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…

Investor rejections are more thoughtful than most entrepreneurs realize. — Back when I was fundraising for my startups, I noticed a pattern in the way venture capitalists ended meetings. If they weren’t interested in investing, they’d always end meetings by saying something along the lines of, “I’d love to follow your progress. Keep in touch!” The first time I heard…

Money is tight for startups, but that doesn’t mean you shouldn’t spend it when the right opportunities come along. — I’ll never forget the first “big” purchase I made as a startup founder. My longtime co-founder and I had just launched our new startup together, we were in our early 20s, and we’d been given a whopping $25,000 to participate in a startup accelerator program. To be fair, $25,000 isn’t…

Is the artificial intelligence revolution about to fizzle? — Are you worried about ChatGPT taking your job? Me too! After all, writing is a huge part of my job, but, in the time it takes for you to reach the end of this sentence, ChatGPT can spit out 2,000 coherent and compelling words about the exact same topic. Clearly…

A successful round of fundraising can take your startup to the moon, but do you understand all the costs? — One of my closest friends recently told me he and his wife are expecting their first child. When he shared the news, I did exactly what everyone does: I put on a huge smile and excitedly said “CONGRATULATIONS!” as though I’d just been told the most amazing news in history. …

This childish mistake that lots of entrepreneurs make can have big consequences. — “I don’t understand,” I said to the founder sitting across from me. “What problem are you trying to solve?” This particular founder was part of an important segment of the entrepreneurial community building socially conscious, sustainable ventures. In his case, he was building a non-profit that collects expiring food from…

Great pitch decks are like works of art. Are you ready to become a pitch deck artist? — A friend had just returned from a vacation to Paris. He was telling me about his visit to the Louvre, and he mentioned his thoughts on the Mona Lisa: “The room where it hangs is really crowded.” “The painting is much smaller than I thought it’d be.” “I don’t really…

They’re skills you won’t learn about from a book, Google search, or ChatGPT. — I was hosting a panel of startup founders at an entrepreneurship conference, and we’d reached the Q&A section. A woman in the audience stood up and asked the four panelists the following question: “What was the most unexpectedly valuable skill that helped you succeed as entrepreneurs?” The answers from the…

If investors aren’t responding to your meeting requests, this is probably the reason. — A founder I was chatting with at a startup networking event asked if I’d be willing to meet with him and discuss his venture in more detail. “Of course,” I told him. “Send me an email and we’ll schedule a time to talk.” A few hours later, I received his…