Greg Larkin is on a mission to empower entrepreneurs to do their most transformative work – everywhere they work, even when it’s very hard. He is the author of the international best-seller This Might Get Me Fired, an international keynote speaker, and has built some of the most disruptive innovations of our time. He is the founder of Punks & Pinstripes, a global community of entrepreneurs, intrapreneurs, and punks who support and empower each other.
In 2006 Greg was the first person to publicly predict the subprime financial crisis. That prediction propelled him and his startup Innovest to an $18 million acquisition. He subsequently served as the director of product innovation at Bloomberg. Greg has worked across the Fortune 500 to launch transformative products and empower entrepreneurs.
In this episode, Greg and Bryan discuss:
– The enormous power of being different from those around you to create change
– Why anger is a dangerous emotion to carry around
– How cultural change in a company is always going to be met with individual resistance, and why it is necessary for those companies to grow.
Transcript:
Bryan Wish:
Greg, welcome to the One Away Show.
Gregory Larkin:
Hey Bryan, thank you for having me.
Bryan Wish:
Yeah, absolutely. Well, excited to be here with you today. I think we’re in for a treat. So Greg, what is the One Away moment that you want to share with us today?
Gregory Larkin:
Yeah, sure. There was a moment that happened to me on January 8th, 2015 that will forever change the trajectory of my life, how I work, how I think of myself, my career, my clients, my values, my boundaries. And I’ll give you a little bit context about why I wrote it and when I wrote it.
Bryan Wish:
Yeah.
Gregory Larkin:
And then I can read you the letter. I still have it.
Bryan Wish:
Oh my God. That’s a treat, for sure.
Gregory Larkin:
And you’re also get a sneak peek into my upcoming, I’m writing my next book right now. And I start the book with the letter, which is in my view, there’s a degree of testicular fortitude that goes in with kicking a book about corporate transformation off of this letter. But it’ll gel when you hear it.
Bryan Wish:
Hey, well you got to bring the human element on the people to drive some change. So, let’s do it. Where do you want to start?
Gregory Larkin:
Ain’t that the truth? Yeah, okay. So it’s January of 2015, and I am on the brink of a nervous breakdown. At that point, I was a Director of Innovation at Bloomberg. I didn’t just hate my job at that point, it was having such a detrimental effect. My anxiety, I couldn’t sleep. I was waking up every night with horrible feelings. It was destroying my mental health. And on this one particular night, I woke up, I’d spoken to a lawyer about leaving. I’d spoken to my wife about leaving, and what are my options and can I afford to be without this job, et cetera.
Gregory Larkin:
And this one night I woke up at three in the morning, which happens to me all the time. That’s not uncommon. And immediately I started to go through the cycle, “All right, I’m going to count backwards from 100. All right, I’m going to try to meditate. Okay, don’t think about this person who’s trying to shaft you, or this person who you’re fighting with, or this person who’s trying to get you fired, or this person.” And I’m just going down the spiral. And for some unknown reason, I got up and I walked into my son’s bedroom. It’s 3:30 at this point. And I grabbed the marble notebook off of his desk. He’s eight years old and he’s sleeping. And I grabbed the marble notebook and a pencil, and I wrote this letter, and it changed everything. Here’s the letter.
Bryan Wish:
Let’s do it.
Gregory Larkin:
Dear Max, when you were born… Max is my son. When you were born, I was electrified by the miracle of your new life. I was amazed by the reflection of the early morning sun off the red brick buildings in Brooklyn. And the days after your birth, I had walked past those buildings thousands of times, but holding you in my arms for the first time, unblocked whatever prevented me from noticing that glow before. Since that moment, Max, I have spent more time at work than I have with you. There have been times where I’ve done work that is fulfilling and impactful with people who I love and I trust, and that exuberance comes home with me. Many of those people became part of our family as they camped out overnights and weekends, creating something we believed the world needed and did not yet have. Some of those people are still part of our family. But I’ve also done work which defeats me to the point that I’m incapable of being emotionally present for you.
