Trials & Failures: Revisiting the Need for Risk

I’m a 9th grade dropout. Lived in a trailer park. Worked construction, manual labor, whatever paid the bills through my 20s. But the whole time I was building websites on the side. Running two vBulletin forums. Had a part-time gig with fastlaptoprepair.com. Just fiddling with computers because that’s what I liked doing.

It wasn’t until 2009 when a friend said something I’d never thought about. He just pointed out the obvious.

“Mike, you know you could do this for a living, right? Building websites?”

I’d never considered it. Not once. It was just a thing I did. But he was right.

The first website I built was for his boss at Zero Point, a company that sold tactical gear to law enforcement and military. 2010. That was the start of my first freelancing career. I named my company MK3Y, LLC.

The First Try

I freelanced for about three and a half years. Moderately successful. I was good at networking - hosted a WordCamp locally in Hampton Roads, started a Social Media Club. Connections are what bring you business, and word of mouth was good back then for a freelance web dev. I built my early career on WordPress like a lot of other developers. But I had no systems. Couldn’t keep clients. Couldn’t scale. I was a guy who could build things and couldn’t run a business.

I was blogging a lot back then too. If you dig into the old archives on this site, you can see it - Tim Ferriss, taking risks, living a kickass lifestyle, action cures fear. I was writing about success while I was figuring out my own. The whole blog was me thinking out loud on that early entrepreneurial journey. And that struggle was starting to weigh on me.

In January 2012 I set myself a goal. I’ve told very few people this.

I wanted to make $65,000 that year. It was more money than I’d made to date. I arrived at the number because $5,500 a month felt like a good target. I’d have ups and downs, and I figured out how many sites I’d need to build each month to get there. Even though it was an odd number, not clean or even, it felt realistic. I wrote it on the whiteboard in my office in big red letters.

In March I got a referral from a friend. I had helped his dad with his WordPress website a handful of times.

But this job was a touch harder than previous jobs I’d tackled. I almost quit the project. It was just slightly outside my comfort zone and skill level. But I know that stretching yourself is how you grow, so I pushed through.

I finished the job. Got paid. And the client offered me a full-time salaried position on the spot.

I still remember it. He said, “I want to make you an offer.” Wrote it on a piece of folded up paper and handed it to me. Told me to think about it and don’t answer just yet.

He had written $65,100.

I froze. That was my exact number. The one on my whiteboard. Plus a hundred bucks.

When I got home I showed my wife. She said, “TAKE it.”

I took it as a sign from God. And wrote my response accepting the offer that evening.

The Ten-Year Stay

I grew a ton at that job. My skill set exploded. It was a small agency shop, about seven of us, and the vibes were great. Steeven - French guy, spelled his name weird which always messed with spell checkers - he was the one who hired me. Set the initial vibe of the shop. The kind of boss you want to work for.

Around year three the entrepreneurial itch started. I wanted to go somewhere else, build something of my own again.

But here’s what happened. The tiny voice. The one that says you’re a failure. The one that says this is the first real job you’ve ever had with real money and this is safe. STAY.

And stay I did. For ten years.

There’s a second reason I stayed, and it’s a good one. In 2014 the company was struggling and I used the opportunity to be the first person to go remote. That let me and my wife pursue our first dream - traveling full time in our Airstream across the country. Two years on the road, 2015 to 2016, before we finally settled down in Idaho. I’ve been remote since 2014.

But Steeven left in 2019, and that’s when things turned toxic. The company had merged with another agency, and the new leadership had different ideas. The culture died. Everyone started quitting. I hadn’t received a raise since 2018. In 2020 most of my coworkers were furloughed through COVID and into early 2021. I was considered essential and kept working. That was odd. Watching everyone get sent home while I kept going.

They burned me out. I stayed too long because of fear.

The real irony? The company got acquired in 2023, a year after I quit. The whole US team got laid off and replaced. I was going to be jobless no matter what. The safety I was so scared to leave was an illusion the entire time.

The Rage Quit

One day in August 2022 a coworker - who will remain unnamed, but who had personality issues and couldn’t get along with anyone - left me an insulting message in Slack.

I got up that morning, saw that message, and was just so mad.

Not that it was insulting. I was mad at myself. I’m a grown man being insulted because I am too scared to do something else. Too scared to see my own self-worth.

I rage quit in that moment. Wrote the whole company and told them I quit. In all caps. Every word of it.

Not professional. But man, it felt great.

The Detour

When we moved to Idaho in 2016 I was listening to Bigger Pockets. My retirement plan was to buy rentals and get into real estate investing. We bought one rental and our house, but we never really got into it the way I dreamed about.

So after quitting, I went full bore. Wholesaling, house flipping, whatever it takes. Networking my ass off.

We did our first flip. It went well - made $75,000. Learned a lot about investing and did more.

But it turns out real estate is HARD. It’s a TON more hustle than I’d ever done before. And the income isn’t steady or predictable like many gurus claim. The fact of the matter is, it’s a real grind and most are not successful.

But through it all something kept coming up. As I networked and connected, people would ask what I used to do. What skills I had. And there were opportunities to make content, build a website or build an app. As I networked on X in particular, I realized something.

Hell, I still love tech.

Around this time I started playing with AI a lot, too. When we got our first flip under contract in October 2023, I also picked up a side gig - being a white-label dev for TechGuys.

It was TechGuys that made me realize something important. I still love this. I just was burned out from the last job. They made me hate what I did. The work itself never stopped being the thing I wanted to do.

The flip and real estate investing is its own story. A much longer one. But what I learned was that dream and vision was really just that. A dream. It wasn’t me. It never really was.

The idea of making a ton of money being a successful real estate investor, that seemed cool. Hell who doesn’t want to have a ton of money? But what was involved to be that person, that was not who I am. Not my passion.

Then my mother passed away. Winter 2023.

Grief does something to you. It strips away the noise. And what it stripped away for me was the real estate dream. I realized that wasn’t for me. Not just that I didn’t want the hustle - I didn’t want the life. Real estate ties you to a place. You can sort of do it from all over, but not really. Not the way I wanted to live.

But writing code during that time - that was comforting. I could just zero in and focus on tasks. Build something. Make it work. The rest of the world could be falling apart and I could sit down at a keyboard and make a thing function. That’s always been there for me.

And I could write code from anywhere. My family was able to travel a bit more during that time, and that made me realize something else. Tech is just part of our lives, everywhere. I love building. Making apps, exploring AI. It travels with you. It’s a natural fit for the life I actually want.

The real estate dream faded. And I remembered what I actually wanted to do.

Back to the Start

Here’s the thing. Before I quit, I had done a little freelancing on the side on Fiverr in 2019 and a few times in 2020. And I had started 1337 Hero, LLC. I kept that LLC going this whole time - through the rage quit, through the real estate detour, through all of it.

So when I finally decided to step back into it in late 2024, the company and brand were there. Ready to grow and expand. I wasn’t starting from zero. I was picking something back up that I’d never fully put down.

I went from building websites because I liked it, to taking a salary job because it felt safe, to rage-quitting because I was scared, to chasing a completely different dream because I thought that was the answer, to landing right back where I started.

Building things. Only this time I know what I’m doing.

I wrote about action curing fear back in 2010. I still believe that. But what I didn’t know then was how many times you’d have to learn the same lesson. How many times fear would dress up as something else - as comfort, as loyalty, as “the safe choice.” How many times the thing you’re running toward is the thing you already had.

The dropout who built websites because he liked it. That’s still the guy in the chair. He just has better hardware now.

I write about this stuff on X @1337hero.