I’ve been fortunate at Flexport in that I had never been a freight forwarder, so there was never a moment at Flexport where I could tell everyone what to do… so at no point did the company ever depend on what Ryan told them to do.

My naivete around forwarding actually turned out to be a good thing in the long run because I can focus on culture, on recruiting, on org design, instead of telling people what to do.

One of the key misunderstandings of entrepreneurship is that it is all about daring founders risking everything to change the world.

My story is the opposite; I designed my life such that I could not fail, even as some of my business experiments did. That is not the only way to start a business, of course, but for a would-be entrepreneur with a lot of debt, it might be the most responsible.

I don’t know timeframes. Even Flexport, I don’t know what timeframe we’ll be successful, but I know that if we stay in the fight, we’ll win.

You just want to make sure you set yourself up in a way that you can’t lose because you’re in the fight in perpetuity. And you’ll just keep finding new hacks.

I didn’t know what business I’d make successful, but I knew that I would do it. As long as I could make those debt payments, make my rent, and afford some food, then I’d buy myself an indefinite period of time to experiment.

Hatred of bureaucracy is not enough to keep bureaucracy away. You also need good process, good systems, great people, and clear strategies to keep the company moving fast and being agile.

I think that’s one of our great challenges that I’m obsessed with learning about at Flexport now because I don’t want to end up like these other companies where they are kind of like stuck in molasses and can’t execute. And I’ve seen it, we’re definitely moving slower than we were 6 years ago when it comes to product development and new things, you keep adding complexity to the mix and slow down.

So I’m super focused on what we can do to make people run faster, what do we need to learn, what’s the skill set, what’s the tech debt we need to pay down to make that happen…

As I’ve gotten to scale, I realize the reason those exist is to enable you to move fast. You’ll actually get more bureaucracy from not having any process and policies and standards than you will from having too much.

Talk about your ideas all the time. If the people you talk to aren’t banging down your door to buy the thing you’re imagining, it’s not a great idea.

In every business I ever founded—I’ve started 4 companies with valuations above $50M, with Flexport now at $8B—whenever I would mention the idea in casual conversation, people would beg me to start the company so they could buy the thing. If that isn’t happening to you, then your idea probably isn’t good enough, and your friends or family aren’t telling you that because they’re being nice.

You should be getting lots of successful “if-then” statements, where people commit that they would buy from you if the product did XYZ. If that isn’t happening, keep innovating. Don’t fall in love with one of your ideas until this happens. I had dozens of ideas—and still do—that I thought would work.

Success compounds. Successful people become even more successful. This seems like trivial knowledge, because on the surface all it tells you is that you should be more successful, which you were going to do anyway. But this is not trivial at all. It’s profound. Because it says that you should go for small wins. Like an engineering team developing software using agile methodologies, you should always have a working system that you can iterate on in your life.

Going for a big, giant win is not how success develops: It’s about long term commitment to daily improvement. It means finding something you can do today to create value for somebody else and, as soon as possible, finding a way to capture a portion of that value for yourself.