For years, I've been connecting with interesting people and documenting insights that might help my clients and myself. What was once private is now (mostly) public.

People often ask: "How do you know all these people?" and "How do you connect these (re: random) ideas?" The answer is simple: consistent relationship cultivation and thoughtful note taking. My north star is trusting my instincts, my maps are the constellations in these reflections.

This approach to multidisciplinary networking has helped dozens of clients, colleagues, and friends strengthen their networks and unlock new opportunities. Feel free to steal these ideas directly - that's what they're for! I can't promise you'll learn FROM me, but I guarantee you can learn something WITH me. Let's go. Count it off: 1-2-3-4!

Introducing... Greg Larkin!

Do you know Greg Larkin? He’s the author of This Might Get Me Fired: A Manual for Thriving in the Corporate Entrepreneurial Underground, and numerous posts that chart the intersection of corporate culture, innovation, and the human experience. He's the founder of Punks and Pinstripes - a community built specifically for executives who've achieved success on their first mountain and are now climbing a second one.

If not, allow me to introduce you. Greg has spent decades in the trenches of major institutions - from hedge funds to Bloomberg to consulting gigs at PWC, Google, and Uber - understanding exactly how innovation survives (or dies) inside corporate walls. His work is grounded in a hard-won understanding of what it actually takes to get things done when the stakes are high and the resistance is fierce.

I wanted to connect with Greg because he embodies something I value deeply: the courage to name what's actually happening - in boardrooms, in markets, and in our own lives - and then do something about it.

Our conversation is LIVE now on the Epsilon Theory YouTube channel (and this Cultish Creative Playlist). Listen and you'll hear stories that span from New York City immigrant parents to hardcore punk shows to the "f*** you pay me" meeting that changed everything - plus his framework for understanding the five types of obstruction you'll encounter when trying to innovate inside institutions.

THREE: That's The Magic Number of Lessons

In the meantime, I wanted to pull THREE KEY LESSONS from my time with Greg Larkin to share with you (and drop into my Personal Archive).

Read on and you'll find a quote with a lesson and a reflection you can Take to work with you, Bring home with you, and Leave behind with your legacy.

WORK: Know What Your Trade Is Before You Walk Into The Room

Key Concept: Greg's brutal introduction to what he calls the "f*** you pay me meeting" - courtesy of a notoriously demanding European hedge fund manager - taught him a fundamental principle: clarity of intention matters more than polish of presentation. Whether you're pitching an investment, launching an innovation, or selling a service, there are people who will cut through the theater and demand to know exactly what value you're creating and who benefits. The sooner you can answer that question - stripped of all the slides and pleasantries - the sooner you're actually ready to do the work. Preparation isn't about having more information. It's about being able to distill your core thesis into something that passes the test of pure skepticism.

Personal Archive Note-To-Self: It’s the worst part of business. When you have to ask to get paid because up and to that point, somebody is neither paying nor offering to pay you but will gladly take your time, provided it’s useful. But for all the internal anxiety these moments produce, the realization that you have to put it on the line, that you have to risk getting punched in the face by the real world if you want anything to move forward ever, is everything.

This is the part that makes an activity business. You pitch the idea, in bare bones form, that validates the reason you’re in the room. At least, that’s how it worked in Greg’s case. In mine, and I have a million smaller stories of my own like this, it’s just choosing to ask a person like Greg to have a conversation like this, and then publish it online. And then, promote it too. That stuff is scary! But it’s the step that puts meaning on all the internal stuff that came before it.

Nobody likes sticking their neck out. We all wince a little. We just have to learn recognizing what probably isn’t going to kill us from what actually might kill us. And that takes people - like the boss Greg called after this meeting who explained what happened to him. That boss framed the interaction, and how Greg handled it. We need those re-frames from people who have been there before us.

Taking risk is part of the process. That’s how you know you’re actually in business. It gets easier, but it never gets easy.

Work question for you: What's your trade? If someone gave you 18 seconds instead of 18 slides, could you answer it?

LIFE: There's A Difference Between Pressure And Stress

Key Concept: This distinction landed hard for me. Greg is describing something most of us conflate - the weight of hard work versus the weight of meaninglessness. Pressure, by his definition, is the resistance that builds strength. It's the load you carry because you believe in what you're carrying. Stress, by contrast, is what happens when you're unsure if any of it matters. His father lived with both - the pressure of solving an important problem (mental health treatment and addiction) inside institutions he didn't fully trust. Greg learned from that observation: you can endure immense pressure if you know what you're solving for. But stress - that unnamed doubt about purpose - will hollow you out. The same difficult circumstances feel completely different depending on whether you believe in what you're doing.

