The Wall and The Offer

As the calendar turned to October, I began reading (listening to) a new book, "Rich Dad, Poor Dad". Robert Kiyosaki's perspectives further changed my mindset from employee to entrepreneur, accelerating my departure from a corporate, income-based mindset. I think my wife must have been in shock by the end of October, because within two months of leaving my job, I was increasingly adopting a new perspective on money and my career - most of which involved not making a lot of money, at that point. She was patient with me, but I could see signs of me pushing her a little too much. It was important for me to learn how to grow together in this evolution, instead of running so far up ahead and calling back to her to catch up.

Ironically, however, it wasn't my wife who was being pushed too far, it was me. The feverish pace of my new education, the incredible weight of responsibilities I was bearing, the financial pressures, the breakneck schedule - everything was piling up so fast, and I finally broke. The morning of October 25, I woke up sick to my stomach, exhausted, and completely run over. I couldn't eat, and I slept away more than half the day, and I couldn't convince my body to do anything more than roll over in bed. Barely six weeks into being an entrepreneur and here I was, nursing myself through a meltdown day.

I would eventually have a couple more days like this during that first year, pushing my mind and body to the wall, and realizing I needed to ease up. This was a hard lesson for me to learn because I used to think there was no wall, no limit to how much I could push myself. I have always hated resting and sleep, it would always feel so wasteful.  But, as John Piper says, sleep is a daily reminder that we are not God, and I needed that reminder.  Repeatedly.

A week later, I was contacted by a former customer from my telecom job, who asked me to provide some technical consultation on an internal project. Naively, I accepted the opportunity and two weeks later, traveled there to provide the requested consultation, which turned into a job proposal...of substantial proportions. His offer would've exceeded my previous comfortable income, and given me executive powers and an equity stake in his company.

It felt good to be recognized for what I had done at my previous job, and for my skills to be desired. I think we all want that kind of affirmation at our jobs, to feel like we're being rewarded for the things we've done. This was a true test for me, a pivotal decision in my new entrepreneurial mindset: do I go back to working in a corporate job much like my previous job (but with better returns) or continue to set out on my own journey? If I fail at my new venture, will I have wished that I would've accepted his job offer? What about moving my family for the job? Does this betray loyalties to my previous employer, or more importantly to my friends still working there? Can I take the job and still accomplish my entrepreneurial objectives somehow in the long-term?

I told my former customer that I needed some time to sort out priorities and decide my course of action. In the meantime, things were pressure-filling with my startup venture because we were now into our third month of development and the app that we were building was still a horrible mess. We were aiming our business efforts at the beauty industry because the barrier to entry seemed lower, but the consequence was that we were building an app for a market that we knew nothing about - and one that I had no desire to enter. It was a means to an end, but it was feeling more and more out of sorts for me, and I was becoming increasingly worried that this venture I was hanging my hat on was dependent upon an app that was a complete joke. The job decision now seemed more like an ultimatum - if we couldn't correct our current trajectory, and quickly, I had a very attractive parachute. I was enjoying the rush of the free fall, but I couldn't help but begin feeling for that ripcord...

The Cliff

My first weekend after leaving my previous job was weird.  I was restless and didn't know what to do.  It was as if I stood at the top of the Grand Canyon looking down into this fantastic, breathtaking, exhilarating opportunity but I had no idea where to start.  The start itself was too daunting.  As I prepared to head down this cavernous canyon, my attention already was diverted to thoughts of "well maybe I should still be finding other sources of income" or "what's my backup plan?"

Here I was, the new entrepreneur, trying to find my way in this wide open world, and I couldn't help but immediately start reaching for the training wheels.

Finally, Monday morning came and I began my new routine.  Wake up early for prayer, pour a cup of coffee, pour another cup, and then a third.  And...GO.

I felt by this time that I had a lot of catching up to do.  Thankfully, Patrick had invested a lot of time over the summer into building the framework of the company so when I started full-time, our infrastructure was ready.  I felt like I owed Patrick a lot of time to make up for his summer efforts, and although I hadn't been an hourly-waged employee in over a dozen years, somehow that was my mindset early on.  I began counting my weekly hours to be sure I was hitting extraordinary highs.  I felt the pressure to succeed for my family, to make up time for Patrick, to prove right all my believers, and of course try to satisfy my own insatiable inward drive for success.

