Newsletter #3

Greetings!

This week’s newsletter is a mix of the familiar and the new.

My dad told me a great story this week, and I can’t not share it. So here we go!

A Little Context

My dad is a Marine. After completing his first contract, he transitioned to reserve duty and needed to find a job. One day, he walked into a hotel to apply for an open bellhop position. He handed the hotel manager his resume, only to have it immediately tossed back at him. The manager offered just one piece of feedback amidst the rejection: “There’s nothing on this resume that shows me you can carry bags.”

Here was a man who had spent six years in the Marine Corps, yet was deemed unqualified to carry bags.

The takeaway? Sometimes, the gatekeeper’s mood determines whether the light is green or red.

My dad shared this story with me as I’ve been searching for my next move. His lesson was clear: sometimes rejection is about you, but just as often, it’s about the person doing the rejecting.

The Hero’s Journal

We rejoin our characters at one of the most critical moments of the story: the point of no return—or, as I like to call it, the “go, no-go” moment. This is where the quest becomes real.

Up until this point (July-ish 2018), the journal was simply a thought exercise. It was something two friends explored to learn about themselves and toy with possibilities. But now, we faced a pivotal decision: we needed to hire a designer.

If you know Nick and me, you know this: we’re creative but utterly incapable of drawing even a stick figure. To bring this project to life, we needed someone who could visualize our imaginations.

So why was this the “go, no-go” moment? We were both fresh out of college and weren’t exactly flush with cash. A good designer costs money, and putting what little we had into this side project was a real risk.

Here’s where my dad’s story ties in. When we posted a job description on Upwork, we got 5–10 resumes and set up 2–3 interviews. I think we even had one call, but then the most magical thing happened. We received a resume from Ryan McConnell.

Ryan’s resume was the polar opposite of my dad’s. It wasn’t just designed and written flawlessly; it also had a distinct high-fantasy flair. Most importantly, it screamed, “I can carry the bags.”

Nick and I were blown away. We canceled the remaining interviews before even talking to Ryan. Fortunately, he was just as excited about working with us. The decision was made: Go.

Atypical Life

“I want to build cool things with people I care about.” That’s been my mantra for the past few years—a guiding thesis for how I spend my time.

I’m including this in the Atypical section because Trey and I have adopted this mindset as a core inspiration for the brand. A few years ago, I read Conscious Leadership by John Mackey. It introduced the idea of creating “Win-Win-Win” situations in business (win for the company, win for the customer, win for the employees). This mindset adds another “win” for us: building something that lets Trey, our team, and me enjoy each other’s company while creating tools that genuinely help people—and are cool.

I mention this because I just got off the phone with Trey, and he repeated my own words back to me. Having a North Star is great because even when you can’t see it, others often can.

Keep pushing.

Book Time

“I caught a wave and rode it. Then I caught another wave. Then another.”

I’m nearly done with How to Know a Person, and the last act of the book is deeply story-driven. If you know anything about The Hero’s Journal or how we approach life, you’ll see why this resonates.

The quote above redefines how we think about life. Many of us see life as linear: I want to be an astronaut, so I get good grades, join extracurriculars, go to astronaut school, and become an astronaut.

But if you know anything about great stories, you know that’s not a very compelling one. A great story has twists, turns, ups, downs, and, most importantly, failures. This quote offers a different perspective—viewing life as a series of waves to catch and ride, one after the other.

As I mentioned during my dad’s story, I’ve been trying to figure out what my next wave is. This realization helped me see:

Life doesn’t have to be about riding just one wave. It’s about catching many, each with its own unique themes and challenges. Don’t force it—live it.

Coffee

Last week, I dove deep into coffee. This week, I’m keeping it simple: my girlfriend’s coffee.

She’s been drinking a medium roast from Colombia that she bought at Vons near her house. It’s not a coffee I’d normally pick, but it’s her favorite—and that makes it special.

Fancy coffee with intricate brewing instructions is great, but so is pre-ground coffee brewed however you like. The most important thing about coffee? Drink what you love.

For me, this one’s okay. But for her? Perfect.

Summary

If you’ve made it this far, thank you. If you’ve followed along for three newsletters now, thank you even more.

Right now, my path feels unclear, but I’m reminding myself to wait for the next wave. The best part about the wave analogy? You don’t have to ride every wave—you get to choose.

Keep on keeping on.

Kyle