Wisdom Project | Harold Grinspoon Wants You to Discover Your Creative Side

By | Sep 27, 2023
Latest, The Wisdom Project

Harold Grinspoon discovered his creative side in his 80s, and he wants to inspire you to discover yours.

Photo credit: Robert Charles Media

Widely known as the founder of PJ Library, which distributes millions of free Jewish children’s books to families around the globe, Harold is an avid outdoorsman who turned his personal shpilkes, his inability to sit still, into a positive force for good.

After a challenging childhood where he struggled with dyslexia and a lack of self confidence, he served in the Navy and in 1959 invested in a multi-family home with a small sum that he borrowed. Harold grew this initial purchase into one of the most successful private real estate investment and management companies in the country, Aspen Square Management.

After acquiring significant personal wealth, Harold was diagnosed with cancer of the tongue in his late 50s. This battle with cancer motivated him to live a life dedicated to more than simply making money. In 1991, he established the Harold Grinspoon Foundation (HGF), and in 2015, he and his wife, Diane Troderman, signed the Giving Pledge, committing to giving away a majority of their wealth to philanthropy.

HGF now has multiple flagship programs. In addition to PJ Library, JCamp 180 provides support services to nonprofit Jewish Camps, Life & Legacy helps Jewish communities secure legacy gifts, Sifriyat Pijama distributes books on Jewish/Israeli heritage in Israeli schools in partnership with the Israeli Ministry of Education, and Voices & Visions uses art to communicate Jewish values. Harold credits the success of these programs to hiring talented professionals tasked with following through in each area. He and his wife, Diane, have 6 children and 11 grandchildren between them.

Harold is also a contemporary sculptor and poet. He works with reclaimed trees, stainless steel, and other materials to transform them into large sculptures, and he began writing poetry 8 months ago. Now 94, Harold sends poems to friends with a note that asks, “Are there other sides of yourself that you’d like to discover?” “I hope you find your own inspiration and follow it where it may take you.”

Six of Harold’s poems are included below.

Harold reads a book from PJ Library to a child.

Who inspired you to start a foundation and PJ Library?

My wife, Diane Troderman, and her friend, Rabbi Yitz Greenberg, inspired me to start the foundation. 

PJ library came about because one day I was listening to Dolly Parton in the car on NPR and she was talking about her program, Imagination Library. She and her partners would pay for books and organize their distribution. Another time at my son’s house, my daughter-in-law, Winnie Sandler Grinspoon, who is amazing and runs the foundation, gave out Jewish books during the holidays and the kids were excited to get them. I thought, “Why should we not have Jewish books for Jewish people?” I came to learn that the most important age for education is when kids are young because that is when we absorb the most in our learning curve. It didn’t take a genius to figure that out. So I bridged those two ideas together for PJ Library.

How did you get started as an entrepreneur?

It came naturally. My father had a vegetable garden, so I went out and sold vegetables. My uncle was in the egg business, so I sold eggs as a kid. I’m a doer. We’ve been in the real estate/apartment house business for 64 years and never lost money any one year. 

How are you able to be successful in so many different areas?

At the foundation, I think we’re very well-disciplined. We do four projects, and we stay within the parameters of that. There are many areas I do not have good follow-through on. It’s all in who you associate with.

I also multitask. I’ll be in one world for a couple of hours. I transfer over to this world, and this world, and this world. So today I did an article on real estate. I spent an hour on my new project. I’ll go out and work on my art project today. I did a poem last night. 

You are known for your walking meetings. How did that get started?

I have a high need for physical exercise. I’ve hiked all over the world. I’ve skied. I bicycle. If you wanted to talk to me, I had to go for a walk because I just couldn’t sit still otherwise.

Harold stays active with exercise, and has hiked all over the world.

Any advice for others on how to take a dream, or an idea, and make it happen?

I think you must have a very viable idea people want to embrace and not push a concept on people. If you look at PJ Library, it fulfills a market demand. Kids love camping, and there was a big need so we developed JCamp180. Camps could never support themselves in what they charge. So we do these challenge grants. We recently committed to $25 million in challenge grants over five years.

Is there anything you’ve changed your mind on?

I think I’m becoming much more aware that the American political process is going through very challenging times. Both parties make me very concerned.

What are you involved with outside the Jewish community?

I support non-Jewish organizations through a private foundation, giving grants to farmers, teachers, and hospitals.  

Any advice for how to live a better life?

