A Rebel With A Cause (And A Community), With Greg Larkin

Rebels don’t just break the rules—they redefine them. Greg Larkin, founder of Punks & Pinstripes and author of This Might Get Me Fired: A Manual for Thriving in the Corporate Entrepreneurial Underground, joins J.R. Lowry to explore what it means to be a rebel with a cause in the corporate world. They dive into why true innovators struggle inside big companies, how disruption often leads to transformation, and why some of the most game-changing ideas come from those who refuse to conform. Greg shares his journey from Wall Street to building a movement that empowers leaders to challenge the status quo. Ready to embrace your inner corporate rebel?

Check out the full series of Career Sessions, Career Lessons podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/greg-larkin/.

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A Rebel With A Cause (And A Community), With Greg Larkin

CEO Of Punks And Pinstripes

This show is brought to you by Pathwise.io. If you want to take control of your career, visit Pathwise and join our community today. Basic membership is free. My guest is Greg Larkin. Greg is on a mission to empower entrepreneurs to do their most transformative work everywhere they work even when it’s hard. He is the author of the international bestseller This Might Get Me Fired, and an international keynote speaker.

He is also the founder of Punks and Pinstripes, a global community of entrepreneurs and punks who support and empower each other. In our discussion, we’re going to be talking about the mission of Punks and Pinstripes, Greg’s broader career journey, his book This Might Get Me Fired, and why it is so hard to be an entrepreneur and for companies to innovate. Let’s get going. Greg, welcome, and thank you for doing the show with me.

Thanks for having me.

You are the CEO of Punks and Pinstripes. It’s a great name. Tell us about it.

Punks and Pinstripes is a curated executive community for business punks.

What do you want to do to be a business punk?

What It Means To Be A Business Punk

It’s more a psychographic than it is a demographic. For people who are successful in their careers, either as executives in big companies or as entrepreneurs, there’s this transition you hit at a certain point where you realize that the definition of success that you’ve pushed yourself toward isn’t your own. It’s a paradigm of success that’s not fulfilling anymore. It’s the diminishing returns, the next promotion, the next bonus check, and the next thing.

All of those things, at a certain point, are like, “Is that what I want to be doing with my finite time here on earth?” I think a lot of the greatest breakthroughs of our time happened in the aftermath of someone experiencing that transition, the startups that they build, or the ways in which they transform the companies that they lead. It’s very hard to find one another. It’s very lonely when you find that you are that person. A lot of executive communities that are out there diminish that feeling. They’re much more about pounding your chest, telling everyone about how you’re crushing it, and conforming.

Punks and Pinstripes is the opposite of that. Number one, people who have experienced that tend to go on and do the most important work in the world. They solve the hardest problems in the biggest companies. They leave those companies to launch ventures that were never possible from the inside. We bring them together, help them empower one another, and give them the gift of solidarity and compassion. We have a few rules about how we make it work for one another. That’s what it is to be a business punk.

How many of your members are entrepreneurs? How many are people who are in bigger companies?

That’s a hard question to answer and I’ll explain why. When most of our members start as members, they are in the C-suite of the biggest companies in the world. Within 2 or 3 years of joining Punks and Pinstripes, they almost always leave and go on to do the best work of their life. A handful of them stay and a handful of them switch. We have a member who went from being the top designer at Google and transitioned to Dow Jones. That was exciting.

It’s the wrong question in terms of whether they’re entrepreneurs or corporate executives because, in reality, it’s this huge revolving cycle. They go to the top of a company, they leave, they launch a startup, the startup gets acquired, and they’re back in a company. That’s the cyclicality of a punk’s life. At some point, they’re like, “I think I’m good. I’m going to focus on being deliberately small.”

How do you decide who becomes a member and who gets turned down?

The Exclusive Membership Criteria Of Punks & Pinstripes

Only about 2% of the people who apply get in. That’s not some elitist thing. I can be very concrete about why. We have something called Help a Punk. We have dinners, and every member goes to a dinner at least once a month. Those dinners are always fewer than fourteen people and they’re always home-cooked in someone’s house. We don’t ever want to have someone come to a Punks and Pinstripes dinner and be like, “McKinsey took me to this restaurant two weeks ago.”

