Dear Family, One Year Later

Tuesday, August 8th, 2011


Nearly one year ago, I addressed my family and friends regarding a career decision that I was about to make. A lot of thought went into my decision and the choice to share some underlying details with them publicly. I put a lot of value in my family and friends' input regarding all big decisions in my life.

Countless hours were spent then wrestling with point and counterpoint offered both internally and interactively while I tried to reign in emotions and remain objective. It was a difficult and stressful process. Naturally, I'm a very analytical thinker and I take pride in making informed, rational decisions. I challenged my pragmatism a year ago by deciding to jump into the relative unknown to see what kinds of opportunities I could make for myself.

Today, I revisit that process as I prepare to make another big decision.

Lessons Learned


Without going into too much detail, for the last year I have spent a good portion of my time and energy as a software craftsman within in a small, seed stage startup. I was the fifth employee hired and the third engineer at the time. As things evolved, we hired a fourth engineer to help fill a devops role. The IT operations requirements of that position meant that our company essentially operated with three excellent engineers creating our application and another great engineer supporting its infrastructure.

As one-third of a team responsible for software design and implementation of a brand new product, I learned a great amount. My passion for developing software which delivers an outstanding user experience meant that I naturally settled into the lead role on all of our client side code. I write naturally settled but I don't mean to underplay the challenge that this responsibility afforded me.

It was the first time I had faced such a large undertaking as the sole resource and the de-facto guru. It was exactly the challenge and opportunity that I had been seeking by making the kind of change that I had made. Arming myself with new tools, new techniques and a new understanding of what it meant to learn by loving what you do, I believe that I met and exceeded expectations set out by my team, myself and our users.


When I approached the startup world last year, I didn't know a whole lot about it. Looking back on it now, it is obvious that I didn't even know what questions to ask of myself or others regarding the opportunity in front of me. Over the course of the last year I've stumbled into or sought out a lot of those questions by living life on the inside of a seed stage startup. I feel like I could have prepared myself better for the decision that I had faced then but sometimes the only way to learn what you don't know is through first hand experience.

What in particular did I learn outside of the technical arena?

I need to see and understand a comprehensive business plan.

Not seeking out, consuming and believing in this document was probably my biggest and most obvious startup rookie move. I totally failed here.

I need to be able to clearly express a product vision to others.

If I can't explain what it is that I'm so passionately working on to my friends, family and peers clearly and concisely then there's a pretty good chance that it will fail. I'm sure that there are exceptions to this but I feel like it's a fairly good indicator for me, at least on a gut check level. To put it another way, I shouldn't need to be in the Empire State Building to finish my elevator pitch.

Branding matters.

Yes, there are probably some examples of successful startups with goofy names, boring colors and lame logos. To me, branding is about attracting great people to use your product and subsequently establishing trust with those users. If I'm not attracted to it myself, I find it very difficult to be the kind of advocate that a young product requires to build a trusting user base.

Marketing matters.

This was a lesson that I expected to learn. However, I think that I had underestimated the powerful combination of brand and marketing in a seed stage startup. There's a great difference between deciding to wait to market an unfinished, feature incomplete product, and not having a product vision and brand that's actually marketable until that's possible.

Compensation matters.

Here's another no-brainer, but I had never experienced a situation like this before. In an inherently volatile environment, when it gets hot and dry in the valley of death, a mirage isn't going to save you. Without a meaningful sense of ownership, or market-rate compensation, my motivation plummeted and a sense of rational discontentment skyrocketed within me.

I attempted to resolve this internally but was rebuffed. That interaction left me even less committed to a product that I didn't believe in when it really needed fanatical devotion and unwavering confidence in its eventual success to have a chance at succeeding.

In Summary

Technically, I learned a lot. Non-technically, I learned a lot. In both areas, I believe that I learned techniques, skills, and lessons that I could not have without this experience. I've grown a tremendous amount over the course of the last twelve months both professionally and personally and that has been ultimately rewarding.

Moving Forward

Reflecting on and summarizing lessons learned is always a great exercise. Exercise is great, but as Kenny Powers once said, "I play real sports… not tryin' to be the best at exercisin'." So, what have I done with all this exercise?

I've taken the last few months to play real sports on a field covering my personal and professional goals, near and long term, with all of my skills in top form. A lot of doors have opened for me as a result of that hard work and execution. At the risk of sounding narcissistic, I was nearly overwhelmed with the many great directions that I could choose to head in.

If last year I jumped into the unknown, this year I'm strolling confidently into a situation where fantastically bright folks have already found a tremendous amount of success. In just a couple of weeks, I'll start my new role as an engineer at Monetate, and I'm absolutely excited!

At Monetate I'll have the opportunity to make a big, positive impact on an already outstanding engineering culture and reach a large, diverse customer base which already trusts the Monetate product and brand. I'll be growing along with the company as it grows and expands its reach and develops more great solutions for satisfied customers.

After meeting with the Monetate leadership I developed a respect for their experiences and qualities as leaders that I can learn from and love working with. I was able to comprehend the company's vision and witness first hand a brand, product and marketing that established, happy customers trust. I will be happily compensated and enjoying some important and[unique benefits while taking pride in my work, growing my skills and developing a tangible sense of ownership. I can't wait to get started!

In Summary, Part Deux

The last year has been an amazing journey for me in many ways. I feel like I've experienced great successes and disappointments and grown from both outcomes. Looking back on myself a year ago, the differences are easy to recognize. As easily recognized are the similarities; I love my family and friends, and I'm excited for the future I'm making for myself, and the opportunities I hope to create for my family.