Reintroduction ●

In October 2011, I was out for a walk with Emily on the Katy Trail in Dallas.

At the time, we'd been dating for a few months in (what we thought was) secret. We worked together at Southwest Airlines and were just about as junior as you could be within the company.

I had graduated from SMU in 2010 with an English Literature major. Outside of the US, my degree would be seen as providing the foundational building blocks for critical thinking, articulate thought, and otherwise. Inside the US, it meant that you would either have to go to law school or become a teacher in order to find a career.

In absence of options, I had gotten into a law school or two — both in the US and UK — as well as a Masters program (or two) in the UK. I didn't have any particular conviction that I was doing the right thing in either direction and sort of drifted toward graduation.

Around that time, to my great surprise, I was offered a spot in Southwest's internship program. It had been on hiatus through the financial crisis, but returned to overwhelming demand from students from around the country. I somehow landed one of those roles and, during my internship, I was offered a full-time position.

Many of my friends had failed to get jobs out of university. The economy remained complicated. So I excitedly accepted and deferred my post-graduate academic options.

I quickly found Southwest Airlines to be a profoundly effective litmus test for different personality types.

The company is storied for its approach to culture and employee wellbeing. And, indeed, they did throw a lot of great parties. And, yes, you'd see the founder roaming the halls smoking cigarettes. But, for me, I couldn't shake the feeling that it was all designed to keep everyone docile and content.

If you were looking for a place to build a long-term, stable, and probably under-paid career, it'd be well suited to purpose. You'd have good benefits, live in the suburbs, and work bizarre hours to avoid traffic. The founder might even kiss you in the mouth at a party. Really good.

But if you had any sense of ambition or desire to fundamentally address core problems, there was little room for that sort of thinking. People had been comfortable for 2-3 decades and weren't going to suffer departures gladly.

For me, I certainly didn't have the wherewithal to have a strong perspective as to how to run an airline differently, nor was I particularly aware of what I wanted to be when I grew up. But I saw people around me being ground down into more compliant versions of themselves.

I found it to be enormously deflating and stifling.

Emily joined in the following Summer's internship class. We began dating and kept it quiet — unsuccessfully, we later learned.

Unlike me, she took to the culture well. She ended up working there for about 13 years. But, even in those early days, I think she understood the nature of my struggle.

So, back to where I started, we went out for a walk in October 2011. And we got talking about the future.

I laid out my frustrations with Southwest and, more broadly, with the strange stigma surrounding the liberal arts in the US.

In doing so, I inadvertently landed on a plan I'd follow:

1. I'd start writing a blog about technology, startups, design, etc.
2. Over time, that blog would build some sort of audience and help me generate some credibility over and above my identity as an English major.
3. With that credibility, I might be able to go work for a technology company or startup.
4. And, if that all went well, I might be able to raise capital and start my own company one day.

In the ensuing days, I spun up a Squarespace account and started writing. I can't remember all of the details, but I remember writing about Netflix's planned off-shoot, Qwikster, as one of my first posts.

To my surprise, it got picked up and amplified by a lot of great people and publications. And, over the coming weeks, Jim Dalrymple gave me the opportunity to write guest posts on The Loop.

I spent a lot of time talking to Jim. I'd call him from the halls of Southwest over lunch breaks. In retrospect, I can't believe how gracious and kind he was. We had no other existing relationship. I was just a 20-something writing overly self-serious articles about technology. He helped me in so many ways.

Over the next few months, my world began to accelerate. I ended up leaving Southwest in April 2012 and went full-time writing, consulting on various projects, and so on.

I punched above my own weight and tried to strike up conversations and friendships with people I admired. And, about a year later, I ended up raising capital to start my first company. (And somewhere along the way Myke approached me with the concept of recording a podcast with him!)

My 5 year plan, of sorts, ended up taking a lot less.

I've talked about it a lot over the years, but it all came down to the philosophy that I needed to write my way into relevance. And one37.net was the means.

Fast forward to now. Emily and I have been married for 9 years. We have a 4 year old son and 6 year old rescue dog. We're living in the UK, after spending 18 years in Dallas. I've built, sold, and lost my own startups and, now, I'm on the other side of the table running M&A and investments for a large US-based retailer. I still technically have a podcast with Myke.

In the next couple of weeks, I'll be running my third marathon. For this one, I'm running on behalf of Children With Cancer. If you look through the donations, you'll see a lot of them come from that indie community that got me started back in 2011. Shawn Blanc, Myke Hurley, Stephen Hackett, Brett Kelly, and so on.

It's a world I owe a lot to. And one that, when I look back on it all, still gives me a smile and so much pride.

So I thought: why not find a way to still participate?

I'm pleased to re-introduce OneThirtySeven.

What should you expect? I have no idea. But I'm excited to have a place to write a little more, share some inspiration, and participate in that indie corner of the web that I hold so dear.