If someone just took on a new job and was concerned about burnout, the question we asked the person who’s in Help a Punk is, “What’s the hardest thing you’re wrestling with that’s the hardest for you to talk about?” He’ll say, “Burnout for me is not like I need a vacation and some time with my kids. Burnout for me historically meant I was an inpatient in a psych facility. I push myself to very unhealthy levels. I started this new job and it’s thrilling and exciting. There’s so much pressure, so much stress, and so many expectations from me. All the triggers that are pushing me toward burnout are right there. They’re firing on all cylinders.”

I say we’re super selective because there are very few executives who can sit in that conversation and honor that space. I don’t want someone going into that conversation where someone is as senior as that, and they’re being as raw and vulnerable as that. I don’t want someone saying, “You’ll never guess who I had dinner with.” When someone says something as raw as that, that’s a sacred responsibility for all of us.

The vetting process is pretty rigorous because I have a deeply felt obligation to make sure that everyone who’s coming into the group can amplify and enhance the experience for everyone who’s already here who shows up in that way. There are very few people in the C-suite who cannot. That’s true. There’s a lot who need us, but there are very few who let themselves be that person.

What does the application process look like and what are some of the red flags that push somebody out in the process?

The application process is evolving, first of all. Once a quarter, we would have an open application process. The group is in New York only. We have a handful of members from out of New York, but all of our events are in person and they’re pretty much all in New York City. Once someone applies, I’ll talk to them and ask them the same question we ask in Help a Punk, which is, “What do you want Punks and Pinstripes to help you with that you cannot find help someplace else?” What I’m listening for is someone being honest about something they’re struggling with.

What I usually get is, “I’m a senior vice president and I want to become an executive vice president. I’m on the precipice or I’m in the C-suite and I got shafted on my bonus this year. I feel like I’m being boxed out of certain corporate decision-making.” There are questions that you can ask to go a layer deeper, but not very few people do. If that’s the case, there are a bunch of groups that can help you get what you want. That’s not why this exists. I’m happy to send you along a bunch of other groups that would be perfectly happy to get here.”

How did you decide to do this?

From Wall Street To Building A Community

I was that executive. My startup was acquired when I was young. Through that acquisition, I wound up working on Wall Street for a long time. Eventually, I became the global head of innovation at Bloomberg. I was such a cultural outlier there. It was this weird paradigm where on one hand the products that I was building or the businesses that I was transforming were indispensable. The company and the customers we serve a hundred percent invariably need it. I’m not the person that they were building the C-suite for. Do you know what I mean?

The executive was such a cultural freak. That was simmering for a while, but the money was good and it was very prestigious. I had access to people and places and things that were very ego-massaging in a very superficial way if that makes sense. I slowly started to hate myself and hate what I was becoming. At a certain point, I couldn’t ignore it anymore. I said, “I quit.” Not only did I quit, I wrote a book about it, This Might Get Me Fired.

You preempted yourself there. You took yourself out of your own job.

I did. There are a lot of those people when you go into a company like Bloomberg, Chase, or Google for that matter. Very often, the people who are inventing or creating the most meaningful products or transforming old businesses that are in deep crisis situations and need to be modernized are not people who are focused on self-preservation and self-promotion. They don’t have a sense of complacency about modernity.

They don’t rest on their laurels. They’re motivated by impact. They need the feeling of acceleration. What tends to happen when you are that executive and you raise your hand and you say that about yourself is, “Cool. Boston Consulting Group is having an innovation summit. Why don’t you go there? We’ll send you there.” You might get tactics there, but you’re certainly not getting compassion and solidarity. There’s this thing that like everything that made me undateable in high school made me a valuable currency in the punk scene in New York.

