Losing the Thread to Find the Thread

Last week threw me off, not dramatically, but just enough to rattle something loose. My email service dropped my plan as soon as the trial ended—part of the newsletter course I was following—and while I’d expected a downgrade, I didn’t expect the way it made me reflect. I’ve already talked a bit about it in the last issue, but what I came away with was this: maybe newsletters shouldn’t the center of my creative energy after all. Maybe they were just the excuse I needed to hit record.

Because when I think about what actually excites me—what I feel pulled to do—it isn’t teaching, and it’s not even synthesis. It’s speaking, sharing my thoughts and experiences, doing the things other people thinking about doing but never actually do. It’s thinking out loud while I’m still in the mess (I’m usually in a mess). And if there’s a thread through all of this, it’s the desire to document—not the lessons, but the process. Anybody can interpret the process however they want and glean their own lessons, and that’s probably better than me trying to tell them what they should learn anyway. I’m in the early stages of something real, and that’s worth capturing while it’s still raw and pre-success (or pre-failure).

Level One: Start the Game

I’ve been saying this feels like starting a new game—Ready Player One style. I'm not bringing in a pre-built plan or some grand strategy from the jump. I read books and watch YouTube videos like everybody else, but I’m here as a new player, with curiosity, instincts, and a hunger to build something that’s actually mine.

I want to become a business owner. A CEO. That’s the dream. Not for the title, but for what it represents: autonomy, challenge, leverage, creativity, legacy. And eventually, generational wealth. But that dream is a heavy one. I’ve been thinking about the real weight of it lately—the risk of getting into a bad deal, or worse, getting into a good deal and then becoming the reason it fails. I can imagine both. I can feel the fear from both angles. The fear of overpaying. The fear of stepping into operations I can’t fix. The fear of letting people down. But underneath the fear is this deep, persistent desire to learn my way through it.

And I am obsessed with learning. Always have been. These days it’s small business acquisition, private equity, deal structuring, business operating models, and what makes a good company great. I’ve been going down rabbit holes I didn’t even know existed a few months ago. Learning words and terms I had never heard before. Feeling overwhelmed, like my software experience has kept me under a rock, isolated from all of these mechanisms of real-world businesses. Reading until my eyes burn out of my skull. Using my new best friend ChatGPT to run mock analyses of business listings I know I won’t buy, just to train the muscle. It’s not academic. It’s almost physical. I want to understand how these businesses breathe.

Jet Lag and Recalibration

This past week, I flew back from China, and my body still hasn’t landed. Right now, I fall asleep around 3 p.m., wake up at 11 p.m., and then I’m just… up. All night. All morning. Through lunch. Through early afternoon. Until it starts all over again.

The jet lag has been rough, but it’s more than that. I’ve just felt off-rhythm. Not in crisis, but in disarray. Disorganized. Which is kind of my default. I keep most of my thoughts in my head. Plans, priorities, to-dos, ideas—they rarely make it to paper. I hate writing things down. And usually once you write something down, it immediately becomes out-of-date. My brain moves too fast for notes. But when it comes to expressing things to other people, I can write. I can speak. That part comes naturally. I love texting essays to my family and friends (I wonder if they love reading my word-vomit text essays… hmmm…). And I’ve started to think, maybe the way through all this isn’t to force myself to become someone who tracks every task, but to lean into my own language—talk it out, share it in real-time, and build the habit of documenting without slowing myself down.

Speaking Over Typing

A few days ago I recorded my first video. It was just me, walking through what I’m building, where I am, what I’m thinking. No real editing. No polish. It’s not a pitch. It’s not for virality. It’s more like a log. Something I can look back on and trace the steps. And if I’m successful one day, I’ll have a complete history of this journey. That’s the goal.

I’m experimenting with some AI tools to help clean it up—just enough to make it watchable—but I don’t want to lose the texture of the moment, or waste time on editing and engagement metrics. That rawness is the point. I don’t want this to become a content machine. I want it to be a record. A path. A breadcrumb trail.

Right now I’m reading Buy Then Build by Walker Deibel (along with hundreds of business acquisition insights from ChatGPT every day), and I’m more convinced than ever that small business acquisition isn’t just a good strategy—it’s the right one for me. I’ve been cycling through industries, trying to see what fits.

Following the Thread of Curiosity

For a while, I got really excited about a golf cart dealership. It was fun to think about. The market is surprisingly antiquated, the competitors are outdated, and it just felt like a wide open lane. But the more I looked at the structure of the deal, the more I realized that maybe that’s not the right first move. I’d like to revisit it after a smaller success. So I pivoted. And then pivoted again. Every exploration sharpens the edge. More information in my brain translates to better decision-making and future planning.

I even did a personal SWOT analysis to map out who I am as a business operator. Not just what I like, but what I can actually run. What I’m willing to struggle through. What I’ll still care about when it’s not fun. What to avoid completely. What to partner with someone on.

Where the Flashlight Points Now

Now I’m circling around something that feels both exciting and grounded. I’ve found two accounting firms that look promising. I’m preparing to contact the brokers. And what’s pulling me in that direction isn’t just the strength of the businesses—it’s the way they line up with something I’ve already started building.

I’ve got a prototype of a software product for small business owners who use accounting services. It’s early, but the bones are there. And the truth is, I need a real environment to test it. Not just feedback. Friction. I want to see where it breaks. I want to see what it actually helps with. And owning the kind of business I want to serve… that feels like the fastest path to insight.

Running an accounting firm doesn’t intimidate me. I know what I don’t know. But I also know I’m capable of learning fast, building systems, asking good questions, and surrounding myself with people who are better than me at the parts that matter. That gives me enough confidence to take the next step.

Still in the Beginning

So this is where I am. Not at the start line anymore, but still very much at the beginning. I’m running into walls. I’m learning the mechanics. I’m jumping up and down. I’m looking around. I’m mastering the tutorial. I don’t have all the systems. I don’t have a clean schedule. I don’t have a team. But I have momentum. I have direction. I’m making connections. I have clarity on the game I’m playing, even if I can only see one move ahead.

Onwards and upwards!

— Elgin
Founder, New Game