A Shark Tank investor with $200 million in real estate says his first question on any purchase has nothing to do with the numbers.
Herjavec turned down a $65 million offer on his Yellowstone Club home. He's moving back to California despite his financial advisors raising an eyebrow. He converted a racquetball court into a climbing wall for his kids. None of these are the financially optimal decisions. All of them are the right ones for where he is in life.
Coming from a professional dealmaker, that's a meaningful distinction. When it comes to personal real estate, the calculus is completely different. The spreadsheet takes a back seat. The question becomes where do I want my kids to grow up. Where do I want to spend summers. What will I actually remember.
I see this regularly in Aspen. The buyers who lead with conviction, who buy the home they love rather than the home that checks the most boxes, tend to be the most satisfied. Love what you buy, and you're probably not alone in that opinion.
The experience you defer while waiting for a better deal has a cost that doesn't show up on a spreadsheet.
