06/01/2026
Twenty years ago today—June 1, 2006—the deal closed on a property that most people thought I was crazy to buy.
That purchase was an extension of how I operated. A few years earlier in the Okanagan, I had arrived late to a garage sale, and by the time I got there, everything was gone. I decided to ask the owner if the house itself was for sale. He said yes, we agreed on a price, and we wrote the contract on a paper towel with a black sharpie. It was a late Saturday evening so we went to the ATM and I took out cash for a deposit on the house and handed it to this stranger.
The story for this farm almost is a repeat of the house purchase. This time though I had a real estate agent. My real estate agent called to tell me a property was about to be listed for sale. By then, I had already spent a year searching for the right site. I had narrowed down the areas in the valley capable of growing world-class Pinot Noir and had done the math, using environmental lapse rates and growing degree day data to compare potential sites here against some of the best Pinot Noir regions in the world—from France and New Zealand to Oregon. I had already spent a significant amount of time on the South Island of New Zealand, looking at world class Pinot Noir vineyards.
When we arrived at the property, the agent drove me down the driveway and pointed out the property boundaries. I didn't even bother getting out of the vehicle. I knew right then I was going to buy it. I said I will buy it. We went back to the office, wrote up an offer, and the next day the offer was accepted. I had no idea how I was going to pay for the farm.
I had to leave town for work, so I withdrew the down payment in cash and dropped it off at the agent's house in a brown paper bag, on my way out.
To everyone else the property, looked like madness. I had just offered the highest price per acre the region had ever seen. People thought I was crazy.
I had also left a very good job a year earlier with the Mark Anthony Group, Mission Hill Family Estate in the Okanagan, to bet on an unproven wine region.
At the time, Skimmerhorn hadn't even opened yet—they had only recently planted their vineyard.
The property itself was far from impressive. It was a fragmented, neglected orchard that wasn't even fully planted. Christmas trees grew between rows of peaches. At the top sat what I came to call the "graveyard"—a hillside buried under decades of scrap wood, forgotten yard sale items, rusted-out vehicles, and more Christmas trees.
But I wasn't looking at what it was. I was looking at what it could become.
The next twenty years were anything but easy. Irrigation was replaced, new trees were planted, tractors, sprayers, mowers and implements were purchased, and slowly the farm transformed from the top down.
Once the upper ground was finally cleared, it became a high-density, high-elevation vineyard. That was the beginning of a new chapter for the farm.
Today, with irrigation running and vines thriving at the top of the hill, new pears trees and apple trees at the bottom, the gamble feels less like a risk and more like a necessary leap.
This year, there are more grapes being planted where the last peach trees were lost in the 2024 freeze.
What's interesting is that the company I left twenty years ago is now my neighbour. Back then, many people thought I was crazy for buying land to plant grapes in this region. Over time, others saw the same potential and followed.
Twenty years later, I'm reminded that the best investments rarely look perfect at the start. Sometimes they're overgrown, neglected, and buried under someone else's leftovers.
The Impossible just takes longer, or Time Will Tell.