Fifteen years.

That's how long I spent in the tech industry before I bought a hair salon.

I didn't start out planning to own a business. I started out writing code. Then I moved into design, because I realized I cared more about how people experienced a product than how the code behind it worked. Then I moved into management, because I figured out I was better at helping a team of designers do great work than I was at doing all of it myself. Then I moved into leading organizations, because I kept getting promoted into bigger rooms with bigger problems.

On paper, this was a career going exactly the way it was supposed to go. Each step was a logical next step. More responsibility, more money, more influence.

But somewhere along the way, I noticed something that bothered me. The higher I got, the further I drifted from anything that felt real. I was spending more and more of my time on things that had less and less to do with ground truth reality. I'd spend a week debating the structure of a presentation deck to frame some abstract product concept for an executive, and I'd look up and think: when was the last time I actually built something that a real person used? I was in bigger rooms, but the work felt smaller.

After five years at my company, I was given the opportunity to take a month-long sabbatical. I thought I'd use it to recharge and come back refreshed. Instead, it cracked something open.

I traveled. I worked on projects around my house. I made some decisions about my health that I'd been putting off. And I started doing something I hadn't done in years: paying attention to the things that actually made me feel useful. Almost none of them had anything to do with tech. They were happening in my community. Conversations with neighbors. Supporting local businesses. Being in places where people knew my name and I knew theirs.

I also started looking at how I was investing my money. I was heavily in the stock market, traditional index funds, the standard playbook. I owned real estate that I lived in. I'd tried renting out a former home and didn't love the experience. I started wondering: what if I thought about investing differently? Not just where to park money, but how to put it to work in a way that I actually controlled?

That question led me down a rabbit hole. I read "The Psychology of Money," which reframed how I thought about risk and independence. I'd already been through books like "The Simple Path to Wealth" and "The World's Simplest Stock Picking Strategy," but those were about traditional investing. I started looking into small business acquisition as an entirely different kind of investment. One where you don't just own a piece of paper. You own the thing.

I listened to podcasts like "How I Built This," which covers much bigger businesses than what I was considering, but the founder mentality resonated. I started approaching the idea of buying a business the same way I'd approach any design problem: define the constraints, understand the requirements, research the landscape.

Then I did something that changed everything. I flew to California, where I used to live, and attended a weekend-long business buying course taught by acquisition experts. Not a webinar. Not a YouTube playlist. An in-person, intensive weekend with people who had actually done deals. During that weekend, I was able to identify the type of business I wanted to pursue: a hair and nail salon. I started evaluating my first four on-market deals before I even flew home.

Around the same time, AI was reshaping the tech industry I'd spent my career in. I watched layoffs hit designers, engineers, and product managers I respected. People who were good at their jobs. People who did everything right. And it hasn't stopped. As I write this, another 8,000 people in tech just lost their jobs today. This one hit close to home. It keeps hitting close to home. And every round reinforces the same lesson: "doing everything right" inside someone else's company doesn't protect you from anything. You're still one restructuring away from starting over. That reality added fuel to what was already burning.

I started my search in earnest in August of 2024. Over the next nine months, I reviewed 32 deals. Hair salons, nail salons, barber shops...all variations of salons. I'll deep dive on why salons in another issue. I learned to read listings, spot red flags, and ask the questions that sellers don't want to answer. Most of what I found was overpriced, misrepresented, or both. But every deal I evaluated made me sharper.

When I finally found a hair salon in Virginia that had real potential, I had zero beauty industry experience. I didn't know how to cut hair, manage a salon floor, or price a balayage. I also didn't know what a balayage was or how to pronounce it. But I knew how to read a P&L, evaluate a team, build systems, and grow something. I figured: the salon already has the people who know hair. It needs someone who knows how to run a business.

That bet worked. We grew nearly 200% in the first year. I just finished my first full year of ownership this month.

But I want to be honest: it wasn't what I expected. Within the first week, I discovered things about the business that no walkthrough had revealed. Deferred maintenance, equipment issues, systems that needed to be rebuilt from scratch. I found myself scrubbing floors on my hands and knees at 10 PM and fishing wires through dusty ceiling panels to get the security system working. Business ownership is not passive income. If anything, it's the most active thing I've ever done. But the fulfillment that comes from it, especially in a local business where you see the impact of your work every single day, is something I never experienced in fifteen years in tech.

Here's what I want you to take away from this if you're someone who's been building skills inside someone else's company for years: those skills are yours. You built them. And they're worth more than whatever your salary says, because they can be applied to something you own. Systems thinking is systems thinking. People management is people management. Understanding how customers interact with your business is valuable whether you're designing an app or running a salon.

Buying a business instead of starting one meant I didn't have to build from zero. I inherited customers, cash flow, employees, and systems. My job was to make all of it better. That's not a totally different skill set from what I was already doing in tech. It's the same skill set pointed at something I actually own.

I'm not going to tell you this was easy or that everybody should do it. It was scary. My wife Chelsea and I had a lot of long conversations about what this meant for our family before we committed. There were moments during the process where I questioned everything. And there are real risks I'll get into in future issues. But the core decision, trading a career built on someone else's foundation for a business built on my own, is the best decision we've ever made.

This newsletter is about everything I've learned on the other side of that decision. And I'm going to be honest about every part of it: what worked, what didn't, what I'd do differently, and what I wish someone had told me before I started.

Welcome to Hundred Dollar Empire.

Michael

I’m building out a suite of products and services to help people like you consider buying or starting then scaling a local small business. If you’re interested in learning more, let me know.