The first few weeks was a lot of figuring things out...Patrick and I would meet and discuss our business plan, our equity shares, and the multitude of other things that typical business owners face.  We also had two developers working for us part-time (pro bono) but we had never worked together previously so there was all the elements of figuring each other out as well as the part of me now being their boss.

The month of September was a busy month of development for me as I built a basic website for us, built our server backend for the app, and provided direction for our developers.  In the meantime, Patrick and I set out a vision for what the app should be and how to make money with it, and the task became overwhelmingly daunting very quickly.  As we released our very first version to the App Store at the end of September, we had all the signs of rookies entering the marketplace: awful app, no possible hope of monetization, no audience...but boy, we thought we had done something incredible and that everybody should jump on board.

September was truly a lesson in prioritization as much as it was anything.  I had no idea what to focus on - the app (what were we building?), the server (what did it need to have?), working for side income, networking events, maintaining connections through my old job and establishing connections through my new one, figuring out my new family schedule.  I was so splintered in my focus but so utterly busy every moment of the day (well, I suppose the latter has never changed).  As the ineffable Yogi Berra said, "We're lost but we're making good time."  I really had no clue what I was doing, but I was doing a lot of it.

While spending most of my time in front of my laptop screen, I found three escapes that will forever mark the beginning of this journey for me.

First, Keith Urban's new album "Fuse" was released and I listened to it on repeat a hundred times over.  Music has an amazing way of framing our experiences, and this album will forever frame my first month as a budding entrepreneur.

Second, TechCrunch hosted their annual Disrupt conference and I streamed it all week long (in between listening to Keith Urban).  This event opened my eyes to the world of tech in a way I had never considered much (I'd never seen so many geeks huddled in masses together, and yet so many brilliant minds addressing the world's problems in unique and creative ways).

Third, The Lean Startup.  If you're an entrepreneur, especially in tech, and you haven't heard of The Lean Startup or Eric Ries, you shouldn't be reading this blog.  Go. Now.  Patrick recommended we read the book concurrently, and as it turned out, this opened my world to a new degree of education and discipline.  "Reading" books on Amazon's Audible has become my new way of life, whether sitting at Starbucks or driving my car or working from home.  I hardly ever listen to the music or the radio anymore (except when I'm listening to Angels baseball), in favor of listening to a book about money and banking, or venture capital, or startup entrepreneur tips, or real estate investing, or any other number of interesting topics.  I used to be proud when I completed (or nearly completed) a "normal" book or two every year, and now I will finish one or two every month, just by keeping the audio playing.

As I look back on those early days in September, I get a good laugh out of myself in a lot of ways.  But I did happen to make some choices that developed into habits and disciplines that have served me well to this day.

Jump

Preparation

Over the next couple of months, Patrick and I tossed around different ideas of The Big Problem that we aimed to solve in our future business.  In November 2012 on a trip with a few friends, Patrick waited in line at a restaurant far too long for his comfort and the idea was born: solve waiting with an app that shows wait times.

Up until this point I was a Windows guy.  In fact, I always used to chide my Mac friends, and then my conversion slowly began when I got my first iPhone; then an iPad; then an Apple TV.  Finally, the coup de grâce was the sudden realization that if I was going to become an app developer, I needed a MacBook.  Apple just happened to have a great Black Friday deal so I put out the fifteen hundred bucks and began using my spare time in the evenings and weekends to teach myself about app development.

The next nine months was a time of internal realization for me, as I began realizing each of my lasts at my job: my last Christmas party, my last time doing this or that, and so on.  However, I was thinking these thoughts only to myself, because I had not revealed my decision publicly and did not want to tip my hand too early.  Nonetheless, I was deeply-entrenched at the telecom company, so the path to departure was a long path of training people, delegating responsibilities, strategically handling various projects and, ultimately, leading the company to its independence from me.

I took my last vacation in June 2013 and when I returned, I began a countdown towards the day I gave notice to my boss, the company's owner.  It was very emotional for me, as I felt so much excitement over the future, depression over leaving my friends, and apprehension over leaving a paycheck behind and beginning something that promised nothing but the unexpected.  The day came, and I asked my boss for a few minutes.  I began to recall my initial promise of six-months and how it had become twelve years.  I was nervous.  I was shaking.  I was afraid of what he was thinking.  I was glad that I had rehearsed the speech numerous times to myself because I felt almost numb and detached from the moment in his office.

