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…

Most people don’t even realize the problem until it’s too late — The first startup I ever built was the type of company that people in the entrepreneurial community usually describe as the “hardest type of startup.” It was a two-sided marketplace. Two-sided marketplaces are considered the hardest types of startups because founders need to solve the “chicken or the egg” problem…

Only one type of customer buys magical products, and it’s probably not the one you’re selling to. — A founder I was meeting with was pitching me his startup’s product. His value proposition seemed incredible. …

Even if you don’t want to be TikTok famous, good entrepreneurs need to know how to reach more people. — I stirred up a little controversy a few weeks ago by publishing an article where I argued that Walt Whitman — a famous 19th Century poet — was, in his era, the equivalent of a modern day TikTok influencer. At the end of the article, I suggested this framing of…

Hint: It’s the same reason most founders prefer working by themselves — One of the most sacred “rules” across the startup investing world is that investors don’t invest in solo founders. Sure, there are occasional exceptions, but the exceptions are rare and always have good reasons for having happened. For example, VCs occasionally invest in random solo founders who somehow manage to…

You’ll be surprised by the kind of research it requires — As anyone remotely involved in the startup ecosystem understands, investing in startups is extremely risky. Simply put, most people would be better off going to Vegas and playing blackjack than writing a check to an entrepreneur. However, as we also know, big risks have equally big rewards, which is why…

It’s never what they think — I was meeting with a recent college graduate who’d just moved to my city and was looking for opportunities to get involved in the startup ecosystem. He was, according to him, planning to launch his own company soon. In those situations, I always like to learn more about why someone…

Every entrepreneur should understand the consumer purchasing process as well as scammers — I hate scammers as much as the next person. However, as someone who studies and teaches entrepreneurship, scammers also impress me. After all, being a successful scammer requires developing a sophisticated understanding of the consumer purchasing process so you can know how to exploit it. In contrast, entrepreneurs often misunderstand…

One of the biggest threats to your startup isn’t unique to entrepreneurship — Shakespeare is largely regarded as one of the greatest writers in Western Literature. Some people even argue he does such an incredible job depicting the emotional, social, and infrastructural foundations of our world within his plays that he basically invented the modern human. To be fair, the people making that…