Anthony Bourke, 62: From the Vineyard to the Sky and Back

“Find a job you love, and you will never work a day in your life.” Anthony Bourke is one man who’s pursued not one but two, three, and more jobs he loves. By doing what he’s passionate about, he manages to blur the line between business and pleasure and connect his seemingly unrelated careers. As a young man, Anthony was first introduced to the wine industry through his father’s interest. Through his involvement, AB got a taste of the world and set off on a journey of learning and rich experience.

After attending the University of California, Berkeley, where he wrote his senior thesis on the post-prohibition recovery of the California wine industry, AB studied under the tutelage of some big names, and later started his own wine brand named after his wife, Hale Mary Wine, from a most humble place, with the help of loved ones. All the while, he still had a hand in shaping well-known labels in the California wine industry. While Anthony’s work on the ground was full of opportunity, he also longed to fly in the cockpit of F-16s. So, he took a 20-year hiatus from winemaking and became a highly experienced and decorated F-16 fighter pilot.

Serving in the United States Air Force and the California Air National Guard, Anthony flew tactical missions all over the world, accumulated more than 2,700 hours of flight time in numerous high-performance aircraft, and was one of the first pilots to fly his plane over New York City in the homeland defense efforts on 9/11. Following his time in the military, he realized that being a fighter pilot opened up unique doors in the business world he could have only imagined. Now, along with his winemaking, he teaches corporate management how to apply tactical aviation tools in the business world through Mach 2 Consulting. And that’s just the half of it. With all these experiences and opportunities, AB’s businesses and life are aging like fine wines.

How old are you?
Sixty-two.

Are you married? Kids?
I am married and I have three children aged 34, 31, and 29.

Where are you from and where are you currently based?
I’m born and raised in Palo Alto, California. I currently live full-time in Park City, Utah.

Growing up in a family that invested in wineries like Chalone and Ravenswood must have shaped your perspective on the industry. What were some of your earliest memories of the wine world?
My father became very interested in the wine industry when I was in high school. My earliest memories of wine were driving down to the pinnacles with him to crush grapes with Dick Graff and the team at Chalone Winery. It was a wonderful experience which continued on when he invested in Ravenswood, and I spent time in Sonoma with Joel Peterson and his crew helping with the winemaking process. After graduating from Berkeley, I had the pleasure of working for Jeff Baker and Pam Starr at Carmenet Winery in the Sonoma Valley. That was a special treat in my life. It also reinforced that somehow I wanted to be involved in the wine industry when I “grew up”.

The origin story of your wine brand, Hale Mary, is fascinating. You started it in your Marin County garage with family and neighbors, right? What was the biggest challenge in those early days?
Yes, at the time we started Hale Mary Wine I was serving on the board of Merry Edwards winery. Merry was nice enough to sell us grapes, which we brought down in the back of a pick up truck to our home in Ross, California, and crushed them with the neighbors and our children. We did this for over five years in our garage, and while it was often chaotic, it was a wonderful family and community activity which we still cherish to this day.

What prompted your brief hiatus from the wine world to pursue your dream of flying F-16s? Was that always a parallel passion?
Flying F-16s was my life dream from a very early age. I actually dreamed of being a 35-year-old F-16 pilot in the reserves; a United Airlines pilot based in San Francisco; and a bachelor. The fact that my dream came true, and I was able to fly F-16s and for a period of time [fly as a] United Airlines pilot is very cool. The bachelor thing didn’t exactly work out, but I am so fortunate to have a wonderful wife and three fantastic children. Sometimes dreams change.

As one of the first pilots to fly over New York City on 9/11, how did that experience change your perspective on your military service and life in general?
Obviously, the post 9/11 world made my military experience very real and very meaningful. There’s a big difference between training and preparing to deploy your F-16 thousands of miles away to defend your country’s interest against foreign adversaries versus flying homeland defense over your own country, defending your homeland. This experience was powerful and it reinforced, to me, that we all need to find some way to help keep our country safe and our people free. That doesn’t necessarily mean everyone has to serve in the Armed Forces, but I hope it created some common value of how fragile our liberty is and how important it is to protect our nation.

How did your 20 years in the Air Force and Air National Guard shape your approach to challenges and decision-making?
Twenty years in the Air Force and Air Guard reinforce, first and foremost, the power of training. When you are well trained, overcoming challenges and making split-second decisions becomes much easier. In essence you’ve seen the movie before, you analyze the situation and take appropriate action. You are in control. This is one of the great values that military service provides our men and women in uniform. Through great training and a clear sense of mission, we are able to react quickly and effectively in the most challenging circumstances.

