Meet Evan Bellingar

We were lucky to catch up with Evan Bellingar recently and have shared our conversation below.

Hi Evan , so happy to have you with us today and there is so much we want to ask you about. So many of us go through similar pain points throughout our journeys and so hearing about how others developed certain skills or qualities that we are struggling with can be helpful. Along those lines, we’d love to hear from you about how you developed your ability to take risk?

There was no official recession declared in 2023 or 2024, but for me and my business: we were in a terrible spot. In late 2024 I had been retired for almost a year having left a stable, good paying job after years and years of nothing but economic success. The graph of my net worth that I WAY too obsessively updated just went up month after month and year after year until I retired, and now it felt like it was in freefall. I retired from my dayjob because my wine brand needed attention, my long term rentals were doing great, and we now had 4 short term rentals. Then the hits started coming: huge repair bills, higher interest rates meant that we couldn’t get cash out at refinances anymore, short term rental rates went down and vacancies went up. Selling grapes into the worst market in 20 years didn’t happen, and wine tasting tourism was down 30 percent. The tailwinds that had propelled my success turned to headwinds, all at once, and didn’t care that I considered myself “a good businessman” or “I’m good with money”. Add in a looming IRS bill that I had no idea how I would pay for, and it was a low point. It took me awhile to realize, but the pain I was feeling wasn’t from the loss of the money, it was from the loss of identity. Part of my identity was “Evan Bellingar: growing real estate investor” “Evan Bellingar: wealthy and getting wealthier” “Evan Bellingar: wine salesman” and when those things weren’t happening, it was like a part of me dying. Peak to trough, my net worth went down almost 25% in a little over a year, and while that might not seem like much, I sure felt it when I couldn’t sleep.

This essentially forced me to take one of the biggest risks of my life: to start the vineyard management company Century Vineyards. I had to create an income to undo the damage the last year and a half had inflicted.

One of the quotes that pivoted my life if from Machiavelli, who isn’t often quoted in the personal development space 🙂

“all courses of action are risky, so prudence is not in avoiding danger (it’s impossible), but calculating risk and acting decisively. Make mistakes of ambition and not mistakes of sloth. Develop the strength to do bold things, not the strength to suffer”

That has meant a lot to me. “not the strength to suffer”. Tough guys can be too tough: accepting the situation for what it is because we are tough enough to take the punishment. It’s going to take courage and strength and money anyway, why not use those resources trying for something new, great, and exciting?

Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?

I am deeply embedded in the Oregon Wine Industry. I spent 20 years managing vineyards for others, which is a really interesting, high paced way to get involved in agriculture. I didn’t come from a farming background, so having an onramp to agriculture was important. My wife and I have been investing in rental real estate since 2012, and we started our wine brand Bellingar Estates in 2014. In late 2024 we launched Century Vineyards a full service vineyard management company in the North Willamette Valley.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

“Google it”
I always assumed my wife Kim was great at Excel because she had taken a class in college on it, because she was always so effortlessly great at creating beautiful spreadsheets. One time I asked her where she learned it and she said “when I don’t know how to do something I just google it”. Constantly learning new things, finding new solutions, staying curious about the world makes you a much more skilled person and a more valuable employee.

“make people money”
In any industry: figure out how the money flows, how people get paid, what the basic KPIs are, then put your efforts into those key areas. If you are making your company money and making your boss look good your earning potential goes way up. The opposite is also true: if you are seen as costing people money by trying to cut someone’s commission they won’t send you leads.

“at least she’s cheerful”
At some long ago dinner the server was doing a terrible job: the food was late, the orders got mixed up, and nothing was going right. My dad was complaining to the family but my mom uttered the now famous line: “well, at least she’s cheerful”. The server kept a positive attitude, did her best in a bad situation, and got a nice tip when it was all done. Being capable is great. Being capable AND cheerful and a pleasure to work with is a super power.

Any advice for folks feeling overwhelmed?

“Zoom out”

I’m embarrassed to even write this because it sounds dumb, but when I am overwhelmed I imagine there is a camera looking down at the top of my head, like a drone shooting a video of me. Then the camera slowly rises and the image in my head zooms out and I see the building, the surroundings, the area. Once I am a small spec in the mental image I ask myself “what do you think this guy’s next move should be?” That tiny reframe changes the way my brain interacts with the problem and makes it instantly obvious what I should do next. When you’re watching a movie you know exactly what the main character should do for the best outcomes. It is obvious and instant. How can I be the main character in the movie of my life?

“Write it down”
If I am overwhelmed by something, I journal about it. Something about writing the thing down adds perspective and changes the problem into something I have the power to solve.

Contact Info:

• Website: https://centuryvineyards.com
• Instagram: @bellingarestates

Image Credits

Evan Bellingar