The average venture capitalist meets approximately two new companies per day, 250 days per year. That’s 500 potential investments every year. And those are just the in-person opportunities. They also receive thousands of cold emails, who-knows-how-many unsolicited pitch decks, and surely the occasional unexpected pitch in an elevator. From all those opportunities, they somehow have to guess which ugly looking startups are going to turn into multi-billion dollar companies 10 years from now.

For these reasons, I don’t envy venture capitalists. Their jobs are basically impossible because they have to correctly predict startup outcomes years in advance. That can’t be…

Presumably, if someone pioneered a revolutionary technology billions of people benefit from every day, that person would be what we might call “successful.” Maybe the person isn’t rich. For example, Dr. Jonas Salk didn’t patent the polio vaccine specifically because he thought everyone should have affordable access to it. But he’s still famous for his accomplishments, and that seems pretty cool.

However, creating a world-changing technology isn’t actually a one-way ticket to professional stardom, and I have proof. That proof comes in the form of the entrepreneur who pioneered web-based email — something billions of people around the world rely…

If and when you decide to start a company, you’ll be doing so based on a huge, invisible pile of assumptions you’ve made about the world. Here’s just a small sampling of the hundreds of assumptions you’ll likely be making:

• People will want your product.
• You can access the people who would want your product in a cost-effective way.
• The people who’d want your product are willing to pay enough money to make your venture sustainable.
• You can produce your product at a cost-effective price.
• You’ll be able to find people who can help you sell your product.
• A giant…

After some early beta testing for one of my previous startups, we zeroed in on what we thought was a great market: restaurants. We’d gotten a handful of them using our product, and they loved it. Plus, in addition to being able to benefit from our product, we discovered the United States alone has over 1 million restaurants. These characteristics led to conversations between me and my co-founder that went something like this:

“If we get just one percent of the restaurant market paying us $100 per month, we’ll be generating a million dollars a month!”

For the sake of…

“It doesn’t make any sense,” the entrepreneur complained as we started our meeting. “All our competitors have crappy products that are harder to use and more expensive. Why are we having so much trouble convincing them to switch to us?”

I smiled as I remembered thinking the same thing when I was building one of my first tech companies. All our competitors were selling clunky, expensive software that took dozens of hours to configure and learn. In contrast, my team had spent months developing a gorgeous, user-friendly interface for our product that provided the same value proposition in a simpler…

I was in an auditorium surrounded by investors. We were all attending “demo day” for a startup accelerator and watching its companies give their final pitches. At the end of each pitch, the presenters followed the same pattern. They’d show a slide announcing how much money their companies were raising — their “ask” — and then they’d flip to another slide describing their “use of funds.”

After the fourth or fifth time this happened, one of the VCs seated in front of me leaned over and whispered to the person next to him: “They keep telling us how they’re going…

I opened my inbox in the morning and found an email from an entrepreneur asking a question about pricing. Later that same morning, I had coffee with a founder also struggling with pricing. After that, I met another founder for lunch who spent the entire meal peppering me with questions about pricing. That was a weird coincidence, I thought as I left lunch. Three entrepreneurs… three pricing issues. …

Entrepreneurs are, by definition, excited about their newest startup ideas. It’s what motivates them to build their businesses. But all that excitement and motivation also creates a unique challenge. Because they’re so excited, entrepreneurs tend to assume everyone else is equally as excited, and, as a result, they often start obsessing about other people stealing their startup ideas.

This is exactly what happened to an entrepreneur named Lane Merrifield when he first launched a revolutionary online community for children called Club Penguin. Yes, he’d eventually sell it to Disney for $350 million. …