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Dark Money is your guide to navigating the post-employment world. The traditional career path is broken in the internet age, and I’m here to help you figure out what to do differently.
I teach you how to turn instability into opportunity by using your skills, experience, and creativity to build sustainable, independent income streams. Whether it’s starting your own business, leveraging tech to work smarter, or learning how to thrive in an economy that’s constantly changing, Dark Money provides practical, no-nonsense guidance to help you succeed.
For those who want to think differently–and act accordingly.
Succession
Professional growth is horrible for romantic relationships.
I went from running a multi-million-dollar business and living on the Las Vegas Strip to living with my mom in Tampa while I studied to get my first software developer job. It paid $75,000–a massive pay cut. Even after I got promoted to $90,000, it was the least I’d ever made. But I could feel it–I was on the right path.
My girlfriend didn’t believe me. She was sick of my shit, and long distance just made it worse. One day she broke up with me, and that was it.
At the time, I didn’t even have space to process it. I was drowning in code, managing deadlines, and trying to get an overdue project shipped. But one Saturday morning, it hit me. I sat there and realized–I was sad.
Saved By The Bell
That’s when I got a text from Anthony, the owner of the company I worked for. He was the one who had taken a chance on me, promoting me and I was proving him right.
Anthony: “What are you doing today?”
Me: “Nothing much, probably code and chill.”
Anthony: “Meet me at my carport at 11. Here’s the address.”
Alrighty then.
The address was in a quiet, older neighborhood. Big trees, big yards, and houses that didn’t look like they were copied and pasted from a blueprint. The house in front was pretty nondescript–until you noticed the huge building behind the house.
Inside, it was a car lover’s dream. About 20 of the cleanest, most expensive classic American cars I’d ever seen. Muscle cars, luxury cars, even a pickup truck from 1910 or something ridiculous like that. I’m not a car guy, but I used to have a canary yellow 1966 Mustang in college, so I could appreciate the collection. And hell yeah, this was impressive.
Anthony clearly loved showing it off. You could see it on his face as I walked around, trying not to drool.
“Pick one,” he said. “We’re going to a car show in Lakeland. If it’s low on gas, I’ll fill it up at my pump outside.”
His own private gas pump. Ok, that’s dope.
Dukes of Hazzard
The car show was exactly what you’d expect. Rows of classic cars, people sweating in lawn chairs under tents, funnel cakes and Diet Coke. Anthony and I walked around, checking out the cars. He’d point out ones he liked, and I’d do the same. He thought about bidding on a few but didn’t.
The auctioneer ended every sale with a loud “Make America Great Again!” chant. We just happened to be standing in front of a vendor selling Confederate flags, pins, and magnets when he turned to me and said:
“Your dad’s running for mayor, right?”
“Yeah,” I said, wondering about where this was going.
“As a Republican?”
“No, he used to be. But it’s a Democrat city, so that’s what he’s running as.”
“Oh,” Anthony said, nodding slowly like he’d just solved a puzzle. “You know, Martin Luther King was a Republican.”
I’d heard this one before. It wasn’t new logic, and I wasn’t in the mood to debate. So, I just nodded and kept walking.
Then Anthony got serious. He started talking about his daughters–how none of them were going to take over his company. He didn’t have a son, and then he looked right at me.
“You’re the first person I’ve met who I think could run the business after me,” he said. “Do you want to?”
I said yes. What else could I say? But deep down, I was skeptical.
Love Island
A few weeks later, Anthony called me on a Thursday night.
“Drive to my beach house on Saturday morning,” he said. “Oh, and bring a date. It’ll be me and my lady.”
Sure, no problem. Except I didn’t have a date.
I’d moved to Tampa to study and spend time with my mom after she retired. My girlfriend had just broken up with me. I didn’t have any friends here, let alone someone I could trust enough to go to my boss’s beach house on the other side of the state.
I started calling everyone I knew.
First, my childhood best friend in Miami. She would’ve been perfect. Nope–she couldn’t that weekend. I worked my way through every homegirl I had on the East Coast. Nothing. Flights didn’t work for anyone in Denver, Vegas, or California.
I felt like a loser. Who can’t get a date for something like this?
Finally, I called my ex. She wasn’t thrilled to hear from me, and I could tell she was about to say no.
“I’m asking as a favor,” I said. “For all the years we were together, you saw how hard I’ve worked and what I gave up for this. This is a huge opportunity for me, and you’re literally the only person who can help.”
She said she’d think about it.
She flew out the next day.
She had some rules: no sleeping together and she didn’t want to talk about us. I wasn’t about to argue. The beach house was more like five beach houses on one massive property. It was so big, it’s like we didn’t even have to sleep in the same zip code.
She was great, we had a wonderful time. It was the type of executive retreat that really gets you to the top.
On the way back to Tampa, we drove my new Audi sports car and stopped by my Ybor City condo. She saw the life I’d built–met my billionaire boss, saw the direction I was going.
For the first time, she believed me. She was proud of me. But she didn’t want me back.
“It was never about money,” she said. “It’s about stability. You’re not a stable person. You never will be.”
She wasn’t wrong. I take risks. And professional risks always seem to come with personal losses.
I can live with that.