Today, they buried my mentor.
Arie Leibovitz, my confidant and father-like figure here in Detroit, passed away in the early hours of Friday morning.
I first met Arie in early 2015. I just moved to Detroit, I was working part time for Federation and full time for an investment company. I was building from scratch and spearheading a laundry business as I was dating someone outside of the community. It was a tumultuous time — building a company, navigating the cultural dynamic with my family, and trying to find my place as an Israeli in the US and, specifically, in an American Jewish community.
In one of my many conversations with folks about Israel, community and anything in between, I found myself being introduced to Arie by my friend and colleague at the time Danny Greenberg. We completely flopped getting his support for Federation, but in that meeting, I earned a mentor.
He was a tough cookie. Self-made man, Holocaust survivor, Israeli-American who came to the US in 1967 with the shirt on his back and $200 in his pocket. We connected instantaneously since we both started in the laundry industry, served in combat units in the IDF, and our spouses were initially outside the community — just 50 years apart.
He saw that I was hungry, even starving for success and he loved it. Told me it reminded him of himself, way back when, but would lovingly tease me that I was a lot fancier, given my educational background and military officer status. He taught me the importance of cash flow and that where you start is not where you finish, but leverage it to build. This is how he, and later I, transitioned into Real Estate, through understanding the power of cash flow. He actually introduced me to another Ari, from whom I bought my first set of single-family homes in 2018.
He had battle scars and lessons from here to Timbuktu, but also the highest Emotional Intelligence I’ve seen. Rarely was he self-centered, but acutely self-reflective and self-critical.
He was a gifted conversationalist. A person of profound depth and empathy that was second to none. He continuously surprised me and would follow up every conversation a few days later and would inquire about specific issues we discussed. He helped me navigate relationships, family, culture, business and, primarily, personal growth. He didn’t do fluff — he held a mirror to my face and called me out on it, time and time again.
“Shimon, you have to let go. You’re walking around with a chip on your shoulder,” he would say.
He reiterated that there are no free lunches out there, if you want it, you take it, you earn it, you fight for it against any perceived odds.
He who dares wins.
There are no handouts.
Experience is worth its weight in gold.
And yet, through the midst of his rugged exterior, he would regularly call to check in — tell me he missed me, to bring around the kids — and ask when are we meeting for dinner or drinks. We always had plans booked.
His amazing wife Karolyn treated my family like hers. Never having girls herself, she would spoil Eden rotten with the finest dresses and accessories. In my prolonged absence, she would take my family into their home as their own through Hanukkah parties, dances, dinners and outings.
With some of the health challenges Arie had in the past couple of years, we started discussing mortality, planning and legacy. Our talks were always fascinating, informative, anchored in stories and experiences, and hyper engaging. These were lessons no money can buy and I cherished them dearly. We were so deeply engaged that we would regularly find ourselves as the last patrons to leave any restaurant we would frequent, time and time again.
The past few months have been a little rough; Arie always offered guidance and support. This past week, knowing that I was out of town, Arie told me he'd stop by my new house to make sure that the contractors were on schedule and on task. Always taking care of business.
Few people in this world can have a tangible net positive impact on you. He was one of them for me. I never really understood what a mentor was until I met Arie.
In the past few weeks, as if he knew something we didn’t, he insisted on talking about the next phase after he’s gone. I wouldn’t have it, but he again, held a mirror to my face with reality. He shared a few asks and, in a very Arie fashion, offered some thought-provoking wisdom to carry.
We should all be so lucky. I am forever grateful.

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