Gregory Larkin:
There are times where I’ve become consumed by a crippling sense of inadequacy and stagnation. Those moments consume my ability to be the father I want to be, the father that you need me to be. Right now, is one of those moments. I make more money and have more status and power than ever before. And yet, I’ve never felt more stuck or despondent. I’m not solving a problem that any actual human being has. I clock in, I try not to get into trouble, I clock out. My days are spent attacking and defending. And at this point, there’s nothing left worth winning. I’ve had to minimize the flame of my inner punk entrepreneur. That flame is now nearly extinguished. I can’t take that home with me anymore. I can’t defer another dream. I can’t allow modernity to pass me by. So this is my resignation letter. There is a tactical resignation letter that an overpriced lawyer has written on my behalf, but this is the real one. I need to know that I can sit by your bed as you sleep, and feel like my truest best self. I love you, daddy.
Bryan Wish:
Wow. Some chills. Wow.
Gregory Larkin:
Yeah, man. It’s probably one of the most powerful moments of my life. And I went to work the next day, and I quit my job. I didn’t know when I would ever make money again. I didn’t know how I would pay my mortgage, but I knew something had to change and I had to take a massive risk and I had to prioritize my values and my ability to live by my values over the immediacy of financial security or status or prestige. And I knew I needed to do that, and I did it.
Bryan Wish:
For sure. And there’s juxtaposition, what a scenario. You had to write the letter next to your son’s bed to fully make a breaking point. I mean, that’s just powerful in itself. You didn’t just like, “Yeah, I quit.” You literally, how you ended it with where you felt like you were in your truest form as a human, when like that in itself. Oh, well thank you, one for-
Gregory Larkin:
Sure.
Bryan Wish:
… opening up like this and making this such a meaningful episode to lean into. As you look back on that moment in time, you had financial security, you had as you said, inadequacy, maybe what you felt like in every other area of your life. When you came home tonight and you looked at your wife and you came home at night and you looked at yourself in the mirror, what were those feelings of inadequacy?
Gregory Larkin:
It’s multifaceted. At the most superficial level, I don’t think I ever came home or very rarely did I come home from my job and think, I’m doing what I was meant to do. And let me put that in context. There’s a really sharp juxtaposition, and I mentioned it in the letter, but I was one of the first people to predict the subprime crisis. I had done extremely impactful work up to that point. Even at Bloomberg, there were things that I had built and accomplished that were groundbreaking, but it was so short lived. And I think, most days I had this sense of, I don’t care about what these people care about. There’s no one here worth fighting for. I have this extreme sense of being an outcast and a pariah.
Gregory Larkin:
I like creating things that are interesting and new to the market, or new to at least the world, and innovative. These people couldn’t give a shit. And Wall Street, if pumping gas provided the same status and prestige as working on Wall Street, the people I was surrounded by, would’ve pumped gas. It was a complete agnostic. I just felt like such a cultural freak on such a regular basis. And there were times where I was able to get into the flow and the head space of doing my work and building things that I cared about, but I never found my tribe. And if anything, I felt like I was an inconvenience to the people who were there, who fit right in.
Gregory Larkin:
So, that’s part of it. I think the other part of the inadequacy was that it was, and I think afterwards, it’s in much more stark clarity than it was at the time, but if you’re a transformationist inside of a large organization, you will always spark a civil war, always. It’s your fucking job to start a civil war. You are telling people to change. And most of them don’t want to change, or most of them understand that change is essential, but when it comes down to them as an individual, their immediate ego driven gut reaction is going to be, “You can’t tell me how to do my job.” And so, you are constantly slamming into the wall of ego and obstructionism and bullshit.
Gregory Larkin:
And that was my day every day, that was my life, was trying to navigate being the enemy of very powerful people, very rich, powerful people. And sometimes I could convert those skeptics and those resistant obstructionist into supporters and advocates and champions. And since I left, I’ve become much better at that. But at the time, I would just move from one political pitched battle to the next, constantly. And that consumed 90% of my energy. And so, I think that was the inadequacy. It was just, I was exhausted from fighting all the time. I wasn’t building, I wasn’t creating, I was just fighting. I was just trying to stay ahead of which faction was forming and how to protect myself from it.
Bryan Wish:
Yeah. It sounds-
Gregory Larkin:
I mean-
Bryan Wish:
Oh, go ahead.
Gregory Larkin:
That’s Max, by the way.
Bryan Wish:
Hi. I just learned a lot about you. I mean, that had to be so empty and draining and soul sucking as you were talking, I mean… Go ahead.
Gregory Larkin:
Yes, it was. At the time it was, and it didn’t have to be.
Bryan Wish:
Sure.
