Punks and Pinstripes, Reinvention, and the Future of Leadership | Greg Larkin | 705

And welcome, welcome, welcome. This is Peter Winick. I'm the founder and CEO at Thought Leadership Leverage, and you're joining us on the podcast, which is Leveraging Thought Leadership. Today's gonna be fun. My guest is Greg Larkin. He is on a mission to empower entrepreneurs to do their most transformative work everywhere they work, even when it's hard. He's the author of the international bestseller, This Might Get Me Fired. He's a speaker and he's the founder of Punks and Pinstripes, which is a global community of entrepreneurs, intrapreneurs, and punks who support and empower each other. As a side note, in 2006, he was the first person to publicly predict the subprime financial crisis, and then he started a company called Innovest and lots of other interesting things. So welcome aboard, Greg. Anything to predict today? Like, you want to get that off your chest? The end of the world.

I was the head of product at Innovest, by the way, not the founder. Um, uh, I have nothing to predict now that everyone else hasn't caught on to, which is that, um, you know, the AI bubble is a bubble and it will deflate. And, uh, we don't need to talk about that. Everyone, everyone's— that's a fully baked prediction.

Exactly. Yeah, yeah, just right. You could hear it. I mean, it reminds me of the crash of '01 when there was that New York Times cover story on the UPS drivers day trading and all that. And you're like, okay, this is going to end soon and it's going to end badly.

Yeah.

Anyway, back to our regularly scheduled broadcast. So how did you get here? Because this is an interesting spot that you're in. Speaker, advisor, thought leader, punks in pinstripes. Like this was clearly deliberate and planned, right?

Yeah, right. No, I've been planning on this since I was 6.

Exactly. That was the other one, right?

I had a really roundabout career. I started out in a startup. That startup was acquired, and through that acquisition of the startup, I went from, you know, this pirate ship of miscreant innovation to the epicenter of post-financial crisis Wall Street. Truly a pirate inside of the Navy.

Okay.

And, um, and I became the head of innovation at Bloomberg. But I, I think there was a, an understanding that I, I gathered at that moment in time that I think was the beginning of a really zeitgeist moment, which is that there is no such thing as loyalty anymore, not in a corporate environment.

But say more about that. Is that the company to the employee or the employee to the company or all of the above. So nobody's loyal to anybody anymore. That's fun.

You can earn it. There's loyalty for the mission.

Sure.

You know, there's indispensability for spurts, but you know, I was there when Lehman collapsed because if you know, and, and, and we're living in a moment right now where Amazon announced plans to let go of 30,000 employees. They have, they're doing the best they've ever done, Amazon. Right. They're, they're like, they felt like it. They felt like it. They don't have to, they just choose to. And we're living in a post-corporate loyalty economy. Gone are the days where our parents' generation worked for Mother Merrill and IBM, where there was a very, maybe never explicitly stated, but it's like, if you work here for the rest of your life, you will never have to worry about money again. Nor will your children. That is dead.

Yeah. Yeah. That is, that world hasn't existed in probably 15, probably in my lifetime in terms of my career. And yours as well.

So, but I, I think there's, mm-hmm.

How does that influence you as a thought leader? Because for genera— there were 2 or 3 generations, which was the, the implicit contract was do the right thing, work hard, paternalistically, Mother Merrill or IBM or whoever it was will do the right thing and take it. Even if you don't make it to the top, you could kind of stay in the middle and do the right thing. You'll be fine. Everything will be fine. You get a gold watch in 30 years and then, and then you get that pension check, right? Like, and like, it's all going to be good. You can go play golf. Like, so as a thought leader, what I mean, you're kind of going the opposite with punks and pinstripes, which is sort of reflective of your thinking of the way it is today.

