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Jake Kennedy
  • Alumni

After graduating from Prep in 1981, Jake attended Villanova University and graduated in 1985. He then moved to New York to work for Ernst and Young in the audit practice for five years and then moved back to D.C. to work in the private industry, gaining additional financial responsibilities that helped his career. He earned his CPA and MBA. At the age of 50, Jake passed all three levels of the CFA exam. He recently retired as the CFO for Amentum, a government service company with revenues of over $6 billion and was voted CFO of the year 2021 (nominated in 2020) by Washington Exec. Jake and his wife have four adult children and reside in Frederick, MD.

You recently hiked the entire Appalachian trail. What prompted you to take on such a challenge?

I was prompted to take on the challenge of completing the entire Appalachian Trail as a mainly solo through-hike. While working in corporate finance for close to 36 years, I also enjoyed the outdoors and while tethered to my desk, I longed to be outside and enjoy nature on a more full-time basis. Serendipitously, the company I worked for went through some ownership changes, and I felt it was the right time at 57 years of age and in relatively good health to take my 2200-mile adventure!

What did you learn along the way?

I learned so many lessons during my hike. First, I read and researched so extensively about how to prepare and be ready for the trail. I sought advice about the equipment and provisions needed. There are so many so-called “experts” who provide expertise about many hiking scenarios. I was preparing for all kinds of different scenarios; weather, insects, food, and emergencies. I even completed a backcountry emergency preparedness class and was certified in CPR! Provisions for all those potential scenarios result in carrying extra weight in your backpack. And the heavier the backpack, the harder your hike. I quickly learned that it is impossible to plan and prepare for every scenario, and that I needed to be flexible and ready to take on challenges as they come. I was able to reduce my backpack burden and rely on my instincts and the resources available when unforeseen challenges arose. As I look back, this is a real-life metaphor for prioritizing what is really important and keeping your life simple.

What stands out to you most about your experience?

Interestingly, everything was reduced to the very basics. Every day, I woke up with one goal in mind of hiking as many miles as I could possibly achieve. On a typical day it was 15-20 miles. I had to think through what would get me to that goal. Do I have enough water? Do I have enough food? How is the terrain? What is the weather? This was every day, with no distractions of email or TV.  

Another thing that stood out was how wonderfully diverse our country is. I met folks from all walks of life. Most of my fellow hikers were exceedingly charitable and offered advice and other necessities when needed. There were times when I needed help, and my fellow hikers never failed to provide assistance. This camaraderie and charity were paid forward and the people I met all helped in achieving the goal of hiking 2200 miles, from Springer Mountain, Georgia, to Mt. Katahdin in Maine.

Finally, without being trite, I have always appreciated nature but, being outdoors for over five months, hiking over mountains with diverse terrain, I was very fortunate to experience the wonders of nature. There were wild ponies in Grayson State Park in Virginia, the White Mountains in New Hampshire, the rivers and lakes in Maine. Notably, hiking over the Presidential range in New Hampshire, which includes a trek over Mt. Washington, was physically very challenging but the incredible views were well worth the effort.

Jake Kennedy - Mt Washington

Summiting Mt. Katahdin with my wife, who was incredibly supportive along the way, what an extraordinary way to complete the trail! Realizing I accomplished my goal was an incredibly emotional experience. I was truly struck with the importance of preserving the beautiful gifts God has bestowed upon us. At the end of the day, you never know what curve balls life has in store for you, so when you have an opportunity to fulfill a dream, by all means, take that opportunity.

Jake Kennedy Mt Katahdin

How did Jesuit education prepare you for your career and/or this recent experience hiking the Appalachian trail?

At Prep, there is NO question the academics are rigorous and that extracurricular activities are emphasized. The school sets important but fair standards for young men to meet. Striving to achieve these standards develops a sense of responsibility and with the proper fortitude, you can exceed those objectives, and you EARN the benefits from the effort you put in.  

During my career I always set high standards for myself and for my team. I worked hard and embraced the notion of continuous learning and development. Also, the strong emphasis on service and helping others has been foundational for me. I always ask, “how is what I am doing going to impact others?”, and my actions always embrace the notion of fairness and equity.

