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Friday Entrepreneurs: Courtney Kingston, Kingston Family Vineyards

Ramit Sethi

Here’s a fun interview I did with Courtney Kingston, who runs a vineyard (not your typical web business). She went from being in a senior position at an Internet company to starting this vineyard. “The hardest thing about pursuing a dream is that it isn’t convenient,” she said, which strikes me as enormously perceptive. How many times have you heard someone saying, “I’m just waiting for the right idea” or “I’ll start my own thing when I save up $50,000”? As I’ve written before, it never gets easier than now.

Courtney also told me that people might read this and think, “Well, I don’t have a family vineyard in Chile or an MBA from Stanford or a…” You’re right, you don’t. So what? I wrote about this in Success and the Shrug Effect, where I noted that we often point to someone successful, identify their qualities that we don’t share (“A Stanford MBA”), and then shrug, saying, “What can I do?” That’s BS–don’t fall for it. Everyone starts, whether it’s a paper route at age 12 or a vineyard at age…something more than 12.

My favorite part of this interview is when she identifies a huge problem that you’ll encounter when you’re doing your own thing: the fact that you have a million things to do with no structure whatsoever. Her solution? Sticky notes. Read on to find out what I mean.

What is Kingston Family Vineyards?
Kingston Family Vineyards is my family’s winery based in Chile’s Casablanca Valley. We specialize in hand-crafted Pinot Noir, Syrah and Sauvignon Blanc made from our hillside vineyards. All our wines are produced and bottled in Chile, and then I import them and distribute from my California office.

Ok, honestly. How often are you drunk?
Actually, I taste and enjoy a lot of wine (sometimes before 9am if I have an early tasting appointment with a restaurant) but sometimes the job is less ‘intoxicating’ than you’d imagine. If you think about it, you can’t learn very much about wine if you’re not sober enough to remember what it tasted like.

How did you get started running a vineyard?
My family always had this ranch in Chile. My dad was born there. But when I graduated from college in the early 1990’s, it was mostly dairy and beef cattle (and some great mountain biking trails up in the hills). The idea of starting a vineyard was my brother Tim’s and my idea. Back then I was working in high tech in the Bay Area. I liked my job and worked long hours, and gave it everything I had.

Plus it was good for my lifestyle—I was single, loved living in San Francisco, everyone I worked with was my age with similar interests. But as I moved up in the company, my job became a lot of directing/managing/helping others get their job done. I became somewhat like a well-paid traffic cop, but I no longer felt I was doing anything tangible myself. I also started to burn out from the long hours. When I turned 30, I decided I needed a lifestyle change where I could enjoy a more balanced life. That’s when I took the plunge and started working full-time on developing our wine business. And coincidentally I met my husband Andy just six months later.

How did you take that step of going from a safe job to doing something so unusual?
It was a tough transition. One of the biggest challenges for me was going from a job that was reactive (e.g. a highly scheduled day managing other people) to starting a business with a blank slate every morning. Every day, there were a thousand things that seemed urgent that I needed to do to get things going. It was a little paralyzing and I didn’t know where to start. My friend Rob gave me a great piece of advice: decide what *one thing* is critical to your concept’s success. Write “ONE” on a little yellow stickie, and stick it on your computer monitor as a daily reminder to accomplish one thing–no matter how small—that will get you one step closer to that goal each and every day.

For Kingston Vineyards, our biggest challenge in the beginning was finding a talented pinot noir winemaker who wanted to explore the new frontier of making pinot in coastal Chile. My “network” in Napa consisted of only two people when I started. And they weren’t even winemakers! But with that little yellow stickie reminder, every day I sifted through the thousands of urgent-but-not-important distractions to get one step closer to our goal of finding a winemaker.

