Why Did I Want To Retire By 30?

When I graduated college, I knew one thing for sure: I wasn’t built for the real world.

Not in a “I’m too good for this” way. Just… I didn’t fit. I struggled at part time jobs and summer jobs, not because I couldn’t do the job, but because I wanted to do the job “my way”. I’m sure you’ve heard that story before…

In 2018, I was interning at a Fortune 500 company. Midway through, someone told me I’d “struggle to be employed long term.” I guess they were right. By the time end of summer reviews came up, my boss didn’t even bother to vouch for me, and I was the only one not invited back to the program. In hindsight, it was a great thing. In the moment, it stung.

In 2019, I accepted a full-time offer. Before I even started, they let me go - the company had to downsize. I had nothing to do with this, but, it is a funny ice breaker to share that I was such a bad employee, I was fired before I ever started.

In 2020, I took another job in the Management Consulting world. It paid well. Seemed promising. I left within 9 months after committing to 2 years. I don’t think I was making it much longer anyway, and by then, I knew I was ready to jump into my role as an entrepreneur.

At that point, I had no plan, no money, and no appetite to go chase another job just to collect a paycheck. That same year, I set what might’ve been the most reckless and clarifying goal of my life:

Retire by 30.

The Best, and Worst, Goal I've Set

I really had no right setting a goal like that.

My rent was $650. My monthly budget maybe touched $1,300 if I stretched every dollar. I was living in Chicago with two former coworkers from the job I just quit. My bedroom was 180 square feet - including my bed, desk, and a clothes rack (no closet).

No savings. No fallback. No safety net. But I had a vision.

To me, “retire by 30” didn’t mean mansions or media coverage. It meant freedom. At 30, I wouldn’t have to worry about money. I could do what I wanted, when I wanted, with my time.

It was a goal completely misaligned with the world around me. No one in my family had built a business. None of my friends had either. No one I worked with had done anything like it. It was like saying I’d be a race car driver before getting a license (which, apparently, has happened?)

But that’s exactly what made it the right goal. It forced me to think bigger. To take each day, each dollar, each risk seriously.

And I did, slowly.

Five years later, I’ve more or less done it. I’ve built and sold one business for a large amount, and one business for a much smaller amount. I watch my wife and I’s finances like a hawk. I’ve done well both in public markets and private small business investments.

And now, at 27, I’ve nearly hit the thing I thought was impossible at 22.

Why It Doesn’t Feel Like a Win

Let’s get this out of the way - I’m not sitting on unlimited wealth. There’s no garage full of sports cars or monthly trips abroad. And after tasting a bit of that lifestyle, I’ve realized - I don’t want it. To me, it’s more of an annoyance than anything.

What I’ve found instead is something I didn’t expect - now that I’ve hit the goal, it feels empty.

I’m proud of what I built. But I’m also asking, what now?

Climbing the mountain was exhilarating. But now that I’m here, I’m realizing the summit isn’t the point. The best part was the climb.

Which brings me to the whole point of the newsletter… Be careful with the goals you set, and make sure they’re the right goal to begin with. More thoughts on that below…

Five Lessons I Didn’t See Coming

1. Set a goal, then make it bigger.
“Retire by 30” was the right stretch at the time. It moved me from thinking small to thinking long.

But in hindsight, I wish I had aimed for something more expansive, or admittedly more impactful.

What if the goal had been: build a business, exit, and make every employee a millionaire?

That gets me fired up. It’s intimidating, but possible, and far more meaningful. Openly, at the time I wasn’t thinking of anyone but myself. Jumping ship from a company that paid well made me laser focused on what I needed to do to not only grow the business, but survive.

2. Don’t pick a goal where only you win.
This was my biggest miss.

Retiring early is a solitary victory. It doesn’t create leverage or impact for anyone else.

Looking back, I had more fun when I was giving - whether that meant helping a teammate out, donating to a cause I cared about, or just picking up dinner for someone in the trenches.

And ironically, that giving took me further away from the goal I set.

Funny how that works, isn’t it?

3. The path will change - guaranteed.
Two years ago, I thought I’d run Pneuma forever.

A year ago, I thought I’d become a small business investor.

Now? I’m not sure.

And I’m learning to be okay with that. Seasons shift. Clarity fades. That doesn’t mean you’re lost.

4. Your goals should advance the Kingdom more than yourself.
I haven't written about faith a lot via this newsletter, but it certainly matters here.

When I set my first big goal, it was centered on me.

David’s outcome.

David’s freedom.

But the parts of the journey that meant the most were tied to generosity - supporting my church, backing teams I grew up playing on, helping employees when they needed it.

The next phase won’t be just about building wealth. It’ll be about using what I’ve learned to bring others closer to something greater.

5. The skills are worth more than the milestone.
The number doesn’t matter much.

What matters is the mindset it forced me to build - the discipline, the investing principles, the judgment. I spoke to a young entrepreneur today who’s starting a small business on the side. I told him to worry far less about the “profit” he makes, and more about building the skillset of running a business. Profit truly will come and go, but the skillset of building and growing something is truly a tangible asset.

Like James Clear said: you don’t rise to the level of your goals; you fall to the level of your systems.

I’ve learned to love the systems.

What Comes Next?

I don’t have a perfect answer.

Right now, I’m listening. Reflecting. Letting things sit before I rush into the next build.

What I do know is that the next goal will be less about escape - and more about service.

Working Theories

When I started Pneuma, I spent most of my free time on YouTube. Taking in any and all information I thought might be important. What I engaged with wasn’t overly edited, it typically was a simple video of Sam Ovens or Jack Butcher behind the camera, sharing a mental model or tactic they’ve used in their own business.

Now that the portfolio is growing, I have my hands in quite a few ventures. In the last month alone, I’ve loaned money, raise money, changed around a leadership team, and more. While my instinct is to not openly share, there’s something to be said about sharing what I’m learning so the next generation of entrepreneurs can hopefully learn something - just like I did when I started.

The clip below is what you can come to expect from the Working Theories segment of the newsletter each week.