A candid look back from someone who nearly quit their startup, didn’t, and has no regrets.
❝The moment you feel most like quitting is almost certainly the bottom.
One year ago I had no clients, no income, no mentor, and no support. Here’s what happened next.
I come from a big family who has a teetering-second-generation, family-run business. I was the first boy in my family to go to & graduate from college and the first to serve in the military. Five years as a paratrooper in the the 82nd Airborne Division, then three years at Penn State to earn two bachelor’s degrees. I lay that stuff out, not to impress anyone, but because context matters. I have always operated at a different pace than most people around me, and for a long time I didn’t fully understand why that felt like a problem. We’ll leave it at that.
After the Army I went back to work at the family business. Twelve years. And then I became a father.
That last part changed everything.
When Mila was born it was like someone ripped a curtain off a window I didn’t know was covered. Everything I had accepted, everything I had normalized, everything I had quietly tolerated, I could see it all clearly for the first time. The environment I was in wasn’t working. It was never going to work. And it was not what I wanted for her.
So, in the way that only slightly unhinged people do, I decided to quit my job and everything that went with it and start a business. Y’know, with no experience, no guidance. Smart.
❝The second I saw the logo, I could see everything it would become.
Before I had even figured out what the business would be or be named, I started the process of doodling a logo. I designed it myself, color schemes, branding boards, the whole thing — but, I swear, the second I saw it, I could see everything it would become. I registered the business, built the website (four or five times), became an official Microsoft Partner, and kept the whole thing completely hidden from everyone around me until Veterans Day of 2023.
When I finally told people I was leaving I got a couple of nervous congratulations, some folks who turned the attention on themselves, and zero real support. That part didn’t surprise me but that didn’t deaden the pain.
What followed was three months of elation followed by four or five months of genuinely dark depression. The kind that entrepreneurship books mention in passing but don’t fully prepare you for. I read constantly. I kept my daughter in mind through the worst of it. After about 8 months of little traction, in November of 2025, I publicly posted that I was effectively giving up. What was surprising was that post got real traction with my network. I won’t pretend that didn’t sting. But the very next morning my first real qualified lead was sitting in my inbox. The kind that actually moves the needle.
I did not give up. I let go. That was a valuable lesson in white knuckling something. And since then, here are a few more chestnuts I uncovered:
On values: Write them yourself. Let the business mirror who you truly are and what you wish for it to stand for because otherwise it’s all an act and people can tell the difference.
On value: Systematically overdeliver. In quality, quantity, convenience — all of it. Systems flip this from being a burden/overachieving to exponential delivery.
On clients: Listen past what they’re saying. The real concern is almost never the feature request on the surface. It’s usually insecurity or frustration wearing a technical hat. When you figure that out, the whole dynamic shifts.
On boundaries: You train people how to treat you whether you mean to or not. If you’re overly accommodating, people will walk all over you, not always because they’re bad people, but because you showed them you’d allow it.
On rate: The person who cares less about the money tends to have an edge. Stand by your value.
Since then things have moved fast. My income has effectively eclipsed what I previously made and in a quarter the time. My client base continues to grow through good work, honest communication, and what I can only describe as an unusual energy in this industry. People are genuinely surprised when their truly enthusiastic & encouraging Microsoft partner actually shows up, does what they say, and cares about the outcome. A weird bar that I’ve set, yet it’s actually my floor.
I work fast. Fast enough that I’m often the one waiting, not because my plate is light but because speed and quality don’t have to be at odds when you actually know what you’re doing.
I’m building out my own Dynamics 365 instance now to support the next phase, preparing for my first hires, scoping office space, designing infrastructure that will scale with the business rather than crack under it. The mobile applications I built from scratch opened my eyes to what’s possible with AI and automation in ways that continue to compound.
❝Your direction beats speed. Every day.
The Valley of Despair is real. That model where you start with energy, fall into the darkest stretch, and either claw your way out or quit, it’s not a metaphor. I lived it. And the moment you feel most like giving up is almost certainly the bottom. Not always, but often enough to matter.
Let go of the white knuckle grip. I held on so tightly for so long trying to force outcomes. The thing that turned the corner came through the moment I stopped strangling it.
Watch who you let in. Some people cannot possibly begin to conceive of building something for themself. They’ll hear your concerns and say just go find a job. Well-meaning, perhaps, but that’s not advice, that’s projection. It says nothing about your path and everything about theirs.
Time is different now. It’s either day or night. I can take Mila to school, be present for what matters, pick the work back up later. The strict schedule was dumb. Time flies now and what’s weird is I actually work essentially nonstop.
Nobody gives a sh*t about you. This is definitely a “results may vary” point to make, because it depends on so many variables. Upbringing. Support network. Relationships. Just, all of it. I hope, folks have a full support network, but I definitely fell into the “near zero support” bucket in every direction. But, there’s a reason it’s called “bootstrapping” because it’s 99% likely to be all on you to execute, baby. No one’s going to save you.
Would I do it again? Yes, without question. Not because it was easy. Not because I had a roadmap. No mentor, no guidance, no template. Just a clear picture of what wasn’t working, a logo I believed in, and a daughter I wasn’t willing to let down.
I’ve always been a business owner, just without a business to run. Again, we’ll leave it at that.
My favorite parts of this past year? That’s easy.
The people: I’ve met some wildly intelligent people in some fascinating industries. People who make me laugh, think, and collaborate like never before. And vice versa. I think it’s just the dynamic I seem to strike between myself & the clients. I get emotionally invested, for better or for worse, in their success. I like to think that helps give me an edge to deliver the kind of quality I would want.
The process: From the beginning of meeting someone on the phone or over a Teams call down to getting the paperwork out of the way so we can get crackin’ on the builds, I love it all. It’s, admittedly, a little fun to hear “wait oh wow, so it’s just you?? How do you do so much?” My answer is always simple– I love this work and I love helping people. And it shows in every step along the way.
The technology: Working with such a diverse client base has taught me a ton about the Microsoft 365 & Dynamics 365 platforms because I’ve applied it in so many different ways to solve so many different issues. This continues to compound as I work with new folks (and my own business) because I can constantly tap into the tech to make life easier for folks while ensuring everything’s organized, well-architectured, and scalable.
The control: I have been completely freed to do with my time and business as I see fit. I want to build out the website? Cool, done. I want to do outreach? Sure thing. Check-ins? Automate it. Comprehensive system enhancements, done in a weekend. Creative copy, dude, it’s also done. All that is to say is I’m a committee of one. No committees, meetings that go nowhere, or talking things to death. Just pure, unadulterated execution and momentum. No slowing things down, Barney-style, for folks that can’t keep up.
The future: As much as I love the control, I also know that this company is not about me. Heck, I’ve watched what happens to companies when they’re built to serve a person’s ego. This business must grow but to get there I must build it to sustain future leaders and entire teams. I have a very clear vision of how this will play out. But I do know my love of spontaneity and blazingly-fast execution will be unlikely to remain at its current level indefinitely, however, I can at least build systems, culture, and stategies that support and encourage it. One thing, you can be dang sure of, is my
values, mission, & vision are the core at everything that Alpyne will do.
Year one is done. I’m proud of it. On to the next.
