying to explore how am I wrong in this situation. What is it I cannot see? This means you’re going to have to seek the opinion of others, particularly others that do not think like you. If you start doing that, you are well on your way to starting a good decision-making process.

Let’s see if I can summarize the formula that I’ve just heard. When you have this moment in time where you need to make a decision, ask yourself, “How could I possibly be wrong even though I feel so sure that I am right?” Once you feel like you might have an answer because you are fully biased against this possibility, you then seek out somebody who you believe has very little vested interest in what you’re asking for. Check with them and see what they think. Is that the summary of it in essence?

Yes, you have to cultivate truth-tellers. This is not an innate ability and it’s not part of our current social construct. It’s a very awkward thing to do. You can’t just go out there and say, “Tell me how I’m wrong.” The energy behind that is not going to work. Nobody is going to speak up to the boss like that. The cultivation of truth-tellers or partners in this has to do with creating a new social construct where we reach outside of our social networks to people that we respect that come from different walks of life. They see the world dramatically different. They have nothing at stake in their decisions. It can’t be our spouse or even our close friend. They care about us and want to keep us safe. These are people who may not come from the same religious background. They have different gender. Maybe they are from different cultural orientation. You respect them as a person and as a leader, but you have pretty little in common when you go down the checklist.

The second piece of it is you have to have consent, which means that you go through a pretty formal process of saying, “I need to triangulate some decision. I know I have blind spots here. I cannot see them. This is what I would propose. I will tell you the facts of the situation. You ask me questions around that. At the end, once you feel like you’ve got full clarity of the situation, tell me what you think I am not seeing.” It’s this question and the answer and creating the safety for somebody to tell you like it is. This might take some time. Most people are not comfortable saying the emperor has no clothes even if they don’t have anything at stake. It’s the cultivation over time and the willingness not just to cultivate somebody to do it for you, but that you’re willing to do it for them. There’s some reciprocity there.

What’s interesting about what you’re saying is that you have learned and created a system by which all of us need to follow if we’re going to get the truth. We’re all after the truth. Even though I have these cognitive biases, I still want the truth. After all, if I’m dealing with my own company, I have to know what is right or wrong, not necessarily what I think is right or wrong. These are critical skills that you’re helping us develop here. There’s something else that I need to check in on. You said that it’s best not to use friends as the potential candidate for your cognitive bias test. Who then shall we seek out? You say neutral people, but don’t you believe that everybody has a bias of some sort?

FTC 164 | Starting Startups
Starting Startups: The United States particularly is very toxic to art of all kinds. We fear our children becoming artists and yet it’s one of the most powerful platforms that they can be in.


We can see the biases in everybody. Everybody has such a warped lens, but yet we see so clear eyed. If you want to know how warped our lens is, think of that person that you think is a complete nut case and on occasion, we have sounded like that to somebody else. This is a universal trait. None of us is as clear eyed as we think we are. The reason why I say don’t get somebody too close, this is like inner circle stuff, is that we tend to attract people who share our opinions, share our world view. This isn’t everybody. There’s a lot of people who have great, beautiful, diverse group of friends, but that tends not to be the universal case. The other piece is if you’re too close to that person, you can do all the safety checks you want. The fact of the matter is still they have a bias towards you liking them. That’s the hard thing.

Giving the hard truth might mean the end of the friendship no matter what we say. When they call us out and say, “Kelly, the fact of the matter is you’re a flake.” How do I feel about that person going forward? Is it going to damage the relationship? Maybe, I might not be that evolved. When we seek these people out, we’re looking more in the realm of our respected peers, people that we respect, that have nothing at stake. There’s no reason for them not to give us a straight answer because there’s not a deep value to the relationship yet. The thing is if you cultivate it right, there does become a deep value to the relationship, but it’s completely different friendship. It’s one that’s based on the higher desire for both or all parties to be able to step into their highest purpose and to be able to serve others from a place of clarity versus our own terrible warped lenses.

This sounds hard. The reason they say it sounds hard is not because it’s hard to take a step away and examine yourself and say, “Maybe I have this bias that would influence me in the wrong direction because it’s me.” What’s hard about it is to trust that another person doesn’t also have a bias that somehow could play against you.

They do. This is why you can’t just do it with one. This is why it takes time, you have to triangulate. In the book, I write about a construct that I use called the Triad. It’s two trusted truth-tellers essentially. People who are willing to give it to you straight where there are rules of consent. I leverage them for helping me to see what I cannot see. It’s hard. I’m not going to say it’s easy. I had a call with my triad and I just wanted to die. The things that I was seeing, I’m like, “I’ve worked on myself so hard. Is this what’s going on? Is this how I’m landing?” The triad goes, “Yes.” There are things that I do. I’ll be very specific. One of them is I tend to run late for meetings. This is a pretty common thing. I know I’m not the only executive that tends to try to cram one last thing in before they go on that call or they make that meeting and tend to run.

