Entrepreneur Talk Vs Engineer Talk

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).

Now, If you want to build something on-time that works well, it makes sense to be pessimistic about your schedule and what you can deliver (obviously there is a reasonable upper bound on this). Most good engineers I have met (who aren't managers) seem to always say "It can't be done. But, if it were possible, this is how long it might take." Then, they somehow manage to deliver the product in 3/4 of the initially estimated time (and maybe they manage to work in a few useless features that they think would be cool). Good engineers succeed by executing well on complicated technical tasks. Unlike entrepreneurs, they tend to get paid mostly in salary (if they are smart). If the company fails, they can pretty easily find another job paying about the same amount of money (or maybe even a little more).

However, when you want to build something of value, the goal is not to launch products that work perfectly or are perfectly on schedule, but to figure out what people want and to deliver that. Sometimes, it is important to cut corners in the short term if that gives you the best chance to reach your eventual goal. Even if an entrepreneur delivers a product that only delivers 10% of the features he set out to build, he can still be wildly successful (if those few features are the ones that people actually want and are willing to pay for). His goal is not to build things, but to build value. I know of successful entrepreneurs who completely failed in their original project, but who still managed to generate a good return by realizing that they had amassed significant talent equity. And how do you build the maximum amount of value?

Well, that requires you to be unreasonably optimistic.

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.

There is an old saying among followers of Neuro Linguistic Programming - A belief doesn't have to be true to be helpful. Sometimes, being delusional can actually cause you to ignore things that have held you back, and the ones who accomplish the most are often the ones who imagine they can accomplish the most. An engineer likes to have the entire solution inside his head before he starts. He begins at the present moment, and imagines every detail between the current moment and the time when his hypothetical company IPOs. Then, he inevitably figures out that the numbers won't quite work out, and he decides to go back to work on Monday. This is what makes him good at being an engineer, and it is also what holds him back. Not surprisingly, the engineer doesn't do well with uncertainty. If he does go out and start a company, he will inevitably figure out that things aren't going to work out the way he imagined, and this is often what kills the company (unless his cofounder can get him back on track).

The entrepreneur, on the other hand, sees an opportunity, decides that the market is huge, and he decides to go for it. He may not have any real skills when he starts, but he has enough ability to handle uncertainty that he inevitably either:
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...

Strangely, it isn't impossible for an engineer to become a successful entrepreneur, but it does require a pretty radical shift in thinking. He needs to stop always seeing things for what they are, and learn to occasionally look at things for what they could be. Sadly, a lot of people just aren't able to make this leap, and end up as wannabe entrepreneurs who didn't make it for some reason or another. In thinking about and writing this essay, I've realized that a lot of my tendencies fall on the "engineer" side, and that I could benefit a lot from seeing things "the other way."
4 responses
Dana, great overview. You were able to put into words something I've been thinking about, and observing for some time now.

One issue that I've come across, to often, is the engineer playing the role of the entrepreneur. Often times I find a talented technical engineer who has been able to impress enough money out of a VC to run a startup. This person takes the role of business leadership AND technical leadership which ends up directly addressing your point.

This person will typically fall back on what's intuitive to them, the engineering perspective (which you directly address in your post) and the bigger, broader thinking then get's ignored.

Not that I've have a huge amount of examples to work of off, but everytime I've run across this situation it has failed. Apparently, I haven't seen any Unicorns yet :)

Thanks again for the great post!

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