Glenn Henderson’s future appeared in the midst of his workout at a fitness center in Chicago. “I was doing sit ups and I had my eyes closed.” Like an answer to a silent prayer, “I opened my eyes and there she was.”

Knowing a hot commodity when he sees one, he seized the moment and capitalized on a need. Regina recalls, “He saw me getting ready to use a machine incorrectly. He politely came over to help me,” perhaps leaving the impression of a man who values and protects in the process.

Regina—a graduate of Northwestern University with a double major in economics and political science—was drawn to Glenn’s entrepreneurial spirit. “He had that vision of being one’s own boss,” she says. “That was very attractive to me. And I liked that he was doing something that I might be I interested in [for a living].”

After three years of dating, they were wed. Mr. Henderson notes, ”We funded our own marriage. We had [no money].” However, the couple did have an abundance of faith and a motto to live on: “Between the two of us there is nothing that is impossible,” Mrs. Henderson shares. ”Because we had that belief in ourselves, we are successful.”

Investment is a profound theme in the Henderson dynamic. First and foremost, they invest in each other. Glenn is an expert in the field of logistics—the management of the supply and demand chain. “I started in this business years ago as a driver,” he says. “Since then, I’ve worked every aspect of logistics.” As proprietors, they have worked with institutions such as the White House and Hallmark. “What I enjoy most is, no day is the same. We’ve been entrusted with quite a bit in the space of logistics over the years,” Glenn continues. “And we’ve learned the best practices.”

Regina and Glenn have worked as a team for many years; each plays their best position. “He’s the visionary and I’m the clean-up girl,” Regina specifies. “You absolutely have to have a deep personality to work with your spouse. You’re together 24/7. You try not to talk about the office at home. If you can work with your spouse, it’s a fabulous thing.”

Working with his wife is a consistent reminder of family and a constant observation of the quality of partner he chose in life. “Regina certainly has a great deal of intellect that’s stimulating,” Glenn affirms. “She has a command of many areas. As it pertains to me, she’s a motivator, and that’s attractive to me. The motivating factor behind any degree of success that we enjoy today is Regina.”

The Henderson family is thriving. However, owning several businesses together and developing an acute relationship with the stock market did not come without its tribulations.

“Those failures put iron in our soul,” Regina reveals. “Meaning it made us stronger and better having gone through adversity together. We are blessed. Our family has experienced dark times, but we’ve come out on the other side. You have to learn from those times.”

Glenn agrees. “Regina and I are both seriously committed. We don’t say the ‘divorce’ word.” Mr. Henderson chronicles their trial-to-triumph journey in his book, Treasures of Darkness: Prelude to Prosperity. “We were bankrupt twice; we lost everything. We’ve had businesses fail.” As evident in the couple’s motto, they are stronger together. “I source it all back to our friendship first. There’s never a second thought in my mind about who has my back and best interests. We are fortunate enough to allow [our hardships] to bring us closer as opposed to driving a wedge between us.”

Through their lows, the Hendersons volunteered. “Food banks, Meals-on-Wheels… It was so ironic. We were giving food away and we didn’t even have food,” Glenn says. The family now gives to the community in ways comparable to their affluence, including sponsoring backpacks to schools, speaking at numerous colleges, and advising people in various aspects of new business. “We get a great joy out of doing,” Regina says. Being proactive no matter what they were going through is a testament to their collective strength and an aspirational ideal for their kids.

The Hendersons have three children: Valerie (37), who lives in California as a graphic designer and budding actress in L.A., and a son and daughter currently in college—Cameron (21) and Allegra (19). “We are new empty nesters!” exclaims Regina. “I’m enjoying every minute of it. My husband and I are having a blast!”

Cameron and Allegra left the nest with an interest and a skill: how to invest. Early in their mom’s career, Regina says she “started an investment club in order to further my education as well as to help others. I’m passing that knowledge on to my children as well.” She feels it’s time to remove the shroud from the public forum of investing. “I really wish our culture would enter this arena a lot more. Other cultures are very evolved in this aspect,” Regina says.

