I think your example shows the importance of learning how shrewd businesspeople think.

<< example #1 >>

My first business mentor was literally a con artist. I was starting my first business and he, ostensibly a retired lawyer, took me under his wing... while we worked together he helped me a lot, but one day he skipped town and left me (and a few other people) screwed.

It was some of the best money I ever spent on education -- it's not every day you get exposed to deception at that level of sophistication.

Since then I've interacted with some very ethical businesspeople who understand things in a remarkably similar way to that con artist -- they are acutely aware of the mechanics of perception manipulation, which can be applied to good or bad ends in almost any conceivable field of endeavor.

<< example #2 >>

One big reason I burnt out last year is because I didn't pay attention to what I'd learned in example #1 because I started a company with ethical people I knew extremely well (read: even if you're with great people, you still need to know exactly what you're committing to).

I had equity, but I was the youngest & least-experienced founder, and left behind the other founder & founder-investor in N. America to go and manage everything myself on the other side of the world, in China.

A few things that contributed to a living hell:

* I had zero salary (ALL my money came from expense claims) so I couldn't buy as much as a chocolate bar without running a stressful "is-this-worth-the-cost-to-investors" calculation in my head -- I couldn't internalize even a single dollar of "cost" to my own personal budget, and I let this stress me out because my co-founders were people I cared about. I felt like a child who had to ask his parents before buying anything.

* I lived in my office. And let me say that living alone out of an office in a foreign country with a nearly impenetrable culture and language is not the same as sharing an apartment in a hip city with your co-founder/friends.

* Decision-making was terribly slow -- it would take days to go back and forth b/w China and N. America on even the simplest issues. We totally underestimated the cost of this.

* My vesting period was undefined, and we had no official corporate paperwork, despite already having spent $100k+ on startup costs. I didn't realize this was a problem until I burnt out, and found that a simple conversation over dinner was all it took for me to be entirely out of the picture equity-wise.

* My other founder insisted on being the sole interface to the founder-investor. Which meant that information flow, despite being an extremely small startup, was already horribly distorted. There was already a chain of communication this long: Staff (6 people) > Project Manager > Me > Founder #2 > Founder-Investor. And the Founder-Investor was the only person who had any real experience in manufacturing, which was what we got ourselves into.

By the end, I had not even a hint of feeling like a responsible, independent person, let alone leader of a company. Every single aspect of my existence was, technically even if not practically, under the control of "the company" -- the food I ate, the office I lived in, the staff I hired... and I'd agreed to it all, in a trusting sort of way, because I didn't see that "good people" still require "good structure" in order to function properly. It was the least entrepreneurial position I've ever felt myself to be in, despite being the most entrepreneurial from a cursory glance.

Things would've been a lot smoother if I'd let my "shrewd businessperson" self take over initial discussions instead of my more natural "trusting friend" self, which left all the details to some nonexistent universal positive force of social goodness.