Reflecting on 2015…

2015 was an amazing year. I feel extremely grateful. I feel very blessed. I thought I might share a few highlights.

Our family grew

We welcomed baby #3 into our family. Kiora Martin was born healthy, and happy on Jun 26th. She’s an angel. She’s already brought a great deal of joy to our family.


2015 marked my fifth year working at Automattic. Five years is by far the longest I had worked for any single company (I averaged about 2 years per company before Automattic). In almost every way, Automattic was a dream job.

It was with mixed emotions that I decided to leave this past fall. I actually wasn’t even looking for another job at the time. The stars aligned, and it just sort of happened. 🙂

Help Scout

On August 14th I randomly stumbled across this tweet from Nick Francis (the CEO of Help Scout):

I instantly knew that I had to apply. I had been following Help Scout for a couple of years. I knew that they were remote like Automattic. I had been super impressed with their product, with their beliefs, and with the way they ran their company. Everything about Help Scout just sort of resonated with me.

I applied, interviewed, and the rest is history.


I’ve wrestled my entire adult life with “Entrepreneurial Demons”. Perhaps I’ll write about it at length some day, but basically, no matter how happy I was at work, I’ve always been haunted by an all consuming desire to quit my job, and start my own company. In my industry, this almost sounds typical, except:

1) I actually prefer working for someone else.
2) I have no desire to run my own company. 😉

Weird right? For the longest time I felt at conflict with myself. Until this year, I never really took the time to diagnose what the heck was going on…

This June when my daughter was born, I took 5 weeks off of work (Note: Automattic has a ridiculously generous “take whatever time you need” maternity/paternity leave policy – Thanks Automattic!). During this time I was determined to get to the bottom of my entrepreneurial demons.

Through self reflection (basically asking myself a bunch of tough questions), I realized the following:

  • A lot of this entrepreneurial desire was deeply rooted in the fact that my dad was a serial-entrepreneur. All growing up, he habitually started a new company every couple of years (sometimes multiple companies in the same year). As such, the idea of being an entrepreneur was deeply ingrained in me from childhood.
  • Over the years, I’ve acquired many different skills related to starting a company. One false narrative that I had been telling myself was that I was doing myself a disservice by not starting a company. My inner dialogue said, “Heck, I have all of these skills. Why am I letting them go to waste working for someone else?” It was only when I finally asked “Would you actually even be happy running a company” that I discovered the truth.
  • I’m happiest when I’m working for someone else.
  • I had built up this idea that being an entrepreneur was somehow more noble than working for someone else which is simply not true.
  • I love building web apps. Historically, I had associated the act of building web apps with the act of starting a company, as if they were inseparable. I’ve now learned to separate the two.
  • I realized that I don’t have to quit my job to build fun things on the side.
  • I also realized that I can build things on the side (and even charge money for them if I want) without needing to “start a company” (in the traditional silicon valley sense).

These statements all seem obvious to me now. That said, coming up with this list took a great deal of effort on my part.

I’m happy to share that my entrepreneurial demons have been set free!


I no longer have a false burning desire to start my own company. I am at peace with the idea of working for someone else the rest of my life. I’m even excited by it.

As a creative outlet, I launched RoosterMade this year. It’s an experiment of sorts where I’m just building fun little apps with no strings attached. If something excites me, I’ll build it (even if there’s no business model)! I’m still figuring out the details, but I’m excited about the sense of accomplishment and sense of freedom that it’s already brought me.


I built and silently launched a web app called Filln this year. This is where the bulk of my free time has been spent these past 6 months. I didn’t make a big deal out of the launch, because well… I don’t have to. 🙂

Again, I’ll probably write a separate post with details about the project. I’d love to recap some of the ups and downs of launching an entire web app solo.

The service offers a simple way for indie founders to manage their own private freelance network. I built it for myself. It’s a service that I can see myself using more and more moving forward.

Right now it’s free. It’s still not super polished. Feel free to check it out. Take it for a spin. If you do, let me know what you think.

Many, many Thanks

Again, I have so very much to be thankful for.

  • I’m a believer. I don’t talk much about this side of my life, but it’s a huge part of who I am today. I’m extremely grateful to my Heavenly Father, and to Jesus Christ for everything they have blessed me with.
  • I’m so very grateful for my beautiful wife Liesl. We just celebrated our 13th wedding anniversary. Every year my love grows for this amazing woman. She inspires me. I love her dearly.
  • I’m grateful for my oldest daughter Annabelle, for my son Adicus, and for our precious Kiora. Together, they are the source of some of my greatest happiness, frustrations (I’m still learning), and personal growth.
  • I’m grateful to live in America. It no longer feels popular to say that, but America is amazing. I wouldn’t want to live any place else.
  • I’m grateful for everyone at Automattic. For Matt, for everyone on the design and growth teams (I love and miss you all), for the bridge team. You’ll always be family to me. I’m proud of the work we did together. Thanks for all of the great memories this past half decade…
  • I’m grateful to everyone who I’m working with now at Help Scout. What an amazingly talent group. I feel so very privileged to be a part of the team.
  • I’m also grateful to everyone I’ve had the privilege to meet, and associated with at conferences, at church and online.

My heart is full with gratitude. It’s been a fantastic 2015! Thanks for being a part of it!

I can’t wait to see what’s in store this coming year…


3 thoughts on “Reflecting on 2015…

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