Two weeks ago today I completed a transition that began six months ago to hand off day to day control of my company, appendTo, to my Leadership Team.  You can read the official announcement on the company blog.

I’ve wanted to write a post explaining my motivation and feelings behind this transition and to answer the many questions I’ve gotten.  However, I have struggled to find words until today.  If you have any questions, please leave them in the comments and I’ll do my best to answer them.

Core Purpose

To truly understand appendTo, you must understand our purpose. We were working to build a very different company, one that “Hacked the American Dream“, did things differently and demonstrated a different set of values.  The cornerstone of this goal was embodied in our core purpose, which states:

appendTo exists to equip and serve innovators through technology to positively transform lives.

As Founder & CEO, I took this purpose very seriously and constantly measured myself and the performance of our organization against it.  It was the ideal corporate purpose, inspirational but infinitely unattainable.  Lives can always be positively transformed and this was a purpose that transcended financial gain and extended the goal of “Hacking the Dream” out towards our employees and our clients.

Transformation through Mentorship

Mentorship in many forms became my preferred method for transforming the lives of my leadership team and I worked to model and teach the importance of mentorship to my team so they could replicate it to their direct reports.  This mentorship & growth extended to all facets of what we were doing and became a key component of our success.

We believed that success looked like helping the people we work with every day transform, grow and achieve their version of “Hacking the Dream”.

In late 2013 I came to the realization that in order to fully grow to the next level, my team would need to shoulder more responsibility in our organization.  This presented a dilemma because I had handed off most of the responsibility that was easily delegated to their roles.  I realized that the only way to push my team to grow was to get out of their way.

The fear of separation

At first, this realization produced an immense amount of fear around worst case scenario’s.  Would the company fall over? Would they make a bad decision?

These fears quickly gave way to rationalizations of how necessary I was to the day to day operation of the organization.  This smacked of self-centeredness and quickly gave way to the worst fear of all.

The darkest place before I committed to this path was the fear of letting go and forcing myself out of my own comfort zone.  appendTo was born under my watch and grew from a simple dream to a growing and thriving organization that was the single biggest achievement of my career to that point.  I defined it as the founder and I was now in danger of it defining me.

It was in the darkness of this realization that I realized that I had no other choice but to follow through with a full separation from the organization because the danger of personal creative atrophy was far greater then anything negative that could happen to the organization as a result of me stepping back.

Planning my funeral

Having worked this through, I presented my team with a 6 month plan to hand over everything I’d been hold back as CEO and provide them with full autonomy to run the organization within our corporate structure.  This process began with promoting John Kellar to COO and culminated in the leadership transition that I mentioned earlier in this post.

Death, then freedom

Coming to the realization that the next logical step in the growth of the organization I birthed 4 and a half years ago was killing my role within it was the biggest challenge I’ve faced in my career.  It’s been two weeks and I couldn’t be more impressed with my team and how smooth the transition has gone.  I fully expect them to run into challenges and problems along the way but I have complete confidence in their ability to do so.  They have exceeded my expectations and I couldn’t be more proud.

As for what I’m going to do next? I have a few ideas but I’ll share those later. I do want to say that the feeling of freedom after the intense ownership that develops from running a startup, then leaving it is overwhelming.  It is incredibly satisfying and has filled my entrepreneurial engine with more fuel then I’ve felt in a long time.

Transforming Lives

Our world defines success by an organizations bottom line, growth hacking metrics and how many big accounts you’ve closed.  Going forward, the world will be a better place if we value these things but also measure success by how many lives are transformed and how many dreams we have helped others achieve.  Money and metrics come and go but a changed life endures and makes our world a better place.

I stepped into a fun riff on Twitter where Marc Andreessen published a 15-part tweet-blog on his thoughts on the limits of AI and Robots and their effect on society.

The concept captures my imagination because the media is quick jump to the inevitable end depicted in the Matrix where our machines come alive and Human beings become biological battery power in a post-apocalyptic world.  Once singularity is achieved, humans fall to the dark side of evolution as we slowly welcome the ascension of our new robot overlords.

While that makes for a good Hollywood screenplay, it doesn’t work for two reasons.

First, computers systems will never replace Humans because they lack judgement. Machines can easily distinguish between good and bad options, but they cannot predict taste and style.  Judgement is the result of a lifetime’s experience of constantly making choices, choices where there are multiple positive outcomes. This doesn’t translate to the world of machines where basic rules and logic make up a computers brain.

Second, artificial intelligence falls far short in creativity. They cannot “muster up” the next Mona Lisa or replicate Shakespeare through an digital force of will.  Creativity is the ability to transcend tradition, moving beyond the known into the unknown. If a human programs a machine by transferring its “known” knowledge into instructions, how can the machine ever move beyond it’s own reality into the unknown? The answer? It can’t.

So how much of the world will software eat?

Machines are making a monumental impact in every area of society and as the generations pass by, they will become more and more accepted as a sub-class of steward, albeit more intelligently with each iteration. I believe the impact of this shift won’t be a replacement of what it means to be human, but an amplification of the amount of time we have to focus and spend on the things that truly make us human.

The inevitable end is not the singularity of machines, but the self-actualization of human beings in a beautiful chorus of individual creativity and art.

Optimistic? Maybe. But, that end would be much more interesting then the drab and hopeless background of the Matrix, even if you could learn Kung-Fu in 5 seconds.

Maker Time

November 18, 2013 — Leave a comment

My friend Joe McCann was riffing on a busy meeting schedule this upcoming week. I could relate and shot back a response on Twitter. I’ve fought this for years and thought I’d write a quick blog about it.

