Micro Business Aspirations

For the longest time now I’ve been fond of micro businesses.

Most of my friends don’t even know this, but the first real company that I ever started on my own was called SimpleStartup.

It was a web app written in PHP that helped single person companies create a website, charge money for their services, and track finances:

It took me about a decade to realize that I don’t really want to be a start up founder. Up until that point, quitting my job, and launching a startup had always been in the back of my mind. It was an obsession that plagued me.

I find myself in a unique position now, where:

  • I have a job that I love. It’s my dream job really.
  • I have no desire to leave my job any time soon.
  • I have no desire to ever launch my own startup again, but…
  • I do still feel a strong pull to build, and launch micro businesses on the side.

I’ve spent a bunch of time trying to define exactly what I want in a micro business. I figured I’d share that list here.

What I’m looking for:

  • Something I can do while employed (I love my job, I don’t want to quit, I don’t want a startup)
  • To stay independent – never raise money – always own 100%
  • No employees – ever – I don’t want this to ever scale to the point that I’d have to hire anyone
  • No partners – I prefer to work solo on side projects
  • Something I can be excited to wake every single day at 5:00am to work on
  • Where I embrace constraints (out of necessity)
  • A service I wish existed
  • Something around helping designers
  • Simple compelling story
  • Time commitment is no more than 2 hours per day
  • Viral component baked in (preferably)
  • Focused on businesses (not consumers)
  • Strong brand – fun, sticks in your head
  • Strong on the design side
  • Unique business model
  • Long-term play (I’m not worried about making money – especially in the short-term)
  • Super niche
  • Solves a real pain
  • Low maintenance users
  • Low overhead
  • Requires least amount of work per week as possible, with the biggest chance for eventual upside
  • Something I can put on auto-pilot for 2 weeks, or even 2 months (if need be)
  • Minimal feature-set
  • Simple tech
  • To stay forever frugal
  • Authentic (product, and story)
  • My little Utopia
  • Create more value than I capture
  • Where I can stay balanced – Spiritually, Physically, and with Family/Work
  • Principles, People, Product, Profits – always in that order – revenue is just a by product of building something great, never the primary focus

It’s a big list, but I’ve found that it helps me focus my attention. I’m currently using this list to help define what my next micro business will look like.

If you have similar aspirations, I’d love to hear your thoughts.


Finding Balance

Between having a young family, working a full-time job, serving at church, and side projects, my life can feel pretty hectic at times. Finding balance in life is a constant obsession of mine.

My ultimate goal is to live a boring, perfectly scheduled, monotonous life. Turns out, that’s harder than it sounds… 😛

There are 5 areas that I care about maintaining balance in:

This is always fluctuating, but if I dissect each of these areas at any one moment in time, I can get a good feel for where I stand.

So, how would I rate each area on a scale from 0-5 (0 being terrible, 5 being healthy & strong)?

Today, my overall health looks like this:

  • My Family: 3
  • My Physical Health: 1
  • My Spiritual health: 3
  • My Work: 5
  • My Side Projects: 2

There’s lot’s of room for improvement there.

Now what can I do about it?

I’ll do my best to outline what constitutes a 5 in each of these areas.

It’s worth acknowledging that I’m naturally tough on myself when it comes to rating my strengths and weaknesses.

My Family

  • No tech after 5pm. Period. Phone goes in a box. Laptop stays docked
  • Spend 30 min each night cleaning the house
  • Date night weekly
  • Talk with Liesl each night
  • Spend some quality time each day with each of my kids
  • Put kids to bed each night
  • Budget together with Liesl once a month
  • One on one date with each kid once a month

Physical Health

  • Shoot for max of 1750 calories per day
  • 15-30 min working out
  • 40 min walk each day

Spiritual Health

  • Regular nightly & morning prayers
  • Regular morning scripture study
  • Weekly family home evenings
  • Weekly church attendance
  • Regular temple attendance
  • Fasting once a month
  • Serving in my church calling


  • Able to stay above water
  • Able to connect with folks
  • Able to make an impact
  • Able to get a lot done each week
  • Able to set aside time for high level thinking
  • Able to execute on new things
  • Able to keep the brand/product strong

Side Projects

  • Wake early – work on side projects 2 hours each day – 6 days a week
  • Build things I wish existed in the world
  • Don’t stress about side projects needing to make money
  • Find joy in the work

Now it’s your turn

I’d love to hear your take, and learn from you. How do you measure balance in your life? What areas are important to you, and how would you rate yourself in those areas?



