2015 Year in Review

I can’t believe that today is the last day of January in the year 2016! It’s been a whirlwind of activity and typically I’ve written this type of post within the first week of the new year (as you can see here for 2012, 2013, and 2014).

And as I sit here I just can’t seem to figure out where to start; all I know is that I feel compelled to get this post out of the door before we hit February. Where does one start when they don’t know where to start?

A Year of Change

2015 will go down as one of the most challenging years of my life and one that I couldn’t have possibly planned in any way, shape, or form.

As I review my goals for 2015 I find myself chuckling a bit. Here they are in a short list:

  1. Homeschooling my kids
  2. Getting debt free
  3. Traveling more with the family
  4. Grow and retain (related to my startup)
  5. Zero new projects
  6. Spiritual growth

I suppose I’ll start there as I review my goals and give an update of how I totally knocked them out of the park (or wildly missed the target).


Our hope when we first started homeschooling our oldest was to get our bearings on this brave new world of doing education. I’ll admit, this past year was a total mess and we were all over the place with our strategies and methods of approach.

In this way, we succeeded as we began to understand that homeschooling is really just figuring out how to create a new family dynamic, one that is as challenging as anything else. We succeeded in surviving our first calendar year with only a few bumps and bruises.

But I had hopes that we’d be able to “codify” our approach into some systematic form of engagement that would be infinitely scalable and easily manageable and maintainable. I’m not sure what I was smoking but that’s just not how it’s done in principle and not how my wife and I operate on the daily.

And it was still too early for us to know the “how” – what we were sure about was the “why” and the first year was all about confirming our original intent and resolve. I think we accomplished just that.

I will say that homeschooling our oldest in her first year has grown my wife and I as a couple as it’s forced us to have some very tough but healthy conversations about how we want to raise our children and the avenues by and through which we’d do those things and allocations of time that we’d reasonable allow.

It forced us to return to our base motives and we were forced to encounter our core philosophies around learning and education. We realized that we were very different but that these differences could co-exist in fluid harmony. That doesn’t mean that it was easy though.

Getting Debt Free

When I wrote this goal for 2015 I wasn’t entirely sure how I’d pay back the debts that I owed for some previous ventures but I just knew that I’d be able to work through them.

Thankfully, we’ve been able to clear through nearly all of it and in a few months (after I do my 2015 taxes) we should be entirely done with them. A bit more information on this later on in the post…

Travel More with Family

Hah. I read this and I literally laughed out loud:

It’s not that I want to travel any more than I did this past year as I traveled way too much for my current obligations. Rather, I want to travel more with my family. It’s as simple as that.

Our original goal was that we’d all travel as a family while I was doing my business travel. In other words, my family would “tag along” as I continued to grow and expand my startup. A two-for-one type of deal.

Well, we did end up traveling a ton as a family, just not with that company and not for those reasons. So, I got this right but couldn’t have possibly guessed that we’d be accomplishing this goal in the way that we did.

I ended up leaving the startup and then first planning on moving back to Austin and wrote about it not once, but twice (the second one was a repots from my indie dev blog at the time). Needless to say, we didn’t end up in Austin but rather San Francisco and we did a ton of traveling last year.

So, we knocked this one out but didn’t do it in a way that we were originally planning. I love how that happens.


The original crew.

Grow & Retain…?

The next goal for 2015 was specifically about The Iron Yard, my last company that I helped build out. I remember like it was yesterday and I can still remember the first time that I met Peter (via Twitter) and when he first asked me to be a mentor on the brand new accelerator (this was back in May of 2012!).

We had grown a ton in 2014 and were ready to kick it up a notch in 2015 and continue to dominate the EdTech market. We had already secured the top spot as the largest code school in the US and was looking at bringing on a new round of staff, offices, and venture capital.

What I didn’t know at the time was that in a few more months I’d find an opportunity to exit from the startup as we decided to sell it to a Fortune 300. I shared a few thoughts here on that already and TIY wrote an unnecessary post about my participation in the business.