Gregory Larkin:
And I think there’s a way to walk into that environment and own your weird, and say, “I’m not like one of you, I don’t aspire to become one of you. If I’m co-opted, I consider that in validation. And if that’s not something you can handle, then why don’t we all move on with our lives?” And there’s a certain confidence and swagger and pride with owning that, and there’s a certain kind of palpable, there’s defiance behind that statement, there’s integrity behind it, and there’s a certain level of tactful irreverence. I realize that’s an oxymoron, but it’s true. I didn’t know how to do that yet. I probably learned how to do that because of that experience, but I didn’t know how to do it at the time. There’s enormous power in being different, and there’s enormous power in owning it and saying it out loud like, “I have no desire to become one of you. Take it or leave it.”
Bryan Wish:
Yeah.
Gregory Larkin:
And I think there’s an art to that, there’s an art to knowing that, there’s an art to communicating that, there’s an art to communicating that in a way where people feel like they’re also invited in, rather than just pushed away. I didn’t have that dexterity at the time.
Bryan Wish:
Mm-hmm. Yeah. I mean, I think belonging to yourself fully, and as you said, owning that, there is tremendous power in that, because you’re not going to try and show up in an environment you don’t belong in. You’ll be able to identify those areas much quicker. Sometimes though, if you don’t mind me going here, when we do that, I’ve done this myself. When we try and maybe fit in, or fight a losing battle, it stems from maybe certain things in our past that maybe we’re not aware of.
Gregory Larkin:
Sure.
Bryan Wish:
Or we’re unconscious to the behavior patterns striving them. So I see grinning over there, or smiling.
Gregory Larkin:
Yeah.
Bryan Wish:
What did that just bring up? I mean, how did you connect to that with that statement?
Gregory Larkin:
Oh, I mean, I can tell you exactly what that shit is.
Bryan Wish:
Right. Yeah, that’s where I’m going. So I’m trying-
Gregory Larkin:
Yeah. It’s something I’m conscious of and cognizant of and mindful of, but it took me a while. I nearly got held back in fifth grade. I was a horrible student as a kid. I knew I was smart, but I was fundamentally incapable of connecting to my own intelligence. It was a really weird thing. All of my teachers throughout elementary school were like, “Is this kid okay? I think he’s not okay.” And eventually, in high school, I started to find my footing, and I discovered that there were things I was very good at. I could write, I could communicate, and I wound up going to a very good university and doing really well. And I eventually discovered that I was great.
Gregory Larkin:
I had talent and ability, and it doesn’t necessarily come out in all of the conventional ways, like my brother, for example. My brother’s a physician. My brother didn’t study for the SATs, but he did get a 1,500. He didn’t care, he’s just like, “Whatever, it’s just a test.”
Bryan Wish:
Those people. Those people.
Gregory Larkin:
The answer is in the question. He has always been brilliant and an extreme in all the ways that get measured. He’s always been this guy who’s just like, “I don’t freak out before test. I just do them and I do well and whatever.” I mean, he works very hard, I’m not taking anything away from his intelligence.
Bryan Wish:
Right, but your value and your sense of worth, and your sense of completeness is just in different ways. It’s not better.
Gregory Larkin:
It’s fundamentally different.
Bryan Wish:
Fundamentally different. And so, no wonder you did it. And it also makes sense from, I’m hearing you show up in this, I mean, I’m sure that people-
Gregory Larkin:
No, hold on. I have to jump in though.
Bryan Wish:
Oh, yes. So sorry, go ahead.
Gregory Larkin:
I carried such a spiteful chip on my shoulder. Once I’m going to college and I’m on the Dean’s list and I’m consistently have a great GPA, I went to McGill University in Montreal, and I’m back home in New York city. I remember this one time, I’ll give you a concrete example. There’s this one time, I’m 22, 23. It’s the summer before my senior year of college. And I’m on a subway and I see a woman, and she’s got a stroller with her, and I’m like, “Oh, shit that’s my fifth grade teacher, Mrs. Oche, the one who tried to get me held back.” And I’m like, I’m going to go say hello, but this is what happened. And I go up to Mrs. Oche, I said, “Hi, are you Barbara Oche who used to teach fifth grade?”
Gregory Larkin:
And she’s like, “Yeah.” I’m like, “Hey, you may not recognize me. I’m Greg Larkin, I had you when I was 10.” And she’s like, “Oh, I remember you, Greg. How are you?” And I tell her, I’m great. I’m doing great, I have an awesome GPA, I’m going to McGill, I have an internship with Doctors Without Borders, and da, da, da, da, da. She’s like, “Oh, that makes me so happy.” I’m like, “So, is this your daughter? Is this baby your daughter?” And she’s like, “Yeah.” I said, “She’s very cute. Well, I hope you’re a better mother than you were a teacher.”
