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…

Learning to structure your pitch around this one question is the key to raising capital. — A founder came to my office looking for advice about fundraising. The first thing he did once he’d sat down was begin telling me about his product. After about five minutes, I interrupted to explain that I understood what his product did (it wasn’t a particularly complex product), and I…

Raising venture capital gets easier when you understand what VCs prioritize. — “I’m going to start raising money for my startup,” a student explained as she chatted with me at the end of one of my entrepreneurship classes. “You mentioned you’ve raised money for startups in the past. …

If ChatGPT is showing us anything, it’s that most entrepreneurs are wildly confused about what startups are actually supposed to do. — The entrepreneurial world is always salivating over the “next big thing.” One year it’s iPhone apps. The next year it’s big data. Then it’s augmented reality. Then virtual reality and the metaverse. Crypto. NFTs. Now we’re in the AI hype machine. …

The most valuable startup lessons are never learned in a classroom. — Ask new entrepreneurs the most important factor in determining a startup’s success, and they’ll almost certainly talk about having great products. However, ask successful entrepreneurs the most important factor, and they’ll almost certainly discuss customer acquisition. Experienced entrepreneurs are constantly trying to explain this distinction to new entrepreneurs, but most…

Most entrepreneurs have no clue what venture capitalists actually care about when listening to fundraising pitches — I was invited to speak at a startup panel about fundraising, and, by some strange coincidence, I found myself sitting next to the first venture capitalist I ever tried to raise capital from. I couldn’t help but chuckle at the situation. There I was, in front of a room filled…

Medium is tweaking the rules authors need to play by in order to get readers, and that might make this place feel a lot more like TikTok. — Dear Tony Stubblebine and the Medium Team: I’ve read your updates that Medium is going to start heavily prioritizing comments (“replies” in medium parlance) when it decides whether or not to recommend articles to users. When the news came out a few weeks ago, I wasn’t particularly bothered by it…

Entrepreneurs can learn a lot from one of the most successful companies in history. Just make sure to learn the right lessons. — “I’m building Amazon for the travel industry,” an entrepreneur told me as we sipped coffees. He was in his early 20s, and, technically, he didn’t say he was building Amazon for the travel industry. His vision involves a completely different industry, but he’s still working on his startup, so I…

This simple framework can help you learn to give a perfect pitch every time. — A buddy of mine runs a startup accelerator. He recently invited me to speak to his cohort and meet, individually, with its 12 current companies. Despite the fact that both my buddy and I explicitly explained I was there as a startup advisor and not an investor, all but one…