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…

You don’t have to like broccoli to appreciate the entrepreneurial wisdom of the broccoli industry. — I launched a new startup last week, and someone immediately told me he doesn’t like my idea. According to him, it’s a: “Bad idea — [what you’ve built is] part of Gmail and many other [emailing platforms] or can be done with a simple automation script.” When I was a…

Sending high-quality emails is the best way to get investors interested in your startup — A few years ago, back when I was still regularly fundraising for my own startups, I had what may have been, in retrospect, a stupid idea. I decided I could get better at emailing investors if I knew what it felt like to receive emails as an investor. To accomplish…

Sure, a machine apocalypse sounds scary, but that doesn’t mean it can’t be fun, too! — The “Singularity” — the supposed moment when technology growth becomes uncontrollable and overtakes humanity — was never something I personally worried about. While lots of people’s jobs and livelihoods seemed at obvious risk of being co-opted by machines, mine never did. For example, I’m not a truck driver, so automated…

Do you know the best way to avoid having the same experience? — I just launched a new startup. Before explaining anything else, I promise this article isn’t an attempt to sell you something. I’m not going to link to my startup. I’m not even going to tell you my startup’s name because I know, if I do, you’re going to think this…

Lots of people make intros, but do they always know the right way to make them? — When I first began teaching entrepreneurship nearly a decade ago, I remember one of my students showing me an app he’d built and I had no clue what to tell him. I didn’t know much about his market, and I didn’t want to give him bad advice, so I made…

And you can judge if a startup advisor is worth having simply based on whether or not they take it if you offer. — A founder I’d been working with for years was finally starting to get good traction with her startup. As part of that traction, and, I suppose, to show appreciation for my years of helping her, she offered a small piece of free “advisor equity.” “No thanks,” I said. “I can’t…

And it’ll probably be the best $1,000 I’ve ever spent. — Experienced entrepreneurs are constantly telling new entrepreneurs: “Ideas are worthless. Execution is what matters.” Heck, I lectured thousands of readers right here on Medium about this very issue in a recent article lamenting how frustrated I am by all the young entrepreneurs who keep asking me to sign their ridiculous…

And you don’t have to become TikTok famous to take advantage of what’s happening. — Entrepreneurs are always noticing interesting startup opportunities. It’s not because we’re all constantly trying to start new companies. Instead, it’s more of a habit or reflex… a sort of opportunity “spidey-sense.” When it hits us, we can’t help but think, “What’s the opportunity here, and how can I get myself…