Gregory Larkin:
Who the fuck does that, Bryan? That level of, who carries… How fucked up is that of me to carry that shit around, waiting for the perfect opportunity to unload this list of grievances on the people who I feel perpetuated them? And at that moment, and very young in my life, I think I had this really stark realization, which is, anger is a really toxic thing to carry. She wasn’t angry at me. She had moved on with her life, this woman, she only wanted me to be doing well. She was genuinely happy to see me and learn of all my success. Her desire to hold me back in fifth grade was because she was concerned for me.
Gregory Larkin:
And I see her 15 years later, and I’m like, “Fuck you.” I’ve been carrying this around for 15 years, looking for a place to park it. And so, part of it, when I go back to what that was when I had a, yes, on some level, there’s a sense that I know the difference between the work I’m doing now at Bloomberg and the best work of my life, and the difference between the two is not good. But there’s also that other side to it, where I can become individually, I can become very begrudging, angry. I start to become resentful of the circumstances around me that I believe are conspiring to hold me back from doing my best.
Gregory Larkin:
And it’s bullshit. At a certain point, the circumstances are what they are, and you can control what you can control. And I had to make a decision to walk and I did, but I still have that thing. I still have that little bug, which is like, “How dare you treat me like a fifth grader who needs to be held back, versus what I am, which is a successful, competent, grown-ass man. Who’s a husband and a father and a professional in their own right.”
Bryan Wish:
Yeah.
Gregory Larkin:
But I think we all carry that around. Everyone carries around that. The one time you felt humiliated in your life, and you can slip into that. You can slip through, seeing the world through those eyes, or seeing your circumstance through those eyes and not even know what happened.
Bryan Wish:
Yeah. It’s such a powerful place to be, I think when channel correctly, but it’s a lot of extra weight and baggage you’re carrying with you, that sucking you, or driving you maybe in unproductive ways. It’s like, you were waiting for that perfect moment to say, “I told you, or I’m proving to you”, but she wasn’t waiting 15 years for you to prove her wrong.
Gregory Larkin:
Not at all. I mean, she had spent 15 years really hoping to the extent that, if you bumped into me again, that great things happened in my life.
Bryan Wish:
Right.
Gregory Larkin:
Literally in the most pure sense of the word, not with any ulterior motive.
Bryan Wish:
Yeah. Yeah. But I think what you said, and back to even Bloomberg and all that fighting, it’s like that chip on your shoulder, built from a young age. I mean, it seems like it persisted, it stayed with you throughout. I guess, is it fair to say, even when you got to the Bloomberg and you were having your soul sucked, but there’s still this sense inside you that you had to prove something. Is that fair to say?
Gregory Larkin:
I think, there’s a fine line between envy and awe. I think when you’re in an organization where it’s inherently hierarchical, it’s extremely cutthroat. It’s deliberately competitive. It’s Wall Street. You’re supposed to fire the bottom 20% of the performers, and replace them with the top 20. It’s very Darwinian in that environment. It’s extremely competitive to the point where it encourages opportunistic behavior where people cut one another down. So, it’s a pretty cutthroat place to be, it’s a cutthroat industry to be in.
Gregory Larkin:
I think in that environment, you’re constantly keeping stock of like, “Wait, how did they get promoted?” Or, “How come they got invited to the CEO’s golf outing?” Or, “How come they… I think they’re making more money than me. Their cars fancier.” You’re always comparing yourself to everyone else in really unhealthy ways, even if it was never your intention to have that happen, even if you thought you were above it. It has this way of slowly consuming your own self identity, meaning you cease to measure yourself in terms of the things that are important to you, and you start measuring yourself in the way that the system wants you to think of yourself, in ways that you thought you would never allow to happen. And I think that happens in a lot of systems, in a lot of companies.
Gregory Larkin:
I think that’s actually a big driver of the great resignation right now. You have people that spent two years in their house, working, doing really well at their jobs. But when you’re in your home, you don’t have that code switch. You just saw my 14-year old son walk by in the back room background. The person you’re speaking to right now is the same person who is going to have dinner with him tonight.
