How to Innovate in Big Companies Without Risking It All?

Mudassir (00:02.307)
Please do a clap for me and then we're ready to go. Awesome. All right. Hey Greg, welcome to the show. How are you doing today?

Greg (00:09.834)
I'm great, how are you?

Mudassir (00:11.479)
I'm amazing. Thank you so much for just taking some time out for us. Like it means a lot to us.

Greg (00:17.27)
Yeah, my pleasure.

Mudassir (00:21.013)
Okay. I want to, I usually start us off like all the guests that we have from the earliest context of their life, like who they are, like what exactly has happened with them, however, you know, how do we become whoever we are today. So give us some earliest context of your life, like, you know, how did you become the Greg Larkin that we are hosting today?

Greg (00:43.726)
Uh, yeah. So I grew up in New York city and Queens, um, in the 1980s when New York was a little bit nasty. Uh, it was not the hipster capital. Um, uh, but, um, yeah. So I get really nostalgic. I still live in Brooklyn. New York is my home. I am a New Yorker through and through. Um, uh, my.

Mudassir (01:04.867)
Okay.

Greg (01:11.998)
My background is a little weird. I have, I'm definitely what, I'm an unconventional, I don't fit in any particular bucket. What I mean by that is,

Greg (01:30.002)
I accidentally stumbled into Wall Street. I began my career at an investment research startup. I had a degree in economics. I thought I was going to become a development economist about figuring out how to do business in emerging market economies and make investments in emerging markets. Just kind of by accident.

I got a job in an investment research startup called Innovest that asked me to analyze banks. And I kind of eventually became the head of product there. And then we got acquired. And

What's interesting about that is we got acquired by MSCI, a division of Morgan Stanley. So I kind of went from this, being this entrepreneur, startup guy, very young, kind of punk rock, very irreverent, and was like pulled into not just finance, but like the heart of Wall Street. And...

Mudassir (02:18.483)
Okay.

Greg (02:47.45)
and stayed there for a while. So kind of by mistake, I wound up becoming a wall, like an executive on Wall Street. And I did okay, but I was culturally a complete freak. No one, everyone there had been planning to be there their entire life. You know, there was no plan B. This was the only thing they wanted to do. This was everything they had aspired for. And for me, I'm just like, I don't...

I don't fit in. This place was not designed for me. And so I left and became, when 2015, I left my job as the head of innovation at Bloomberg and went back to entrepreneurship again. And that was also really weird because being a 40 year old entrepreneur is awkward because most entrepreneur communities are not built for people that age. They're built for people in their 20s. So like,

kind of going back to my entrepreneur roots, you know, 15 years after I was there the first time, I'm like, oh, wait, like I have kids, I have a mortgage. The problems I get excited about now are very different than the ones that excited me, you know, when I was 26. So it was sort of an awkward fit in both worlds. And I've since...

learned to accept that as a superpower, but at the time it felt like a big deficit.

Mudassir (04:20.863)
Wow, what was it exactly like working at Wall Street? What's the inside looks like? And so here's some sort of a context. So I've met two types of people. Type one is, and then again, this is not a very great classification, it's just a generic thing. Type one are the people who hate Wall Street. Like they think that's not a place for you to just go, do whatever you want to do in your life, just don't go there.

Type two of the people are like, they're doing exactly like you said, they're planning to spend their whole lives in Wall Street, right? So these are like two types of people. So what exactly is it about this industry, corporate, Wall Street, whatever you wanna call that, in finance, that people are so, they either love it, they either hate it. So what exactly is like that from the inside?

Greg (05:18.894)
What is it like on the inside? So it's like anything else in this world. If you look for the stereotype, you will find it. So on one hand, you will find some of the most alpha type A dominating everything as a zero sum game. It's always about you being the winner and someone else losing.

Mudassir (05:21.259)
Yeah.

Mudassir (05:46.153)
Mm-hmm.

Greg (05:49.023)
you will see that. If you look for it, you will see it. The stereotype of Wall Street is not something that was just conjured out of thin air. That's very real. And

Mudassir (05:50.634)
Okay.

Greg (06:03.382)
But what's interesting as well is that as markets became more automated and technology became more important in capital markets.

Mudassir (06:14.307)
Mm-hmm.

Greg (06:18.014)
A very different type of person also came into Wall Street. And even over the, like in the beginning of my time on Wall Street versus the end of my time on Wall Street, it shifted. So I'll give you a really cool example of this. When I began working at Bloomberg, there was a policy and it was official, which was, once you leave here, you're dead to us.

Mudassir (06:34.295)
Okay.

Greg (06:45.95)
Meaning they would never hire someone again if you left.

Mudassir (06:51.083)
What? Okay.

Greg (06:52.683)
Yeah.

And that was very much a product of just old Wall Street. No, you don't dump me, I dump you. It was very ego and a lot of pretty aggressive personalities that would rise into positions of leadership. By the time I quit that job in 2015, they had to very quietly reverse the policy.

Mudassir (07:15.523)
Mm-hmm.

Greg (07:25.846)
because they were running out of engineers. It used to, when I began, they could pay an engineer more. If you were a really good developer or a really good data scientist or very good at AI, they would pay you more than anyone else.

Mudassir (07:36.86)
Mm-hmm.

Mudassir (07:43.735)
Wow.

Greg (07:44.514)
By the time I left, Google's campus is literally 30 blocks away. Amazon's building a pretty big presence. Instagram was headquartered in New York at that time. LinkedIn is based, is running out of the Empire State Building. So suddenly you have a war for tech talent on your hands, a bidding war. And very quietly, they didn't make any fanfare about it, but it kind of became understood that they had to relax that policy.

Mudassir (07:51.011)
Mm-hmm.

Mudassir (07:59.499)
Mm-hmm.

Mudassir (08:03.667)
Yeah.

Greg (08:13.542)
If you left and you were a tech genius, you could probably come back. Don't tell anyone. You know, um, so it was really, the reason I say that is because one of the things that happened as technology became more important in finance and, and in capital markets, you had really weird people who never 20 years ago, 10 years ago would have never made, not only would they not have

Mudassir (08:18.291)
Okay.

