The New York Times had a really excellent profile on Uber's CEO, Travis Kalanick, and it doesn't paint a very good picture of the guy. That's a bummer, because Uber is arguably one of the more disruptive forces to come out of technology, and probably one of the most overdue, in a long time. I would go so far as to say it's even necessary.
But the profile is one of extreme bro culture and questionable judgment at every turn, in order to further the company's goals. I'm not cool with that, especially at the expense (allegedly) of blatant sexism. "Winning," whatever that means, can't come at the expense of your people, your partners or the world. That's just now how you should roll.
The first genuine startup tech company I worked for was Insurance.com, and it was probably an ideal first for me as far as pure technology companies goes. (Technically, it was an auto insurance agency, but in practical terms it was a software company that sold insurance.) While it ultimately got into trouble because it funded growth on the back of a what should have been an "extra" non-core revenue stream instead of the long-term, recurring revenue that was safe, it was good to its people and fostered an excellent environment. Good ideas came from everywhere, within the development team to marketing and the call center. Sure, there were kingdoms, but generally good ideas were able to come up from everywhere. When I look back at it, I was definitely critical and skeptical at the start, and definitely at the end, but that was a company full of good people focused on all of the right things. It's the reason that the outcome of our product was so great, even if the spending at the executive level had a fatal flaw.
I'm back into a startup that is bootstrapped and therefore commanding its own destiny. My boss is very keyed into the "why" for the business, which means that while growing the business and making it successful is important, there's a very explicit understanding that we're making the lives of our customers better. What makes this even more fun for me is that I've taken on more responsibility for developing our staff, and as people who know me understand, that's a big deal to me. My inner coach loves this. I have one direct report today, and another coming soon, but I've just pulled in a dotted-line report to accelerate professional growth. We're going to win because we focus on our customers and our people, and that's the right thing to do.
I'm lucky that we have a lot of options in our line of work, and if we're really paying attention, we see that there are definitely "right" and "wrong" ways to conduct ourselves. Winning isn't winning if you have to sell your soul, cheat or trivialize people. The Uber story has so many examples of what not to do, and I hope that they can turn it around, because I think it's an important service. But if they don't, it will be a good example of why it's OK to be ambitious and still have a moral compass.