Bryan Wish:
Hmm. Right. Yeah.
Gregory Larkin:
And so, I think in the absence of that code switch that used to happen when I would go to the office in Midtown Manhattan, and then I would take the subway ride home, and it would take me that subway ride to do everything I could to switch back into dad.
Gregory Larkin:
Now you have people going back to work and, it’s like, there’s just no need for me to put that on hold. I’m sick. It’s exhausting having to code switch all the time. And the culture of the industry is a departure from what it means to be a responsible citizen and father and husband and friend and human being. The more it’s like, no, this is cutthroat, this is Darwinian, this is doggie dog, the market waits for nobody, the more it forces you to step into that environment and live in that world when that’s not who you are, the more unsustainable it becomes. I think there’s this subset of the great resignation called, which I study a lot, which is the Entrepreneur Exodus, which is something that is undetected. But when I left my job on Wall Street in 2015, 5% of senior executive leadership in the Fortune 500, only 5% of those people left to become entrepreneurs. Typically, their next move was to another Fortune 500 similar-ish company.
Gregory Larkin:
That’s now 36%. That’s a seven X increase. That’s not just because the money’s better. That’s not just because there’s a lot of DC funding sloshing around the system. That is a massive cultural shift. This evolution from the dorm room startup to the boardroom startup, is not to be overlooked. And I think it’s this incredibly, it’s this hard to read soft signal, and I think the way in which companies tend to react to that mega trend is, “All right, we’ll do a better job of incubating startups.”
Gregory Larkin:
“We’ll do a better job of creating more autonomy for our venture studio”, as opposed to thinking, having a really tough conversation about who has a voice here? Who is empowered here? Who’s unempowered? Who’s disenfranchised here? Who doesn’t have a voice that we need to hear from? Most companies don’t know how to have that talk. Having that talk means someone with power is going to have to give it up. They’re going to hear things that are extremely hard for them to hear. And the consequences of not having that conversation, is that the great resignation and the Entrepreneur Exodus continues to build upon itself and feed on its own momentum. But that’s the moment we’re in. Yeah.
Bryan Wish:
Well, the insight is incredible. And I loved how you gave the example when there were a lot of the resignations, I forget what period of time, you said people were switching from Fortune 500 to Fortune 500. But today, we’re not seeing that same trend, because people are valuing different things and taking that personal agency over their own lives. Now, something that I want to latch onto and segue into with what you do today, you’re at the forefront of this transformation, this digital disruption, our digital trends. Sorry, I’m not saying this right. The forefront of disruption with people having a voice within these companies, to change, be change makers.
Bryan Wish:
You said something that I thought was really interesting. You said people for this the CEO or the people in power to start giving people that personal agency or that voice, it’s going to take a lot of hard conversations or reduction of the ego. How does that happen with an organization? How do organizations of today succeed and thrive and empower within? What does that look like? How does that happen? I know that’s a loaded question, so feel free to dive in where you feel is best.
Gregory Larkin:
So first of all, I think there’s a premise to your question that is implicit that I want to make explicit, because I actually think it’s wrong.
Bryan Wish:
Okay, great.
Gregory Larkin:
I work with C-suite executives across in some of the biggest companies in the world, and I help them transform their companies. And what I always say to them is, it’s first and foremost a question of who, and a distance second and third is what and how. So if you think you can just acquire the AI and acquire the metaverse and acquire the blockchain, and find people who know how to do it, you are not going to have the cultural transformation that will enable those assets to go from being dormant to active. And not only that, you’re going to spend so much money on those assets at a certain point, what happened to GE is going to happen to you. Wall Street’s going to ask, “What the fuck have you done with our money?” And I’m one of these people who worked on Wall Street for a long time. I know what Wall Street is looking for. I know what those difficult conversations look and feel like. I know what’s happening inside of the investment banks before those difficult conversations happen.
Gregory Larkin:
So that’s thing one. There’s a massive alignment with Wall Street’s appetite for change in transformation, that if you cannot make an investor defensible and an investor credible argument of why change is essential and how you’re implementing it, and what are the points that you’re putting on the board every quarter? How does Wall Street know you’re doing it right? Don’t bother. Seriously, don’t bother. Just tell everyone that nothing’s going to change, you’re going to do what you’ve always done, because nothing else will be credible. So that’s thing one.
