Experience does not guarantee immunity from failure; seasoned founders often repeat the same errors. Repeated business cycles show that entrepreneurs convince themselves that different circumstances — more capital, a new vertical, economic shifts, or better advisors — will change outcomes, but fundamentals remain constant. Common failures persist unless founders deliberately recognize and avoid them. Intelligence can cause overcomplication, leading to unusable solutions such as an onboarding flow requiring five-step identity verification, AI scoring and multiple user roles. Technically perfect systems can fail when customers cannot complete basic interactions. Preventing these mistakes requires simplifying solutions and focusing on fundamental user needs.
After buying, building, burning and selling businesses ranging from $1 million to over $20 million in annual recurring revenue, with teams as small as five and as large as 500, I've seen these mistakes up close. Not once. Not twice. But over and over. I've made them myself. I've watched peers make them. And most frustratingly, I've watched incredibly smart entrepreneurs make them while fully aware of the warning signs.
Because we convince ourselves that this time is different. We raised more capital. We're in a new vertical. The economy has shifted. We've got better advisors. But these so-called differences rarely change the fundamentals. These mistakes don't care about your funding round, your pitch deck or the decade you're building in. They always find a way to show up ... unless you deliberately learn to recognize and avoid them.
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