Greg (08:42.786)
worked in finance, but they certainly would never have made it to a position of executive leadership. And like, I don't know, the first company that I worked for, I remember when they, when we moved into the office of the acquirers, Risk Metrics is the name of the company. And

there was a guy who looked like Gandalf from Lord of the Rings. He had like white hair, you know, he had like long white hair. He was wearing like a beat up T-shirt and he was he was sitting there with like a magnifying glass and a brush and like a set of tweezers. And he was like kind of doing something. And I asked someone, I'm like, who's that guy who looks like Gandalf and what's he doing? And the answer was

Mudassir (09:08.875)
Okay.

Greg (09:33.198)
He's doing rice calligraphy. And he's our CTO.

The CTO, the chief technology officer of Risk Metrics, one of the most successful publicly traded finance companies in the history of the Wall Street. He was this like very weird out there kind of psychedelic dude with long gray hair, dressed like jeans in a t-shirt. And when he needed to clear his head, he would paint.

Mudassir (09:40.295)
Okay.

Mudassir (09:45.271)
Ha ha

Mudassir (09:53.431)
Wow.

Yeah.

Greg (10:08.01)
Japanese characters on a grain of rice. Just to like.

Mudassir (10:13.783)
Wow. That's wild.

Greg (10:14.662)
So you had things like, you know, yes, you had these like testosterone, sweaty alpha dudes, but you also had people with a degree in physics. You also had people who literally were just. Technological puzzle solvers and who accidentally wound up working on Wall Street. And during my time there, there was this sort of.

shift in the cultural balance of power between the technologists and the meatheads, you know. And it was, I was, and I was right in the middle of it. And I hated being in the middle of that balance of power shift, but on the outside, it's kind of fascinating. And many of those people are still a really wonderful part of my life.

Mudassir (11:05.023)
How did you survive that? Because is this like a kid going to the school that he hated, students in the class that he hated, teachers that he hated, still managed to climb up the ladder very far away, very well done, but how did you survive all of that? And how much of a

emotional turmoil that was for you, like, you know, what was the mental side effect of all of that? Because, you know, you're just like going to an environment where, like, you hated being in that environment every day, but you still stayed there. So, uh...

Greg (11:38.399)
So I didn't hate it every day. I'll tell you what my best days were

Mudassir (11:41.333)
Okay.

Greg (11:47.07)
On a good day, I was able to just do my job. Just do my job. I didn't have to worry about the politics of it. And when I was able to just do my job, I got to solve things that were just fascinating. For example, can we look at a geopolitical conflict anywhere in the world and evaluate

what stocks it was likely to affect.

the minute it starts to break out, not at retroactive, like if, if the conflict between India and Pakistan were to flare up, could we be in a position to say, great, here are all the mines around there, like nickel, platinum, etc. These are all the mining companies around there.

Mudassir (12:42.211)
the gang get affected.

Greg (12:44.526)
Can we, based on all the historical precedents of things like this occurring, anticipate what the likely movement of those stocks and commodity prices is going to be based on historical movement? That's an incredibly cool puzzle to solve. If there's a piece of legislation that drops in the United States Congress just based on who sponsored the bill.

Mudassir (13:04.303)
Yeah.

Greg (13:13.922)
just based on what lobbyists were behind it. Can we identify which stocks are likely to be affected by it and whether it's going to be positive, negative or neutral? And so I got to build some incredibly cool, interesting, impactful, very creative analytical tools that made sense of...

Mudassir (13:29.731)
Okay.

Greg (13:42.658)
just unbelievable levels of complexity and just narrowed it down to this one point and click. Like, yes, buy this, sell this, stay put, don't do anything right now. And so doing that and some of the people who would emerge who were just fascinated by it and supportive of it and encouraged me to

keep going and to build my tribe and the sort of allies I met along the way and some of the technologists I met along the way, but also the counterintuitive executives. So people who have a reputation of being, I can name them, that's a very high praise for me. Like Norm Pearlstein is a guy who comes to mind. He was, I don't remember what his title was. He was one of like the top.

10 most senior people at Bloomberg. And he also at a certain point was, I think the executive editor of the Wall Street Journal. And Norm was just like pulled up a chair at my desk one day. He's like, hey, I hear you're working on something cool. I'm like, hi, Norm, I can't believe you're talking to me. And he's like eating a sandwich. And he was like,

Mudassir (15:02.519)
Yeah.

Greg (15:07.562)
walk me through it and I was able to take him through my risk products. And, and, um, you know, he was probably, I don't know, I'm going to guess he was 65 or so at the time. And it was just, it was awesome about it. It was like, it was really clear that he wished he had my job.

Mudassir (15:28.067)
Wow, okay. Yeah.

Greg (15:28.222)
you know, this very senior, very wealthy, very like famous, infamous in some regards, you know, executive. And it was just really clear that he wished he could do what I was doing. He misses that part of like, he was rediscovering his youth just by seeing me invent stuff. And so that was one way of surviving, was like, there's a...

Mudassir (15:32.907)
Yeah, very successful.

Greg (15:55.678)
There's people in that world who are incredibly humble and curious and get to a level of seniority and really they don't want it anymore. What they prefer to be doing is going back into the trenches and building stuff that makes a dent in the universe. And when you could find them and build an alliance with them, you could make incredible things come to life. It was very hard to find them. You know, they were very

it was not the norm. Most of the leaders didn't care about making a dent in the universe. Most of them were motivated by money and power and nothing else. And so at a certain point, I had to just understand things about myself compared to everyone else. Like I personally was motivated to find my tribe.

change the world and make a dent in the universe. And finally, to have money, power and recognition. And not because money, power and recognition wasn't important to me, but just because it was dependent on those other two things being satisfied. And I think once I like reconciled, like my hierarchy of needs was not Wall Street's hierarchy of needs. Some people were, but not most people. I knew I had to go, I had to quit.

Like I couldn't sustain it anymore. Once I knew that about myself, I was like, all right, well, that's not something that this place was built for. You're not the leader this place was built around. And so I left and I quit my job. And that was really hard, but it was the right thing to do. And some of the people I know from that time in my life are great, great friends.

Mudassir (17:43.339)
could imagine.

