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... Jack Raines!
Do you know Jack Raines? He's an investor at Slow Ventures, author of Young Money: A Field Guide to Wealth and Purpose in Your 20s, and one of the sharpest voices writing about money, optionality, and internet culture for people who grew up online.
If not, allow me to introduce you. Jack turned a SPAC-trading Reddit habit into a Columbia MBA, a job at Robinhood's media arm, and now a career in venture capital - all while building one of the most-read finance newsletters on the internet, largely by refusing to shut up on Twitter.
I wanted to connect with him because he embodies something I value deeply: the willingness to treat your 20s like a portfolio, and to actually spend the optionality instead of just admiring it.
Our conversation is LIVE now on the Epsilon Theory YouTube channel (and this Cultish Creative Playlist). Listen and you'll hear how a South Georgia kid who didn't know a single person in the Northeast ended up trading SPACs from a bathroom stall, losing $160,000 in a single day, and turning both into a career.
THREE: That's The Magic Number of Lessons
In the meantime, I wanted to pull THREE KEY LESSONS from my time with Jack Raines 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: Time Is A Substitute For Data
"I think people seriously underrate intuition as a decision-making process. People try to overanalyze data points. In reality, you're constantly absorbing so many data points all the time that if you just take a step back and let your intuition cook for a little bit, it usually has a pretty good feel for what you should be doing and what you should not be doing, and I think people should trust that more."
Key Concept: Jack's take flips the usual advice about decision-making under uncertainty. Instead of treating more analysis as always better, he argues intuition is itself a form of data processing - your gut has already absorbed signals your conscious mind hasn't sorted through yet. The discipline isn't gathering more inputs; it's trusting the read you already have.
Personal Archive Note-To-Self: Trusting your gut gets a little bit easier with age, but the whole process is eternally humbling. I think it's because intuition is such a murky term. We know it's full of bias and incomplete variables/context, but when it comes down to time to decide, we're still humans - and humans decide, they don't compute.
In my professional work of giving advice around financial decisions, we live this every day. I can build and model and explain the optimal version of a decision, but a real live human still has to choose. That means we never present binary options. Pretty much everything we do comes with ranges and tradeoffs and "how will you sleep if you do this one" questions.
Which all means intuition still plays a role. Experience and knowledge do compound, in good and bad directions (!), so what we're really trying to do is have good counterbalancing elements anytime there's a big decision on the line. And if you're short on data, time is a good substitute.
Decision making will involve your brain. Don't be scared of it. Get it the information it needs, but also respect the intuition you'll ultimately rely on to move forward.
Work question for you: Where in your own decisions have you been overanalyzing when your gut already knew the answer?
LIFE: Spending Tuition Via Attention
"If you're in a high optionality part of your life, I think it's pretty crazy not to maximize that optionality and take advantage of it because you just don't know how long that window of time's gonna last... I would say I spent most of my 20s exploiting optionality and did a good job of it. And now it's like I'm transitioning to call the shots you wanna double down on."
Key Concept: Jack treats optionality as a finite resource, not a permanent state. Being unattached - single, no kids, no mortgage - isn't just freedom; it's a closing window that most people don't recognize until it's shutting. His framing reverses the usual story: the goal isn't to keep your options open forever, it's to spend them deliberately before life narrows them for you, then shift into betting big on fewer things once you know what you're betting on.
Personal Archive Note-To-Self: There's time in decision making and then time in the phases of life. Both are fleeting and under pressure. I can think of my mid/early career time, when I started in finance in my mid-20s and then all the way into my mid-30s, where I wasn't maximizing optionality for the career so much as I was maximizing optionality for what I was learning. I did it all the backwards ways, but without any school time having been studying this stuff (no college courses, no MBA, etc.), I was using the paycheck to learn all about business and markets.
My intuition was in the right place, even if my ambition was a bit impostor syndrome riddled and understated. In that sense I envy what Jack's been up to as he works his way through this phase.
But not everyone gets that phase in their 20s - and that's fine. For the career switchers and multi-hyphenate slash artists out there, it's good to create time and space to learn, too. Because learning puts new things on the table, and as I've found well into my 40s, as I've expanded the footprint into podcasts and YouTube and more online stuff, all that mind expanding optionality can pay off.
If you're spending tuition via attention, just don't waste it.
Life question for you: What season of optionality are you in right now - still spending it, or already transitioning to double down?
LEGACY: The Gut Says It's Okay
"Every single thing was driven by some asshole wanted to do something and he's decided to do it, and his motivations for doing that were either driven largely by insecurity, money, or sex. And that's kind of like the entirety of human history - you either want more money, you want more sex, or you just wanna be better than the people around you."
Key Concept: This lesson didn't come from a textbook - it came from Coach Koran, Jack's high school history teacher, who painted his classroom like a medieval map and taught through the protagonists of history rather than dates and outcomes. Jack's takeaway wasn't really about history at all: it's a lens for reading motive underneath any surface-level story, whether that's a king starting a war or a market bubble forming. It's a framework Jack still uses to read the world well beyond the classroom it came from.
Personal Archive Note-To-Self: The problem with intuition and ambition is the sneaky aspirations that can skew our human judgement. This lesson, from Coach Koran in the history classroom, is as profound as it is important. Insecurity, money and sex are all aspirational drivers, and world history is riddled by powerful people pushing the limits in multiple categories at once because their gut says it's okay.
We're all susceptible to this, too. Not in the most extreme cases, but this is what makes us human. This is why optimal decision making is tough, and why you'd better consciously make room for some gut-based choosing, otherwise your most basic instincts are going to get into your trash raccoon style, anyway.
The most admirable detail here is how aware we stay of our decisions as they affect us, and our decisions as they affect those around us. Coach Koran's decision to take a teaching spot at his kids' school is a great example. His intuition and ambitions lined up in a way that powerfully impacted Jack. He didn't fall victim to much of what they were studying in class, and yet lived by that example of showing the right behavior and choices, forward.
Legacy question for you: Whose framework are you still carrying with you, years after they first taught it to you?
BEFORE YOU GO: Be sure to…
Check out his newsletter, Young Money
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