Everything that made me such a cultural outlier and outcast in executive leadership on Wall Street, once I started to own it, find my tribe, and build a community, I was like, “This is a valuable currency and there needs to be someone who creates that category of a business punk.” How do you know to say I am one of those? How can you find the room where the rest of them are? Where are they hiding? That was always my sense of mission when I started Punks and Pinstripes.

You say you had a more traditional start to your career. You studied International Politics and Economics, right?

Yeah.

What did you foresee yourself doing at that point?

I had no idea. When I studied International Relations at McGill University for my undergraduate degree, I went into my first class thinking it was going to prepare me for a job in which I traveled a lot and how to comport myself and other cultures around the world. I had no idea that International Relations was the study of war, diplomacy, and statecraft. Once I did learn that that’s what it was after I flunked a few midterms, I fell in love with it. At that time, when I graduated from McGill, I wanted to go and work for Doctors Without Borders or something like that. That’s what I wanted to do. I did wind up doing that.

What were some of your early roles?

My first job out of college was as a community organizer for the New York Blood Center. I was responsible for organizing blood drives throughout the borough of Brooklyn, which in the year 2000 was gentrifying but not gentrified. I loved it. It was an amazing job. I was on the front lines of 9/11 because of that job, which was scary and hard, but taught me a huge amount about myself. That was like my baptism into adulthood, which was being a first responder when that happened. You’ll never hear me say a bad thing about that job. It was incredible.

My master’s degree was in International Economics. I didn’t know what I wanted to do with it, although I was very interested in international development. I would have loved to at the time work for an emerging market fund. That was my goal. Life was making other plans. I studied in Scotland and I wound up working for a nonprofit called Mercy Corps. It still exists. I wound up running their micro-credit fund. Microfinance is a tool in development economics where a bank will make very small loans to small businesses in very poor communities and poor countries.

The beautiful thing about that job is my job after that, and this is where my career in its current incarnation started, which was at Innovest. They hired me in 2005, the peak of the housing bubble. I had come out of microcredit and I knew a lot about like, “How do you lend money to poor people? What’s the fine line that separates access to credit from predatory lending?” They were like, “Do you think that kind of analysis would be valuable for telling some of our hedge fund clients whether this housing boom is sustainable?”

I’m like, “I don’t know. I know some of the data that I would need to collect to do that analysis. If you can help me find it, I can give it a shot, but I don’t want to overpromise. If you’re comfortable having me move back to New York and take a stab at it and see if the things that I did to analyze banks in Indonesia can apply to Neiman Brothers, I don’t have a good answer, but I’m happy to try.”

Predicting The Subprime Mortgage Crisis At 28

Maybe it’s luck, like being in the right place at the right time. That was the first public prediction of the subprime mortgage crisis. Some of our clients are huge. We’re long mortgages, first of all, and turned their position to short on the back of that first report. That was unbelievable. That’s when I’m like, “This is where I want to be.”

Is it the impact, or was it the startup environment?

Both. I loved it there before. That report came out in June of 2006. No one believed us at first. It fell in the forest internally. It had a huge amount of support. It was a red flag how much the biggest banks on Wall Street, many of which are no longer with us, tried to get me fired because they didn’t like the conclusions. The way in which they breached ethics violations prevents the side of the house that deals with analysts. A lot of those banks were also clients of ours. They’re very explicit in canceling our contracts because they didn’t like that report, which is illegal. That’s not allowed to happen. No one gave a sh*t.

It was the time. Even MCI, WorldCom, Enron, and all those things that created Sarbanes-Oxley and some of the other things that predated the time period you’re talking about. They came out of the incestuousness of the Wall Street analyst business model prior to the dot-com bust and all of the situations that happened with the Enrons out there that necessitated having tighter controls of Wall Street and tighter rules of corporations too.

Very much so. Innovest was a bunch of punks and misfits. Our founders intentionally left Wall Street to start Innovest. They wanted people who had weird backgrounds to analyze things that were off the radar and for us to find mispriced and actionable global megatrends that no one thought to think about. We had a suit and tie in the closet for when we had client visits, but a lot of our clients loved the fact that we had this miscreant corporate or startup culture.