I left on the best of terms possible and still count them as dear friends – I miss them all greatly. I wrote this in my 2015 Goals post:

I want to work for a company that creates a healthy environment for the staff to grow personally and professionally and I’m responsible to help create that type of environment – a place that serves them incredibly well for a period and season of their professional lives.

And it was true – this has been an unyielding passion of mine for many, many years and my journey in 2015 would force me come face to face with the reality that most organizations do not fundamentally care about the health of their staff (and consequently the health of the business).

The Iron Yard was different but it was time to move on and so I totally missed this goal by a long-shot but I was ready for new and exciting adventures (and much later I’d decide to focus all of my efforts in this particular area of organizational health).

Zero New Projects

LOL. I had promised myself to fully focus on building The Iron Yard out and continue to work on my very small indie project Desk and say “NO” to any new opportunities or inclinations that I typically had. I was set on this and very happy to focus my efforts.

Well, I failed to adhere to this one but it was for the better. I started a few new projects, continued to build out Desk, and joined a few new companies in 2015 (I have all of the W2’s to prove it). Eh.

On Spiritual Things

My faith is core to who I am and guides my decision making in much of life. Did I accomplish my goal of walking more closely with Christ? I’m not entirely sure but one thing I can be sure of is that God hasn’t quit on me and I didn’t quit on him (although I definitely had my moments…).

If faith is a fundamental part of life than it doesn’t always have to be explicitly and viscerally appreciated – very much like breathing, we do not consciously think about breathing in every single breath that we take, but in the moments where you remember that you are, well, you’re glad for it.

I will say that, though, that moving to San Francisco has been an incredible part of my journey and the steps that I’ve taken forward have been the right ones.

So, What the Heck Happened in 2015?

Oh, ugh, I’m not entirely sure. All I know is that I started 2015 with what I felt like was a ton of clarity and ended the year completely upside down.

I didn’t know that 2015 would be a year of extreme testing, of exercising courage in the face of doubt and ambiguity, and an opportunity to practice the fine art of getting up when you get the shit knocked out of you. I would love to say that I was in perfect form every single time but then I’d be lying.


I’ve come back to this quote via Anaïs Nin a few times this year:

Life shrinks or expands in proportion to one’s courage.

If anything, my life has most certainly expanded but I’m not sure it’s been based on my courage. I’d like to think so but instead I think my wife has been the one with the real courage while she’s watched her husband flail and flounder through 2015. So if I were to make any edits it would be more like this:

Life shrinks or expands in proportion to your wife’s courage.

She’s been there the entire time, watching, waiting, praying, acting, interceding, and counseling me through the ups, the downs, and the brutal side-to-sides. I am so grateful to have a partner like her.

Okay, so, I’ll admit it – this post is getting old and I have other stuff to do with my weekend, so, here are some hits as I scan through my old blog posts from 2015…:

  • We started homeschooling our oldest.
  • I left an amazing company, The Iron Yard.
  • We thought we’d move to Austin. Instead we moved to San Francisco.
  • We traveled a lot, visited family, vacationed in Hawaii.
  • I joined one startup that lasted 57 days, then another for 40 days, and then tried one more time which lasted 25 days (5 full business days, to be exact).
  • I became an Entrepreneur in Residence and advisor at a VC firm.
  • My indie app, Desk, won Best Apps of the Year again. What.
  • I tried vlogging. I said I’d do it for a year and I quit after 10 days. Felt like a complete loser.
  • Spoke at the White House.
  • Closed down two blogs. Consolidated indie projects. Started blogging more on Medium.
  • Spoke at an Indie Conference, my only major speaking event of the year.
  • Celebrated 10 years of marriage with my spouse. My oldest turned 9, my youngest would turn 5 shortly after.
  • I quit social media. Then I came back. Then I quit again. And then I came back.

And… the hits keep on coming. At some point I may return to this blog post and finish it up… but if I don’t hit the “Publish” button here then I never will because, at this point, I hate this post. Ugh, almost 2,000 words?! Blargh.