Personal Archive Note-To-Self: We all have that existential dread, right? The feeling of potential and meaning, just out of grasp, that we stuff back into the cavity that is our chest, from the cavity in between our ears, by saying stuff like, "Hold fast to dreams, for if dreams die, life is a broken-winged bird that cannot fly”. We all have that conversation in our head, 47 times a day, right?

Busyness is a modern problem. All the productivity tools, all the dopamine hits we get from the, it’s never been better to busy. Which is to say, it’s never been worse to be a busy person. Because you can be very busy, and very hard working at whatever you do, and be pinned under the weight of abject and absolute meaningless, more now, than ever before in human history.

Stress is us resisting what’s in front of us. In all of the ways. And the lesson Greg shares here, with the story of his dad, and then the story of his life, is that you need stress with a name and a purpose, to not just have it spinning you out.

It’s not enough to just have all the emails and notifications and alarms going off. You have to figure out why you’re listening and noticing and caring. That evolves with us over time. Greg’s way of describing this, especially in the business punk and second mountaineers ethos, is the reminder to not let stress continue without evolving too.

Life has multiple chapters. You have to close ones out to start new ones. Then, once you’re in a new one, you need to get your bearings and make sure the new stresses are serving you, and everyone around you, for the better.

Life question for you: What in your life right now is pressure (good resistance) versus stress (doubt about direction)?

LEGACY: Innovation Dies Not Because Ideas Are Bad, But Because We Don't Know How To Handle Obstruction

Key Concept: This is the insight Greg crystallized after years inside institutions like Bloomberg - and it changes how you think about innovation, about leadership, and about what actually gets built in the world. The five obstructionists he identifies (the skeptics, the cops, the traditionalists, the territorialists, and the capitalists) aren't bugs in the system; they're features. Every single one is a legitimate concern being expressed badly. The real work isn't getting the technology right or the strategy right. The real work is understanding which obstruction you're facing and knowing exactly how to move it. Greg argues that by failing to do this work early, institutions are building up massive inventories of AI and innovation that will never actually integrate into the business - and that when companies like JP Morgan realize they can't scale what they've built, the market will feel the ripple. His point: how you navigate resistance determines whether your ideas live or die on the vine.

Personal Archive Note-To-Self: I left the big company life because I realized I could be asked to solve a problem, deliver a 100% solution, have upper management agree with 80% of it, and then ask me to put 10% of the overall plan into play over the next 3 years, with regular updates on my10% solution, aka their “new solution”, and how it was giving better than my 100% solution’s potential results, ideally, so they could tell their managers.

I tried to make the math work. I tried to make the 10% be the proof that they would see at least a good reason to increase in the direction of my approach. And I failed. Because I had a 100% solution they only asked me to do 10% of and that was never going to be enough.

Which, before I walked, I learned what else to try. How to get around obstructions, execute on points without asking for approval to get results that would demand somebody wanting to take credit (which is better than an approval, IYKYK).

But it was burning me out. And I didn’t want to be the people above me in my later career. Nor did I want to train anybody behind me to live with this system, even if I had learned how to survive, if not succeed inside of it. So I left.

Because why build a legacy you don’t want? Greg gets it. His whole community of Punks and Pinstripes have lived it too.

Legacy question for you: What innovation or idea in your world is dying not because it's bad, but because we haven't figured out how to handle the obstruction around it?

BEFORE YOU GO: Be sure to…

• Connect with Greg Larkin on LinkedIn

• Check out Punks and Pinstripes - his community for executives climbing their second mountain

• Try to read Kitschy Confidential if you dare, but probably just pick up a copy of This Might Get Me Fired: A Manual for Thriving in the Corporate Entrepreneurial Underground and follow him on LinkedIn to understand the full arc of his thinking

• Don’t forget to watch his JUST PRESS RECORD too - when I introduced him to the author/rockstar/legend Mishka Shubaly.

• Take a moment to reflect on all these ideas!

You have a Personal Network and a Personal Archive just waiting for you to build them up stronger. Look at your work, look at your life, and look at your legacy - and then, start small in each category. Today it's one person and one reflection. Tomorrow? Who knows what connections you'll create.

Don't forget to click reply/click here and tell me who you're adding to your network and why! Plus, if you already have your own Personal Archive too, let me know, I'm creating a database.

Want more? Find my Personal Archive on CultishCreative.com, watch me build a better Personal Network on the Cultish Creative YouTube channel, and listen to Just Press Record on Spotify or Apple Podcasts, and follow me on social media (LinkedIn and X) - now distributed by Epsilon Theory.

You can also check out my work as Managing Director at Sunpointe, as a host on top investment YouTube channel Excess Returns, and as Senior Editor at Perscient.