The Past Year: Things of Significance (Family, Business, Persona)
YPO retreat with Kevin, Kent, Marco, Jeremy, Jeff, and Robert. We had some challenges but they seem to have drawn the group closer together. I am super grateful for these men in my life.
Hunter’s Graduation, so proud of him and his tech start-up. Best quote from Hunter, “I won the dad lottery.”
Trip to Italy with Olivia and her comment, “I can always count on him”, that I overheard her say to her friend Talis about me. Incredible to see her doing her thing. Especially with her internship and having some of her designs picked by Zara Home and the French brand.
Summer with Grayson and seeing him develop into his own person. Best quote from Grayson. “I want to study in Spain and not be like the other kids in Oregon.”
What aspects were the most important to you in the following areas last year? Which happenings or events were the most significant? Summarize briefly.
Personal
Decision to prioritize my health. Did a deep dive physical and decided to schedule my stem cell treatment to address an old parachute injury to my right leg and overuse injuries to my shoulders and lower back.
Reading more about relationships and philosophy from Allan Watts.
Hobbies
Skiing, took a great solo trip to Chamonix, France to do my goals for 2024.
Flying: getting my airplane to Portugal and learning the basics to flying in Europe.
Turning Pilates into a regular hobby to help address overuse injuries during my time as a Navy SEAL.
Chess, finally got to 1600 rating!
Health Fitness
Taking the results of my DNA/Physical exam and implementing better eating habits. Pilates and Yoga regularly.
Friends Community
Losing a lifelong navy friend, Jason Degroot to cancer. Then unexpectedly losing another great friend and entrepreneur, Solomon Choi (Founder of 16 Handles). Being able to reflect on the lives they lived and how they improved my own life by knowing them gives me inspiration to continue to live a good life for myself and my family.
Getting to know James Altucher better and visiting him and his amazing wife and family in Atlanta before the Holidays.
Meeting new friends, Bastian, Phil, Carlos (pilot), Georges, and Diogo in Portugal. Getting to know Sami better. Taking that trip to Laplands, Finland.
Belongings
My Vans RV6 airplane. Being able to enjoy flying and share this with others. I took over twenty new people flying this year. All amazing experiences except one where I took a Ukrainian flying who was traumatized by heavy turbulence! Lesson learned, don’t fly around Cabo De Roca in high winds!
Also at the end of the year my plane was damaged by the owner of the airport I keep it hangared at. He denied doing the damage with overwhelming evidence.
What bothered me most was the lack of integrity and that he put me in an unsafe situation by not disclosing the damage. I noticed it on take-off when my controls were stiff, landed and found extensive damage under my left wing from a small tractor used to mow the grass. My left aileron was damaged along with structural damage to the inside of the wing.
This also was a great reminder of how important it is to do the right thing when nobody is watching. Reminded me how much I appreciate the group of aviators who brought me up to fly air combat in the Yaks at KSEE field in San Diego.
Intellectual
Regular reading. However, this made me realize I need more intellectual activities in 2025.
Finances
Nothing earth shattering here and this definitely nudged me on 2025 thinking.
Emotional/Spiritual
Explored a psychedelic retreat by asking friends who’ve done it previously. On my list in 2025.
Bucket List
Mostly travel related. Traveled to Turkey, Finland, Denmark, and Sweden. All new countries for me.
Saw the northern lights for the first time at my friend’s family lodge in northern Finland.
Six Sentences about Last Year
Wisest Decision I made
Investing in Hunter’s business, Deep Rent.
Biggest Lesson Learned
The importance of health and cumulative effects of taking care of our bodies.
Biggest Risk
Changing the way I date women. Looking more seriously rather than a bunch of casual encounters that I know will lead nowhere.
Also saying no to USAA as an advertising sponsor after their agency Publicis kept paying us late. We had over 4 invoices past due 180 days. Then some on the team lying to us, so I said no to the money because the relationship was killing my team’s morale. USAA is a great company but some customers you have to quit was the lesson.
Biggest Surprise
A family member going bonkers on my mother for an arguement that happened between them and my mom’s husband. Without going into details it was extremely disappointing to see their behavior. My mom had to see a doctor for the stress it put on her. I’ve been trying to rebuild a relationship with this person and this feels like an avalanche buried me as I was close to the peak of the mountain. Feels like two years work is in a snow pit at base camp.
A guy I thought I trusted who damaged my airplane and didn’t say anything, then lied about it. Super disappointing.
Biggest thing I completed
Getting the Military Content Group (MCG) /SOFRP stabilized and growing again after our last bookkeeper Randy Wang embezzled close to $300,000 over two years. Grew our traffic under MCG from a few million visitors to over 50M.
Most important things I did for others
Invested in Hunter’s Ai prop tech startup Deep Rent.
Found my daughter a mentor as well as helped find mentors for five other business school alumni kids.
Gave two talks on the importance of positive mindset to over 1200 people.
Took the manager of Dear Breakfast, Nuno, flying.
Mentoring talks with Grayson and Olivia on their career and study choices.
Tipped my pilates instructors and the entire staff of Dear Breakfast and Liberty Cafe for the Hoidays.
Six Question about the Past Year
What am I most proud of?
My children and the life I built for myself in Portugal.
Who are three people who influenced you most?
Allan Watts, Hunter (for his book recommendations that remind me to keep learning), and my collective YPO forum mates James Altucher for always pushing me into areas I didn’t know existed.
Who are three people I influenced the most?
Hunter, Olivia and Grayson.
What were you able to accomplish?
Just simply helping them live a good life and seeing how they continue to make good decisions on their own.
What is the best thing you discovered about yourself?
My ability to always see the positive in a bad situation. My default to positivity and my ability to build new relationships that are essential to a life-time of personal resiliency.