Gregory Larkin:
Thing two. I’ve read that letter in the boardrooms of some of the biggest companies in the planet. At no point when I read that, everyone is so fucking delighted that someone is finally making it okay to have the talk. People have been walking around with that shit inside of the C-suite, inside of the boardroom for years, decades in some cases.
Gregory Larkin:
And when I go in and I say like, “Hey, there is a wall of obstructionism that exists in every organization where the people who have power are going to resist the people who are transforming the organization, either transforming legacy businesses or creating new businesses where the process and the way it’s done is totally different.” Those change agents are always starting a fight, and the resistance they encounter might be healthy skepticism. It might be risk aversion. It might be traditionalism like, “You might be right, but that’s just not the way we do things around here”, to outright suicide bombers. I don’t give a shit if you’re right, this is my company and I’ll have your ass.
Gregory Larkin:
It exists in one of those four buckets in every organization in the entire world. And I’ve worked with Google, I’ve worked with Uber, I’ve worked with some of the most successfully innovative companies in human history. They still have it. They still have that problem. They still welcome the opportunity to have that talk in a healthy way, rather than in an unhealthy way, because the consequence of not having the talk is, you just hear about it during the exit interview, or you just hear about it when an activist investor takes a 20% stake of your stock, and fires half your board of directors and your CEO. Better you have it in a controlled explosion, than when people become frustrated by the lack of transformation and the lack of change. It’s just a fact that we happen to live in the disruption economy. I didn’t make that shit up. That’s not me being an alarmist. It’s just true.
Bryan Wish:
Sure.
Gregory Larkin:
And part of that is cultural. That’s also true. I didn’t make that up. That’s not me being a scare monger. It’s a fact. Talk about that. Change has to be part of this discussion. Cultural transformation has to be part of this conversation. And I don’t mean cultural transformation as a cost center. Yeah okay, we’ll use the same budget we use to plan the office Christmas party, but we’ll just focus on cultural change. No, it’s a profit center. You have to be fundamentally clear about how cultural transformation ladders up to earnings per share, and who’s going to drive that, and that if someone wants to stand in the way, they have to defend their no to investors, not just to the people who are voting yes. You are going to have to defend your resistance to the people who pay your salary on own our stock.
Gregory Larkin:
And so, when I say that this is a conversation, that is an opportune time to have it, I think I left Bloomberg thinking I was such a freak for believing that. It’s not true. In fact, I could have handled it way better back then. This is foremost, this is the thing that is waking CEOs up at 3:00 AM in the morning today. This is the letter they’re writing to their kids. It’s very front of mind. This is very much in the epicenter of the executive zeitgeist.
Gregory Larkin:
All I’m doing is surfacing something that I think is right there, the minute they trust you, the minute they hear you say it, the minute they detect that there’s a sonar signal that you’re living through the same thing. What I find time and time again, is that they’re freaking delighted that you had the audacity to say it out loud, and they view it as an invitation to make the change in a healthy way, have the conversation in a healthy way. And it’s hard. It’s really hard. That’s a lot tougher than, we’re going to go and build a digital prototype of a new banking app. No, what we’re going to do, is have a conversation about why the 17 previous prototypes were killed right when they were starting to gain traction, and the people were either fired or quit. Let’s have that talk, that’s tougher, that’s a lot harder. That’s the talk, because it wasn’t that there was no validation on the previous 17 tries, it was that the validation was eradicated by mismanaged politics.
Bryan Wish:
Right.
Gregory Larkin:
And if you can’t have that talk, don’t bother building the app in the first place.
Bryan Wish:
Well said. So what I’m hearing you say is, transformation is inside out job, where you don’t just transform by, let me go invest in this technology and slap a bandaid over it and call ourselves innovative and transformative. What I’m hearing you say is, you’re sparking something in the C-suite in a very visceral way, which then drives transformation downward for the whole organization. So my question to you is, once you open up people, and they have these, sounds like major realizations, how does transformation then descend into the organization to drive cultural change, to drive net profits and revenues? It’s it sounds like you’re saying all are interconnected, how does that shift begin?
Gregory Larkin:
It starts in a few ways, a very concrete thing is that when you start to identify, you have to have a regular cadence of meetings where the question isn’t, what’s going well, and what’s not going well, or what products and teams are achieving their goals or falling behind or whatever. You do have to do that. You have to just ask, I think, three basic questions in light of that. Number one, if we want to achieve our goals, if in five years we’ve achieved our goals, or if in one year we’ve achieved our goals, and we went from A to B, what is A, and what is B? Where are we aligned in terms of what has to change for us to win, and where are we misaligned? Where is there no agreement in terms of where we want to go and what we’re willing to give up to get there? Asking that question and creating the scaffolding so that you have an organizational wide view of everybody’s answer to that, is really important.
