So I've realized recently that there is a big difference between the way that most engineers talk and the way that successful entrepreneurs talk. To summarize, most engineers are inherently somewhat conservative and pessimistic, while successful entrepreneurs are unrealistically optimistic. You have all heard something similar to the interaction that I'm about to summarize:Entrepreneur: We need to finish this software by next Friday so that we can land that big new customer. You're going to deliver it by then, right?
Engineer: That's impossible. No chance. We still haven't started working on two major features.
Entrepreneur: Why? What tasks do we need to finish? I thought we outlined them all, and we only estimated one more week of development.
Engineer: We're running a bit behind schedule on development. We might be able to finish writing the code in two weeks, but we're going to have to cut some corners, and it probably won't be tested enough.
Entrepreneur: Ok. So you have a week to finish. I promised the customer that our software would be ready by then. We can launch those features in our first maintenance release.
Engineer: Grumble Grumble So the engineer thinks that the entrepreneur is reckless and crazy, and the entrepreneur can't understand why the engineer is always such a sourpuss. Clearly, they are speaking two different languages (we'll later get into why that is). The postscript (in the ideal case) is that the engineering team delivers the software in a week and a half, and it works pretty well (although there are a few bugs that were fixed in the maintenance release, and those features turned out to be unnecessary). The engineer gets his paycheck, and the company makes a million dollars from the deal that they have signed. Essentially, each acted in a rational way given his incentives and understanding of the world, but there was clearly a conflict.
What Makes Them Tick?
So the primary cause of tension here is that the engineer and the entrepreneur are being graded on two very different sets of criteria. The engineer is successful if he delivers a product that works well (from a technical perspective) and is on schedule. Meanwhile, the entrepreneur wants to build a successful business. A successful business usually involves building something that works well, but there is a lot more to it than just that (I know of many products that worked well but that people didn't want, or even that worked well but were unable to successfully reach their target audiences). At the end of the day, the entrepreneur is successful if he builds something of value and eventually generates a good return for his investors, whether through sales, an acquisition, or even an IPO (I'm omitting social entrepreneurs, who also build value, albeit in a slightly different way).
The Reality Distortion Field
Whenever I meet a successful entrepreneur, I inevitably come to the conclusion that he or she resides in a completely different world than the rest of us. He imagines accomplishing not just what he already knows how to do, but he looks just beyond the borders of the realm of possibility, and figures out how to do that. When Steve Jobs first imagined the iPad, no such thing existed. But he knew that technology was approaching the point where it would be possible, and he found engineers who could build it for him (successful entrepreneurs project a reality distortion field that draws in everyone around them). In the end, this eventually led to Apple shipping over 275,000 iOS devices a day. In the longer term, I can see this vision being disruptive to the PC as we currently know it.
1) Learns the skills he needs to succeed
2) Manages to attract the people he needs to succeed
3) Learns a lot, and is successful at his next company (or five companies later). The entrepreneur never sees anything as a failure. He just learns from all of his steps (whether correct or missteps), and tries again. James Lindenbaum is one of those prototypical entrepreneurs. Heroku was like his fifth company; he failed a lot, but inevitably kept going until he was wildly successful (and I predict that this won't be his last or greatest success). By contrast, a lot of engineers see everything as a failure. No matter how much they accomplish, they always see something that could have been done better.
Why Entrepreneurs and Engineers Work Together
The irony is that, even though they hate to admit it, most engineers actually love working with entrepreneurs because they are always so optimistic. Even though they tell everyone else that the entrepreneurs "have no clue what they are doing," they secretly wish they were able to totally buy into a vision, and to project that reality distortion zone. Likewise, most smart entrepreneurs surround themselves with engineers who keep them at least loosely grounded in reality. It's an interesting synergy, and one that is necessary to build successful technology company. Rarely, there is that paradoxical person who can simultaneously fill both roles, but these are about as rare as unicorns...