Mudassir (17:54.083)
Okay. You mentioned something, you know, we were doing some research and funny that you put it out on your LinkedIn actually. So we were hoping that maybe there's some article down there or something like that, but you actually made it very obvious and hard to miss out on. Say something around, you know, you were building something at Bloomberg and then you specifically mentioned in any other organization, that thing could have been built like 5X faster.

you know, had generated like 10 x more revenue. So, talk to me, like, why do you think so? Like, because generally, when you think about big companies, and you know, I had a couple of questions on that, because you know, you've been in that executive leadership at, you know, corporate America, you know, that's how I would like to call that. Normally you would think that they have billions of dollars, so innovation shouldn't be a problem for them.

Greg (18:23.15)
Sure.

Mudassir (18:47.467)
taking up a new initiative shouldn't be a problem for big companies, because they have that much amount of cash, they shouldn't be shying away from that. But you also mentioned that, you know, intentionally or unintentionally, things were slowed down, considerably slowed down. Why do you think so that is so?

Greg (19:06.526)
So.

Uh, let me begin first of all by not-

letting myself off the hook. And I think a lot of people who try and fail at innovation do a very bad job of acknowledging what made them a bad innovator. Um, so let me first, like, let me not buy into my own bullshit. First of all, um,

Mudassir (19:17.173)
Okay.

Mudassir (19:27.683)
Okay.

Mudassir (19:33.044)
Okay.

Greg (19:37.31)
someone who's great at innovation and someone is not necessarily the person who builds the most innovative products inside of a huge company. Um, and at that time, um,

Greg (19:54.378)
Let me back that up a second more. Every company in the world, there is constant tension between preservationists on one hand, people who want things to stay the same and disruptors who want things to change constant. They're going back and forth with one another all the time. And ostensibly it's because one thinks the other, like sometimes it's rational. It's that argument is about.

Mudassir (19:56.596)
Mm-hmm.

Greg (20:24.502)
the right risk and reward. Very often, and the thing that people don't like to talk about is that it's also about ego. Who's supposed to be in charge here?

Um, if you innovate, does that mean that I'm not worthy of the power that I've accumulated? Are you challenging me? You know, self preservation and self promotion are powerful instincts in any organization and no one should ever underestimate how obstructionist someone might become when they feel like their ability to

their ability to be a self preservationist or a self promoter is blocked or threatened.

Greg (21:14.434)
I very naively hoped at the time that everyone was as excited about innovating as I was. You know, I just did. I just assumed that everyone was in it to win it, that their intentions were pure. That was never true. Some people were. But that's not the gravitational, you know, norm of the organization.

Mudassir (21:26.294)
Okay.

Mudassir (21:30.157)
Yeah.

Greg (21:43.85)
And really what I came to appreciate was that the best innovators and people who are the best transformationists inside of a larger organization has nothing to do with strategy and execution or their ability to put billions of dollars to work. It's can you recognize the obstructionist defense and can you call the right play to get past it?

That's it. The product launch, the product turnaround, the business turnaround is the thing that happens after that. And if it gets talked about in Fast Company or in the Wall Street Journal, no one's like, they tend to play the ribbon cutting ceremony. They don't go back to the part where there was a huge civil war and innovation won.

Greg (22:38.302)
And I was part of that civil war and I didn't win, you know, and I was, I was not a good soldier in it. Um, and so I don't want to let myself off the hook. I was a flawed person to be trying to win the fight that I was in. I didn't even know I was in the fight. Um, I'm a little older and I've been through some shit and I see it now more clearly than I did before, like there are five obstructionists.

And if you're going to go and try to build something new or change something old inside of a large company, you need to know who they are. You're going to encounter them. There's the skeptics, the cops, the traditionalist, the territorialist and the capitalist five. And there you're going to be hit maybe by all of them all at once, but you're going to be, you're always going to encounter them. And you always need to understand how

Mudassir (23:09.452)
Mm-hmm.

Mudassir (23:22.631)
Okay.

Greg (23:34.422)
You're going to how to anticipate them and what's the right play to call when you encounter them. And I know that now. I did not have that toolkit at the time. I only wound up developing it after Bloomberg when I had some time to think and be like, man, I built some stuff there that would have made a lot of people a lot of money and they killed it. Why? And now I know why.

Mudassir (23:46.185)
Mm-hmm.

Mudassir (23:57.491)
Yeah. Why?

Greg (24:04.802)
Cause I didn't know how to be an anti-obstructionist. I didn't, yeah, I do know. Absolutely, I do know. I, no, I got my ass kicked enough to figure it out.

Mudassir (24:08.439)
But you do now.

Okay, but not at that time, right?

Mudassir (24:20.183)
Okay. Okay, what are you doing today and why are you doing today? Whatever you're doing today.

Greg (24:28.438)
Um, so I, uh, today I run a company called punks and pinstripes. It is a vetted community of, uh, corporate executive punks and people who left corporate leadership to launch new ventures. And, um, there's only 200 members. We only allow 25 new members to join every quarter. And, um,

Mudassir (24:46.836)
Okay.

Greg (24:58.154)
Why am I doing it? When I was a corporate executive in finance, and even after I left finance and was doing work with Google and PWC.

Greg (25:15.83)
the community that was sort of readily available was not, was the right demographic, but never the right psychographic. What do I mean by that? I would get sent to things like the Deloitte, you know, digital innovation summit, or something like that, where it was a bunch of other like innovation executives or CIOs or what have you across the Fortune 1000. And,

It was very much focused on tactics, but what they were not talking about is like, Hey, we're in this together. You're not alone. Everyone who's trying to move a big mountain and a big company goes through what you're going through. Let me help you out. Let me help you get unstuck.

Mudassir (25:59.104)
Mm-hmm.

Greg (26:05.85)
And I needed that. I needed to find my tribe. I needed to know other people who were like battling obstructionism just like me. And when I left and became an entrepreneur again, I wasn't gonna like register for Y Combinator. I wasn't 24.

Mudassir (26:15.403)
Yeah.

Mm-hmm.

Greg (26:30.698)
You know, I was like, I had kids and a mortgage and a 401k and like the problems that I was aware of and excited about were

Greg (26:42.23)
I didn't care about the hype cycle anymore. You know, I was like, I just saw just $100 billion broken systems inside of Wall Street that no one on the inside can fix.

