University of Virginia (UVA) alum Penn Holderness and his wife Kim are the very definition of authentic, whether they are appearing on The Amazing Race, posting a musical parody on social media, or bantering with one another in a sketch comedy skit. Their combined creativity, talent, and love of family are as real and relatable as it gets – that’s the key to their likability.
The couple, who lives in Raleigh, North Carolina, caught the attention of a national audience with their first public viral video in 2013, #XMAS Jammies, featuring their two children Lola and Penn Charles. Since then, they’ve garnered over 3 billion views and over 9 million followers across their social media platforms. As content creators and owners of Holderness Family Productions, Penn and Kim put their lives in public view every day through entertaining videos, podcasts, and books.
Penn estimates they’ve created around 2,000 videos. On average, it’s a little more than one every other day or three to four a week,” he says. “The process is almost always us, predominately Kim, noticing something a little unusual or funny every day, whether it’s something with friends, family, each other, aging, or parenting.” The couple takes a moment to laugh about it. “We have a lot of different ways that we introduce comedy skits, such as straight-to-camera admissions and songs. We think about it in all these frameworks,” Penn says.
Penn and Kim come up with a sample script or snippet of a song and run it by their three-member team. “If we are laughing, we run with it. If not, we park it,” Penn says.
After 20 years of marriage, Kim says she is still in awe of Penn’s natural musical talent and abilities when it comes to writing original songs and parodies. “I gave him an idea and said this is funny, but I don’t think it’s a sketch,” Kim says. “I said, ‘You should write a song about it.’” In about 30 minutes, Penn had already written the lyrics. “It’s a true gift,” Kim says. “It’s a weird skill set, and very few people have it. I feel lucky I get to see it every day.”
Penn, who has the same respect for Kim’s talents and abilities, is adamant that Kim is selling herself short. “All the songs come from her ideas,” he says.
Childhood Interests Lead to Promising Careers
Kim’s creative expression surfaced in childhood. “She was an adventurous child from the beginning,” says her mom Peggy Harris. “She laughed a lot. She was a hard worker and a reporter on the school newspaper.” When she was growing up in Sarasota, Fla., Kim divided her interests between dancing and writing. “I always wanted to be a writer. I was always writing little books. It’s funny how we depend on writing now,” Kim says.
When she was in high school, she received a video camera for Christmas one year. She started making silly videos. It was something she really enjoyed. “Looking back, all the things I loved to do as a kid, I am still doing today,” says Kim, who graduated from the University of Florida with a degree in telecommunications.
Growing up in Durham, North Carolina, Penn had undiagnosed ADHD as a child. “For that reason, I bounced around,” he says. He took a couple of years of piano, but stopped in what he refers to as “true ADHD fashion,” then took a couple more years of jazz piano. He performed with the North Carolina Boys Choir.
When it was time for high school, Penn attended a public high school in Durham that focused on theater arts. “I got into all of that, and it brought me back to playing music,” he says.
In college at UVA, Penn was part of an a cappella group called the Hullabahoos and a band called Smith Cooley. “I dabbled in a lot of music,” he says, noting that his musical interests and talents are helpful in the work he does today.
Fellow UVA alumnus Andrew Freiden, 12 On Your Side’s morning meteorologist, was in the same a cappella group with Penn. He describes Penn as charismatic and a great showman. “He was exactly like he is on all of his videos,” says Andrew. “He was athletic, funny, and very smart. He’s also happens to be a musical genius.”
Freiden enjoys watching the Holderness family’s videos and finds them relevant and reflective of Penn’s musical talents. “Penn, if you’re reading this, I am available for a collab,” Andrew says.
Penn’s interest in UVA was sparked by his aunt and uncle who live in Richmond. When it came time to pick a college, he was torn between his devotion to North Carolina and a newfound appreciation for Virginia. “It felt like home, like a safe place for me to have an out-of-network experience and not do the same thing seemingly everyone else I knew was doing,” he says. He describes his time at UVA as a blessing because he was able to build close relationships. “Most of my best friends are people I met from UVA,” he says. “It was an amazing, unbelievable experience for me.”
Penn says he still gets a happy feeling when he drives up Route 29. “It is so special. My brother went to prep school in Orange County at Woodberry Forest. We would drive up all the time. I was blown away by the beauty of Virginia.”
Setting the Stage
Both Penn and Kim got involved in broadcast journalism in the 1990s, several years before the start of YouTube in 2005. “If YouTube had been a thing in the ’90s, I would have tried my hand at becoming an online content creator,” Kim says.
Kim’s goal was always to tell funny stories, but at the time, her options were limited. She thought the clearest path to a prolific writing career was to work in broadcast journalism.
Penn’s introduction to broadcast was less defined than Kim’s. After UVA, where he graduated with a degree in philosophy, he was interested in either law or following in his dad’s footsteps as a Presbyterian minister. “I am a spiritual person. I have a good connection with God, but I didn’t feel like attending seminary was the right thing for me,” he says.
During and after college, Penn watched ESPN Sports Center regularly with friends – so much so, that they urged him to get a job similar to the hosts of that show. Even though he didn’t have a journalism background, he scored an internship at a local television station serving as editor for the sports department. He then got a paying job as a production assistant, running the studio camera and teleprompter before being on-air. “I fell in love with the workflow. The deadlines worked well for my brain,” he says. “Every day was a new challenge.”
Kim and Penn met while they were both working in local news in Orlando.
