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greg cantori

Human Powered Tiny House Lover

Who is Greg?

After spending 25+ years as a leader in the nonprofit sector, Greg is now volunteering in translating his passion for housing as a basic human right into tiny living. 

Growing up, Greg, along with his brother Eric and sister Nadia, lived first in public housing in Chicago. He was surrounded by both diversity and poverty. He was also enrolled in one of the first Head Start classes in 1964. This offered Greg an opportunity to interact with people of different backgrounds, ethnicities, financial situations, and races. 

Shortly thereafter, his family moved to Culver City, California and his parents became very active in the Fair Housing Movement in 1968.

Volunteering for the Westside Fair Housing Council, one of the first fair housing nonprofits in the nation, his parents were fair housing testers, posing as a couple interested in renting an apartment before another couple of a different ethnicity went to inquire about the same place. Often, this second (non-Caucasian) couple with identical economic demographics would be quoted a higher price or rejected altogether, and many times they were treated with hostility. Greg, decades later, followed in his parents footsteps and became a volunteer tester for the fair housing nonprofit, Baltimore Neighborhoods.

Later his father, Louis, accepted a teaching position at the American University in Cairo, Egypt.​ There, Greg and his parents lived in Maadi, a wealthy foreign envelope of Cairo. There, Greg witnessed the willful and disdainful segregation of wealthy whites from the rest of society.  


In order to escape the exclusivism, Greg and his family would spend many weekends visiting poorer areas of Cairo and villages up and down the Nile, often getting invited to come into homes to enjoy some tea. It was through those acts of kindness that Greg stumbled on the reality that it's the poverty-stricken around the world who are the most generous.

"… those with the least tend to help the most… the poorest give a larger portion of their income towards charity."

In 1976, Greg and his family returned to Baltimore. But for 16-year-old Greg, re-entry was tough. He attended the public high school, Baltimore Polytechnic Institute, however he learned better doing hands-on, more relevant work. He wanted to spend time with adults who were making things happen, and so got involved in environmental justice and nonprofit work. One of his first volunteer experiences was with the Sierra Club's Baltimore chapter, as he helped VOLPE (Volunteers Opposed to the Leakin Park Expressway) stop I-70 from coming through Baltimore. That experience in nonprofit activism in improving our collective quality of life set Greg on an exciting career path.

"...Sounds Pollyanna-ish, but studies are now showing that giving your time, talent and treasure creates a deep sense of personal fulfillment and even wellness.
The more you give, the better you feel."
Why Is Greg So Passionate About Tiny Housing & Homelessness?

Greg's first love for living tiny and frugally began when he was a college student. In order to save money on housing, Greg decided to live on a boat. He spent $6,000 buying, raising, and fixing a sunken sailboat, and then lived on it for 5 years! Aside from the fact that most of his paychecks as a bike mechanic went into savings, he also got the chance to go sailing every weekend!  He learned you can live large when living tiny.

Greg in his Tiny House, Image Credi: Baltimore Sun
"I never, ever believe in asking someone to do what you wouldn't do yourself. So we've lived in tiny homes and sailboats, we've lived in dangerous neighborhoods, we've lived in community’s of color, we've lived in houses that needed tons of work..."

After finishing college, Greg worked as a cartographer, while renovating houses in the evening and weekends. His experience in running his company, Creative Housing, and serving on a nonprofit board, led to his leading a community development nonprofit; Light Street Housing. In this position, he worked directly with the homeless, hiring many on as staff. This passion and work with those with the least had an incredible impact on him. The team would do gut rehabs for transitional housing and low income first time buyers, provide home repairs for free to the elderly poor, and clean and board vacant homes.
These experiences ultimately led Greg and his wonderfully diverse Light Street Housing team to build a beautiful transitional home for 54 men, complete with wrap-around porch, multiple kitchens and gardens. Men came to this home from area shelters and were able to begin their recovery process with love, care and understanding.
Light Street Housing also planted the seed of the concept for “Homelessness to Homeownership” as they sold homes to a dozen formerly homeless men and women in gentrified neighborhoods, right alongside the wealthy, breaking many racial, social, stigma, and economic barriers. 


Not only did the Light Street Housing’s hard work keep formerly homeless men and women off the street, but the staff helped them establish credit and create real equity through homeownership. 


After seven years of working longs hours and weekends, while struggling to work around government regulations that required Light Street Housing to transition people out of community homes after an arbitrary two years—and seeing the heart-breaking results of throwing people out, often leading to relapses, Greg needed a change. 


He was hired by the Knott Foundation and for the next 12 years as their Executive Director he translated his knowledge of how hard it is to run nonprofits into discretionary grants, including a Cash Flow Loan program, to help struggling boards and staff stabilize their operations during their most difficult times. 
Greg ended his paid part of his career leading the state association, Maryland Nonprofits but has never forgotten his own experiences nor his passion for those without homes. 


He decided to start a new business of Aging in Place Handyman and Home Safety - Little Deeds!  using his experiences with working with the elderly and homeless \would say "Nonprofits need to be run like a business" he flipped that attitude around and said, "Businesses need to be run more like Nonprofits where they deeply care about creating outcomes that benefit everyone." Nonprofits are harder to lead as they have more stakeholders and need to show so much value that people are willing to give them money without any benefit to themselves. 

Today, Greg and his wife are lucky to have an extraordinarily diverse family and they love spending time with their adult daughters, and granddaughter while living aboard their sailboat, Goodwind, and their tiny house, Thistle Dew, now located in West Virginia.


“As I ride my bike past homes worth millions of dollars with a half dozen bedrooms and bathrooms I wonder: Just how many beds does a wealthy couple need to sleep on, and toilets to poop in?
Might they someday allow those without either a bed or toilet live in a nice tiny home in their huge unused back yards? 
Might they take the lead in saying ‘Yes in My Back Yard!’ and become even richer for the experience?
Might that leadership finally make homelessness rare and brief?” 
Greg and his wife on their sailboat, imge credit: Daily Herald
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