It’s so easy to be caught in the trap of keeping up appearances:

  • The way you do your hair each morning
  • The amount of time you spend putting on makeup
  • The cost & style of your clothes/shoes/bag
  • The car you drive
  • The laptop you use at work
  • The house you own
  • The way your house looks (inside/outside)
  • The schools you went to
  • The schools your kids go to
  • How knowledgable you are about any given topic
  • The type of restaurants you eat at (and refuse to eat at)
  • The drinks you choose
  • The people you hang out with (and those you choose not to)
  • The company you work for
  • Your title at work
  • Your previous successes
  • The achievements of your kids
  • How far you ran/swam/rode your bike
  • The amount of time you train each week
  • The length & difficulty of the race you completed
  • The books you’ve read & can quote
  • The activities you participate in

Isn’t it all a bit tiring?

Who is it that you’re trying to impress? When it comes down to it, isn’t this just vanity? Pride? Yet, here you are investing heaps of your time/money/attention into these activities.

One question:

So… What’s this investment given you in return lately?


I’ll Stay Micro, Thanks


We all know the “Silicon Valley” siren call:


  • you quit your job, and start a company, AND
  • you raise money (early & often), AND
  • you prioritize the growth of your company over everything else in your life, AND
  • you can hang onto the reins for 5-12 years…


  • you’ll be rewarded with a Scrooge McDuck sized money vault, AND
  • you’ll ultimately live a fulfilled, happy life!

I used to sip this Kool-aid…

For years:

  • I devoured Hacker News.
  • I obsessed over my startup ideas, and let them consume my every thought.
  • I soaked up every rags-to-riches startup success story that I could get my hands on.

Thankfully, over the past year or two, I’ve started to recognize how silly all of this was, and ultimately how empty these promises are. Over time, I’ve come to realize that:

  • I don’t really have any desire to be rich. I’m grateful for what I have. I live comfortably, and don’t really need anything more.
  • When all is said and done, wealth will not bring you happiness. It just won’t. In fact, it has the exact opposite effect in many cases.
  • Being the CEO of a growth startup sucks. It’s extremely stressful, and it comes with on-going sacrifices (mostly related to time) that I’m just not willing to make.
  • Many people look to entrepreneurship as an escape from the rat race (i.e. a job they hate). It’s not an escape from the rat race, it’s merely a transition to an entirely different rat race – where instead of chasing money, and position, you’re now chasing money, fame, and head count. As the founder of a VC, or angel backed company, the sad reality is that you’ll be even more trapped than back when you were an employee. As an added bonus, your performance will be under a microscope until either you exit, or they kick you out.
  • The joys felt after exiting a startup are short-lived. It’s common knowledge that most businesses are doomed to fail, but let’s say that luck is with you, and you do happen to strike it rich… What next? Now you have a bunch of money, but your business is no longer yours. If you’re acquired, you’ll be stuck as some boring enterprise for another 2-4 years. You’ll long for that rush you felt as a founder, and the emptiness will eat at you.

Unfortunately, this side of the startup founder equation is seldom talked about. Conveniently, you only hear about the unicorns, and the overnight success stories.

It’s been a long time coming, but…

I no longer have any desire to start a startup (Yay!)

Instead, I’ve selected a different path. I chose to stay micro (working on side-projects while still employed).

The formula is simple:

  1. Find a job you adore (where the compensation meets or exceeds your needs)
  2. Keep your job
  3. Build fun projects on the side (limiting yourself to an hour or two each weekday outside of work)

I consider myself extremely blessed to have stumbled into Help Scout. We’re treated well. We’re trusted to do our job. I work with super smart people on a product that thousands of people love. It’s my dream job really, and I plan to stay there for a very long time.

Giving up my startup obsession set me free

I no longer dream of quitting my job. I no longer fantasize about starting my own business. I no longer obsess about business ideas with every passing thought.

I feel more balanced. I feel happier. I feel healthier. And while I do plan to continue tinkering with projects on the side, money is no longer a primary driver. It’s so freeing to work on a side project, and know from the outset that it doesn’t need to turn into a business that will conquer the world! It can just be a fun little project.

Not every technology business needs to be a unicorn. Not every side project needs to be a business. For all of the hype around becoming a startup founder, it’s just not all that it’s cracked up to be.

I for one choose to stay micro.

Image by Will van Wingerden



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…