What was some of the feedback you heard when you left your job?
On the surface, my work colleagues were encouraging, but I think they really thought I was nuts and believed they’d be interviewing me for an internet job within a year. While wine definitely has sex appeal, I was not pursuing a pre-IPO opportunity like everyone else was at the time. I left a job with 60 people on my team to go work by myself out of my San Francisco apartment. I cut my salary by more than half. I went from a known quantity—doing something I knew I was good at but that no longer challenged me—to something I wasn’t completely sure was going to work out.

I think most people thought I was taking a “break” rather than starting a real business. The hardest thing about pursuing a dream is that it isn’t convenient. Sometimes it’s more convenient to have your dream sitting on a shelf, neatly wrapped in a pretty package for you to look at from a distance., and always wonder “what if”. At least I could say I tried. I remember a professor of mine once saying “when you come to a crossroads, whatever you do, just don’t stop. Go right, go left, go straight. Whatever way you go…go forward.”

What are some of the interesting insights you’ve learned about doing business as a woman?
I can’t say doing business as a woman is harder, since I’ve never known anything else. I’ve had some challenges as a woman doing business in Chile, where the business culture is very male-dominated. Also, earlier in my high tech career, my straightforward/to-the-point approach was typical and expected. I was all about white boards and bullet points and optimizing the use of everyone’s time. And I was used to leading. Then there I was: a “gringa” in rural Casablanca where business is done differently. It took me a while to adapt and learn how to be effective in a completely different work environment.

How is Kingston Vineyards doing now?
I’m about to fly to Chile for our fifth vintage, which is hard to believe. Our wines are now on the wine list in some great restaurants across the U.S., such as Michael Mina and the Ritz Carlton in San Francisco; Masa, Jean Georges and Restaurant Daniel in New York; Spago in Los Angeles and the Four Seasons in Jackson Hole. A third of our wine sales come from our mailing list—where customers can buy direct and we ship to their homes. We’ve been fortunate to have a reputation for top quality wines with limited production, so the demand for our wines far outstrips supply. Wine Spectator recently said the Kingston Family Vineyards is leading the way, bringing excitement to Chile.

Oh—and since you live in San Francisco—I’m especially proud of the fact that our “Cariblanco” Sauvignon Blanc is by the glass at Hog Island Oyster Co. in the Ferry Plaza. Byron, our winemaker, loves to sit at the counter with his wife Mary for some fresh seafood after landing in SFO from Chile.

That’s right by my house. So…you know how it’s kind of impressive if you have a signed copy of a book? Well, what if I bought a bottle and got it signed by you? Is that absurd?
People actually do that…but no one has ever asked me. Maybe that’s when I’ll know I’ve really made it big…

What do you do on a day-to-day basis at the vineyard?
I ‘m actually based in the Bay Area, a long way from our vineyard in Casablanca. I used to fly down every other month, but since my daughter Annie was born last year, I now go about half as much. (We’re headed to Chile next week for Annie’s third trip.) My day-to-day job involves everything on the importing, sales & marketing side of the business. That means deciding the design of our wine labels , how much more pinot noir we should make in 2008, or how to adapt the financial model that forecasts when we’ll break even. But I don’t do it alone and we now have a small but mighty team based up here in the U.S. and flying back & forth to Chile.

Tell me a little bit about yourself.
I was born in Princeton, New Jersey; nowhere near as glamorous sounding as Casablanca, Chile. I also went to Princeton for college, and studied international affairs & public policy. I was convinced I was going to move to Washington, DC and “make policy,” until I realized I’d probably have to be a politician and run for office to do that. I moved to Northern California in 1992 for a “year off” before getting a real job on the East Coast but have been here ever since. Along the way I got my MBA from Stanford. That was enormously helpful in giving me the tools to help me start my own business. My husband Andy and I live in Portola Valley with our daughter Annie and our loveable 90-pound, oaf of a dog, Harley.

You’ve worked in big companies, small companies, and now you’re doing your own company. Can you tell me about some of the core differences?
I think the great thing about working in big companies is that you can specialize. You often only need to focus on your piece of the pie, and you are often supported with more infrastructure. I miss the free office supplies (all the yellow stickies I could ever dream of!) and Friday afternoon happy hours. And I especially miss being able to call IT support without getting an invoice!

