Mr. Croteau, who will be 50 in June, grew up in Keene, an old mill town in southern New Hampshire. His father was a factory worker whose education ended at the eighth grade; his mother had some factory jobs, too. Mr. Croteau had a difficult childhood and quit school at 16. He then left home, joined the Navy and drifted through a long series of jobs without finding any real calling. He married his pregnant 19-year-old girlfriend and had two daughters, Lael and Maggie, by the time he was 24.

"I was raised in a family where my grandma lived next door, my uncles lived on the next road over, my dad's two brothers lived next to each other, and I pretty much played with my cousins," he said. "The whole concept of life was that you should try to get a good job in the factory. My mother tried to encourage me. She'd say, 'Dan's bright; ask him a question.' But if I'd said I wanted to go to college, it would have been like saying I wanted to grow gills and breathe underwater."

He always felt that the rich people in town, "the ones with their names on the buildings," as he put it, lived in another world.

Ms. Woolner, 54, comes from that other world. The daughter of a doctor and a dancer, she grew up in a comfortable home in Hartsdale, N.Y., with the summer camps, vacations and college education that wealthy Westchester County families can take for granted. She was always uncomfortable with her money; when she came into a modest inheritance at 21, she ignored the monthly bank statements for several years, until she learned to channel her unease into philanthropy benefiting social causes. She was in her mid-30's and married to a psychotherapist when Isaac and Jonah were born.

"My mother's father had a Rolls-Royce and a butler and a second home in Florida," Ms. Woolner said, "and from as far back as I can remember, I was always aware that I had more than other people, and I was uncomfortable about it because it didn't feel fair. When I was little, what I fixated on with my girlfriends was how I had more pajamas than they did. So when I'd go to birthday sleepovers, I'd always take them a pair of pajamas as a present."