We just rebranded and redesigned the entire Grouper site in about 3 weeks. We came in under budget, perfectly on time, and the results exceeded our expectations. It couldn’t have gone any better.

We owe much of this to a single piece of brilliant advice we received a few months ago, which applies equally well to hiring a designer part-time or full-time.

I was chatting with Aaron Epstein and Darius Monsef (aka Bubs), the founders of Creative Market and Color Lovers — both awesome, designer-focused sites. I figured if anyone would have pro tips about working with designers it’d be them. They didn’t disappoint and delivered this gem:

Make sure you like the designer’s style so much that you would trust them to create a design for you without any input.

If you try to force a designer into a style that’s not their own it’s often slow and painful; if they’re working in their own favorite...

I rep a Grouper t-shirt every, single day. (Fortunately, I have a few).

There are two reasons why I do this:

1. I don’t have to think about what to wear.
2. Free advertising.

The first reason I stole from Steve Jobs. His iconic outfit is often misunderstood. He wore that famous black mock turtleneck, Levi’s, and New Balances not to make a fashion statement, but almost for the complete opposite reason: so he didn’t have to think about what to wear. Apple is a tremendously focused company and it stemmed from a leader who tuned out all distractions, even ones as trivial as getting dressed.

The second reason was inspired by Larry and Sergey. An early Google investor told me that they wore their Google t-shirts every day in the early years. “Free advertising,” they explained.

Startups are hard. Every little bit helps.

Many tech companies are trying to “disrupt” existing industries, but few actually do. There is, however, one unmistakable sign of real disruption: when the incumbents try to change the rules.

Uber, the outstanding on-demand car service, has ascended to this rare status. The taxicab industry/mafia has long felt threatened by Uber (even forcing them to drop their original name of UberCab). Earlier today the local government in Washington DC voted on legislation specifically designed to thwart Uber’s new product, UberX – a hybrid fleet that offers lower prices than Uber’s standard black cars. The cab lobby attempted to push through a “minimum fare” that was blatantly designed to protect them from competition with UberX, and would without question hurt consumers.

Airbnb is waging a similar battle with the hotel industry. The Hyatts and Hiltons of the world have good reason to feel...

I moved to Silicon Valley when I was 19 to embark on my first startup. I knew nothing and virtually nobody except for my co-founder.

It was 2006 and it wasn’t as easy to learn the ropes back then. This was before much of today’s startup infrastructure existed. There was no Hacker News or Github or Twitter or AngelList or Stack Overflow. This was before EC2 and the iPhone, when Myspace still had ten times more users than Facebook. Y Combinator was just getting started.

We raised some money and assembled an amazing team, but struggled as a company. Good people came and went, and as the ship was sinking many people jumped off before we went totally under in the summer of 2008. At our peak we had 25 full-time employees and ultimately had to let go everyone who remained.

One thing that stays with me is the way in which people carried themselves on the way down. Most were gracious and...