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... Craig Wilson!
Do you know Craig Wilson? He's a Tennessee farm kid turned Harvard MBA turned Texas banker turned investment manager who spent four months in 2016 unable to sleep - and came out the other side a fundamentally different person.
If not, allow me to introduce you. Craig spent decades as a self-described "doing machine" - banker, rainmaker, family office executive, the guy who delivered Pearl Brewery in San Antonio when everyone said it couldn't work. Then his body forced a reckoning his mind had been avoiding for thirty years, and he had to relearn what it means to simply be.
I wanted to connect with him because he embodies something I value deeply: the willingness to let a crisis actually change you, instead of just surviving it and going back to the same patterns.
Our conversation is LIVE now on the Epsilon Theory YouTube channel. Listen and you'll hear how an English degree and a banker's instincts collided with a breakdown, a sabbatical, and a single word - shalom - that rewired how Craig shows up in the world.
THREE: That's The Magic Number of Lessons
In the meantime, I wanted to pull THREE KEY LESSONS from my time with Craig Wilson 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: It's All Being, No Doing
"I did everything I did in every sphere of my life in order to be proven worthy of love and respect, which is impossible. And avoid being judged, which led me to be guilty and ashamed, which is also impossible. So I manipulated life to turn out somewhere between those two things, and it wore me out, literally wore me out. I shifted from 'I'm not good enough' to 'I am a man of peace, powerfully present, and joyfully creative.' There is no doing in that. It's all being."
Key Concept: Craig spent thirty years measuring his worth through performance - grades, deals, hours logged - chasing two impossible targets at once: proving he deserved love and avoiding judgment. That chase is what burns people out, not the work itself. The shift he eventually made was from a doing-based identity (what I accomplish) to a being-based one (who I am, independent of output). It's a distinction worth sitting with before burnout forces the question.
Personal Archive Note-To-Self: Just wanting people to like me has gotten me into so much trouble it's not even funny. Craig's performance addiction hits a little too close to home in this way. I know exactly what he's talking about when he's explaining the love and respect ruler.
It's useful to know where it comes from in your background. I know mine is a source of the entertainer role I'm so naturally drawn to. I like being on stages (literal and virtual) because if everybody is smiling and nodding along, in that moment I know I'm worthy. As soon as the show ends or if an environment feels on edge, I feel the call to get on stage again and make sure everything is ok.
It's not a reasonable ruler to use. You can't let the environment dictate how you live. There has to be a balance. For Craig, he found it in the statement that he's a man of peace, and that means he enters, exits, and exists within any situation as a peaceful entity, not one called to put on every hat and put out every fire. That's huge!
For me, it took a long time and a lot of work, but I had to learn that I got to choose when to perform, and it wasn't a necessary act at the first sense of needing to cool down a conflict or keep people from looking bored.
Work question for you: Where in your own life are you still trying to prove something through performance - and what would it look like to simply declare who you are instead?
LIFE: Even On Vacation, I Was Working
"My wonderful wife says to me, 'What the hell are you doing?' And I'm like, 'What do you mean, what am I doing? I'm on my sabbatical.' And she's like, 'You've got a work plan for your sabbatical.' Busted. I was a doing machine. I had been a doing machine all of my life. Even when I was on vacation, I was working mentally, if not on the phone or computer."
Key Concept: Craig took a 90-day sabbatical specifically to stop - and immediately built himself a work plan for it. It took his wife pointing it out for him to see what he couldn't see in himself: the compulsion to produce doesn't pause just because the calendar says "time off." Real rest isn't the absence of a job, it's the absence of the need to be doing something at all. That's a much higher bar, and most of us haven't cleared it.
Personal Archive Note-To-Self: How is it I can hear my wife's voice telling me the exact same thing? The performance mindset in a nutshell. We know the show must go on and we are the show, so - we must go on. But even shows have nights off. Even shows break for seasons.
There's an expression in music usually (mis?)attributed to Miles Davis or Claude Debussy, that music isn't just the notes, but the spaces in between the notes, too. Grooves and rhythms happen when the foot goes down, and then in the space between where the foot comes down next. It's common sense, but hardly intuitive. Why should life be any different?
We need moments of silent motion in life. Moments we don't control or micromanage. We need space to let things breathe and that means we have to, no matter how hard it is, occasionally let go and only return after our pause is complete.
Life Question For You: If someone who loves you looked at your last "day off," would they see rest - or just unpaid work?
LEGACY: Who The Hell Are You, And What Did You Do With Craig?
"The English word for peace essentially means Matt and Craig are not in conflict. Then I came across the Hebrew word shalom, which in its fullness means whole and complete. I came back to work and people were like, 'Who the hell are you, what did you do with Craig?' That's the level of transformation."
Key Concept: Craig went looking for one English word and found a different idea entirely. Western "peace" just means the absence of conflict - a low bar. Shalom means wholeness, completeness - a much bigger promise, and one that requires receiving rather than achieving. The proof wasn't a journal entry or a renewed sense of purpose he kept to himself - it was visible enough that colleagues noticed it from across a glass-walled office before he said a word.
Personal Archive Note-To-Self: I heard a story through the grapevine about myself, from the eyes of somebody else who knows me very closely. They were telling my wife, "He smiles differently now. I knew him then, and he still smiled a lot, but it wasn't the way it is now. Anybody who has been around him for the past 10+ years would tell you the same thing."
When Craig explains shalom, and how peace is not the same as being a single piece (!), I feel my previous, compartmentalized, fractured self, I feel the must-perform/constant doing-machine energy I spent ages 25-35 sharpening to a razor's edge, and I'm just grateful I didn't have to not sleep for a number of months to figure it out.
I still do too much (probably). I still smile all of the time (guilty). But there's a peace to me. And the peace comes from feeling like one piece of myself, and not 10,000 pieces of what everyone needs me to be all of the time. I still know how to go in those modes. I still know how to contribute in a way greater than myself. But, like Craig, I feel the weight of knowing how to let go of the ruler and anchor myself back to focus that I will never, ever take for granted as a lesson learned and earned.
Legacy question for you: If the people who know you best saw real transformation in you, would they actually notice - or are you still performing the same role you always have?
BEFORE YOU GO: Be sure to…
Connect with Craig Wilson on LinkedIn
Learn more about his work as CEO of Silver Ventures & Pearl
Check out his story on the Intentional Investor episode in full
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.
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