One of my favorite habits that I’ve followed from time to time is scheduling what I call “Maker Time”. After starting appendTo four years ago, my day to day work is filled with meetings, writing emails and generally solving problems of all shapes and sizes.

The transition to this role from being a full time software developer left me wishing for the days where I could sit and code all day long without interruptions. I loved software development and I loved the challenge creating something new. Even though a long day of coding could be exhausting if I didn’t keep up my caffeine intake levels, it never felt like work because the act of creating something was motivation to keep going.

Paul Graham wrote an amazing essay that describes the differences between managers and makers and the schedules they each keep. I read this early in my career and was influenced by it quite a bit. However, I always thought managers and makers were mutually exclusive roles.

It’s only as I’ve stepped into more full time management that I’ve discovered that building in “Maker Time” has been foundational to keeping my sanity. Rather than choosing between being a “Maker” OR a “Manager”, I realized I needed to choose both to stay balanced.

Maker and Manager

I’ve solved this by forcing myself to make time each day to “Make” something. Anyone who’s in a management role knows that if you don’t make time for it, it won’t happen. So, I generally schedule my own “Maker Time” for the first two hours of my day. This is when our virtual office is most quiet and I can easily focus.

I view this Maker Time as foundational to my role as a Manager, managing people who make stuff. Putting in the effort to make something every day makes me a better manager and helps keep the priority level high for “Maker Time”.

Maker Time Rules

Along the way I’ve developed a short list of rules to keep myself accountable to my “Maker Time”. I’m not a very religious habit person and I view life more like jazz music then a line dance, but guidelines like these help keep me pointed in the right direction.

  1. Schedule “Maker Time” first to keep it a priority. I generally find 2 hours a day works for me.
  2. Shut out all distractions to keep focused.
  3. Ship something by the end of each session. It could be a blog post, piece of code or an update to a contract template, but create something new and SHIP IT.

That’s it, it’s literally that simple. Sometimes, my maker time feels like the most productive part of my day. Other times I feel like I get nothing done. What matters to me is that I am keeping my creative muscles strong and focused. It is a discipline that I feel makes me a better manager, but to really measure that you’d have to ask my team.

If you’re a manager, do you make time to make something? If you’re a maker, what do you think of a manager who prioritizes “Maker time”?

The Third Way

November 12, 2013 — 2 Comments

Two roads divide, I took neither. In fact I climbed up in the BullDozer and paved a third.

It didn’t start out this way on purpose. In fact I set out to do things the way I was told.

When appendTo launched the first thing we did was hire a COO. Someone that knew how to do business the way business was supposed to be done.

Jonathan & I were the creative team, and we wanted to focus on delivering great customer experiences, not on processes and management.

But when the going got tough, the person we hired to lead the company didn’t believe in the vision of the company. So he left.

Revenues were tight and we were staring at a second business venture sinking. I knew the opportunity to build a business around jQuery was big, but it hadn’t started out the way I planned.

I sought advice from others who had started similar ventures and they pushed me to go get revenue the way all businesses did.

“Hire a Sales Team” they all said to me almost in perfect harmony. I wasn’t a believer. I didn’t feel that salespeople could properly represent us they way it needed to be done.

It was value that they were after. A great product and deliverable. Not someone banging on their door begging for the order. That was the way of yesterday and I knew it was wrong for appendTo

I Took the Third Way

The Third way meant doing what I knew was right even when it wasn’t popular.

Whether it be walking away from money when I know that we aren’t the best fit for a project or refusing to hire a sales team for a company that needed to be built through a network from the inside out.

The third way started out by accident when I couldn’t get on board with the way things have always been done and has morphed into a philosophy that I use for growth hacking.

When two roads divide I don’t take the one less traveled nor do I take the one most traveled. I take the one that makes the most sense which sometimes isn’t a road at all.

Understand, this isn’t about one way being right and one way being wrong.

This is about doing business in a way that reflects what we as an organization believe. Something that I aspire to see from more and more companies in the future.

Begging the question.

When 2 roads divide and neither option makes the most sense for your business, what is your approach? Better yet, what is your third way?

The Choice

November 5, 2013 — 6 Comments

I was nearing a nervous breakdown.  My business, A Mountain Top, was losing steam despite the extra effort I was putting into it in a vain attempt to gain altitude.  I hadn’t taken a day off in almost two years and the recent arrival of my second daughter was making sleep a precious commodity.

It wasn’t working.

On top of all of that, I was unable to shake a growing realization that I was in the wrong business.  My efforts to build a small consulting company around my favorite web technologies wasn’t producing the results I was aiming for and a new opportunity lay at my feet, the opportunity to start the first company solely focused on the little known (at the time) JavaScript library, jQuery.

I was faced with a choice.

It is a familiar choice, one we all face many times in our life.  Do I act, or do I sit.  Do I accept my current reality or summon the courage to change it.  Do I cling to the status quo or do I dare to dream that it could be different.

I had to choose.

Either decision was a choice.  Inaction is a choice but as you get to know me better, you’ll see that I’m a sucker for adventure.  I took two weeks off over the holidays to clear my head, re-engage with my family and allow myself the mental space to make a decision that I knew I could stand upon.

I chose to jump.

Taking this leap was one of the biggest choices I’ve personally had to make in my life.  However, I am eternally grateful that the foundation of appendTo and that my current circumstances are based off of a conscious choice.  Knowing that fate has not dealt me a short hand nor am I the victim of external forces such as market conditions or bad customers is empowering; it helps me to temper the inevitable peaks and valleys of being an entrepreneur.

We all face choices every day. Choosing to make an intentional choice takes courage, but makes all the difference.  What are you going to choose?