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…

Uber-talented people make crappy business partners — My first co-founder used to describe everything I produced as “half-assed.” He thought I was sloppy and had too much of a tendency for cutting corners. The code I wrote for our software was never clean enough. The marketing emails I drafted were never compelling enough. My fundraising pitches were…

Sometimes the people we love most are best at helping us see our faults — I used to treat my startup like it was the only thing that mattered in life. If I was awake, I was either working on my startup or annoyed I was doing something that prevented me from working on my startup. In retrospect, I’m not sure if that kind of…

Things that sound good aren’t necessarily true — Myths are a type of technology. I realize most people don’t think of them that way because myths don’t have screens or batteries or user accounts. But, for the sake of understanding my point, let’s pretend to teleport ourselves back 3,000-ish years and imagine living in two different parts of…

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? Do you promise not to laugh…

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…