2018 Year In Review


Even though we're nearly two months into 2019, it's never too late for a year-in-review, right?

I’ve been trying to write this article since December. But so much happened in 2018, I found it hard to summarize in a meaningful way.

So, this time, I’m going to go with the tried-and-true good/bad/ugly format…

Last year ended in such a different place than it started, that it’s almost dizzying to look back and try to assess. Still, it’s been an invaluable exercise.

Warning: long-ass article ahead…

The good


We made some big strides as a family last year. We were able to wrangle our finances into something resembling that of actual adults. We moved into a new house that was a better fit for our family of five, and in a much better school district.

My wife (Jessica) and I celebrated 12 years together, though it feels like we’re only now starting to figure out this whole “marriage” thing. Maybe… Adulting is hard. 😉


I quit smoking in October. I’ve never talked much about being a smoker, which is strange given how much I loved it.

I wasn’t one of those people who was always trying to quit or hating on themselves for having such a “nasty habit”. I didn’t think it was nasty at all, and I loved everything about it.

I started somewhere in my mid-20s and it was love at first puff. It never even entered my mind to quit something I enjoyed so much.

Still, somewhere around the end of last summer, I started thinking I should quit. I don’t know where the thought came from, other than the fact that I’m getting old (39), and part of me just wanted to see if I could do it.

So I did.

I haven’t had a cigarette since Oct 15, and I haven’t missed it at all. In fact it’s been quite the opposite. I never realized how much I built my life around smoking. Nor did I realize the effort I put into protecting my routine of sitting outside, working and smoking.

Four months in, I can definitely say my life has improved, not to mention the health benefits.


I also started reading a lot more. Growing up, and even as an adult, I loved to read. But I lost it somewhere along the way of launching businesses, raising kids, and moving all over the country.

Toward the end of the year, I made a conscious effort to get back into reading novels. I missed it. And it’s been great. I even dusted off my old Goodreads profile that had been languishing for years.


Where to even start. 2018 was, by far, the most eventful year of my life, professionally. Here are some of the highlights:

  • I launched a podcast production company, Podcast Royale, and it was a success beyond what I could have hoped. We signed five clients in the first 30 days, and hit $7,500 MRR in the first 90.
  • Despite the success of Podcast Royale (or maybe because of it), I joined a small company called Mission at the end of December (more on that below).
  • I learned a ton about running an actual business (all my previous efforts where variations on freelancing).
  • Side note: MRR is the greatest thing ever, since… ever! I don’t know why it took me so many years of feast-or-famine to finally figure that out.
  • I got way better as an audio engineer, producer, and storyteller.
  • I worked on podcasts with celebrities like Alec Baldwin and Jeffrey Wright.
  • I sold Community Pro Theme.
  • I stopped doing web design all-together (though I’m still doing some design work at Mission.

The bad


There’s a whole list of things around finances and parenting that I wanted to improve, bit didn’t.

I’ve never been the best with managing money, and it’s something at which I need to get significantly better.

Same with parenting. Let’s be honest, I feel like I’m just winging it most of the time. My girls are now 12, 10 and 3, and while I’m doing a pretty good job with the three-year-old, I’ve struggled with my older daughters.

I’m not an expert on the topic of pre-teen girls…. Clearly.

Right now, we do the things I know how to do — we talk a lot, we make things, and we have a lot of fun together. But there’s this whole burgeoning emotional side of things that I feel very ill-equipped to handle.


While I’ve grown a ton in the area of running a real business and managing a team, there’s still so much more I need to learn.

I failed dismally at delegation, and fell short in my efforts to invest in the team at Podcast Royale. These are the things that make great leaders, and I need to learn how to build an effective team, rather than do everything myself when things get crazy.

My creative output also suffered. I think I wrote only two articles and published half-a-dozen episodes of The Gently Mad.

Ironically, now that I’m in the podcast world full-time, I have no time for my own shows.

Once of my big priorities for 2019 is to change that and release more podcast episodes. I really miss doing TGM and have so many other shows I want to get off the ground.

A few things I’ve learned

As I said above, at the very end of the year, I accepted an offer from a California-based media company called Mission.

What, wait?!?

What about Podcast Royale? What about all my ranting about how I would never again engage in traditional employment?

Well, things change. Shit happens, as they say. And here’s where we get to some really important lessons (for me at least).

After leaving Apple in 2017, I spent a lot of time thinking about what I really wanted. It’s been an invaluable exercise. And while most of my adult life has been consumed, in part, with the search for what makes me tick, I truly believe it just takes a certain number of years and experiences to get to an answer that carries any weight.

There are few times in life when everything just clicks, in my experience. I’ve spent most of my 39 years on this planet seeking out those moments, but usually ended up banging my head against a wall, frustrated with failure. Or at least, what felt like failure at the time.