Mudassir (26:47.964)
Yeah, bigger problems.

Greg (27:00.802)
Why am I going to waste my time on the blockchain? I get it. It's popular, but it's, it's screaming for yet someone else to like dive in. No, like that's not. And so I just, um, I think there's this huge disparity between

Mudassir (27:05.736)
Exactly.

Greg (27:22.894)
who a successful founder is and what the image of a successful founder is. The most successful entrepreneurs on average are 46 years old. If you look at the largest fundraising rounds of 2023, the average age is 53 years old. If you take Sam Altman, who's 39, out of that mix, the average age jumps to 55.

Mudassir (27:31.063)
Please.

Mudassir (27:51.629)
Wow.

Greg (27:52.082)
And we have been fed this image of this 27 year old, 30 under 30. You know, it's not real. I mean, it's real, but it's not real. Like the, the most successful founders do exactly what I did. They spend 20 years working their ass off inside of a huge company. They see a problem that they can solve better, faster, smarter than the incumbents and they leave to do so.

Um, those are the most successful founders and there's no community for them. There's no community specifically geared for like, Hey, we're going to help you get unstuck. We're going to tell you what it means to be a, what fundraising options are available to you, what is your sales process look like and how do you talk about this to your spouse?

You know, how do you convince your parents that you're not insane for leaving a stable job on Wall Street?

Mudassir (28:52.779)
That's the most important problem that we have. I swear to God.

Mudassir (29:01.539)
I swear. Yeah.

Greg (29:03.87)
You know, how do you, how do you have that high trust, intimate vulnerability that you just need in order to like, be okay and not let the weight and the pressure of it kill you. Um, you know, and I found, I found that community's more easy to find when you're, when you're like 28, um, I'm 46 most founders are.

Mudassir (29:29.195)
Hmm.

Greg (29:33.65)
Most successful founders are, but you know, the like media demographic, that's the most desirable is 18 to 25. The founder demographic that's the most successful is 46 and older. And so we've been fed the media demographic as being this most successful entrepreneur. It's not true. And one of the negative consequences of that myth is the most successful founders can't find one another.

Mudassir (29:41.736)
Yeah.

Mudassir (29:46.304)
Mm-hmm.

Mudassir (29:52.808)
Yep.

Greg (30:04.046)
can't help each other out, can't be a support network for each other. So punks and pen stripes solves that.

Mudassir (30:10.723)
How many people do you have on the community now?

Greg (30:13.654)
We have 34 and we're very, so there's never gonna be more than 200 members and we only allow 25 new members to join per quarter.

Mudassir (30:25.315)
Yeah, like what you're gonna do? You're just gonna kick them out? Like once you have like more applicants or something like that.

Greg (30:31.41)
No, there'll be a wait list. So once we have more applicants, yeah, no, no one gets kicked out. If you're here, I hope you stay here. When someone applies and we accept them, and you have to get vetted by three members who want you to, who then give you a thumbs up to become a member. And if there's attrition or a spot opens up, we'll let the people on the wait list in. You have to pay money to be on the wait list.

Mudassir (30:37.411)
Okay.

Mudassir (30:41.475)
Okay.

Mudassir (30:58.06)
Mm-hmm.

Greg (31:01.662)
Of course. Um, yeah.

Mudassir (31:01.819)
Yeah, yeah, why not, yeah. Okay. Okay, that's very interesting. I wanna ask you like one more question and then we'll take onto the like some of our segment that we just had. The question that was coming to my mind was around greater resignation. And I think you wrote an article that great resignation is becoming more of an entrepreneur exodus in many ways. Like question one.

that comes to my mind is like, why is that happening? Like why is that great recognition thing is happening? Question two is, what do you think big course needs to do in order to retain that talent?

Greg (31:44.286)
Yeah, those are great questions. So.

Greg (31:50.41)
One of the headlines is that the level of great resignation ended in 2023 as tech started to lay people off. That's not exactly true. It's not exactly true. So in other words, the number of people who are quitting their jobs has slowed down.

Mudassir (32:04.767)
Yeah.

Mudassir (32:16.116)
Mm-hmm.

Greg (32:18.462)
has fallen back to its normal levels. That part is true. But when they left their jobs, they didn't go and then find a new job at another large corporation. So what we have is that since 2020, we had a doubling of the number, I'm talking about the United States, I should clarify that. There were twice as many people,

Mudassir (32:41.931)
Mm-hmm.

Greg (32:46.33)
launch startups in 2020, that number has never stopped.

So it has, like you would think that would go back down as the great resignation stopped, it has not. So, and when we start to look at companies like Goldman Sachs, like Google, the people who are leaving those companies are not leaving, are becoming founders, in many cases, first time founders. And it's this fascinating, totally under the radar,

Mudassir (32:56.744)
Mm-hmm.

Mudassir (33:06.796)
Mm-hmm.

Greg (33:22.506)
megatrend of this like innovation talent diaspora. And so that's, is it the great resignation? No, it's not that anymore, but is there, like we did a really great analysis at Punks and Pen Stripes of who on Wall Street is winning the war for AI talent. And what we found is that for every,

Mudassir (33:47.491)
Mm-hmm. I read that. Yeah, I read that.

Greg (33:51.102)
So for every one AI person that the biggest Wall Street banks has hired, they have lost one.

Um, so at the current rate of attrition for AI talent in finance, Goldman Sachs will have zero AI people on staff by 2025 if it continues to lose as many AI people as it currently is. Can they correct that? Sure. Can they acquire some AI talent? Sure. But at its current rate, they will run out of AI people.

by 2025. So when these people are leaving, where do they go? Are they going from Goldman Sachs to Morgan Stanley? No. They're leaving finance altogether.

Mudassir (34:43.603)
Yeah.

Greg (34:45.714)
Um, that's one of the most, so the idea that like the great resignation is over only makes sense if you stop rolling, if you stop the camera, as soon as someone quits their job, you should not stop the camera, then you have to keep following them and ask them after you resigned, what did you do next with your life?

Mudassir (34:58.623)
Yeah.

Mudassir (35:10.415)
Starting a startup. Right.

Greg (35:12.074)
Yes. Starting a startup when VC numbers are contracting...

Mudassir (35:18.786)
Exactly, exactly like that in this particular market.