The next six weeks was difficult in all new ways.  I hated how the news broke, and I felt like I betrayed my friends.  I was in a race against the clock to make final preparations for my departure.  I was working sixty- to seventy-hour work weeks out of loyalty and commitment to leave the company in the best possible position without me, but I also felt like I needed to spend time getting ready for my future business.

My last day was Friday, August 30.  I walked out the doors that day at 5pm with no fanfare.  I received no gold watch for my twelve years and there was no party in my honor.  Shoot, I didn't even get a commemorative pen.  I just walked out the doors with my boxes of stuff from my office, packed up my car, and said my goodbyes to some of the closest friends I have ever had.  I took one long last look at my home of twelve years and in that moment, all of my adult life flooded my mind.  And then I drove away, medicating myself on a few Switchfoot songs.  I thought to myself, wallow in your emotions for only a short while David, for tomorrow there's no time for self-pity as your life's greatest challenge awaits.

My Background

Twelve Years of Telecom

Most of us will reach a point at our jobs where we become disheartened or lose interest in what we do.  Some of us will feel that sentiment numerous times throughout the course of our tenures, and for any number of reasons.  I began my career counting on it.  When I was hired at a telecom company at the age of twenty-two, I told the owner that I would commit for no more than six months because I wanted to start my own business, which at the time meant my own computer repair service company.

Ten years later, without ever truly committing myself to starting my own business, my job at the telecom company felt secure and prudent, and it felt like home.  Of course, through my tenure every several months I would feel the rise and fall of sentiments over my job but those feelings were often mitigated with the freedoms that I was given to explore new responsibilities at work and take the company to new heights.  I have a very strong competitive drive in me and I always felt like I needed someone or something to conquer.  The more I was given those freedoms, the more I conquered; the more I conquered, the longer I could suppress the feelings that I wanted to accomplish more in my career.

Beginning in 2010, we hit a stride as a team, and we saw unprecedented successes year over year.  However, it seemed that in the process, freedoms were restricted, trust was unjustly withdrawn and the status quo could no longer be challenged (something that I always thrived at).  I felt dejected and demoted.

The incredible irony during this time was that I was making more money than I probably ever would have imagined when I first started the job.  While it often felt like an obligated bribe just to keep me there, I couldn't deny that it was a successful strategy.  But I wanted more...more challenges, more opportunities, more adventures, more significance.  The money was nice and it provided security for my family but it felt like dirty money.  Why?  Why could I not just be happy with what I had, the amazing friends I worked with, the fun we enjoyed, the camaraderie?  Why could I not just be a "good employee", shutting up and doing what I was told?

Summer 2012

By the summer of 2012, I was completely burnt out.  Eleven years at my job and I now felt mistreated, misunderstood and like the token punching bag whenever the owners had a bad day.  What I didn't realize at the time was how my own paradigms and business mindsets had shifted dramatically the past couple of years.  As I achieved more successes at work, there was an evolution that occurred in my thinking.  Whereas fear and mistrust seemed to be settling in on ownership, determination and ambition was growing inside of me.  I could feel the inevitable creeping in on me but it was so difficult for me to wrap my head around the reality that I was working myself out of a job.  I began to send out warning flags to my closest friends at work but in a way it almost felt like more of a cry for attention than it was truly my intention to get out.  Was I really ready to leave?

As I began considering what other career options I had at the time (which probably were minimal), my longtime friend (and former neighbor) Patrick was bugging me to go into business together with him.  While the idea was appealing, realistically I felt like it would never happen.  I still felt too entrenched at my current job, it was my home.

One evening during this period of time, my wife Heather spoke some words over me that seemed to awaken my soul.  I'm sure if Heather knew then what she knows now, she might've spoken differently to me that night.  However, something in the words she spoke freed me to look beyond my current job, to not be afraid of the unknown, and to consider how I could take Patrick up on his crazy schemes to make me leave the telecom company.  The next day I texted Patrick and asked him if he still wanted to jump.