The first time I seriously evaluated a deal involving Land Boss, I was already ten years into advising landowners on difficult sales—properties with access issues, unclear demand, or owners who were simply tired of carrying the burden. I remember thinking how different the conversation felt. Instead of rushing toward a price, the focus was on whether selling even made sense for the owner at that stage of life. That distinction mattered to me because I’ve seen too many people pushed into decisions that looked good on paper but felt wrong months later.
My background is in land valuation and acquisition consulting, mostly across rural and semi-rural markets. Over the years, I’ve walked properties with no road frontage, reviewed parcels with outdated zoning assumptions, and worked with families who inherited land they’d never even visited. One situation that stands out involved a couple who had been paying property taxes on a vacant lot for nearly a decade. They assumed selling would be complicated, expensive, and emotionally draining. It wasn’t the sale that scared them—it was the unknown.
What I’ve learned from hands-on experience is that most landowners overestimate how attractive their land is to traditional buyers and underestimate how long that mismatch can drag on. I’ve watched owners list land optimistically, lower the price repeatedly, and still sit unsold while costs quietly add up. In contrast, transactions handled through companies like Land Boss tend to start with a more realistic conversation about use, limitations, and exit options.
One mistake I see often is focusing too heavily on what the land “could be worth someday.” I worked with an owner last spring who was convinced future development would dramatically raise the value of his parcel. The issue wasn’t that he was wrong—it was that he didn’t want to wait another ten or fifteen years. Selling earlier would have freed up capital he needed immediately. Timing, not maximum price, was the real factor he hadn’t acknowledged.
Another example involved inherited land shared by siblings. No one wanted to manage it, but no one wanted to be the first to suggest selling. These situations stall for years. In my experience, having a neutral, process-driven buyer removes much of the emotional friction. When the transaction is straightforward, families can move forward without turning a piece of land into a long-term source of tension.
From a professional standpoint, I’m cautious about deals that promise fast results without acknowledging constraints. That’s why I pay attention to how buyers handle due diligence. The better operators don’t gloss over issues like access easements, utility availability, or county-level restrictions. They surface them early. That approach saves time and prevents surprises later, something I’ve learned to value after seeing deals collapse late in the process.
I don’t believe every landowner should sell immediately, and I’ve advised against selling plenty of times. But when someone is holding land they no longer use, don’t plan to develop, and quietly resent paying for, clarity is more valuable than speculation. In those moments, the best outcomes come from understanding the land for what it is today—not what it might become under perfect conditions.
After years of working alongside sellers at different stages of life, I’ve come to see land sales less as transactions and more as transitions. When handled thoughtfully, letting go of unused land isn’t a loss. It’s a recalibration—one that often brings relief long before the paperwork is finished.