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Flipping for Philanthropy

Flipping for Philanthropy


I noticed the Guide to Flipping Houses on the internet not too long ago, “5 Easy Steps to House Flipping.” I’m a closet fan of Flip or Flop, Flipping Out and “Flop This House.”

Not one of those steps or shows about flipping included what it could do for philanthropy.

Then I met Thomas (not his real name).

“Flipping” is a term used primarily in the United States to describe purchasing a revenue-generating asset and quickly reselling it for profit. Though flipping can apply to any asset, the term is most often applied to real estate and initial public offerings.

Thomas is a man who defies his age of retirement. He was recently “ripped off” (his words), by that he means his wife died a year ago at the peak of their golden years when they were old enough to retire and yet young enough to enjoy its fruit. They were married for 49 years and enjoyed boating, motorcycle riding, the beach and socializing. After he lost her, I watched Thomas navigate new waters as a single person, it was not easy. It still isn’t.

Thomas and his wife owned several rental properties purchased with the intent to create an income for her because, as he said, he was supposed to “go” first. I guess as a successful insurance agent, he knew the actuarial tables all too well.

Instead of selling the properties, with the strategic guidance of his estate planning attorney, he flipped the houses for philanthropy. It just so happened that he could donate the houses to the Community Foundation, take the tax break and then use the income generated from the sale of the homes to fuel his Donor Advised Fund and a future in philanthropy.

In his goal to simplify his life and his holdings, he just carved out a new role as a philanthropist. Recently he made a $1m pledge to a charity in his and his wife’s hometown up north, a cause close to his wife’s heart, and he made a similar pledge to a like nonprofit in our community.

Instead of taking capital gains, marketing the properties and dealing with tax issues, he took the fast track to the joy of giving back.

For the Foundation, it was an easy gift to accept. An appraisal, a home inspection and a survey and in less than 6 weeks the Foundation took possession and has already had some interest and an offer on one of the houses.

This weekend he will fly up north and formally be recognized for the pledge in his wife’s memory. He has picked out the perfect photo of her for the plaque and the occasion. I know all of this because he called to find out the date we transferred the insurance. When I told him, he said, “ahhhh…..that is her birthday.” We both nodded knowing that there is very little coincidence in one date out of 365. How nice for him to get such an assuring secret message, and how nice for me to be able to share it.

Any time one can take an asset and convert it to philanthropy, we know that we are providing meaningful and creative solutions for donors and nonprofit beneficiaries who make our community better.

Sometimes gifts like these can also create income for life if needed. So, if you know someone like Thomas, or if you have an interest in learning more about donating gifts of appreciated assets, please contact us. Kindness comes in many forms. Sometimes it may even have an address.

About the Southwest Florida Community Foundation
The Southwest Florida Community Foundation, founded in 1976, cultivates regional change for the common good through collective leadership, social innovation and philanthropy to address the evolving community needs in Lee, Collier, Charlotte, Hendry and Glades counties. The Foundation partners with individuals, families and corporations who have created more than 400 philanthropic funds. Thanks to them, the Foundation invested $6.3 million in grants and programs to the community. With assets of more than $126 million, it has provided $79.9 million in grants and scholarships to the communities it serves since inception. The Foundation is the backbone organization for the regional FutureMakers Coalition and Lee County’s Sustainability Plan. The Southwest Florida Community Foundation’s regional headquarters are now located in the historic ACL Train Depot at Collaboratory in downtown Fort Myers, with satellite offices located on Sanibel Island, in LaBelle (Hendry County). For more information, call 239-274-5900 or visit


Carolyn Rogers
Carolyn Rogers