I’m still incredibly close friends with a lot of people I worked with back then who did incredible things. I felt an incredible sense of comradery with that crew. It was us against the world. I was also 28 at the time and that helps, but we were going to teach the suits on Wall Street a thing or two. They didn’t get it. We had this irreverent attitude. When we make this huge call, which was the first public prediction of the biggest financial crisis since the Great Depression, it turns out that being punk was correct. It turns out flipping the middle finger to everyone in these giant glass towers that surrounded our office in Midtown, and it turns out we were right.

It was because we were unseduced by everything that Wall Street was seduced by that made us right. We were not the people who were smart enough to do it. We’re the only people who were non-conformist enough to say it. That was so satisfying. When we got acquired, I thought, “Great, we get to do this at scale.” That’s not how it played out. It meant that you’re now reporting and your boss is the person who you were up against in your past life saying, “Wall Street cannot figure this out. Guess what? You don’t work at Wall Street. You work on Wall Street now.”

I also had this early success. I think that instilled in me such a huge amount of hubris and ego that I was unmanageable out of Innovest. I couldn’t believe the camaraderie of these 50-year-old men with their Wharton degrees who believed that I needed to be tamed, disciplined, and focused. I was like, “How dare you? Do you know who I am?” I was an impossible employee. I was full of piss and vinegar. I hated this and I hated them.

The aspect of hard from maybe what you were like to manage at the time. There’s also the factor of the inconvenient truth. So much of the corporate world wants to stamp that stuff out, to bury the contrarian report, to bury the thing that says that they’ve been focused on the wrong things and that their perspective on something is inaccurate. It’s protectionism. So much of corporate life is about protectionism.

That’s true. Unfortunately, a lot of corporate hierarchies are distorted to insulate people with power from ever being told they’re wrong. It can be abused for sure. Equally, there are ways to be heard. That’s not going to go away. No matter how healthy the culture is, egos are what they are. People who don’t like being told no leverage the spoils of seniority in order to never hear the word no. There are going to be situations that arise where they need help.

Crises happen, earnings falter, and new startups come in that are leveraging new technology with new energy and new ideas, a different business model, and a different cultural paradigm. They start stealing all your clients. There are vultures out circling always trying to kick out your leadership or acquire you for as little money as possible. In the case of Innovest, I was acquired and we were promised everything, and all of those promises were broken very quickly.

At the time, it felt like there was this layer of insulation. In retrospect, as I became more senior, my eyes were a lot wider in terms of how hard it is and how those few moments where it’s like, “If we can just stabilize this and get this thing that we built to run on some flywheel with some degree of predictability, we can capitalize on this weird moment of ceasefire and the barrage of crises that constantly dominate our everyday. Can we somehow find a way to make this scalable?”

I have a lot more appreciation for how important that is and how hard that is. Something that a lot of leaders don’t communicate effectively is why they’re thinking about it in that way. This is one of the few moments where it is business as usual. Can we just capitalize on it because we are going to have a new sheriff in town and another fire to put out very quickly?

You have to seize those moments when you do have the tailwind or the conditions for success and race ahead. At some point, you know you’re going to get kicked in the face and knocked back, and you’ll get focused on dealing with that for a while. You lose that momentum, but you have to seize it when you get it.

That’s true. Something that emerged from that is there are three layers of any company. There’s the investment layer, the portfolio layer, and the product layer. In a startup, you don’t have that. The product is the investment layer. The more successful I was and the more I went from product to portfolio, and then eventually into the investment layer, the less I liked it, but also the more that I found leaders in that environment who wished they could go back.

They got so jazzed up by what was happening in the trenches. The idea that they could work a 90-hour week, building something for launch, writing code, taking it out into the market, and tweaking was so thrilling for them. It was the thing that they never got to do anymore and they missed it so much.

There’s a simplicity to that. As you move up in an organization, you have to think about so many different things at once. You don’t ever get the focus on anything in the way that you do when you’re down in the trenches. A lot of people miss that.