But the bad news with a large company culture can sometimes be lack of ownership, and a pass-the-buck mentality. In a small company, you really have to pull yourself up by your bootstraps, and the buck stops with you. There’s no IT support. No free pens. But you can build something you’re proud of, and the diversity of your day is amazing. I love the fact that today I poured wine at a favorite restaurant, worked with a consultant in Chile to develop winery tours (you should come for a visit!), updated our distributors on recent excitingreviews from Wine Spectator and Wine & Spirits magazines, and got to give an interview to teach others how to get rich! (Can we talk again when the winery actually breaks even?)

Do you think everybody should do their own business once?
Not necessarily. Not everyone’s dream is to start their own business. I think everybody should figure out a way to follow a dream. Go right, go left, go straight. Just make sure you go forward.

Courtney and Annie
Early morning harvest with fog receding, Kingston Pinot Noir

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  1. avatar

    Love the crossroads analogy! So apt. So many people get stuck, sitting there, taking no action.

    Plus once in motion it’s easier to stay in motion. Its the stopping and starting that takes the most energy.

  2. avatar

    Wow, talk about freaky. I just posted yesterday asking for these answers – thanks! Any advice would be great in addition to this post:

  3. avatar

    This is my favorite Friday post yet! Courtney is so inspiring and I loved learning about her business. Thanks for doing this piece, Ramit :).

  4. avatar

    Great lesson about the crossroads analogy.. Thanks for sharing.

  5. avatar
    sridhar dhapu

    cool inspiring words.. i lovethe concept of yellow stickss and crossroads.. may be even i start to move.. THANKS for sharing,,,:-)

  6. avatar
    Nordquist Blog » Blog Archive » What’s it like to pursue a dream

    […] enjoyed this interview I came across at the I Will Teach You To Be Rich blog. It tells the story of Courtney Kingston, who […]

  7. avatar

    This article is an example of why I have this website as my homepage. It is inspiring and insightful. Well done.

  8. avatar

    Agree with everyone, great questions, great answers. Very quotable. Thanks!

  9. avatar
    I Will Teach You To Be Rich » Friday Entrepreneurs: Courtney Kingston, Kingston Family Vineyards at Life Putting - Dan Putt

    […] I Will Teach You To Be Rich » Friday Entrepreneurs: Courtney Kingston, Kingston Family Vineyards […]

  10. avatar
    Blair Christopher

    At first, I didn’t like your Friday Entrepreneurs segments. Then you know what I did? I started reading them! Usually the Monday after it’s posted I will read it during my lunch break (like I am now) and I love it.

    Keep it up. I don’t drink wine, but my father “thinks” he is an expert. I’ll be sure to see if he’ll try some Coastal Chilean wine.

    Her Post-It note advice sounds a lot like Getting things Done. Start with a “Project” and break it down to an Actionable item. Even if it’s a small action, you are still making progress to the ultimate goal.

    Thanks for another great article, Ramit.

  11. avatar

    “Go right, go left, go straight. Just make sure you go forward.”

    I love this.

  12. avatar
    Cloudy Thinking » Blog Archive

    […] Sethi interviewed Courtney Kingston, who left a managerial job in high tech to start a winery in […]

  13. avatar

    hmmmm, I would hardly classify her as an “entrepreneur”. She had all infrastructure behind her, her family was in Chile and owned land there since early 1900’s!

  14. avatar

    Before she jumped in to start her own business, she had the experienced from working for a big company, the skills (MBA), and the family support in Chile.
    Great post Ramit.

  15. avatar
    Ecclessial Mercenaries –

    […] way of looking at it is from this interview with a designer turned wine maker, Courtney Kingston (of Kingston Family Vineyards) One of the biggest challenges for me was going from a job that was […]