“Banking, reconciling bank accounts, even investing—I wish it was taught in public schools,” she continues. “People don’t realize you can get involved with investing. Through Ameritrade or E-Trade, you can open up an account online and buy stocks, sure. Stocks run from one dollar to thousands of dollars. It’s amazing how investing a small amount of money on a consistent basis in the stock market increases. But if you’re starting out as a family and you invest a little bit at a time, as your child is growing up, their money grows.”

For example, Cameron was born in 1993. When he was around 10, Regina asked her son to name some things he liked. Among his answers was Marvel Comics. “I looked at how much debt Marvel Comics had. I said, ‘okay, everything looks good. Let’s buy Marvel!’ ” In 2012, Disney bought Marvel Comics for a few billion dollars. “So his stocks are worth much more!” The youngest daughter loved animals; Allegra is a stockholder in PETCO. “It’s great for our children to see their financial growth and learn the ways in which wealth is created.”

Having a child with special needs also tested the family’s endurance. Cameron’s parents made sure he would be able to negotiate socially and have an aptitude about life. When children are diagnosed with autism, “You hear things like, ‘Be cautious of change,’ and ‘Don’t do anything to agitate them.’ ” Regina gathers, “Well, that’s not real life.

“The fact that he is a junior in college is an absolute miracle. The same tenacity we use in business, we used to help him to be the best he could be.” Cameron attends Beacon College, which specializes in the academic degrees of students with learning differences. Located in Leesburg, Florida, “Beacon has done an excellent job with Cameron,” says Regina. “He’s such a joy, we call him Mr. Sunshine. We are very thankful.”

“Cameron is a great gift to this planet,” says his father. “I can count on one hand when he’s had a bad day. He is just a great joy to be around. It’s been a wonderful journey to see the man he’s become today.”

Allegra is off to college as well. Now a sophomore at Stetson University in Deland, Florida, Glenn takes pride in her entrepreneurial gene. “I think she will be carrying the torch,” he says. “She has the business acumen. She’s a thinker, like myself. She introspects quite a bit.” As a father, Glenn realizes the immense responsibility of being a parent and what that role means on a day-to-day basis. “With my daughters, I want to display attributes that they will look for in a spouse,” he says.

Married 31 years, Glenn planned for a year their 25th wedding anniversary in Barbados—18 days of celebrating, island hopping, yachting with a captain and private chef, as well as a recommitment ceremony.

When they arrived in Barbados, the event planner couldn’t wait to meet the woman who inspires Glenn Henderson. Regina recalls, “She said, ‘I’ve been waiting to meet you. Your husband has done so much, I wanted to know who this woman was!’ ” Regina continues, “But that’s just one thing. Every day he is loving on me. I don’t want for anything. I have to be careful what I say… I will look up and it’s there!”

“My wife thinks what I do for her is a big deal, but it’s a pleasure.” Glenn says, “From my end, I did very well when I married Regina, and said ‘until death do we part’ and ‘for better or worse.’ Hopefully, she says the same about me!” She does. “Having Glenn as a partner in life is wonderful. Hopefully, we’ve been an example to our children.” Regina concludes, “Glenn is smart, articulate, hard-working and a great father. We balance one another out. I am fortunate.”

The Coolest Black Family in America is an original series: an ongoing look at the intricacies, layers and compelling beauty of African-American family life. Of course, The Coolest Black Family is not one family but many. In fact, we’ve found that there are as many Coolest Black Families as there are versions of cool. Also consider: family doesn’t always mean mother + father + kids. What defines family is connected hearts and supported souls. Ride with us weekly as we crisscross the country in search of kinfolk whose cool is so palpable and real, it comes second only to their love. Think your cool fam qualifies? Email us at digitalpi[email protected] (with Coolest Black Family in the subject line)!