Greg (35:20.466)
in an environment that's not amenable to launching a startup, still doing it anyway. And that headline, I think that data is misunderstood. I'm trying to elevate it. Certainly that's the biggest driver of that entrepreneur exodus is the biggest driver of membership to punks and pinstripes. And I was part of that entrepreneur exodus. I get it.

Mudassir (35:25.147)
Yeah, absolutely. Yeah.

Greg (35:50.746)
I was that guy. I know how hard it is. So I feel like that's one of the most misunderstood megatrends of our time. It's also a very interesting point about that is open AI is the entrepreneur exodus. So there's 130 senior executives at open AI, all of them. So 58 of them.

Mudassir (36:11.829)
I read that too.

Mudassir (36:17.003)
Mm-hmm.

Greg (36:19.902)
including the founder, Sam Altman, are ex-Google. Then from there, the remainder are Amazon, Apple, Microsoft. So this image of the guy dropping out of Stanford or Harvard or MIT and being a startup founder, not anymore. That's an old...

That was true for Mark Zuckerberg. That's not who the best, most dangerous founders of our time are. They're people who did everything they could to go as fast as they could inside a corporate leadership and then they left. And open AI is the most famous example of that. That's not something which was thought through in Stanford by some student. It was something that someone tried to hatch inside of Google.

Mudassir (37:10.219)
Yeah.

Mudassir (37:17.515)
Yep, okay. All right, thank you for that, Greg, really appreciate that. So we have, so the most of the, so I'll give you some context, like why the hell, like we're doing this podcast. So when I started a company, I had like no idea what exactly is a company. So like now I understand that. So I had a project and I thought, oh, okay, so this is a business. I was wrong in many ways. I did not know.

Greg (37:31.054)
Sure.

Mudassir (37:46.663)
like how to build a team, how to, you know, just getting incorporated doesn't mean that you build a company, you build a business, doesn't mean that. Most people still make the same mistakes. Most people, like mostly people are like first time founders. Still the media portrayed first time founders, which is like what, like 18 to 25? That's, you know, range when people start the business? So they come across like all sorts of problems. Don't know who to hire, don't know how to hire, don't know how to raise funds, when to raise, like all sorts of problems. So that is when.

Greg (38:06.818)
Mm-hmm.

Mudassir (38:15.991)
we started this thing, okay, so we will talk to all these successful people, people who have done something in their life, you know, so they have spent like 20 plus years, each one of them, and we learn from them and try to, you know, educate everybody as much as we can so people at least not make us, so if, you know, one single person is, you know, I don't know, from this podcast, like one single person is successful, the goal is done. So that is that. So one of the sections that we do is we don't know.

a poll through our community, so we have a decent bit of a community, and we ask them, like, okay, so this is the person that we are inviting on the podcast. Any particular question comes to your mind, please shoot away. So there's, like, a lot of those questions, dozens of those, but we just pick five of them. So in no particular order, so I'm just, you know, we'll share them with you. So question one is, why working at a corporate now is sort of looked down upon? Like why people don't like working in corporate now?

Greg (38:54.123)
Mm-hmm.

Greg (39:13.846)
I mean, I think they're making a mistake. I think you should work in a corporate. I think the best founders come from corporate. It's very difficult, but...

Mudassir (39:16.639)
of not working to corporate. Okay.

Mudassir (39:24.355)
Okay.

Mudassir (39:29.459)
Yeah, it's not cool.

media cool because you know if you're like you know 22 you raised a million bucks with some you know hot shot idea you know you so yeah that that's cool you know because now you have more following and stuff like that who cares about success but it's cool

Greg (39:48.484)
I don't know, you think Jeff Bezos is cool?

Mudassir (39:52.103)
I don't think a lot of people would... So if you take out like what he has built, for example, if you just take out the Amazon, if you take out the success...

Greg (39:57.77)
How can you take out what he's built? He built the biggest company in the world from scratch.

Mudassir (40:00.856)
No, I mean...

Mudassir (40:04.64)
The reason why I would say that is, someone would argue, so if you take it all that out, he doesn't fit that cool person persona, right? But he has, yeah, that's my point.

Greg (40:13.262)
Sure.

Okay, sure. Jeff Bezos worked at D.E. Shaw before he became the founder of Amazon. D.E. Shaw is one of the oldest, most established hedge funds in New York, or I don't know if it's in New York, but in the world. It's boring. It's a corporation. It's a Wall Street fund. That's D.E. Shaw. That's Jeff Bezos, one of the most successful founders on earth.

Mudassir (40:31.789)
Mm-hmm.

Mudassir (40:38.786)
Yeah.

Greg (40:45.33)
Sam Altman, OpenAI, worked at Google. So I think if what you're defining is cool, you mean the image you're being fed on TikTok of how someone, you know, of like some guy on a yacht in St. Barts, you know, that's not real.

Mudassir (40:45.468)
Mm-hmm. Same thing.

Mudassir (41:03.159)
The media fed cool. Yeah, exactly, exactly like that.

Mudassir (41:11.351)
Yep.

Yeah.

Greg (41:14.814)
And a lot of those people have committed horrible fraud, like Sam Altman. Not Sam Altman, Sam Blankfein. Jesus, Sam Blankfein. No, that's not what I mean. FTX, thank you.

Mudassir (41:18.071)
Mm-hmm. Oh, come on. Yeah, yeah.

Mudassir (41:29.072)
FDX guy, yeah, yeah. Yeah.

Greg (41:34.946)
So.

Greg (41:39.05)
Um, I, I do think there's a lot to be taken out of a corporation. If you're willing to put the investment into it. If you're an innovator, if you're inherently wired to like build new stuff, you're going to be disappointed. That's okay. You're going to learn, like if you're just comfortable that it's not a permanent home, but you're going to learn a lot about how to be a more effective entrepreneur.

Mudassir (41:46.585)
Mm-hmm.

Mm-hmm.

Mudassir (41:54.567)
Mm-hmm. Okay.

Greg (42:08.846)
from the time that you are in a big company. It will be the most valuable founder school you could ever go to. And you're gonna get your ass kicked and it's gonna be very painful and you're not necessarily gonna like coming to work every day.

Mudassir (42:16.904)
Okay.

