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I was spending all my time at the 'Crimson' - like, 70 hours a week - and I didn't go to class for, like, a year. I failed out of school. I had to leave Harvard, really, halfway through my tenure as the 'Crimson' managing editor. It was this incredibly humiliating and shocking experience.

At Wikinvest, which got renamed Sigfig, we were constantly just two or three months away from not being able to make payroll.

There's a lot of just administrative work that comes along with having employees.

The only thing I learned is that failure sucks, and you never want to do it. There's not a lot to be said for that particular lesson.

Some days you're the fire hydrant, and some days you're the dog.

I'm not going to run my business on the basis of quarterly numbers.

The way we designed self-driving payroll, it ends payroll as an independent system that you're entering information in by hand.

It feels good to have people who support you and back you and believe in you.

There's nothing easy about building a company at all. I find it really hard, just painful and difficult, and if you are successful, it's even worse than if you fail.

I'm too old to understand Snapchat.

I'll grab coffee with my wife and daughter and then am in the office around 9 or 10. From there, I usually have about 8 hours of meetings.

When professors expect a few dozen students and hundreds show up, it's a mixed blessing. While it's a testament to their popularity, it also means they have to scramble to interview and hire more teaching fellows, schedule rooms, and order lab supplies.

If Harvard officials ban the microfridge, it will leave undergraduates without any cooking appliances at all allowed in their rooms.

A good headline is far more than a summary. It has to characterize, in a few brief words, the most important themes and news items of the article it accompanies.

One of the powers of a sit-in is its visibility and potential to mobilize public opinion; the way the protest is reported in the media can have a powerful influence over its eventual success or failure.

Media organizations are frequently criticized for a heartless approach to the news. Stories that are damaging to a person's reputation make the front page just as quickly - and many would say even more quickly - as stories that enhance it.

Journalists play God when they decide for their readers when to hide information from them. Frequently, those choices are unavoidable.

The Digital Millennium Copyright Act indemnifies Internet Service Providers (ISP) such as Harvard from copyright abuses committed over their computer networks.

College students typically receive marketing offers in the mail from upwards of a hundred companies each year.

Despite the volume of 'junk' mail that students receive each year, companies that have an interest in selling their product to students say direct mailing is a key to their success.

Both in the short-run and the long-run, college students, collectively, have enormous spending power.

Lists that segment people into clearly-defined categories are particularly valuable to direct marketers, which can tailor their sales pitch to a particular demographic and, therefore, increase the likelihood of making a sale.

The battle over Napster has divided musicians and industry officials.

There are those who say the music industry must adapt to a wired world. They point to the decades-long rise in CD prices, even as manufacturing costs came down, and to data that shows Napster may actually increase sales of CDs by music-hungry customers as evidence that the music industry is simply afraid of a new technology.

One of the lasting consequences of the unrest of the late 1960s was the removal of adult authority from the lives of undergraduates at many colleges. And, as a consequence, residential communities developed much as students themselves wanted them to.

I tried paying at a restaurant with stock options. It didn't work.

With a lot of the things that seem scalable, you will find bottlenecks you never imagined that you suddenly need to find solutions for.

It's a lot easier to figure out how to scale something that doesn't feel like it would scale than it is to figure out what is actually gonna work. You're much better off going after something that will work that doesn't scale, then trying to figure how to scale it up, than you are trying to figure it all out.

Rightly or wrongly, for better or worse, valuation is a very important tool for recruiting - particularly in the markets for software engineering, where the market is really tight.

I don't know anything about Amazon's culture; I've never worked there.

There is so much headache and hassle involved in starting a business or running a business.

Zenefits is basically a service that manages all of your payroll, benefits, and associated HR details that come along with those. Dealing with new employee onboarding, offer letters, and managing that - and we do it for free.

The reality is, for small businesses, there really aren't HR systems. Small businesses are rolling their own.

If you move or get married, that has to be changed with HR, payroll, medical insurance, life insurance, etc. It is a huge administrative headache that requires a full-time staff.

Insurance brokers make way too much money for the value they provide.

A lot of scaling up a company is not very sexy or strategic.

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