Gregory Larkin:
And on a regular basis, what do we need to start doing, what do we have to stop doing, and what should we continue to do? Ask that at the end of every meeting, make a point at the end of every sprint to ask that question, and make it very clear that there’s nothing that’s out of bounds. Doing that consistently and regularly so that people are comfortable saying uncomfortable things, and they don’t get fired for it. It is embraced. It is eye-opening.
Gregory Larkin:
Look, I’ve done some work with intelligence agencies before, every terrorist thinks they’re a freedom fighter. It’s true. A 100% of the time they do. It’s very rare that they’re conscripted by force. We’re not dealing with child soldiers, we’re dealing with volunteers who saw a great injustice and took up arms to avenge it or rectify it. I think it’s horrible. I’m not justifying it, but no one who is part of the problem, knows they’re part of the problem. When I say in these huge companies, everybody thinks they are the enabler or the empowerer, every executive identifies in that way. Even the worst obstructionist in the organizations don’t know that about themself. They don’t believe that about themself. The only time it becomes something that they can internalize and see vividly, is when there’s a safe environment for it to be put out there. Not in a the way I did with my fifth grade teacher, which is not healthy, but in a different environment where you’re going to have to hear something that’s hard for you to hear.
Gregory Larkin:
And that message often can only come from what I call a godfather, which is someone who has trust with the old guard, but also recognized the urgency of change. It’s that person, the transformationist cannot also be their own first follower. Meaning, there has to be a disciple who can go into, who is trusted in the old world and can say, “I know you don’t want to do this. I’m willing to hear it, but you have to try.” And that enlistment of skeptics into supporters and into evangelists internally, is critical. It’s the most important thing. In fact, not doing that, will undermine every technological breakthrough you have. It will just create a greater sense of urgency by the old guard to kill it.
Bryan Wish:
Wow. I’ve been just blown away by this conversation, because, well, not only do you know this material so well, it’s the delivery of the material. Don’t even call it material, it’s just your delivery of how you’re speaking. It just lands right with such precision in an emotional way. And I can only imagine real time, when you’re working with top tier exacts, what significant shifts you’re having. And you don’t even probably realize, five years down the road. And it seems like there’s just so much power taking from where you were at Bloomberg, to where you are today, and how you’ve completely transformed in your own right to help companies transform in theirs. You wrote a book about employees, I dare you to fire me, I believe is the title.
Gregory Larkin:
This Might Get Me Fired.
Bryan Wish:
This Might Get Me Fired. I’m sorry. I’m so sorry. This Might Get Me Fired. I’d love for you to share what led you to writing the book. And I know you’re writing your second one right now, which I feel free to plug as we close out, but what have you seen from writing that book, and what do you hope for, for your next book?
Gregory Larkin:
I wrote, This Might Get Me Fired, five years ago. It’s been a while. And one of the things that was very hard for me when I was on the inside, when I was an entrepreneur, there were two things that were hard for me. One was the transition from startup entrepreneur that got acquired that exited, and had to make the transition to enterprise entrepreneur.
Gregory Larkin:
There’s no good playbook. There is no good roadmap for doing that. It was extremely difficult, it is not the same skillset. And the feeling of acceleration that I had experienced in a startup was just not matched when I was… Everything I created inside of a huge company was just a very difficult transition. Thing one. Thing two. What aggravated the fuck out of me during that time, was that all the advice about innovating inside of a huge company, was written by observers, not by survivors. Clay Christensen was a brilliant writer. I think, The Innovator’s Dilemma, is a smart book, The Innovator’s Solution, Rita McGrath, all of these folks, but they had never gone through what I was going through. From an academic third party perspective, the data that they were able to trace, I’m not taking anything away from them, but they weren’t speaking to me.
Gregory Larkin:
And the executives that they had access to, I’m sorry, but the CEOs of a Fortune 500 company, when they’re giving a talk about innovation at Harvard Business School, they’re not fucking throwing chairs in the paneled conference room while they’re there. I can tell you something, once they’re back in the office, they throw fucking chairs. They’re crazy. And I think the visceral level of hostility that the entrepreneur has to navigate, the flashbacks, I got reading all this crazy shit about from the MeToo movement. Not that I was ever on the receiving end of horrific sexual harassment like that, but just the volcanic rage that was just a fact of everyday life in that environment. Was very true, very real. I never saw the sexual harassment side, but the volcanic abuse of power, I saw that all the time. That was the norm, not the exception.