Kim’s mom remembers that before meeting Penn, Kim was worried about finding the great love of her life. A few months after that, the two met. “I was visiting her one weekend,” Harris says. “Kim told me how much she thought of him. She introduced me to him and later told me, ‘This is the one.’”
Working in broadcast television, like the young couple did, is not the glamorous life that some may lead you to believe. It is an incredibly hard lifestyle driven by deadlines and ratings. After starting a family, Penn and Kim decided, based on the long hours that come with a career in broadcast, to find an alternative career path that would allow them to spend more time as a family.
Kim left broadcast after 14 years, and Penn left after 15 years in the business. The two started their own family business, Holderness Family Productions, in 2016. And the rest, as they say, is history.
“I use the lessons I learned [in broadcast] every day in what we do,” Kim says. “There’s a reason we can turn videos around so quickly. It’s the bootcamp that you go through. You create, edit, and write stories in hours.”
Both Penn and Kim have special skill sets that work well together, says Harris. “Both have the gift of communication, and both are humorous. Nothing that Kim has done has surprised me.”
Ann Marie Taepke, who serves as the Holdernesses’ producer and manager, sees the same humor every day that Kim’s mom describes. “Penn is singing and dancing. It’s hard not to be drawn to him,” she says. “Kim is the dreamer, the one to take the next leap to the big project. She is so funny and quick-witted.”
One of the couple’s strengths is open communication. “They are supportive of each other,” Taepke says. “They listen to each other and work really well balancing their ideas, wants, and needs and making something great at the end of the day.”
Over the years, Kim and Penn have seen a lot of other content creators online follow trends, but that’s not for them. “We learned when we try to do that, it is not as successful for us as when we do our own thing,” Penn says. “Because it’s a new industry and business, we have gotten to build relationships with others and collaborate. That has led to longevity for us. We have developed some cool relationships.” There is no handbook for this, he adds. “You figure it out as you go along.”
Family Comes First
Since appearing in the first #XMAS Jammies video, Kim and Penn’s kids have had more than 10 years to digest all of this. “My oldest in that video was 6 years old, and now she’s going to college,” says Penn.
After the video went viral, Penn noticed the kids were aware that something was going on. “As they grew, they realized there was another facet to this; that it has a little notoriety to it, and maybe being in the videos was not something they necessarily needed to do,” he says.
Lola and Penn Charles have been in fewer and fewer videos as time goes on, but they do pop in occasionally. “We have always paid them. We have accounts for them,” Kim says. “They have always earned money.”
When asked if either of their kids would follow in their footsteps, Kim said that Penn Charles, who is now a sophomore in high school, might.
“I think our son is the one who I could doing what we do,” she says. “He started a Substack where he writes about sports. He will be hosting one of our podcasts. He’s into improv comedy. Our daughter is going to college and has her own identity. I can see her being in law school. I can see her being involved with the business behind the scenes one day. Our son is his father’s son. I can see him taking the path and running this account when we are long gone.”
The Amazing Race, Podcasts, Books, and More
The Holderness family fans were thrilled when Penn and Kim won the 33rd season of The Amazing Race in 2022. The couple were huge fans of the show, so when they were asked to be contestants, they didn’t hesitate to say yes.
When Freiden saw that the two were going to be on the show, he told his friends and family that they were going to win. “I didn’t doubt it for a second,” he says.
Now that the show is over, Kim can say she had a great time. But the rigor of the show and the feats that had to be accomplished weren’t easy for any contestant, especially Kim who has anxiety. “Something fairly amazing about Kim is that talking about anxiety is hard. It’s taken courage, along with a lot of work and self-awareness,” Penn says, noting that Kim talking about it means a lot to viewers. “She does it in a way that makes people feel seen. She has a way of normalizing it.”
Being on The Amazing Race also helped Kim and Penn learn more about themselves and each other as a couple. “They take away your cell phones and any contact with the outside world,” Kim says. “You and your partner focus on this one thing, which is a weird game show challenge. It was one of the best experiences of my life. It was challenging.”
Many of Penn’s favorite moments occurred when the camera was not rolling. “[The experience] gives you the chance to have each other’s back, which sometimes, when you are parenting and working, gets lost,” he says.
Over the years, Penn and Kim have ventured into other endeavors. In 2018, they started the Holderness Family Podcast where they discuss a variety of topics: some personal, some about mental health, and some that are simply fun.
They’ve also written two books: USA Today and Wall Street Journal Bestseller Everybody Fights: So Why Not Get Better at It? and New York Times Best Seller ADHD Is Awesome: A Guide to (Mostly) Thriving with ADHD.
This October they released a children’s version of an ADHD book called All You Can Be with ADHD. “The book is just magic. I am so proud of Penn,” says Kim, noting that parents kept asking when the couple would release a children’s book on ADHD. “Penn has found a real skill in writing for children. There will be another book coming out next year.”
Penn uses imagination and humor to help connect with readers. “Just knowing who my audience is and having the opportunity to affect even a few of them positively is overwhelmingly gratifying for me. I know what it’s like being a kid with ADHD and being given that diagnosis with a bunch of really bad, negative words in the name and the stigma that goes with it,” he says.
While their lives have changed since starting their business, Kim and Penn have always stayed true to who they are. “They have valued experiences more than stuff. They travel together and do things together as a family. I would wish that more people can experience the life that they live together,” says Harris.
Kim and Penn are grateful to the people who have welcomed them into their families via their screens. “I feel like we are all going through these big life milestones together. It’s an incredible community that lifts us up every single day,” Kim says.