So because it now falls to the individual to create loyalty, and it falls to the individual to master the art of reinvention. Once you do everything you were told to do on the first mountain of your career, you ascend into the C-suite, you make a lot of money, you're dutiful and diligent. Invariably, myself included, every person I know who has ever experienced that kind of success, something happens. Death, love, birth, divorce, illness, they get fired. Something shatters their perception that that's the right way to spend the rest of their finite time on Earth, and they have to start over. They're still working, but how do you channel your fire and reinvent yourself in a post-loyalty world? How do you create your own—

and that— and that loyalty that split is sometimes voluntary and sometimes involuntary. Sure. Like you said, 30,000 people at Amazon, they were probably doing a good job and got a great review 2 months ago. Now probably got fired by text or something. Because that's the efficient way to do it. Right? Or an AI bot told them you're no longer needed or whatever. But let, let me sort of flip that a little bit. I think that the loyalty is now more selective. So I know in my work, that it used to be that, oh, here's how a relationship's defined. Greg is my vendor, or Greg is my boss, or right? And once that's defined, once it's defined forever. But now what I have found, at least in my work, is someone that used to be a vendor is now a partner, and someone that used to be a partner is now a client. Like, so you create your own loyalty, and it's not, right, uh, th— this, you know, loyalty to the brand or the logo. But people that you find cool and interesting, the context changes, right? Someone that was a client might be your boss down the road or whatever. Is that more the new norm today?

I think you need a community. You have to build your community. And I think the, the basis of loyalty is community. And sometimes you're building community between vendors and suppliers.

Yeah.

You know, sometimes it's between your former colleague who becomes a consulting partner. Um, but how you— but I think that the, the underpinning bedrock of it is, can you show up and be authentic? Can you create an oasis of authenticity in a world of performative bullshit?

And, and that's a technical term.

Sure. And, and can you be of service who are being, uh, for people where there's no immediate return on investment. It's just like one day, and we don't know when, I'm gonna need this back, you know, or not, or, or I might not need it back.

It's not a quick— it's not so measured sometimes, right?

And, and I think having community is the bedrock of loyalty and the bedrock of reinvention, because the forcing factor that makes you reinvent is an inevitability. Into the—

stay there for a minute, because when I think about community and you think of it on like a continuum, you have associations, and that was usually sort of a professional guild, the Association of, uh, whatever, physicists or engineers or whatever.

That's not what I'm talking about, right?

But then you might have on the other end hobbyists, people that play frisbee. You're going more psychographically with punk and pinstripes, right?

Absolutely.

What that was about, because it wasn't just I'm an alumni of an Ivy League school or something like that. Like, how did you find— you created Punks and Pinstripes because you wanted that community, so you created it. But how would you define the members of that, or what the type of people that are attracted to something like that?

They are all people who are climbing the second mountain of their career. Now, that doesn't mean they've left their job. Some of them are staying inside of huge companies and reinventing themselves and doing their best to be an engine of transformation there.

I, but let me push on you as a marketer. So when you say the second mountain of their career, I sort of get a picture of that in my head. But then if I were to make a note to myself, create a campaign to find people on the second mountain of their campaign and go to LinkedIn, that's not a check the box, right? Like, like it's really hard. It's a company, like, whoa, we're like, did LinkedIn leave out that box? Like, how do you, what are the signals that you would know or find?

Yeah.

Whatever.

So it's a thing where you have to, it's a program of attraction, not promotion. And that's a very important thing to understand. What I have come to realize is that, that moment where this first mountain is no longer satisfying and you feel a sense of urgency to start reinventing yourself and climbing and finding what's next and climbing that next mountain, that's almost a ubiquitous experience in every successful person's life. It's not something that they advertise. It's something they go through quietly. And the, the pain of it is that you very often are left borrowing first mountain communities, first mountain tools to climb your second mountain.

'Cause that's, but that's a bit of what got you here. That's what you know, right? If you know that I'm surrounded by people like this and that's gotten me here, let me take them to the next mountain. But they might not be the mountain climbers for the next mountain.

Sometimes I think most of the most damaged professional successful people I know are people who had the second mountain pang and like just shoved it down and were like, can't allow that to surface, can't acknowledge that, must power through. But I think the clarion call is it's up to me as a marketer to share the second mountain reinvention journeys of the most notable people who have climbed that second mountain. And share that of our members in Punks and Pinstripes. Because most great reinvention, most great innovation starts with someone where it's not just they were like born a genius. No, they very consciously walked away from safety, security, stability because it wasn't fulfilling and it felt like golden handcuffs. Cindy Gallup, the band Public Enemy. Duff McKagan. Duff McKagan, the bassist from Guns N' Roses, is now running a billion-dollar hedge fund. You know, you, you could start the, the, the movie about the, about, about Steve Jobs at him meeting Steve Wozniak and starting out in a garage. That's not where you start the movie. You start the movie where he quit his job at Atari.

Exactly. Yeah, yeah, yeah, yeah.

