I loved What separates Peter Pans from the pros by @jkglei

Here’s an excerpt:

When the going gets rough in any creative or entrepreneurial project, what we require isn’t reason or rationality, it’s sheer tenacity—commitment to our abilities, commitment to our process, commitment to finishing even in the face of the inevitable setbacks. This is what separates children from the adults, and the Peter Pans from the Pros.

If being grown up means being committed—to a business, a project, a person—then it’s impossible to peak. And the deeper the commitment, the deeper the meaning that can emerge.

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…

How painful is your app?

A couple of weeks ago I was listening to the Tim Ferris podcast. His guest during this episode was Tony Robbins.

A funny side note: I typically listen to podcasts at 2x speed, but I had to slow this episode down, due to the rate at which Tony speaks. Another confession: I’ve always dismissed Tony as a bit of a self help snake oil salesman. I feel bad for judging him. Turns out, he’s actually a pretty amazing individual.

As a result of this interview, I decided to read his book, “Awaken the Giant Within“. I don’t typically read self help books, but I have to say that I really enjoyed this book.

One of the underlying premises in this book is that all of our actions are ultimately driven by either:

  • A) how painful something is, or
  • B) how pleasurable something is

The goal of the book is to get individuals to change their behaviors. That said, it actually got me thinking about how these same principles apply to web and mobile applications. One line in the book stood out in particular:

Link pleasure to any behavior you want someone to repeat.

With this as a filter, it’s interesting to think about which apps you use repeatedly, and why. What have those apps done to create pleasure for you?

If you have an app of your own, it’s also interesting to think about how painful, or pleasurable of an experience you’ve created for your users, especially within your onboarding experience.

Questions to consider

  • When is the last time you did a pain/pleasure audit on your app?
  • What specific things create the most pleasure for your users?
  • How long does it take for a new user to find pleasure in your app?
  • What can you do to reduce the painful elements in your app and in your new user experience (NUX) flow?
  • Are there things you can do to make pleasure more immediate? How might you reduce the time to pleasure (TTP) in your NUX? Could you reduce your NUX TTP from minutes to a matter of seconds?

My Dream Job

I work out of a 10×12 ft room in my backyard.

I wouldn’t change it for anything.

It’s my dream job.

Reflecting on how blessed I am

A couple of things this month have caused me to pause and reflect on how fortunate I feel to be able to work at Automattic.

First, my sister Lisa asked to interview me for her local college paper.

Second, Matt shared that Automattic just celebrated it’s tenth birthday.

Third, was a random thought tweeted by @bryce which turned into an epic thread. Bryce asked:

what message does early stage startup culture send to parents with kids? honest question for those wearing both hats.

This last one stood out the most. Mind you, it’s been a long time since Automattic was considered an early stage startup, but reading through that thread sort of re-confirmed that what we have at Automattic is something that’s unique, and special.

What makes Automattic so unique?

Before Automattic, I had never stayed at a job for more than 2 years. In September, I will have been at Automattic for 5 years.

I thought I might take a few minutes and share a list of the reasons why Automattic continues to shine (at least in my eyes) as an amazing place to work.

Our mission – (and the mission of WordPress core) is to “democratize publishing”. WordPress now hosts 24.1% of all websites on the Internet. That’s a sizable dent, but to be honest, we’ve only just started…
Our values – our company creed and designers creed though short, speak volumes about the types of things we care about.
I get to work with wicked smart people from around the globe.
We believe strongly in open source, which means a great deal to me personally.
We care about our users. No matter which role you’re hired for, your first 3 weeks at Automattic are spend doing support (a happiness rotation as we call it). Teams are also encouraged to continue to do 1 week happiness rotations once a year.
Our company is 100% distributed. We all work from wherever we live. I’m able to work out of a small town in North Carolina vs. needing to relocate to the Bay area just for a job.
I get to work from home. That picture of the shed-looking building at the top of this post is the backyard office I work out of most days. I’m able to work from home, and make my own hours.
Automattic trusts us to get the job done. I don’t clock in or out. If my daughter has a swim practice during the day, I can take her. I don’t have to ask anyone, or clear it with anyone, I just go. No one keeps track of the hours I’m online or off. All that matters is output.
– We’re paid a good salary.
– My family is expecting our third child any day now. As such, I’m about to head on paternity leave. At Automattic we are encouraged to take the time that we need for both Maternity and Paternity. That’s our official policy. No questions asked. I plan to take 4-5 weeks. Some people take 12 weeks. Some people take less. Some people take more. If you’ve been with Automattic for 12 months, your leave is fully paid.
– We have an open vacation policy. If I want time off, I take it. Again, fully paid, no questions asked.
We cover all costs of company travel. We all get together once a year for a Grand meetup. Then throughout the year, each team is encouraged to pick a location and meet together in person for a week. Earlier this month I was in Copenhagen with half of our designers. Last month I was in Atlanta with the other half.
– We have a generous home office setup stipend
– We have a monthly co-working allowance (if working from home is not your thing).
– You can replace your work machine once every 18-24 months.
Devices, hardware, and software are all 100% paid for.
– We have company-sponsored life insurance.
– You can snag a WordPress branded laptop at your four-year anniversary (Yes, the WP logo actually replaces the Apple logo!)
– Every 5 years we’re encouraged to take a 2-3 month paid sabbatical.
– We’re encouraged to swap around to different teams. In the ~5 years I’ve been here I’ve been on 6 different teams. Some people choose to stick to a team a lot longer. It’s almost entirely driven by you.
– We’re encouraged to continue learning by attending conferences, and by purchasing books, and can expense every bit of it.
– We have access to unlimited WP swag, more than most of us know what to do with.
– When you first become an Automattician, you get a free Timbuk2 bag of your choice with a WP logo embroidered on the back.
– Other benefits which are country-specific include health, vision, and dental insurance; matching retirement/pension contributions; childcare vouchers; income protection, and travel insurance.

I’m sure there are more, but I’ll stop there…

Needless to say, I love my job. I feel blessed to work for such a generous and trusting company who’s mission is to legitimately change the world by further democratizing publishing. Each day I’m grateful to work with such brilliant, and amazing co-workers. The way that we run the business (with a focus on long-term impact over short term gains) is something that I admire and respect. We’re not in this to sell out, or to cash out in a quick IPO. We’re in this together to try and make a dent in the world, so far a pretty sizable one. In the end, I can say without a doubt that after 5 years, I’m still really proud to call myself an Automattician, and that Automattic is still my dream job.