I just found out my mentor in life passed.

Don Lipsih was all of 24-years young, fresh out of prestigious Colgate University, when he took a small assignment teaching 7th and 8th grade students at All Souls School in little South San Francisco. It must have seemed like a million miles away from his east coast upbringing. As a 12-year old, I, of course, had no concept of just how disruptive this would have been for him… or how courageous he had to be to uproot his entire life and make such a cross-country move.

“Libby” — as we all came to affectionally call him — was without a doubt larger-than-life. At about 6′ 4″ and 300+ lbs., his physicality was amplified to we diminutive 7th graders. A giant, enormous teddy bear.

But it wasn’t his physical stature that made him special… it was who he was: The best teacher I’ve ever had. And more than that, one of the best people I’ve ever known.

One of Libby’s incredible talents was blending seemingly contrasting behaviors. He was quick to laugh, but equally as quick to take whatever grandiose statement a 7th grader was trying to make with utter seriousness. He gave you the respect of an equal, but there was never a doubt of who was in charge. He loved good-natured ribbing, but he also taught us that there were very bright lines in the world that could never be crossed.

The contrasts always made for surprising, refreshing, and interesting exchanges… but ones that never caught you off-guard. Lib, always kind and considerate… always the gentleman… wouldn’t do that to someone.

Most notably, Libby had perspective and wisdom. He was, in fact, the wisest man I’ve ever known. I don’t mention this lightly, most of us spend a lifetime searching for these qualities and never really get there. Lib had them in spades at 24!

As my life-long friend John Marino recently intimated, he changed an entire community of people forever.

Another life-long friend, Dave Rosaia, chimed in that he was the rare educator that actually cared about his kids. High praise coming from a persona that sent lesser teachers ducking for cover.

But Libby didn’t just teach us. He became our friend. I can’t even count the times a half dozen of us would pile into his big ‘ole, bright mustard yellow, larger-than-life Delta 88 convertible and go golfing or to the movies or such.

And he didn’t just have that effect on students, the entire community loved Libby. He was possibly the most beloved person I’ve ever known, too.

And richly deserving. His superpowers were that he made everyone feel special… and, even more appreciated, safe. He simply let you be you.  Incredibly uncommon qualities.

Teaching wasn’t paying all the bills, so he eventually augmented his salary with a bit of catering out of his kitchen — I believe his first business name was something haphazard like “Vittles Unlimited.” My little sister Lisa was helping him on the weekends. Libby brought his Libby magic to every relationship and his small business couldn’t help but grow. It grew so much that, at one point, Lisa had a team of three adults working for her… and she couldn’t even drive yet… if another party needed her, she would literally point to an adult and say “drive, please, now!” Libby knew how to recognize… and unlock… potential, another superpower of his.

Libby’s business grew so much that he was able to buy a flailing catering company that had a great store front location and rebranded his business to “Continental Catering.” He definitely stepped out of his small kitchen and into the big time. It was the 80’s and Silicon Valley was experiencing a second great technology wave. With companies like Apple and Intel making a fortune in tech, Libby was making his fortune running each and every shindig they threw.

Around this time I remember Libby shedding about 100 lbs (!)… and when he hit his goal weight, he bought himself a brand new, totally fancy, totally cool, ivory-colored Porsche 9-2-4. We were, of course, all in awe. :)

Even with the weight loss, the rigors of catering eventually took its toll on his health. And so he retired early… leading what I can best describe as a “wealthy vagabond” existence. He once told me, “if I’m driving past an airport and decide I want to have lunch in Paris, I just pull into short-term parking, buy a plane ticket, and just go. Anything I need I just buy along the way.”

I experienced this firsthand in the most dramatic and surprising way. My wife and I got married in Greece, bringing just our immediate families and our best man & woman with us.  And, of course, Elle’s soon-to-be-godfather Uncle George. Next thing I know, Libby shows up at the wedding! In Greece! Totally unannounced! It was an entrance to beat all entrances.

It was incredible to hear his stories… but there was a sadness, too. The only family he had was an aging mother. He never married, in fact I never even heard him mention a significant other… friends or otherwise. I worried that he was alone in the world.

To this day, I’ve never been able to reconcile that. I’ve never known somebody so loved by so many… just kinda dropping off the face of the earth. It was if he gave so much of himself for so long… that it was impossible for him to give anymore.

We grew distant over the years. Not his fault, mine. Another life-long friend Frank Fano and I always threatened to descend on him some weekend, but we never did. For me, I think it was because I always dreamed of reuniting with Lib in a triumphant way… to talk about amazing and great conquests in business. But, with a schoolboy mentality, I hadn’t yet felt I had achieved anything that would make him truly proud of me.

But I didn’t think time would run out. Stupid schoolboy me.

Years ago I closed down the Oasis Bar, located a few blocks from his catering storefront, and left him a, “how ya doin’, Lib?!” note… to which his reply included:

          “It’s always great to hear from you, even if it’s a card in the door. I’m going to be a very old man before I see you again I think.”

He was, among all his incredibly qualities, simply insightful. He knew.

A few years back — when Lib would have been looking up at 70 — and on the occasion of my 57th birthday — I bucked up. I pulled out another letter he wrote me… one that I had been trying to answer for many years… and was determined to finish my reply to him. It was well past time I told Libby just how much he meant to me.

It was the most personal letter I have ever written… written to the person that believed in me before all others.

Some of it was apologetic, the student worrying about disappointing the teacher. But here’s the part I’d like to share… because I believe it may capture some of what we all felt:

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I never saw the movie, “To Sir With Love.” But the song by Lulu is one of my favorites… in particular the closing verses:

          A friend who taught me right from wrong     
          And weak from strong
          That’s a lot to learn,
          but, what can I give you in return?     

          If you wanted the moon
          I would try to make a star
          But I, would rather you let me give my heart
          To Sir, with love

I was always bummed that this was written from a girl student to a male teacher… because it’s not a very manly thing to share with another man… but the importance of the sentiment is dead-on for me.

At this point in my life, I’m not sure what I can give you except the knowledge that you have been in my heart every day since the morning you walked into our 7th grade classroom. More than a mentor… a father.

To Sir. With Love.

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