What are you most grateful for?
My kids and their mom (we’ve all been through hell and come out the other side). The friends and community of YPO, and the Harvard Business School Alumni. Building back a good relationship with my father.
The Best Moments
Describe the greatest and most memorable, joyful moments from last year.
Hunter’s graduation from the University of St. Andrew’s. Best quote from Olivia, “When do they hand out their wands!” Made me smile. The Harry Potter-like campus is incredible. Felt great to have all his siblings there to cheer him on. I think it impacted Grayson the most and encouraged him to study abroad outside of his comfort zone.
The first time flying over the coast of Lisbon, pure magic.
Taking my mom and kids to Amago for the full tasting menu. Incredibly lucky to have them all visit Lisbon this summer and to treat them to a world-class dining experience.
Flying seaplanes on lake, Como with the Como Aero Club in Italy.
Spending time with Grayson this summer just being guys.
Taking Olivia and her bestie to Capri, Italy for a week of relaxation, beach clubs, and fine dining.
Realizing I am comfortable with my own company.
Letting Go
Is there anything else you need to say? Is there anything you must let go of before you can start your next year?
Just want to say goodbye to Jason, and Sol. Incredible friends who left us all way too soon. But a reminder to live life in the present and appreciate the people we love.
3 Words that Describe the Past Year
Change, Friendship, and Life Reflection
The book of my past year would be titled: A Pirate Looks at 50 (I wrote about this on SOFREP)
Farewell to My last year
If there is anything else left that you would like to write down, or there is anybody
you would like to say goodbye to, do it now. The same as I mentioned above.
See you on the other side Sol and Jay.
The Year Ahead in 2025
Dream Big
What does the year ahead of you look like? What will happen in an ideal case? Why will it be great? Write, draw, let go of your expectations and dare to dream.
I will sell my media company and transition to growing my next business. This is the next stage in my life. I’m excited to build something new and have a few ideas that are top of mind. Been thinking about this for a few years.
My Next Year will be About
Define the most important aspects of next year in the following areas*. Which events
will be the most important? Summarize briefly.
Personal
Health is the most important this year. Avoiding joint surgery by doing stem cell treatment in Colombia. The ability to do the things I love with the people I love into old age is a priority.
Work, Studies, Professional
I’ll take at least one course on business, wine or cooking. Things I love to do. I’ll also write my parenting book. This is a huge one for me and very excited to write a great book on parenting that incorporates all I’ve learned in life, as a Navy SEAL sniper, mental management and as a dad.
Belongings
If I sell my home I’m going to do another home project or build a house with my own airstrip in Portugal.
Relaxation, & Hobbies
Continuing to prioritze my health with regular massage, yoga and pilates. My guilty pleasure of getting a very unmanly pedicure monthly (who knew it was so good!). Enjoying my hobbies this year, especially flying and skiing with my kids. I’d also like to start surfing again or take a trip somewhere warm if my chronic joint pain improves with stem cell treatments.
Health Fitness
Same as above and will continue to stay active in some way (biking, yoga, pilates, swimming) 7 days a week.
Friends, & Community
Continue to be a good friend who checks in regularly. I’m going to do more one-on-one check ins with my YPO forum mates this year. Best quote from a good friend John, “To have good friends you have to be a good friend.”
Intellectual
Going to schedule a business class, and a professional chef-grade cooking or wine class. Finish my Portuguese lessons with Eliana.
Emotional-Spiritual
Will do an Ayahuasca retreat this year and continue to read philosophy books on life.
Finances & Bucket List
Work on selling my company and building a family office. Will research a space travel option as this would be an incredible experience. Definitely Japan this year but likely in the fall.
Magic Three of 2025
These three things I will love about myself
Always learning. Being a great dad and friend.
I am ready to let go of these three things
Too much time on dating apps, bad energy people in my life, and the odd joint (yes that kind). Would like to stick to an occasional edible.
Three things I want to achieve most this year
Business sale, finish my book on parenting. Get my video game to market. Have my tv show based on, Steel Fear, get a greenlight for production.
Three people who will be my pillars during rough times
Mom, and my YPO Forum mates (6 of them!)
Three things I will dare to discover
Ayahuasca, new education, new travel and culture.
Three things I will have the power to say no to
Drinking when I don’t want to, opportunities that don’t align with my goals or values, and people who don’t align with my values.
Three things that will improve my surroundings
My friends & family. YPO and my Harvard Business School Alumni group.
Three things I will do EVERY morning
Stretch, chess, exercise, and my grateful journal (ok, four things!).
Three things I will pamper myself with regularly
Massage, sauna, and alone time. Three places I will visit
Japan, India (or Brazil), and Italian Alps.
I will connect with my loved ones these ways
Regular phone calls, hosting at my Lisbon loft, and trips together.
Three presents to myself if I hit my financial goals
Patek Pilot Watch, G model Porsche, and taking my kids on an amazing ski trip this winter.
Six Sentences about my next year
This year I will not procrastinate any more on…
Too much chess, social media and dating apps.
This year I will draw the most energy from..
The people I surround myself with.
The people most important to me and also be open to meeting new friends, especially in Portugal.
I will be the bravest when…
People need me in the face of adversity and in my own life.
This year I will always say yes when…
Something aligns with my goals. Either professional or personal, like Sami from Harvard inviting me to Finland last year. I reorganized myself to do this magic trip and ended up meeting incredible people and seeing the northern lights for the first time.
This year will be special for me because…
It’s a massive year of transition if I sell my business and my tv show (based on the thriller Steel Fear) goes into production (finally!)
My Word for the Year Ahead: Transitional
Secret Wish: Find a Best friend and Life Partner
