On the heels of Steve Jobs’ announcement that he’s retiring from Apple (okay, I’m a little late for the heels, but there was a pseudo-hurricane),  I thought I’d reflect on the top five things I take from the single greatest entrepreneur in the history of consumer technology.

1. Know Your Customer:  When you start a business or step into an existing enterprise, it becomes easy to focus on operational or strategic issues.  It seems to me that having an almost religious obsession with the customer experience is the best bet you can make on where to expend your limited resources.

  • Jobs understood that his customers want their computing experiences to be seamless, and that they’re not interested in working through compatibility issues between manufacturers and software developers.  This understanding has allowed Apple to enjoy premium prices in a commoditized market for decades.
  • Remember what everyone was saying about the iPad before it was released?  Those who doubted the market demand for tablets spent months trying to catch up after the iPad’s initial success,  only to release products that felt like cheap knockoffs months too late.
  • An example from another successful tech company: when Google’s Page Rank algorithm was first created, the company’s first strategy was to license its search technology to existing search engine websites.  The issue, as the story is told, is that Google’s technology was too fast and, if users left the search sites too quickly it would hurt display advertising revenues.  Of course, users wanted fast search and that became the model that eventually won out.

There are a million other great examples of this approach paying off in big ways.  Know your customer and understand their needs.

2. You Cannot Replicate Culture: One of the reasons that Apple’s stock didn’t take a big hit following Jobs’ announcement is that investors have bought into the idea that not much is going to change at Apple.  The reason that nothing is going to change is because their culture is fully-baked.  One of the advantages of being a first-mover is that you can spend more time developing your product than your fast followers can.  Apple is a design firm first and that DNA shows in everything they release.  That type of culture is almost impossible to replicate; it will give Apple a competitive advantage for years to come.

3. Do What You Love / Follow Intuition:  Check out this quote from Jean-Louis Gassee.  I think that doing what you love means accepting that fact that a lot of people will be sure that you’re doing it wrong.   I’m finishing a behavioral finance class with a professor who spent all of 1999 shorting tech stocks.  He said that he became physically ill every night as the market continued to rise– that he didn’t sleep for a year.  But his intuition was right: doubling your market cap every month is unsustainable and it doesn’t make any sense.  When I think about Steve Jobs, I think about how difficult it must have been to get fired from the company that you founded.  The idea that ‘you’re doing it wrong’ can affect your decision-making if you let it and the contagion can eat you up, even if you were right in the first place.  Doing what you truly love helps you mitigate those downsides and it helps you trust your intuitions.

4. Think Big and Small: Apple’s products are a collection of seamlessly integrated UX details.  While Apple changed the world in a lot of ways, most of what they accomplished came through creating superior user experiences– the details.  For example,  while strategy played a roll with the iPod (iTunes music store), everyone bought an iPod because it was slick and it made digital music fun.  I think that the importance of UX / design cannot be overstated, especially in web and mobile products.

5. Fail: As Jobs himself said in his commencement address at Stanford,  “you can only connect the dots looking backwards”.  Creating and ideating are the only tools you have to build something great.  Failing is, for most people, an inevitable outcome for the majority of your attempts.   Don’t think Apple has had any failures?  Check out these five epic Apple fails (granted, not all of them occurred on Steve Jobs’ watch).  Aside from these more esoteric failures,  think about the battle for industry standard when the PC first came out.  Jobs and Apple lost in a glorious fashion to the Wintel model.  As a result of that failure, Jobs learned the importance of available software applications on any system– which is why we have the App Store today and why the iPhone and iPad have been such a huge success.  Early failures + great leaders = future successes.