What I didn’t realize, was that everything I was doing while chasing down various interests and careers, was leading me somewhere…

In the moment, I felt a ton of frustration at how disconnected and meaningless everything seemed. But, like a cart full of groceries, you can’t understand how it’s all fitting together until you make the meal.

So, back to Mission.

Mission was one of our first referrals at Podcast Royale. Initially, our conversations were about them coming on board as a client.

But over the course of many months, those conversations turned into an offer to join their team.

At first I thought, “Nope. Been there, done that.” But after several conversations with Mission’s three co-founders (Chad, Steph, and Ian), I started to believe this was an opportunity worth considering.

So then I did the thing I do so well and went into full-on information-gathering overdrive — I talked to people (lots of people), got advice, made lists of pros and cons, what ifs, what if nots, got more advice — to the point that my wife was about ready to kill me.

And despite my loathing for traditional employment, I couldn’t stop thinking about the possibilities at Mission.

And that’s because Mission is no ordinary media company. They (or, “we” at this point) are re-inventing podcasting in a way I’ve never before seen it done. And, in the end, that was something I really to be a part of.

But what sealed the deal for me, was the role itself. For the first time in my life, a company offered me a role that was uniquely suited to me.

All those random experiences and careers came together in a very unique way at Mission, and in the role they wanted me to fill.

It’s been great. Is it possible that all those years weren’t a total waste? And that there existed something for which they could add up to more than the sum or their parts?

The answer, it turns out, is yes.

So, I spent the week of Christmas 2018 signing papers and getting ready for my first day as VP of Ops as Mission.

I’ve always been able to tell almost immediately when something is a mistake. I felt it with all three of my attempts at traditional employment in the last decade. And I’m beyond happy to say that this hasn’t been one of those times.

So, what have I been doing for the last eight weeks?

My role at Mission is to basically run operations and EP all our shows, so the founders can focus on the bigger picture. What exactly does that mean? It means that all my years as a generalist and serial entrepreneur have finally paid off. 😉

Not only do I get to create and refine systems and processes, I get to work with a really great team of people making some really great podcasts.

I get to do both high-level work, and get my hands dirty when I want to. To be completely honest, I didn’t even know a job like this existed.

Turns out, I’m pretty good at operations. The job I’m doing is basically the job of a typical startup COO (which is the role I’m working toward).

But I really have to credit our founders, Chad, Steph and Ian. They did what so few businesses are willing to do — they looked at what I could bring to the table, and built a role around the things I was good at and enjoyed.

Employers, take note: If you want happy, productive employees, try treating them like adults, and helping them find the “lane” where they can become the best versions of themselves.

It’s a novel idea, I know…

All sarcasm aside, this is how you build a business that will make a difference, and stand the test of time. And I’m really excited to be a part of it.

So, what about Podcast Royale?

At this point, Podcast Royale is still my baby, and my retirement plan. We have a great group of clients, and we’re focused on serving them well.

The great thing about building a scalable, productized business, is the freedom it provides to pursue interesting opportunities.

Podcast Royale is a profitable and growing business, but it no longer needs to pay my salary, which gives me a ton of flexibility.

We also now have a very unique opportunity to only work with the very best clients — the ones that are the perfect fit for what we do.

Side note: if you think that might be you, we’d love to hear from you.

Is it insanely busy? Yes. But I don’t think I’d want it any other way.

The team at Podcast Royale is doing a killer job delivering the world-class quality for which we are known, while I get to focus on building the most unique media company I’ve ever encountered.

So far, 2019 is shaping up to be a great year. We just launched a new season of our award-winning podcast, The Story, with hosts like Jeffrey Wright and Alec Baldwin.


Listen to The Story on Apple Podcasts


I’ve spent most of my adult life in pursuit of some sense of meaning and purpose. But everything always seemed so disparate and disconnected.

The takeaway for me is this: sometimes you’re headed somewhere you can’t see or imagine, and the best thing you can do is to keep learning, exploring, and leaning into your strengths.

My first eight weeks at Mission have already been one of the best working experiences of my life. And it could never have happened without all those years of seemingly unrelated projects and experiences.

What I’m trying to say, as cliched as it sounds, is if you’re in one of the dark phases, don’t give up. Just because something failed, doesn’t mean it was a failure.

If nothing else, 2018 taught me that even when things don’t go as planned, you have to stay positive and keep moving forward. The worst thing you can do (which I’ve spent a lot of years doing) is wallowing in depression and self-doubt.


  • Being really busy is tough, but loving the work makes all the difference.
  • Sometimes you don’t know where you’re headed until you get there. And that’s ok.
  • Generalists rule! Don’t give in to the pressure to specialize when you don’t want to.
  • Family is what makes it all worth it.
  • You’ll never be happier than when you’re doing the work you were meant to do.
  • Three-year-old daughters are the best! Seriously, the best!
  • Getting old still sucks.

All in all, I’m super excited for what this year has in store for my family and my work.

P.S. I’d love to hear about your year. Shoot me an email and let me know.

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