They miss it hugely. It took me a while to figure this out. I probably figured it out after I left Bloomberg and was doing consultant work for Google. Your first job as an innovator in a company is to find that leader. If you’re trying to move the needle and you get your energy from finding important problems and solving them, there’s going to be someone in executive leadership who is willing to use their political capital so that they can relive their youth through you. They will fight for you.

Greg Larkin: Your first job as an innovator is to find that leader—someone in executive leadership willing to use their political capital to fight for you.

It’s important and it’s very hard to have any success if you don’t have that. It’s more than a sponsor. It’s someone willing to use their capital to clear obstruction from your path. That’s a very hard person to find but they exist. I think the people who are those leaders don’t know how to tell the world that they are those leaders. It’s a very hard thing to signal.

You could be a BS artist and tell people you can do it and you cannot. You can overstretch your own capabilities and fall flat on your face. It’s why a lot of people don’t necessarily even try to do that because it’s risky. As you said, you’re using your own political capital, and there’s only so much of that that we all have.

You were the global head of innovation for Bloomberg, which is a very innovative company that has had massive success over the last four decades or five decades or whatever it’s been at this point. I’ve always thought that even in a company like Bloomberg, it’s a hard role to be in because you’re constantly on the outside of the core by design, but it makes it that much harder to work in those environments. What was your experience being in that entrepreneur model?

Corporate Innovation And The Struggle For Change

It was extremely hard. Every company is going to be split in half between disruptors and preservationists. Some people want to do things and use power and accumulate power in order to change the world and challenge the status quo. There are going to be others that want to use their power to keep things the same. The bigger you are and the more successful you are, the more that the senior ranks of a company are occupied by preservationists who have no other interest. That becomes their job.

It’s a constant state of attacking, defending, and maintaining. If you find yourself in a position of innovation where it’s not simply that you have to put points on the board where you’re launching new businesses and making money from them, or you’re reversing the decline of mature business. That’s not your job. Your job is to overcome the obstructionists that are going to challenge you, who feel threatened by you, whose only motivation is self-preservation and self-promotion.

They don’t view what you’re building like, “Is that solving a problem that we couldn’t otherwise solve? Is that serving a need in the market that can hurt us if someone else solves it and not us?” That’s not how they see the world. I understand that after that experience better than I did during it. It’s this amorphous like, “Why am I always pissing people off when I’m successful? Why is it that when I do something and it works, I have more enemies than friends?”

So much corporate shod for you.

It is. I’m like, “Why is it that if I do something mediocre and don’t do well, people are like, ‘I love that PowerPoint deck?’” The fact that it’s a PowerPoint deck is the problem. There’s this paradigm where their definition of me winning meant that I had unfettered access to a team of McKinsey consultants. I’d prefer to have three good full-stack designers, a good product manager, and access to some software or someone who’s a good developer. Innovation has matured a bit, as well as the discipline since I left. It’s hard. It’s an incredibly difficult job to have.

One of the biggest problems about it is the way innovation is taught by people who have never innovated. A lot of the academics that dominated what this is supposed to look like have never been accountable and responsible for building new things and new companies in their life. They observed it from the outside astutely, but not in a way where they understand that the job is not like, “What’s the right level of autonomy for an innovation business unit?”

Who cares is the short answer. That’s not the problem that you need to solve. The problem that you need to solve is that the more you win, the more threatening you are. How do you anticipate what the obstructionist defense is going to do and call the right play when you encounter it? That’s the job. If you’re a great innovator and a startup and you take on that job and you don’t know how to read the obstructionist defense and leadership, you will fail 100% of the time.

Why Most Startup Founders Are 45 Or Older

I’ll say something else about that paradigm of obstructionism. Sam Altman was an employee of Google. Elon Musk worked at Scotiabank. Many of the members of Punks and Pinstripes are undeniably incredibly successful unicorn founders. The average age of the most successful founders, including in Punks and Pinstripes, is 45 when they’ve left the executive leadership team of a giant corporation.

