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... Kevin Alexander (Again)!

Do you know Kevin Alexander? We connected with him before to talk about music curation and discovery, but he just came back on Just Press Record for round two - and this time we dove deep into something even more important than what to listen to: how to actually think and write about art in a way that matters.

If the first conversation was about finding great songs, this one is about becoming the kind of guide people actually want to follow. Kevin spent our time together reviewing the new Glitterer track "Stainless Steel," unpacking his writing philosophy, and - this is the wild part - articulating a philosophy of impact that goes completely against the grain of how most creators think about success.

I wanted to bring him back because he's demonstrating something rare: the ability to scale your impact without abandoning your integrity. He's not trying to be Pitchfork or Stereogum. He's building something smaller, more intentional, and infinitely more valuable to the people who actually show up.

Our conversation is LIVE now on the Just Press Record YouTube channel (and this Cultish Creative Playlist). Listen and you'll hear us dissect music reviews, talk about the art of knowing when to stop editing, and explore what it actually means to spread ideas instead of scale them.

THREE: That's The Magic Number of Lessons

In the meantime, I wanted to pull THREE KEY LESSONS from my time with Kevin Alexander (take two) 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: Write The Review That Only You Could Write

Key Concept: In a world where AI can generate technically competent reviews in seconds, the only defensible position is radical authenticity. Kevin understands that your value as a critical voice isn't in polish or professional distance - it's in the specificity of your perspective. The best art writing captures the real-time experience of encountering something new, messy thinking and all. It's the difference between reading about a song and hearing from someone actually listening to it.

Personal Archive Note-To-Self: I had a moment the other day, when Claude (my AI editor) went down, and a state of self-editing panic came on. It was like - the first time the training wheels are off and, you know you want to do it, you know you probably can do it, but oh, the doubt, and the potential stupid looking and painful risk you’re about to take.

Maybe the biggest problem I have with AI is how great of a set of training wheels it is. I don’t worry about it making stuff because that’s, I don’t know, full “bubble boy” risklessness and therefore inherently uninteresting? But these micro reminders, that the risk is what begets the returns, is worth remembering here.

Kevin wanting to write in real time is the type of kid on bike without training wheels I want to be there for. I accept that there will be basic misspellings and less than perfect sentences. But I also accept there will occasionally be both dead-ended logical traps AND brilliant breakthroughs I’ll be thinking about for days. And the beauty is, none of the stumbles will be life ending, but the successes could be life altering - for writer or reader.

Reflection and curation are a form of making. Making requires risk. We're drawn to people like Kevin because audacity is magnetic - it gives us permission to be less polished too.

Work question for you: When was the last time you let someone see you think instead of just showing them your finished conclusions? How would your work change if you prioritized authentic thinking over polished presentation?

LIFE: Know When To Let It Go Before You Get In Your Own Way

Key Concept: Perfectionism isn't a virtue - it's a trap that keeps meaningful work locked away from the world. Kevin's insight is deceptively simple but profound: there's a point where more editing doesn't improve something, it just suffocates it. You have to develop the judgment to recognize that moment. This isn't permission to ship half-baked work; it's recognition that "ready enough" is often ready, and the act of releasing something is part of the creative process itself.

Personal Archive Note-To-Self: Kevin Leahy said something on his Just Press Record he learned from his comedian brother - that eventually, you just have to leave the house. There’s a big, imperfect, and sometimes scary world out there. You aren’t going to want to leave the places your comfortable to explore it, by default. But, if you want to do anything noteworthy, eventually, you’ll have to.

Now, once you go out and see the world, you can come home and work on it. You can hear the band and buy the album and come home to work out the review in Kevin Alexander’s space. But then, an inversion of the Leahy idea comes back up. You have to release your idea back into that big scary world again!

This is the risk points from the previous section again. If you don’t accept that endlessly insulating and insuring your idea from flaws is impossible, you’ll never get out of your own way. You have to get outside first. Then, come back inside to work on things. But after you do the work, you have to get that idea out of the house again too.

Ready enough is all the ready you’ll ever need.

Life Question For You: What project are you sitting on right now that you know is ready enough? What's actually holding you back from sharing it?

LEGACY: Great Art Doesn't Scale - It Spreads

Key Concept: The most important reframe in modern creative work is understanding the difference between scaling and spreading. Scaling is mechanical - it's about systems, optimization, and reaching the next million users. Spreading is organic - it's about people who genuinely care about your work telling other people who might care. Kevin has built something that spreads precisely because he's not trying to scale it. He's created a 200-person club that's more valuable to each member than a 20,000-person audience would be, because every single person feels seen and known.

Personal Archive Note-To-Self: If Kevin agreed to come back on Just Press Record, and then I just press record, and all he said to me was, “Hey Matt, good to see,” which is where he’d start because he has manners, and then he said, “Great art doesn’t scale. It spreads,” we could have ended the whole conversation right there and I would have been delighted.

Less delighted than I was by our entire hang, but - what a sentence. Tattoo it onto my knuckles, inject it into my veins. I am so sick of scaling being labeled a virtue in and of itself.

If risk begets return, you might start to think about how you need more and more risk for more and more returns. While this isn’t entirely true (or entirely false, but that’s not for this post - never ask a finance guy this question, ugh), the point is - eventually you have to ask, “Why?” Or, at least, “What for?”

Panera snazzily titled “you pick 2” meals or whatever they’re called, they’re marketed and sold and grandparents who are ok standing and ordering because it’s cheap, and teenagers who can press an iPad for food without talking to anyone will keep the company in business for a long time. But. Is Panera great food? It’s ok food, sure, but this is where the term “premium mediocre” works for a great reason, right?*

Great art is no different. Its purpose can’t be to appeal to a wide audience who thinks, “it rhymes so I don’t have to think.” This is coming from me, a man of convenience, too. Great art is something you can’t wait to tell someone about. And that requires the risk of them not agreeing, and the risk of you not being able to clearly articulate the idea itself.

Kevin lives this in his writing for On Repeat Records. He wants to tell you something. He wants you to decide if you’ll tell someone else. There’s no snazzy hooks. Just a lot of great music with a community to talk about it with.

Legacy question for you: Are you optimizing for scale or for spread? What would your work look like if you prioritized the deepest possible impact on the smallest possible group of people?

BEFORE YOU GO: Be sure to…

• Subscribe to Kevin's "On Repeat Records" Substack at thekevinalexander.substack.com

• Check out his weekly music reviews and literary reflections

• Follow him on Blue Sky @KevinAlexander (or Instagram, Twitter, or LinkedIn)

• Listen to the full conversation where we break down the Glitterer song “Stainless Steel” together

• Take a moment to reflect on all these ideas!

• *footnote! I wrote a music post about Premium Mediocre stuff back in 2018 called, “Relevance: Drake and The Carters” which I’m still pretty happy with. You can check that out or the OG Venkatesh Rao piece, “The Premium Mediocre Life of Maya Millennial”

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.