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…

Identifying which founders are good investments is easier than you might think. — Entrepreneurs tend to think investors are too arbitrary in the ways they make their investment decisions. Or rather, that’s how I often felt after being rejected by a VC I was sure would love my pitch. “They just don’t get it,” I’d tell myself when VCs didn’t offer a term…

Entrepreneurs do lots of different jobs in their companies, but only one skill truly matters. — I was speaking with a group of young founders. One of them raised his hand and asked, “What kinds of things are entrepreneurs good at?” “All kinds of things,” I answered instinctively. “Entrepreneurs usually work in very small teams, and they don’t have lots of coworkers. Because of this, entrepreneurs…

Lessons from two decades of serial entrepreneurship — I was giving a presentation to a group of entrepreneurship students at a nearby university. As I was sharing the story of my personal entrepreneurial journey, I mentioned I’d launched my first startup when I was 20. Since I recently turned 40, it meant I’ve reached the point in my…

Once you know the right strategy, selling stuff isn’t nearly as hard as most entrepreneurs think. — Every year for the past seven years I’ve given students in my Duke entrepreneurship class the same impossible challenge. I hand each of them a Jolly Rancher — a 5 cent piece of hard candy — and I ask them to sell it for $100 in an hour. Not surprisingly…

What if losing all an investor’s money isn’t as bad as most entrepreneurs think? — One of the worst parts about raising venture capital for your startup is that it nearly guarantees an incredibly awkward conversation at some unknown point in the future. That conversation is going to be with an investor after you’ve lost lots of that person’s money. I realize most entrepreneurs aren’t…

Lots of entrepreneurs are still building startups like it’s the 20th century. — A well-known entrepreneur was in my city giving the keynote at a local tech conference. Since I teach entrepreneurship, I offered my students extra credit for attending. I wish I hadn’t. His advice was terrible. The entrepreneur was from an older generation. Not that being old inherently means a person…

The rules of a classroom aren’t the same as the rules of a startup. — The most valuable entrepreneurial skills are rarely directly teachable. Instead, they tend to be things people learn indirectly while they’re busy doing other things… like while cheating in school. For example, consider one of my close friends who’s currently launching a medical devices startup. He’s writing a grant proposal (lots…

Some thoughtful early planning can lay a great foundation for creating the kind of businesses other companies want to buy. — A venture capitalist I’ve been friendly with for a while was in town attending a board meeting of one of his portfolio companies. Having heard about his pending trip, I invited him to speak with my class of Duke entrepreneurship students. At first, nothing the VC said was particularly unusual…