What specific fighter pilot principles have translated most effectively to the business world?
I think the most powerful lesson that I’ve taken from the world of tactical aviation is the principle of debrief. Debrief assumes that no matter how well we train, no matter how talented we are, no matter how hard we work, that no fighter pilot has ever flown the perfect mission. I think it’s also fair to say that no one in business will ever have the perfect day, the perfect week, the perfect month, the perfect client interaction or deal. That’s why at the end of every fighter pilot mission, we always call time-out and hold a debrief.

Debrief is a safe environment, where there is no rank, and there is no hierarchy, and which allows us to learn from both the mistakes and the victories of today’s mission and to continue to improve as individuals, as a team, and to make sure that our leaders receive the honest, real-time feedback they need to keep us ahead of the threats, ahead of the competition, and head of the inevitable change that will continue to come our way. Debrief drives a culture of continuous improvement in tactical aviation and in business.

After two decades serving your country, what drew you back to the Bay Area and the wine industry?
I love the San Francisco Bay Area and am particularly fond of Marin County, California. It is a special place on the planet. Physically beautiful, culturally vibrant, surrounded by the San Francisco Bay and the Pacific Ocean, and yet just 15 minutes from San Francisco. It is also just south of my favorite wine region in the world, which is the Russian River. The Russian River, in my opinion, is one of the best growing regions in the world for pinot noir, and it had been my life’s dream to make beautiful, elegant pinot noir wines.

Your career trajectory is unique and expansive—fighter pilot, top mortgage banker, startup growth leader, CEO. In your mind, is there a common thread that connects all your seemingly different paths?
Great question. I think for a good period of my life I pursued any professional career that allowed me to continue flying F-16s in the reserves. And doing this, I started to realize two things. First, that I enjoyed the challenges of business and building great businesses. I also began to realize that being a fighter pilot opened up doors for me in the business world that I could not have imagined. There is strong support for our men and women in uniform in this country, and particularly for tactical aviators. I was the beneficiary of this support, for which I am truly grateful.

How do you balance your consulting work, winemaking passion, and personal pursuits like surfing and skiing?
Skiing takes a front seat for physical activity in the wintertime and surfing takes the front seat in the summertime along with riding a mountain bike. I build time into most days to support my consulting business and generally travel one day a week to give a speech somewhere in the USA and occasionally outside of the USA. Wine making is seasonal. I work hard during the spring securing great fruit. I work hard in the late summer and early fall deciding when to pick that fruit and how to vinify the fruit into beautiful wine. Hopefully the wine evolves beautifully through the winter and some time in late winter/early spring. I start spending time again thinking about what our final blends will be. This involves lots of tasting and blending to arrive at our final offerings for the vintage.

Your upcoming book is titled The Art of The Debrief. Could you share how the concept of debriefing has impacted your approach to both business and personal growth?
I think I covered debrief pretty well in one of your earlier questions. In my mind, debrief is the secret between showing up every day and doing a job versus constantly striving to be the best you can be. It requires an open mind and the ability to give and receive honest, real-time feedback. It also embraces an attitude of humility—the realization that you can always be better, no matter how good you think you are. I think this concept of debrief translates beautifully to business and personal growth.

After such a multifaceted career, what remains on your bucket list?
That’s an interesting question. As my middle daughter is about to have our first grandchild, I am often thinking about the joy I will experience being involved in my grandchild’s life and how I can be a great grandparent. I often think about how I can try to age gracefully and keep my friends and family close as my physical abilities decline and, hopefully, my wisdom increases. No guarantees on that front. On the winemaking front, I have thought about experimenting with other varietals, particularly syrah and sparkling wines. We shall see what develops there.

I’ve also found that moving into my 60s gives me the luxury of taking time to give back. I have pursued this endeavor in three different ways. 

I want to give back to Veterans and I have served on a Patient Advisory Board at the San Francisco VA Hospital to make sure that Veterans are receiving the best possible care. I am in awe of the VA, and think they do an incredible job serving their patients. https://www.va.gov/san-francisco-health-care/

I also serve on the Board of the UC Davis Viticulture & Enology Program. https://wineserver.ucdavis.edu/ This is my way of giving back to the California wine industry, and making sure that UC Davis maintains it’s position as the Premier Viticulture & Enology program in the world.

Finally, I have become active in supporting The Utah Avalanch Center https://utahavalanchecenter.org/about/who-we-are. This is an organization that is dedicated to education and safety for skiers, snowmobilers, and anyone who is venturing into the backcountry. They are also a a critical element in the safety protocols of Utah Department of transportation. They are the gold standard of avalanche, safety, and awareness in the country, and maybe in the world.  

What are your three life non-negotiables (i.e., the things you can’t live without)?
1. My wife.
2. My children and now grandchildren.
3. Not allowing the pursuit of money or fame to keep me from pursuing my passions.

Editor’s Note: Some answers may have been edited and/or condensed for clarity.

Connect with Anthony: LinkedIn / Mach 2 Consulting / Hale Mary Wine

Images courtesy of Anthony Bourke