Perhaps one of the gifts of age is that we are allowed to revel in our complexity. We have enough life experience that we can engage widely. We have the ability to discern, we understand subtlety as we become more sophisticated in our ability to move fluidly across interests. This is not to diminish youthful exuberance, but our equally thrilling exuberance is informed by more time walking the earth. It’s just different, and perhaps wiser.
Rafe is a finance guy, an art guy, a music guy, a longevity guy, and a dedicated dad. One could assume that there would be limiting complications here, but there aren’t; it is all of a whole, a mosaic, each part amplifying and adding to the others. We live in a time where social media rewards the simple, the outrageous, and the sensational. Rafe, although highly successful in the world of finance, is someone we think of as a humble North Star hidden in plain sight. The sort of person whose curiosity reaches out into the world and brings back knowledge and experienced insight that others may not see. The sort of person we like to learn from.
How would you describe your dating life over the last 12 years?
Now I’m looking back on 12 years of dating and what must be close to, or even more than, 1,000 first dates, and I’m still hopeful that I will find the right partner for me; maybe it sounds ridiculous to still be so optimistic, but I know there will be someone to share life’s experiences with. I’ve met so many incredible women on this journey, several of whom have become close friends. I am still looking for the right woman.
Looking at what my dating goals were coming out of divorce – I desperately wanted to find someone who could be a mother to my two young daughters while also wanting to add more children into the mix. My friend, Norman Lear, once told me after a long chat that he could see how much I loved being a father, like he does, and encouraged me to find someone that could be that kind of partner. I found that most women in NYC didn’t want to be in an instant family.
My daughters were starved for loving affection from a female figure since they didn’t really get that from their mother; they were always excited about and kind to any new woman I was in a serious relationship with and chose to introduce. This made me excited too; the experience of the family, in addition to the one-on-one relationship, was an enormous driver for me. Unfortunately, the few women who have made it to that point either quickly realized they were not ready to be an instant mom, or I did not see it working long-term.
I have met two women in the past 12 years who I felt would have been great partners in life. One had two girls around the ages of my daughters and I think the four girls and me were more excited about the partnership than she was. The other woman I met during my divorce; though I was sure I was ready to start looking for a partner, I was not truly available for a relationship at that point, and ultimately we could never figure out how to find our way back together. If there was “one that got away” it was clearly her.
You studied photography in college, along with economics, and even practiced it professionally for a while. Is this a right brain/left thing, or are they coming from a similar place for you?
I read recently that the whole right / left brain thing is misplaced, and our brains can and do both creative and mathematical things from either hemisphere; this is more logical to me as I always wondered why I was not only comfortable with but also excelled at both. Frankly, I would say that my creativity allowed me to succeed in finance because the problem solving was well beyond numbers and excel spreadsheets. I have always used my creativity and soft skills to excel in helping companies grow and navigate the bumps in the road, but you can also see my numbers/geometric interests in my photography.
At the interview for my first job in finance I actually brought my photography portfolio — I was coming in with a liberal arts education and I was up against candidates with formal degrees in finance. But the reality is that companies are living and breathing things that have more variables than a spreadsheet can handle. My education allowed me to be both analytical and creative. I have consistently brought my creativity and soft skills into finance – helping companies grow and navigate the bumps in the road – just as I have used my analytical skills and interest in geometric compositions in my photography.
What interests you in the world of photography here today?
As life went from working 60-70 hours a week to working 70-80 hours a week with two daughters, I stopped developing and printing, and had my work printed; then I stopped taking pictures altogether. Ultimately, I just couldn’t carry my Hasselblad equipment along with the diaper bags and baby gear. To fill the photography need I started collecting photography. My focus is to primarily procure artists that utilize photography as a means to document/capture their art. Sandy Skoglund, Vik Muniz, Erin Sheriff, and Noemie Goudal are good examples of artists that are using photography to capture their art, but they all use different fine art skills to create their art from sculpture to painting with chocolate syrup.