Greg (42:28.122)
spending 10 years failing at a bunch of social media startups is pretty painful too. And so I think if you subscribe to the mythology of cool, A, I don't think that's cool, but B, you know, I think working in a big company and understanding what its limitations are is the best entrepreneur education you could get.

Mudassir (42:33.735)
Exactly.

Mudassir (42:37.737)
Yeah.

Mudassir (42:53.823)
Okay, great. Second one, would you ever consider starting another startup now that you're older?

Greg (43:02.222)
sure. I mean, I am punks and pinstripes is a startup. Is it a venture backed startup? Is it the same as Innovest when I was 27? No. But the startup I'm building right now is 100% the right startup. Yeah, no, I'm doing it. So the answer to that is 100%. Yes. But it's not it's not. It's not a

Mudassir (43:05.992)
Yeah.

Mudassir (43:11.907)
Mm-hmm.

No. Okay.

Greg (43:30.55)
the startup I would have started when I was 24.

Mudassir (43:33.967)
Yeah, that makes sense. Third, that we have is usually startups come with innovation with less resources. So I think we already discussed that one. So the fourth is, how did you come up with the title? This might get me fired. So this is, I think, referring to your book. So did you actually get fired? Did you think about getting? So what's the story behind that? That's a good one. You should have asked that at the beginning, yeah.

Greg (43:57.39)
Sure.

Greg (44:00.734)
Um, what I realized after 10 years working in finance, after my startup got acquired, actually it wasn't quite 10 years, um, probably in year six was, um, every time I started to actually build something that made money, that gained traction, that started to do all the things that we in startups, you would call product market fit.

Mudassir (44:27.954)
Mm-hmm.

Greg (44:29.622)
Every time that started to really kick in and take effect, I also almost always got fired. It started this massive civil war, and this awful political, like, how dare you?

Greg (44:49.126)
And after a while I'm like, you know, I've come to sort of, and I looked around me and at a certain point I'm like, this is crazy. But like, if I look around at every innovative incubated new product that has come out of this company and every company, the person who built it almost always got fired first. They risked their career to build something they cared about.

Mudassir (45:08.991)
Mm-hmm.

Greg (45:18.811)
and

Mudassir (45:18.985)
Yeah.

Greg (45:23.246)
That's how innovation happens. It always starts in that moment. The thing that is Google DeepMind, Amazon Web Services. It's not something that like, wow, these guys are geniuses. They must've been working on this and top secret. No, the person who started it nearly got killed trying to build it. You have to understand that every time.

Mudassir (45:35.731)
Yeah.

Mudassir (45:50.615)
Yep.

Greg (45:53.014)
And that's often, and I'm like, all right, if you're gonna write a book about innovation and it's written not by some outside observer from Harvard Business School who thinks they've done the research, but actually someone who's lived through it in the trenches, the best, most appropriate title of how to innovate inside of a large company is this might get me fired because it almost always will. And if it hasn't, you haven't innovated a goddamn thing.

Mudassir (46:23.038)
Okay, love it. Okay, so the next one is, so I think the previous part of that question is like assuming that you're into punk rock music because I think that's pretty obvious. Give us your five top punk rock tracks of all time.

Greg (46:38.754)
tracks or bands?

Mudassir (46:40.291)
tracks, bands, I think you could do the bands thing. We can change that, no problem.

Greg (46:47.886)
Okay, that's a good one. All right. At the Atlantis by Bad Brains. Number one. Number two. Lust for Life, Iggy Pop.

Mudassir (46:57.783)
Okay.

Mudassir (47:03.815)
Love it.

Greg (47:05.151)
Number three.

Greg (47:11.55)
The Passenger also Iggy Pop.

Mudassir (47:14.291)
Iggy Pop, okay.

Greg (47:16.346)
Number four, 53rd and third by the Ramones.

Greg (47:25.842)
Number five, oof, man.

Greg (47:36.257)
Okay.

I'm not sure how high conviction this is, but I'm going to just put it out there. The weight by the pretenders off of their first album. Those are my top five.

Mudassir (47:50.467)
Okay, amazing. Okay, thank you for that. So what I do is like part of the reason why I have all these conversations is because I consider myself a student, like a lifelong learner. So I ask like one single question for my personal learning. That's like very selfish thing to ask, but I do that. So one question that I wanna ask you is, what's the most important business or leadership lesson that you have learned?

Greg (48:05.198)
Sure.

Mudassir (48:17.279)
You fish you had known earlier in your entrepreneurial journey. If it has to come down to just one that you think, God, I wish I knew that 20 years ago. What would that be?

Greg (48:41.376)
There's so many. I'm such a better founder now than I was. Can I give you three?

Mudassir (48:49.971)
Mm-hmm. Even better, okay.

Greg (48:54.255)
Um

Greg (48:57.71)
So your success depends on what you say no to.

Greg (49:04.65)
You're going to be given advice and ideas and playbooks, rule books by everybody. You're gonna be bombarded by, and you, if you're an entrepreneur, tend to be, will probably be someone who's constantly thinking of stuff. Your ability to...

Mudassir (49:15.592)
Mm-hmm.

Mudassir (49:30.22)
Mm-hmm.

Greg (49:36.302)
say no to everything, even things you really, really want to do, and just focus on the two most important things.

Mudassir (49:43.571)
Mm-hmm.

Greg (49:52.699)
That's what's going to make you succeed. You will be judged by what you say no to. That's, and there's a, and the discipline of doing that and the discipline of disappointing others and the discipline of seeing what's happening out there and being

Mudassir (49:55.325)
Okay.

Mudassir (49:59.116)
Got it.

Greg (50:14.342)
not being seduced by it is extremely hard.

Greg (50:22.917)
Number two.

Greg (50:28.398)
Find a way to feel good about yourself and your life, even if the outcomes that you're pursuing are not met.

Mudassir (50:40.361)
self explanatory in many ways.

Greg (50:43.378)
If you can't finish the day without having landed your big sale, without having landed your big investor, without having built your big breakthrough, something that is giving you existential fear because you know you have to do it. And it's keeping you up at night that you haven't been able to do it. If you can't finish that day where you didn't get to where you want to go and find a way to be grateful for what you have, proud of what you did.

