To have a successful business right now is to have built it on a foundation of systemic racism. That's kind of a historical fact. It doesn't mean your business is super actively racist; it means it's thrived in a system that was designed to be super actively racist.

People spend a lot of time building beautiful websites, and I think that's important in certain types of businesses, but when you're talking about a business where you're trying to get somebody through a very difficult experience and something more functional, it's far more important that the product is easy to use.

If you spend all of your time fighting fires, you may miss critical opportunities to build your business. You'll be all reaction and no action. But if you let fires go on too long, you'll get burned. Deciding which fires you let burn and how long you let them burn for can make the difference between success and failure.

The thing that I also say to my fellow business Americans is about this election. What we have before us is a choice not between a Democrat and a Republican; I think we have a choice between an empathetic human being and a fully self-interested entity. We have a choice between right and wrong in a basic sense.

I believe successful entrepreneurs need ideas, money, good timing, and a hefty dose of luck, but none of those matter if you don't have grit.

The advice I always give founders is, 'Don't ask people what they think about your idea; ask them what's wrong with your idea. Invite them to poke holes in it because you want to find those holes before you bring your idea into the world.'

When it comes to old established rituals, people often follow them without question. Just like in families and communities, rituals are passed down in companies through the generations. Only rarely do we stop and think 'How does this thing we're doing move me closer to my true objective?'

Speed to productivity is the key metric in onboarding. The faster your users get good at your product, the more likely they are to stay. On the other hand, if they start feeling lost or annoyed, they might just say 'This isn't for me.'

There's a myth in Silicon Valley that successful entrepreneurs, like oil prospectors, ultimately just get lucky. They sink a well in the right field at the right time, and they've been cashing in on that guiser ever since. I won't deny that luck plays a huge role in any highly risky career, but I don't know of many entrepreneurs who strike oil on their first try or their second or even their 20th attempt. You need some reason to keep going, and this is normally what we call grit or persistence.

Since this pandemic has started, our employees, on average, have 1.7 hours more meetings every single day. Totally unsustainable. People are burning out sitting in front of Zoom screens all day long.

One of my favorite quotations is from Robert De Niro in the movie 'Ronin,' which is 'If there is a question, there is no question.' And the parallel in entrepreneurship is 'If you don't have an absolutely solid theory of competitive differentiation, you do not have competitive differentiation,' and it's really important to have competitive differentiation.

I think if you can create a company that brings people's dreams to reality, it's likely to be successful.

The way this disease [COVID-19] will play out: We had the most acute phase where we were worried about overloading our hospitals; we now have the poor leadership phase where we know roughly what to do—I'll call it the mask phase; then, we're going to have the getting it under control phase, which I hope occurs very soon, but that phase is going to take quite a bit of work.

What you tolerate is what you are. So, if you tolerate white supremacists on your platform, you're a platform for white supremacists ... Unless you say what is and is not acceptable on your platform, it just becomes a disaster because you want to be part of a community that share your values, and you don't share values with white supremacists.

Before you go marching out into the world, do an internal assessment. You say black lives matter—check your board, check your hiring practices, check your compensation schemes, and just understand yourself as a business. Where are you on this issue?

What separates a true north from just a direction you happen to be going is this: Will you follow it even if it hurts—even if it means you fail? If you'd rather go under than violate your first principles, you know they're guiding you true.

When I talk to various people who are starting up in business, the most important thing I can tell them is delegate. Find somebody better than yourself to do the day-to-day running. Make sure that you can find time to think about the bigger picture.

A long, frustrating ramp up to proficiency isn't just inefficient; it's actually discouraging. When someone has a bad onboarding experience, it can turn them off not to just that one piece of software but to an entire creative path.

The reality is that the team that you build is the company that you build. I personally focus a lot of my time and energy on recruiting and developing the talent from within. I just think that's probably the most important thing that a leader can do that allows you to scale.

In June [2020], when we polled our employees, 23% of the employees wanted to return to the office—only 23%! So, at that point in June [2020], we were like 'Oh my gosh, no one even wants to come back to the office.' Now [in late 2020], when we poll our employees, it's 72%.