Why I'll Never Work for Someone Else Again

I’ve spent over 20 years in FinTech. Credit card processing. Payments. The stuff that happens behind the scenes when you swipe your card. If you’ve ever tried to explain what you do for a living and watched someone’s eyes glaze over…welcome to my world.

My first 11 years were with my startup SparkBase, which grew to be the dominant network for processing gift and loyalty card transactions in the US. We were behind the scenes, building a nice business. White-label only. Never a household name. That was fine by me. We exited in 2015 and I moved on.

After that, I went to work for a large ISO in Atlanta. (If you don’t know what an ISO is, don’t worry. Nobody does.) I was there for 2 years trying to get a sales organization to break into being a tech company. I was unsuccessful for a myriad of reasons I won’t get into. I needed a break from payments after that ordeal.

I spent the next 2 years in crypto working on some fascinating projects. That was really a lot of fun. But I got a call one day from a recruiter that wouldn’t take no for an answer, and I got dragged back into FinTech on the card issuing side. We built out a really great network to consolidate cash-back deals and loyalty rewards for consumers. It was fun, but never seemed like “home” for me.

When that company was sold a week before the first case of COVID hit the US, I was already in talks with one of the “Super ISOs” to be their CTO. I really liked the vibe of the team and the leadership had a great reputation. So when the world had recovered enough that it was clear we weren’t going to be living in a post-apocalyptic society, I joined Aurora Payments as their CTO.

The next 16 months were an absolute whirlwind and a lot of fun as we grew Aurora to great heights. My team built some really cool things in that time. We caught the attention of a number of private equity firms, and the time was right to sell. The deal was struck late in the evening on December 31, 2021.

And that’s when everything changed.

The Pattern I Couldn’t See

Here’s what I’ve learned about myself: I’m really good at getting a company to a certain point. The zero-to-one phase. The “all hands on deck, do whatever is needed” phase. Building the plane while flying it. That’s where I thrive.

But when it comes time to go from several hundred million in market cap to billions…I’m not that guy.

The demands that a private equity firm places on you are very different from the scrappy startup mentality that had served me so well. I struggled to find footing in this new world. I’m self-aware enough to know when I’m in over my head…and I was.

For 9 months, I took meeting after meeting and tried to adapt my old way of thinking to this new reality. Weeks of meetings with different departments to make what I thought were small decisions. New management. New swim-lanes. New processes for everything.

I woke up every day with a knot in my stomach.

It turns out, I just wasn’t compatible with the structure anymore. I’m a guy that wants to get shit done…quickly. So the CEO and I had a conversation, and we agreed it was time for me to move on.

The Job Offers Came Pouring In

I put the word out that I’d be looking for a new position, and my phone rang off the hook. I talked to no less than 20 companies in two weeks. Founders looking for someone with my skill set to help take their company to the next level.

Every offer was more of the same. Fix their technology team. Put policies and procedures into place. Grow the company to the exit. Rinse and repeat.

The money was great. But would I be happy? After 20 years of this cycle, I wanted something that made me excited to wake up and get to work every day. Money is one thing, but if you’re unhappy, you’re going to resent going to work. I was sick of that knot in my stomach.

Then I got a call from a friend in the luxury golf space with a completely different idea. He wanted me to join Swag Golf as their Chief Technology and Community Officer.

This felt different. I’d been a collector of high-end putters for years. I’d built several successful communities in that space…CameronCollector.com, PutterTalk.com, GolfOpinions.com (which I sold to GolfWRX). I knew the product. I knew the players. I knew the collectors’ mentality.

The founder was a guy I’d known for 20 years. He wanted to do things differently. “All hands on deck, do whatever is needed.” This is where I belonged.

So I joined. 47 years old, completely switching industries. But not really. It felt like I’d spent 20 years in another industry just preparing for this.

And Then the Pattern Repeated

You can probably guess what happened next.

A private equity firm invested in Swag. New structure. New processes. New swim-lanes.

My entire team was let go.

Same story. Different company. Same ending.

The Lesson I Finally Learned

I’ve been fired. I’ve been acquired out. I’ve watched the thing I built get handed to people who didn’t build it. I’ve had that knot in my stomach more times than I can count.

And every single time, it’s been the same pattern:

Year 1: Joy. Problem-solving. Building. Excitement.

Year 2+: Structure. Meetings. Politics. Misery.

I’m 51 years old now. I’ve finally accepted that this isn’t going to change. I’m not going to suddenly become the guy who thrives in a mature organization with layers of management and quarterly board presentations. That’s not who I am.

So I made a decision: I’m never working for someone else again.

Not because I’m bitter. Not because I think I’m too good for it. Because I finally understand myself well enough to know that the pattern will just repeat.

What I’m Doing Instead

I’m building things I own. Things that can’t be taken away from me. Things that don’t require me to sit in meetings about meetings. Things that are fun problems to solve and then run themselves. THAT is what excites me.

Right now, that’s an AI-powered trading system. Here’s the thing though…I’m actually a really good futures trader. I can make $50K in a month. I’ve done it. The problem isn’t that I can’t trade. The problem is I can’t quit when I’m ahead. Or walk away when I’m not. The grind is intense, and I’m too old for that shit.

So I built a system that codifies what I know how to do…and removes me from the equation. I’d much rather have something that makes $10-20K a month without me touching it than $50K a month that owns my every waking moment.

I’ve also got a few small businesses that can run without constant attention. Build it, validate it, step back.

The goal isn’t to build the next billion-dollar company. I’ve been part of $250M+ in exits. I know what that takes, and I know what it costs.

The goal is freedom.

Where I Am Now

I need to be clear about something: I’m not writing this from rock bottom hoping things get better. I’m writing this from a REALLY good place.

I’ve got no debt. My kids are set up. I have an amazing relationship with my sons, with my partner Dana, and most importantly…with myself. That last one took 36 years of sobriety and a lot of hard lessons to figure out.

The trading bot, the businesses, the “never work for someone else again” thing…it’s not about survival. It’s about building a life where I get to choose what I spend my time on.

Some people call that “fuck you money.” I just call it peace.

And I’m almost there.

The Point

If you’re reading this and you recognize yourself in any of it…the Year 1 high, the Year 2 crash, the pattern you can’t seem to break…maybe the lesson isn’t to find a better company or a better boss or a better industry.

Maybe the lesson is to stop playing a game you were never going to win.

I’m not saying everyone should quit their job and start a business. That’s not the answer for most people.

But for some of us, the answer is to finally accept who we are and build a life that fits…instead of trying to fit into a life that was never designed for us.

That’s what I’m doing now. We’ll see how it goes.

As always, feel free to email me with questions or comments. doug@mrdoug.com