You know, the best you can do sometimes as an entrepreneur is just open the miracle window as far as you can. The miracle, you don't control when the miracle comes in. That's out of your control.

Mudassir (51:16.471)
Mm-hmm.

Greg (51:29.494)
But can you open the miracle window as far as you can? Can you finish every day?

every day being like, I opened it as far as I can.

Um, and if you can't do that, you won't be able to survive it. It's too much pressure. It's too much stress. Um, there's no such thing as not worrying about money. Never happens. Um, people who say that's happened to them are lying to you. It doesn't exist. And you, you have to be able to.

Mudassir (52:06.258)
Mm-hmm.

Greg (52:11.426)
feel a sense of fulfillment and pride and joy in your life, in the absence of all the things you want happening, happening. You won't, you can't survive this life if you can't figure that out. And there's another dangerous thing that happens, which is the anticlimactic victory. The people who don't invest in their happiness outside of their business, get the things they want and are still miserable. Very miserable.

Mudassir (52:29.795)
Okay.

Mudassir (52:38.978)
Yep.

Greg (52:40.382)
I've had that happen too.

Greg (52:46.91)
Yeah, that's lesson number two. Lesson number three. Don't do this alone.

Um, if you can't find your tribe and build a community and invest in your community, um, you can't get through it. You won't be able to get unstuck. You won't be able to get to where you want to go. Um, one of the things that I have realized over time is that there is a gigantic difference between the advice you get from, uh, a survivor and the advice that you get from a pundit.

Someone who's been through what you're going through and come to the other side will offer you advice only because they want you to be okay. That's it. They want you to, they have no ulterior motive except they want you to be okay and to do well because they want you to win period end of discussion. It's the only thing underpinning that. And.

Mudassir (53:29.132)
Yep.

Mudassir (53:35.562)
Yeah. And not telling anything except.

Mm-hmm.

Greg (53:56.854)
There are so many coaches and false profits and people who are trying to separate you from their money and turning themselves into these demagogues, putting images out on social media, which is like, wanna know how perfect I've become? Guess what? You can be perfect too. And they sell it very well. Most of them haven't been through it. Most of them haven't had to survive what you're going through.

And if you cannot, you have to surround yourself with the community of survivors where there is just zero ulterior motive. That's literally the return on investment from punks and pinstripes. That's the reason this community works. It's people who otherwise would be forced having to go to executive coaches, pundits, thought leaders, none of whom have had to go through the thing that they're doing.

None of whom have built the thing that they're building. And instead they get to turn to one another, people who are in it, who can feel their pain, who can talk to them and be like, man, I've been where you are. And trust me, it gets better. There were three things that worked for me. Here's what they were. I hope it works for you.

Mudassir (54:53.352)
Mm-hmm.

Mudassir (55:13.343)
Absolutely.

Greg (55:13.346)
And the advice that, and here's the playbook of things that you just, everyone's gonna tell you to do this. They're all full of shit. Anyone who says this to you is lying. And man, if that's the, if you have someone like that and you can send a text message to them at three in the morning when you're staring at the ceiling, you're gonna be okay. You're gonna be a really successful founder.

you're gonna have a more fulfilling life. You know, and that's, I think, the most thrilling part of, like, I get paid to do that. I get paid to create that for people. It's kind of a, it's an immense privilege for me.

Mudassir (55:43.319)
Mm-hmm.

Mudassir (55:55.451)
It took you so long to build that. So it's just not like you build it overnight or something. You've been through that for 20 years, 25 years. You find the tribe. Now you're building it. So it's just not like, oh yeah, okay, let's just create a community out of thin air. By the time I'm 21, no, it doesn't happen like that, right?

Greg (56:12.714)
I think I undervalued how important it was when I was 21. You know, I think at a certain point I got to, in fact, it was a very vivid point. Like after I left Bloomberg, I, you know, I took a day and I sat down with a giant piece of paper and I put like all the things that I really was successful at on one side of the page and all the things that were failures on the other side of the page. And then I just, I remember specifically like,

Mudassir (56:16.531)
Maybe.

Greg (56:41.71)
Who was I working with? How much money did I have? What was the technology I used? And what was fascinating about that was that the things that were really successful, the one common denominator was people. Who my mentors were, who my team was, who my bosses were.

Mudassir (56:59.128)
Mm-hmm.

Greg (57:03.646)
Everything else was equal. I had the same technology and the successes and the failures. I had AI in the success column and the failure column. There were successes that used very little money and failures that had used hundreds of millions of dollars. The only common denominator was people and community. You have to succeed and fail a whole lot to know that.

Mudassir (57:05.805)
Yep.

Mudassir (57:33.109)
Yeah.

Greg (57:33.27)
You know, it took me a long time to just realize like, wow, I never took the time to do this exercise, but now that I'd done it, there's a really clear pattern. I'm glad I know that now. I hope some of your listeners can. Hear, learn, learn from, from me realizing that at the age of 40 and figure it out a lot earlier for themselves.

Mudassir (57:43.328)
Yeah.

Mudassir (57:50.271)
No, absolutely. I think it's super helpful.

Mudassir (57:59.883)
Hopefully. Okay, Greg, so we have this tradition on the podcast. So what we do is we ask all our guests a question for our next guest without telling them who the next guest is gonna be without knowing who the next guest is gonna be. So we have a question for you that the previous guest left and then we obviously gonna take a question for our next guest. So yeah. So the question that he left for you is.

Greg (58:11.831)
Alright.

Greg (58:18.318)
Great.

Mudassir (58:23.511)
So first time founders are usually burned out, like most of them, because of this extreme hustle culture, like they need to be working 18 hours a day, or the weekend, all of that crap. How can they maintain a work-life balance?

Greg (58:41.902)
How can they maintain a work life? So it's really hard, but it's a lot easier when you have kids. Because that's a shitty piece of advice. I have two kids and I had my son who's now about to turn 16. I had him when I was 30. So that would be...

Mudassir (58:50.051)
Thanks for watching!

Yeah. Ha ha ha.

Mudassir (59:03.815)
Oh, okay.

Greg (59:09.582)
Two years before Innovest was sold, my first ever startup.

Mudassir (59:14.476)
Okay.