I joined Fotografiska when it opened in NYC a couple of years ago after I went to the original in Stockholm. They have amazing shows that stand up next to ICP, MOMA and the MET.
What is your relationship with music? How does it affect you, and how do you enjoy it?
Music is much more important in our world than most people realize. I love how there is rarely a moment when music is not additive to what you are doing. While I don’t mediate with music, in any other moment I’d rather have music playing in the background. I am affected by music, but I think I enjoy it differently than most. I’m not a dancer…maybe I’m self-conscious about my abilities, but mostly because I really like to observe the musicians create their sounds…it fascinates me and I wish I played an instrument.
A business colleague once told me when my kids were 4 and 5 that music was the best way to stay connected and relevant to my kids; he said to always listen to new music and make sure to share music with my kids. When I was in the process of getting divorced, I bought my girls their first iPods and loaded them with music that we had bought together ever since the iTunes store started selling music. I took them to their first concert, Hannah Montana/Miley Cyrus with the Jonas Brothers opening.…the woman who took our tickets when we entered looked at me and the girls and said with a grin, “God bless you”. I spent a lot of the concert holding up one girl at a time. We’ve been to many concerts and festivals since. One of my favorite moments was at a Cold Play concert when Parker was around five, and they sent out giant yellow balloons into the crowd to bump around; I looked at Parker, who was mesmerized by the balloons bopping up and down, and said, “would you like to touch one?” She grinned. The moment I saw one coming in our direction, I grabbed Parker, told her to put her arms up like superman, and I threw her up into the air to meet up with one of the balloons…the smile on her face was priceless. While my older daughter could listen to Disney songs all day long, my younger daughter and I have connected and have shared music and playlists for years. During the pandemic lock-down, we would go for rides in my convertible with the top down and blast music like Emerge from Fischerspooner.
How do you relate to the word optionality, and how is it expressed in your life?
I first learned about option theory while I was doing a summer internship at PaineWebber; not from the mostly clerical job, but from a quantitative genius who had put himself through college by being staked for high limit private poker games. He took it upon himself to teach me about finance and options. However, I didn’t actually start using options in finance for many years. I don’t think I realized how much optionality became important to me in my personal life until after I exited the private equity world.
I was very fortunate for the first years of my career as the job choices mostly came to me, and the options were a binary choice of leave or stay. But at many points, divorce forced my hand. Looking at it from another perspective, my pleasure in being a father and my dedication to my children, made many of the choices for me. I had to make enough money to satisfy my obligations and, of greater importance, I wanted to ensure that my children had a stable home, excellent opportunities and that I could be as near to them as possible and participate fully in their lives. I had to make specific professional choices for income, but I created optionality in my personal life so I could be near and support my kids.
Over the years, and as my children grew, I changed from feeling like I was a prisoner to financial obligations to using optionality in my life in a very positive way. My recent property purchases in Portugal are a good example. I have invested there to diversify, to give myself options for living in another place and culture, and to give my daughters additional mobility.
If someone hears this and asks if I’m *moving* to Portugal; my quick reply is, “tell me what and where my job is, how my daughters are doing, and who I’m dating and what her needs are and then I will tell you where I will be living.” I can create lifestyle options for myself while still holding those as my priorities. Portugal is an option to escape the US for a bit or forever. Who knows, but I know I have plenty of roads I might travel down over the next 20 years. It’s choose your own adventure and I find that suits me well. I want to know my path eventually, but I’m not in a rush to get to the last fork in the road yet.
What is your interest in Portugal?
Portugal has historically had one of the best Golden Visa programs in Europe, which is essentially a path to citizenship. The beauty of the program is that I can pull in my daughter that was interested into the program and by the time she graduates from college, she will have dual citizenship and be able to work and live in the US or anywhere in the European Union. Beyond that, Portugal is an amazing country that always tops the list of places to retire to because of its friendly citizens, weather, healthcare, food, cost of living, non-stop flights to the US, and easy access to anywhere in Europe. I plan on splitting my time between Portugal and the US for the next few years to see what happens.