You know, where he walked away from Xerox. That's where you start the movie.

Right, right.

And then what happened? And then who did he allow into his life? And then how did he evaluate the capital that was available for him?

Yep. So I wanna, I wanna segue now into, as a thought leader, right? You've got this, these ideas, you've got these concepts, you've got these passions. How do you decide there's a business model here or not? And how to, like, you could go back to corporate, God forbid, right? And go do all that. But like, how did you decide like, okay, here's a thing, there's a market, and here's how I'm gonna monetize it in a way that feels right for me.

Couple things. Number one, I started with very radical differentiation, both in idea and in tone.

Mm-hmm.

I think a huge volume of thought leadership is focused on first mountain problems.

It's probably right. Yeah.

I'm talking about second mountain problems, which is decidedly ubiquitous but unsexy. The people who are in that phase of their life are older, which is not the prime demographic. It's not necessarily what Fast Company is talking about on the front cover.

But isn't it also in, in the sort of, you know, hashtag first world problem? Boo-hoo you, you made, you know, $20 million, but you're, you know, you left your soul at work.

No, no, that's not true.

Okay.

Um, it's a, it's a, it's an emotional problem. It's an existential problem. It, it, everyone experiences it. Everyone, whether you have, are able to act on that realization with money and whether you have prepared for that inevitability, that varies. I was doing great when I quit my job at Bloomberg, but I wasn't rich. I had to work. I had to go and figure out what was next. Um, I definitely had financial stress with that decision.

Right. You know, but how did you figure out then that the business, the, a, there's a, because sometimes there's thought leadership that's out there. That's a solution in search of a problem. How did you realize that this is a real thing and it's validated the business here?

Let me back up a second, Peter.

Sure.

We live in a world where experts without experience sell advice without accountability.

That's the 24-year-old life coach.

It's everyone. It's the Harvard professor who speaks about innovation, who's never innovated a goddamn thing in their life. It's the pundit. It's the inability to differentiate between punditry and analysis.

Okay.

It's, it's, it's fake data describing fake hero stories, describing made-up story arcs. There's a guy, I'm not going to mention his name. He's one of the most renowned business authors. Authors in the world. Everything he writes about is fiction, literally fiction about imaginary consulting firms and imaginary hero journeys. It's like, meet Meg. Meg runs a brownie factory in Spokane, Washington. Meg is struggling, but watch me coach her through to cushing. There's no— and they're like, they're clear, like, who's benefiting from that? You know, and the reason I say that, Peter, is that—

aren't they usually done in the form of a parable? Meg is a mouse, right? Or Meg is even more offensive, right?

Like, who are you being of service to? You're being of service to yourself, right? Um, but I think the ability to be honest about how much pain you're going to endure when you're solving a really hard, really ubiquitous problem and you're gonna have to figure out a way to get through to the other side, and you're not afraid to show your scars. Any thought leader who can speak from the first person singular about, dude, this isn't easy. I'm not gonna feed you some fake Easy-Bake recipe about how to solve this problem and get rich.

I find, and I hear you on the, you know, Meg the Brownie CEO, whatever, but I think a lot of the thought leaders I've been fortunate enough to work with and know, when you really get down to why did you do this? Why did you write this book? They wrote the book that they needed most, right? It was almost, you know, they wrote the book that they would've wished was there, or it's the journey they took, or it's, you know, it's something around they needed to solve this problem. Once they solved it, oh yeah, I might as well put in a book 'cause others could benefit from it, right? Versus let me craft a hypothesis on a book that will sell because middle managers in this space struggle with having difficult concrete, whatever.

I think that's true to a point, but I was the global head of innovation at Bloomberg. It was my job to launch. I had to give birth to a 13-year-old every 6 months. That was my job. You know, and, and Clay Christensen, smart man, good man, may he rest in peace. He had no idea what my life was like. Despite having written The Innovator's Dilemma, he had no idea the magnitude of obstructionism that I had to navigate in that role. He had no idea that the real hard part was not product-market fit or technology fit. It was that for everyone who wants things to change, there are 3 very powerful people who want things to stay the same.

Because of their own agendas or motivations or whatever the case may be.

It ranged from total craven self-preservation and self-promotion to risk aversion. I don't think— I think this is going to get us all killed. You know, some of it was legit, some of it was illegit, but like, honestly, the job was to navigate the obstructionists. The job was not getting Agile right.