This image of this dorm room startup founder becoming Mark Zuckerberg on Facebook is not true. Most of the best founders of our lifetime were spat out of a politically dysfunctional company that didn’t know how to harness their power. The more I’ve seen that and also seen the people who are excellent at it, that’s what Punks and Pinstripes are all about. That’s who business punks are. It’s when it’s like, “There’s a return on invested capital, an invested labor of my own life. I’m going to make smart decisions at a certain point about how to maximize those returns.” A company that’s going to coddle obstructionism is never going to realize what those returns are, regardless of what Ivy League innovation expert they bring in, they still have to talk.

You said at one point, “I’m done. I cannot do the corporate world anymore,” and then you wrote your book.

Writing ‘This Might Get Me Fired’

I had a nervous breakdown first and then I said, I’m done. The book was written about two years after I quit my job at Bloomberg. When I left, I started to do product consulting and innovation consulting. Viacom was my first customer, then PwC and Google. I ran a product studio that was a joint venture between PwC and Google. As I was doing that, I had this fantastic realization that all my scars were my superpower. The fact that I was coming at this from someone who survived it as a consultant, and I understood what the real problem was and why certain products were dying that were perfectly great products and others were thriving that were terrible and mediocre, not good.

First of all, the book started as a journal. I’m a writer. I wake up every day and I write. I cannot help it. It’s how I process my thoughts and my feelings. I just write. I inherently write. I don’t leave the house without a tiny little pocket-sized pad. If I’m on the subway, I’m writing. I’m a writer. I started to share some of my thoughts and the things that I had written about my experience as an innovator at a huge company with other people who were going through the same thing.

You’re seeing this with clarity. There’s a market for what you’ve seen and experienced because I think the people who have written about it are not the people who have survived it. Writing a survivor’s guide to it is a very different thing. It’s like writing the innovator’s dilemma when you’re sent to Harvard Business School. That was how it started, but I think that the key takeaway from the book is that if you’re going to do this, you need to figure out how you’re going to manage the conflict that innovation creates.

Greg Larkin: If you’re going to be an innovator, you need to figure out how to manage the conflict that innovation creates.

How can you find the right allies? How can you make it a win-win outcome? How can you be honest about everyone you work with who’s in a position of power and authority? How do you have that conversation about if you’re going to support me while we do this, I want to be upfront with you before we start about some of the ways in which the fights you’re going to have to have on my behalf if this works. How do you build anti-fragile innovation?

You’ve described the book as perhaps your proudest professional accomplishment. It sounds like the book hit a nerve with people. Why is that?

The Biggest Challenges Of Corporate Innovation

It’s because I insured the goddamn thing. I was clear about one of the biggest challenges of innovation which is die on the vine syndrome. Companies launch great innovations all the time that die on the vine. Why is that? Who kills it? Why did they kill it? The hard part of innovation isn’t building the thing that is the right fruit. The thing is how do you get it protected so it doesn’t get killed? Everyone who had an idea of what that looked like was someone who had never had to do it for a living.

The book doesn’t read like an academic textbook. The book reads like a memoir. I tried to capture that. It feels like you’re describing the scene of a movie. In reality, I was in the rooms where big decisions were made. I was in the rooms where the subprime mortgage crisis is. The house council of Lehman Brothers tried to get me fired for predicting what ultimately was going to kill the bank. I’m not saying that to be boastful.

I’m saying that there are not many people that are in the situation room, so to speak, in the biggest companies in the world where it’s like, “Are we going live with this or not?” I was, and I got to see what happens when the decision is made not to. Not only not to, but we don’t like that kid’s attitude. We’re going to fire him or we’re going to suffocate him or we’re going to smother him with this onslaught of Accenture, McKinsey, and Boston Consulting Group because we know that they’re going to dilute it, repackage it, and turn it into something so banal, mediocre, and expensive.

By the time it is presented for the annual business meeting, it’s going to look like every other piece of dog sh*t that’s come across our business, then we can say no. That’s an obstructionist play that’s designed to look like, “This is great. We have a gift for you.” I’d lived through that over and over again. I was completely candid about who those people are and how they’re motivated, which is very different than saying, “One strategy that you could deploy is this and another strategy.”

