- Cultish Creative
- Posts
- Grow Your Network: Bob Seawright Is A Better Letter Writer
Grow Your Network: Bob Seawright Is A Better Letter Writer
Here's HOW and WHY to connect with Bob
Matt Zeigler
May 09, 2025
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.
Find my Personal Archive on CultishCreative.com, watch me build a better Personal Network on the Cultish Creative YouTube channel, and follow me on social media (LinkedIn and X).
This approach has helped tons of clients strengthen their networks and unlock new opportunities. You can:
Steal these ideas directly
Hire me to implement them with you
Create your own combination that works for you
I can't promise you'll learn from me, but you'll definitely learn something with me. Let's go. Count it off: 1-2-3-4…
Do you know Bob Seawright? Author of The Better Letter whose writing blends market insights with music references and baseball metaphors? The former lawyer who found his way to Wall Street through a charity function conversation and media syndication rights dispute? The writer whose newsletter has inspired a 17-hour Spotify playlist curated by a devoted reader?
If not, allow me to introduce you. Bob has transformed financial analysis into thoughtful commentary on markets, decision-making, and life, all while weaving in cultural touchpoints from the Beatles to baseball. I wanted to connect with him because he embodies something I value deeply: the ability to bring humanity, wisdom, and a multidisciplinary perspective to technical subjects that often suffer from narrow thinking.
Our conversation is LIVE now on the Cultish Creative YouTube channel (and this Cultish Creative Playlist). Listen and you'll hear how Bob's path from law to finance coincided with his evolution as a writer seeking to understand and explain not just markets, but human behavior.
In the meantime, I wanted to pull THREE KEY LESSONS from my time with Bob 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 a Lie That You Can Be Anything You Want
"My wife says all the time, and she told her fifth graders all the time, 'it's a lie that you can be anything you want. You can't. There aren't restrictions on you other than your own abilities and your own willingness to try. But, if you're five-five and slow, you're not gonna play in the NBA, no matter how badly you want to."
Key Concept: True fulfillment comes from honestly assessing your actual strengths and limitations rather than chasing impossible dreams. Accepting reality isn't defeatist, it's the first step toward finding where you can truly excel and make an impact.
Personal Archive Note-To-Self: Life sorts us. Sure, we can bend certain parameters - but Allen Iverson aside (or, hell, Muggsy Bogues!), it’s good, and honest, and realistic to self-assess what we’re working with. Others can figure it out for themselves. Who am I to tell you what you can and cannot be? That’s on you. But, who am I to tell me? Probably the only person who can tell me, that’s who.
I know Mrs. Seawright wasn’t making choices for those fifth graders. I also know her definitions of restrictions, as natural abilities and willingness to try, are the key to Bob retelling the story. You can’t be anything, but you certainly can be something, and - you can be amazing at it.
Work question for you: What aspirations have you been pursuing that might not align with your natural strengths, and what opportunities might open up if you redirected that energy?
LIFE: Strategic Silence Creates Creative Space
"I tested not playing music... on Saturday mornings when I was doing chores. And I turned off the music and just kind of thought about stuff and I found I was unbelievably successful at finding stuff to write about or ideas or thinking through things because of the quiet. And I ultimately had to start putting a pad and pencil in my pocket to capture the ideas."
Key Concept: Sometimes the most powerful catalyst for creativity isn't more stimulation but its absence. Creating intentional periods of silence can open mental space for new connections and insights that might otherwise be drowned out.
Personal Archive Note-To-Self: My most creative moments happen when there’s no other stimulus. Frequently, they happen when I’m doing a mundane task. Dishes, dog walks, hikes - those are creative time. Like Bob, I can’t do background music or even background podcasts when I want the ideas to come.
Sure, the background listening during mundane tasks gives me notes, and I do do that a lot too, but those are starting points. If I want the reflection to start, I need the quiet. It’s space we need for ourselves, and it’s space we need to help create for others.
Life Question For You: What areas of your life might benefit from strategically reducing input rather than seeking more information or stimulation?
LEGACY: Writing to Test What You Really Think
"I eventually learned the best way for me to figure out what I thought and figure out, at least for my standards, if what I thought cohered was by trying to write it. I found lots of bad ideas out because I tried to write them and it just didn't work."
Key Concept: Writing isn't just about communicating what you already know—it's a tool for discovering what you actually think. The process of articulation forces clarity and helps identify flawed reasoning that might otherwise go unnoticed.
Personal Archive Note-To-Self: One of my favorite expressions is, “The trash can is your friend.” I love it because it reminds you that you don’t have to keep everything. As you work stuff out, as you iterate, you’re going to hit dead ends, and when that happens, the trash can is there for you.
Life doesn’t demand perfection. If anything, it dictates the abundance of imperfection. Befriending the trash can is as essential a first step as I can imagine for starting to figure out what tiny shrivel of your scribbles actually deserves to stay on your desk and get repurposed for further use.
Legacy question for you: What deeply held belief have you never fully articulated in writing, and how might the process of writing it out help you determine if it truly "coheres"?
BEFORE YOU GO: Be sure to…
Subscribe to The Better Letter on Substack
Check out Bob’s Bob Dylan covers playlist
Remember his advice to "never skip class" (whether literal or metaphorical), and
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.
Last thing: 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.