Well, it’s been a little while since I last updated my progress at a small seed round startup in the social CRM space.   I remember when the opportunity to explore the unknown of a startup presented itself, and the uncertainty being a very difficult thing to overcome.  I made lists and talked to pretty much everyone who I respected in my field, my family and came to the conclusion that you don’t get ahead in life by not taking risks...  So I jumped on it, and as you saw from my last post on this topic, it was immediately exciting and rewarding.

I learned a lot of things both in engineering and business, which I will detail later.  I also learned an awful lot about myself as a person. I guess I was naturally coming to a keyframe in my life and began to ask myself, “Is this what I really want to be doing?”.  And with this opportunity, I really started to see my career as the palette that it was...

I got to know myself

This is not unique to working in a startup, this goes for anyone who’s WORKING.  I feel that the experience taught me a lot about what I enjoy in the field of computing in general.  Prior to my latest position as Devops, I had done a bit of nearly everything Internet related with some success, but was looking to make a change and become more specialized.  I felt like I could never really grok some of the stuff I was doing at the gosu level, mostly because I was constantly jumping from stack-to-stack and end-to-end on each new project (which is a good skill for a consultant, actually).  This role gave me, and really for the first time, an area of specialization.  To those who don’t know, specialization is important as you get deeper into your career, both financially and from personal enrichment standpoint.  It’s important to find the things you like in your field and go after those things.

As the Devops specialist, I found myself really enjoying when things ran smoothly, because that meant everyone was happy.  However, I found monitoring systems to be stressful, and I would sometimes be checking my phone when I shouldn’t have been, however irrational that may sound.  I also didn’t enjoy dealing with intermittent problems with Amazon (EBS related outages, etc), being ready to fix something out of your control or monitor safety nets you put in place can give you a heightened sense of anxiety.

In the end, I learned that I enjoyed being specialized, but just not in the ops role.  I found it to be too stressful, and missed the creativity that working up higher in the stack afforded me.  I missed working with clients and bringing the thing that they most care about (the application) to life.  So my next opportunity would have to be one that was working at the UI/UX level.  I also have a keen interest in mobile application development which I have a little bit of experience with.

Dev-Ops

The position was certainly more oriented as an Ops developer, I learned a lot about automation in general, automated provisioning of systems, continuous integration, intrusion detection, up-time monitoring of systems, puppet, multi-mechanize, etc.  There’s really a lot to this role and it was an enlightening process which I will be able to apply to my future endeavors when necessary.   Learning Puppet was probably one of the most interesting things that I did.  I had stood up many Linux systems by hand in the past but learning the declarative puppet DSL was a fairly pleasant experience.

There’s also the Dev portion of that title, which encompassed working on our Grails/MongoDB stack with a lot of other cool tools thrown in.  So I was exposed to some of the most bleeding edge toolkits that the other three developers were enriching themselves with in their own areas of specialization.  I was also responsible for integrating my old friend Drupal into our application using the Services module.  So it was rewarding in that I was given direction from the other specialists in each of these areas and learned the right way to use these tools from professionals.

This isn’t really any of your business

Some of you may know that I have a degree in business.  A business degree is useful because no matter where you work, sans a few select cases, you’re in business.  It’s useful to know the etiquette and some of the strategy surrounding running a successful business.  Things like accounting and business communications are a must.  In hindsight, maybe that’s why I had the anxiety I had when I made the decision to go to the startup, some of the fundamentals seemed fuzzy.  But given I’d never really tried something like bootstrapping a startup, I knew I had a lot to learn.

Some lessons I learned about joining burgeoning business efforts in the future:

See a comprehensive business plan and get the full value proposition pitch before saying Yes

It disappoints me that I was not more diligent on this considering that one of the things I learned in Entrepreneurial Studies 301 is that you live an die by your value proposition.  You need more than an elevator pitch if you want to be successful. I guess I needed to understand more about software startup space, and maybe needed to learn a bit of a hard lesson here.

Where there is steak there is at least a little sizzle

It wasn’t really an issue that we would have good ideas when you looked under the hood, but our paint job lacking a bit.  It was a fail to not have a full marketing plan UP FRONT.  It’s incredibly difficult to get any buzz going about an incomplete product that nobody can use without any thin veneer of cool.  Marketing Matters, this is an interesting lesson from an engineer's perspective, especially given my stance on advertising.

There’s more to a brand name than just the letters, names should be clever

I remember when I made the first pro/con list for this opportunity, there were a lot of pros, but in the con category, a big fat circle around “not a desirable name”.  I rationalized overlooking that based on the quality of the engineers that had already been employed, but later we all agreed that the name was a problem and re-branding at that point was impossible.  See previous lesson.

Get percentage points

I remember when I got the options package and thought that a fixed number of shares kind of stinks.  Having percentage points obviously ensures you always own the same amount of the company.  I also think I should have gotten much more.  Having less than 1% ownership in a company that is less than 10 people, is not worth taking any cut in your industry rate.  For me I was already in that hole by working at a non-profit before, but now that I’m not, I don’t think I could take another risk like this without 3-5% ownership.

Onward

As I’ve detailed earlier in this diatribe, I think I’ve found my path.  I will be moving in the direction of UI, and Mobile.  Although this experience has not honed these skills to perfection, it has made my mind a lot more focused for future successes.  It allows me to move forward with confidence knowing what I know about myself.

This experience has opened up many doors for me already, and in just a few weeks I will be starting my position as a senior engineer at Empathy Lab.  I’m excited about this opportunity because it will expose me to some of the leading UX/UI architects, designers and developers in the area.  They have diverse customers with varying needs.  One of their latest large projects is the entire interactive experience for the American Red Cross.  This will be an opportunity to learn a lot about how successful brands operate, and how software empowers this process for the user's benefit.  It will be nice to deliver products that millions of people will use.

From a career development standpoint, leaving my previous corporate job allowed me to become a better problem solver.  The kind of growth I’ve seen in my career from these choices could not have been achieved without taking these risks.

In closing, I just want to thank foremost the love of my life Laura, and all my family and friends who have supported me through this process, in the good times and bad, you all played a roll.  I look forward to the future good times that I will hopefully share with you all.