Reflections on 2 years of StealthX

Two years ago I quit my corporate job and jumped into the great unknown to start StealthX. No safety net, a mortgage, two car payments, two kids, and a wife who believed in me more than I believed in myself.

I shared a short reflection on LinkedIn this week to mark the milestone, and it struck a nerve. A lot of you wrote back, and most are either building something or quietly sitting on the idea of it. So I'm going to do what I did last year and go deeper here, not just on what I've learned, but on how you can actually use it.

This is a brain dump. Two years of battle scars, wins, losses, late nights, and the lessons I wish someone had handed me on day one. Here are 11 of them..

In the spirit of building in public, here's a snapshot of year two. I care more about what these represent than the digits themselves, but it's wild to sit with them.

What holds most people back isn't a lack of ideas or talent, it's fear. Fear of failing, fear of the unknown, fear of not making the bills. I know it intimately, because I held onto my own golden handcuffs for a long time, telling myself it was the responsible thing to do with a mortgage, two car payments, and a family counting on me.

BUT, you can have the nicest prison cell with all kinds of nifty things.. it's still a prison cell. This isn't my first company, and somewhere in the back of my mind I always knew I'd come back to building my own thing. What I didn't fully appreciate is that there's never been a better time to do it than right now. We're in the middle of a complete change in how everything gets built, and that's a pretty cool time to be alive, let alone to start something.

So here's to the crazy ones still sitting on the dream. You genuinely never know until you try.

If there's one thing that's been true these two years, it's that nothing stays the same and nothing ever will. People have come and gone, customers and projects have come and gone, the tools have changed, and even the way we work has been reinvented more than once.

Where we work tells the whole story. I started alone in coffee shops, then moved to my dining room table, then into coworking spaces, then an office, and now we're running out of the CLT Startup House. The only constant is that nothing is constant. The more comfortable you get with that, the more you stop fighting the current and start flowing like water, and the more good things seem to find you.

Almost every great person and great opportunity in StealthX came from a conversation I almost didn't take. I met Kim (my COO) because I said yes to a call with someone, who knew someone, who introduced us. Most of our customers came from warm connections and referrals that never would have happened if I'd stayed heads down grinding.

I call these serendipitous collisions, and the math is simple. The more people you meet, the more ideas you're exposed to, the more conversations you have that don't obviously pay off, the bigger your luck surface area gets, and the more likely something good lands. The flip side of the same coin is giving value away. If you orient everything you do around being useful to other people, and you do it consistently even when there's no visible return, you become known as someone who gives. Then the opportunities start coming to you.

I thought I was using AI before but I wasn't, not really. Over the last year I've completely rebuilt how I work and how the company runs, and now AI is the backbone of basically everything we do. It still surprises me how much is possible once you lean into the discomfort and stop treating it like a novelty. If you want to see exactly what that looks like, I broke down the entire operating system that I run StealthX on.

I've sat with people and helped them connect Claude Code to their actual tools, and watched their brains break a little when they realize they can just talk to all of it and get real work done. Things that were flat out impossible a year ago are routine now. I know a lot of folks are holding back because they think it's overhyped, or a bubble, or not safe, or that it'll hallucinate. There are real things to think through for sure. But in most cases the move is simpler than people want it to be. Pay for the subscription, connect it to your data and your tools, and let it show you what it can do. You'll be shocked.

Work expands to fill whatever time you give it. Give a project three months and it'll take three months. Give it two weeks and you'll be amazed what gets done. We launched the CLT Startup House in about two and a half weeks, not because it was easy, but because I flat out refused to give it more time. We're a small team and control our calendar, so we could move that fast (a little different in bigger orgs) but the principle holds.

A short timeline forces the only question that matters, which is “what actually has to happen?” With the house, that meant accepting the back area wouldn't be renovated in time, and some rooms just wouldn't be finished, and that was okay. We focused on the few spaces that would genuinely land with people and poured our energy there. Early on the website was generic on purpose, just good enough to test whether the idea had legs, and the brand came later once we knew it did. Most people lose months on work that doesn't move the needle. They get lost in the sauce and pour energy into stuff that doesn't matter.