Right. And there aren't a lot of business books on how to navigate the obstructionist, right? Which is something—

No one wrote it because I don't, I don't, everyone who was the, like, on the stage of Thinkers50 was on the outside looking in at what they thought I was going through, you know, and, and, and God bless them. It's like, you know, if I can build up a follower base and leverage my, my, my, my relationships with HBR. This seems to be where the market is going. So I'm going to just pontificate on it. I'm going to win the punditry prize.

Yeah.

I don't think that's actually doing any service to the person who really owns that problem and has to solve it. And I also saw that that was a gigantic opportunity in my own book and in my own life to speak with rare honesty and integrity about what it's like when one of the wealthiest, most powerful humans in the business world throws a fucking chair across their conference room because they don't like your prototype. Yeah, like, let's just start there. Like, start in the room when that happens and, and, and the, the glass walls of the conference room like bang because he threw a fucking chair, right? I'm not saying who this person is, people can interpolate.

You probably have, you might be driving one of those products or have one in your pocket. Let's leave it there.

Let's just leave it there. But like, what do you, what are you doing after that? You know, how do you go back to your desk after that? How do you wake up the following morning and go back to the office after that? Start there. 'Cause that's actually what's really going on.

Yeah. But then they throw the term around like genius, which is like French for a-hole, right? Like, so that's not genius. That's horrible behavior. That's unacceptable. Sure. Like if most people did in most contexts you'd be arrested, right? And there would be real—

no, that's, that's actually, it's assault. It's legally, it's actual assault, right?

So you would be right. Most people that did that at a PTA meeting or their regular whatever, they'd be banned. Yeah, they'd be banned, handcuffed, you know, pushed out, never to work. You'll never work in this town again, right? But yeah, yeah, yeah, interesting. All right, as we start to wrap here, what are the things that you're toiling with today that we might see, uh, see, see you give birth to, either as a teenager or not, as a 30-year-old. I just have this vision of you giving birth to like bar mitzvah boys or something. I don't know, it's a beneficial—

they come born with payas.

Yeah, exactly, exactly.

Uh, a couple things. So we do a salon in New York. It's limited to 50 people. It's a great monthly event where we interview some of the most famous people in the world about their own reinvention journey.

Right.

Very good. Um, our next one is on the 22nd of January. Not sure when this episode's going live, but it's with Peter Thunney. Okay. And then on February 5th, we're talking to Stephanie Trunzo. She's the CEO of, uh, Merge. She used to be the CEO of Oracle Healthcare. How she left Oracle and started Merge and what that journey of reinvention is, is incredible. So we do that on a monthly basis and very exciting news. We just got picked up by the, um, Live from Tomorrow podcast network. That's run by Matt Hooper. Matt Hooper is, uh, he's been to a bunch of our salons and heard a bunch of our interviews. And, um, we are going live with our Punks on Pinstripes podcast.

Very cool.

Very soon. The other thing that we started last year in stealth mode and are now not stealthy about anymore is that we have amazing retreats and they come in two factors. One is like a reinvention retreat where we all go to this beautiful house in the Catskills and it's 3 days and 2 nights, and it's kind of dealing in very intense ways with where are you trying to move away from? What are you moving toward? Why is it hard? How can we help? And, uh, this coming summer we're doing a creative retreat in Italy, 5 days. We're renting a giant, beautiful farmhouse. You wake up, you meditate for a half hour from 9 until 1. It's total silence. You can just write or paint or draw. Or build the app that has no business use whatsoever, but you can't get it out of your head. And, um, so that's coming up.

Cool.

The red thread that ties all of these things together is the greatest innovators, transformations, breakthroughs of our time come from people who have had the courage and focus and chutzpah to reinvent themselves and get out of the comfort zone.

Cool.

Um, and we just— it's, it's my job and my calling to, uh, create space for them to be able to do that and to help one another do that. Great.

Well, appreciate your time. This has been a lot of fun, and I wish you the best on all the things you got going on. Thanks. Thanks, Greg.

All right, my pleasure.

To learn more about Thought Leadership Leverage, please visit our website at thoughtleadershipleverage.com. To reach me directly, feel free to email me at Peter at thoughtleadershipleverage.com. And please subscribe to Leveraging Thought Leadership on iTunes or your favorite podcast app to get your weekly episode automatically.