Your first company dealt in e-commerce, before anyone really used that term. How can founders be ahead of the curve?
There are a lot of people who are much smarter than I am, who are much more visionary thinkers, and who worked a lot harder, but who just didn't get the lucky breaks. We started things at the right time. What you should be doing is looking at industries that haven't seen innovation in 10 or 20 years.
How have your thoughts about leadership evolved over the years?
It's a thing you do, not talk about. With some words, how often you say them is inversely proportional to how often you do them. Like innovation. Companies that have a senior vice president of innovation don't innovate very often.
How can a young entrepreneur find a great mentor?
The most important thing is having good questions. In my experience, every single person, no matter how amazing and legendary, will always take the time to answer good questions. There have been all kinds of research about how answering questions gives people the same dopamine hit as gambling. Come up with good questions and ask.
What advice from your early mentors really stuck with you?
The best advice came from Hiroshi Mikitani, the co-founder and CEO of Rakuten. He said that every time your company triples in size, everything breaks. When it's just you, you figure out how things work, you hire a partner, and things are OK. But when you hire the third person, you've got to redo things. This can be people, revenue, or customers. Startups often get in trouble because they're growing so quickly they don't deal with these triplings.
Now that you're an investor, what do you look for in a pitch?
I'm looking for founders who can articulate: What is the world going to look like if my company succeeds? Is that a better place than where we are now? Make me want to live in that world. I want to be like, "I want to live there more than here." If people can do that, they're already ahead of 99 percent of the people who are pitching.