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 Jack Boudreau? He's the CEO of Habits, a content creator with a loyal following across TikTok, Instagram, and Substack, and a former JPMorgan investment banker who got the job by bluffing his way through a phone call from Amsterdam while his friends waited at the bar.

If not, allow me to introduce you. Jack built his audience by doing the thing most people are too polished to do - sharing the honest, sometimes embarrassing, always instructive story of figuring it out in public. He's the guy who studied abroad in France without speaking French, interned at a bank in Shanghai without knowing Mandarin, and bootstrapped a fintech company from his buddy's rental property in Indianapolis dressed in a suit every day for no one but himself.

I wanted to connect with him because he embodies something I value deeply: the willingness to be radically uncomfortable on purpose, and the self-awareness to know exactly why he keeps doing it.

Our conversation is LIVE now on the Intentional Investor YouTube channel (and this Intentional Investor Playlist). Listen and you'll hear a guy who has turned "Boudreau's finish strong" from a childhood house rule into a full operating philosophy - and who will make you feel considerably better about still feeling behind.

In the meantime, I wanted to pull THREE KEY LESSONS from my time with Jack Boudreau 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: The algorithm doesn't care how long you've been around - it rewards the content itself, regardless of follower count. That makes TikTok a uniquely honest feedback environment: a bad video disappears quietly in front of strangers, a good one finds an audience it never expected. Jack used that mechanism deliberately - not to go viral, but to iterate. Every post was a low-stakes experiment with an honest verdict.

Personal Archive Note-To-Self:

I remember looking at TikTok when it was a step past being Musical.ly and thinking - "they made crack for kids, step away, old man." My ADHD-addled brain doesn't need that level of stimulation, and even if I'm always fascinated by why kids are into what they're into, especially if their parents are scared of it (a bat signal for the new cool), the part that impressed me was anybody could be a star on those platforms.

You didn't have to do the hard work of building up a following first. You didn't have to be perfectly suited for this, or polished, or have anything else beyond a phone with a camera and an internet connection - which meant the bar was lower here than probably anything else a young person has access to to be seen.

Now, to be seen does not mean to be liked let alone loved, and this is where the crack metaphor applies because social media will make your teeth and hair fall out in clumps, but if you can take this lesson on low stakes experimenting without getting addicted to unpredictable fame, it opens lots of doors to what else you can do with life.

I'm way happier writing Cultish Creative posts than making TikTok videos, but someday it'd be fun to have a million people see something I did. I'd be lying if I said otherwise. But finding your sandbox to learn those lessons in, of how to participate on a platform where you can tinker, it's a key to life if you can keep from getting hooked on the bad stuff.

Work question for you: Where in your professional life are you getting honest, low-stakes feedback - and where are you avoiding it because the audience feels too close?

Key Concept: The scoreboard problem has always existed - net worth, job titles, family timelines. What's changed is that follower counts and posting frequency have added a whole new leaderboard running in real time alongside all the others. Jack's point isn't that we should stop caring, but that the feeling of being behind is so universal it might just be a feature of this particular window of life - not evidence that you actually are.

Personal Archive Note-To-Self:

Jack calling out the "I am so behind" age gap here - I told him after we pressed stop how lost I was from about 25-35. 35-(almost)45 has been all about dismantling the scoreboard in my own life. Let's just say I can really relate to all of this.

Those two decades are a different kind of middle age. You pull out so many rulers and wonder why you haven't figured out what the others have figured out. My wife knows all my touchpoints. If I so much as mention Beyoncé she knows I'm thinking about how she's the same age as me and "What am I even doing with my life" is about to come out. The Beyoncé ruler is real, and that one has only grown since she was in Destiny's Child and I was still destined to be a child for much, much longer.

Getting comfortable with still being competitive without being comfortable in an unhealthy relationship with addiction is a real step in maturity. I'm not saying I'm there, but I am saying Jack knowing the scoreboard never turns off at his point in this journey means something.

Life Question For You: Which scoreboard is running loudest in your head right now - and is it one you actually chose to play on?

Key Concept: "Boudreau's finish strong" isn't about achievement - it's about integrity of effort once you've made a commitment. The Boudreau household rule wasn't that you had to love everything you signed up for. It was that quitting halfway through taught you nothing useful, while finishing - even miserably - gave you real data about what to do next. That's a different kind of discipline than grit for grit's sake. It's information-gathering through follow-through.

Personal Archive Note-To-Self:

I love a good house rule. The sheer labeling and branding of it, too - there's a marketing lesson here that I hope nobody ever puts in listicle format (that I'm also positive is out there on LinkedIn and - blech.) I love it because it's a small community rule that makes no sense to people who don't already know what it means, while at the same time reinforcing the culture for the group that takes it as gospel.

I'm thinking of mosh pit rules ("if somebody falls we pick them up"), and misc. friendly aphorisms ("always go to the funeral"). If you're not in the clubs that say stuff like this, you see or hear them and give a "what's that now?"

Which, isn't this what legacy is all about? Making little communities in your life, belonging to them, contributing to them, where there's a preponderance of rules and expressions just like this? They are slightly scaled up inside jokes. They're the ways we signal we're in the group AND that the group has values.

Legacy is all about reinforcing that which deserves to be reinforced. As an old man who wants you to "leave that (social media) crack alone" and "let Beyoncé's be Beyoncé's" - this is me at 44 and change focusing on my internal ruler, presenting it for anybody who gets it, and encouraging competition to be a better version of myself, without still being convinced I need to be someone else. Jack's passing that message down already, too.

Legacy question for you: What's something you've been quietly quitting on - and what would it mean to finish strong anyway?

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