My number is five minutes late. I tend to run about five minutes late, sometimes ten. Every year, I will have it on my list of commitments. My New Year’s resolution is I’m going to be on time. The thing that I didn’t get and thanks to a triad, they said, “What’s the payoff?” I said, “What do you mean?” “You’re getting something out of this. You wouldn’t consistently be late if there wasn’t a positive payoff for you.” After some deep conversation, what we came to is by always running a little bit late, I’m signaling to people that I’m not fully trustworthy. I am not that dependable. You can’t trust me to show up when I say I will. I’m not keeping my promises. I did not like hearing that. It’s true. It’s a way of getting me off the hook of responsibility. I tend to feel overburdened. I tend to feel like I’ve got too much on my plate. I definitely don’t want people making more requests of my time. It’s a very subtle unconscious strategy to create some distance. I didn’t see it and I would have never seen it without their help.

I want to rent your triad because that is brilliant. I am the opposite in one regard is that I’m always early. I never looked at why, but I think part of it is I’m afraid people will disrespect me if I’m late. I don’t want to be disrespected. I show up early which also gives me the moral high ground.

Nobody is perfectly honest. On average, we lie about seven to ten times per day. Changing the world can come down to the actions of a single individual. Click To Tweet

It’s so perfect you’re saying this because the moral high ground is huge addiction for us in leadership, the righteousness. It’s a good shot of dopamine. It has got a chemical signature to it by which we are addicted. Almost all of us. Who doesn’t like to be right? It feels good. It is part of that beautiful thing we can do when we can set up situations so we can have the moral high ground and being early is a great tactic for that. For me, I have to watch it around honesty. I try to be very rigorous with my honesty and when I feel like somebody’s blowing smoke, I get judgy. Nobody is perfectly honest. The studies keep coming back that on average we lie about seven to ten times per day. I think that’s on the low side.

If you think about all the social niceties stuff that we do in lies of omission where you don’t speak up because we don’t want to deal with that issue, I still do that every single day. It’s fun for me to say, “I’m a generally honest person and that person just blowing smoke, he’s just a fraud.” I get that little shot of dopamine and it’s an addiction. It’s the depth of relationship. It will kill your connectedness. The minute that thought goes through my head, it’s almost like they can sense it and they stop trusting me. I think that in leadership we are not aware enough of how our judgments leave others feeling are our judgment. How it causes disconnection and lack of trust. Why would they ever speak up and tell us the hard truths when they know that we’re judging them already and we find them wanting?

It makes complete sense to me. You held a master’s degree level discussion here on exactly what every single entrepreneur needs to know. Readers, if you took to heart what Kelly just explained, this can change your life. Realistically, to get the full treatment, to understand this completely, I would highly suggest you go out and buy Kelly’s book right away. Kelly, you have been so generous in sharing what you know and who you are. These questions I believe will help readers get to know you even better. Here’s the first question. Who in all of space and time would you like to have one hour to enjoy a walk in the park, a quick lunch or an intense conversation with?

I’m going to name the cognitive bias. It is the recency effect, which is the desire to or the tendency to prioritize recent information over previous information. Just because of this moment that you caught me in, the answer I have is Tim Ferriss. The reason is that Tim is starting to pay attention in a pretty significant way to depression, anxiety and he holds a very large platform. There’s a lot of people who spend a lot of time listening to what he has to say. One of the things he’s been putting out there is his interest in psychedelic research. This is a tenure place of interest for me. I’ve supported financially some of the studies, particularly the cancer-anxiety study that happened out of NYU, looking at late stage or terminal cancer and the use of psilocybin. It was game-changing.

The remarkable things that came out of there, one of which stands out is that the people who are facing the holy tremendum, like the mysterium tremendum, that moment of quaking and all before the unknown and the unknowable, which is death. Not only did they find consolation and the ability to make sense of death through their experience, which was a very guided process using psilocybin in a therapeutic context. They marked it, within six and eighteen months I believe, as one of the top five most profound experiences of their life, putting it up there with the birth of a child or their wedding. Even more incredibly, there are cases of remission. The changing of their mindset and how they held the cancer seems to have an impact on the cancer itself.

That is not entirely surprising. This renewed interest in psychedelics of all sorts legitimizes my background. As a sixteen-year-old, eating mushrooms was a bad thing to do back then. Now it’s a good thing to do.