You have worked in finance with some rather large firms managing huge money. You have also worked in entertainment, technology, and small businesses. What is the thread that connects these for you?
I started my career covering TMT (telecom, media and technology) right as the 1996 Telecom Act opened up everything to competition. I helped fund the wireless industry’s move to digital, cable TV’s move to digital and high-speed data, and telecom start-ups. The industries grew into over half of the market, and I watched entire industries become enormously successful. The thread for me was rapid growth and opportunity for expansion. It didn’t matter if the company needed $1 million or $100 million; they all needed growth capital, and I was at the center of the telecom explosion that created the backbone and services which has enabled the internet to transform our society.
Once AIG bought SunAmerica and we took over their fixed income assets I became a bureaucrat and not a total return portfolio manager…I joked that I had a list of the lists that the credit risk group asked of me. I found myself spending time with the smaller VC and PE companies that I was on the board and were challenging my brain vs. working with the $8.5B portfolio of hundreds of larger companies where I couldn’t have much of an impact. It pushed me to transition to a 16 year run in private equity.
What are some sectors in business that you personally find most exciting today?
I have always been excited about technology. In the 90s, I was interviewed by Cable TV magazine and said that everyone would have a device in the home that would have access to everything allowing for many changes to how we access and utilize information. I said it was the high-speed data that the cable companies would bring to the home that would make all of the difference. I was an early believer in the internet and believed in its evolution. Though not against it, I’m not a huge fan of cryptocurrencies as a permanent store of value, but I do believe blockchain has many applications that will be commonly used. I also believe in the metaverse; it seems certain that some early version of the book Ready Player One style metaverse will be available in our lifetimes. I also believe that the products to service the Metaverse will be hugely successful businesses.
What would you say is your superpower, the thing you are very good at?
Negotiation…I’ve always been good at understanding a situation from everyone’s perspective and doing my best to move to a place beyond the efficient frontier for the good of everyone. I have an ability to have a lot of empathy which goes far in negotiations. It doesn’t always work, and one thing I’ve learned the hard way is that you cannot negotiate with someone that is not mentally healthy….logic does not work for them.
How would you describe your relationship to things, as in objects one purchases, now vs 20 years ago?
I’ve been fortunate in life that my needs/wants have been satisfied because I’ve made enough money to buy most of the things I wanted, within reason. My monetary goals have always been to have enough money to pay for my kids’ education and live a nice comfortable life. I’ve never been focused on money and have been pleasantly surprised with what I have built.
That being said, I do feel very lucky to have made enough money to do special things like taking my kids around the world on adventures. I firmly believe that you must own your things and not let your things own you. My mom would always say that one should focus on quality and elegance over quantity and extravagance. There is nothing I own, except the ring I wear from my grandfather, that would truly upset me to lose. Over the past 20 years, I’ve learned that I prefer shared experiences over stuff…that’s not to say that I don’t create a lot of fun experiences in my car or motorcycle!
What sort of work are you looking to do for the next 10 years?
I failed at a recent interview for an interesting company because the CEO couldn’t seem to wrap his head around the fact that I wasn’t motivated by money. I was surprised because I thought the company was great and was excited to be working with him and his team to help grow the company. The money will come with success, but I was more intrigued by the team and the product. I want to work with smart, energetic, and driven teams that share a mutual respect. I am currently the Executive Chairman of a technology company where I’m literally the dumbest person in a room of scientists…I love it! I do get to shine in the areas that I know and have been tasked with. Over the next 10 years I would hope to shift into sitting on a few boards and helping companies grow; I would want to be an active board member vs. the type that shows up for four meetings a year and reads the docs on the plane to the meeting.
What are your personal goals for the next ten years?
I look forward to seeing my children graduate college and seeing what they will do as they embark on their journey. Ideally, I would like to “age” less than the ten years I will add and I suspect being more mindful of exercise, diet and wellness will play an important role. I hope to find a partner in life to share the next 20 years with.
What are you reading these days?
