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... Mat Cashman!
Do you know Mat Cashman? He's the Principal of Investor Education at the Options Clearing Corporation - the person tasked with teaching retail traders and professionals alike how to think about options in ways that don't kill them or their portfolios.
If not, allow me to introduce you. Mat is a former floor trader, desk builder, and market maker who spent years in the pits - from the Cboe in Chicago to the Eurex in London. He's a classical saxophonist trained at Northwestern. He's survived sarcoidosis, blown-up trading firms, and the peculiar humbling that comes from walking away from a career you've built to become the person who teaches others not to repeat your mistakes.
I wanted to connect with him because he embodies something I value deeply: the willingness to weaponize your scars into education for the next person.
Our conversation is LIVE now on the Epsilon Theory YouTube channel (and this Cultish Creative Playlist). Listen and you'll hear stories about napkins and broken forks, Coltrane practicing in bathroom stalls, why perfectionism and productivity are the same trap, and the moment he knew a ten-year project had just evaporated on a Friday morning in December.
THREE: That's The Magic Number of Lessons
In the meantime, I wanted to pull THREE KEY LESSONS from my time with Mat 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: The Best Education Happens Over Lunch
"The six months where I was Lanny's clerk, he taught me how options worked. It really included me meeting him at lunch in the Cboe members lounge with a chicken Caesar salad and a stack of napkins and extra forks, 'cause he always broke his fork, 'cause Lanny was pretty wound up. The napkins were so that he could write option strategies and put call parity and P&L graphs and everything on the napkins, and then like slide them across the table to me. That's where my theoretical education came from - trial by fire. He'd ask me questions about things, and when I got the wrong answer, it was just like, 'No, no.' You're just like, 'Oh, God, please.'"
Key Concept: Mentorship doesn't happen in classrooms or structured curriculum. It happens in moments - over lunch, with napkins, where a master is so invested in your understanding that he brings extra forks knowing he'll snap them. The best education prepares you for reality by refusing to sanitize the learning experience. You learn options theory through the mess of actual practice, through questions designed to expose gaps in your thinking, through the discomfort of being wrong in front of someone who knows better. This is trial by fire - and it works.
Personal Archive Note-To-Self: One of the things I say to young professionals every chance I get is that all corporate-sanctioned or “official” mentorships are BS. You might win the lottery and defy what I’m saying here, but you probably won’t. That means beware of anybody calling themselves a teacher or a mentor as part of a formal status framework. Mat’s story here is why.
Apprenticeship is the real version of what most mentorship programs are supposed to be. You learn a craft by doing. They’re not there to like you, or shepherd your career, or anything else. You’re just there to learn. No fluff. You show up and you learn the craft, and it’s not always pleasant, but at least you know what the setting is and why you’re showing up.
You, as the learner, are first assessing from anybody in a teacher-type role, if they’re 3 steps or 300 steps ahead of you so you know how to frame their lessons. In Mat’s case, Lanny knew how to be 3 steps ahead, while existing 150 or so steps into the future. In this magic middle, you also have space for that lottery scenario I mentioned earlier to happen.
Sometimes, the person showing you the way, will actually care to take you under their wing. If you show up, if you’re genuinely interested, and if they’re in their status-spot for the right reasons, your life is about to change. And if it’s not, or even if something feels off, don’t take it personally, but learn what you can and watch for other people to align yourself with. I wish I knew that at a younger age, it’s so cool to see how Mat clearly did.
Work question for you: Who in your field knows enough to break forks and bring extra napkins? How can you position yourself to learn from them - not in a formal setting, but in the real moments where the actual work happens?
LIFE: The Productivity Trap Has No Exit
"I'm not sure they ever go away, man. It's a constant battle. I was listening to Oliver Burkeman about essentially how you can do as many things as you want to do, but the list never disappears. If you end up being the most productive person in the world, the only thing that you get rewarded with is more stuff to do. That is a new lesson for me on top of the perfectionist thing - they're interrelated. If you're constantly trying to be perfect and do everything and cross off your list and be Superman, you end up losing. It’s the Ferris Bueller thing, right? Life moves pretty fast. If you don't stop and look around every once in a while, you just might miss it. And that has happened more than once in my life because of those two tendencies."
