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…

Are you staying focused on the right things? — An entrepreneur stopped by my office, excited to share the idea he’d been working on. The idea was for an online, buyer/seller marketplace. These types of two-sided marketplaces are immediate “red flags” to experienced entrepreneurs because two-sided marketplaces face the notorious “chicken-or-the-egg” problem — you need sellers in order to…

A successful startup isn’t necessarily a startup you’ll enjoy building — My first startup was in the events industry. Concerts, sporting events, broadway shows… those kinds of things. The startup was a miserable failure (a story for another article), but, in retrospect, I’m incredibly lucky it failed. If it had been successful, I would have spent years doing work I hated. …

Are you being an idiot during your fundraising pitches, too? — Humans have a funny habit of underestimating the things we don’t understand. For example, consider a sport like NASCAR. Lots of uninformed observers will ask, “How is that a sport? It’s just people driving in circles.” What those people don’t appreciate is that driving cars near the peak of their…

Are you ready for what’s coming next? — The concept of the garage startup comes from Silicon Valley culture. It’s a reference to the fact that some of the world’s most successful and iconic tech companies had their first headquarters in — you guessed it — garages. Examples of garage startups include companies like Apple, Amazon, Microsoft, Hewlett-Packard…

If you’re looking for an easy-to-follow pitch deck structure that’ll impress investors, here’s what you should know. — The Internet is flooded with videos, articles, and presentations teaching entrepreneurs how to create the “perfect pitch deck.” Back in my younger startup days, when I encountered those types of tutorials I would treat them almost like sacred texts. …

Even the simplest questions can have unexpected implications — I was hosting a venture capitalist as a guest speaker in my entrepreneurship class at Duke. During the Q&A session of his talk, one of my students asked the following question: “What’s your favorite question to ask entrepreneurs when they’re pitching you?” Even if I didn’t know his exact answer…

If you’re busy building a product, you could be missing out. — When most people think about entrepreneurship, they think about building products. But products aren’t the only type of entrepreneurial venture. There’s another type of entrepreneurial opportunity that’s incredibly lucrative, but, historically, it’s been nearly impossible to successfully pursue. However, that’s changing in the 21st Century.

You’ll become better at fundraising once you’ve learned how to pitch the right investors — Startup founders who’ve successfully raised venture capital tend to share the number of investors they’ve pitched like it’s a badge of honor. Even if they don’t know the exact number, they’ll happily remind you of how many times they heard “no” before getting a “yes.” On some levels, I appreciate…