Greg (59:15.625)
Um

Greg (59:19.73)
I couldn't work late after he was born. You know, like, I had to, and by the way, when he was born, I wasn't just working at a startup. I was responsible for analyzing banks in the middle of the 2008 financial crisis. And I was the person that predicted Lehman Brothers was going to collapse. So.

Mudassir (59:22.811)
I swear.

Mudassir (59:43.067)
Yeah, I had that question, but we were just like running out of time. So I was like, okay, maybe some other day I had that written out. Like, how did you predict that?

Greg (59:55.423)
Uh, I, so I've always been obsessed with weird data. I continue to be obsessed with weird data. And one of the data points that I looked at was where all the people who were suddenly able to afford mortgages, were their savings going up? Like where their incomes going up? Like, how is this happening? Is this.

sustainable, like what's going to happen if they don't, if they can't afford it. And what I found was a very simple chart. And if you go back, I'll send it to you. It's kind of cool. But that between 2000 and 2006, when I wrote that first report, a very interesting uncoupling had happened, which is that historically prior to 2000.

Mudassir (01:00:23.745)
Yeah.

Greg (01:00:46.698)
Real wages and household savings rates in the United States used to kind of go up and down in conjunction with each other. From 2000 to 2006, real wages declined by 2%. And household credit rates, the amount of that households were borrowing had gone up 72%.

Mudassir (01:00:55.365)
Mm-hmm.

Mudassir (01:01:07.85)
Yeah.

Mudassir (01:01:14.548)
Wow.

Greg (01:01:16.222)
So the question for me at that point was, who's issuing the most mortgages to these households? Is there any data that can enable us to get a sense, a glimmer of understanding of who's the most exposed? And the answer was Bear Stearns, Lehman Brothers and Countrywide Financial. That's it. That's literally as simple as it was. There was a lot, what doesn't...

Mudassir (01:01:31.137)
Mm-hmm.

Greg (01:01:43.362)
What you don't see inside of that very clean answer was just how different that was than how banks are normally analyzed. It was a total deviation from normal. You also don't see just how many mistakes we made.

Mudassir (01:01:57.125)
Mm-hmm.

Greg (01:02:06.978)
how much bad data we had, how much unreliable data we had, how much data was just impossible to extract. No one sees that. So it was a very hard piece of analysis to come up with, but it just gets presented in this like tiny, single, cute, very clear, very simply written.

Mudassir (01:02:09.26)
Mm-hmm.

Mudassir (01:02:27.701)
Yeah.

Greg (01:02:35.475)
a 12 year old could have read that and understood why we were making the prediction we made.

the amount of work, hours, weekends, very bad work-life balance that went into getting to something that small and clean about something so big, not for the faint of heart, very hard. So I have to say one other thing. The person who was my research assistant when I was doing that was a woman who was an intern. She started as an intern.

Mudassir (01:02:47.035)
Oh, unbelievable. Yeah.

Mudassir (01:02:58.679)
Mm-hmm.

Go ahead please.

Greg (01:03:12.994)
Her name was Laura Nishikawa, and she's now the head of ESG at MSCI. And I just, I wanna like give a shout out because I think that's another huge, every chance I could get to put Laura on stage instead of me, I did. You know, every time CNBC wanted to interview me, I'm like, you know, why don't you speak to Laura?

Not because I didn't feel comfortable in front of the camera, but it was so important for me that she got recognition.

Greg (01:03:48.658)
I cannot overstate how important it is for founders to share the wins and share the success with the people who give them their loyalty, who subscribe to the vision. If you can't, turn them into rock stars and do everything you can to make the world aware of it.

Mudassir (01:04:05.616)
Mm-hmm.

Greg (01:04:17.93)
A, you're gonna have a lot of entrepreneur exodus on your hands and B, that was almost, that was 16 years ago. Watching her become one of the most successful women in finance is like one of the great joys of my life now. Just standing on the sidelines and seeing like, man, I was there at the very beginning. It's like, if you cannot experience that joy, you're.

depriving yourself of one of the great benefits of a strong entrepreneur karma bank account.

Mudassir (01:04:49.098)
Mm-hmm.

Mudassir (01:04:56.42)
Okay. Yeah, question for our next guest.

Greg (01:05:08.438)
What is the most anticlimactic victory you've ever experienced?

Mudassir (01:05:14.139)
Okay. Tough one. But okay. I appreciate it. Thank you so much, Greg. Go ahead, please.

Greg (01:05:22.222)
Do you want a different one? I give you another one. You want another one?

Greg (01:05:28.568)
Yeah.

Mudassir (01:05:28.767)
No, that was a good one. I loved it. But give me another one. Like, regardless of any of that.

Greg (01:05:34.478)
So actually, I have it, I always keep it close by because I've always hated small talk and um

Mudassir (01:05:39.721)
Okay?

Oh my, okay.

Greg (01:05:43.886)
So I always have a list of 26 questions to avoid small talk. I've been building up on this list throughout my career.

Mudassir (01:05:47.523)
Thanks for watching!

Mudassir (01:05:51.395)
Unbelievable.

Greg (01:05:53.434)
Oh, I love this is the best one.

Mudassir (01:05:55.459)
Okay.

Greg (01:05:58.414)
Who is the most courageous person you've ever worked with?

Mudassir (01:06:03.633)
Okay, that's a good one. That's a good one. Okay.

Greg (01:06:05.506)
Do that one. I feel like that's a little more upbeat.

Mudassir (01:06:08.807)
Yeah. OK, I'll ask them the first one as a random interview question. I'm going to take this one at the end. OK? All right, guys, thank you so much. Please just wait a few minutes so this thing can close down and the recording is loaded. OK? Thank you so much.

Greg (01:06:16.808)
Awesome.

Greg (01:06:24.286)
Okay. And does that mean I don't leave the room in the bottom right?

Mudassir (01:06:30.323)
Yeah, just give me a minute. Let's just say bye so we can stop the recording. And then after a minute, we can end the call. So thanks, Greg. Appreciate it. Love talking to you. So many different takes, so many insights. So appreciate the time. Thank you so much.

Greg (01:06:37.462)
Perfect. Okay.

Greg (01:06:45.57)
Thanks for watching, take care.

Mudassir (01:06:50.682)
I should be good anyway, no.

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