Let me back up a second. I wanted it to be the Kitchen Confidential and innovation book. When Anthony Bourdain wrote the Kitchen Confidential book, he could have written a cookbook. He didn’t. He wrote a book about what life is like inside the most elaborate kitchens in the world. What is it like to be a chef there and this subculture of miscreants and freaks, and this camaraderie in this thing? The product studios are very weird places with very weird people who you would not expect to find at a place like Goldman Sachs, BNY Mellon, PwC, or even Google for that matter.

If you want to know where the punks, freaks, miscreants, and weirdos are, they’re probably there. If you are that person, listen to how they got through it. That’s who is going to get you through the hell of it. That’s why the book resonated because it was the truth. There’s something that was said in certain situations. It’s like, “The advice of a survivor is a lot stronger than the advice of an observer.” It’s personal experience-based. It’s compassionate in a way that observation-based advice cannot be.

The comparison to Kitchen Confidential is good because that book laid it all bare. No holds barred. It wasn’t completely a burn-the-industry-down buckle. It brought you into the reality of it.

By the way, I didn’t want to burn the industry down. Bloomberg is doing great. That there was some degree of incompatibility between my attitude and their culture is true. I wish them all the luck in the world. They’re doing fantastically well without me. I say that punk is an act of love, not an act of war. What I mean by that is it is an incredibly gracious act if you’re a little bit irreverent and a little bit punk rock and you are the business punks that I’m describing to say to the leaders who have more power than you. I’m saying this because I want this organization to be better than it is.

Everyone who knew what I know and saw what I saw would rather leave and deprive you of the value you could have knowing what I’m about to say but this needs to change. The power paradigm around this transformation needs to change, the culture needs to change. If you’re not willing to do that, I completely respect that, but I’m not going to waste my life here and you don’t need to waste yours.

That’s not an active like let’s burn the curtains down. There are a lot of people who were here before and who will never give you an opportunity to embrace tough love. That’s not an easy thing to say. It’s not an easy thing for a CEO to hear, but it still needs to be said and it still needs to be heard. Do it anyway.

What’s ahead for you? What’s ahead for Punks and Pinstripes?

The Future Of Punks & Pinstripes In New York

We’re growing in New York. We’re looking to get to 75 members by the end of this year. We’re capped at 200. Once we hit 200, there will never be a 201st member. We have something powerful and it was fed by a lot of experience and history, but that’s what we’re doing. My full-time focus is on making sure that everyone who needs this is here and enhancing the community for everyone who’s already here.

Thank you for doing this. It was an interesting journey from entrepreneur to entrepreneur to Punk and Pinstripes.

It has been interesting and I appreciate you making the time. Thanks for inviting me.

Have a good day, Greg.

Thank you so much.

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Thanks to Greg for joining me to discuss Punks and Pinstripes, entrepreneurship, introvership, and his broader career journey. If you’re ready to take control of your career, whether it’s an entrepreneurial journey, an entrepreneurial one, or otherwise, you can join the Pathwise community today. Basic membership is free. You can also sign up on the website for the Pathwise newsletter. Follow us on LinkedIn, Twitter, Facebook, YouTube, and Instagram. Thanks.

Important Links

• Greg Larkin
• Punks and Pinstripes
• Greg Larkin on LinkedIn
• This Might Get Me Fired
• Kitchen Confidential
• Innovest
• PathWise on LinkedIn
• PathWise on Twitter
• PathWise on Facebook
• PathWise on YouTube
• PathWise on Instagram

About Greg Larkin

Greg Larkin is on a mission to empower entrepreneurs to do their most transformative work – everywhere they work, even when it’s hard. He is the author of the international best-seller This Might Get Me Fired and an international keynote speaker. He 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 with Google, PWC, Uber, Booz Allen Hamilton, Sky, and other Fortune 500 firms to launch transformative products and empower entrepreneurs. Greg has lived all over the world but his home is Brooklyn, where he grew up.