On the trail, the most important attribute is fortitude. But I found that a sense of service to others was key for my hike. There wasn’t a day that went by that a hiker or myself didn’t need a helping hand.

Jake Kennedy

What was one of your favorite memories during your time at Prep?

I really was able to forge some great friendships at Prep. Hanging out during free periods, sharing funny anecdotes about what may or may not have happened in class. We stay in touch with each other, and it is wonderful to witness what great people they have become! Also, I enjoyed the balanced instruction provided by some of the best teachers I ever had. Miss Collins, Mr. Horsey, Father Brady, Mr. Ochs, Father Galvin...I remember them all very fondly. I have so many memories, but one of the memories that really stands out is my sophomore year, Social Studies class. Mr. Horsey opened the very first class by playing two songs. A song by Bob Dylan and the other by Jethro Tull. I thought to myself, this is going to be a great class!

What impact did Georgetown Prep have on you?

Prep had a profound impact on my life. My junior and senior years, I faced some family problems, and Prep could not have been more supportive during those difficult times. I often reflect on how lucky I was to attend Prep. My teachers, classmates, and spiritual advisors all had significant influence in how I live today. I often talk to colleagues about their high school experience, and I get a passing thought from them however, they get an earful when I describe my high school experience! Again, I was blessed to have been able to attend Prep. Plus, I impress my friends when playing trivia….Western civilization and Latin class definitely helped!

What advice do you have for current Prep students?

Again, my advice to Prep students is to savor the time and instruction. I know sometimes school can be a grind, particularly at a school with the academic rigors of Prep, but know that time is fleeting. Treasure learning new things and be thankful for the wonderful campus provided to you. Take on challenges and most importantly, be yourself. Too much time is wasted by teens trying to be what they think others want them to be. I have made many mistakes in my life and have learned and improved from all of them. Life is a journey, Hike On!

A few more rapid fire questions about the hike:

When did you do the hike?
I started on March 26, 2022 and finished on September 7, 2022.

Did you hike this by yourself?
I hiked most of the trail by myself, but there were many days that I hiked with fellow “through hikers”. My wife joined me on the trail for a number of day hikes including summiting Mt Katahdin, Maine, and she was very supportive with helping me resupply.

Jake Kennedy

How many days did it take?
Five months and 10 days. My daughter got married in May so I took about a week off then for her wedding.

Where did you sleep at night?
Over the five months, I slept either at a designated shelter on the AT, in a tent, hostel, public campsite, and, when by a trail town, a local motel.

What was the hardest part (sunburn, bug bites, not enough water one day, etc)?
For me the hardest part was physically hiking the White Mountains in New Hampshire. I was expecting a somewhat, well graded trail but found the trail to be incredibly rocky, strenuous and steep (close to technical mountain climbing). During another experience, early on in the hike, while in the Great Smoky Mountains, temperatures dipped below freezing and it rained/snowed, so dealing with the wet gear and cold temperatures was challenging and scary (thoughts of hypothermia crept in my mind). In NY, I accidentally agitated a wasp’s hive nestled in a log and was stung by at least 10 wasps. Thankfully, a fellow hiker had extra Benadryl!

Did you train for this?
I exercised regularly before deciding to hike the AT so I was in decent shape, but hiking an average of 15 to 20 miles a day is hard to train for, not only preparing for the physical effort, but also contending with the emotional challenge that comes from hiking for over five months. (One develops “trail legs” and builds the needed stamina during the first few weeks). I researched the AT quite a bit beforehand and watched “on line” videos but nothing really can prepare you for the reality of hiking so many miles over such diverse terrain.

Jake Kennedy and Tom Scott in Georgia

Jake Kennedy with '81 Prep Alumnus Tom Scott in Georgia

Jake Kennedy with his wife, Analiese at the southern terminus approach of the Appalachian Trail in Georgia

Jake Kennedy with his wife, Analiese, at the southern terminus approach of the Appalachian Trail in Georgia