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…

Every entrepreneur makes it when they’re first trying to raise capital — “I’m about to ask a stupid question,” I said to a room of startup founders. I’d been invited by a local startup accelerator to give a presentation about fundraising to their newest cohor, and I wanted to keep the mood lighthearted. “Are you ready? …

Are you too distracted by your startup’s product to recognize what’s really going to drive sales? — I was walking my dog past a neighbor’s house and noticed a new “for sale” sign in the front yard. The house was being sold by a real estate agent named Ray, who, according to the photo on the sign, was a cocky looking 30-something with a creepily-small goatee and…

It’s more expensive than you think — I’ve got a friend who’s in an on-again/off-again relationship with a woman he’s been dating since college. It’s a never-ending source of drama for him, but a wonderful source of entertainment for me. Unfortunately, it’s also a constant reminder of my own tumultuous relationship. The relationship isn’t with my wife…

The typical structure for pitch decks doesn’t make any sense — “I never trust anything entrepreneurs say during their pitches.” That’s an actual sentence a venture capitalist said to me. And he didn’t say it during casual conversation or while feeling unusually candid over a nice glass of scotch. …

Everyone’s favorite cliche might not mean what you think — On the first day of my entrepreneurship class at Duke, I always begin by asking students the following question: How would you describe an entrepreneur? The first answer is almost always: “Someone who thinks outside the box.” If it’s not the first answer, it’s the second answer. “So you’re saying…

One you know, but you’re probably overlooking the other — I was tinkering with a potential startup idea and trying to figure out whether it was worth pursuing. To do so, an angel investor I was friendly with helped me schedule a handful of intro meetings with companies that might be good customers. The meetings had been going well, and…

People will buy anything if you can figure out the right sales pitch — I walked into my entrepreneurship class at Duke University, dumped a bag of Jolly Rancher candies on the table, and said: “You have an hour to sell one of these Jolly Ranchers for $100. Go!” For those who don’t know what Jolly Ranchers are, they’re small, rectangular, fruit-flavored hard candies…

Investors aren’t always great at telling founders what they’re really thinking. — When I was in college, and long before I imagined being an entrepreneur, I took a class called “Dictionaries and Their Makers.” I thought it sounded interesting. Turns out, I was wrong. To nobody’s surprise except, probably, my own, a class about how dictionaries get made was not an interesting…