Key Concept: Perfectionism and productivity are not virtues - they're a trap that feeds itself. The more you accomplish, the more appears on your list. The more perfect you try to be, the more you see what's imperfect. These tendencies work together to convince you that the next win, the next completed task, the next level of mastery will finally feel like enough. It won't. Mat learned this the hard way - by losing years of his life to the grind, only to realize he'd missed the actual living that was happening around him.
Personal Archive Note-To-Self: What’s the Seth Godin quote about races to zero? Something about how the worst thing that can happen to you in a race to zero is that you’ll win. The Burkeman quote hits like that. So does the Bueller quote.
In one set of hands they are traps. They’re ideals that you measure against. That ruler will kill you if you hold it up next to everything you do. The trick, so I think I’ve learned, even if I don’t practice it as well as I wish I did - is to use the ideal only for orientation.
It’s a lot like choosing mentors and teachers to follow. Once you know if you’re taking tactical advice or longer-term strategic thinking from them, then you put all the focusing on orientation so you never get too far of course until you are consciously choosing why to deviate.
Life isn’t any different. You don’t want to win in a race to zero, and you don’t want to be so good at getting boring things done that you end up with an endless stream of boring populating your days. The ruler is internal and it’s all about getting the direction right, not the measurements. More casual spaghetti sauce making and less expert baking.
Life question for you: Where are you losing the Ferris Bueller thing - the moments you're supposed to stop and look around? What would happen if you stopped trying to be Superman?
LEGACY: The Moment You Hand It Over
"I'm standing in the pit on Friday morning, right before Christmas, and I watch the cash print. I think it's incorrect. There's no possible way this is where it could print because I knew if it actually did, we were basically out of business. I wait and watch as each stock comes in, and the print changes a little bit. Sometimes it jumps or dips. And it didn't move. It was stuck there. I looked at my clerk who was standing on the rail above me, and I remember doing the math in my head and looking at the print. I took my computer handheld off my sling and handed it to him. It's like 8:00 in the morning and he goes, 'Where are you going?' I said, 'We're done, bro.' He goes, 'What do you mean?' And I said, 'Did you see where we just printed? Did you see where the cash print was?' He goes, 'No.' And I said, 'We just lost all our money. I'm going home.' So I went upstairs, grabbed my stuff, and I just left."
Key Concept: There are moments in your career and life when you realize that continuing is not perseverance - it's denial. Mat built a trading firm over ten years. He had momentum, capital, a reputation in the market. And then one Friday morning, the math told him it was over. The hardest part wasn't admitting it to himself - it was the action of handing over the handheld and walking upstairs. That's not quitting. That's clarity. That's knowing that some losses teach you lessons you only have to learn once, and you carry those lessons for the rest of your life.
Personal Archive Note-To-Self: After you figure out who to learn from, and how to orient yourself without strictly trying to follow impossible footsteps or worse, get dragged along, you start thinking of time differently. There’s a before and after awareness. Not necessarily in some before- and after-life way, but in an each chapter of life is temporal awareness.
You learn to accept moments. You learn to grieve some. You learn to let go of, if not entirely forget others, by choice and by happenstance because only so many things fit in your head.
I’m including this story for a Legacy reflection because it’s the moment Mat opts to close one chapter and go to the next one. It’s not comfortable and it’s not fun. It’s pretty heartbreaking, candidly, to hear him say it, and I’ve heard this story before and it still got me worked up, but - this, to me, is the most important aspect of legacy.
It’s not just about operating beyond your lifetime, it’s about operating beyond the chapter you’re in, with some humbleness, grace, and awareness that life is going to happen, and your job is to be alive while you’re here - like Mat was, when he handed the computer over and walked out to begin processing what just happened. I’m projecting here, but I don’t think any earlier version of Mat could have handled the moment quite this way and I find it especially mature and moving as a reminder.
Legacy question for you: What is something you've been holding onto that might be asking you to let it go? How do you know when it's time to hand it over?
BEFORE YOU GO: Be sure to...
Explore the educational resources at the Options Industry Council (OIC): optionseducation.org
Reach out to Mat directly at the OCC: [email protected]
Oh and - Cashman was on the FIRST “official” episode of Just Press Record. Relive the moment with me and Brian Portnoy here
Take a moment to reflect on who your napkin mentor is - and whether you're being that person for someone else
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.
ps. AI helped me pull and organize quotes from the transcript, structure the three lessons, and sharpen the Key Concepts. If you're curious about how I use AI while keeping editorial control and my own voice intact, I wrote about my personal rules here: Did AI Do That: Personal Rules
