This is the question I’ve been pondering ever since hearing the story of Michael Robertson (founder of MP3.com) on ThisWeekInStartups (skip to the interview part around 44 minutes.)

It seems that Robertson’s entrepreneurial strategy — with all his doom and glory — has been to see a general trend (he noticed the word “MP3” was rising on search engine zeitgeists’), to learn about it and chase it, and then to navigate and improvise his way around where things are heading, what users want, and what is technically or strategically achievable. This is a much different style of entrepreneurship to the one we’re used to hearing about — the one of the long-term visionary strategical genius — and one I’m trying to get familiar with.

The idea is that with this style of entrepreneurship, the real genius isn’t in seeing that MP3s will be the future and coming up with an elaborate plan in making that happen, but in seeing that MP3s are a happening trend, in imagining some possibilities and executing on one, learning from every external factor (the users, the lawsuits), and then recallibrating that plan. Instead of following a virtual path that you created in your head, you’re essentially making one and improvising where need be: using all your past knowledge and experience, and the current ‘status of the world’.

When you hear Robertson talk about it and the way things turned out, you realize that despite taking the ‘non-visionary’ approach, he infact turns out to be the visionary — more so than anyone who tries to. The iTunes store? Robertson had that vision, but he couldn’t get the business side of things from the record industry’s part to line up. Steve Jobs made a beautiful device, created a monopoly around it, and he made it work. The app store? Robertson had that vision, too, when he attempted to create a user-friendly retail version of Linux where apps could essentially be downloaded and purchased from a single ‘store’. Steve Jobs made a beautiful device, created a monopoly around it, and he made it work.

When you examine Robertson’s outcomes, along with learning that he worked on pretty much everything we use today before we knew it existed, you also get to see the pitfalls of his approach: execution. Essentially, you never have time to sit and think — since you’re always, in a way, thinking and executing constantly on new things that have never been tried before. This results in you geting so ahead of navigating everything, that you inevitably become the first guy to take the arrow. The people after learn from it, device a master plan along with some key change that resulted in your gloom, and if they get it right, like Steve Jobs did — twice — they become the hero, leaving you in the dust.

In any case, this is a must-listen interview, and it has made Michael Robertson, a guy who I didn’t know a thing about a day or two ago, into an instant favorite entrepreneur of mine. Only because of what he did a few years ago are you getting to listen to music on your iPod, or download cool apps on your iPhone, or store things in the cloud.

The basic takeaway: Michael Robertson rattled through the bushes, swiping his sword around to create a path, running into deadends and discovering new land. Steve Jobs came along with a helicopter, checked out the already-created path from above and mapped out the rest on paper. Then, he buzzed through it in his Jeep Cherokee, and the whole world followed.