It’s the same for me. I come by this very honestly. Having been involved in the psychedelic research community for a long time, I had the opportunity to get into conversation with Dr. Dave Nichols, who I think he may be the only person in the United States who could legally synthesize LSD. I was telling him about my psychedelic experience in college in which I was using for a period of time. It was the same period of time in which after seventeen years of trying, all of a sudden, I had reading comprehension. He said, “Do you think that’s correlated? It’s not. It’s causal.” I went, “What?”

He’s like, “Your brain rewired itself. You can think LSD.” It was this moment where I was like, “He’s right.” I can credit the fact that I rewired my brain. It was a very intense, in my own way, therapeutic experience. It’s unfortunately unguided and probably misdirected, but it had a profound result. I went from a very mediocre student who had near zero reading comprehension. All my grades were based on auditory recall, which I have very good auditory recall, to all of a sudden becoming a straight-A student, graduating magna cum laude, going to Harvard and all that stuff. It completely changed who I was.

Guidance counselors all over the world can know that the next time you come up against a troubled kid, a little LSD will go a long way. I could see it now. High school principals getting phone calls, “What are you doing to my child? I understand that they’re now tripping at school.” After a pause, a parent would say, “Can I stop by later in the afternoon? I want to talk.” You never know how the future. It’s like that old Woody Allen movie where they go into the future and find out that milkshakes were the highest level of nourishment possible. Kelly, the next question is what I call the grand finale question. It’s the change the world question. It’s a big one. What is it that you are doing or would like to do that truly has the potential to literally change the world?

I’m a big believer in changing the world can come down to the actions of a single individual because that’s how it’s always ultimately manifested. I also believe in the power of the arts particularly because I’m primarily auditory. Music is how I experienced the world. I’m very interested in the healing power of music. I don’t mean just music that’s like in music therapy. I’ve looked to all genres of music and its potential. The way in which I’m right now contributing is I’m working with artists, particularly musicians and looking at them not as wandering artists, but as CEOs of their career and as entrepreneurs and reframing this for them and looking at their experience. I’m working particularly with artists that are on the verge of breaking nationally and having a platform of fame and knowing how they can change a person and not necessarily for the better.

I’ve been working with these artists to teach the tools that I’m talking about here. How do you make a good decision? How do you know yourself when the spotlight is on us? That’s when our demons tend to show up in dance. How do we get ahead of that? At least start to create a community of people who are not interested in the musician because of their fame but are interested in them as human beings that have the potential to shape how we feel and see and experience the world around us. I do think that the industry itself, music, right now is at a low point. People are so objectified and it is criminal what we do to our artists. The United States particularly is very toxic to art of all kinds. We fear our children becoming artists and yet it’s one of the most powerful platforms that they can be in.

This small way that I am right now working, trying to help artists heal some of the trauma and make sense of some of the shadows so that when they’re on these big public platforms, they can make a huge difference into the lives of others by being willing to show up, aim more vulnerable and real, translating that into their music. More importantly that they’re not hurt by that process, which it’s just like their vulnerability and their beautiful humanness is so often used against them in this viciousness that we see online. It’s heartbreaking. These are real people with real concerns that are making a huge difference in the world and they deserve all the talent, the tools and support that we can give them.

It’s an incredible mission that you’re on. I would love to support you in any way I can because it’s so important to me as a person who loves and enjoys music, as a musician in a very amateur way myself. I can relate to that as well. You have one more thing to tell us. That is to describe this amazing gift that you are about to endow upon my audience. Tell us what it is.

This is an invitation. I created while writing the book a decision matrix, which is a series of questions that I workshopped to help catch my cognitive biases and make sure that I was seeking input from others and making good quality decisions. I have now put it into the form of a Google form so that you can very quickly use it for yourself and see what results you are getting. Turn on the lights into some of the things that you might be doing that disrupt your ability to make good quality decisions. For the readers, I am more than willing to give you a copy for you to have as your own on the decision matrix as a form, so that you can play with it and give me feedback. What works, what doesn’t? What are you noticing? What did you catch? I’m looking to do some real data analysis around making this a better tool, but ultimately as a tool to start turning on the lights for people.

This may soon be a very expensive component of a program that you’re working on. Take advantage of this incredible offer and be sure to give Kelly some feedback too. Not only will you benefit from doing so, but she will as well. That’s the way collaboration works in this world. Kelly, thank you so much. You have been an absolute star. Thank you so much and I cannot wait until we get a chance to talk again soon.

Thank you so much, Mitch.

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