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The 4 Pillars of A Location Independent, Family Driven Entrepreneur

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We are deep into our Belize trip, and I can’t believe we have less than two weeks left before our unceremoniously return to the Arizona desert. Earlier in the month, my daughter Reese celebrated her fifth birthday. As I reflected on her life thus far, I noticed a massive increase in my ability to be present as a father. Five years ago, when she was born, you could qualify me as “barely present,” consumed with personal and professional turmoil. Today I have graduated to “highly present,” and our 6-week family adventure is reflective of my evolution.

My increase of presence (and subsequently increase in quality of life) would not be possible without the growth and success of my businesses. From early on I had a vision for location independence which sat at the forefront of much of my decision making. Even today, while Design Pickle supports very traditional business anchors like an office, employees, and payroll, everything we do inside the company can be executed remotely and by others.

Simply put:

Nothing is dependent on one person or one point of weakness.

Today I wanted to share the pillars of my location independence.

As a subtle reminder I am:

  • Married
  • A father of three kids (aged 1, 5 & 11)
  • In my mid-30s with a lot of grown-up bills
  • Running two different businesses and building a third

I highlight my various roles only to illustrate location independence isn’t exclusive for the single 24-year-old fresh off their first read of 4 Hour Workweek or the 37-year-old forever-bachelor life hacking his way to Instagram fame.

Anyone, at any stage of life, can create the circumstances that enable their desired outcomes.

The pillars below are one part tactical and one part mindset. My hope is you’ll be able to leverage these ideas (along with the million other great Medium posts on the topic) and position yourself on a new trajectory.

The first pillar is asynchronous communication.

All business systems and processes do not require me to be available live. I email, meet, video conference, Skype, Slack or whatever other relevant form of communication on my own time. I do not have to be “at work” at a particular time. I do not have office hours to support.

Slack: Bringing back chat like it’s 1997

A business environment that can successfully support asynchronous communication must have a tremendous amount of process and system design in place. People need to know how to do things and what to do without your involvement. A plug goes out to my friend’s company, Trainual, which houses our “user manual”. This tool is critical in supporting our asynchronous business flow. How we do things is out of my head and in the hands of my team.

The second pillar is an online business.

How do you make money? What has to happen for you to get paid?

I’ve found no better way to support a location independent life by making money online. I am still a young entrepreneur. I am actively working towards my big payday, and as a result, I work, a lot. 10–14 hour days are normal during a regular week when I am not traveling or spending time with my family.

With the amount of time I dedicate to my craft, I make sure I am not geographically handcuffed to a certain locale to get paid. I want to enjoy my surroundings and leverage the freedom to work (and live) where I please. Thankfully the world is a very connected place. There is internet access in the far reaches of the globe. As a result, online businesses (businesses in which the entire business cycle can occur digitally) are extremely favorable to someone who wants to see and experience more than their 5-mile suburban bubble.

Doing work online is not enough. There are a lot of businesses that are online in theory, but still require someone to do something face-to-face to get paid. This leads us to…

The third pillar: Recurring and predictable revenue.

There is no way I can spend three days unplugged in Tokyo if I am chasing down my next paycheck. My online business must also generate recurring revenue. The most common online recurring revenue businesses are SaaS companies — software as a service. Netflix, Stripe, and Headspace are some of my favorite SaaS companies. I pay these companies on a monthly basis, auto billed to my credit card until I discontinue their services.

Design Pickle and YesInsights are my two SaaS businesses with recurring revenue. Our clients sign up for our tools and are billed every month, automatically.

C.R.E.A.M., get the money. Dollar dollar billy’all.

Every business day I receive a deposit into my account from the previous day’s sales. I never have to call a client, send a nasty collections letter or track down a check to deposit. Our cash flow is so reliable; I automate all other financial transactions around these deposits. My paycheck, my team’s payroll, vendor bills, you name it, happens without my active involvement.

Automated cash flow = peace of mind to enjoy, work, play, workout, whatever.

Finally, at the risk of sounding cliché,

My final pillar is a clear vision and mission for the work we are doing.

I wake up every morning knowing my team is aligned, no matter what their role or position.

Our vision is to change lives through creativity, and our mission is to be the most helpful creative company in the world.

These two statements drive a global team 24/7/365. I can make quick decisions measured against our vision and mission and trust my leadership, designers and everyone else that drives the business, to do the same.



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