The hard thing isn’t setting a big, hairy, audacious goal. The hard thing is laying people off when you miss the big goal. The hard thing isn’t hiring great people. The hard thing is when those “great people” develop a sense of entitlement and start demanding unreasonable things. The hard thing isn’t setting up an organizational chart. The hard thing is getting people to communicate within the organization that you just designed. The hard thing isn’t dreaming big. The hard thing is waking up in the middle of the night in a cold sweat when the dream turns into a nightmare. (Location 75)

Most business relationships either become too tense to tolerate or not tense enough to be productive after a while. Either people challenge each other to the point where they don’t like each other or they become complacent about each other’s feedback and no longer benefit from the relationship. (Location 320)

With Marc and me, even after eighteen years, he upsets me almost every day by finding something wrong in my thinking, and I do the same for him. It works. (Location 322)

We were going to go bankrupt for sure. I did not sleep more than two hours total during that entire three-week trip. (Location 502)

IF YOU ARE GOING TO EAT SHIT, DON’T NIBBLE (Location 546)

Note: LOLLL

During the road show, as a way to break the tension, Marc would say, “Remember, Ben, things are always darkest before they go completely black.” He was joking, but as we entered our first quarter as a public company, those words seemed prescient. (Location 547)

Typically, investors expect that companies will refrain from going public if they can’t hit at least their first year’s forecast. (Location 552)

So we reset guidance for the year, slashing our original forecast of $75 million in projected revenue to $55 million. Resetting revenue guidance also meant resetting expense guidance, and that meant laying people off. We’d been the darling of the startup world, and now I had to send home 15 percent of our employees. It was the clearest indication yet that I was failing. Failing my investors, failing my employees, and failing myself. (Location 560)

With a vote of no confidence from our banks and a lowered revenue forecast, the stock price plummeted from $6 a share to $2. Despite the mammoth negative momentum, we soldiered on, and were putting together a fairly strong quarter in the third quarter of 2001. Then, on September 11, terrorists hijacked four jetliners, flying two into the World Trade Center and another into the Pentagon, and in the end throwing the whole world into chaos. (Location 567)

Note: Rains it pours