The serial entrepreneur behind Blogger, Twitter, and now Medium has discovered the secret to making his people happy.
-- As told to Lindsay Blakely
What's the biggest mistake you've made as a leader?
I started my first company before I had had a job in a company, so I knew nothing--and it was a somewhat painful learning process. At first, I looked at management as a necessary evil: "I can't do everything myself, so I guess I'll hire people, and grin and bear it, and do as little managing as possible." It turns out that does not lead to great results. You have to think that your employees are your most important customers, and figure out what will make them happy.
So what makes them happy?
Trust. Lack of trust doesn't necessarily come from people lying and cheating; it generally comes from a lack of good communication. At my first two companies, I would wait until difficult conversations became really difficult. I didn't want that to happen at Medium. The most useful thing I've learned is to be open about how you're feeling without being accusatory. If you approach people assuming that you're on the same side, you can collaborate to find solutions.
How do you feel about the state of the internet today?
I used to be much more utopian--and naive. I thought once this amazing, new information utility was at our fingertips, as individuals and as a society we were going to make better decisions. Obviously, that's not been universally true. The rapid dissemination of information means the truth is out there--but so is a lot of BS. It's harder than it used to be to separate the two.
How do you stick to long-term ambitious goals when investors push for faster results?
You have to be aligned about what progress actually means. It's OK for investors to push for results, but if they're pushing for short-term results over long-term, that's where you get in trouble. Progress doesn't always come in the form of big numbers or monetization. While Twitter was criticized publicly for taking a long time to make money, it wasn't criticized by our investors or our board. It wasn't a matter of not knowing how to make money; that just wasn't the most important thing we could do. We were in alignment about that. Then when we did start making money, it ended up working very well.