Playing To Your Strengths - A Cautionary Tale

A few months ago, I was speaking to a now ex-cofounder. We had hit a
rough patch where we invalidated our original hypothesis, and were
thinking about new directions for our business. I was trying to figure
out the least expensive strategy that would allow us to get back on
track, while he kept proposing things that would require several
months of engineering effort.

At the time, I was thinking about leaving his team, mostly because he
seemed to be dead-set on following a single path, come hell or
highwater. He had spent several years working on this product without
really launching anything, and had brought me in much later as an
engineering cofounder. His excuse for his failure thus far was "I
didn't have a competent engineer."

Then, it sort of hit me. Based on your personal talents and the
talents of your founding team, certain courses of action are MUCH more
expensive than others. If you are an enterprise salesperson (as this
guy was before he left to start a company), sales is fairly cheap.
Engineering, however, was pretty expensive for him. It took him years
to find a good engineering team, and it would have cost him 30-50% of
the company if we had stayed. In hindsight, those years could have
been spent making an enterprise play. Once he did the sales, he could
hire the engineers to build the product.

For me, an engineer by trade, building is cheap, but selling is
expensive. I spent all summer trying unsuccessfully to sell my product
to enterprises, and I had no idea where to find people who actually
knew how to sell. This showed me that I need to primarily focus on
building products, because that best leverages my talents. Unless I
have a salesperson or a marketer on my cofounding team, it doesn't
make sense to do something that requires heavy sales.

So, what can we learn from this? First of all, when you evaluate
business ideas, choose ones that play to your strengths. Take an
honest look at the skills of your founding team, and ask yourselves,
"do we have what it requires to execute here?" Sure, an engineer can
sell a little bit, but most engineers will get demotivated pretty
quickly if they spend most of their time selling. Likewise, if your
core competency is sales, you should be thinking up things that you
can sell BEFORE they are built (and that don't require two years of
engineering work before sales can start working).

Furthermore, you may want to make tweaks to your founding team to
account for the business idea. If you have two engineers on your team,
you might not want to bring on a third engineering cofounder. Maybe
that third guy should know sales, or maybe he should be an Internet
marketer. It all depends on what you need to make your company
successful. If you pick the wrong person, it could be worse than doing
nothing.

So, here's an exercise: think of the first (or next) few milestones
that you need to hit to build your company. Now, think about what
skills are required to hit those milestones, and then ask yourself
whether these skills are present in the founding team. If not, then
you should consider changing either the idea or the team. Pick a
product strategy that's reasonably cheap for your team to execute,
because starting a company is already pretty hard, and you don't need
to make your lives any more difficult.