Every entrepreneur knows that most startups fail, but very few of them actually understand why. — I was three years into running a venture-backed tech company that was doing all the things venture-backed tech companies are supposed to be doing. We had a product people loved, we had a rapidly growing user base, and we’d raised a few million dollars worth of investment capital. Sure, we…

As a consumer, you probably hate it, but, as an entrepreneur, you’ll love it — My first startup mentor wasn’t the most ethical entrepreneur in history. He built his fortune in the early days of the Internet by running affiliate marketing campaigns. While I realize that might not seem particularly nefarious, you have to remember that early online marketing was much less regulated than it…

Are you prepared to face the first obstacle of the Entrepreneur’s Journey? — I’ve always thought entrepreneurs are like superheroes. Not in a narcissistic or self-aggrandizing way. I don’t mean we’re saving the world. I just mean that the journey of a successful entrepreneur is very similar to the journey of a hero. To understand what I mean, let me start by explaining…

You might be stressed about hiring the right employee #1, but you should be more worried about employee #10 — It’s easy to make a big deal about the challenges founders face trying to hire their first employees. After all, that’s when startup founders have the least experience with hiring, so it’s also when they’re most likely looking for advice. In other words, if I’m a startup guru trying to…

If you’re tired of all the jargon about the next phase of the Internet, here’s a better explanation — If you’re like me, you’ve heard lots of people talking about Web3, but you’re still not exactly sure what it is. Depending how curious you are, you’ve read a handful of articles and/or watched a few YouTube videos explaining the concept. They likely feature a number of buzzwordy terms like…

Every entrepreneur is doing it wrong — Every fundraising pitch I’ve ever given for every startup I’ve ever tried raising money for has begun with some sort of explanation about my company’s product and what it does. Every… single… one. Beyond that, every fundraising pitch I’ve ever seen — which, at this point in my career, numbers…

It’s not necessarily bad, but I promise it’s not what you think. — My 75-year-old mom was coming to town for a visit. She lives a few states away. But, rather than flying (like a normal person), or driving (like a cheap person), she decided to take the train. The decision didn’t make much sense to me since she was spending as much…

Entrepreneurs are so busy chasing billion dollar valuations that they’re missing out on an even bigger opportunity — In the startup world, the word “unicorn” is used to describe private companies with billion-dollar-plus valuations. The description is meant to evoke a sense of rarity, but I’m not convinced it’s entirely accurate. After all, unicorns don’t actually exist and billion dollar, private companies do. …

Maybe the strategy entrepreneurs love using to improve their products isn’t so great — If you’re an entrepreneur trying to improve your product, the most valuable resource you have should be customer feedback. After all, having existing customers tell you what they like and don’t like about your product should be exactly the info you need to make things better. They’re the people who…