Growing up, I was never a big reader. My twin sister would read plenty, but I always wanted to be on the street playing with my friends running around and doing sports. My verbal SAT score suffered, but luckily my math skills made up for it. When I started working in High Yield, my job forced me to read all day. Pleasure reading was no longer a pleasure or an escape for me. I started watching movies to relax and escape.
I’ve probably seen more movies than most motion picture executives and was fortunate enough to be on the boards of a couple of successful film companies, which allowed me to say seeing movies was part of my job! As my private equity career started to slow down, I picked up books again. I am currently reading two books. Barbarian Days, A Surfing Life by William Finnegan and Back Sense by Michael Urdang; one is a memoir and the other is a philosophy about dealing with back pain.
Top 3 favorite artists?
I’ve been collecting art for over 25 years and Vik Muniz has always been a large presence in my collection. I would watch any movie in which Sir Anthony Hopkins starred. My music tastes are very eclectic; that being said I find myself always happy listening to LCD Soundsystem and they are amazing in concert.
Top 3 guilty pleasure streaming TV shows?
I used to say that my guilty pleasure was reading Entertainment Weekly, but it is no longer being published. I really liked the first season of The Great. I always felt that GOT was a soap opera geared for men, but really liked the series and looking forward to the prequel. I recently watched the Jeff Bridges and John Lithgow show, The Old Man; Bridges is exactly what you’d expect and I have always liked Lithgow since the first time I saw him playing Lord John Whorfin in The Adventures of Buckaroo Bonzai Across the 8th Dimension.
The 3 non-negotiables in your life today?
1) I have finally learned that my ability to absorb other people’s bullshit is not healthy for me…I’m trying to avoid drama.
2) I rarely turn my cell phone off entirely because I never want to miss a call from my kids; I never want my girls to think they can’t reach their dad in a moment of need. I hope that I can ensure that the word despair will never be in their personal dictionary (another tip from Norman).
3) I will only work in an environment that is challenging, fun, with mutual respect at every level and everyone is looking out for each other.
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Check out Carolyn Lee Arnold’s new memoir, “Fifty First Dates after Fifty,” for a woman’s perspective on late life dating. Fascinating.
Wonderful read and very affirming through shared values, life choices, and engagement with adventure in all aspects of life. Thank you for the article
Wow. Interesting person and fantastic parent! Inspiring.
Barbarian Days is such an exquisitely written book.
1000 Dates in 12 years is impressive! I’m Dish and I write a newsletter on life, love, sex and dating in midlife if you’re interested http://www.PrimeCrush.com to subscribe. It’s complicated, but a lot of people are in relationship transition around something at our stage, whether it is divorce, being widowed, becoming an empty nester, figuring out how to make friends. But either way, good luck. You will find her!
I believe it is a recipe for disaster if you go into dating thinking “I want to find a mother for my daughters”. Try looking for someone you love and are compatible with.
Hi CLT, I couldn’t agree with you more and I’m sorry that I wasn’t more clear in that, at that time, I wanted to find a partner for me, but I couldn’t see myself with someone that was not open to parenting my girls with me; I didn’t have a co-parent already and was not willing to end up with someone that didn’t also love the girls and risk someone treating them as second class kids if we decided to have more children.
LOL 1000 dates in 12 years put me to shame. I’ve been on 5 and yet I learned more about myself through each one. I have chosen to be single for the past 13 years not in search of a parent for my 14 year old but to truly be the parent that I need to be for him. A friend once told me you really don’t need two parents, you need one that truly loves you and cares for you. I didn’t believe her at first, but over the years I soon discovered that every persons life is unique and for ours this is what works. My son is so well rounded and truly happy in life because he has me. Does he need his dad? Maybe yes, but we trust that God knows what is best for us and what my son needs for this moment in life. God bless you on your journey.
Katherine, thank you for your note. As I replied to CLT, the language I chose was not great and leads the reader to the wrong conclusion that I was searching for someone to parent my daughters…I was not. I was searching for a partner in life that was right for me but also would be a strong female role model and participate in parenting. To me, family time has always been important and I wanted to make sure I found someone that had similar core values. I hope that helps clarify this wording confusion.