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!

Do you know John Montgomery? He's the founder, CEO, and portfolio manager of Bridgeway Capital Management in Houston, a firm managing north of $5 billion that gives a portion of its profits to charity through the Bridgeway Foundation.

If not, allow me to introduce you. John started Bridgeway in 1993 after turning a business school hobby in quantitative investing into a for-profit firm, and he built generosity into it from the first profitable year.

I wanted to connect with John because he embodies something I value deeply: living his legacy now instead of waiting for the will.

Our conversation is LIVE now on Epsilon Theory YouTube (and this Cultish Creative Playlist). Listen and you'll hear how a broken wrist turned a guitarist into a flutist, why Bridgeway doesn't use the word "employee," and how a Quaker-founded college, a Watergate semester, and a bus company shaped a quant. You'll also hear about his partner in charitable giving, Shannon Sedgwick Davis, the CEO of Bridgeway Foundation and author of To Stop a Warlord (who probably needs her own episode after this!)

In the meantime, I wanted to pull THREE KEY LESSONS from my time with John Montgomery 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.

Key Concept: Montgomery was a 24-year-old general manager of a small bus company in High Point, North Carolina, when he watched a colleague handle hard conversations and realized he avoided them. Elsewhere in the conversation he says he was strong at relationships and caring about people, so the gap was specific, not general. His response became a career-long practice: make room for your strengths because they won't surface on their own, and for the weaknesses, either get better or hire people who are great at them.

Personal Archive Note-To-Self:

I'm endlessly amazed how everybody has something to teach you. Sure, most of the time, especially early on in your life or with early work experiences, they're cautionary tales, but as life progresses and you start to get exposed to people who seem to have their crap together, the lessons worth stealing start to show up in meaningful ways. John finding this at 24, and realizing he should start practicing this skill his partner Buddy had, is enviable.

Working construction at 15, I remember learning the lesson, "You don't have to work so hard. They're paying you by the hour, so you only win by the hour." Paul Westerberg describes that as "minimum effort for minimum wage" and, it's simultaneously not how I'm wired but not wrong, either. I think about that, a lot, because it just reminds me I'm not wired like everyone else and I shouldn't be so naive as to think that way.

Later, in my early 20s, my boss in a recording studio taught me the opposite lesson. About how we ask for more money because we work harder and better than the people who do supposedly the same job for less. It meant people would scoff at our proposals sometimes and say no to projects with us, but he'd tell them, "We'll be here. It's no problem. If you go do it somewhere else and figure out it needs to be fixed or redone, just call." I learned how to match my work ethic to the expectations in those experiences, even if it would take me another decade (plus!) to even begin to start applying it.

Work question for you: Who do you work with that handles a hard conversation better than you do, and what have you picked up from watching them?

Key Concept: Montgomery became a father at 22. His eldest daughter Katherine, now a psychiatrist who works with PTSD at a VA hospital, went through therapy as part of her training and came back with questions about how she was raised. Elsewhere in the conversation he admits he gave her more responsibility than she deserved, and he doesn't dispute any of it. What he offers instead is context, and the moment lands because it holds accountability and compassion at once.

Personal Archive Note-To-Self:

The way we move from being the student to the teacher, or the child to the adult - all without much ceremony or graduation typically, is disorienting and weird and I, at least, need reminders of this all the time. Mostly because the reminders give us the context that John offered his daughter here. We are all moving in parallel and experiencing these shifts. There's kindness in being reminded of this.

As part of a generation who has normalized therapy, behind multiple generations who only kinda sorta have, I'm sympathetic to both him and his daughter when he tells this story. You want to have, and win, some kind of self-awareness contest when you face certain frustrations. You want to think you'd have done it all better. But then you adjust your frame of reference and realize life is hard, for all the reasons.

Complex might even be a better word than hard, but anything that reminds us of the nuance, and to have a generous interpretation that assumes more context than you can ever know is the right starting point. Yes, sometimes you'll find out something was just plain wrong, and that's when you can establish a real or psychological boundary in your mind, but most of the time people are just doing their best under insane amounts of pressure and stress, and it boils down to what we're willing to accept, and all we can do with the rest is sidestep it.

Life Question For You: Whose choices have you judged without remembering how old, or how unprepared, they were at the time?

Key Concept: Montgomery's giving started as a worry. He grew up around wealth in Houston and didn't want to raise "trust kids," and that worry became a design choice for the company: give a portion of profits along the way, with no models in his industry to copy. Elsewhere in the conversation he says that of his original dozen ideas for Bridgeway, this "naive" one proved ten times more powerful than he expected. The first year's profit was $30,000, enough for a small donation, and the habit has scaled with the firm ever since.

Personal Archive Note-To-Self:

John choosing to live his legacy in the now, over and over in this story, is part of why I look up to him. When I play back those old job stories, and watch the minimum effort for minimum wage psychology evolve into fair wage for fair work, I feel the arc of how this builds. I feel the arc of how it forms, inside of a person, and then doesn't just stop at an event, like the people who save up all their money and hoard it until they die.

My financial planning day job now sees variations on this. I think through it with people, reconcile the decisions of others when this stuff lands in a client's lap after a death, and all the variations in between. But what I feel most, in John's stories, is how much awareness and impact go hand in hand when you let them.

If there's always going to be more to do, anyway, then what's a small thing you can do today, and why not do it? It can be charitable. It can be bigger than you. It can be next to nothing, but it puts a smile on somebody else's face and guess what - that still matters. It's a story of habits that compound in a direction you can look back and be proud of, and look forward and be excited about.

I felt like I had cautionary tales for teachers at 15, versus some solid role models in my early 20s. The gift is in the compounding of these lessons, and finding our personal resolve to know what feels right in our hearts. I have so much respect for what John's built.

Legacy question for you: What could you start giving now (time, money, attention) instead of saving it for later?

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