Category: Domain Investing Regrets

Every cycle in domain investing brings with it a wave of urgency. A new technology emerges, a new acronym floods headlines, venture capital shifts focus, Twitter threads multiply, and suddenly the market feels as if it has tilted in a new direction. Artificial intelligence, crypto, NFTs, Web3, quantum computing, metaverse, biotech, green energy, decentralized finance.…

At some point in almost every domain investor’s journey, diversification begins to sound like sophistication. You start with .com, as most do. Then you add a few strong country code domains. Then perhaps some short .io names because startups seem to like them. A couple of .ai domains because artificial intelligence is booming. A handful…

There are few moments in domain investing that feel as quietly humiliating as paying a redemption fee for a domain you never intended to lose. Not because the amount is catastrophic in isolation, but because the entire situation was preventable. Redemption fees do not represent strategic risk or market miscalculation. They represent administrative failure. They…

The most expensive mistake I made in domain investing was not a single bad auction, not a missed renewal, not even a domain I let drop too soon. It was something quieter and far more foundational. I started spending real money before I understood how to value what I was buying. In the beginning, everything…

There is a special kind of regret in domain investing that does not reveal itself at checkout. It waits patiently. It hides behind surface metrics. It disguises itself as opportunity. Buying a domain with a toxic backlink profile is not the kind of mistake you notice immediately. It is the kind that unfolds slowly, as…

There is a phase in domain investing where acquisition feels like progress. Every new name added to the portfolio represents potential. You refresh auction lists daily. You scan expired drops. You evaluate closeouts at midnight. Each purchase feels like planting a seed that will eventually grow into a sale. The portfolio expands steadily, and with…

There is a unique kind of regret that comes from acting too soon in the name of caution. In domain investing, timing is everything, but patience and nerve often matter more than speed. One of the most painful lessons I ever learned was not about overpaying for a domain or missing a drop by seconds.…

There was a period in my domain investing journey when a single number could influence my decision more than comparable sales, more than intuition, more than market context. That number came from an automated appraisal tool. I would type in a domain, wait a few seconds, and a clean, authoritative-looking valuation would appear on the…

There is a particular kind of regret in domain name investing that does not arrive immediately after a purchase but settles in slowly, like a dull ache that intensifies with time. It begins with excitement, escalates with competition, and ends with a confirmation email that feels triumphant for a few brief minutes. Then the numbers…

In domain name investing, adaptability is often praised as a competitive advantage. Markets shift, technologies evolve, buyer preferences change, and new extensions enter the landscape. It is sensible to remain flexible. But flexibility without consistency becomes drift. For a long stretch of my investing journey, I changed strategy almost every month. One month I focused…