Gregory Larkin:
And so, the reason I wrote the book and I think the thing that struck me, I thought I was taking a gigantic risk by just saying, “Look, the survivor’s story of how to get an idea to come to life inside of an organization, which is some of the least fertile soil for entrepreneurship to flourish, it’s still possible. And this is my experience of it. And if I get killed or blacklisted or whatever from saying it out loud and saying the truth of it, then fine, I’ll be that martyr, I’ll find something else to do with my career.” So I expected that I was taking a gigantic risk by writing this book and speaking that truth out loud, I didn’t expect that it would land well.
Gregory Larkin:
And the extent to which executive leaders in some of the biggest companies in the world were like, “Where have you been all my life?” Has been one of the most miraculous surprises for me. I literally thought not one person with a C in their job title would want to speak to me ever again. And frankly, that’s the audience that embraced it the most, because what I think that the book unearthed for me, was that for every entrepreneur who feels that they cannot get the executive level of support that they need, there is an executive godfather, an executive champion who goes home every night, terrified that they’re going to be at the helm of their organization while it goes extinct, who feels a very real sense of urgency about change and transformation.
Gregory Larkin:
And what’s something that’s been incredibly, I’m very proud of, and it’s been very empowering for me to see it, is that this book has been the thing that they both read together. It’s been the way in which they find one another, it’s been a deliberately, trying to transmit this sonar signal of innovation. And the book has served as that. And so, I hear about these punk pinstripe power couples that happen because I gave a talk at a certain company. So that’s pretty thrilling. That’s been an incredible legacy of it. I’ll take that with me for as long as I’m around. What’s different about the upcoming book is, when I wrote the first book, it’s very much focused on the product as the engine of change, how do you build a product in a giant company that is transformative? Not just, you’re building a big exponential growth venture, but it has an impact on the culture of the organization as a whole.
Gregory Larkin:
Ever since I wrote the book, I haven’t launched very many products. You know what I mean? It’s not really how I operated anymore. I deal at the portfolio level, and I’m dealing at the macro investment level, and I’m helping companies communicate their transformation story to Wall Street, and identifying what are the assets inside of a company’s portfolio of businesses that are delivering that change. And so, I’m zooming, going up a layer with this book. I also have a co-author, I’m writing it with Stephanie Trunzo, who’s I believe she’s the first executive vice president in the history of Oracle. And I interviewed her for my first book. And since then, we became really good friends. Wonderful friends, like co-authors, co-conspirators. But yeah, we don’t have a title yet, but it’s something around transformation in the trenches.
Gregory Larkin:
And it’s speaking, not just to the entrepreneur trying to launch a product, but it’s actually speaking to… Because I have a such a strong degree of confidence at this point, that inside of every organization, there is somebody in the C-suite that feels a sense of urgency around change, feels a sense of urgency around transformation, but they don’t have the playbook. The playbook they have access to, is one that is written by observers, not by survivors. And I’m trying to offer them, this is what the generals who have made this happen, who have also been shot at, this is what they did when they were in the trenches.
Bryan Wish:
Yeah.
Gregory Larkin:
And it’s a little different than what they talk about at West Point. That’s really what this book is for, is how to transform the organization, the entire organization, rather than just a product here or a product there.
Bryan Wish:
Amazing. Well, I think you’ve set yourself up for a road of deep impact for the future.
Gregory Larkin:
I hope so. I’m having fun.
Bryan Wish:
You’re definitely have come alive in this hour we’ve shared, and I’ve really appreciated our time. Where can people find you, your site, your work, your writing, book, all the things?
Gregory Larkin:
So my book is, this is… Sorry, no. The book is, This Might Get Me Fired. My website is thisisgreglarkin.com. And my social media of choice is LinkedIn. That’s where I live, so you can look me up on LinkedIn. And my company is called, Punks and Pinstripes.
Bryan Wish:
Got it. All right. Well, thanks for such a beautiful hour we shared, and excited to put this out to the ether, the world.
Gregory Larkin:
Me too, man. Yeah. Thanks for having me. All right.