When I was first learning to fundraise, I believed I needed to convince investors of two things: 1) that my startup was awesome; and, 2) that I was an exceptional entrepreneur. In my mind, the best way to accomplish those two things was by learning how to give a perfect fundraising pitch.

I read countless articles about how to pitch investors. I spent hours practicing my pitches in front of trusted mentors. I even recorded myself giving my pitch, then I would dissect the videos like a golfer who records his swing then analyzes it for flaws.

Thanks to all…

So you want to be an entrepreneur, huh? You’ve watched a few movies about people like Steve Jobs and Mark Zuckerberg. You’ve been reading Techcrunch religiously for years. And you’ve carefully studied every fundraising article on Medium. The only thing left to do is keep brainstorming until you come up with your world-changing idea.

It’s a flawless plan. Well… almost flawless. It overlooks one important detail: that’s the “fake news” way of becoming an entrepreneur. Sure, I suppose it could be possible. You could be a “visionary” who — through sheer force of will — thinks up an incredible opportunity…

By now, most people already know Facebook and its CEO, Mark Zuckerberg, are hell-bent on capturing user data and making money off of it (the subject of at least two popular documentaries about it on Netflix). And now, in a bold demonstration of force, Apple CEO Tim Cook has come charging in atop his noble white steed (also available in Space Gray™ and Rose Gold™) to protect consumers. …

From an entrepreneurial perspective, enormous markets have an obvious advantage: The more potential customers you have, the bigger your company could become. And, of course, we see this play out all the time. For example, everyone in the world wears shoes, meaning the shoe market is enormous. As a result, companies like Nike and Adidas are some of the largest in the world.

The corollary to this is that enormous markets have lots of competition. In the case of my shoe companies example, Wikipedia lists 388 different shoe companies worldwide. And that list is nowhere near exhaustive. …

When I was a young entrepreneur first learning to build startups, an early mentor gave me a piece of advice about sales that seemed ridiculous at the time. Then I actually tried it and was amazed by how well it worked.

I still remember our conversation. We were sitting in a coffee shop in Philadelphia and I was complaining about a potential customer I’d spent hours trying to close. The prospect backed out of the deal at the last minute because it “wasn’t what they really needed.”

“No matter what I said, I couldn’t convince her to change her mind,”…

“Coronavirus is the black swan of 2020.” So began the ominous letter that venture capital firm Sequoia Capital sent to the founders and CEOs of its portfolio companies on March 5 of last year. In many ways, the note was prescient, published roughly a week before the rest of white-collar America shuttered their doors and pivoted to remote work.

I remember receiving a similar pandemic-panicked email in my inbox around the same time as the Sequoia note. It essentially declared: “Nobody is allowed to come into the office until further notice.” I was in a meeting with approximately 20 other…

When building startups, entrepreneurs focus almost exclusively on the needs of their target customers and how to best help them. And why wouldn’t they? After all, if, for example, you were building an app to help parents coordinate their children’s after-school schedules, why would you spend any time thinking about non-parents? Or if you were developing a device to help diabetics manage their condition, why would you spend any time thinking about non-diabetics?

In general, this kind of myopic focus on the people in your target market and their needs is necessary because it helps entrepreneurs make important business decisions…

Since you’ve clicked on an article that’s clearly intended to give advice about pitching investors, I’ll wager this isn’t the first time you’ve read an article containing fundraising advice. That’s great! If you’re an entrepreneur thinking about taking investment, you should be researching the fundraising process. You’d be a fool not to.

However, most fundraising articles — including many of my most popular articles — tend to have the same flaw. They often treat “investors” as a monolithic group with the same expectations, ambitions, and strategies. …