Nobody will ever care about your thing as much as you do. I'll be honest, this one used to frustrate me. I'd be so fired up about an idea that I couldn't sleep, and I couldn't understand why everyone around me wasn't equally obsessed. Then it clicked. It's not their thing. That's not a betrayal or a character flaw, it's just the math of being the founder.

The trap is sliding into resentment, sitting there thinking why isn't anyone else trying as hard as me. The healthier move is to expect the gap and design around it, instead of being surprised by it every single time.

When I ran my first company, everything ran through me. I was breakpoint for all of it, and I never stopped to build systems into the business. It worked right up until it didn't, and it capped how big the thing could get, because I was the ceiling.

This time I've been intentional about not repeating that. I read the books and listened to the podcasts that hammered on how important systems are, and I put real energy into building them early. They're nowhere near perfect, but even the imperfect ones are already paying dividends. If you're building anything, a systematized way of doing the work is one of the highest leverage investments you'll make.

Building a team for someone else's company is one thing. Building it for your own is a different animal. In a corporate job, if someone isn't pulling their weight, there's enough red tape and noise in the system that you can let it ride for a while. In a small company that's your own, there's nowhere to hide. Everyone sees everything, and there's no room for someone who isn't fully bought in.

That raises the bar on every hire. You're not just looking for skill, you're looking for people who are devoted, who challenge themselves, who learn and grow and do the work at a high level without being chased. Finding the right composition of people is genuinely hard, and I feel the weight of getting it right far more now than I ever did inside a big org.

I said this in my year one reflection and it's even truer now. Cash flow is the hardest part of building a company, full stop. Literally everything else is a cake walk. The real stomach drop comes from staring at the cash line, knowing what's sitting in receivables, knowing what's in the bank, and knowing payroll and bills are due on a timeline that just doesn’t line up.

I've done this before, but never at this scale, where I'm the one cutting the big checks and watching the lifeblood of the company move in and out. It's a heavy burden, and nobody warns you how heavy it gets. It can quietly make or break you, and managing your own head around the money matters as much as managing the money itself.

For years I wore never taking time off as a badge of honor. I was proud of it and part of that was that we didn't have the money early on, but a big part was ego, and working myself to the bone felt like proof I was serious. It wasn't smart, and I'm paying for some of it now, literally, with a round of root canals I earned by putting off the dentist for too long.

So here's my nudge to anyone building something. Don't neglect your own health, it's not worth it. I'm now intentional about protecting my nights and weekends, taking real breaks, going on trips with the family, and even just sitting on the porch staring at the trees. That white space on the calendar isn't laziness, it's where the big decisions actually get made.

This last one isn't a new lesson so much as a reminder that keeps getting louder. None of this works alone. The last few months have been really hard, harder than I'll get into here, and without God and the people around me I genuinely don't know how I would have made it through.

Community carried me when I had nothing left to carry myself with. Friends, family, our team, all of it. I've said the word community a lot lately, and I mean it more every time. If you take nothing else from this, take that. Lean on your people when it's heavy, and show up for someone else who's quietly carrying something. It matters more than you know.

I turned 39 last month, I'm two years into building this thing, and I've got plenty of bumps/bruises to show for it. I also absolutely love it, more than I've loved any work I've ever done.

I'm grateful beyond what I can put here. For Jordyn (my wife), who believed in this before there was anything to believe in. For our kids, who put up with the late nights and ask the best questions about the business. For the squad, who carried the company through a season when I couldn't. For the customers who took a chance on us, and for the community that's shown up over and over.

And if you're the one reading this who's been sitting on the idea, holding onto your own golden handcuffs, this is your nudge. Take the jump and just get started. The water's fine, and there's no better time than now.

Do less, but do it better. Move fast and stay human.

Onward & upward 🤘
Drew

A few of the voices that shaped my thinking over the last two years: