I have spent the last 20 years of my professional career building web-based products and services and growing businesses on the web. During that time I have worked for early stage startups,  fortune 500 behemoths and everything in between. Most recently I worked as the  CTO of Napster, a late stage startup. I had a lot of fun there. We rebuilt all of the consumer facing applications, beat waterfall and a “business vs. technology” mindset out of the organization, and generally introduced elements of risk taking and excitement back into the culture.  But probably the most interesting and valuable part of my Napster experience was  the acquisition of Napster by BestBuy in October of 2008. As a result of that event, I learned a great deal about the differences in philosophy, attitude, and approach that inherently exist between a mature multi-billion dollar corporation and a smaller online startup.  Though many of the words and concepts we used to talk about markets, products, consumers, and projects were the same, our interpretations were very different.  At first we ignored or marginalized this, thinking that by working together we would ultimately end up “on the same page”. Eventually, it became obvious that we needed to spend a fair amount of time developing a common language and digging into the perspectives everyone was bringing to the table.  I am a strong proponent of both formal approaches to Customer Development (Steve Blank, Eric Ries) and lean/agile approaches to Product Development (Lean, Scrum, XP).  I bring this up because my thoughts and attitudes in these two areas color how I view  products, markets, businesses, and consumers and definitely influenced my experience with the BestBuy acquisition. As the transition progressed and we all began to acquire real working experience with one another, I identified a set of issues that I believe lay at the basis of many of the challenges we faced.

1. Empirical approaches to Product Development are easy to talk about but hard to do  (deterministic approaches die hard)
2. Flexibility is easy to champion and talk about but hard to build into any culture that has focused on efficiency for many years
3. Too many independent and separate  functional disciplines creates waste and opportunity cost
4. Thinking about technical risk is easier than thinking about market risk
5. “Complete” is not a meaningful concept and its pursuit causes problems (No Pareto)
6. Easier to focus on reducing internal risks than product/market fit risks
7. Hierarchical decision-making is more comfortable than demonstration based decision-making
8. Corporate IT organizational cultures are completely different from product development organizational cultures
9. Product Management is a poorly understood discipline
10. With large cash reserves can come a willingness to create complexity where it is not needed

I am going to spend the next couple of weeks detailing each of these observations and talking about how I am applying some of what I learned in my current situation