If you take your cell phone and turn it off for Shabbat, that may be a blessing. I have a friend, a senior business partner, who was frum, and he benefits very much from keeping Shabbat. We always light candles. My wife is very, very good about lighting candles every Shabbat. I live the life and spirit of Shabbat.

Any words of advice for a long marriage?

Marry an amazing, independent person. My wife Diane is amazing. She is very independent and that’s great. She’s never asked me for advice. And she’s never asked me for comments, either.

A tall elderly man in a blue cardigan and a woman with brown hair and a green shirt smile at the camera. The man's arm is around the woman's shoulder. Green foliage is behind them.

Harold with his wife, Diane.

Do you have any advice for kids who struggle with some of the learning issues that you had growing up?

Well, I’m dyslexic, and the biggest thing you must overcome is an inferiority complex. And if you can afford it, or if your parents can afford it, you have to find yourself a good therapist as a sounding board to put that behind you. I was always close to my mother. My father died when I was 19 years old, but my mother was always there. She was very bright. But we had a handicapped child in the family, and my mother had to put a lot of energy into that.

Are you working on any new projects?

I started writing poetry eight months ago and have four books compiled. Brand new. I’m also going to start a new philanthropic project that came to me after reading Natan Sharansky’s book, Never Alone. Prison, Politics and My People.

Four sculptures by Harold Grinspoon

Blue Lagoon, 2023

Bikes III, 2022

Adamizer, 2023

Family Reunion, 2017

Six poems by Harold Grinspoon


In the twilight of the day,
Have you ever strolled the cemetery
With thousands of tombstones;
And walked the quiet grounds
In the sparkling sunset? 
Can you visualize voices rising up
As you walk slowly by?
What would they speak of?
Would they talk about the fulfillment of their lives.
Or their sparse hours on the earth?
In their parting days, did they reflect.
On what was truly meaningful for them?
Were they honest with themselves?
Did they have a sense of awareness?
Where they happy, Or just passing through life?
As I stroll through the cemetery
Before the curtain comes down
I ask myself:
What is your life about?
Do you feel fulfilled?
If not, what are your options?
Do you have gratitude every day?
Do you have a deep sense of appreciation?
If not, why not?
What epitaph should be on my tombstone?
And what will be on yours?


Let’s go for a walk together.
Perhaps we’ll walk a bit in silence.
Why in silence?
And if we talk, what should our conversation be –
Would we discuss mundane things?
Or should we get into our thoughts;
What do you think –
Are you in touch with your feelings?
Are you comfortable sharing your thoughts?
Let’s keep on walking til it happens.
Is that too risky?


Did you ever have a deep sense of appreciation,
Have you discovered who you are;
Feel much gratitude –
Do you count your blessings every day?
Is there any room for doubt?
Maybe, maybe not.
I am so blessed. I am so blessed.
I hope you are too.



As I emerged from childhood,
Do you know that I didn’t know
My ass from my elbow
About what life was all about?
It was the pain
Of going through life
To discover, with the help of great therapists,
Who I am today.
To know I was not in touch with my feelings,
And how to go about solving that problem.
When I stopped and looked around,
I had to confront my anger
And lack of feelings –
Amazingly, I unencumbered myself
And I was able to discover who I am.



Do you think you ever go there?
I doubt it.
I work my way down the tunnel.
Squeezing my body
Over broken Israeli equipment.
And there lay ahead – the tunnel.
The tunnel was amazing. Well-engineered.
I started to walk away,
putting space between me and the group.
Lonely, step by step. In silence and in fear.
And in anguish.
I moved by myself.
This elaborate tunnel, built to kill Jews. 
I began to panic. Turn around, I must.
Thoughts racing through my head.
Do you know where I was?
Gaza Border. Hamas-dug tunnel.
Death was awaiting, before discovery.



Do you sit back,
Or perhaps stand up,
And think about your childhood?
What was it like?
What does a child know about childhood –
You live in the context of where you are,
Your family environment.
In the days when I was a young child,
It was a custom with Jewish parents
To want their children to be righties.
I couldn’t be a lefty.
My mum made me a righty.
Was that the source of my anger,
My dyslexia –
My inability to write? And inability to spell?
Perhaps this explains why I was
In B curriculum in high school,
While all my friends were in a college curriculum.
All the resentment build up,
I believe it all came from my childhood.
Do you stop and think about your childhood;
Who you were –
Do you think about who you are today?
Do you understand yourself?

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